KR20190053809A - Organic light emitting device - Google Patents

Abstract

The present invention provides a novel heterocyclic compound and an organic light-emitting device using the same. The organic light-emitting device according to an embodiment of the present invention includes: a negative electrode; a positive electrode; and at least one organic material layer provided between the negative electrode and the positive electrode. The at least one organic material layer includes at least one compound selected from a group consisting of compounds represented by chemical formula 1 and 2. The organic light-emitting device according to the present invention may lower the driving voltage and improve the efficiency, thermal stability and lifetime.

Description

[0001] The present invention relates to an organic light emitting device,

The present invention relates to an organic light emitting device capable of lowering a driving voltage and improving efficiency, thermal stability and lifetime.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent characteristics of luminance, driving voltage and response speed, and much research has been conducted.

The organic light emitting device generally has a structure including an anode and a cathode, and an organic layer provided between the anode and the cathode. The organic material layer may have a multilayer structure composed of different materials in order to improve the efficiency and stability of the organic light emitting device. For example, the organic material layer 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.

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

Korean Patent Publication No. 10-2000-0051826

The present invention relates to an organic light emitting device capable of lowering a driving voltage and improving efficiency, thermal stability and lifetime.

The present invention relates to a negative electrode, anode; And at least one organic material layer provided between the cathode and the anode,

The organic layer having one or more layers includes at least one compound selected from the group consisting of compounds represented by the following formulas (1) and (2).

[Chemical Formula 1]

(2)

In the above Formulas 1 and 2,

X ₁ and X ₂ are each independently N or CR 'with the proviso that at least one of them is N,

R 'is hydrogen; Or substituted or unsubstituted C _1-60 alkyl,

R ₁ to R ₄ are each independently hydrogen; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _6-60 aryl; C _2-60 heteroaryl comprising at least one of substituted or unsubstituted O, N, Si and S; Substituted or unsubstituted C _1-60 alkoxy; A substituted or unsubstituted C _1-60 ether; Cyano; Florin; Trifluoromethyl; Trifluoromethoxy; Or trimethylsilyl,

A and B are each independently hydrogen; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _6-60 aryl; C _2-60 heteroaryl comprising at least one of substituted or unsubstituted O, N, Si and S; Substituted or unsubstituted C _1-60 alkoxy; A substituted or unsubstituted C _1-60 ether; Cyano; Florin; Trifluoromethyl; Trifluoromethoxy; Or trimethylsilyl.

The organic light emitting device including the compound represented by Chemical Formula 1 and / or Chemical Formula 2 in the organic material layer can lower the driving voltage, improve the efficiency, thermal stability and lifetime.

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.
FIG. 2 is a cross-sectional view of a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, an electron blocking layer 7, a light emitting layer 3, an electron transporting layer 8, And a cathode (4).
FIG. 3 is a cross-sectional view of a substrate 1, an anode 2, a hole injecting layer 5, a first hole transporting layer 10, an electron blocking layer 7, a first light emitting layer 11, a first electron transporting layer 12, An organic light emitting element (organic electroluminescent element) 14 composed of an N-type charge generation layer 13, a P-type charge generation layer 14, a second hole transporting layer 15, a second light emitting layer 16, a second electron transporting layer 17, Fig.

Hereinafter, the present invention will be described in detail in order to facilitate understanding of the present invention.

는 다른 치환기에 연결되는 결합을 의미한다. In the present specification,

Quot; means a bond connected to another substituent.

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; Cycloalkyl groups; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Arylphosphine groups; Or a heterocyclic group containing at least one of N, O and S atoms, or a substituted or unsubstituted group in which at least two of the above-exemplified substituents are connected to each other . For example, the "substituent group 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 carbon number of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But are not limited thereto.

In the present specification, the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

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, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl and 5-methylhexyl.

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 the present 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- 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.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

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, Si and S 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 benzoimidazole 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 aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group and the arylamine group is the same as the aforementioned aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the alkyl group described above. In the present specification, the heteroaryl among the heteroarylamines can be applied to the aforementioned heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group. 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 the present specification, the description of the above-mentioned aryl group or cycloalkyl group can be applied except that the hydrocarbon ring is not a monovalent group and two substituents are bonded to each other. In the present specification, the description of the above-mentioned heterocyclic group can be applied except that the heterocyclic ring is not a monovalent group and two substituents are bonded to each other.

Hereinafter, various embodiments of the present invention will be described in detail with reference to the accompanying drawings.

1 to 3 show examples of the organic light emitting device of the present invention.

Referring to FIG. 1, the organic light emitting device of the present invention may include a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.

2, the organic light emitting device of the present invention includes a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, an electron blocking layer 7, a light emitting layer 3, (8), an electron injection layer (9), and a cathode (4).

