KR20190003332A - Novel hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention relates to a novel heterocyclic compound capable of improving efficiency, and low driving voltage and/or lifespan characteristics in an organic light emitting device, and to an organic light emitting device using the same. The novel heterocyclic compound is represented by chemical formula 1. In the chemical formula 1, X_1 is O, S or NR_1, and R_1 is substituted or unsubstituted C_(1-60) alkyl.

Description

[0001] The present invention relates to novel heterocyclic compounds and organic light emitting devices using the same. More particularly,

The present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.

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 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. 10-2013-073537

The present invention relates to a novel heterocyclic compound compound and an organic light emitting device comprising the same.

The present invention provides a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

X ₁ is O, S or NR ₁ ,

R ₁ is a substituted or unsubstituted unsubstituted C _1-60 alkyl,

X ₂ , X ₃ and X ₄ are each independently N or CR ', provided that at least one of them is N,

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

Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-60 aryl or substituted or unsubstituted C _5-60 heteroaryl comprising at least one of N, O and S.

The present invention also provides a plasma display panel comprising: 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 the present invention.

The compound represented by the general formula (1) can be used as a material of an organic material layer of an organic light emitting device and can improve the efficiency, the driving voltage and / or the lifetime of the organic light emitting device. In particular, the compound represented by Formula 1 can be used as a hole injecting, hole transporting, hole injecting and transporting, light emitting, electron transporting, or electron injecting material.

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.

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

The present invention provides a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

X ₁ is O, S or NR ₁ ,

R ₁ is a substituted or unsubstituted unsubstituted C _1-60 alkyl,

X ₂ , X ₃ and X ₄ are each independently N or CR ', provided that at least one of them is N,

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

Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-60 aryl or substituted or unsubstituted C _5-60 heteroaryl comprising at least one of N, O and S.

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 furane group, a furyl 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 pyrazinopyrazinyl group, an isoquinoline group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, , An indole 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, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.

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.

Preferably, the compound represented by the formula (1) may be a compound represented by any one of the following formulas (1-1) to (1-4).

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In the above Formulas 1-1 to 1-4,

X ₁ , X ₂ , X ₃ , X ₄ , Ar ₁ and Ar ₂ are as defined above.

Preferably, the compound of Formula 1-1 may be any one of compounds represented by the following Formulas 1-1a to 1-1c.

[Formula 1-1a]

[Formula 1-1b]

[Formula 1-1c]

In the above formulas 1-1a to 1-1c,

X ₁ , X ₂ , X ₃ , X ₄ , Ar ₁ and Ar ₂ are as defined above.

Preferably, the compound represented by Formula 1-2 may be a compound represented by Formula 1-2a or 1-2b.

[Formula 1-2a]

[Formula 1-2b]

In the formula 1-2a or 1-2b,

X ₁ , X ₂ , X ₃ , X ₄ , Ar ₁ and Ar ₂ are as defined above.

Preferably, the compound of Formula 1-3 may be any one of compounds represented by Formulas 1-3a to 1-3c.

[Formula 1-3a]

[Formula 1-3b]

[Chemical Formula 1-3c]

In the above formulas 1-3a to 1-3c,

X ₁ , X ₂ , X ₃ , X ₄ , Ar ₁ and Ar ₂ are as defined above.

Preferably, the compound of Formula 1-4 may be a compound of Formula 1-4a or 1-4b.

[Chemical Formula 1-4a]

[Chemical Formula (1-4b)

In the formula 1-4a or 1-4b,

X ₁ , X ₂ , X ₃ , X ₄ , Ar ₁ and Ar ₂ are as defined above.

Preferably, Ar ₁ and Ar ₂ are each independently selected from the group consisting of

또는

일 수 있다.More preferably, Ar < _{1 >} and Ar < ₂ &

or

Lt; / RTI >

Preferably, the compound represented by the formula (1) may be any one selected from the group consisting of

The compound represented by the formula (1) can be prepared by the following reaction scheme (1). The above production method can be more specific in the production example to be described later.

[Reaction Scheme 1]

In the above Reaction Scheme 1, X ₁ , X ₂ , X ₃ , X ₄ , Ar ₁ and Ar ₂ are as defined above, and X represents a halogen atom, F, Cl, Br or I. The type of the reactor and the catalyst used in the above reaction formula can be appropriately selected. The above production method can be more specific in the production example to be described later.

Also, the present invention provides an organic light emitting device including the compound represented by Formula 1. In one embodiment, the present invention provides a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes a compound represented by Formula 1 do.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention 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.

