Patent Description:
The present disclosure relates to a novel compound and an organic light emitting device comprising the same.

For the organic materials used in the organic light emitting devices as described above, the development of new materials is continuously required. <CIT> discloses compounds suitable for OLEDs.

Meanwhile, recently, in order to reduce process costs, an organic light emitting device using a solution process, particularly an inkjet process, has been developed instead of a conventional deposition process. In the initial stage of development, attempts have been made to develop organic light emitting devices by coating all organic light emitting device layers by a solution process, but current technology has limitations. Therefore, only HIL, HTL, and EML are processed by a solution process, and a hybrid process utilizing traditional deposition processes is being studied as a subsequent process.

Therefore, the present disclosure provides a novel material for an organic light emitting device that can be used for an organic light emitting device and at the same time, can be used for a solution process.

According to an aspect of the present disclosure, there is provided a compound represented by the following Chemical Formula <NUM>:
<CHM>
<CHM>
in Chemical Formula <NUM>,.

According to another aspect of the present disclosure, there is provided an organic light emitting device comprising: a first electrode; a second electrode that is provided opposite to the first electrode; and one or more organic material layers that are provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the compound represented by Chemical Formula <NUM>.

The above-mentioned compound represented by Chemical Formula <NUM> can be used as a material for an organic material layer of an organic light emitting device, can be used in a solution process, and can improve the efficiency, achieve low driving voltage and/or improve lifetime characteristics in the organic light emitting device.

As used herein, the notation
<CHM>
and
<CHM>
mean a bond linked to another substituent group.

As used herein, the term "substituted or unsubstituted" means being unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkylsulfoxy group; an arylsulfoxy 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 arylphosphine group; and a heteroaryl containing at least one of N, O and S atoms, or being unsubstituted or substituted with a substituent to which two or more substituents of the above-exemplified substituents are linked. For example, "a substituent in which two or more substituents are linked" may be a biphenyl group. Namely, a biphenyl group may be an aryl group, or it may also be interpreted as a substituent in which two phenyl groups are linked.

In the present disclosure, the carbon number of a carbonyl group is not particularly limited, but is preferably <NUM> to <NUM>. Specifically, the carbonyl group may be a substituent group having the following structural formulas, but is not limited thereto. <CHM>
<CHM>.

In the present disclosure, an ester group may have a structure in which oxygen of the ester group may be substituted by a straight-chain, branched-chain, or cyclic alkyl group having <NUM> to <NUM> carbon atoms, or an aryl group having <NUM> to <NUM> carbon atoms. Specifically, the ester group may be a substituent group having the following structural formulas, but is not limited thereto. <CHM>
<CHM>.

In the present disclosure, the carbon number of an imide group is not particularly limited, but is preferably <NUM> to <NUM>. Specifically, the imide group may be a substituent group having the following structural formulas, but is not limited thereto. <CHM>
<CHM>.

In the present disclosure, the alkyl group may be straight-chain or branched-chain, and the carbon number thereof is not particularly limited, but is preferably <NUM> to <NUM>. According to one embodiment, the carbon number of the alkyl group is <NUM> to <NUM>. According to another embodiment, the carbon number of the alkyl group is <NUM> to <NUM>. According to another embodiment, the carbon number of the alkyl group is <NUM> to <NUM>. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, <NUM>-methylbutyl, <NUM>-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, <NUM>-methylpentyl, <NUM>-methylpentyl, <NUM>-methyl-<NUM>-pentyl, <NUM>,<NUM>-dimethylbutyl, <NUM>-ethylbutyl, heptyl, n-heptyl, <NUM>-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, <NUM>-methylheptyl, <NUM>-ethylhexyl, <NUM>-propylpentyl, n-nonyl, <NUM>,<NUM>-dimethylheptyl, <NUM>-ethyl-propyl, <NUM>,<NUM>-dimethyl-propyl, isohexyl, <NUM>-methylpentyl, <NUM>-methylhexyl, <NUM>-methylhexyl, and the like, but are not limited thereto.

In the present disclosure, an aryl group is not particularly limited, but the carbon number thereof is preferably <NUM> to <NUM>, 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 <NUM> to <NUM>. According to one embodiment, the carbon number of the aryl group is <NUM> to <NUM>. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. The polycyclic aryl group includes a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, or the like, but is not limited thereto.

In the present disclosure, the fluorenyl group may be substituted, and two substituents may be connected to each other to form a spiro structure. In the case where the fluorenyl group is substituted,
<CHM>
and the like can be formed. However, the structure is not limited thereto.

