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.

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.

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.

Organic electroluminescent compounds which may be used in organic light emitting devices are further disclosed in <CIT>, <CIT>, <CIT>, <CIT> and <CIT>.

According to an aspect of the present disclosure, there is provided a compound represented by the following Chemical Formula <NUM>:
<CHM>
wherein 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 a light emitting layer that is provided between the first electrode and the second electrode, wherein the light emitting layer includes the compound represented by Chemical Formula <NUM>.

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

As used herein, the notation
<CHM>
and <IMG> mean a bond linked to another substituent group, the ph means a phenyl group, and the Boc means tert-butyloxycarbonyl protecting 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 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 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 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 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>-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 biphenylyl group, a terphenylyl group or the like as the monocyclic aryl group, but is not limited thereto. The polycyclic aryl group includes a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, a benzofluorenyl 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 addition, the benzofluorenyl group may also be substituted in the same manner as the fluorenyl group, or two substituents may be linked with each other to form a spiro structure.

In the present disclosure, a heteroaryl group is a heteroaryl group 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 group 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 aryl silyl 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 group in the heteroarylamine group may be applied to the above-mentioned description of the heteroaryl group. 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 group can be applied except that the heteroarylene is a divalent group.

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

The compound represented by Chemical Formula <NUM> has a diamine compound structure in which amino groups are substituted on both sides of a core where two benzo[g]indole structures are fused by a benzene ring. In particular, the compound represented by Chemical Formula <NUM> not only can be easily synthesized, but also can exhibit high solubility in an organic solvent used in the solution process, as compared to a diamine compound having a carbazolo[<NUM>,<NUM>-c]carbazole core, like a compound represented by the following Chemical Formula X1. Furthermore, the organic light emitting device employing the compound represented by Chemical Formula <NUM> as a dopant of the light emitting layer can simultaneously improve the light emitting efficiency and lifetime characteristics, as compared to the organic light emitting device employing the compound represented by the following Chemical Formula X1 as a dopant. <CHM>
wherein in Chemical Formula X1,
the description of each substituent group is as defined in Chemical Formula <NUM>.

In particular, the compound represented by Chemical Formula <NUM> has high solubility in an organic solvent used in a solution process, for example, an organic solvent such as cyclohexanone, and thus is suitable for use in a large-area solution process such as an inkjet coating method using a solvent with a high boiling point.

Moreover, the compound represented by Chemical Formula <NUM> has a structure in which an amino group is linked to any one of the carbons *<NUM> to *<NUM> and any one of the carbons *<NUM>' to *<NUM>' of the core described below. An organic light emitting device employing such a compound as a dopant of the light emitting layer has the same core as described in the present disclosure like the compound represented by the following Chemical Formula X2, but can exhibit excellent light emitting efficiency and lifetime characteristics, even as compared to an organic light emitting device employing, as a dopant, a compound whose substitution positions of two amino groups are different from those described herein. <CHM>
<CHM>
wherein in Chemical Formula X2,
the description of each substituent group is as defined in Chemical Formula <NUM>.

Meanwhile, the compound may be represented by the following Chemical Formula <NUM>':
<CHM>
wherein in Chemical Formula <NUM>',
L<NUM> to L<NUM>, Ar<NUM> to Ar<NUM>, R<NUM> to R<NUM>, a, b and c are as defined in Chemical Formula <NUM>.

Specifically, the compound represented by Chemical Formula <NUM>' may be represented by any one of the following Chemical Formulas <NUM>-<NUM> to <NUM>-<NUM>, depending on the position where two benzo[g]indole structures are fused by a benzene ring:
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
wherein in Chemical Formulas <NUM>-<NUM> to <NUM>-<NUM>,
L<NUM> to L<NUM>, Ar<NUM> to Ar<NUM>, R<NUM> to R<NUM>, a, b and c are as defined in Chemical Formula <NUM>.

Specifically, in Chemical Formula <NUM>, L<NUM> to L<NUM> are each independently a single bond; or a C<NUM>-<NUM> arylene which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a C<NUM>-<NUM> alkyl and a C<NUM>-<NUM> aryl.

Specifically, in Chemical Formula <NUM>, L<NUM> to L<NUM> may be each independently a single bond, phenylene, biphenyldiyl, naphthylene, or <NUM>,<NUM>-di(C<NUM>-<NUM> alkyl)fluorenylene.