The organic material layer may include a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting holes, and the hole injecting layer, the hole transporting layer, And a compound to be displayed.

In addition, the organic layer may include a light emitting layer, and the light emitting layer includes a compound represented by the general formula (1).

The organic material layer may include an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer includes the compound represented by the above formula (1).

In addition, the electron transporting layer, the electron injecting layer, or the layer which simultaneously injects electrons and transports electrons includes the compound represented by the above formula (1). In particular, the compound represented by Formula 1 according to the present invention has excellent thermal stability and has a deep HOMO level of 6.0 eV or more, a high triple energy (ET), and a hole stability. When the compound represented by the formula (1) is used for an organic layer capable of electron injection and electron transport at the same time, n-type dopants used in the art can be mixed and used.

The organic material layer may include a light emitting layer and an electron transporting layer, and the electron transporting layer may include a compound represented by the general formula (1).

In addition, the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting diode according to an embodiment of the present invention is illustrated in FIGS.

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. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer.

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. In such a structure, the compound represented by Formula 1 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 according to the present invention can be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula (1). 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. At this time, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form an anode Forming an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and then depositing a material usable as a cathode on the organic material layer. 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 represented by Formula 1 may be formed into an organic 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 from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.

In one example, the first electrode is an anode, the second electrode is a cathode, 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 layer is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material. A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the 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. 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 and transports holes from the anode or the hole injection layer to the light emitting layer by using a hole transport 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 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 layer 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. Do. 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 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. The electron injection layer has an 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 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.

In addition, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

The preparation of the compound represented by Formula 1 and the organic light emitting device including the compound represented by Formula 1 will be described in detail below. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

≪ Preparation of Intermediate Compound &

Manufacturing example  1: Preparation of intermediate compound P-6

Bromo-3-fluoro-2-iodobenzene (100 g, 333.5 mmol), 5-chloro-2-methoxyphenylboronic acid -methoxyphenyl) boronic acid (62.2 g, 333.5 mmol) was dissolved in 800 ml of tetrahydrofuran (THF). To this was added a ₂ M solution of sodium carbonate (Na ₂ CO ₃ ) (500 mL) and tetrakis (triphenylphosphine) palladium (0) [Pd (PPh ₃ ) ₄ ] (7.7 g, 6.7 mmol) and refluxed for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the resulting mixture was extracted three times with water and toluene. The toluene layer was separated and dried with magnesium sulfate, and the filtrate was distilled under reduced pressure. The resulting mixture was recrystallized three times using chloroform and ethanol to obtain 53.7 g (yield: 51%; MS: M + H] < ⁺ > = 314).

Compound P-1 (50.0 g, 158.5 mmol) was dissolved in dichloromethane (600 ml) and then cooled to 0. Boron tribromide (15.8 ml, 166.4 mmol) was slowly added dropwise and stirred for 12 hours. After the reaction was completed, the reaction mixture was washed three times with water, dried with magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain 47.4 g (yield: 99% + H] < ⁺ > = 300).

Compound P-2 (40.0 g, 132.7 mmol) is dissolved in distilled dimethylformamide (DMF) (400 ml). This was cooled to 0, and sodium hydride (3.5 g, 145.9 mmol) was slowly added dropwise thereto. The mixture was stirred for 20 minutes and then at 100 for 1 hour. After the reaction was completed, the reaction mixture was cooled to room temperature and 100 ml of ethanol was slowly added thereto. The mixture was distilled under reduced pressure, and the resulting mixture was recrystallized from chloroform and ethyl acetate to obtain Compound P-3 (30.3 g, yield 81%; MS: [M + H] ⁺ = 280).

Compound P-3 (30.0 g, 106.6 mmol) was dissolved in tetrahydrofuran (300 ml), the temperature was lowered to -78, and 1.7 M tert-butyllithium (t-BuLi) (62.7 ml, 106.6 mmol) Respectively. After stirring at the same temperature for one hour, triisopropyl borate (B (OiPr) ₃ ) (28.3 ml, 213.1 mmol) was added and stirred for 3 hours while slowly raising the temperature to room temperature. To the reaction mixture was added a 2N aqueous hydrochloric acid solution (200 ml) and the mixture was stirred at room temperature for 1.5 hours. The resulting precipitate was filtered, washed with water and ethyl ether, and vacuum dried. After drying, the mixture was dispersed in ethyl ether, stirred for 2 hours, filtered and dried to give 24.4 g (yield: 93%; MS: [M + H] ⁺ = 247) of compound P-4.