In the present disclosure, a heteroaryl is a heteroaryl containing at least one of O, N, Si and S as a heteroatom, and the carbon number thereof is not particularly limited, but is preferably <NUM> to <NUM>. Examples of the heteroaryl include xanthene, thioxanthene, a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazol group, an oxadiazol group, a triazol group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridyl group, a pyridazine group, a pyrazinyl group, a quinolinyl group, a quinazoline group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazol group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a dibenzofuranyl group, and the like, but are not limited thereto.

In the present disclosure, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, the arylamine group and the arylsily group is the same as the above-mentioned examples of the aryl group. In the present disclosure, the alkyl group in the aralkyl group, the alkylaryl group and the alkylamine group is the same as the above-mentioned examples of the alkyl group. In the present disclosure, the heteroaryl in the heteroarylamine may be applied to the above-mentioned description of the heteroaryl. In the present disclosure, the alkenyl group in the aralkenyl group is the same as the above-mentioned examples of the alkenyl group. In the present disclosure, the above-mentioned description of the aryl group may be applied except that the arylene is a divalent group. In the present disclosure, the above-mentioned description of the heteroaryl may be applied except that the heteroarylene is a divalent group. In the present disclosure, the above-mentioned description of the aryl group or cycloalkyl group may be applied except that the hydrocarbon ring is not a monovalent group but formed by combining two substituent groups. In the present disclosure, the above-mentioned description of the heteroaryl may be applied, except that the heterocyclic group is not a monovalent group but formed by combining two substituent groups.

The present disclosure provides the compound represented by Chemical Formula <NUM>.

The compound represented by Chemical Formula <NUM> contains at least one benzofuranyl, dibenzofuranyl, benzothiophenyl or dibenzothiophenyl in its molecular structure. The compound represented by Chemical Formula <NUM> not only is easy to synthesize, but also contains at least one benzofuranyl, dibenzofuranyl, benzothiophenyl, or dibenzothiophenyl in the molecular structure, whereby it is advantageous for increasing the solubility in a solvent and manufacturing an organic light emitting device by a solution process such as an inkjet process. Particularly preferably, the compound represented by Chemical Formula <NUM> contains one, two, three or four benzofuranyl or benzothiophenyl in the molecular structure.

Preferably, the benzofuranyl is benzofuran-<NUM>-yl (
<CHM>
), the dibenzofuranyl is dibenzofuranyl-<NUM>-yl (
<CHM>
), the benzothiophenyl is benzothiophen-<NUM>-yl (
<CHM>
), and the dibenzothiophenyl is dibenzothiophen-<NUM>-yl (
<CHM>
).

Preferably, one or two of R<NUM> is
<CHM>
and the rest is R<NUM>.

Preferably, Ar<NUM> and Ar<NUM> are each independently phenyl substituted with R<NUM>, or naphthyl substituted with R<NUM>. More preferably, Ar<NUM> is phenyl substituted with R<NUM>, and Ar<NUM> is phenyl substituted with R<NUM>, or naphthyl substituted with R<NUM>.

Preferably, at least one of R<NUM> is benzofuranyl, dibenzofuranyl, benzothiophenyl, or dibenzothiophenyl; and the rest are hydrogen, deuterium, a C<NUM>-<NUM> alkyl, or a C<NUM>-<NUM> aryl. More preferably, at least one of R<NUM> is benzofuranyl, dibenzofuranyl, benzothiophenyl, or dibenzothiophenyl; and the rest are hydrogen, deuterium, methyl, propyl, isopropyl, butyl, isobutyl, tertbutyl, or phenyl.

Preferably, R<NUM> is methyl, ethyl, propyl, isopropyl, butyl, or tertbutyl.

Preferably, the Chemical Formula <NUM> is represented by any one of the following Chemical Formulas <NUM> to <NUM>:
<CHM>
<CHM>
<CHM>
<CHM>
in Chemical Formulas <NUM> to <NUM>,
Ar<NUM>, Ar<NUM>, R<NUM>, and R<NUM> are as defined above.

Representative examples of the compound represented by Chemical Formula <NUM> is as follows:
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>.

Meanwhile, the present disclosure provides a method for preparing the compound represented by Chemical Formula <NUM>, as shown in the following Reaction Scheme <NUM> as an example:
<CHM>
<CHM>.

In Reaction Scheme <NUM>, the definition of the remaining substituents except for X are the same as defined above, and X is halogen, preferably bromo or chloro.