3, the organic light emitting device of the present invention includes a substrate 1, an anode 2, a hole injecting layer 5, a first hole transporting layer 10, an electron blocking layer 7, a first light emitting layer 11 The first electron transport layer 12, the N-type charge generation layer 13, the P-type charge generation layer 14, the second hole transport layer 15, the second light emitting layer 16, the second electron transport layer 17, And a cathode (4).

The anode 2 may be any one of ITO (Indium Tin Oxide), IZO (Indium Zinc Oxide), and ZnO (Zinc Oxide) having high work function as an electrode for injecting holes. When the anode is a reflective electrode, the anode may further include a reflective layer formed of any one of aluminum (Al), silver (Ag), and nickel (Ni) below the layer made of ITO, IZO or ZnO.

At least one organic layer may be formed on the anode 2.

The organic material layer of the present invention may include at least one compound selected from the group consisting of compounds represented by the following formulas (1) and (2).

[Chemical Formula 1]

(2)

In the above Formulas 1 and 2,

X ₁ and X ₂ are each independently N or CR 'with the proviso that at least one of them is N,

R 'is hydrogen; Or substituted or unsubstituted C _1-60 alkyl,

R ₁ to R ₄ are each independently hydrogen; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _6-60 aryl; C _2-60 heteroaryl comprising at least one of substituted or unsubstituted O, N, Si and S; Substituted or unsubstituted C _1-60 alkoxy; A substituted or unsubstituted C _1-60 ether; Cyano; Florin; Trifluoromethyl; Trifluoromethoxy; Or trimethylsilyl,

A and B are each independently hydrogen; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _6-60 aryl; C _2-60 heteroaryl comprising at least one of substituted or unsubstituted O, N, Si and S; Substituted or unsubstituted C _1-60 alkoxy; A substituted or unsubstituted C _1-60 ether; Cyano; Florin; Trifluoromethyl; Trifluoromethoxy; Or trimethylsilyl.

The organic material layer may have a multi-layer structure composed of different materials to enhance efficiency and stability of the organic light emitting device. For example, the organic material layer may include an electron injection layer 9, an electron transport layer 8, an electron injection and electron transport layer, A hole injection layer 5, a hole transport layer 6, a light emitting layer 3, and the like.

In addition, the organic material layer may include two or more light emitting layers 3, and a charge generating layer including an N-type electron generating layer 13 and a P-type hole generating layer 14 may be provided between the two or more light emitting layers .

Preferably, at least one compound selected from the group consisting of the compounds represented by the formulas (1) and (2) may be included in the hole injection layer (5). For example, the compound may be included as a dopant in the hole injection layer.

Further, at least one compound selected from the group consisting of the compounds represented by Chemical Formulas 1 and 2 may be included in the P-type hole generating layer 14, for example, the compound may be included as a dopant of the P- have.

The compound included in the hole injection layer 5 should contain a strong electron withdrawing substituent. However, such a compound is difficult to synthesize due to the electron withdrawing substituent, and is poor in heat and deposition stability. However, the compound of the present invention can easily synthesize and deposit compounds by including cyclopentapyridine as a core that can ensure process stability such as heat or vapor deposition. In addition, since the compound of the present invention includes an electron withdrawing substituent bonded to the core to increase the electron affinity, the amount and the concentration of holes generated in the adjacent hole injection layer and the hole transport layer 6 are increased, .

On the other hand, the hole transport layer 6 is a layer which receives holes from the hole injection layer 5 and transports holes to the light emitting layer 3. [ Therefore, a hole transporting material included in the hole transporting layer must use a material capable of transporting holes from the anode 2 or the hole injecting layer to the light emitting layer. Therefore, a material having high mobility to holes is required.

The formula 1 may be any one selected from compounds represented by the following formulas 1-1 to 1-3.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 through 1-3,

R ₁ to R ₄ are each independently hydrogen; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _6-60 aryl; C _2-60 heteroaryl comprising at least one of substituted or unsubstituted O, N, Si and S; Substituted or unsubstituted C _1-60 alkoxy; A substituted or unsubstituted C _1-60 ether; Cyano; Florin; Trifluoromethyl; Trifluoromethoxy; Or trimethylsilyl,

A and B are each independently hydrogen; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _6-60 aryl; C _2-60 heteroaryl comprising at least one of substituted or unsubstituted O, N, Si and S; Substituted or unsubstituted C _1-60 alkoxy; A substituted or unsubstituted C _1-60 ether; Cyano; Florin; Trifluoromethyl; Trifluoromethoxy; Or trimethylsilyl.

The formula (2) may be a compound represented by the following formula (2-1) or (2-2).

[Formula 2-1]

[Formula 2-2]

In the above Formulas (2-1) and (2-2)

R ₁ to R ₄ are each independently hydrogen; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _6-60 aryl; C _2-60 heteroaryl comprising at least one of substituted or unsubstituted O, N, Si and S; Substituted or unsubstituted C _1-60 alkoxy; A substituted or unsubstituted C _1-60 ether; Cyano; Florin; Trifluoromethyl; Trifluoromethoxy; Or trimethylsilyl,

A and B are each independently hydrogen; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _6-60 aryl; C _2-60 heteroaryl comprising at least one of substituted or unsubstituted O, N, Si and S; Substituted or unsubstituted C _1-60 alkoxy; A substituted or unsubstituted C _1-60 ether; Cyano; Florin; Trifluoromethyl; Trifluoromethoxy; Or trimethylsilyl.

