WO2017171420A1 - Compound and organic light emitting element using same - Google Patents

Abstract

The present specification provides a compound of chemical formula 1 and an organic light emitting element comprising the same.

Description

Compound and organic light emitting device using same

The present specification relates to an organic compound and an organic light emitting device using the same. This specification claims the benefit of the filing date of Korean Patent Application No. 10-2016-0038464 filed with the Korea Intellectual Property Office on March 30, 2016, the entire contents of which are incorporated herein.

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. The organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.

There is a continuing need for the development of new materials for such organic light emitting devices.

In the present specification, a compound and an organic light emitting device including the same are described.

An exemplary embodiment of the present specification provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1, at least one of X1 to X3 is N, the rest is CR,

R is the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 3 to 20 carbon atoms,

Ar1, Ar2 and -L- (Y) n are different from each other,

Ar1 and Ar2 are different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 3 to 20 carbon atoms,

L is a direct bond; A substituted or unsubstituted monocyclic or polycyclic divalent to hexavalent aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic divalent to hexavalent heteroaryl group having 3 to 20 carbon atoms,

Y is a naphthyl group; Phenanthrene group; Dimethyl fluorene group; Anthracene group; Triphenylene group; Pyrene group; Tetracene group; Chrysene group; Perylene group; Or a fluoranthene group,

n is an integer of 2-5, and some Y is the same or different.

In addition, an exemplary embodiment of the present specification includes a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of Formula 1.

The compound described herein can be used as the material of the organic material layer of the organic light emitting device. The compound according to at least one exemplary embodiment may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode. In particular, the compounds described herein can be used as hole injection, hole transport, hole injection and transport, luminescence, electron transport, or electron injection materials, preferably as a material of a light emitting layer, an electron transport layer or an electron injection layer. .

FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.

FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.

3 is a mass spectrum of Compound 1 according to Preparation Example 1. FIG.

4 is a mass spectrum of Compound 2 according to Preparation Example 2. FIG.

5 is a mass spectrum of Compound 3 according to Preparation Example 3. FIG.

6 is a Mass spectrum of Compound 4 according to Preparation Example 4. FIG.

7 is a Mass spectrum of Compound 5 according to Preparation Example 5. FIG.

8 is a Mass spectrum of Compound 6 according to Preparation Example 6. FIG.

9 is a Mass spectrum of Compound 9 according to Preparation Example 9. FIG.

10 is a Mass spectrum of Compound 10 according to Preparation Example 10. FIG.

11 is a Mass spectrum of Compound 11 according to Preparation Example 11. FIG.

12 is a Mass spectrum of Compound 12 according to Preparation 12. FIG.

13 is a Mass spectrum of Compound 13 according to Preparation Example 13. FIG.

14 is a Mass spectrum of Compound 16 according to Preparation 16. FIG.

15 is a Mass spectrum of Compound 17 according to Preparation Example 17. FIG.

16 is a Mass spectrum of Compound 20 according to Preparation Example 20. FIG.

17 is a Mass spectrum of Compound 22 according to Preparation Example 22. FIG.

[Description of the code]

1: substrate

2: anode

3: light emitting layer

4: cathode

5: hole injection layer

6: hole transport layer

7: electron transport layer

Hereinafter, the present specification will be described in more detail.

An exemplary embodiment of the present specification provides a compound represented by Chemical Formula 1.

Examples of the substituents are described below, but are not limited thereto.

As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Nitro group; Amino group; An alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; And it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group, or substituted or unsubstituted two or more substituents of the substituents exemplified above. For example, the substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.

In the present specification, the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, but may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. The polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

When the fluorenyl group is substituted,

,

,

And

And so on. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group including one or more of O, N, S, Si, and Se as heterologous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group are thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridil group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiadia There may be a sleepy group, a phenothiazinyl group, a dibenzofuranyl group, and the like, but is not limited thereto.

In the present specification, the heterocyclic group may be monocyclic or polycyclic, may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group.

In the present specification, the condensation structure may be a structure in which an aromatic hydrocarbon ring is condensed to a corresponding substituent. For example, as a condensed ring of benzimidazole

Etc., but is not limited thereto.

In the present specification, the description of the aryl group described above may be applied except that the arylene is a divalent group.

In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group.

In one embodiment of the present specification, X1 is N, X2 and X3 are CR.

In one embodiment of the present specification, X2 is N, X1 and X3 are CR.

In one embodiment of the present specification, X1 and X2 are N, and X3 is CR.

In one embodiment of the present specification, X2 and X3 are N, and X1 is CR.

In one embodiment of the present specification, X1 to X3 are N.

In one embodiment of the present specification, R is hydrogen or deuterium.

In one embodiment of the present specification, R is hydrogen.