Step <NUM> is an amine substitution reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and a reactive group for the amine substitution reaction can be modified as known in the art. Step <NUM> is a reaction with Bl<NUM>, which is preferably carried out in the presence of a base. The above preparation method may be further embodied in Preparation Examples described hereinafter.

On the other hand, the compound according to the present disclosure can form an organic material layer, particularly a light emitting layer, of an organic light emitting device by a solution process. For this purpose, the present disclosure provides a coating composition including the above-mentioned compound according to the present disclosure and a solvent.

The solvent is not particularly limited as long as it is a solvent capable of dissolving or dispersing the compound according to the present disclosure. Examples of the solvent may include chlorine-based solvents such as chloroform, methylene chloride, <NUM>,<NUM>-dichloroethane, <NUM>,<NUM>,<NUM>-trichloroethane, chlorobenzene and o-dichlorobenzene; ether-based solvents such as tetrahydrofuran and dioxane; aromatic hydrocarbon-based solvents such as toluene, xylene, trimethylbenzene, and mesitylene; aliphatic hydrocarbon-based solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane and n-decane; ketone-based solvents such as acetone, methyl ethyl ketone, and cyclohexanone; ester-based solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate; polyalcohols such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin and <NUM>,<NUM>-hexanediol, and derivatives thereof; alcohol-based solvents such as methanol, ethanol, propanol, isopropanol and cyclohexanol; sulfoxide-based solvents such as dimethyl sulfoxide; amide-based solvents such as N-methyl-<NUM>-pyrrolidone and N,N-dimethylformamide; benzoate-based solvents such as butylbenzoate, and methyl-<NUM>-methoxybenzoate; tetraline; <NUM>-phenoxy-toluene, and the like. In addition, the above-mentioned solvents may be used singly or in combination of two or more solvents.

Further, the coating composition may further include a compound used as a host material, and the compound used for the host material will be described later. Further, the coating composition may include a compound used as a dopant material, and the compound used for the dopant material will be described later.

Further, the viscosity of the coating composition is preferably <NUM> cP to <NUM> cP, and coating is easily carried out in the above range. Moreover, the concentration of the compound according to the present disclosure in the coating composition is preferably <NUM> wt/v% to <NUM> wt/v%.

In another embodiment of the present disclosure, there is provided a method for forming a light emitting layer using the above-mentioned coating composition. Specifically, the method includes the steps of: coating the above-mentioned light emitting layer according to the present disclosure onto the anode by a solution process; and heat-treating the coated coating composition.

The solution process uses the above-mentioned coating composition according to the present disclosure, and refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

The heat treatment temperature in the heat treatment step is preferably from <NUM> to <NUM>. Further, a heat treatment time may be <NUM> minute to <NUM> hours, more preferably <NUM> minutes to <NUM> hour. Further, the heat treatment is preferably carried out in an inert gas atmosphere such as argon and nitrogen.

In another embodiment of the present disclosure, there is provided an organic light emitting device including the compound represented by Chemical Formula <NUM>. In one example, the present disclosure provides an organic light emitting device comprising: a first electrode; a second electrode that is provided opposite to the first electrode; and one or more organic material layers that are provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the compound represented by Chemical Formula <NUM>.

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 multilayered 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 comprising a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as the organic material layer. However, the structure of the organic light emitting device is not limited thereto, and it may include a smaller number of organic layers.

Further, the organic material layer may include a light emitting layer, wherein the light emitting layer may include the compound represented by Chemical Formula <NUM>. Particularly, the compound according to the present disclosure can be used as a dopant of the light emitting layer.

Further, the organic light emitting device according to the present disclosure may 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 may 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, the structure of an organic light emitting device according to an embodiment of the present disclosure is illustrated in <FIG>.

<FIG> shows an example of an organic light emitting device comprising a substrate <NUM>, an anode <NUM>, a hole injection layer <NUM>, a hole transport layer <NUM>, a light emitting layer <NUM>, an electron injection and transport layer <NUM>, and a cathode <NUM>.

The organic light emitting device according to the present disclosure may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by Chemical Formula <NUM>. Further, 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.