Preferably, A and B may be cyano.

Preferably, R ₂ and R ₃ can be cyano.

Preferably, R ₁ and R ₄ are each independently selected from the group consisting of

R ' ₁ to R' ₅ are each independently hydrogen, cyano, fluorine, trifluoromethyl, or trifluoromethoxy,

Y ₁ to Y ₃ are each independently N or CH, provided that at least one of these may be N.

The compound represented by Formula 1 may be any one selected from the group consisting of the following compounds.

The compound represented by the formula (1) can be prepared by the following reaction scheme (1).

[Reaction Scheme 1]

In the above Reaction Scheme 1, X ₁ , X ₂ , R ₁ to R ₄ , A and B are the same as defined in Formula 1 above.

The compound represented by Formula 2 may be any one selected from the group consisting of the following compounds.

The compound represented by the formula (2) can be prepared by the following reaction scheme (2).

[Reaction Scheme 2]

In the above Reaction Scheme 2, X ₁ , X ₂ , R ₁ to R ₄ , A and B are as defined in the above formula (1).

The organic layer may further include a compound represented by the following formula (3).

(3)

In Formula 3,

X, Y and Z are each independently a substituted or unsubstituted C _6-60 aryl; Or C _2-60 heteroaryl comprising at least one of substituted or unsubstituted O, N, Si and S;

The compound represented by Formula 3 may be any one selected from the group consisting of the following compounds.

In the organic light emitting device of the present invention, the hole injection layer 5 may be formed on the anode 2. The hole injecting layer is made of a hole injecting material. The hole injecting material has a hole injecting effect on the anode 2, a hole injecting effect on the light emitting layer 3 or a light emitting material due to its ability to transport holes, A compound which prevents migration of excitons generated in the light emitting layer to the electron injecting layer or the electron injecting material and that has excellent thin film forming ability is preferable. It is preferred 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.

A hole transport layer 6 may be formed on the hole injection layer 5 and a light emission layer 3 may be formed on the hole transport layer 6. The light emitting layer may emit red (R), green (G), or blue (B) light, and may be formed of a fluorescent material or a phosphorescent material.

The organic light emitting device according to the present invention may be formed by a material and a method known in the art except that at least one of the organic material layers includes at least one compound selected from the group consisting of the compounds represented by the above formulas 1 and 2 ≪ / RTI > In addition, 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.

For example, the organic light emitting device according to the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate 1. At this time, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate by a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form the anode 2 ), An organic material layer including a hole injection layer 5, a hole transporting layer 6, a light emitting layer 3 and an electron transporting layer 8 is formed thereon, ≪ / RTI > 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 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition 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 can be manufactured by sequentially depositing an organic material layer and a cathode material on a substrate 1 from a cathode material (WO 2003/012890). However, the manufacturing method is not limited thereto.

In one example, the first electrode is an anode 2, the second electrode is a cathode 4, or 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 to the organic material layer. Specific examples of the positive electrode material 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 the ability to transport holes, so that it has a hole injecting effect in the anode 2, an excellent hole injecting effect on the light emitting layer (3) Which prevents the migration of excitons generated in the light emitting layer to the electron injection layer or the electron injection material and is also excellent in the ability to form a thin film. It is preferred 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 6 is a layer that receives holes from the hole injection layer 5 and transports holes to the light emitting layer 3. The hole transport material transports holes from the anode 2 or the hole injection layer to the light emitting layer It is preferable to include a compound that can give the compound.

The light emitting material is a material capable of emitting light in a visible light region by transporting and combining holes and electrons from the hole transport layer 6 and the electron transport layer 8, and is preferably a material having good quantum efficiency for fluorescence or phosphorescence Do. 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 3 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 the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

The electron transporting material is a layer that transports electrons from the electron injection layer to the electron transport layer and transports electrons from the electron injection layer to the light emitting layer 3. The electron transporting material is a material capable of transferring electrons from the cathode 4 to the light emitting layer, A material having high mobility 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 transport layer 8 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 having a low work function followed by an aluminum layer or a 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 and has the ability to transport electrons and has an electron injection effect from the cathode 4 and an electron injection effect to the light emitting layer 3 or the light emitting material, A compound which prevents migration of generated excitons to the hole injection layer 5 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 nitrogen-containing 5-membered ring derivative, 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- 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 organic light emitting device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

Best Mode for Carrying Out the Invention Hereinafter, preferred embodiments are shown to facilitate understanding of the present invention. However, the following examples are intended to illustrate the present invention without limiting it thereto.

