Patent Description:
The present disclosure relates to an organic light emitting device.

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.

According to the claimed invention, there is provided an organic light emitting device including.

The above-described organic light emitting device controls the compound included in the light emitting layer and the electron transport layer, thereby improving efficiency, low driving voltage, and/or lifespan of the organic light emitting device.

As used herein, the notation
<CHM>
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 nitrile group; a nitro group; a hydroxyl 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 heterocyclic group containing at least one of N, O and S atoms, or being unsubstituted or substituted with a substituent in 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 group having the following structural formulae, 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 is 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 formulae, 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 formulae, 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, a boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron 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>-dimethylpropyl, 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 monocyclic aryl group includes a phenyl group, a biphenyl group, a terphenyl group and the like, but is not limited thereto. The polycyclic aryl group includes a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group or the like, but is not limited thereto.

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

In the present disclosure, a heterocyclic group is a heterocyclic group containing at least one heteroatom of O, N, Si and S as a heterogeneous element, and the carbon number thereof is not particularly limited, but is preferably <NUM> to <NUM>. Examples of the heterocyclic group include 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, and the arylamine 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 apply the aforementioned description of the heterocyclic 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 heterocyclic 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 heterocycle is not a monovalent group but formed by combining two substituent groups.

In the present disclosure, there is provided an organic light emitting device including an anode; a hole transport layer; a light emitting layer; an electron transport layer, an electron injection layer, or an electron transport and injection layer; and a cathode, wherein the light emitting layer includes a compound represented by the Chemical Formula <NUM>, and the electron transport layer, the electron injection layer, or the electron transport and injection layer includes at least one of the compound represented by the Chemical Formula <NUM> and the compound represented by the Chemical Formula <NUM>.

The organic light emitting device according to the present disclosure controls the compound included in the light emitting layer and the compound included in the electron transport layer, the electron injection layer, or the electron transport and injection layer, thereby improving efficiency, low driving voltage, and/or lifespan of the organic light emitting device.

Hereinafter, the present invention will be described in detail for each configuration.

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 organic light emitting device according to the present disclosure may include a hole injection layer between the anode and the hole transport layer, if necessary.

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 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.

In addition, the hole transport layer is a layer that receives holes from an anode or a hole injection layer formed on the anode and transports the holes to the light emitting layer. The hole transport material is suitably a material having large mobility to the holes, which may receive holes from the anode or the hole injection layer and transfer the holes to the light emitting layer. Specific examples thereof include an arylamine-based organic material, a conductive 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.

The organic light emitting device according to the present disclosure may include an electron blocking layer between a hole transport layer and a light emitting layer, if necessary. The electron blocking layer is a layer which is formed on the hole transport layer, is preferably 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 blocking layer includes an electron blocking material, and an arylamine-based organic material may be used as the electron blocking material, but is not limited thereto.

The light emitting material included in the light emitting layer is suitably a material capable of emitting light in a visible ray region by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, to combine them, and having good quantum efficiency to fluorescence or phosphorescence. The light emitting layer may include a host material and a dopant material, and the compound represented by the Chemical Formula <NUM> is included in the light emitting layer according to the claimed invention. The compound represented by the Chemical Formula <NUM> may be included as a host material.

Preferably, L<NUM> is a direct bond, phenylene, biphenylene, or naphthylene; and the phenylene, biphenylene, or naphthylene is each independently unsubstituted or substituted with deuterium.

Preferably, Ar<NUM> is phenyl, biphenylyl, naphthyl, or phenanthrenyl; and the phenyl, biphenylyl, naphthyl, or phenanthrenyl is each independently unsubstituted or substituted with deuterium.

Preferably, R<NUM> to R<NUM> are each independently hydrogen, deuterium, phenyl, or naphthyl, or two adjacent substituents of R<NUM> to R<NUM> are combined to form a benzene ring; and the phenyl, naphthyl, or benzene ring is each independently unsubstituted or substituted with deuterium.

Preferably, each R<NUM> is independently hydrogen or deuterium; each R<NUM> or R<NUM> is independently hydrogen, deuterium, phenyl, or naphthyl, or two adjacent substituents of R<NUM> or R<NUM> are combined to form a benzene ring; and the phenyl, naphthyl, or benzene ring is each independently unsubstituted or substituted with deuterium.

Preferably, the compound represented by the Chemical Formula <NUM> contains at least one deuterium.

