KR101833669B1 - Compound and organic electronic device using the same - Google Patents

Abstract

The present invention provides a compound of formula (1) and an organic light emitting device comprising the same.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a compound and an organic light-

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic compound and an organic light emitting device using the organic compound. This specification claims the benefit of Korean Patent Application No. 10-2016-0038464, filed on March 30, 2016, to the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.

Development of new materials for such organic light emitting devices has been continuously required.

International Patent Application Publication No. 2003-012890

In this specification, compounds and organic light emitting devices containing them are described.

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

[Chemical Formula 1]

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

R are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; 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,

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; 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,

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

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

n is an integer of 2 to 5, and plural Ys are the same or different.

In addition, one embodiment of the present disclosure includes a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of Formula 1.

The compound described in this specification can be used as a material of an organic layer of an organic light emitting device. The compound according to at least one embodiment can improve the efficiency, lower driving voltage and / or lifetime characteristics in the organic light emitting device. In particular, the compounds described in this specification can be used as hole injecting, hole transporting, hole injecting and transporting, luminescence, electron transporting, or electron injecting materials, and preferably as materials for the light emitting layer, electron transporting layer, or electron injecting layer .

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig.
2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.
3 is a Mass spectrum of Compound 1 according to Production 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 Production 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 Production Example 6. Fig.
9 is a Mass spectrum of Compound 9 according to Production Example 9. Fig.
10 is a Mass spectrum of Compound 10 according to Production Example 10. Fig.
11 is a Mass spectrum of Compound 11 according to Production Example 11. FIG.
12 is a Mass spectrum of Compound 12 according to Production Example 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 Production Example 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.

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

An embodiment of the present invention provides a compound represented by the above formula (1).

Illustrative examples of such substituents are set forth below, but are not limited thereto.

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; An amino group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; And a heterocyclic group, or a substituted or unsubstituted one in which at least two of the above-exemplified substituents are connected to each other. For example, the substituent to which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

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

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another 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, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are 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 one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

,

,

및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

And

And the like. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a hetero ring group containing at least one of O, N, S, Si and Se as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, , A pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyranyl group, an isoquinoline group, , A carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, an isoxazolyl group, A benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group,

In the present specification, the heterocyclic group may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and examples thereof may be selected from the above heteroaryl groups.

,

,

등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the condensed structure may be a structure in which an aromatic hydrocarbon ring is condensed with the substituent. For example, as a condensation ring of benzimidazole

,

,

And the like, but the present invention is not limited thereto.

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

In the present specification, the description of the above-mentioned heterocyclic group can be applied except that the heteroarylene is a divalent group.

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

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

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

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

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

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

In one embodiment of this disclosure, R is hydrogen.

In one embodiment of the present specification, Ar1 and Ar2 are 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 invention, Ar1 and Ar2 are different from each other, and each independently represents 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 each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted dimethylfluorene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted pyrene group.

In one embodiment of the present specification, Ar1 and Ar2 are different from each other and are each independently a phenyl group; Biphenyl group; Phenanthrene; A dimethylfluorene group; A dibenzofurane group; A dibenzothiophene group; Naphthyl group; Or pyrene.

In one embodiment of the present specification, Ar1 is a phenyl group, Ar2 is a biphenyl group; Phenanthrene; A dimethylfluorene group; A dibenzofurane group; A 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 to bicyclic to tetravalent heteroarylene 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 tricyclic aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, L is a divalent to tetravalent phenyl group; A bivalent to tetravalent biphenyl group; A divalent to tetravalent naphthyl group; A phenanthrene group having 2 to 4 valences; A divalent to tetravalent carbazole group; A divalent to tetravalent pyridine group; A divalent to tetravalent pyrimidine group; A triazine group having 2 to 4 substituents; A quinoline group having 2 to 4 valences; A divalent to tetravalent dibenzofurane group; Or a divalent to tetravalent dibenzothiophene group.