In one embodiment of the present specification, Ar1 and Ar2 are different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 3 to 20 carbon atoms.

In one embodiment of the present specification, Ar1 and Ar2 are different from each other, each independently represent a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar1 and Ar2 are different from each other, and each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted dimethyl fluorene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted naphthyl group or substituted or unsubstituted pyrene group.

In one embodiment of the present specification, Ar1 and Ar2 are different from each other, and each independently a phenyl group; Biphenyl group; Phenanthrene group; Dimethyl fluorene group; Dibenzofuran group; Dibenzothiophene group; Naphthyl group or pyrene group.

In one embodiment of the present specification, Ar1 is a phenyl group, Ar2 is a biphenyl group; Phenanthrene group; Dimethyl fluorene group; Dibenzofuran group; Dibenzothiophene group; Naphthyl group or pyrene group.

In one embodiment of the present specification, L is a substituted or unsubstituted monocyclic or polycyclic divalent to tetravalent aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic divalent to tetravalent heteroaryl group having 3 to 20 carbon atoms.

In one embodiment of the present specification, L is a substituted or unsubstituted monocyclic or polycyclic divalent to tetravalent aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, L is a substituted or unsubstituted monocyclic or polycyclic trivalent aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, L is a divalent to tetravalent phenyl group; Divalent to tetravalent biphenyl groups; Divalent to tetravalent naphthyl groups; Divalent to tetravalent phenanthrene groups; Divalent to tetravalent carbazole groups; Divalent to tetravalent pyridine groups; Divalent to tetravalent pyrimidine groups; Divalent to tetravalent triazine groups; Divalent to tetravalent quinoline groups; Divalent to tetravalent dibenzofuran groups; Or a divalent to tetravalent dibenzothiophene group.

In one embodiment of the present specification, L is a substituted or unsubstituted trivalent phenyl group; Substituted or unsubstituted trivalent biphenyl group; Substituted or unsubstituted trivalent phenanthrene group; Substituted or unsubstituted trivalent dimethyl fluorene group; Substituted or unsubstituted trivalent dibenfuran group; Substituted or unsubstituted trivalent dibenzothiophene group; Substituted or unsubstituted trivalent naphthyl group or substituted or unsubstituted trivalent pyrene group.

In one embodiment of the present specification, L is a divalent to tetravalent phenyl group; Divalent to tetravalent biphenyl groups; Divalent to tetravalent phenanthrene groups; Divalent to tetravalent dimethylfluorene groups; Divalent to tetravalent dibenfuran groups; Divalent to tetravalent dibenzothiophene groups; Or a divalent to tetravalent naphthyl group or a divalent to tetravalent pyrene group.

In one embodiment of the present specification, L is a trivalent phenylene group; Trivalent biphenylylene group; Trivalent phenanthrene group; Trivalent dimethyl fluorene group; Trivalent dibenfuran group; Trivalent dibenzothiophene group; It is a trivalent naphthyl group or a trivalent pyrene group.

In one embodiment of the present specification, L is a divalent to tetravalent phenyl group or a divalent to tetravalent biphenyl group.

In one embodiment of the present specification, L is a trivalent phenyl group or a trivalent biphenyl group.

In one embodiment of the present specification, Y is selected from the following structural formulas.

In one embodiment of the present specification, Y is a naphthyl group or a phenanthrene group.

In one embodiment of the present specification, the plurality of Y is different.

In one embodiment of the present specification, the plurality of Y is the same.

In one embodiment of the present specification, the compound of Formula 1 is any one selected from the following structural formulas.

The compound according to an exemplary embodiment of the present application may be prepared by the manufacturing method described below.

For example, the compound of Formula 1 may have a core structure as shown in Scheme 1 below. Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.

Scheme 1

In Scheme 1, a compound of formula A may be obtained by performing a coupling reaction using a triazine compound and a linker of boronic acid or boronate as a catalyst with Pd.

Bis (pinacolato) diboron equivalent of Formula A was added to a dioxane solvent, followed by borylation reaction using KOAc and Pd as catalysts. Compounds can be obtained.

The core structure of Formula 1 may be obtained through a coupling reaction between the compound of Formula B and compound Y.

In addition, the present specification provides an organic light emitting device including the compound described above.

In one embodiment of the present application, the first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.

In this specification, when a member is located "on" another member, this includes not only when a member is in contact with another member but also when another member exists between the two members.

In the present specification, when a part "contains" a certain component, this means that the component may further include other components, except for the case where there is no contrary description.

The organic material layer of the organic light emitting device of the present application may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked. For example, as a representative example of the organic light emitting device of the present invention, the organic light emitting device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound.

In an exemplary embodiment of the present application, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.

