Patent Description:
The organic material layer frequently has a multilayered structure that comprises different materials in order to enhance efficiency and stability of the organic light emitting device, and 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 and the like.

There is a continuing need for the development of new materials for - the organic materials used in the organic light emitting devices as described above.

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 in a layer device structure by a solution process, and a hybrid process utilizing traditional deposition processes is being studied as a subsequent process.

In this regard, the present disclosure provides novel materials for organic light emitting devices that can be used for an organic light emitting device and simultaneously, can be deposited by a solution process.

Patent Literature <NUM>: <CIT>
<CIT> discloses compounds for inclusion in an organic light emitting device.

According to an aspect of the present disclosure, there is provided a compound represented by the following Chemical Formula <NUM>:
<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 provided opposite 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 include a cured product of the above-mentioned compound.

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

<FIG> show NMR data of each compound prepared in Examples of the present disclosure.

As used herein, the notation <IMG> or <IMG> means 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 group 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 connected. For example, "a substituent in which two or more substituents are connected" 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 connected.

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 compound 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 compound 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 compound having the following structural formulas, but is not limited thereto. <CHM>
<CHM>.

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

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>-methyl-butyl, <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 phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, or the like, but is not limited thereto.

In the present disclosure, the fluorenyl group may be substituted, and two substituents may be linked with 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 group is a heteroaryl 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 <NUM> to <NUM>. Examples of the heteroaryl group include a xanthene group, a thioxanthene group, 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 aforementioned 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 aforementioned examples of the alkyl group. In the present disclosure, the heteroaryl in the heteroarylamine can be applied to the aforementioned description of the heteroaryl group. In the present disclosure, the alkenyl group in the aralkenyl group is the same as the aforementioned examples of the alkenyl group. In the present disclosure, the aforementioned description of the aryl group may be applied except that the arylene is a divalent group. In the present disclosure, the aforementioned description of the heteroaryl group can be applied except that the heteroarylene is a divalent group. In the present disclosure, the aforementioned description of the aryl group or cycloalkyl group can be applied except that the hydrocarbon ring is not a monovalent group but formed by combining two substituent groups. In the present disclosure, the aforementioned description of the heterocyclic group can be applied, except that the heteroaryl group is not a monovalent group but formed by combining two substituent groups.

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

Preferably, L is phenylene, biphenyldiyl, or spirobifluorenediyl. More preferably, L is any one selected from the group consisting of:
<CHM>.

Preferably, L<NUM> and L<NUM> are single bonds.

Preferably, R<NUM> is hydrogen; deuterium; or methyl.

Preferably, Ar<NUM> and Ar<NUM> are each independently a substituent group represented by:
<CHM>
wherein,.

Preferably, Ar<NUM> and Ar<NUM> are each independently any one selected from the group consisting of:
<CHM>
<CHM>
<CHM>
<CHM>.

Preferably, Ar<NUM> and Ar<NUM> are the same as each other.

X<NUM> and X<NUM> are each independently -L"-R", L" is a single bond, -O-, -S-, -CH<NUM>-, -CH<NUM>O-, -OCH<NUM>-, or -CH<NUM>OCH<NUM>-, and R" is any one selected from the group consisting of:
<CHM>
<CHM>
<CHM>.

Preferably, R'<NUM> and R"<NUM> are each independently hydrogen or methyl, and n1 and m1 are each independently an integer of <NUM> to <NUM>. Also preferably, R'<NUM> and R"<NUM> are the same as each other.

Preferably, R'<NUM>, R'<NUM>, R"<NUM> and R"<NUM> are hydrogen.

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

A method for preparing the compound represented by Chemical Formula <NUM> is shown in the following Reaction Scheme <NUM>.

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

If the final compound in Reaction Scheme <NUM> has a bilaterally symmetrical structure, step <NUM> can be omitted. The reaction of step <NUM> and step <NUM> above 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. The above preparation method may be further embodied in the Preparation Examples described hereinafter.

The compound according to the present disclosure can form an organic material layer, particularly a hole transport layer, of an organic light emitting device by a solution process. For this purpose, a coating composition can be prepared comprising 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 butyl benzoate 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 viscosity of the coating composition is preferably <NUM> cP to <NUM> cP, and coating is easy within the above range. Further, in the coating composition, the concentration of the compound according to the present disclosure is preferably <NUM> wt/v% to <NUM> wt/v%.

Further, the coating composition may further include one, two or more types of additives selected from the group consisting of a thermal polymerization initiator and a photopolymerization initiator.