Manufacturing example  1: Synthesis of compound 1

Step 1) Synthesis of Compound 1-1

2,2 '- (3,5-dibromopyridine-2,6-diyl) diacetonitrile (50 g, 15.87 mmol) was added to a 1000 ml round-bottomed flask with copper iodide (2.4 g, 1.269 mmol) Amine (54.5 ml, 63.49 mmol) and tetrakis (triphenylphosphine) palladium (0) (7.3 g, 0.634 mmol) were dissolved in toluene (500 ml). After heating and stirring for 10 minutes, 1-ethynyl-3,5-bis (trifluoromethyl) benzene (84.2 ml, 47.61 mmol) was dissolved in toluene (100 ml) and slowly added dropwise.

After completion of the reaction, toluene was distilled at 80%, and anhydrous ethanol was added to solidify it. The mixture was filtered, dissolved in chloroform, stirred with water for 10 minutes, and the organic layer was collected, dried over anhydrous magnesium sulfate, and filtered. The organic layer was distilled off under reduced pressure, then solidified with absolute ethanol and filtered to obtain Compound 1-1 (60 g, yield 60%). MS [M + H] < ⁺ > = 629

Step 2) Synthesis of Compound 1-2

To a 500 ml round-bottomed flask was added compound 1-1 (30 g, 4.766 mmol), palladium chloride (PdCl ₂ ) (1.7 g, 0.953 mmol), silver hexafluoroantimonate (AgSbF ₆ ) (3.27 g, 0.953 mmol) Phenylsulfoxide (Ph ₂ SO) (57.8 g, 28.59 mmol) was dissolved in dichloroethylene (DCE) and stirred at 60 ° C for 12 hours. Cesium carbonate (Cs ₂ CO ₃ ) (9.532 mmol) Lt; / RTI > After extracting with dichloromethane (CH ₂ Cl ₂₎ After completion of the reaction dichloromethane (CH ₂ Cl ₂₎ to all into a 35% hydrochloric acid (HCl) and stirred for 2 hours after the shot. After extracting with dichloromethane / ammonium chloride aqueous solution (CH ₂ Cl _{2 /} aq. NH ₄ Cl), the organic layer was dried over anhydrous magnesium sulfate (MgSO ₄ ) and the organic layer was collected and concentrated under reduced pressure. Thereafter, the compound 1-2 (13 g, yield 41.5%) was obtained by column chromatography. MS [M + H] < ⁺ > = 657

Step 3) Synthesis of Compound 1

The compound 1-2 (10 g, 1.521 mmol), malononitrile (3.041 mmol), dichloromethane solvent and argon were stirred for 30 minutes in a 500 ml round bottom flask. After cooling to 0 ° C and stirring for 10 minutes, slowly add titanium tetrachloride (TiCl ₄ ) (8.45 ml, 6.084 mol), add pyridine (7.35 ml, 9.126 mmol) and slowly heat the mixture at 0 ° C And the mixture was stirred at room temperature for 2 hours. After extraction with dichloromethane / ammonium chloride aqueous solution (CH ₂ Cl _{2 /} aq. NH ₄ Cl), the organic layer was dried over anhydrous magnesium sulfate and the organic layer was collected and distilled under reduced pressure to obtain Compound 1 (6 g, yield 52.35%). MS [M + H] < ⁺ > = 753

Manufacturing example  2: Synthesis of Compound 2

Step 1) Synthesis of Compound 2-1

2,2 '- (2,6-dibromopyridine-3,5-diyl) diacetonitrile (50 g, 15.87 mmol) was added to a 1000 ml round bottom flask with a mixture of copper idide (2.4 g, 1.269 mmol), isopropylamine (54.5 ml, 63.49 mmol) and tetrakis (triphenylphosphine) palladium (0) (7.3 g, 0.634 mmol) were dissolved in toluene (500 ml). After heating and stirring for 10 minutes, 4-ethynyl-2- (trifluoromethyl) benzonitrile (92.9 g, 47.61 mmol) was dissolved in toluene (100 ml) and slowly added dropwise. After completion of the reaction, toluene was distilled at 80%, and anhydrous ethanol was added to solidify it. Filtered, dissolved in chloroform, and stirred for 10 minutes with water. The organic layer was collected, dried over anhydrous magnesium sulfate and filtered. The organic layer was distilled off under reduced pressure, then solidified with absolute ethanol and filtered to obtain Compound 2-1 (53 g, yield 61.6%). MS [M + H] < ⁺ > = 543

Step 2) Synthesis of Compound 2

Compound 2 (4 g, yield: 69%) was obtained in the same manner as in Steps 2 and 3 of Preparation Example 1, except that Compound 2-1 thus prepared was used instead of Compound 1-1. MS [M + H] < ⁺ > = 667