In an exemplary embodiment of the present application, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.

In an exemplary embodiment of the present application, the organic material layer includes an electron transporting layer, an electron injection layer, or a layer for simultaneously injecting or transporting an electron, and the electron injection layer, an electron transporting layer, or a layer for simultaneously injecting and transporting an electron is Compound.

In an exemplary embodiment of the present application, the compound is included in the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electrons May comprise additional compounds.

In an exemplary embodiment of the present application, the compound is included in the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electrons May further comprise an N-type dopant.

In an exemplary embodiment of the present application, the compound is included in the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electrons It may further comprise a silver metal complex.

In an exemplary embodiment of the present application, the compound is included in the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electrons The silver alkali metal complex may further include.

In an exemplary embodiment of the present application, the compound is included in the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electrons May further comprise lithium quinolate.

In an exemplary embodiment of the present application, the compound is included in the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electrons May include the compound of the present application and lithium quinolate in a weight ratio of 1: 9 to 9: 1.

In an exemplary embodiment of the present application, the compound is included in the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electrons May include the compound of the present application and lithium quinolate in a weight ratio of 4: 6 to 6: 4.

In an exemplary embodiment of the present application, the compound is included in the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electron injection layer, the electron transport layer, or a layer for simultaneously injecting and transporting the electrons May include the compound of the present application and lithium quinolate in a weight ratio of 1: 1.

In one embodiment of the present application, the organic layer has a thickness of 1 kPa to 1000 kPa, more preferably 1 kPa to 500 kPa.

In an exemplary embodiment of the present application, the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the compound.

In one embodiment of the present application, the organic light emitting device comprises a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. Two or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers comprises the compound.

In an exemplary embodiment of the present application, the two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer simultaneously performing electron transport and electron injection, and a hole blocking layer.

In an exemplary embodiment of the present application, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound. Specifically, in one embodiment of the present specification, the compound may be included in one layer of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.

In addition, in an exemplary embodiment of the present application, when the compound is included in each of the two or more electron transport layers, other materials except for the compound may be the same or different from each other.

In an exemplary embodiment of the present application, the organic material layer further includes a hole injection layer or a hole transport layer including a compound including an arylamino group, carbazolyl group, or benzocarbazolyl group in addition to the organic material layer including the compound.

In another exemplary embodiment, the organic light emitting diode may be an organic light emitting diode having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

 In another exemplary embodiment, the organic light emitting diode may be an organic light emitting diode having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

For example, the structure of the organic light emitting device according to the exemplary embodiment of the present application is illustrated in FIGS. 1 and 2.

1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked. In such a structure, the compound may be included in the light emitting layer (3).

2 shows an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4 are sequentially stacked. The structure is illustrated. In such a structure, the compound may be included in at least one of the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, and the electron transport layer 7.

In such a structure, the compound may be included in one or more layers of the hole injection layer, hole transport layer, light emitting layer and electron transport layer.

The organic light emitting device of the present application may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present application, that is, the compound.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

 The organic light emitting device of the present application may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound, that is, the compound represented by Chemical Formula 1.

For example, the organic light emitting device of the present application may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. And an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound of Formula 1 may be formed of an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.

In addition to such a method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

In one embodiment of the present application, the first electrode is an anode, and the second electrode is a cathode.

In another exemplary embodiment, the first electrode is a cathode and the second electrode is an anode.

As the anode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO: Al or SnO ₂ : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

The hole injection material is a layer for injecting holes from an electrode, and the hole injection material has a capability of transporting holes, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in a light emitting layer. The compound which prevents the movement of the excited excitons to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. As a hole transport material, the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocyclic containing compounds include dibenzofuran derivatives, ladder type furan compounds, and pyrides. Midine derivatives and the like, but is not limited thereto.

The electron transporting material is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. The electron transporting material is a material that can inject electrons well from the cathode and move them to the light emitting layer. This is suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.

The electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer. The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.

The hole blocking layer is a layer for blocking the arrival of the cathode of the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.

The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double side emission type according to a material used.

Preparation of the compound represented by Chemical Formula 1 and an organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

< Production Example >

Preparation Example 1 Synthesis of Compound 1

1) Synthesis of Compound 1-A

2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (15 g, 43.6 mmol), (3,5-dichloro under nitrogen stream Phenyl) boronic acid (9.2 g, 47.9 mmol) was dissolved in 150 mL of a tetrahydrofuran solvent, and then an aqueous solution of potassium carbonate (12.1 g, 87.3 mmol) was added thereto, followed by heating and stirring. Pd (PPh 3) 4 (1.5 g, 1.3 mmol) was added thereto under reflux, and the mixture was heated and stirred for 6 hours. After the reaction was completed, the temperature was lowered to room temperature, and the potassium carbonate solution was removed and filtered. The filtered solid was washed with ethanol to give compound 1-A (17.8 g, 90% yield).