As the anode material, generally, a material having a large work function is preferably used so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material include metals such as vanadium, chrome, copper, zinc, and gold, or an alloy thereof; metal oxides such as zinc oxides, indium oxides, indium tin oxides (ITO), and indium zinc oxides (IZO); a combination of metals and oxides, such as ZnO:Al or SnO<NUM>:Sb; conductive compounds such as poly(<NUM>-methylthiophene), poly[<NUM>,<NUM>-(ethylene-<NUM>,<NUM>-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, and the like, but are not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably a compound which has a capability of transporting the holes, thus has a hole injecting effect in the anode and an excellent hole injecting effect to the light emitting layer or the light emitting material, prevents excitons produced in the light emitting layer from moving to a hole injection layer or the electron injection material, and further is excellent in the ability to form a thin film. It is preferable that a HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and a HOMO of a peripheral organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, an arylamine-based organic material, a hexanitrilehexaazatriphenylene-based organic material, a quinacridone-based organic material, a perylene-based organic material, anthraquinone, polyaniline and polythiophene-based conductive polymer, and the like, but are not limited thereto.

The hole transport layer is a layer that receives holes from a hole injection layer and transports the holes to the light emitting layer. The hole transport material is suitably a material having large mobility to the holes, which may receive holes from the anode or the hole injection layer and transfer the holes to the light emitting layer. Specific examples thereof include an arylamine-based organic material, a conductive compound, a block copolymer in which a conjugate portion and a non-conjugate portion are present together, and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material may be a fused aromatic ring derivative, a heterocycle-containing compound or 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 heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex, 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, anthracene, chrysene, periflanthene and the like, which have an arylamino group. The styrylamine compound is a compound where at least one arylvinyl group is substituted in substituted or unsubstituted arylamine, in which one or two or more substituent groups selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted. Specific examples thereof include styrylamine, styryldiamine, styryltriamine, styryltetramine, and the like, but are not limited thereto. Further, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

The electron injection and transport layer is a layer for simultaneously performing the roles of an electron transport layer and an electron injection layer that inject electrons from an electrode and transport the received electrons up to the light emitting layer, and is formed on the light emitting layer or the electron adjustment layer. The electron injection and transport material is suitably a material which can receive electrons well from a cathode and transfer the electrons to a light emitting layer, and has a large mobility for electrons. Specific examples of the electron injection and transport material include: an Al complex of <NUM>-hydroxyquinoline; a complex including Alq<NUM>; an organic radical compound; a hydroxyflavone-metal complex, a triazine derivative, and the like, but are not limited thereto. Alternatively, LiF, NaF, NaCl, CsF, Li<NUM>O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, a metal complex compound, a nitrogen-containing <NUM>-membered ring derivative, and the like can be used, but are not limited thereto.

The organic light emitting device according to the present disclosure may be a frontside emission type, a backside emission type, or a double-sided emission type based on the used material.

The preparation of the compound represented by Chemical Formula <NUM> and the organic light emitting device including the same will be specifically described in the following Examples. However, the following Examples are provided for illustrative purposes only.

Compound <NUM>-a (<NUM> eq. ) and Compound <NUM>-b (<NUM> eq. ) were placed in a round bottom flask and dissolved in anhydrous THF (<NUM>). K<NUM>CO<NUM>(aq. ) (<NUM> eq. ) was added dropwise to the reaction solution. Pd(PPh<NUM>)<NUM> (<NUM> mol%) was added dropwise thereto at a bath temperature of <NUM>, and the mixture was stirred overnight. After the reaction, the reaction mixture was thoroughly cooled at room temperature, sufficiently diluted with CH<NUM>Cl<NUM>, and then washed with CH<NUM>Cl<NUM>/brine. The organic layer was separated, water was removed with MgSO<NUM> and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to prepare Compound <NUM>-c (yield: <NUM>%).

Compound <NUM>-d (<NUM> eq. ), NaOt-Bu (<NUM> eq. ) and Compound <NUM>-c (<NUM> eq. ) were placed in a round bottom flask and dissolved in anhydrous toluene (<NUM>). Pd(t-Bu<NUM>P)<NUM>(<NUM> mol%) was added dropwise thereto at a bath temperature of <NUM>, and the mixture was stirred overnight. After the reaction, the reaction mixture was thoroughly cooled at room temperature, sufficiently diluted with CH<NUM>Cl<NUM>, and then washed with CH<NUM>Cl<NUM>/brine. The organic layer was separated, water was removed with MgSO<NUM> and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to prepare Compound <NUM>-e (yield: <NUM>%).