In one embodiment of the present specification, L is a substituted or unsubstituted trivalent phenyl group; A substituted or unsubstituted trivalent biphenyl group; A substituted or unsubstituted trivalent phenanthrene group; A substituted or unsubstituted trivalent dimethylfluorene group; A substituted or unsubstituted trivalent dibenzofuran group; A substituted or unsubstituted divalent thiophene group; A substituted or unsubstituted trivalent naphthyl group; Or a substituted or unsubstituted trivalent pyrene group.

In one embodiment of the present specification, L is a divalent to tetravalent phenyl group; A bivalent to tetravalent biphenyl group; A phenanthrene group having 2 to 4 valences; A divalent to tetravalent dimethylfluorene group; Divalent to tetravalent dibenzofuran groups; Divalent to tetravalent dibenzothiophene groups; A divalent to tetravalent naphthyl group; Or a divalent to tetravalent pyrene group.

In one embodiment of the present invention, L is a trivalent phenylene group; Trivalent biphenyllylene groups; A trivalent phenanthrene group; A trivalent dimethylfluorene group; A trivalent dibenzofuran group; A trivalent dibenzothiophene group; 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 invention, Y is a naphthyl group or a phenanthrene group.

In one embodiment of the present disclosure, the plurality of Ys are different.

In one embodiment of the present disclosure, the plurality of Y's are the same.

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

The compound according to one embodiment of the present application can be produced by a production method described below.

For example, the compound of Formula 1 can be prepared as shown in Reaction Scheme 1 below. Substituent groups may be attached by methods known in the art, and the type, position or number of substituent groups may be varied according to techniques known in the art.

[Reaction Scheme 1]

In the above Scheme 1, a coupling reaction using Pd as a catalyst in the presence of a triazine compound and a boronic acid or boronate linker can be carried out to obtain a compound of formula (A).

Bis (pinacolato) diboron equivalent of the formula (A) is introduced into a dioxane solvent and the borylation reaction is carried out using KOAc and Pd as a catalyst to obtain the compound of formula Compound can be obtained.

The coupling structure between the compound of formula (B) and the compound (Y) provides the core structure of formula (1).

The present invention also provides an organic light emitting device comprising the above-described compound.

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

When a member is referred to herein as being "on " another member, it includes not only a member in contact with another member but also another member between the two members.

Whenever a component is referred to as "comprising ", it is understood that it may include other components as well, without departing from the other components unless specifically stated otherwise.

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

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

In one embodiment of the present application, the organic 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 one embodiment of the present application, the organic material layer includes an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer includes the above compound.

In one embodiment of the present application, the organic material layer includes an electron transport layer, an electron injection layer, or a layer simultaneously injecting or transporting electrons, and the electron injection layer, the electron transport layer, ≪ / RTI >

In one embodiment of the present application, the compound is contained in the electron injecting layer, the electron transporting layer, or the layer simultaneously injecting and transporting electrons, and the electron injecting layer, the electron transporting layer, May include additional compounds.

In one embodiment of the present application, the compound is contained in the electron injecting layer, the electron transporting layer, or the layer simultaneously injecting and transporting electrons, and the electron injecting layer, the electron transporting layer, May further include an N-type dopant.

In one embodiment of the present application, the compound is contained in the electron injecting layer, the electron transporting layer, or the layer simultaneously injecting and transporting electrons, and the electron injecting layer, the electron transporting layer, May further comprise a metal complex.

In one embodiment of the present application, the compound is contained in the electron injecting layer, the electron transporting layer, or the layer simultaneously injecting and transporting electrons, and the electron injecting layer, the electron transporting layer, May further comprise an alkali metal complex.

In one embodiment of the present application, the compound is contained in the electron injecting layer, the electron transporting layer, or the layer simultaneously injecting and transporting electrons, and the electron injecting layer, the electron transporting layer, May further comprise lithium quinolate.

In one embodiment of the present application, the compound is contained in the electron injecting layer, the electron transporting layer, or the layer simultaneously injecting and transporting electrons, and the electron injecting layer, the electron transporting layer, Can contain the present compound and lithium quinolate in a weight ratio of 1: 9 to 9: 1.