Manufacturing example  3: Synthesis of Compound 3

Step 1) Synthesis of Compound 3-1

2,2 '- (3,5-dibromopyrazine-2,6-diyl) diacetonitrile (50 g, 15.82 mmol) was added to a 1000 ml round bottom flask with a mixture of copper iodide (2.4 g, 1.269 mmol) Amine (54.5 ml, 63.49 mmol) and tetrakis (triphenylphosphine) palladium (0) (7.3 g, 0.634 mmol) were dissolved in toluene (500 ml). After heating and stirring for 10 minutes, 4-ethynyl-2,6-difluorobenzonitrile (77.4 g, 47.46 mmol) was dissolved in toluene (100 ml) and slowly added dropwise. After completion of the reaction, toluene was distilled at 80%, and anhydrous ethanol was added to solidify it. Filtered, dissolved in chloroform, and stirred for 10 minutes with water. The organic layer was collected, dried over anhydrous magnesium sulfate, and filtered. The organic layer was distilled off under reduced pressure, then solidified with absolute ethanol and filtered to obtain Compound 3-1 (48 g, yield 63%). MS [M + H] < ⁺ > = 480

Step 2) Synthesis of Compound 3

Compound 3 (3.2 g, yield 71%) was obtained in the same manner as in Steps 2 and 3 of Preparation Example 1, except that Compound 3-1 was used instead of Compound 1-1. MS [M + H] < ⁺ > = 604

Manufacturing example  4: Synthesis of compound 4

Step 1) Synthesis of compound 4-1

2,2 '- (3,6-dibromopyridine-2,5-diyl) diacetonitrile (50 g, 15.87 mmol) was added to a 1000 ml round-bottomed flask with copper iodide (2.4 g, 1.269 mmol) Amine (54.5 ml, 63.49 mmol) and tetrakis (triphenylphosphine) palladium (0) (7.3 g, 0.634 mmol) were dissolved in toluene (500 ml). After heating and stirring for 10 minutes, 4-ethynyl-2- (trifluoromethoxy) benzonitrile (100.5 g, 47.62 mmol) was dissolved in toluene (100 ml) and slowly added dropwise. After completion of the reaction, toluene was distilled at 80%, and anhydrous ethanol was added to solidify it. The organic layer was collected by filtration and dried over anhydrous magnesium sulfate. The organic layer was distilled off under reduced pressure, then solidified with absolute ethanol and filtered to obtain Compound 4-1 (52 g, yield 57%). %). MS [M + H] < ⁺ > = 575

Step 2) Synthesis of Compound 4-2

Compound 500ml round bottom flask was charged 4-1 (30g, 5.213mmol), palladium chloride _{(PdCl 2) (1.84g, 1.042mmol} ), silver hexafluoroantimonate _{(AgSbF 6) (3.58g, 1.042mmol} ), di After dissolving phenylsulfoxide (Ph ₂ SO) (12.6 g, 6.252 mmol) in dichloroethylene (DCE) and stirring at 60 ° C for 12 hours, cesium carbonate (Cs ₂ CO ₃ ) (6.79 g, 2.084 mmol) And the mixture was stirred for 12 hours. After extracting with dichloromethane (CH ₂ Cl ₂₎ After completion of the reaction dichloromethane (CH ₂ Cl ₂₎ to all into a 35% hydrochloric acid (HCl) and stirred for 2 hours after the shot. Purification of the organic layer after extraction with methane / ammonium chloride solution (CH2Cl2 / aq.NH ₄ Cl) and concentrated under reduced pressure to collect the organic layer was dried over anhydrous magnesium sulfate (MgSO _4). Thereafter, column chromatography was used to obtain Compound 4-2 (13 g, yield 43.6%). MS [M + H] < ⁺ > = 603

Step 3) Synthesis of Compound 4

The compound 4-2 (10 g, 1.658 mmol), malononitrile (2.19 g, 3.316 mmol), dichloromethane solvent and argon were stirred for 30 minutes in a 500 ml round bottom flask. It was cooled to 0 ° C and then stirred for 10 minutes after the semi-put of titanium tetrachloride _{(TiCl 4) (7.27ml, 6.632mol} ) slowly into a pyridine (pyridine) (10.68ml, 13.264mmol) at room temperature slowly at 0 ° C And the mixture was stirred at room temperature for 2 hours. Thereafter, the organic layer was extracted with dichloromethane / ammonium chloride aqueous solution (CH ₂ Cl _{2 /} aq. NH ₄ Cl), and the organic layer was dried over anhydrous magnesium sulfate. The organic layer was collected and distilled under reduced pressure to obtain Compound 4 (7 g, 60.39%). MS [M + H] < ⁺ > = 699