MS [M + H] &lt; + &gt; = 454

2) Synthesis of Compound 1-B

Compound 1-A (17.8g, 39.2mmol) and bis (pinacolato) diboron (10.9g, 43.1mmol) were dissolved in 180 mL of dioxane solvent under nitrogen stream, and then potassium acetate (11.5g, 117.5mmol) was added thereto. It stirred by heating. Pd (dba) 2 (0.7 g, 1.2 mmol) and PCy 3 (0.7 g, 2.4 mmol) were added thereto under reflux, and the mixture was heated and stirred for 8 hours. After the reaction was completed, the temperature was lowered to room temperature, and then filtered first to remove impurities. The filtrate was poured into water, extracted with chloroform and the organic layer was dried over anhydrous magnesium sulfate. Distillation under reduced pressure and washing with ethanol afforded Compound 1-B (21 g, yield 84%).

MS [M + H] &lt; + &gt; = 637

3) Synthesis of Compound 1

Compound 1-B (21 g, 32.9 mmol) and 1-bromonaphthalene (14.3 g, 69.2 mmol) were dissolved in tetrahydrofuran under a nitrogen stream, and then heated and stirred in an aqueous solution of potassium carbonate (18.2 g, 132.8 mmol). Pd (PPh 3) 4 (1.2 g, 1.0 mmol) was added under reflux, and the mixture was heated and stirred for 8 hours. After the reaction was completed, the temperature was lowered to room temperature, and the potassium carbonate solution was removed and filtered. The filtered solid was washed with ethanol to give compound 1 (18 g, 85% yield).

MS [M + H] &lt; + &gt; = 637

Synthesis confirmation data of the compound 1 is shown in FIG.

Preparation Example 2 Synthesis of Compound 2

Compound 1-B (21 g, 32.9 mmol) and 2-bromonaphthalene (14.3 g, 69.2 mmol) were dissolved in tetrahydrofuran under a nitrogen stream, and then heated and stirred in an aqueous solution of potassium carbonate (18.2 g, 132.8 mmol). Pd (PPh 3) 4 (1.2 g, 1.0 mmol) was added under reflux, and the mixture was heated and stirred for 8 hours. After the reaction was completed, the temperature was lowered to room temperature, and the potassium carbonate solution was removed and filtered. The filtered solid was washed with ethanol to give compound 2 (18g, 85% yield).

MS [M + H] &lt; + &gt; = 637

Synthesis confirmation data of the compound 2 is shown in FIG.

Preparation Example 3 Synthesis of Compound 3

1) Synthesis of Compound 3-A

 Compound 3-A was prepared by the same method as Compound 1-A, except that (3-bromo-5-chlorophenyl) boronic acid was used instead of (3,5-dichlorophenyl) boronic acid.

MS [M + H] &lt; + &gt; = 498

2) Synthesis of Compound 3-B

Dissolve compound 3-A (20 g, 40.1 mmol) and 1-naphthalenyl boronic acid (7.6 g, 44.1 mmol) in 1.4-diox in a nitrogen stream, and add potassium phosphate (17.0 g, 80.2 mmol) in an aqueous solution It was. Pd (PPh 3) 4 (1.4 g, 1.2 mmol) was added under reflux, and the mixture was heated and stirred for 8 hours. After the reaction was completed, the temperature was lowered to room temperature, and the potassium phosphate solution was removed and filtered. The filtered solid was washed with ethanol to give compound 3-B (18 g, 82% yield).

MS [M + H] &lt; + &gt; = 546

3) Synthesis of Compound 3

Compound 3 was prepared in the same manner as Compound 1, except that Compound 3-B was used instead of Compound 1-B and (4- (1-naphthalenyl) phenyl) boronic acid was used instead of 1-bromonaphthalene.

MS [M + H] &lt; + &gt; = 714

Synthesis confirmation data of the compound 3 is shown in FIG.

Preparation Example 4 Synthesis of Compound 4

 Compound 4 was prepared in the same manner as Compound 3, except that (4- (2-naphthalenyl) phenyl) boronic acid was used instead of (4- (1-naphthalenyl) phenyl) boronic acid.

MS [M + H] &lt; + &gt; = 714

Synthesis confirmation data of the compound 4 is shown in FIG.

Preparation Example 5 Synthesis of Compound 5

1) Synthesis of Compound 5-B

Compound 5-B was prepared by the same method as Compound 3-B, except that 2-naphthalenylboronic acid was used instead of 1-naphthalenylboronic acid.