Examples of the thermal polymerization initiator may include peroxides such as methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, acetyl acetone peroxide, methyl cyclohexanone peroxide, cyclohexanone peroxide, isobutyryl peroxide, <NUM>,<NUM>-dichlorobenzoyl peroxide, bis-<NUM>,<NUM>,<NUM>-trimethylhexanoyl peroxide, lauryl peroxide, benzoyl peroxide, or azo-based such as azobis isobutylnitrile, azobis dimethylvaleronitrile and azobis cyclohexylnitrile, but are not limited thereto.

Examples of the photopolymerization initiator may include acetophenone-based or ketal-based photopolymerization initiators such as diethoxyacetophenone, <NUM>,<NUM>-dimethoxy-<NUM>,<NUM>-diphenylethan-<NUM>-one, <NUM>-hydroxycyclohexyl-phenyl-ketone, <NUM>-(<NUM>-hydroxyethoxy)phenyl-(<NUM>-hydroxy-<NUM>-propyl)ketone, <NUM>-benzyl-<NUM>-dimethylamino-<NUM> -(<NUM>-morpholinophenyl)butanone-<NUM>,<NUM>-hydroxy-<NUM>-methyl-<NUM> -phenylpropan-<NUM> -one, <NUM>-methyl-<NUM>-morpholino(<NUM>-methylthiophenyl)propan-<NUM>-one and <NUM>-phenyl-<NUM>,<NUM>-propanedion-<NUM>-(o-ethoxycarbonyl)oxime, benzoin ether-based photopolymerization initiators such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether and benzoin isopropyl ether, benzophenone-based photopolymerization initiators such as benzophenone, <NUM>-hydroxybenzophenone, <NUM>-benzoyl naphthalene, <NUM>-benzoylbiphenyl and <NUM>-benzoylphenyl ether, thioxanthone-based photopolymerization initiators such as <NUM>-isopropylthioxanthone, <NUM>-chlorothioxanthone, <NUM>,<NUM>-dimethylthioxanthone, <NUM>,<NUM>-diethylthioxanthone and <NUM>,<NUM>-dichlorothioxanthone, and other photopolymerization initiators such as ethyl anthraquinone, <NUM>,<NUM>,<NUM>-trimethylbenzoyldiphenylphosphine oxide, <NUM>,<NUM>,<NUM>-trimethylbenzoylphenylethoxyphosphine oxide, bis(<NUM>,<NUM>,<NUM>-trimethylbenzoyl)phenylphosphine oxide, bis(<NUM>,<NUM>-dimethoxy benzoyl)-<NUM>,<NUM>,<NUM>-trimethylpentylphosphine oxide, but are not limited thereto.

Moreover, those having a photopolymerization promoting effect can also be used alone or in combination with the photopolymerization initiator. Examples thereof include triethanolamine, methyldiethanolamine, ethyl <NUM>-dimethylaminobenzoate, isoamyl <NUM>-dimethylamino benzoate, (<NUM>-dimethylamino)ethyl benzoate, <NUM>,<NUM>'-dimethylaminobenzophenone, and the like, but are not limited thereto.

A hole transport layer can be produced using the above-mentioned coating composition. Specifically, the method can include the steps of coating the above-mentioned coating composition onto the anode or onto the hole injection layer formed on the anode by a solution process, and heat-treating the coated coating composition.

The solution process uses the coating composition 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>. A heat treatment time may be from <NUM> minute to <NUM> hours, more preferably <NUM> minutes to <NUM> hour. In another example, the heat treatment is preferably carried out in an inert gas atmosphere such as argon and nitrogen. Further, a step of evaporating a solvent may be further included between the coating step and the heat treatment or light treatment step.

According to yet another embodiment of the present disclosure, there is provided an organic light emitting device comprising a cured product of the compound represented by Chemical Formula <NUM>.

The organic light emitting device comprises a first electrode; a second electrode that is provided opposite 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 of the organic material layers include a cured product of the compound according to the present disclosure.

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>. In such a structure, the compound represented by Chemical Formula <NUM> may be included in the hole injection layer, the hole transport layer, or the light emitting layer.

The organic light emitting device according to the present disclosure may be manufactured by materials and methods known in the art, except that the light emitting layer includes the compound according to the present disclosure.

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.