Manufacturing example  5: Synthesis of Compound 5

Step 1) Synthesis of Compound 5-1

2,2 '- (2,6-dibromopyridine-3,5-diyl) diacetonitrile (50 g, 15.87 mmol) was added to a 1000 ml round-bottomed flask with a solution of copper iodide (2.4 g, 1.269 mmol) Amine (54.5 ml, 63.49 mmol) and tetrakis (triphenylphosphine) palladium (0) (7.3 g, 0.634 mmol) were dissolved in toluene (500 ml). After heating and stirring for 10 minutes, 3-ethynyl-5- (trifluoromethyl) benzonitrile (92.9 g, 47.61 mmol) was dissolved in toluene (100 ml) and slowly added dropwise. After completion of the reaction, toluene was distilled at 80%, and anhydrous ethanol was added to solidify it. The organic layer was collected by filtration and dried over anhydrous magnesium sulfate. The organic layer was distilled under reduced pressure, then solidified with anhydrous ethanol and filtered to obtain Compound 5-1 (50 g, yield 58.0%). MS [M + H] < ⁺ > = 543

Step 2) Synthesis of Compound 5

Compound 5 (4 g, yield: 69%) was obtained in the same manner as in Steps 2 and 3 of Preparation Example 4, except that Compound 5-1 thus prepared was used instead of Compound 4-1. MS [M + H] < ⁺ > = 667

Manufacturing example  6: Compound 6 of  synthesis

Step 1) Synthesis of Compound 6-1

2,2 '- (3,6-dibromopyrazine-2,5-diyl) diacetonitrile (50 g, 15.82 mmol) was added to a 1000 ml round bottomed flask with capper iodide (2.4 g, 1.269 mmol) Amine (54.5 ml, 63.49 mmol) and tetrakis (triphenylphosphine) palladium (0) (7.3 g, 0.634 mmol) were dissolved in toluene (500 ml). After heating and stirring for 10 minutes, 4-ethynyl-2,6-difluoro-bicarbonitrile (77.4 g, 47.46 mmol) was dissolved in toluene (100 ml) and slowly added dropwise. After completion of the reaction, toluene was distilled at 80%, and anhydrous ethanol was added to solidify it. The organic layer was collected by filtration and dried over anhydrous magnesium sulfate. The organic layer was distilled under reduced pressure, then solidified with absolute ethanol and filtered to obtain Compound 6-1 (50 g, yield 65.78%). MS [M + H] < ⁺ > = 480

Step 2) Synthesis of Compound 6-2

Compound 6 (3.5 g, yield 72%) was obtained in the same manner as in Steps 2 and 3 of Preparation Example 4, except that Compound 6-1 thus prepared was used instead of Compound 4-1. MS [M + H] < ⁺ > = 604

Example  1-1

의 두께로 박막 코팅된 유리기판을 세제에 녹인 증류수에 넣고 초음파로 세척하였다. 이때 세제로는 피셔사(Fischer Co.)의 Decon™ CON705 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 0.22㎛ sterilizing filter로 2차 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필 알코올, 아세톤 및 메탄올의 용제로 각각 10분간 초음파 세척하고, 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후, 진공 증착기로 기판을 수송시켰다.ITO (Indium Tin Oxide) is 1,400

Coated glass substrate was placed in distilled water dissolved in detergent and washed with ultrasonic waves. As a detergent, Decon (TM) CON705 product of Fischer Co. was used, and distilled water secondaryly filtered with a 0.22 μm sterilizing filter manufactured by 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 for 10 minutes, dried, and then transported to a plasma cleaner. The substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

The HT-A and the compound 1 (dopant) were thermally vacuum deposited to a thickness of 100 Å at a weight ratio of 95: 5 on the prepared ITO transparent electrode to form a hole injection layer. Then, only the HT-A material was deposited to a thickness of 1100 Å, To form a transport layer. A compound represented by EB-A as an electron blocking layer was thermally vacuum deposited thereon to a thickness of 50 Å. Subsequently, the following compounds represented by the following formulas BH-A and BD-A were vacuum-deposited to a thickness of 200 Å at a weight ratio of 96: 4. Next, a compound represented by ET-A and Liq as the electron transporting layer was thermally vacuum-deposited to a thickness of 360 Å at a weight ratio of 1: 1, and then a compound represented by the following Liq was vacuum deposited to a thickness of 5 Å to form an electron injecting layer Respectively. Magnesium and silver were sequentially deposited on the electron injection layer at a weight ratio of 10: 1 to a thickness of 220 Å and aluminum to a thickness of 1000 to form a cathode, thereby preparing an organic light emitting device.

Example  1-2 to 1-6 and Comparative Example  1-1 to 1-4

An organic light emitting device was fabricated in the same manner as in Example 1-1, except that the compounds described in the following Table 1 were used instead of HT-A and Compound 1 in Example 1-1. The parentheses in Table 1 correspond to the weight ratio of the compounds, respectively, and the compounds with lower contents correspond to the dopants.

Table 2 shows the results obtained by measuring the voltage and efficiency when a current density of 10 mA / cm < ² > was applied to the organic light emitting device manufactured in the above Examples and Comparative Examples.