Representative examples of the compound represented by the 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>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>.

In addition, the present disclosure provides a method for preparing a compound represented by the Chemical Formula <NUM>, as shown in Reaction Scheme <NUM> below.

In the Reaction Scheme <NUM>, Z, L<NUM>, Ar<NUM>, R<NUM> to R<NUM>, n, m, and o are as defined above, and NBS is N-bromosuccinimide.

The above reaction uses a Suzuki coupling reaction, and may be more specifically described in Examples described below.

The organic light emitting device according to the present disclosure includes a hole blocking layer between the light emitting layer and the electron transport layer, if necessary. Preferably, the hole blocking layer is in contact with the light emitting layer.

The hole blocking layer serves to improve the efficiency of an organic light emitting device by suppressing holes injected from the anode from being transferred to the cathode without recombination in the light emitting layer. Specific examples of the hole blocking material include an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex, and the like, but are not limited thereto.

The organic light emitting device according to the claimed invention includes an electron transport layer, an electron injection layer, or an electron transport and injection layer between the light emitting layer and the cathode, said electron transport layer, electron injection layer, or electron transport and injection layer comprises at least one of the compound represented by the Chemical Formula <NUM> and the compound represented by Chemical Formula <NUM>.

The electron transport layer is a layer which receives electrons from a cathode or an electron injection layer formed on the cathode and transports the electrons to a light emitting layer, and can suppress the transfer of holes in the light emitting layer. An electron transport material is suitably a material which can receive electrons well from a cathode and transport the electrons to a light emitting layer, and at least one of the compound represented by the Chemical Formula <NUM> and the compound represented by the Chemical Formula <NUM> may be included according to the claimed invention.

The electron injection layer is a layer which injects electrons from an electrode, and the electron injection material is preferably a compound which can transport 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. According to the claimed invention, at least one of the compound represented by the Chemical Formula <NUM> and the compound represented by the Chemical Formula <NUM> may be included in the electron injection layer.

The electron transport and injection layer is a layer capable of simultaneously performing electron transport and electron injection, and may include according to the claimed invention, at least one of the compound represented by the Chemical Formula <NUM> and the compound represented by the Chemical Formula <NUM>.

Preferably, the Chemical Formula <NUM> is represented by the following Chemical Formula <NUM>-<NUM>; and the Chemical Formula <NUM> is represented by the following Chemical Formula <NUM>-<NUM>:
<CHM>
<CHM>
<CHM>
in the Chemical Formula <NUM>-<NUM> or <NUM>-<NUM>, L<NUM>, L<NUM>, Ar<NUM> and Ar<NUM> are as defined above.

Preferably, L<NUM> and L<NUM> are each independently a direct bond, phenylene, or biphenyldiyl.

Preferably, Ar<NUM> and Ar<NUM> are each independently any one selected from the group consisting of:
<CHM>
<CHM>
in the above group, R<NUM> is as defined above.

Preferably, each R<NUM> is independently hydrogen, deuterium, methyl, tert-butyl, phenyl, biphenylyl, terphenylyl, naphthyl, pyridinyl, furanyl, or thiophenyl, or two adjacent Ras are combined to form a benzene ring; and the phenyl, biphenylyl, terphenylyl, naphthyl, pyridinyl, furanyl, or thiophenyl is each independently unsubstituted or substituted with deuterium, methyl, or tert-butyl.

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

Representative examples of the compound represented by the Chemical Formula <NUM> and the compound represented by the 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>.

In addition, the present disclosure provides a method for preparing a compound represented by the Chemical Formula <NUM> or a compound represented by the Chemical Formula <NUM>, as shown in Reaction Schemes <NUM> to <NUM> below. <CHM>
<CHM>
<CHM>
<CHM>
<CHM>.

In the Reaction Schemes <NUM> to <NUM>, each L is independently L<NUM> or L<NUM>; each Ar is independently Ar<NUM> or Ar<NUM>; each R is independently any one of R<NUM> to R<NUM>; and each p is independently any one of p1 to p4. In addition, L<NUM>, L<NUM>, Ar<NUM>, Ar<NUM>, R<NUM> to R<NUM>, and p1 to p4 are as defined above, and X is halogen, preferably bromo, or chloro.

In addition, the electron transport layer may further include a metal complex compound.

In addition, the electron injection layer may further include a metal complex compound.