The compound P-4 (20.0 g, 81.2 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (21.8 g, 81.2 mmol) were dispersed in tetrahydrofuran (250 ml) aqueous solution of potassium _{(aq.K 2 CO 3) (33.6ml} , 243.5mmol) was added and tetrakistriphenylphosphine palladium pinot [Pd (PPh _{3) 4]} was stirred under reflux for 4 hours and then put a (1.9g, 2mol%) Respectively. The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized from tetrahydrofuran and ethyl acetate, filtered, and dried to give compound P-5 (32.4 g, yield 92%; MS: [M + H] ⁺ = 434).

(30 g, 69.2 mmol) Bis (pinacolato) diborone (19.3 g, 76.1 mmol), potassium acetate (20.4 g, 207.5 mmol), tetrakis triphenyl Phosphinopalladium (0) [Pd (PPh3) 4] (1.6 g, 2 mol%) was placed in tetrahydrofuran (300 ml) and refluxed for 12 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and distilled under reduced pressure to remove the solvent. This was dissolved in chloroform and washed three times with water. The organic layer was separated and dried with magnesium sulfate. Compound P-6 (34.5 g, yield 95%; MS: [M + H] + = 526) was prepared by distillation under reduced pressure.

Manufacturing example  2: Preparation of intermediate compound P-8

Compound P-4 (40.0 g, 162.3 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6- ) Was dispersed in tetrahydrofuran (500 ml), and then tetraquistriphenylphosphinopalladium [Pd (PPh ₃ ) ₄ ] was added thereto, followed by addition of 2M aqueous potassium carbonate solution (aq. K ₂ CO ₃ ) (67.2 ml, 486.9 mmol) (3.8 g, 2 mol%) was added thereto, followed by stirring under reflux for 4 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized from tetrahydrofuran and ethyl acetate, filtered and dried to give 73.7 g (yield: 89%; MS: [M + H] ⁺ = 510) of compound P-7.

Bis (pinacolato) diborone (38.6 g, 152.13 mmol), potassium acetate (40.7 g, 414.9 mmol), tetrakis (triphenylphosphine) palladium diphenylphosphino palladium _{(0) [Pd (PPh 3} ) 4] a (3.2g, 2mol%) placed in tetrahydrofuran (600 ml) was refluxed for 12 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and distilled under reduced pressure to remove the solvent. This was dissolved in chloroform and washed three times with water. The organic layer was separated and dried with magnesium sulfate. The compound P-8 (75.7 g, yield 91%; MS: [M + H] ⁺ = 602) was prepared by distillation under reduced pressure.

Manufacturing example  3: Preparation of intermediate compound P-10

Compound P-4 (40.0 g, 162.3 mmol) and 2 - ([1,1'-biphenyl] -3-yl) -4-chloro-6-phenyl-1,3,5-triazine (55.8 g, 162.3 mmol ) Was dispersed in tetrahydrofuran (500 ml), and then tetraquistriphenylphosphinopalladium [Pd (PPh ₃ ) ₄ ] was added thereto, followed by addition of 2M aqueous potassium carbonate solution (aq. K ₂ CO ₃ ) (67.2 ml, 486.9 mmol) (3.8 g, 2 mol%) was added thereto, followed by stirring under reflux for 4 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtrated solid was recrystallized from tetrahydrofuran and ethyl acetate, filtered, and then dried to obtain Compound P-9 (69.5 g, yield 84%; MS: [M + H] ⁺ = 510).

A solution of compound P-9 (70.5 g, 138.3 mmol) bis (pinacolato) diborone (38.6 g, 152.13 mmol), potassium acetate (40.7 g, 414.9 mmol), tetrakis phenylphosphonic put pinot palladium _{(0) [Pd (PPh 3} ) 4] (3.2g, 2mol%) in tetrahydrofuran (600ml) was refluxed for 12 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and distilled under reduced pressure to remove the solvent. This was dissolved in chloroform and washed three times with water. The organic layer was separated and dried with magnesium sulfate. Compound P-10 (73.5 g, yield 88%; MS: [M + H] ⁺ = 602) was prepared by distillation under reduced pressure.

Manufacturing example  4: Preparation of intermediate compound Q-4

(2-methoxyphenyl) boronic acid was used instead of 5-chloro-2-methoxyphenyl boronic acid (62.2 g, 333.5 mmol) (81.6 g, yield 87%; MS: [M + H] < ⁺ > = 280) was obtained in the same manner as in PREPARATION EXAMPLE 1, except that 50.7 g (333.5 mmol)

(71.2 g, yield: 99%; MS: [M (M-1)] was obtained in the same manner as in PREPARATION 1, except that Compound Q-1 (75.7 g, 269.4 mmol) + H] < ⁺ > = 266).