In one embodiment of the present application, the compound is contained in the electron injecting layer, the electron transporting layer, or the layer simultaneously injecting and transporting electrons, and the electron injecting layer, the electron transporting layer, May contain the present compound and lithium quinolate in a weight ratio of 4: 6 to 6: 4.

In one embodiment of the present application, the compound is contained in the electron injecting layer, the electron transporting layer, or the layer simultaneously injecting and transporting electrons, and the electron injecting layer, the electron transporting layer, May contain the present compound and lithium quinolate in a weight ratio of 1: 1.

In one embodiment of the present application, the thickness of the organic material layer is 1 ANGSTROM to 1000 ANGSTROM, more preferably 1 ANGSTROM to 500 ANGSTROM.

In one embodiment of the present application, the organic 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 includes a first electrode; A second electrode facing the first electrode; And a light emitting layer provided between the first electrode and the second electrode; At least one of the two or more organic layers includes two or more organic layers disposed between the light emitting layer and the first electrode or between the light emitting layer and the second electrode.

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

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

In the embodiment of the present application, when the compound is contained in each of the two or more electron transporting layers, the materials other than the above compounds may be the same or different from each other.

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

In another embodiment, the organic light emitting device may be a normal type organic light emitting device in which an anode, at least one organic layer, and a cathode are sequentially stacked on a substrate.

 In another embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic compound layer, and an anode are sequentially stacked on a substrate.

For example, the structure of an organic light emitting device according to one embodiment of the present application is illustrated in Figs. 1 and 2. Fig.

1 shows 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 laminated. 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 injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 7 and a cathode 4 are sequentially laminated Structure is illustrated. In such a structure, the compound may be contained in at least one of the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 3, and the electron transporting layer 7.

In such a structure, the compound may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, and the electron transporting layer.

The organic light emitting device of the present application may be manufactured by materials and methods known in the art, except that one or more of the organic layers include the compound of the present application, i.e., the compound.

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

 The organic light emitting device of the present application can be produced by materials and methods known in the art, except that one or more of the organic layers include the above compound, that is, the compound represented by the above formula (1).

For example, the organic light emitting device of the present application can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate to form a positive electrode Forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

In addition, the compound of Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum evaporation method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

In addition to such a method, an organic light emitting device may be fabricated by sequentially depositing an organic material layer and a cathode material on a substrate from a cathode material (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 embodiment, the first electrode is a cathode and the second electrode is a cathode.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode 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), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

The negative electrode material is preferably 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; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

The hole injecting material is a layer for injecting holes from the electrode. The hole injecting material has a hole injecting effect, a hole injecting effect in the anode, and an excellent hole injecting effect in the light emitting layer or the light emitting material. A compound which prevents the exciton from migrating to the electron injection layer or the electron injection material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer. 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 include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; 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 compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of heterocycle-containing compounds include dibenzofuran derivatives, ladder furan compounds, And derivatives thereof, but are not limited thereto.

The electron transporting material is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material with a low work function followed by an aluminum layer or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, 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- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

The hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole injecting layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.

The organic light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.

The preparation of the compound represented by Formula 1 and the organic light emitting device comprising 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.

< Manufacturing example >

PREPARATION EXAMPLE 1 Synthesis of Compound 1

1) Synthesis of Compound 1-A

4-chloro-6-phenyl-1,3,5-triazine (15 g, 43.6 mmol), (3,5-dichloro Phenyl) boronic acid (9.2 g, 47.9 mmol) was dissolved in 150 mL of tetrahydrofuran solvent, and then an aqueous solution of potassium carbonate (12.1 g, 87.3 mmol) was added and the mixture was heated and stirred. Pd (PPh3) 4 (1.5 g, 1.3 mmol) was added under reflux and the mixture was heated and stirred for 6 hours. After the completion of the reaction, the temperature was lowered to room temperature, and then the potassium carbonate solution was removed and filtered. The filtered solid was washed with ethanol to obtain Compound 1-A (17.8 g, yield 90%).