More specifically, each L<NUM> is independently a single bond, biphenyldiyl, naphthylene, or <NUM>,<NUM>-dimethylfluorenylene, and
L<NUM> and L<NUM> are each independently a single bond, phenylene, naphthylene, <NUM>,<NUM>-dimethylfluorenylene, or <NUM>,<NUM>-dihexylfluorenylene.

For example, each L<NUM> is independently a single bond, or any one selected from the group consisting of:
<CHM>.

L<NUM> and L<NUM> may be each independently a single bond, or any one selected from the group consisting of:
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>.

Further, in Chemical Formula <NUM>, Ar<NUM> to Ar<NUM> are each independently a C<NUM>-<NUM> aryl which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a C<NUM>-<NUM> alkyl, a C<NUM>-<NUM> aryl, a Si(C<NUM>-<NUM> alkyl)<NUM> and a Si(C<NUM>-<NUM> aryl)<NUM>; or a C<NUM>-<NUM> heteroaryl containing <NUM> or <NUM> heteroatoms selected among N, O and S which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a C<NUM>-<NUM> alkyl, a C<NUM>-<NUM> aryl, a Si(C<NUM>-<NUM> alkyl)<NUM> and a Si(C<NUM>-<NUM> aryl)<NUM>.

Specifically, Ar<NUM> to Ar<NUM> each may be independently phenyl, naphthyl, fluorenyl, benzofluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofuranyl, or benzothiophenyl;
wherein, Ar<NUM> to Ar<NUM> are unsubstituted or substituted with one to five substituents selected from the group consisting of deuterium, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, phenyl, or Si(phenyl)<NUM>.

For example, each Ar<NUM> may be independently any one selected from the group consisting of:
<CHM>
<CHM>
wherein,
Z<NUM> and Z<NUM> are each independently methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, or phenyl.

Further, for example, Ar<NUM> and Ar<NUM> may be each independently any one selected from the group consisting of:
<CHM>
<CHM>
<CHM>
wherein,
Z<NUM> and Z<NUM> are each independently methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, or phenyl.

Also, in Chemical Formula <NUM>, one of Ar<NUM> and Ar<NUM> may be phenyl, phenyl substituted with a C<NUM>-<NUM> alkyl, naphthyl, or benzofuranyl.

Further, in Chemical Formula <NUM>, R<NUM> to R<NUM> are each independently hydrogen; deuterium; halogen; cyano; a C<NUM>-<NUM> alkyl; or a C<NUM>-<NUM> aryl. In this case, a, which means the number of R<NUM>, is <NUM>, <NUM>, <NUM>, <NUM>, <NUM> or <NUM>, b, which means the number of R<NUM>, is <NUM>, <NUM>, <NUM>, <NUM>, <NUM> or <NUM>, and c, which means the number of R<NUM>, is <NUM>, <NUM>, or <NUM>.

Further, in Chemical Formula <NUM>,
L<NUM> may be identical to each other, L<NUM> may be identical to each other, L<NUM> may be identical to each other, Ar<NUM> may be identical to each other, Ar<NUM> may be identical to each other, Ar<NUM> may be identical to each other, R<NUM> may be identical to each other, R<NUM> may be identical to each other, R<NUM> may be identical to each other, a may be identical to each other, b may be identical to each other, and c may be identical to each other.

For example, L<NUM> may be identical to each other, L<NUM> may be identical to each other, L<NUM> may be identical to each other, Ar<NUM> may be identical to each other, Ar<NUM> may be identical to each other, Ar<NUM> may be identical to each other; or L<NUM> and L<NUM> are identical to or different from each other, L<NUM> may be different, Ar<NUM> may be different, Ar<NUM> may be identical to each other, and Ar<NUM> may be identical to each other.

In addition, the compound may be represented by any one of the following Chemical Formulas <NUM>-<NUM>-<NUM> to <NUM>-<NUM>-<NUM>:
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
wherein in Chemical Formulas <NUM>-<NUM>-<NUM> to <NUM>-<NUM>-<NUM>,.

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>.