A structure of the organic light emitting device according to the present disclosure is illustrated in <FIG> shows an example of an organic light emitting device including a substrate <NUM>, an anode <NUM>, a hole transport layer <NUM>, a light emitting layer <NUM>, an electron transport and injection layer <NUM>, and a cathode <NUM>.

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

The organic light emitting device according to the present disclosure may be manufactured by sequentially laminating the above-described components. In this case, the organic light emitting device may be manufactured by depositing a metal, metal oxides having conductivity, or an alloy thereof on the substrate using a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method to form an anode, forming the above-mentioned respective layers thereon, and then depositing a material that can be used as the cathode thereon. In addition to such a method, the organic light emitting device may be manufactured by sequentially depositing the above-described components from a cathode material to an anode material in the reverse order on a substrate (<CIT>). Further, the light emitting layer may be formed using the host and the dopant by a solution coating method as well as a vacuum deposition method. Herein, the solution coating method means a spin coating, a dip coating, a doctor blading, an inkjet printing, a screen printing, a spray method, a roll coating, or the like, but is not limited thereto.

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

Hereinafter, preferred examples are presented to help the understanding of the present invention. However, these examples are presented for illustrative purposes only, and are not intended to limit the scope of the present disclosure.

B1-A (<NUM>, <NUM> mmol) and B1-B (<NUM>, 60mmol) were added to tetrahydrofuran (<NUM>) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (<NUM>, <NUM> mmol) was dissolved in water (<NUM>), and then added thereto. Thereafter, it was stirred sufficiently, followed by adding tetrakistriphenyl-phosphinopalladium (<NUM>, <NUM> mmol). After <NUM> hour of reaction, cooling was performed to room temperature. Then, the organic layer was separated from the water layer, and then the organic layer was distilled. Then, this was dissolved again in chloroform (<NUM> times, <NUM>), and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to prepare Compound B1 in the form of solid (<NUM>, <NUM> %). MS: [M+H]+ = <NUM>.

Compound B2-A was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme (MS: [M+H]+ = <NUM>).

Structural Formula B2-A (<NUM>, <NUM> mmol) and AlCl<NUM> (<NUM>) were added to C<NUM>D<NUM> (<NUM>) and stirred for <NUM> hours. After completion of the reaction, D<NUM>O (<NUM>) was added, and stirred for <NUM> minutes, followed by adding trimethylamine (<NUM>) dropwise. The reaction solution was transferred to a separatory funnel, and extracted with water and toluene. The extract was dried with anhydrous magnesium sulfate (MgSO<NUM>) and recrystallized with ethyl acetate to obtain Structural Formula B2 (<NUM>, <NUM>%). MS: [M+H]+ = <NUM>.

Compound B3 was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme. MS: [M+H]+ = <NUM>.

Compound B4 was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme. MS: [M+H]+ = <NUM>.

Compound B5 was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme. MS: [M+H]+ = <NUM>.

E1-A (<NUM>, <NUM> mmol) and E1-B (<NUM>, <NUM>. 2mmol) were added to tetrahydrofuran (<NUM>) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (<NUM>, <NUM> mmol) was dissolved in water (<NUM>), and then added thereto. Thereafter, it was stirred sufficiently, followed by adding tetrakistriphenyl-phosphinopalladium (<NUM>, <NUM> mmol). After <NUM> hour of reaction, cooling was performed to room temperature. Then, the organic layer was separated from the water layer, and then the organic layer was distilled. Then, this was dissolved again in chloroform (<NUM> times, <NUM>), and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to prepare Compound E1 in the form of white solid (<NUM>, <NUM> %). MS: [M+H]+ = <NUM>.

Compound E2 was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme. MS: [M+H]+ = <NUM>.

Compound E3 was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme. MS: [M+H]+ = <NUM>.

Compound E4 was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme. MS: [M+H]+ = <NUM>.

Compound E5 was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme. MS: [M+H]+ = <NUM>.

Compound E6 was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme. MS: [M+H]+ = <NUM>.

Compound E7 was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme. MS: [M+H]+ = <NUM>.