MS [M + H] &lt; + &gt; = 546

2) Synthesis of Compound 5

Compound 3 and 3 except that Compound 5-B was used instead of (4- (1-naphthalenyl) phenyl) boronic acid and instead of (4- (2-naphthalenyl) phenyl) boronic acid Compound 5 was prepared in the same manner.

MS [M + H] &lt; + &gt; = 714

Synthesis confirmation data of the compound 5 is shown in FIG.

Preparation Example 6 Synthesis of Compound 6

Compound 6 was prepared in the same manner as Compound 5, except that (4- (1-naphthalenyl) phenyl) boronic acid was used instead of (4- (2-naphthalenyl) phenyl) boronic acid.

 MS [M + H] &lt; + &gt; = 714

Synthesis confirmation data of the compound 6 is shown in FIG.

Preparation Example 7 Synthesis of Compound 7

 Compound 7 was prepared in the same manner as Compound 1, except that 9-bromophenanthrene was used instead of 1-bromonaphthalene.

MS [M + H] &lt; + &gt; = 738

Preparation Example 8 Synthesis of Compound 8

1) Synthesis of Compound 8-A

2-([1,1'-biphenyl] -3- instead of 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine Compound 8-A was prepared by the same method as Compound 1-A, except for using one) -4-chloro-6-phenyl-1,3,5-triazine.

MS [M + H] &lt; + &gt; = 454

2) Synthesis of Compound 8-B

Compound 8-B was prepared by the same method as Compound 1-B, except that Compound 8-A was used instead of Compound 1-A.

MS [M + H] &lt; + &gt; = 638

3) Synthesis of Compound 8

Compound 8 was prepared in the same manner as Compound 7, except that Compound 8-B was used instead of Compound 1-B.

MS [M + H] &lt; + &gt; = 738

Preparation Example 9 Synthesis of Compound 9

Compound 9 was prepared in the same manner as Compound 8, except that 1-bromonaphthalene was used instead of 9-bromophenanthrene.

MS [M + H] &lt; + &gt; = 638

Synthesis confirmation data of the compound 9 is shown in FIG.

Preparation Example 10 Synthesis of Compound 10

Compound 10 was prepared in the same manner as Compound 8, except that 2-bromonaphthalene was used instead of 9-bromophenanthrene.

MS [M + H] &lt; + &gt; = 638

Synthesis confirmation data of the compound 10 is shown in FIG.

Preparation Example 11 Synthesis of Compound 11

1) Synthesis of Compound 11-A

2-([1,1'-biphenyl] -3- instead of 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine Compound 11-A was prepared by the same method as Compound 3-A, except that one) -4-chloro-6-phenyl-1,3,5-triazine was used.

MS [M + H] &lt; + &gt; = 499

2) Synthesis of Compound 11-B

Compound 11-B was prepared by the same method as Compound 3-B, except that 11-A was used instead of Compound 3-A.

MS [M + H] &lt; + &gt; = 546

3) Synthesis of Compound 11

Compound 11 was prepared in the same manner as Compound 3, except that Compound 11-B was used instead of Compound 3-B.

MS [M + H] &lt; + &gt; = 714

Synthesis confirmation data of the compound 11 is shown in FIG.

Preparation Example 12 Synthesis of Compound 12

Compound 12 was prepared by the same method as Compound 4, except that Compound 11-B was used instead of Compound 3-B.

MS [M + H] &lt; + &gt; = 714

Synthesis confirmation data of the compound 12 is shown in FIG.

Preparation Example 13 Synthesis of Compound 13

1) Synthesis of Compound 13-B

Compound 13-B was prepared by the same method as Compound 5-B, except that Compound 11-A was used instead of Compound 3-A.

MS [M + H] &lt; + &gt; = 546

2) Synthesis of Compound 13

Compound 13 was prepared by the same method as Compound 5, except that Compound 13-B was used instead of Compound 5-B.

MS [M + H] &lt; + &gt; = 714

Synthesis confirmation data of the compound 13 is shown in FIG.

Preparation Example 14 Synthesis of Compound 14

Compound 14 was prepared in the same manner as Compound 13, except that (4- (naphthalen-1-yl) phenyl) boronic acid was used instead of (4- (naphthalen-2-yl) phenyl) boronic acid.

MS [M + H] &lt; + &gt; = 714

Preparation Example 16 Synthesis of Compound 16

1) Synthesis of Compound 16-A

2-chloro-4- (dibenzo [b, d] furan instead of 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine Compound 16-A was prepared by the same method as Compound 1-A, except that -1-yl) -6-phenyl-1,3,5-triazine was used.

MS [M + H] &lt; + &gt; = 468

2) Synthesis of Compound 16-B

Compound 16-B was prepared by the same method as Compound 1-B, except that Compound 16-A was used instead of Compound 1-A.