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 an electron 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 compound, 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 layer 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, and fluoranthene compounds. Examples of the heterocycle-containing compound include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

The dopant material includes an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex, or the like. Specifically, the aromatic amine derivative is a fused aromatic ring derivative having a substituted or unsubstituted arylamino group and includes arylamino group-including pyrene, anthracene, chrysene, peryflanthene and the like, and the styrylamine compound is a compound in which substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, and one, two or more substituents 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. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetramine or the like is included, but the styrylamine compound is not limited thereto. In addition, the metal complex includes indium complexes, platinum complexes or the like, but is not limited thereto.

The electron transport layer is a layer which receives electrons from an electron injection layer and transports the electrons to a light emitting layer, and an electron transport material is suitably a material which may 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 transport material include: an Al complex of <NUM>-hydroxyquinoline; a complex including Alq<NUM>; an organic radical compound; a hydroxyflavone-metal complex, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material, as used according to the related art. In particular, appropriate examples of the cathode material are a typical material which has a 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.

The electron injection layer is a layer which injects electrons from an electrode, and is preferably a compound which has a capability of transporting electrons, has an effect of injecting electrons from a cathode and an excellent effect of injecting electrons into a light emitting layer or a light emitting material, prevents excitons produced from the light emitting layer from moving to a hole injection layer, and is also excellent in the ability to form a thin film. Specific examples of the electron injection layer include 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, but are not limited thereto.

The organic light emitting device according to the present disclosure may be a front side emission type, a back side emission type, or a double side emission type according to the used material.

The preparation of the compound represented by Chemical Formula <NUM> according to the present disclosure and the organic light emitting device containing the same will be described in detail in the following examples. However, these examples are presented for illustrative purposes only, and are not intended to limit the scope of the present disclosure.

Mg (<NUM>, <NUM> mmol), I<NUM>(<NUM>) and THF (<NUM>) were placed in a <NUM> round bottom flask under a nitrogen atmosphere, and stirred for <NUM> minutes. <NUM>-Bromostyrene (<NUM>, <NUM> mmol) was added thereto, and the mixture was stirred for a day while a <NUM> water bath was placed under the round bottom flask. Dissolution of Mg was identified by the solution becoming black. Ether (<NUM>) was added thereto to dilute the reaction solution. Tris(pentafluorophenyl)borane (<NUM>, <NUM> mmol) was dissolved in ether (<NUM>) and slowly added to the reaction solution for <NUM> minutes. The solution was stirred for a day. Na<NUM>CO<NUM>(<NUM>, <NUM>, <NUM> mmol) was slowly added to the reaction solution. The organic solvent was extracted using ethyl acetate (<NUM> × <NUM>), and residual water was removed with MgSO<NUM>. In order to additionally remove residual water and impurities, the result was distilled with benzene using Dean-stark. When approximately <NUM> of the solvent was left, the solution was cooled and filtered to give Compound I' (<NUM>, yield: <NUM> %).

Compound I' (<NUM>, <NUM> mmol), distilled water (<NUM>) and Ph<NUM>ICl(<NUM>, <NUM> mmol) were placed in a <NUM> round bottom flask, and stirred for <NUM> hour. Acetone (<NUM>) was added to the reaction solution to cause precipitation, and the precipitate was filtered and dried to give Compound I (<NUM>, yield: <NUM>%).

Methyltriphenyl potassium bromide (<NUM>, <NUM> mmol) and THF (<NUM>) were placed in a <NUM> round bottom flask, and stirred at <NUM> for <NUM> minutes. n-BuLi(<NUM>, <NUM> mmol, <NUM> in hexane) was slowly added to the reaction solution, and stirred at <NUM> for <NUM> minutes. <NUM>-Formyl-<NUM>,<NUM>,<NUM>,<NUM>-tetrafluoro-<NUM>-bromobenzene (<NUM>, <NUM> mmol, <NUM> in THF) was slowly added to the reaction solution at <NUM>. The reaction solution was stirred while gradually raising the temperature to room temperature. After <NUM> hours, ether (<NUM>) and saturated NH<NUM>Cl solution (<NUM>) were added to the reaction solution. The organic solvent was extracted with ether (<NUM>×<NUM>) and the residual water was removed with MgSO<NUM>. The resulting material was subjected to column chromatography with ethyl acetate:hexane = <NUM>:<NUM> (v:v) to give Compound II' (<NUM>, yield: <NUM>%).