Meanwhile, the compound represented by Chemical Formula <NUM> may be prepared, for example, by a preparation method as shown in the following Reaction Scheme <NUM>. <CHM>
<CHM>
wherein in Reaction Scheme <NUM>, each X may be independently halogen, preferably bromo, or chloro, and the definitions of other substituents are the same as described above.

Specifically, the compound represented by Chemical Formula <NUM> is prepared by combining the starting materials SM1 and SM2 through an amine substitution reaction. The amine substitution reaction 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 appropriately modified, and the method for preparing the compound represented by Chemical Formula <NUM> may be further embodied in Preparation Examples described hereinafter.

Meanwhile, 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. Specifically, the compound may be used as a dopant material of the light emitting layer. 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, mesitylene, <NUM>-methylnaphthalene, and <NUM>-methylnaphthalene; 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, methyl-<NUM>-methoxybenzoate and ethylbenzoate; phthalate-based solvents such as dimethyl phthalate, diethyl phthalate, and diphenyl phthalate; 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. Preferably, ethyl benzoate may be used as the solvent.

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

Further, the viscosity of the coating composition is preferably <NUM> cP to <NUM> cP, and coating is made easy within the above range. Further, in the coating composition, the concentration of the compound according to the present disclosure may be preferably <NUM> wt/v% to <NUM> wt/v%.

Further, the solubility (wt%) of the compound represented by Chemical Formula <NUM> at normal temperature/normal pressure may be <NUM> wt% or more based on the solvent cyclohexanone. Thereby, the coating composition including the compound represented by Chemical Formula <NUM> and the solvent may be used in a solution process.

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 coating composition according to the present disclosure on the anode or on the hole transport layer formed on 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, spraying, 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 from <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 a light emitting layer that is provided between the first electrode and the second electrode, wherein the light emitting layer includes the compound represented by Chemical Formula <NUM>.

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 wherein the first electrode is an anode, and the second electrode is a cathode. 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 wherein the first electrode is a cathode and the second electrode is an anode. 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 using materials and methods known in the art, except that the light emitting layer includes the compound according to the present disclosure, and is manufactured by the above-mentioned method.

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 polymers 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 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. As the hole transport material, the compound represented by Chemical Formula <NUM> may be used, or an arylamine-based organic material, a conductive polymer, a block copolymer in which a conjugate portion and a non-conjugate portion are present together, and the like, but are not limited thereto.

Meanwhile, the organic light emitting device may be provided with an electron inhibition layer between the hole transport layer and the light emitting layer. The electron inhibition layer refers to a layer which is formed on the hole transport layer, and preferably, is provided in contact with the light emitting layer, and thus serves to control hole mobility, to prevent excessive movement of electrons, and to increase the probability of hole-electron bonding, thereby improving the efficiency of the organic light emitting device. The electron inhibition layer includes an electron blocking material, and as an example of such an electron blocking material, a compound represented by the Chemical Formula <NUM> may be used, or an arylamine-based organic material or the like may be used, but is not limited thereto.

The light emitting layer may include a host material and a dopant material. As the dopant material, the above-mentioned compound represented by Chemical Formula <NUM> can be used. Also, 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.

Meanwhile, the organic light emitting device may be provided with a hole blocking layer between the light emitting layer and the electron transport layer. The hole blocking layer refers to a layer which is formed on the light emitting layer, and preferably, is provided in contact with the light emitting layer, and thus severs to control electron mobility, to prevent excessive movement of holes, and to increase the probability of hole-electron bonding, thereby improving the efficiency of the organic light emitting device. The hole blocking layer includes a hole blocking material, and as an example of such hole blocking material, a compound into which an electron-withdrawing group is introduced, such as azine derivatives including triazine; triazole derivatives; oxadiazole derivatives; phenanthroline derivatives; phosphine oxide derivatives can be used, 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 hole blocking 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, it may be used together with 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 electron injection and transport layer may also be formed as a separate layer such as an electron injection layer and an electron transport layer. In such a case, the electron transport layer is formed on the light emitting layer or the hole blocking layer, and the above-mentioned electron injection and transport material may be used as the electron transport material included in the electron transport layer. In addition, the electron injection layer is formed on the electron transport layer, and examples of the electron injection material included in the electron injection layer include LiF, NaCl, CsF, Li<NUM>O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, 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.

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> and the organic light emitting device including 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.