MS [M + H] &lt; + &gt; = 652

3) Synthesis of Compound 16

Compound 16 was prepared in the same manner as Compound 1, except that Compound 16-B was used instead of Compound 1-B.

MS [M + H] &lt; + &gt; = 652

Synthesis confirmation data of the compound 16 is shown in FIG.

Preparation Example 17 Synthesis of Compound 17

Compound 17 was prepared in the same manner as Compound 1, except for using Compound 16-B instead of Compound 1-B and using 2-bromonaphthalene instead of 1-bromonaphthalene.

MS [M + H] &lt; + &gt; = 652

Synthesis confirmation data of the compound 17 is shown in FIG.

Preparation Example 18 Synthesis of Compound 18

1) Synthesis of Compound 18-A

2-chloro-4- (dibenzo [b, d] furan instead of 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine Compound 18-A was prepared by the same method as Compound 3-A, except that -1-yl) -6-phenyl-1,3,5-triazine was used.

MS [M + H] &lt; + &gt; = 512

2) Synthesis of Compound 18-B

Compound 18-B was prepared by the same method as Compound 3-B, except that Compound 18-A was used instead of Compound 3-A.

MS [M + H] &lt; + &gt; = 560

3) Synthesis of Compound 18

 Compound 18 was prepared in the same manner as Compound 3, except that Compound 18-B was used instead of Compound 3-B.

MS [M + H] &lt; + &gt; = 728

Preparation Example 19 Synthesis of Compound 19

Compound 19 was prepared by the same method as Compound 4, except that Compound 18-B was used instead of Compound 3-B.

MS [M + H] &lt; + &gt; = 728

Preparation Example 20 Synthesis of Compound 20

1) Synthesis of Compound 20-B

Compound 20-B was prepared by the same method as Compound 18-B, except that 2-naphthalene boronic acid was used instead of 1-naphthalene boronic acid.

MS [M + H] &lt; + &gt; = 560

2) Synthesis of Compound 20

 Compound 20 was prepared in the same manner as Compound 5, except that Compound 20-B was used instead of Compound 5-B.

MS [M + H] &lt; + &gt; = 728

Synthesis confirmation data of the compound 20 is shown in FIG.

Preparation Example 21 Synthesis of Compound 21

 Compound 21 was prepared by the same method as Compound 20, except that (4- (naphthalen-1-yl) phenyl) boronic acid was used instead of (4- (naphthalen-2-yl) phenyl) boronic acid.

MS [M + H] &lt; + &gt; = 728

Preparation Example 22 Synthesis of Compound 22

Compound 22 was prepared in the same manner as Compound 16, except that 9-bromophenanthrene was used instead of 1-bromonaphthalene.

MS [M + H] &lt; + &gt; = 752

Synthesis confirmation data of the compound 22 is shown in FIG.

Preparation Example 23 Synthesis of Compound 23

1) Synthesis of Compound 23-A

Compound 23-A was prepared by the same method as Compound 1-A, except that (2,5-dichlorophenyl) boronic acid was used instead of (3,5-dichlorophenyl) boronic acid.

MS [M + H] &lt; + &gt; = 454

2) Synthesis of Compound 23-B

Compound 23-B was prepared by the same method as Compound 1-B, except that Compound 23-A was used instead of Compound 1-A.

MS [M + H] &lt; + &gt; = 638

3) Synthesis of Compound 23

 Compound 23 was prepared by the same method as Compound 1, except that Compound 23-B was used instead of Compound 1-B.

MS [M + H] &lt; + &gt; = 638

Preparation Example 24 Synthesis of Compound 24

 Compound 24 was prepared in the same manner as Compound 23, except that 2-bromonaphthalene was used instead of 1-bromonaphthalene.

MS [M + H] &lt; + &gt; = 638

Preparation 25 Synthesis of Compound 25

 Compound 25 was prepared in the same manner as Compound 23, except that 9-bromophenanthrene was used instead of 1-bromonaphthalene.

MS [M + H] &lt; + &gt; = 738

Preparation Example 26 Synthesis of Compound 26

1) Synthesis of Compound 26-A

 2-chloro-4- (naphthalen-2-yl) -6 instead of 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine Compound 3-, except that -phenyl-1,3,5-triazine was used and (2-bromo-4-chlorophenyl) boronic acid was used instead of (3-bromo-5-chlorophenyl) boronic acid Compound 26-A was prepared in the same manner as A.

MS [M + H] &lt; + &gt; = 472

2) Synthesis of Compound 26-B

 Compound 26-B was prepared by the same method as Compound 3-B, except that Compound 26-A was used instead of Compound 3-A.