Mg (<NUM>, <NUM> mmol), THF (<NUM>) and I<NUM>(<NUM>) were placed in a <NUM> round bottom flask, and stirred. Compound I' (<NUM>, <NUM> mmol) was added to the reaction solution, and stirred at room temperature. After <NUM> hours, complete dissolution of Mg was identified by the solution becoming black, and ether (<NUM>) and BCl<NUM>(<NUM>, <NUM> mmol, <NUM> in hexane solution) were added over <NUM> minutes. After stirring the reaction solution for a day, Na<NUM>CO<NUM> (<NUM>, <NUM> mmol, <NUM> in H<NUM>O) was added. The synthesized material was extracted with ethyl acetate (<NUM> × <NUM>), and then the residual water was removed with MgSO<NUM>. After removing all the solvent, water was completely removed with Dean-stark using benzene, and the solids were filtered to give Compound II" (<NUM>, yield: <NUM>%).

Compound II" (<NUM>, <NUM> mmol), <NUM>-(<NUM>-vinylbenzyl)pyridin-<NUM>-ium chloride (<NUM>, <NUM> mmol), H<NUM>O (<NUM>) and methylene chloride (<NUM>) were placed in a <NUM> round bottom flask, and vigorously stirred for <NUM> minutes. The organic solvent was extracted with ether (<NUM> × <NUM>) and the residual water was removed with MgSO<NUM>. The solvent was removed and dried in vacuo to give Compound II (<NUM>, yield: <NUM>%).

<NUM>-Bromo-<NUM>,<NUM>,<NUM>,<NUM>-tetrafluoro-<NUM>-vinylbenzene (<NUM>, <NUM> mmol) was added to THF (<NUM>) in a <NUM> round bottom flask, and stirred at -<NUM> for <NUM> minutes. n-BuLi (<NUM>, <NUM> mmol, <NUM> in hexane) was slowly added to the solution, and stirred at -<NUM> for <NUM> minutes. BCl<NUM> (<NUM>, <NUM> mmol, <NUM> in hexane solution) was added to the reaction solution -<NUM> over <NUM> minutes. The reaction solution was stirred for a day while slowly raising the temperature to room temperature, and then water (<NUM>) was added. The synthesized material was extracted with ethyl acetate (<NUM> × <NUM>), and then all solvent was removed. Water was completely removed with Dean-stark using benzene, and the solids were filtered to give Compound III" (<NUM>, yield: <NUM>%).

Compound III" (<NUM>, <NUM> mmol), diphenyliodonium chloride (<NUM>, <NUM> mmol), water (<NUM>) and acetone (<NUM>) were placed in a <NUM> round bottom flask, and vigorously stirred for <NUM> minutes. The result was extracted using dichloromethane (<NUM> × <NUM>), and then dried after removing the solvent to give Compound III (<NUM>, yield: <NUM>%).

Potassium carbonate (<NUM>, <NUM> mmol) was placed in a <NUM> round bottom flask, to which DMF (<NUM>) was added. To the flask, <NUM>,<NUM>,<NUM>,<NUM>-tetrafluorophenol (<NUM>, <NUM> mmol) was added, and the mixture was stirred at <NUM> for <NUM> minutes. <NUM>-Vinylbenzyl chloride (<NUM>, <NUM> mmol) was slowly added to the reaction solution and stirred at <NUM> for <NUM> hours. Then, water (<NUM>) and ethyl acetate (<NUM>) were added. The organic layer was extracted with ethyl acetate (<NUM> × <NUM>) and the residual water was removed with MgSO<NUM>. The resulting material was subjected to column chromatography from ethyl acetate:hexane = <NUM>:<NUM> (v:v) to give Compound IV' (<NUM>, yield: <NUM>%).

Compound IV' (<NUM>, <NUM> mmol) was placed in a <NUM> round bottom flask, to which ether (<NUM>) was added, and the mixture was stirred. The reaction solution was cooled to -<NUM>, and stirred for <NUM> minutes. n-BuLi (<NUM>, <NUM> mmol, <NUM> in hexane) was slowly injected thereto over <NUM> minutes. Then, the result was stirred for <NUM> hour. BCl<NUM> (<NUM>, <NUM> mmol, <NUM> in hexane) was slowly added over <NUM> minutes. The temperature of the reaction solution was slowly raised to room temperature. After stirring the reaction solution for a day, water (<NUM>) was added thereto. The synthesized material was extracted using ether (<NUM> × <NUM>), and all the solvent was removed. After that, water was completely removed with Dean-stark using benzene, and the solids were filtered to give Compound IV" (<NUM>, yield: <NUM>%).