Compound <NUM>-a (<NUM> eq. ), Compound <NUM>-b (<NUM> eq. ), Cs<NUM>CO<NUM> (<NUM> eq. ) and P(t-Bu)<NUM> HBF<NUM> (<NUM> mol%) were placed in a round bottom flask filled with N<NUM> (g), and dissolved in anhydrous toluene. After raising the bath temperature to <NUM>, Pd(OAc)<NUM> (<NUM> mol%) was added dropwise thereto, and the mixture was stirred for <NUM> hours. After the reaction, the reaction mixture was washed with dichloromethane and water, the organic layer was separated, water was removed with MgSO<NUM>, and passed through a celite-silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to obtain Intermediate Compound <NUM>-c (yield: <NUM>%).

Compound <NUM>-d (<NUM> eq. ), Compound <NUM>-c (<NUM> eq. ), Cs2CO3 (<NUM> eq. ) and P(t-Bu)<NUM>•HBF<NUM> (<NUM> mol%) were placed in a round bottom flask filled with N<NUM> (g), and dissolved in anhydrous toluene. After raising the bath temperature to <NUM>, Pd(OAc)<NUM> (<NUM> mol%) was added dropwise thereto, and the mixture was stirred overnight. After the reaction, the reaction mixture was washed with dichloromethane and water, the organic layer was separated, water was removed with MgSO<NUM>, and passed through a celite-silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to obtain Intermediate Compound <NUM>-e (yield: <NUM>%).

Compound <NUM>-e(<NUM> eq. ) and ZnCl<NUM> (<NUM> eq. ) were placed in a round bottom flask filled with N<NUM> (g), and dissolved in anhydrous <NUM>,<NUM>-dioxane. After raising the bath temperature to <NUM>, the mixture was stirred for <NUM> hour. After the reaction, saturated aqueous Na<NUM>CO<NUM> was added dropwise to terminate the reaction, and the reaction mixture was washed with dichloromethane and water, the organic layer was separated. Water was removed with MgSO<NUM>, and passed through a celite-silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to obtain Intermediate Compound <NUM>-f (yield: <NUM>%).

Compound <NUM>-f (<NUM> eq. ) and DDQ (<NUM>,<NUM>-dichloro-<NUM>,<NUM>-dicyano-p-benzoquinone, <NUM> eq. ) were placed in a round bottom flask filled with N<NUM> (g), and dissolved in anhydrous benzene. The reaction solution was stirred at room temperature for <NUM> hours. After the reaction, the solvent was removed under reduced pressure, and K<NUM>CO<NUM> (<NUM> eq. ), MeOH, and H<NUM>O were added dropwise to the reaction mixture. After raising the bath temperature to <NUM>, the reaction solution was stirred for <NUM> minutes. After the reaction, the precipitate was washed with MeOH and H<NUM>O and filtered to obtain a filter cake. A sufficiently dried filter cake was added to <NUM>,<NUM>-dichlorobenzene and dissolved under heating. The dissolved reaction product was passed through a celite-silica pad. An excess of n-hexane was added dropwise to the passed solution to precipitate the product. The precipitate was washed with n-hexane and MeOH and filtered to obtain a filter cake, which was sufficiently dried to synthesize Compound <NUM>-g (yield: <NUM>%).

Compound <NUM>-g (<NUM> eq. ) and NaOt-Bu (<NUM> eq. ) were placed in a round bottom flask and dissolved in anhydrous PhMe (<NUM>). Compound <NUM>-h (<NUM> eq. ) was added dropwise to the reaction solution. Pd(P(t-Bu)<NUM>)<NUM> (<NUM> mol%) was added dropwise to the reaction solution under a bath temperature of <NUM>, and the mixture was stirred for <NUM> hours. After the reaction, the reaction mixture was washed with dichloromethane and water, the organic layer was separated, water was removed with MgSO<NUM>, and passed through a celite-silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to obtain Intermediate Compound <NUM>-i (yield: <NUM>%).