MS [M + H] &lt; + &gt; = 520

3) Synthesis of Compound 26

Compound 3, except that compound 26-B was used instead of compound 3-B and (4- (phenanthren-9-yl) phenyl) boronic acid was used instead of (4- (naphthalen-1-yl) phenyl) boronic acid Compound 26 was prepared in the same manner as described above.

MS [M + H] &lt; + &gt; = 738

<Example>

Example 1

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as a detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.

The following compound [HI-A] was thermally vacuum deposited to a thickness of 600 kPa on the prepared ITO transparent electrode to form a hole injection layer. Hexanitrile hexaazatriphenylene (HAT) of the following formula on the hole injection layer 50 Å and the following compound [HT-A] (600 Å) was sequentially vacuum-deposited to form a hole transport layer.

Subsequently, the following compounds [BH] and [BD] were vacuum-deposited at a weight ratio of 25: 1 on the hole transport layer to have a film thickness of 200 Pa to form a light emitting layer. Compound 1 and [LiQ] (Lithiumquinolate) were vacuum-deposited at a weight ratio of 1: 1 on the emission layer to form an electron injection and transport layer at a thickness of 350 kHz. On the electron injection and transport layer, lithium fluoride (LiF) and aluminum were deposited to a thickness of 1,000 Å in order to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.9 Å / sec, the lithium fluoride of the cathode was maintained at a deposition rate of 0.3 Å / sec, aluminum 2 Å / sec, the vacuum degree during deposition was 1 × 10 ^-7 to 5 × 10 ^- to maintain the ⁸ torr, it was produced in the organic light emitting device.

Example 2

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2 was used instead of Compound 1 in Example 1.

Example 3

 An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 3 was used instead of Compound 1 in Example 1.

Example 4

 An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 4 was used instead of Compound 1 in Example 1.

Example 5

 An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 5 was used instead of Compound 1 in Example 1.

Example 6

 An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 6 was used instead of Compound 1 in Example 1.

Example 7

 An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 7 was used instead of Compound 1 in Example 1.

Example 8

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 8 was used instead of Compound 1 in Example 1.

Example 9

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 9 was used instead of Compound 1 in Example 1.

Example 10

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 10 was used instead of Compound 1 in Example 1.

Example 11

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 11 was used instead of Compound 1 in Example 1.

Example 12

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 12 was used instead of Compound 1 in Example 1.

Example 13

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 13 was used instead of Compound 1 in Example 1.

Example 14

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 14 was used instead of Compound 1 in Example 1.

Example 16

  An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 16 was used instead of Compound 1 in Example 1.

Example 17

 An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 17 was used instead of Compound 1 in Example 1.

Example 18

 An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 18 was used instead of Compound 1 in Example 1.

Example 19

 An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 19 was used instead of Compound 1 in Example 1.

Example 20

 An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 20 was used instead of Compound 1 in Example 1.

Example 21

 An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 21 was used instead of Compound 1 in Example 1.

Example 22

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 22 was used instead of Compound 1 in Example 1.

Example 23

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 23 was used instead of Compound 1 in Example 1.

Example 24

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 24 was used instead of Compound 1 in Example 1.

Example 25

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 25 was used instead of Compound 1 in Example 1.

Example 26

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 26 was used instead of Compound 1 in Example 1.

Comparative Example 1

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET1 was used instead of Compound 1 in Example 1.

Comparative Example 2

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET2 was used instead of Compound 1 in Example 1.

Comparative Example 3

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET3 was used instead of Compound 1 in Example 1.

Comparative Example 4

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET4 was used instead of Compound 1 in Example 1.

Comparative Example 5

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET5 was used instead of Compound 1 in Example 1.

Comparative Example 6

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET6 was used instead of Compound 1 in Example 1.

The organic light emitting diodes of Examples 1 to 14, 16 to 26 and Comparative Examples 1 to 6 measured driving voltage and luminous efficiency at a current density of 10 mA / cm ² , and compared to initial luminance at a current density of 20 mA / cm ² . The time to become% (LT90) was measured. The results are shown in Table 1 below.