Compound IV" (<NUM>, <NUM> mmol), diphenyl iodonium chloride (<NUM>, <NUM> mmol), water (<NUM>) and acetone (<NUM>) were placed in a <NUM> round bottom flask, and vigorously stirred for <NUM> minutes. The organic solvent was extracted with methylene chloride (<NUM> × <NUM>) and the solvent was removed. The resulting material was subjected to column chromatography from methylene chloride: acetone = <NUM>:<NUM> (v:v) to give Compound IV (<NUM>, yield: <NUM>%).

<NUM>,<NUM>'-Dibromobiphenyl (<NUM>, <NUM> mmol), Pd(tBu<NUM>P)<NUM> (<NUM>), NaOtBu (<NUM>, <NUM> mmol) were placed in a reactor which was purged with nitrogen. Toluene (<NUM>) and <NUM>-fluoro-<NUM>-methylaniline (<NUM>, <NUM> mmol) were added thereto and stirred at <NUM> overnight. The reaction mixture was worked up by adding ethyl acetate and brine, and then purified by column chromatography to give Compound <NUM>-<NUM>, and NMR results (<NUM> NMR (<NUM>, CD<NUM>Cl<NUM>)) are shown in <FIG>.

Compound <NUM>-<NUM> (<NUM>, <NUM> mmol), Pd(tBu<NUM>P)<NUM> (<NUM>) and NaOtBu (<NUM>, <NUM> mmol) were placed in a reactor which was purged with nitrogen. Toluene (<NUM>) and Compound <NUM>-<NUM> (<NUM>, <NUM> mmol) were added thereto, and stirred at <NUM> overnight. The reaction mixture was worked up by adding ethyl acetate and brine, and then purified by column chromatography to give Compound <NUM>, and NMR results (<NUM> NMR (<NUM>, CDCl<NUM>)) are shown in <FIG>.

<NUM>,<NUM>'-dibromobiphenyl (<NUM>, <NUM> mmol), Pd(tBu<NUM>P)<NUM> (<NUM>) and NaOtBu (<NUM>, <NUM> mmol) were placed in a reactor which was purged with nitrogen. Toluene (<NUM>) and <NUM>,<NUM>-difluoroaniline (<NUM>, <NUM> mmol) were added thereto, and stirred at <NUM> overnight. The reaction mixture was worked up by adding ethyl acetate and brine, and then purified by column chromatography to give Compound <NUM>-<NUM>, and NMR results (<NUM> NMR (<NUM>, CDCl<NUM>)) are shown in <FIG>.

Compound <NUM>-<NUM> (<NUM>, <NUM> mmol), Pd(tBu<NUM>P)<NUM> (<NUM>, <NUM> mmol) and NaOtBu (<NUM>, <NUM> mmol) were placed in a reactor which was purged with nitrogen. Toluene (<NUM>) and Compound <NUM>-<NUM> (<NUM>, <NUM> mmol) were added thereto, and stirred at <NUM> overnight. The reaction mixture was worked up by adding ethyl acetate and brine, and then purified by MPLC and then recrystallized with DCM to give Compound <NUM>, and NMR results (<NUM> NMR (<NUM>, CD<NUM>Cl<NUM>)) are shown in <FIG>.

<NUM>,<NUM>'-dibromobiphenyl (<NUM>, <NUM> mmol), Pd(tBu<NUM>P)<NUM> (<NUM>) and NaOtBu (<NUM>) were placed in a reactor which was purged with nitrogen. Toluene (<NUM>) and <NUM>-fluoroaniline (<NUM>, <NUM> mmol) were added thereto, and stirred at <NUM> overnight. The reaction mixture was worked up by adding ethyl acetate and brine, and then purified by column chromatography to give Compound <NUM>-<NUM>.

Compound <NUM>-<NUM> (<NUM>, <NUM> mmol), Pd(tBu<NUM>P)<NUM>(<NUM>) and NaOtBu (<NUM>, <NUM> mmol) were placed in a reactor which was purged with nitrogen. Toluene (<NUM>) and Compound <NUM>-<NUM> (<NUM>, <NUM> mmol) were added thereto, and stirred at <NUM> overnight. The reaction mixture was worked up by adding ethyl acetate and water, and then purified by column chromatography to give Compound <NUM>, and NMR results (<NUM> NMR (<NUM>, CDCl<NUM>)) are shown in <FIG>.