E8-A (<NUM>, <NUM> mmol) and E8-B (<NUM>, <NUM> mmol) were added to <NUM>,<NUM>-dioxane (<NUM>) under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, tripotassium phosphate (<NUM>, <NUM> mmol) was dissolved in water (<NUM>), and then added thereto. Thereafter, it was stirred sufficiently, followed by adding dibenzylideneacetonepalladium (<NUM>, <NUM> mmol) and tricyclohexylphosphine (<NUM>, <NUM> mmol). After <NUM> hours of reaction, cooling was performed to room temperature, and the resulting solid was filtered. The resulting solid was dissolved again in chloroform (<NUM> times, <NUM>), and washed twice with water. Thereafter, the organic layer was separated, treated with anhydrous magnesium sulfate, stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to prepare Compound E8 in the form of white solid (<NUM>, <NUM>%). MS: [M+H]+ = <NUM>.

Compound E9 was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme. MS: [M+H]+ = <NUM>.

Compound E10 was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme. MS: [M+H]+ = <NUM>.

Compound E11 was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme. MS: [M+H]+ = <NUM>.

Compound E12 was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme. MS: [M+H]+ = <NUM>.

Compound E13 was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme. MS: [M+H]+ = <NUM>.

Compound E14 was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme. MS: [M+H]+ = <NUM>.

Compound E15 was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme. MS: [M+H]+ = <NUM>.

Compound E16 was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme. MS: [M+H]+ = <NUM>.

Compound E17 was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme. MS: [M+H]+ = <NUM>.

Compound E18 was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme. MS: [M+H]+ = <NUM>.

Compound E19 was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme. MS: [M+H]+ = <NUM>.

Compound E20 was prepared in the same manner as in Preparation Example <NUM>-<NUM>, except that each starting material was used as in the above reaction scheme. MS: [M+H]+ = <NUM>.

A glass substrate on which ITO (Indium Tin Oxide) was coated as a thin film to a thickness of <NUM>,<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 distilled water filtered twice using a filter manufactured by Millipore Co. was used as the distilled water. After the ITO was cleaned for <NUM> minutes, ultrasonic cleaning was repeated twice using distilled water for <NUM> minutes. After the cleaning with distilled water was completed, the substrate was ultrasonically cleaned with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned for <NUM> minutes using oxygen plasma and then transferred to a vacuum depositor.

On the prepared ITO transparent electrode, the following Compound HI-A was thermally vacuum-deposited to a thickness of <NUM>Å to form a hole injection layer. On the hole injection layer, hexanitrile hexaazatriphenylene (HAT, 50Å) with the following formula and the following Compound HT-A (<NUM>Å) were sequentially vacuum-deposited to form a hole transport layer.

Then, the following Compounds B1 and BD were vacuum-deposited on the hole transport layer at a weight ratio of <NUM>:<NUM> to a thickness of <NUM>Å to form a light emitting layer.

The Compound E1 and the following Compound LiQ (Lithiumquinolate) were vacuum-deposited on the light emitting layer at a weight ratio of <NUM>:<NUM> to a thickness of <NUM>Å to form an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) and aluminum were sequentially deposited to a thickness of <NUM>Å and <NUM>,<NUM>Å, respectively to form a cathode. <CHM>
<CHM>.

In the above process, the deposition rate of the organic material was maintained at <NUM> to <NUM>Å/sec, the deposition rate of lithium fluoride of the cathode was maintained at <NUM>. 3Å/sec, and the deposition rate of aluminum was maintained at <NUM>Å/sec. In addition, the degree of vacuum during the deposition was maintained at <NUM> × <NUM>-<NUM>to <NUM> × <NUM>-<NUM> torr, thereby manufacturing an organic light emitting device.

An organic light emitting device was manufactured in the same manner as in Experimental Example <NUM>, except that the compound shown in Table <NUM> was used instead of Compound B1 or Compound E1.

An organic light emitting device was manufactured in the same manner as in Experimental Example <NUM>, except that the compound shown in Table <NUM> was used instead of Compound B1 or Compound E1. At this time, Compounds BH-<NUM> to BH-<NUM>, and ET-<NUM> to ET-<NUM> listed in Table <NUM> are as follows. <CHM>
<CHM>
<CHM>
<CHM>
<CHM>
<CHM>.

For the organic light emitting devices, the driving voltage and luminous efficiency were measured at a current density of <NUM> mA/cm<NUM>. In addition, T<NUM>, which is the time taken until the initial luminance decreases to <NUM>% at a current density of <NUM> mA/cm<NUM>, was measured.

As shown in Table <NUM>, the compound represented by the Chemical Formula <NUM> of the claimed invention is used in an organic material layer corresponding to the light emitting layer of an organic light emitting device.