Hole injection layer Voltage (V) Efficiency (cd / A) Example 1-1 HT-A: Compound 1 (95: 5) 4.83 6.21 Examples 1-2 HT-A: Compound 2 (95: 5) 4.80 6.32 Example 1-3 HT-A: Compound 3 (95: 5) 4.55 6.57 Examples 1-4 HT-A: Compound 4 (95: 5) 4.21 6.80 Examples 1-5 HT-A: Compound 5 (95: 5) 4.20 6.82 Examples 1-6 HT-A: Compound 6 (95: 5) 3.92 7.23 Comparative Example 1-1 HT-A: HAT-CN (95: 5) 6.23 4.88 Comparative Example 1-2 HT-A 8.52 2.13 Comparative Example 1-3 HT-A: Compound A (95: 5) 5.12 5.85 Comparative Example 1-4 HT-A: Compound B (95: 5) 5.13 5.90

The respective compounds in Table 1 are as follows.

As shown in Table 1, when the compounds represented by the general formulas (1) and (2) of the present invention were used as dopants in the hole injection layer, it was confirmed that the voltage was remarkably low and the efficiency was remarkably excellent.

Example  2-1

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. At this time, Fischer Co. product was used as a detergent, and distilled water, which was secondly filtered with 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.

HAT-CN was thermally vacuum-deposited on the thus-prepared ITO transparent electrode to a thickness of 50 Å to form a hole injection layer, and then the following NPB was vacuum-deposited to a thickness of 100 Å to form a first hole transport layer. Subsequently, EB-B was vacuum deposited on the first hole transporting layer to a thickness of 100 ANGSTROM to form an electron blocking layer. Subsequently, the following YGH-A, YGH-B and YGD were vacuum deposited on the electron blocking layer to a thickness of 400 Å at a weight ratio of 2: 2: 1 to form a first light emitting layer. Then, a first electron transport layer was formed by vacuum-depositing the following ET-B on the first light emitting layer to a thickness of 250 ANGSTROM. Next, NCG and Li (Lithium) were vacuum deposited on the first electron transport layer at a weight ratio of 50: 1 to form an N-type charge generation layer having a thickness of 100 Å.

Subsequently, HT-A and Compound 1 (dopant) were vacuum-deposited at a weight ratio of 70:30 to form a P-type charge generation layer having a thickness of 100 Å. A vacuum hole deposition layer having a thickness of 800 Å was formed by HT- . Subsequently, the compound represented by the following formula BH-B and BD-B as the second light emitting layer was vacuum deposited at a weight ratio of 96: 4 to a thickness of 250 ANGSTROM.

A second electron transport layer was formed on the second light emitting layer by thermal vacuum deposition of a compound represented by ET-A and Liq at a weight ratio of 1: 1 to a thickness of 300 ANGSTROM. Then, LiF (Lithium Floride) To form a cathode, thereby preparing an organic light emitting device.

Example  2-2 to 2-18

An organic luminescent device was fabricated in the same manner as in Example 2-1, except that the compound shown in Table 2 was used instead of the compound 1 and HT-A in Example 2-1.

Comparative Example  2-1 to 2-9

An organic light emitting device was prepared in the same manner as in Example 2-1 except that the compounds described in Table 2 were used instead of HT-A and Compound 1 in Example 2-1. The parentheses in Table 1 correspond to the weight ratio of the compounds, respectively, and the compounds with lower contents correspond to the dopants.

Table 2 shows the results obtained by measuring the voltage and efficiency when a current density of 10 mA / cm < ² > was applied to the organic light emitting device manufactured in the above Examples and Comparative Examples.

P-type charge generation layer Voltage (V) Efficiency (cd / A) Example 2-1 HT-A: Compound 1 (70:30) 7.88 67.42 Example 2-2 HT-A: Compound 2 (70:30) 7.85 67.53 Example 2-3 HT-A: Compound 3 (70:30) 7.50 69.02 Examples 2-4 HT-A: Compound 4 (70:30) 7.62 68.02 Example 2-5 HT-A: Compound 5 (70:30) 7.63 68.16 Examples 2-6 HT-A: Compound 6 (70:30) 7.47 69.47 Examples 2-7 HT-B: Compound 1 (70:30) 8.02 67.42 Examples 2-8 HT-B: Compound 2 (70:30) 8.05 66.01 Examples 2-9 HT-B: Compound 3 (70:30) 8.02 65.38 Examples 2-10 HT-B: Compound 4 (70:30) 7.99 65.98 Examples 2-11 HT-B: Compound 5 (70:30) 8.05 65.23 Examples 2-12 HT-B: Compound 6 (70:30) 8.01 65.77 Examples 2-13 HT-C: Compound 1 (70:30) 7.78 68.32 Examples 2-14 HT-C: Compound 2 (70:30) 7.76 68.63 Examples 2-15 HT-C: Compound 3 (70:30) 7.73 69.02 Examples 2-16 HT-C: Compound 4 (70:30) 7.73 69.05 Examples 2-17 HT-C: Compound 5 (70:30) 7.72 69.09 Examples 2-18 HT-C: Compound 6 (70:30) 7.65 70.47 Comparative Example 2-1 HT-A: HAT-CN (70:30) 10.32 52.32 Comparative Example 2-2 HT-B: HAT-CN (70:30) 10.85 51.64 Comparative Example 2-5 HT-B: Compound A (70:30) 9.37 58.57 Comparative Example 2-6 HT-C: Compound A (70:30) 9.19 57.05 Comparative Example 2-7 HT-A: Compound B (70:30) 9.97 56.04 Comparative Example 2-6 HT-C: Compound A (70:30) 9.19 53.05 Comparative Example 2-9 HT-C: Compound B (70:30) 9.01 56.55