Diiodobiphenyl (<NUM>, <NUM> eq. ), NaOtBu(<NUM>, <NUM> eq. ), toluene (<NUM>), and <NUM>-fluoroaniline (<NUM>, <NUM> eq. ) were placed in a round bottom flask. After nitrogen gassing, the temperature was raised to <NUM>. Pd(tBu<NUM>P)<NUM> (<NUM>, <NUM> mol%) was added thereto, and then stirred at <NUM> for <NUM> hours. The reaction mixture was worked up by adding ethyl acetate and brine, and then purified by column chromatography to give Compound <NUM>-<NUM>.

Compound <NUM>-<NUM> (<NUM> eq. ) and Compound <NUM>-<NUM> (<NUM>, <NUM> eq. ) were placed in a round bottom flask, and NaOtBu (<NUM>, <NUM> eq. ), toluene (<NUM>) and Pd(tBu<NUM>P)<NUM> (<NUM>, <NUM> mol%) were added and then stirred at <NUM> for <NUM> hours. Then, the resulting material was purified by column chromatography to give Compound <NUM>. MS: [M+H]+ = <NUM>.

Diiodobiphenyl (<NUM>, <NUM> eq. ), NaOtBu(<NUM>, <NUM> eq. ), toluene (<NUM>), and <NUM>-fluoroaniline (<NUM>, <NUM> eq. ) were placed in a round bottom flask. After nitrogen gassing, the temperature was raised to <NUM>. Pd(tBu<NUM>P)<NUM> (<NUM>, <NUM> mol%) was added thereto, and then stirred at <NUM> for <NUM> hour. The reaction mixture was worked up by adding ethyl acetate and brine, and then purified by column chromatography to give Compound <NUM>-<NUM>.

Compound <NUM>-<NUM> (<NUM> eq. ) and Compound <NUM>-<NUM> (<NUM>, <NUM> eq. ) were placed in a round bottom flask, and NaOtBu (<NUM>, <NUM> eq. ), toluene (<NUM>) and Pd(tBu<NUM>P)<NUM> (<NUM>, <NUM> mol%) were added thereto, and then stirred at <NUM> for <NUM> hours. Then, the resulting material was purified by column chromatography to give Compound <NUM>. MS: [M+H]+ = <NUM>.

Diiodobiphenyl (<NUM>, <NUM> eq. ), <NUM>,<NUM>-difluoroaniline (<NUM>, <NUM> eq. ), NaOtBu (<NUM>, <NUM> eq) and toluene (<NUM>) were placed in a round bottom flask. After nitrogen gassing, the temperature was raised to <NUM>. Pd(tBu<NUM>P)<NUM> was added thereto, and then stirred at <NUM> overnight.

Compound <NUM>-<NUM> (<NUM>, <NUM> eq. ), Compound <NUM>-<NUM> (<NUM>, <NUM> eq. ), NaOtBu (<NUM>, <NUM> eq. ) and toluene (<NUM>) were placed in a round bottom flask. After nitrogen gassing, the temperature was raised to <NUM>. Pd(tBu<NUM>P)<NUM> (<NUM>, <NUM> mol%) was added thereto, and then stirred at <NUM> for <NUM> hour. The reaction mixture was then purified by column chromatography to give Compound <NUM>. MS: [M+H]+ = <NUM>.

Compound <NUM>-<NUM> (<NUM> eq. ), NaOtBu (<NUM>, <NUM> eq. ), toluene (<NUM>) and <NUM>-fluoroaniline (<NUM>, <NUM> eq. ) were placed in a round bottom flask. After nitrogen gassing, the temperature was raised to <NUM>. Pd(tBu<NUM>P)<NUM> (<NUM>, <NUM> mol%) was added thereto, and then stirred at <NUM> for <NUM> hour. The reaction mixture was worked up by adding ethyl acetate and brine, and then purified by column chromatography to give Compound <NUM>-<NUM>.

Compound <NUM>-<NUM> (<NUM> eq. ) and Compound <NUM>-<NUM> (<NUM>, <NUM> eq. ) were placed in a round bottom flask, and NaOtBu (<NUM>, <NUM> eq. ), toluene (<NUM>) and Pd(tBu<NUM>P)<NUM> (<NUM>, <NUM> mol%) were added thereto, and then stirred at <NUM> for <NUM> hour. Then, the resulting material was purified by column chromatography to give Compound <NUM>. MS: [M+H]+ = <NUM>.