As shown in Table <NUM>, the compound represented by the Chemical Formula <NUM> or <NUM> of the claimed invention is used in an organic material layer capable of simultaneously performing electron injection and electron transport of an organic light emitting device.

When comparing Experimental Examples <NUM> to <NUM> and Comparative Experimental Examples <NUM> to <NUM> of Table <NUM>, it was confirmed that the organic light emitting device including the heterocyclic compound of Chemical Formula <NUM> of the claimed invention had significantly superior efficiency and lifespan than the organic light emitting device including a compound in which only an aryl group is substituted in the light emitting layer.

When comparing Experimental Examples <NUM> to <NUM> and Comparative Experimental Examples <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM>-<NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM> of Table <NUM>, it was confirmed that the organic light emitting device including the heterocyclic compound of Chemical Formula <NUM> or <NUM> of the claimed invention had significantly superior efficiency and lifespan than the organic light emitting device including a compound in which a phenyl group less than quarterphenyl is substituted between Ar<NUM> and Ar<NUM>.

When comparing Experimental Examples <NUM> to <NUM> and Comparative Experimental Examples <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM>, <NUM> to <NUM> of Table <NUM>, it was confirmed that the organic light emitting device including the heterocyclic compound of Chemical Formula <NUM> or <NUM> of the claimed invention had significantly superior efficiency and lifespan than the organic light emitting device including a compound in which quaterphenyl is substituted at a different substitution position from the present disclosure.

When comparing Experimental Examples <NUM> to <NUM> and Comparative Experimental Examples <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> of Table <NUM>, it was confirmed that the organic light emitting device including the heterocyclic compound of Chemical Formula <NUM> or <NUM> of the claimed invention had significantly superior efficiency and lifespan than the organic light emitting device including a compound in which naphthalene is substituted between Ar<NUM> and Ar<NUM>.

When comparing Experimental Examples <NUM> to <NUM> and Comparative Experimental Examples <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> of Table <NUM>, it was confirmed that the organic light emitting device including the heterocyclic compound of Chemical Formula <NUM> or <NUM> of the claimed invention had significantly superior efficiency and lifespan than the organic light emitting device including a compound in which heteroaryl is additionally substituted to quaterphenylene.

Claim 1:
An organic light emitting device comprising:
an anode (<NUM>);
a hole transport layer (<NUM>);
a light emitting layer (<NUM>);
an electron transport layer (<NUM>), an electron injection layer (<NUM>), or an electron transport and injection layer (<NUM>); and
a cathode (<NUM>),
wherein the light emitting layer (<NUM>) comprises a compound represented by the following Chemical Formula <NUM>, and
the electron transport layer (<NUM>), the electron injection layer (<NUM>), or the electron transport and injection layer (<NUM>) comprises at least one of the compound represented by the following Chemical Formula <NUM> and the compound represented by Chemical Formula <NUM>:
<CHM>
in the Chemical Formula <NUM>,
Z is O or S,
L<NUM> is a direct bond; or substituted or unsubstituted C<NUM>-<NUM> arylene,
Ar<NUM> is substituted or unsubstituted C<NUM>-<NUM> aryl,
R<NUM> to R<NUM> are each independently hydrogen; deuterium; or substituted or unsubstituted C<NUM>-<NUM> aryl, or two adjacent substituents of R<NUM> to R<NUM> are combined to form a benzene ring,
n is an integer of <NUM> to <NUM>,
m is an integer of <NUM> to <NUM>, and
o is an integer of <NUM> to <NUM>,
<CHM>
<CHM>
in the Chemical Formula <NUM> or <NUM>,
R<NUM> to R<NUM> are each independently hydrogen, or deuterium,
p1 to p4 are an integer of <NUM> to <NUM>,
L<NUM> and L<NUM> are each independently a direct bond; or substituted or unsubstituted C<NUM>-<NUM> arylene, and
Ar<NUM> and Ar<NUM> are each independently a substituent represented by the following Chemical Formula <NUM>,
<CHM>
in the Chemical Formula <NUM>,
X<NUM> to X<NUM> are each independently N or CR<NUM>, wherein at least two of X<NUM> to X<NUM> are N, and
each R<NUM> is independently hydrogen; deuterium; substituted or unsubstituted C<NUM>-<NUM> alkyl; substituted or unsubstituted C<NUM>-<NUM> aryl; or substituted or unsubstituted C<NUM>-<NUM> heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S, or two adjacent R<NUM>s are combined to form a benzene ring.