Example 10 mA / cm 2	compound	Voltage (V)	Current efficiency (cd / A)	Color coordinates (x, y)	Life Time (T90 at 20mA / cm 2 )
Example 1	One	3.68	5.29	(0.142, 0.096)	127
Example 2	2	3.68	5.41	(0.142, 0.096)	116
Example 3	3	3.73	5.15	(0.142, 0.096)	180
Example 4	4	3.72	5.23	(0.142, 0.097)	167
Example 5	5	3.72	5.26	(0.142, 0.096)	159
Example 6	6	3.81	5.21	(0.142, 0.097)	131
Example 7	7	3.80	5.12	(0.142, 0.096)	142
Example 8	8	3.75	5.35	(0.142, 0.096)	108
Example 9	9	3.63	5.42	(0.142, 0.096)	103
Example 10	10	3.63	5.48	(0.142, 0.096)	101
Example 11	11	3.68	5.37	(0.142, 0.095)	150
Example 12	12	3.67	5.44	(0.142, 0.096)	133
Example 13	13	3.66	5.47	(0.142, 0.096)	125
Example 14	14	3.76	5.42	(0.142, 0.097)	105
Example 16	16	3.71	5.25	(0.142, 0.096)	132
Example 17	17	3.71	5.37	(0.142, 0.096)	121
Example 18	18	3.76	5.11	(0.142, 0.096)	181
Example 19	19	3.75	5.19	(0.142, 0.097)	127
Example 20	20	3.74	5.22	(0.142, 0.096)	160
Example 21	21	3.84	5.17	(0.142, 0.096)	130
Example 22	22	3.83	5.08	(0.142, 0.096)	147
Example 23	23	3.70	5.31	(0.142, 0.096)	114
Example 24	24	3.70	5.38	(0.142, 0.096)	103
Example 25	25	3.82	5.14	(0.142, 0.096)	129
Example 26	26	4.01	5.01	(0.142, 0.097)	100
Comparative Example 1	ET 1	4.72	3.91	(0.142, 0.098)	88
Comparative Example 2	ET 2	5.05	3.61	(0.142, 0.096)	95
Comparative Example 3	ET 3	4.98	3.71	(0.142, 0.096)	84
Comparative Example 4	ET 4	4.99	3.69	(0.142, 0.096)	87
Comparative Example 5	ET 5	5.12	3.58	(0.142, 0.095)	74
Comparative Example 6	ET 6	5.02	3.68	(0.142, 0.096)	90

From the results of Table 1, it can be seen that the compound represented by Formula 1 according to an exemplary embodiment of the present specification can be used in the organic material layer capable of simultaneously injecting and transporting electrons of the organic light emitting device.

In particular, compounds ET2 and ET6 of Comparative Examples 2 and 6 were confirmed that Ar1 and Ar2 of the present invention showed a high voltage, low efficiency, low life, and Compounds ET3 and ET4 of Comparative Examples 3 and 4 were Compounds having substituents not included in the definition of Y of the present invention showed higher voltage, lower efficiency, and lower life than the compounds of Examples 1 to 14 and 16 to 26.

Claims (10)

1. Compound represented by the following formula (1):

   [Formula 1]

   

   In Formula 1, at least one of X1 to X3 is N, the rest is CR,

   R is the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 3 to 20 carbon atoms,

   Ar1, Ar2 and -L- (Y) n are different from each other,

   Ar1 and Ar2 are different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 3 to 20 carbon atoms,

   L is a direct bond; A substituted or unsubstituted monocyclic or polycyclic divalent to hexavalent aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic divalent to hexavalent heteroaryl group having 3 to 20 carbon atoms,

   Y is a naphthyl group; Phenanthrene group; Dimethyl fluorene group; Anthracene group; Triphenylene group; Pyrene group; Tetracene group; Chrysene group; Perylene group; Or a fluoranthene group,

   n is an integer of 2-5, and some Y is the same or different.
2. The method according to claim 1, wherein L is a divalent to tetravalent phenyl group; Divalent to tetravalent biphenyl groups; Divalent to tetravalent naphthyl groups; Divalent to tetravalent phenanthrene groups; Divalent to tetravalent carbazole groups; Divalent to tetravalent pyridine groups; Divalent to tetravalent pyrimidine groups; Divalent to tetravalent triazine groups; Divalent to tetravalent quinoline groups; Divalent to tetravalent dibenzofuran groups; Or a divalent to tetravalent dibenzothiophene group.
3. The method according to claim 1, wherein L is a trivalent phenyl group; Or a trivalent biphenyl group.
4. The compound of claim 1, wherein the plurality of Y is the same.
5. The compound of claim 1, wherein the plurality of Y is different.
6. The method according to claim 1, Ar1 and Ar2 are different from each other, each independently represent a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted dimethyl fluorene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted pyrene group.
7. The compound of claim 1, wherein Y is a naphthyl group or a phenanthrene group.
8. The compound of claim 1, wherein the compound of Formula 1 is any one selected from the following structural formulas:

   

   

   

   

   

   

   

   

   

   

   

   

   
9. A first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound according to any one of claims 1 to 8. Organic light emitting device.
10. The method of claim 9, wherein the electron transport layer, an electron injection layer or a layer for simultaneously injecting or transporting the electron, the electron injection layer, an electron transport layer, or a layer for simultaneously injecting and transporting the organic containing the compound Light emitting element.

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