Compound <NUM>-j (<NUM> eq. ), Compound <NUM>-k (<NUM> eq. ) and NaOt-Bu (<NUM> eq. ) were placed in a round bottom flask and dissolved in anhydrous toluene. After raising the bath temperature to <NUM>, Pd((t-Bu)<NUM>P)<NUM> (<NUM> mol%) was added dropwise thereto, and the mixture was stirred for <NUM> hours. After the reaction, the reaction mixture was washed with dichloromethane and water, the organic layer was separated, water was removed with MgSO<NUM>, and passed through a celite-silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to obtain Intermediate Compound <NUM>-I (yield: <NUM>%).

Compound <NUM>-i (<NUM> eq. ), Compound <NUM>-I (<NUM> eq. ), P(t-Bu)<NUM>HBF<NUM> (<NUM> mol%), and NaOt-Bu (<NUM>. ) were placed in a round bottom flask and dissolved in anhydrous PhMe (<NUM>). Pd<NUM>(dba)<NUM> (<NUM> mol%) was added dropwise to the reaction solution under a bath temperature of <NUM>, and the mixture was stirred overnight. After the reaction, the reaction mixture was stirred and then cooled to room temperature. An excess of n-hexane was added dropwise to the reaction mixture to precipitate the product. The precipitate was washed with MeOH and H<NUM>O and filtered to obtain a filter cake. A sufficiently dried filter cake was added to <NUM>,<NUM>-dichlorobenzene and dissolved under heating. The dissolved reaction product was passed through a celite-silica pad. An excess of n-hexane was added dropwise to the passed solution to precipitate the product. The precipitate was washed with n-hexane and MeOH and filtered to obtain a filter cake, which was sufficiently dried to prepare Compound <NUM> (yield: <NUM>%).

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

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

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

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

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

Compound <NUM>-a (<NUM> eq. ), Compound <NUM>-b (<NUM> eq. ) and NaOt-Bu (<NUM> eq. ) were placed in a round bottom flask and dissolved in anhydrous toluene. After raising the bath temperature to <NUM>, Pd((t-Bu)<NUM>P)<NUM> (<NUM> mol%) was added dropwise thereto, and the mixture was stirred for <NUM> hours. After the reaction, the reaction mixture was washed with dichloromethane and water, the organic layer was separated, water was removed with MgSO<NUM>, and passed through a celite-silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to obtain Intermediate Compound <NUM>-c (yield: <NUM>%).

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

Compound <NUM>-a (<NUM> eq. ), Compound <NUM>-b (<NUM> eq. ) and (tetrakis(triphenylphosphine)palladium(<NUM>))(Pd(PPh<NUM>)<NUM>, <NUM> mol%) were placed in a round bottom flask and dissolved in anhydrous toluene (<NUM>). After raising the bath temperature to <NUM>, Cs<NUM>CO<NUM> (<NUM> eq. ) dissolved in H<NUM>O was added dropwise to the reaction solution. Then, the mixture was stirred for <NUM> hours under a bath temperature of <NUM>. After the reaction, the reaction mixture was washed with dichloromethane and water, the organic layer was separated, water was removed with MgSO<NUM>, and passed through a celite-silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to obtain Intermediate Compound <NUM>-c (yield: <NUM>%).

Compound <NUM>-c (<NUM> eq. ), Compound <NUM>-d (<NUM> eq. ) and NaOt-Bu (<NUM> eq. ) were placed in a round bottom flask and dissolved in anhydrous toluene. After raising the bath temperature to <NUM>, Pd((t-Bu)<NUM>P)<NUM> (<NUM> mol%) was added dropwise to the reaction solution, and the mixture was stirred for <NUM> hours. After the reaction, the reaction mixture was washed with dichloromethane and water, the organic layer was separated, water was removed with MgSO<NUM>, and passed through a celite-silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to obtain Intermediate Compound <NUM>-e (yield: <NUM>%).

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

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

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

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

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

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

Compound F-a (<NUM> eq. ) was placed in a round bottom flask and dissolved in anhydrous CH<NUM>Cl<NUM> (<NUM>). Pyridine (<NUM> eq. ) was added dropwise to the reaction solution, the bath temperature was lowered from room temperature to <NUM>, and the mixture was stirred. Trifluoromethanesulfonic anhydride (Tf<NUM>, <NUM> eq. ) was slowly added dropwise using a dropping funnel for <NUM> minutes, the bath temperature was raised to room temperature, and the mixture was stirred for <NUM> hours. After the reaction, the reaction mixture was washed with dichloromethane and water, the organic layer was separated, water was removed with MgSO<NUM>, and passed through a celite-silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to obtain Intermediate Compound F-b (yield: <NUM>%). m/z [M+H]+= <NUM>.