The respective compounds in Table 1 are as follows.

As shown in Table 2, when the compounds represented by the general formulas (1) and (2) of the present invention were used as dopants for the P-type charge generation layer, it was confirmed that the voltage was remarkably low and the efficiency was remarkably excellent.

1: substrate 2: anode
3: light emitting layer 4: cathode
5: Hole injection layer 6: Hole transport layer
7: electron blocking layer 8: electron transporting layer
9: electron injection layer 10: first hole transport layer
11: first light emitting layer 12: first electron transporting layer
13: N-type charge generation layer 14: P-type charge generation layer
15: second hole transporting layer 16: second light emitting layer
17: Second electron transport layer

Claims (14)

cathode; anode; And at least one organic material layer provided between the cathode and the anode,
Wherein the one or more organic layers include at least one compound selected from the group consisting of compounds represented by the following formulas (1) and (2):
[Chemical Formula 1]

(2)

In the above Formulas 1 and 2,
X ₁ and X ₂ are each independently N or CR 'with the proviso that at least one of them is N,
R 'is hydrogen; Or substituted or unsubstituted C _1-60 alkyl,
R ₁ to R ₄ are each independently hydrogen; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _6-60 aryl; C _2-60 heteroaryl comprising at least one of substituted or unsubstituted O, N, Si and S; Substituted or unsubstituted C _1-60 alkoxy; A substituted or unsubstituted C _1-60 ether; Cyano; Florin; Trifluoromethyl; Trifluoromethoxy; Or trimethylsilyl,
A and B are each independently hydrogen; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _6-60 aryl; C _2-60 heteroaryl comprising at least one of substituted or unsubstituted O, N, Si and S; Substituted or unsubstituted C _1-60 alkoxy; A substituted or unsubstituted C _1-60 ether; Cyano; Florin; Trifluoromethyl; Trifluoromethoxy; Or trimethylsilyl.
The method according to claim 1,
(1) is any one selected from compounds represented by the following formulas (1-1) to (1-3):
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 through 1-3,
R ₁ to R ₄ , A and B are the same as defined in claim 1.
The method according to claim 1,
Wherein the compound represented by Formula 2 is a compound represented by Formula 2-1 or 2-2:
[Formula 2-1]

[Formula 2-2]

In the above Formulas (2-1) and (2-2)
R ₁ to R ₄ , A and B are the same as defined in claim 1.
The method according to claim 1,
A and B are cyano, organic light-emitting device.
The method according to claim 1,
R ₂ and R ₃ are cyano.
The method according to claim 1,
R ₁ and R ₄ are each independently any one selected from the group consisting of

R ' ₁ to R' ₅ are each independently hydrogen, cyano, fluorine, trifluoromethyl, or trifluoromethoxy,
Y ₁ to Y ₃ are each independently N or CH, provided that at least one of them is N.
The method according to claim 1,
Wherein the compound represented by Formula 1 is any one selected from the group consisting of the following compounds:

The method according to claim 1,
Wherein the compound represented by Formula 2 is any one selected from the group consisting of the following compounds:

The method according to claim 1,
Wherein the organic layer includes at least one selected from the group consisting of an electron injection layer, an electron transport layer, an electron injection and electron transport layer, a hole injection layer, a hole transport layer, and a light emitting layer.
10. The method of claim 9,
Wherein the hole injection layer comprises the compound as a dopant.
The method according to claim 1,
Wherein the organic material layer includes two or more light emitting layers,
Wherein a charge generation layer including an N-type electron generating layer and a P-type hole generating layer is provided between the two or more light emitting layers.
12. The method of claim 11,
Wherein the P-type electron generating layer comprises the compound as a dopant.
12. The method of claim 11,
Wherein the organic layer further comprises a compound represented by the following Formula 3:
(3)

In Formula 3,
X, Y and Z are each independently a substituted or unsubstituted C _6-60 aryl; Or C _2-60 heteroaryl comprising at least one of substituted or unsubstituted O, N, Si and S;
14. The method of claim 13,
Wherein the compound represented by Formula 3 is any one selected from the group consisting of the following compounds:

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