Compound Q-3 (62.3 g, yield 95%; MS: [M (M-1)] was obtained in the same manner as in Production Example 1, except that Compound Q-2 (70.9 g, 265.3 mmol) + H] < ⁺ > = 246).

Compound Q-3 (40 g, 161.9 mmol) is dissolved in 200 ml of acetic acid. Iodine (4.16 g, 81.0 mmol), iodic acid (6.3 g, 36.0 mmol) and sulfuric acid (10 ml) were added thereto, followed by stirring at 65 for 3 hours. After the reaction is completed, the reaction mixture is cooled to room temperature and water is added thereto. The resulting solid was filtered, washed with water and then recrystallized from toluene and ethyl acetate to obtain compound Q-4 (50.1 g, yield 83%; MS: [M + H] ⁺ = 372).

Manufacturing example  5: Preparation of intermediate compound Q-5

(15.3 g, 41.1 mmol), 2'- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) spiro [indolo [3,2,1- acridine-8,9'-xanthene] (24.7 g, 45.1 mmol) was dissolved in 250 ml of tetrahydrofuran (THF). To this was added a ₂ M solution of sodium carbonate (Na ₂ CO ₃ ) (130 mL) and tetrakis (triphenylphosphine) palladium (0) [Pd (PPh ₃ ) ₄ ] (1.4 g, 3 mol%) and refluxed for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the resulting mixture was extracted three times with water and toluene. The toluene layer was separated and dried with magnesium sulfate, and the filtrate was distilled under reduced pressure. The resulting mixture was recrystallized from chloroform and ethyl acetate to obtain Compound Q-5 (19.6 g, yield: 72%; MS: [M + H] < ⁺ > = 666).

Manufacturing example  6: Preparation of intermediate compound S-4

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (17.6 g, 162.3 mmol), compound R-3 was used in place of compound P- 3 (71.0 g, 162.3 mmol) was obtained in the same manner as in the preparation of the compound P-5 of Production Example 1, except that 4- (4-chloro-phenyl) g, yield: 89%; MS: [M + H] < ⁺ > = 492).

Compound S-3 (71 g, 144.6 mmol) is dissolved in 500 ml of DMF. NBS (29.60 g, 166.3 mmol) was added thereto, and the mixture was stirred at 65 for 3 hours. After the reaction was completed, the mixture was cooled to room temperature and water was added thereto. The resulting solid was filtered, washed with water, and then recrystallized from toluene and ethyl acetate to obtain Compound S-4 (66.1 g, yield 80%; MS: [M + H] ⁺ = 570).

Manufacturing example  7: Preparation of intermediate compound S-6

Instead of compound P-4, compound R-3 was used instead of 2-chloro-4,6-diphenylpyrimidine (43.3 g, 162.3 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5- (57.9 g, yield 86%; MS: [M + H] < ⁺ > = 415) was prepared in the same manner as in the preparation of Compound P-5 of Preparation Example 1,

Compound S-5 (57.9 g, 161.9 mmol) is dissolved in 500 ml of DMF. NBS (28.63 g, 160.83 mmol) was added thereto, and the mixture was stirred at 65 for 3 hours. After the reaction is completed, the reaction mixture is cooled to room temperature and water is added thereto. The resulting solid was filtered, washed with water and then recrystallized with toluene and ethyl acetate to obtain 57.4 g (yield: 83%; MS: [M + H] ⁺ = 493) of compound S-6.

< Example >

Example  1: Preparation of compound 1

The compound P-6 (20.0 g, 38.1 mmol) and 2-bromospiro [indolo [3,2,1-de] acridine-2-bromospiro [ 1-de] acridine-8,9'-xanthene] (17.32 g, 34.64 mmol) was dispersed in tetrahydrofuran (280 ml), and a 2M aqueous potassium carbonate solution (aq. K ₂ CO ₃ ) was added to the mmol), insert tetrakis triphenyl phosphino palladium _{[Pd (PPh 3) 4]} (1.2g, 3mol%) was refluxed with stirring for 6 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethyl acetate (300 ml), filtered, and dried to give Compound 1 (21.6 g, yield 76%; MS: [M + H] ⁺ = 819).