Compound <NUM>-<NUM> (<NUM> eq. ), NaOtBu (<NUM>, <NUM> eq. ), toluene (<NUM>) and <NUM>-fluoro-<NUM>-methylaniline (<NUM> eq. ) were placed in a round bottom flask. After nitrogen gassing, the temperature was raised to <NUM>. Pd(tBu<NUM>P)<NUM> (<NUM>, <NUM> mol%) was added thereto, and then stirred at <NUM> for <NUM> hour. The reaction mixture was worked up by adding ethyl acetate and brine, and then purified by column chromatography to give Compound <NUM>-<NUM>.

Compound <NUM>-<NUM> (<NUM> eq. ), NaOtBu (<NUM>, <NUM> eq. ), toluene (<NUM>) and <NUM>,<NUM>-difluoroaniline (<NUM> eq. ) were placed in a round bottom flask. After nitrogen gassing, the temperature was raised to <NUM>. Pd(tBu<NUM>P)<NUM> (<NUM>, <NUM> mol%) was added thereto, and then stirred at <NUM> for <NUM> hour. The reaction mixture was worked up by adding ethyl acetate and brine, and then purified by column chromatography to give Compound <NUM>-<NUM>.

Diiodobiphenyl (<NUM>, <NUM> eq. ), <NUM>,<NUM>,<NUM>-trifluoroaniline (<NUM> eq. ), NaOtBu (<NUM>, <NUM> eq) and toluene (<NUM>) were placed in a round bottom flask. After nitrogen gassing, the temperature was raised to <NUM>. Pd(tBu<NUM>P)<NUM> (<NUM>, <NUM> mol%) was added thereto, and then stirred at <NUM> overnight. The reaction mixture was worked up by adding ethyl acetate and brine, and then purified by column chromatography to give Compound <NUM>-<NUM>.

Compound <NUM>-<NUM> (<NUM> eq. ) and Compound <NUM>-<NUM> (<NUM> eq. ) were placed in a round bottom flask, and NaOtBu (<NUM> eq. ), toluene (<NUM>) and Pd(tBu<NUM>P)<NUM> (<NUM>, <NUM> mol%) were added thereto, and then stirred at <NUM> for <NUM> hour. Then, the resulting material was purified by column chromatography to give Compound <NUM>. MS: [M+H]+ = <NUM>.

Compound <NUM>-<NUM> (<NUM> eq. ), NaOtBu (<NUM>, <NUM> eq. ), toluene (<NUM>) and <NUM>,<NUM>,<NUM>-trifluoroaniline (<NUM> eq. ) were placed in a round bottom flask. After nitrogen gassing, the temperature was raised to <NUM>. Pd(tBu<NUM>P)<NUM> (<NUM> mol%) was added thereto, and then stirred at <NUM> for <NUM> hour. The reaction mixture was worked up by adding ethyl acetate and brine, and then purified by column chromatography to give Compound <NUM>-<NUM>.

Compound <NUM>-<NUM> (<NUM> eq. ) and Compound <NUM>-<NUM> (<NUM> eq. ) were placed in a round bottom flask, and NaOtBu (<NUM> eq. ), toluene (<NUM>) and Pd(tBu<NUM>P)<NUM> (<NUM> mol%) were added thereto, and then stirred at <NUM> for <NUM> hour. Then, the resulting material was purified by column chromatography to give Compound <NUM>. MS: [M+H]+ = <NUM>.

Diiodobiphenyl (<NUM>, <NUM> eq. ), <NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentafluoroaniline (<NUM> eq. ), NaOtBu (<NUM>, <NUM> eq) and toluene (<NUM>) were placed in a round bottom flask. After nitrogen gassing, the temperature was raised to <NUM>. Pd(tBu<NUM>P)<NUM> (<NUM> mol%) was added thereto, and then stirred at <NUM> for <NUM> hour. The reaction mixture was worked up by adding ethyl acetate and brine, and then purified by column chromatography to give Compound <NUM>-<NUM>.

Compound <NUM>-<NUM> (<NUM> eq. ), NaOtBu (<NUM>, <NUM> eq. ), toluene (<NUM>) and <NUM>,<NUM>,<NUM>,<NUM>,<NUM>-pentafluoroaniline (<NUM> eq. ) were placed in a round bottom flask. After nitrogen gassing, the temperature was raised to <NUM>. Pd(tBu<NUM>P)<NUM> (<NUM> mol%) was added thereto, and then stirred at <NUM> for <NUM> hour. The reaction mixture was worked up by adding ethyl acetate and brine, and then purified by column chromatography to give Compound <NUM>-<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 and acetone, dried, and then the substrate was cleaned for <NUM> minutes and then transferred to a glove box.