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

2) Synthesis of Compound 1-B

(17.8 g, 39.2 mmol) and bis (pinacolato) diboron (10.9 g, 43.1 mmol) were dissolved in 180 mL of dioxane solvent under nitrogen flow, potassium acetate (11.5 g, 117.5 mmol) Followed by heating and stirring. Pd (dba) 2 (0.7 g, 1.2 mmol) and PCy3 (0.7 g, 2.4 mmol) were added under reflux and the mixture was heated and stirred for 8 hours. After completion of the reaction, the temperature was lowered to room temperature, and then the impurities were removed by primary filtration. The filtrate was poured into water, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the residue was washed with ethanol to obtain 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 nitrogen flow and the mixture was stirred under heating with potassium carbonate (18.2 g, 132.8 mmol). The catalyst Pd (PPh3) 4 (1.2 g, 1.0 mmol) was added under reflux and the mixture was heated and stirred for 8 hours. After the completion of the reaction, the temperature was lowered to room temperature, and then 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 Compound 1 are 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 nitrogen flow and the mixture was stirred under heating with potassium carbonate (18.2 g, 132.8 mmol). The catalyst Pd (PPh3) 4 (1.2 g, 1.0 mmol) was added under reflux and the mixture was heated and stirred for 8 hours. After the completion of the reaction, the temperature was lowered to room temperature, and then the potassium carbonate solution was removed and filtered. The filtered solid was washed with ethanol to give compound 2 (18 g, 85% yield).

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

Synthesis confirmation data of the above compound 2 are shown in FIG.

PREPARATION EXAMPLE 3 Synthesis of Compound 3

1) Synthesis of Compound 3-A

 Compound 3-A was prepared in the same manner as compound 1-A except that (3-bromo-5-chlorophenyl) boronic acid was used in place of (3,5-dichlorophenyl) boronic acid.

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

2) Synthesis of Compound 3-B

The compound 3-A (20 g, 40.1 mmol) and 1-naphthalenylboronic acid (7.6 g, 44.1 mmol) were dissolved in 1.4-dioxane under a nitrogen stream, and then potassium phosphate (17.0 g, 80.2 mmol) Respectively. The catalyst Pd (PPh3) 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 then the potassium phosphate solution was removed and filtered. The filtered solid was washed with ethanol to give compound 3-B (18 g, yield 82%).

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 are 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 in place of (4- (1-naphthalenyl) phenyl)

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

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

PREPARATION EXAMPLE 5 Synthesis of Compound 5

1) Synthesis of Compound 5-B

Compound 5-B was prepared in the same manner 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

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

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

Synthesis confirmation data of Compound 5 are 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 in place of (4- (2-naphthalenyl)

 MS [M + H] &lt; + &gt; = 714

Synthesis confirmation data of the compound 6 are 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] -4-chloro-6-phenyl-1,3,5- Synthesis of Compound 8-A was carried out in the same manner as Compound 1-A, except that 4-chloro-6-phenyl-1,3,5-triazine was used.

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

2) Synthesis of Compound 8-B

Compound 8-B was prepared in the same manner as compound 1-B, except that compound 8-A was used in place 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 are 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

The synthesis confirmation data of the compound 10 are shown in FIG.

PREPARATION EXAMPLE 11 Synthesis of Compound 11

1) Synthesis of Compound 11-A

2 - ([1,1'-biphenyl] -4-chloro-6-phenyl-1,3,5- Synthesis of Compound 11-A was carried out in the same manner as Compound 3-A, except that 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 in the same manner as compound 3-B, except that 11-A was used in place 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 above compound 11 are shown in Fig.

PREPARATION EXAMPLE 12 Synthesis of Compound 12

 Compound 12 was prepared in the same manner 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 are shown in FIG.

PREPARATION EXAMPLE 13 Synthesis of Compound 13

1) Synthesis of Compound 13-B

Compound 13-B was prepared in the same manner as Compound 5-B, except that Compound 11-A was used in place of Compound 3-A.