Compound <NUM>-e (<NUM> eq. ), NaOt-Bu (<NUM> eq. ) and Compound <NUM>-f (<NUM> eq. ) were placed in a round bottom flask and dissolved in anhydrous toluene (<NUM>). Pd(t-Bu<NUM>P)<NUM>(<NUM> mol%) was added dropwise thereto at a bath temperature of <NUM>, and the mixture was stirred overnight. After the reaction, the reaction mixture was thoroughly cooled at room temperature, sufficiently diluted with CH<NUM>Cl<NUM>, and then washed with CH<NUM>Cl<NUM>/brine. The organic layer was separated, water was removed with MgSO<NUM> and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to prepare Compound <NUM>-g (yield: <NUM>%).

Compound <NUM>-i (yield: <NUM>%) was prepared in the same manner as in Preparation Example of Compound <NUM>-e, except that Compound <NUM>-g was used instead of Compound <NUM>-d and Compound <NUM>-h was used instead of Compound <NUM>-c.

Compound <NUM>-i (<NUM> eq. ), NaOt-Bu (<NUM> eq. ) and Compound <NUM>-j (<NUM> eq. ) were placed in a round bottom flask and dissolved in anhydrous toluene (<NUM>). Pd(t-Bu<NUM>P)<NUM>(<NUM> mol%) was added dropwise thereto at a bath temperature of <NUM>, and the mixture was stirred overnight. After the reaction, the reaction mixture was thoroughly cooled at room temperature, sufficiently diluted with CH<NUM>Cl<NUM>, and then washed with CH<NUM>Cl<NUM>/brine. The organic layer was separated, water was removed with MgSO<NUM> and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to prepare Compound <NUM>-k (yield: <NUM>%).

Compound <NUM>-k (<NUM> eq. ) was placed in a round bottom flask and dissolved in anhydrous toluene (<NUM>). Bl<NUM> (<NUM> eq. ) was slowly added dropwise to the reaction solution, and the mixture was stirred overnight at a bath temperature of <NUM>. After the reaction, the reaction mixture was sufficiently cooled at room temperature and diluted with CH<NUM>Cl<NUM>. EtNi-Pr<NUM>(<NUM> eq. Na<NUM>S<NUM>O<NUM>(aq. ) were sequentially added dropwise to the reaction mixture and washed with CH<NUM>Cl<NUM>/H<NUM>O. The organic layer was separated, water was removed with MgSO<NUM> and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to prepare Compound <NUM> (yield: <NUM>%). m/z [M+H]+ <NUM>.

Compound <NUM>-b (yield: <NUM>%) was prepared in the same manner as in Preparation Example of Compound <NUM>-e, except that Compound <NUM>-a was used instead of Compound <NUM>-d.

Compound <NUM>-c (yield: <NUM>%) was prepared in the same manner as in Preparation Example of Compound <NUM>-k, except that Compound <NUM>-b was used instead of Compound <NUM>-i.

Compound <NUM> (yield: <NUM>%) was prepared in the same manner as in Preparation Example of Compound <NUM>, except that Compound <NUM>-c was used instead of Compound <NUM>-k. m/z [M+H]+ <NUM>.

Compound <NUM>-a (<NUM> eq. ) and Compound <NUM>-b (<NUM> eq. ) were placed in a round bottom flask and dissolved in anhydrous THF (<NUM>). K<NUM>CO<NUM>(aq. )(<NUM> eq. ) was added dropwise to the reaction solution. Pd(PPh<NUM>)<NUM> (<NUM> mol%) was added dropwise thereto at a bath temperature of <NUM>, and the mixture was stirred overnight. After the reaction, the reaction mixture was thoroughly cooled at room temperature, sufficiently diluted with CH<NUM>Cl<NUM>, and then washed with CH<NUM>Cl<NUM>/brine. The organic layer was separated, water was removed with MgSO<NUM> and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to prepare Compound <NUM>-b (yield: <NUM>%).

Compound <NUM>-b (<NUM> eq. ), NaOt-Bu (<NUM> eq. ) and Compound <NUM>-c (<NUM> eq. ) were placed in a round bottom flask and dissolved in anhydrous toluene (<NUM>). Pd(t-Bu<NUM>P)<NUM>(<NUM> mol%) was added dropwise thereto at a bath temperature of <NUM>, and the mixture was stirred overnight. After the reaction, the reaction mixture was thoroughly cooled at room temperature, sufficiently diluted with CH<NUM>Cl<NUM>, and then washed with CH<NUM>Cl<NUM>/brine. The organic layer was separated, water was removed with MgSO<NUM> and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to prepare Compound <NUM>-d (yield: <NUM>%).