On the transparent ITO electrode prepared as above, a <NUM> wt% cyclohexanone solution containing the compound <NUM> prepared in the previous Example <NUM> as a host and the compound III prepared in the previous Preparation Example <NUM> as a dopant, with the weight ratio of the host and the dopant being <NUM>:<NUM>, was spin coated and heat treated at <NUM> for <NUM> minutes to form a hole injection layer having a thickness of <NUM>Å. A <NUM> wt% toluene solution of Compound a-NPD below was spin-coated on the hole injection layer and heat-treated at <NUM> for <NUM> minutes to form a hole transport layer having a thickness of <NUM>Å.

Subsequently, the result was transferred to a vacuum depositor, and then Compound A below and Compound B below were vacuum-deposited in a weight ratio of <NUM>:<NUM> on the hole transport layer to form a light emitting layer having a thickness of <NUM>Å. Compound C was vacuum deposited on the light emitting layer to form an electron injection and transport layer having a thickness of <NUM>Å. LiF and aluminum were sequentially deposited to have a thickness of <NUM>Å and <NUM>,<NUM>Å, respectively, on the electron injection and transport layer, thereby forming a cathode. <CHM>
<CHM>.

In the above-mentioned processes, the deposition rates of the organic materials were maintained at <NUM> to <NUM>Å/sec, the deposition rates of the LiF and the aluminum of the cathode were maintained at <NUM>Å /sec and <NUM>Å /sec, respectively, and the degree of vacuum during the deposition was maintained at <NUM>×<NUM>-<NUM> to <NUM>×<NUM>-<NUM> torr.

The organic light emitting devices were manufactured in the same manner as in Experimental Example <NUM>, except that the compounds shown in Table <NUM> below were used during the formation of the hole injection layer.

The organic light emitting devices were manufactured in the same manner as in Experimental Example <NUM>, except that the compounds shown in Table <NUM> below were used during the formation of the hole injection layer. Compounds CE1, CE2, and CE3 in Table <NUM> are as follows. <CHM>
<CHM>
<CHM>.

For the organic light emitting devices manufactured in the Experimental Examples and Comparative Experimental Examples, the driving voltage, luminous efficiency, power efficiency, external quantum efficiency (QE), luminance, and color coordinates were measured at a current density of <NUM> mA/cm<NUM>, and the results are shown in Table <NUM> below. The external quantum efficiency was determined by (number of photons emitted)/(number of charge carriers injected), and the color coordinates are x and y coordinates based no C. E chromaticity diagram (Commission Internationale de L'Eclairage, <NUM>).

Claim 1:
A compound represented by the following Chemical Formula <NUM>:
<CHM>
wherein
L is substituted or unsubstituted C<NUM>-<NUM> arylene, or substituted or unsubstituted C<NUM>-<NUM> heteroarylene containing any one or more heteroatoms selected from N, O and S;
L<NUM> and L<NUM> are each independently a single bond or methylene;
X<NUM> and X<NUM> are each independently a photocurable group or a thermosetting group independently represented by -L"-R", wherein L" is a single bond, -O-, -S-, - CH<NUM>-, -CH<NUM>O-, -OCH<NUM>-, or -CH<NUM>OCH<NUM>-, and R" is any one of the following:
<CHM>
<CHM>
<CHM>
R'<NUM> to R'<NUM> and R"<NUM> to R"<NUM> are each independently hydrogen, deuterium, substituted or unsubstituted C<NUM>-<NUM> alkyl, substituted or unsubstituted C<NUM>-<NUM> alkoxy, substituted or unsubstituted C<NUM>-<NUM> aryl, or substituted or unsubstituted C<NUM>-<NUM> heteroaryl containing any one or more heteroatoms selected from N, O and S;
n1 to n3 and m1 to m3 are each independently an integer of <NUM> to <NUM>; and
Ar<NUM> and Ar<NUM> are each independently a substituent group represented by the following Chemical Formula <NUM>:
<CHM>
wherein
each R<NUM> is independently a halogen;
each R<NUM> is independently hydrogen, deuterium, or C<NUM>-<NUM>alkyl; and
n is an integer of <NUM> to <NUM>, and m is <NUM> or <NUM>, provided that n+m is <NUM> or less.