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

2) Synthesis of Compound 13

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

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

The synthesis confirmation data of the compound 13 are 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 in place of (4- (naphthalen-

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

PREPARATION EXAMPLE 16 Synthesis of Compound 16

1) Synthesis of Compound 16-A

Chloro-4- (dibenzo [b, d] furan-2-yl) -4-chloro- -1-yl) -6-phenyl-1,3,5-triazine, the compound 16-A was prepared in the same manner as the compound 1-A.

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

2) Synthesis of Compound 16-B

Compound 16-B was prepared in the same manner as compound 1-B, except that compound 16-A was used in place 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 are shown in Fig.

Production Example 17 Synthesis of Compound 17

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

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

The synthesis confirmation data of the above compound 17 is shown in FIG.

Production Example 18 Synthesis of Compound 18

1) Synthesis of Compound 18-A

Chloro-4- (dibenzo [b, d] furan-2-yl) -4-chloro- -1-yl) -6-phenyl-1,3,5-triazine, the compound 18-A was prepared in the same manner as the compound 3-A.

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

2) Synthesis of Compound 18-B

Compound 18-B was prepared in the same manner as compound 3-B, except that compound 18-A was used in place 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

Production Example 19 Synthesis of Compound 19

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

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

Production Example 20 Synthesis of Compound 20

1) Synthesis of Compound 20-B

 Compound 20-B was prepared in the same manner 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

The synthesis confirmation data of the compound 20 are shown in FIG.

PREPARATION EXAMPLE 21 Synthesis of Compound 21

 Compound 21 was prepared in the same manner as Compound 20, except that (4- (naphthalen-1-yl) phenyl) boronic acid was used in place of (4- (naphthalen-

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

The 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 in the same manner as compound 1-A except that (2,5-dichlorophenyl) boronic acid was used in place of (2,5-dichlorophenyl) boronic acid.

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

2) Synthesis of Compound 23-B

 Compound 23-B was prepared in the same manner as compound 1-B, except that compound 23-A was used in place of compound 1-A.

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

3) Synthesis of Compound 23

 Compound 23 was prepared in the same manner as Compound 1, except that Compound 23-B was used in place 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 EXAMPLE 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

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

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

2) Synthesis of Compound 26-B

 Compound 26-B was prepared in the same manner as compound 3-B except that compound 26-A was used in place of compound 3-A.

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

3) Synthesis of Compound 26

Except that Compound 26-B was used instead of Compound 3-B and (4- (phenanthrene-9-yl) phenyl) boronic acid was used instead of (4- (naphthalen- , &Lt; / RTI &gt;

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

< Example >

Example 1

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

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

Subsequently, the following compounds [BH] and [BD] were vapor-deposited at a weight ratio of 25: 1 on the hole transport layer to a thickness of 200 ANGSTROM to form a light emitting layer. Compound 1 and [LiQ] (Lithiumquinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injecting and transporting layer having a thickness of 350 Å. Lithium fluoride (LiF) and aluminum having a thickness of 1,000 Å were sequentially deposited on the electron injecting and transporting layer to form a cathode.

The deposition rate of the organic material was maintained at 0.4 to 0.9 Å / sec, the lithium fluoride at the cathode was maintained at a deposition rate of 0.3 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec. ^-7 to &lt; 5 10 ^{&lt; -8} &gt; torr. Thus, an organic light emitting device was fabricated.

Example 2

An organic light emitting device was fabricated 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 fabricated 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 fabricated 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 prepared 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 fabricated 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 fabricated 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 fabricated 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 prepared 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 prepared 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 fabricated 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 prepared 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 fabricated 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 fabricated 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 luminescent device was fabricated 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 fabricated 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 fabricated 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 fabricated 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 fabricated 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 prepared 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 fabricated 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 fabricated 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 fabricated 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 prepared 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 fabricated 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 fabricated in the same manner as in Example 1, except that the following compound ET1 was used instead of the compound 1 in Example 1.

Comparative Example 2

An organic light emitting device was fabricated in the same manner as in Example 1, except that the following compound ET2 was used instead of the compound 1 in Example 1.

Comparative Example 3

An organic light emitting device was fabricated in the same manner as in Example 1, except that the following compound ET3 was used instead of the compound 1 in Example 1.