Compound F-b (<NUM> eq. ), bis(pinacolato)diborane (B<NUM>pin<NUM>, <NUM> eq. ), and KOAc (<NUM> eq. ) were placed in a round bottom flask and dissolved in anhydrous dioxane (<NUM>). After raising the bath temperature from room temperature to <NUM>, (<NUM>,<NUM>'-bis(diethylphosphino)ferrocene)palladium(II) dichloride (Pd(dppf)Cl<NUM>, <NUM> mol%) was added dropwise to the reaction solution, and the mixture was stirred for <NUM> hours. After the reaction, the reaction mixture was washed with dichloromethane and water, the organic layer was separated, water was removed with MgSO<NUM>, and passed through a celite-silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to obtain Intermediate Compound F-c (yield: <NUM>%).

Compound F-c (<NUM> eq. ), Compound F-d (<NUM> eq. ), and (tetrakis(triphenylphosphine)palladium(<NUM>)) (Pd(PPh<NUM>)<NUM>, <NUM> mol%) were placed in a round bottom flask and dissolved in anhydrous PhMe (toluene, <NUM>). After raising the bath temperature to <NUM>, Cs<NUM>CO<NUM> (<NUM> eq. ) dissolved in H<NUM>O was added dropwise to the reaction solution. Then, the mixture was stirred overnight under a bath temperature of <NUM>. After the reaction, the reaction mixture was washed with dichloromethane and water, the organic layer was separated, water was removed with MgSO<NUM>, and passed through a celite-silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to obtain Intermediate Compound F-e (yield: <NUM>%).

Compound F-e (<NUM> eq. ) and PPh<NUM> (<NUM> eq. ) were placed in a round bottom flask and dissolved in anhydrous <NUM>,<NUM>-dichlorobenzene (<NUM>). The mixture was stirred overnight under a bath temperature of <NUM>. After the reaction, the reaction mixture was stirred and then cooled to room temperature. Then, the reaction mixture was washed with dichloromethane and water, the organic layer was separated, water was removed with MgSO<NUM>, and passed through a celite-silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to obtain Intermediate Compound F-f (yield: <NUM>%).

Compound F-f (<NUM> eq. ) and sodium tert-butoxide (NaOt-Bu, <NUM> eq. ) were placed in a round bottom flask and dissolved in anhydrous PhMe(<NUM>). Then, Compound F-g (<NUM> eq. ) was added dropwise to the reaction solution. Next, bis(tri-tert-butylphosphine)palladium(<NUM>)(Pd(P(t-Bu)<NUM>)<NUM>, <NUM> mol%) was added dropwise to the reaction mixture under a bath temperature of <NUM>, and the mixture was stirred for <NUM> hours. After the reaction, the reaction mixture was washed with dichloromethane and water, the organic layer was separated, water was removed with MgSO<NUM>, and passed through a celite-silica pad. The passed solution was concentrated under reduced pressure, and then purified by column chromatography to obtain Intermediate Compound F-h (yield: <NUM>%).

Compound F-h (<NUM> eq. ), Compound <NUM>-I (<NUM> eq. ), P(t-Bu)<NUM>HBF<NUM> (<NUM> mol%), and NaOt-Bu (<NUM> eq. ) were placed in a round bottom flask and dissolved in anhydrous PhMe (<NUM>). Pd<NUM>(dba)<NUM> (<NUM> mol%) was added dropwise to the reaction solution under a bath temperature of <NUM>, and the mixture was stirred overnight. After the reaction, the reaction mixture was stirred and then cooled to room temperature. An excess of n-hexane was added dropwise to the reaction product to precipitate the product. The precipitate was washed with MeOH and H<NUM>O and filtered to obtain a filter cake. A sufficiently dried filter cake was added to <NUM>,<NUM>-dichlorobenzene and dissolved under heating. The dissolved reaction product was passed through a celite-silica pad. An excess of n-hexane was added dropwise to the passed solution to precipitate the product. The precipitate was washed with n-hexane and MeOH and filtered to obtain a filter cake, which was sufficiently dried to synthesize Comparative Compound F (yield: <NUM>%).