Compound <NUM>-f (yield: <NUM>%) was prepared in the same manner as in Preparation Example of Compound <NUM>-k, except that Compound <NUM>-d was used instead of Compound <NUM>-i and Compound <NUM>-e was used instead of Compound <NUM>-j.

Compound <NUM>-g (yield: <NUM>%) was prepared in the same manner as in Preparation Example of Compound <NUM>-k, except that Compound <NUM>-f was used instead of Compound <NUM>-j.

Compound <NUM> (yield: <NUM>%) was prepared in the same manner as in Preparation Example of Compound <NUM>, except that Compound <NUM>-g was used instead of Compound <NUM>-k. m/z [M+H]+ <NUM>.

Compound <NUM>-e (<NUM> eq. ) NaOt-Bu (<NUM> eq. ) and Compound <NUM>-i (<NUM> eq. ) were placed in a round bottom flask and dissolved in anhydrous toluene (<NUM>). Pd(t-Bu<NUM>P)<NUM>(<NUM> mol%) was added dropwise thereto at a bath temperature of <NUM>, and the mixture was stirred overnight. After the reaction, the reaction mixture was thoroughly cooled at room temperature, sufficiently diluted with CH<NUM>Cl<NUM>, and then washed with CH<NUM>Cl<NUM>/brine. The organic layer was separated, water was removed with MgSO<NUM> and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to prepare Compound <NUM>-a (yield: <NUM>%).

Compound <NUM> (yield: <NUM>%) was prepared in the same manner as in Preparation Example of Compound <NUM>, except that Compound <NUM>-a was used instead of Compound <NUM>-k. m/z [M+H]+ <NUM>.

Compound <NUM>-b (yield: <NUM>%) was prepared in the same manner as in Preparation Example of Compound <NUM>-e, except that Compound <NUM>-a was used instead of Compound <NUM>-c and Compound <NUM>-a was used instead of Compound <NUM>-d.

Compound <NUM>-c (yield: <NUM>%) was prepared in the same manner as in Preparation Example of Compound <NUM>-k, except that Compound <NUM>-b was used instead of Compound <NUM>-i and Compound <NUM>-f was used instead of Compound <NUM>-j.

Compound <NUM>-a (yield: <NUM>%) was prepared in the same manner as in Preparation Example of Compound <NUM>-k, except that Compound <NUM>-e was used instead of Compound <NUM>-j.

Compound <NUM>-c (yield: <NUM>%) was prepared in the same manner as in Preparation Example of Compound <NUM>-k, except that Compound <NUM>-b was used instead of Compound <NUM>-i and Compound <NUM>-a was used instead of Compound <NUM>-j.

Compound <NUM>-a (<NUM> eq. ) and Compound <NUM>-b (<NUM> eq. ) were placed in a round bottom flask and dissolved in anhydrous THF (<NUM>). K<NUM>CO<NUM>(aq. ) (<NUM> eq. ) was added dropwise to the reaction solution. Pd(PPh<NUM>)<NUM> (<NUM> mol%) was added dropwise thereto at a bath temperature of <NUM>, and the mixture was stirred overnight. After the reaction, the reaction mixture was thoroughly cooled at room temperature, sufficiently diluted with CH<NUM>Cl<NUM>, and then washed with CH<NUM>Cl<NUM>/brine. The organic layer was separated, water was removed with MgSO<NUM> and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to prepare Compound <NUM>-b (yield: <NUM>%).

Compound <NUM>-c (yield: <NUM>%) was prepared in the same manner as in Preparation Example of Compound <NUM>-k, except that Compound <NUM>-b was used instead of Compound <NUM>-i and Compound <NUM>-e was used instead of Compound <NUM>-j.

Compound <NUM>-d (yield: <NUM>%) was prepared in the same manner as in Preparation Example of Compound <NUM>-k, except that Compound <NUM>-b was used instead of Compound <NUM>-i and Compound <NUM>-c was used instead of Compound <NUM>-j.

Compound <NUM> (yield: <NUM>%) was prepared in the same manner as in Preparation Example of Compound <NUM>, except that Compound <NUM>-d was used instead of Compound <NUM>-k. m/z [M+H]+ <NUM>.

Compound <NUM> was prepared in the same manner as in Preparation Example of Compound <NUM>, except that Compound <NUM>-a was used instead of Compound <NUM>-e. m/z [M+H]+ <NUM>.