Comparative Example 4

An organic luminescent device was fabricated in the same manner as in Example 1, except that the following compound ET4 was used instead of the compound 1 in Example 1.

Comparative Example 5

An organic light emitting device was fabricated in the same manner as in Example 1, except that the following compound ET5 was used instead of the compound 1 in Example 1.

Comparative Example 6

An organic light emitting device was fabricated in the same manner as in Example 1, except that the following compound ET6 was used instead of the compound 1 in Example 1.

The Examples 1 to 14, 16 to 26 and Comparative Examples 1 to the organic light-emitting device 6 at a current density of 10mA / cm ² were measured drive voltage and light emission efficiency, 90 initial luminance compared with a current density of 20mA / cm ² % (LT90) was measured. The results are shown in Table 1 below.

Example 10 mA / cm &lt; ² &gt; compound Voltage (V) Current efficiency (cd / A) The color coordinates (x, y) Life Time (T90 at 20 mA / 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 Chemical Formula 1 according to one embodiment of the present invention can be used for an organic layer capable of simultaneously injecting electrons and transporting electrons of an organic light emitting device.

In particular, the compounds ET2 and ET6 of Comparative Examples 2 and 6 confirmed that Ar1 and Ar2 of the present invention exhibited higher voltage, lower efficiency and lower lifetime than the same compounds, and the compounds ET3 and ET4 of Comparative Examples 3 and 4 The compound having a substituent not included in the definition of Y of the present invention exhibited higher voltage, lower efficiency and lower lifetime than the compounds of Examples 1 to 14 and 16 to 26.

1: substrate
2: anode
3: light emitting layer
4: cathode
5: Hole injection layer
6: hole transport layer
7: Electron transport layer

Claims (10)

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein the organic compound layer comprises an electron transport layer comprising a compound represented by the following formula 1 and lithium quinolate Organic Light Emitting Device:
[Chemical Formula 1]

In Formula 1, at least one of X1 to X3 is N and the other is CR,
R are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; An alkyl group having 1 to 20 carbon atoms; A cycloalkyl group having 3 to 20 carbon atoms; A monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a 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; An alkyl group having 1 to 20 carbon atoms; A monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a monocyclic or polycyclic heterocyclic group having 3 to 20 carbon atoms,
L is a direct bond; A monocyclic or polycyclic divalent to hexavalent aryl group having 6 to 20 carbon atoms; Or a monocyclic to polycyclic divalent to hexavalent heteroaryl group having 3 to 20 carbon atoms,
Y is a naphthyl group; Phenanthrene; A dimethylfluorene group; Anthracene group; Triphenylene group; Pyrene; Tetracene; Chrysene; Perylene group; Or a fluoranthene group,
n is an integer of 2 to 5, and plural Ys are the same or different. 2. The compound according to claim 1, wherein L is a divalent to tetravalent phenyl group; A bivalent to tetravalent biphenyl group; A divalent to tetravalent naphthyl group; A phenanthrene group having 2 to 4 valences; A divalent to tetravalent carbazole group; A divalent to tetravalent pyridine group; A divalent to tetravalent pyrimidine group; A triazine group of 2 or 3; A quinoline group having 2 to 4 valences; A divalent to tetravalent dibenzofurane group; Or a divalent to tetravalent dibenzothiophene group. 2. The compound according to claim 1, wherein L is a trivalent phenyl group; Or a trivalent biphenyl group. The organic light-emitting device according to claim 1, wherein the plurality of Y's are the same. The organic light-emitting device according to claim 1, wherein the plurality of Ys are different. [2] The compound according to claim 1, wherein Ar1 and Ar2 are different from each other and are each independently a phenyl group; Biphenyl group; Phenanthrene; A dimethylfluorene group; A dibenzofurane group; A dibenzothiophene group; Naphthyl group; Or a pyrene group. The organic electroluminescent device according to claim 1, wherein Y is a naphthyl group or a phenanthrene group. The organic electroluminescent device according to claim 1, wherein the compound represented by Formula 1 is any one selected from the following structural formulas:

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