Compound G (yield: <NUM>%) was prepared in the same manner as in the synthesis of Comparative Compound F, except that Compound G-a was used instead of Compound <NUM>-I. m/z [M+H]+= <NUM>.

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

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

In order to confirm the solubility in the solvent used in the solution process of the compounds prepared in the Preparation Examples and the comparative compounds, each of them was dissolved in the solvent cyclohexanone (CHON) under normal temperature/pressure conditions, and it was confirmed whether <NUM> wt% or more was dissolved.

As shown in Table <NUM>, it was confirmed that unlike the Comparative Compound I, the compounds included in Chemical Formula <NUM> exhibited excellent solubility in cyclohexanone, which is a solvent used in a solution process of an organic light emitting device.

A glass substrate thinly coated with indium tin oxide (ITO) to have a thickness of <NUM>Å was put into distilled water in which a detergent was dissolved, and ultrasonically washed. In this case, a product manufactured by Fischer Co. , was used as the detergent, and distilled water twice filtered using a filter manufactured by Millipore Co. , was used as the distilled water. After the ITO was washed for <NUM> minutes, ultrasonic washing was conducted twice repeatedly using distilled water for <NUM> minutes. After the washing using distilled water was completed, ultrasonic washing was conducted using isopropyl, and acetone solvents, and drying was conducted, and then the substrate was cleaned for <NUM> minutes, and then transferred to a glove box.

A coating composition, in which the following Compound B and the following Compound C (weight ratio of <NUM>:<NUM>) were dissolved in <NUM> wt/v% cyclohexanone, 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 Compound A (Mn: <NUM>,<NUM>; Mw: <NUM>,<NUM>; measured by gel permeation chromatography (GPC) on Agilent <NUM> series, relative to PC standards) was dissolved in <NUM> wt/v% toluene, 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 Compound <NUM> prepared in Preparation Example <NUM> and the following Compound D (weight ratio of <NUM>:<NUM>) were dissolved in <NUM> wt/v% cyclohexanone, 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 being transferred to a vacuum depositor, the following Compound E was vacuum-deposited to a thickness of <NUM>Å on the light emitting layer to form an electron injection and transport layer.

LiF and aluminum were sequentially deposited to have a thickness of <NUM>Å and <NUM>Å, respectively, on the electron injection and transport layer, thereby forming 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.

An organic light emitting device was manufactured in the same manner as in 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.

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

The structures of the compounds used in the Examples and Comparative Examples are as follows:
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>.

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 Examples and 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, it was confirmed that the organic light emitting devices manufactured by using the compounds of the present disclosure as the dopant of the light emitting layer exhibited excellent characteristics in terms of conversion efficiency and lifetime, as compared with the organic light emitting devices manufactured by using Compound F, Compound G or Compound H of Comparative Examples as the dopant of the light emitting layer.

Claim 1:
A compound represented by the following Chemical Formula <NUM>:
<CHM>
wherein in Chemical Formula <NUM>,
A is a benzene ring fused with two adjacent pentagonal rings,
L<NUM> to L<NUM> are each independently a single bond; or a C<NUM>-<NUM> arylene which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a C<NUM>-<NUM> alkyl and a C<NUM>-<NUM> aryl,
Ar<NUM> to Ar<NUM> are each independently a C<NUM>-<NUM> aryl which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a C<NUM>-<NUM> alkyl, a C<NUM>-<NUM> aryl, a Si(C<NUM>-<NUM> alkyl)<NUM> and a Si(C<NUM>-<NUM> aryl)<NUM>; or a C<NUM>-<NUM> heteroaryl containing <NUM> or <NUM> heteroatoms selected among N, O and S which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a C<NUM>-<NUM> alkyl, a C<NUM>-<NUM> aryl, a Si(C<NUM>-<NUM> alkyl)<NUM> and a Si(C<NUM>-<NUM> aryl)<NUM>,
R<NUM> to R<NUM> are each independently hydrogen; deuterium; halogen; cyano; a C<NUM>-<NUM> alkyl; or a C<NUM>-<NUM> aryl,
a and b are each independently an integer of <NUM> to <NUM>, and
c is an integer of <NUM> to <NUM>.