Compound <NUM>-a (yield: <NUM>%) was prepared in the same manner as in Preparation Example of Compound <NUM>-e, except that Compound <NUM>-a was used instead of Compound <NUM>-c and Compound <NUM>-g was used instead of Compound <NUM>-d.

Compound <NUM>-b (yield: <NUM>%) was prepared in the same manner as in Preparation Example of Compound <NUM>-k, except that Compound <NUM>-a was used instead of Compound <NUM>-i and Compound <NUM>-e was used instead of Compound <NUM>-j.

Compound <NUM>-c (yield: <NUM>%) was prepared in the same manner as in Preparation Example of Compound <NUM>-k, except that Compound <NUM>-b was used instead of Compound <NUM>-i and Compound <NUM>-b was used instead of Compound <NUM>-j.

Compound <NUM> was prepared in the same manner as in Preparation Example of Compound <NUM>, except that Compound <NUM>-a was used instead of Compound <NUM>-b. m/z [M+H]+ <NUM>.

Compound <NUM>-e (<NUM> eq. ), NaOt-Bu (<NUM> eq. ) and Compound F-<NUM> (<NUM> eq. ) were placed in a round bottom flask and dissolved in anhydrous toluene(<NUM>). Pd(t-Bu<NUM>P)<NUM>(<NUM> mol%) was added dropwise thereto at a bath temperature of <NUM>, and the mixture was stirred for <NUM> days. After the reaction, the reaction mixture was thoroughly cooled at room temperature, sufficiently diluted with CH<NUM>Cl<NUM>, and then washed with CH<NUM>Cl<NUM>/brine. The organic layer was separated, water was removed with MgSO<NUM> and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to prepare Compound F-<NUM> (yield: <NUM>%).

Compound F-<NUM> (<NUM> eq. ) was placed in a round bottom flask and dissolved in anhydrous toluene(<NUM>). Bl<NUM> (<NUM> eq. ) was slowly added dropwise to the reaction solution, and the mixture was stirred overnight at a bath temperature of <NUM>. After the reaction, the reaction mixture was sufficiently cooled at room temperature and diluted with CH<NUM>Cl<NUM>. EtNi-Pr<NUM> (<NUM> eq. Na<NUM>S<NUM>O<NUM> (aq. ) were sequentially added dropwise to the reaction mixture, and washed with CH<NUM>Cl<NUM>/H<NUM>O. The organic layer was separated, water was removed with MgSO<NUM> and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to prepare Compound F (yield: <NUM>%). m/z [M+H]+ <NUM>.

Compound G was prepared in the same manner as in Comparative Example <NUM>, except that Compound G-<NUM> was used instead of Compound F-<NUM>. m/z [M+H]+ <NUM>.

Compound <NUM>-j (<NUM> eq. ), NaOt-Bu (<NUM> eq. ) and Compound H-<NUM> (<NUM> eq. ) were placed in a round bottom flask and dissolved in anhydrous toluene(<NUM>). Pd(t-Bu<NUM>P)<NUM>(<NUM> mol%) was added dropwise thereto at a bath temperature of <NUM>, and the mixture was stirred overnight. After the reaction, the reaction mixture was thoroughly cooled at room temperature, sufficiently diluted with CH<NUM>Cl<NUM>, and then washed with CH<NUM>Cl<NUM>/brine. The organic layer was separated, water was removed with MgSO<NUM> and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to prepare Compound H-<NUM> (yield: <NUM>%).

Compound H-<NUM> (<NUM> eq. ) was placed in a round bottom flask and dissolved in anhydrous toluene(<NUM>). Bl<NUM>(<NUM> eq. ) was slowly added dropwise to the reaction solution, and the mixture was stirred overnight at a bath temperature of <NUM>. After the reaction, the reaction mixture was sufficiently cooled at room temperature and diluted with CH<NUM>Cl<NUM>. EtNi-Pr<NUM> (<NUM> eq. Na<NUM>S<NUM>O<NUM> (aq. ) were sequentially added dropwise to the reaction mixture, and washed with CH<NUM>Cl<NUM>/H<NUM>O. The organic layer was separated, water was removed with MgSO<NUM> and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to prepare Compound H (yield: <NUM>%). m/z [M+H]+ <NUM>.

A glass substrate on which ITO (indium tin oxide) was coated as a thin film to a thickness of <NUM>Å was put into distilled water in which a detergent was dissolved, and ultrasonically cleaned. At this time, a product manufactured by Fischer Co. was used as the detergent, and as the distilled water, distilled water filtered twice using a filter manufactured by Millipore Co. After the ITO was cleaned for <NUM> minutes, ultrasonic cleaning was repeated twice using distilled water for <NUM> minutes. After the cleaning with distilled water was completed, the substrate was ultrasonically cleaned with solvents of isopropyl alcohol, acetone, and methanol, dried, and then the substrate was cleaned for <NUM> minutes and then transferred to a glove box.

A coating composition, in which the following compound O and compound P (weight ratio of <NUM>:<NUM>) were dissolved in cyclohexanone at <NUM> wt/v%, was spin-coated (<NUM> rpm) on the ITO transparent electrode, and heat-treated (cured) at <NUM> for <NUM> minutes to form a hole injection layer with a thickness of <NUM>Å. A coating composition, in which the following polymer Q (Mn: <NUM>,<NUM>; Mw: <NUM>,<NUM>; measured by GPC (Agilent <NUM> series) using PC Standard) was dissolved in toluene at <NUM> wt/v%, was spin-coated (<NUM> rpm) on the hole injection layer, and heat-treated at <NUM> for <NUM> minutes to form a hole transport layer with a thickness of <NUM>Å. A coating composition, in which the previously prepared compound <NUM> and the following compound R (weight ratio of <NUM>:<NUM>) were dissolved in cyclohexanone at <NUM> wt/v%, was spin-coated (<NUM> rpm) on the hole transport layer, and heat-treated at <NUM> for <NUM> minutes to form a light emitting layer with a thickness of <NUM>Å. After transferring to a vacuum evaporator, the following compounds S was vacuum-deposited on the light emitting layer to form an electron injection and transport layer with a thickness of <NUM>Å. LiF (<NUM>Å), and aluminum (<NUM>Å) were sequentially deposited on the electron injection and transport layer to form a cathode.

In the above-mentioned process, the vapor deposition rate of the organic material was maintained at <NUM> to <NUM>Å/sec, the deposition rate of LiF was maintained at <NUM>Å/sec, the deposition rate of aluminum was maintained at <NUM>Å/sec, and the degree of vacuum during the deposition was maintained at <NUM>×<NUM>-<NUM> to <NUM>×<NUM>-<NUM> torr (<NUM>·<NUM>-<NUM> to <NUM>·<NUM>-<NUM> Pa).

An organic light emitting device was manufactured in the same manner as in Experimental Example <NUM>, except that the compounds shown in Table <NUM> below were used instead of Compound <NUM> as the dopant of the light emitting layer.

An organic light emitting device was manufactured in the same manner as in Experimental Example <NUM>, except that the compounds shown in Table <NUM> below were used instead of Compound <NUM> as a dopant of the light emitting layer.

The driving voltage, external quantum efficiency (EQE), and lifetime were measured by applying a current of <NUM> mA/cm<NUM> to the organic light emitting devices manufactured in the Experimental Examples and Experimental Comparative Examples, and the results are shown in Table <NUM> below. At this time, the external quantum efficiency (EQE) was calculated as "(the number of emitted photon)/(the number of injected charge carrier) × <NUM>", and T90 means the time required for the luminance to be reduced to <NUM>% of the initial luminance (<NUM> nit).

As shown in Table <NUM> above, the organic light emitting devices comprising the compounds of the present disclosure as the dopant of the light emitting layer exhibits excellent characteristics in terms of efficiency, driving voltage and lifetime.

Claim 1:
A compound represented by the following Chemical Formula <NUM>:
<CHM>
in Chemical Formula <NUM>,
at least one of R<NUM> is
<CHM>
the rest are R<NUM>,
Ar<NUM> and Ar<NUM> are each independently a C<NUM>-<NUM> aryl substituted with R<NUM>, or a C<NUM>-<NUM> heteroaryl substituted with R<NUM> and containing at least one heteroatom selected from the group consisting of N, O and S,
at least one of R<NUM> is benzofuranyl, dibenzofuranyl, benzothiophenyl, or dibenzothiophenyl; the rest are each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C<NUM>-<NUM> alkyl, a substituted or unsubstituted C<NUM>-<NUM> alkenyl, a substituted or unsubstituted C<NUM>-<NUM> alkynyl, a substituted or unsubstituted C<NUM>-<NUM> cycloalkyl, or a substituted or unsubstituted C<NUM>-<NUM> aryl; or two adjacent R<NUM>s are connected to each other to form a substituted or unsubstituted C<NUM>-<NUM> alkylene, and
R<NUM> is a substituted or unsubstituted C<NUM>-<NUM> alkyl.