Example  2: Preparation of compound 2

The compound P-6 (14.3 g, 27.2 mmol) and 10-bromopyro [indolo [3,2,1-de] acridine-10-bromospiro [ 1-de] acridine-8,9'-xanthene] (12.4 g, 24.7 mmol) was dispersed in tetrahydrofuran (250 ml), and a 2M aqueous potassium carbonate solution (aq. K ₂ CO ₃ ) was added to the mmol), insert tetrakis triphenyl phosphino palladium _{[Pd (PPh 3) 4]} (0.9g, 3mol%) was refluxed with stirring for 4 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethyl acetate (260 ml), filtered, and dried to give Compound 2 (16.2 g, yield 80%; MS: [M + H] ⁺ = 819).

Example  3: Preparation of compound 3

(12.4 g, yield 65%; MS: [M + H] ⁺ = 894) was prepared in the same manner as in Example 1 except that Compound P-8 (14.1 g, 23.5 mmol) Respectively.

Example  4: Preparation of compound 4

(20.3 g, yield 7%; MS: [M + H] ⁺ = 702) was prepared in the same manner as in Example 2 except that the compound P-10 (22.9 g, 38.1 mmol) Respectively.

Example  5: Preparation of compound 5

The compound P-6 was replaced with 2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- 14.1 g, 32.4 mmol), 2-bromospiro [indolo [3,2,1-de] acridine-8,9'-xanthine (21.5 g, yield 81%; MS: [M + H] &lt; ⁺ &gt;] was obtained in the same manner as in Example 1, except that Compound Q-5 (19.6 g, 29.5 mmol) = 895).

Example  6: Preparation of Compound 6

Compound S-4 (12.4 g, 21.7 mmol), 2-bromospiro [indolo [3,2,1-de] acridine-8,9'-indanol Indolo [3,2,1-de] acridine-8,9'-xanthen] -2'-ylboronic acid (11.1 g, (M + H] ⁺ = 911) was prepared in the same manner as in Example 2, except that the compound (6) (13.3 g, yield 67%

Example  7: Preparation of Compound 7

Compound S-6 (15.3 g, 31.1 mmol), 2-bromospiro [indolo [3,2,1-de] acridine-8,9'-indanol [3,2,1-de] acridine-8,9'-xanthene] instead of spiro [indolo [3,2,1-de] acridine-8,9'-xantin-4'- Except that spiro [indolo [3,2,1-de] acridine-8,9'-xanthen] -4'-ylboronic acid (15.9 g, 34.2 mmol) (16.8 g, yield 65%; MS: [M + H] &lt; ⁺ &gt; = 834).

< Experimental Example  1>

compare Experimental Example  1-1

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.

On this ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 150 Å to form a hole injection layer.

[LINE]

The following compound 4,4 '- (9-phenyl-9H-carbazole-3,6-diyl) bis (N, N-diphenylaniline) [HT 1] (1150 Å), which is a hole transporting material, To form a hole transporting layer.

[HT 1]

Subsequently, the following compound [EB 1] was vacuum deposited on the hole transport layer to a thickness of 100 Å to form an electron blocking layer.

[EB 1]

Subsequently, BH and BD were vapor-deposited at a weight ratio of 25: 1 on the electron blocking layer to a thickness of 200 ANGSTROM to form a light emitting layer.

The compound [HB 1] was vacuum deposited on the hole transport layer to a thickness of 50 Å on the light emitting layer to form a hole blocking layer.

Subsequently, compound ET 1 and the compound LiQ (Lithium Quinolate) were vacuum deposited on the hole blocking layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 310 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.

Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, the degree of vacuum upon deposition ⅹ10 2 ^-7 To 5 x 10 &lt; ^-6 &gt; torr, thereby fabricating an organic light emitting device.

Experimental Example  1-1 to 1-7

An organic light emitting device was fabricated in the same manner as in Comparative Experiment Example 1, except that Compound 1 to Compound 7 were used instead of ET 1 in Comparative Experimental Example 1, as shown in Table 1.

compare Experimental Example  1-2 and 1-3

An organic light emitting device was fabricated in the same manner as in Comparative Experimental Example 1, except that ET 2 and ET 3 were used in place of ET 1 in Comparative Experimental Example 1, as shown in Table 1.

[ET 2]

[ET 3]

The voltage, efficiency, color coordinate and lifetime were measured when current was applied to the organic light-emitting device manufactured in Experimental Examples 1-1 to 1-7 and Comparative Experimental Examples 1-1 to 1-3, 1]. T95 means the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.

division compound
(Electron transport layer) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA /
cm ² ) Color coordinates
(x, y) T95 (hr) Comparative Experimental Example 1-1 ET 1 5.12 5.23 (0.140, 0.047) 225 Experimental Example 1-1 Compound 1 4.21 5.94 (0.140, 0.044) 280 Experimental Example 1-2 Compound 2 4.35 5.865 (0.141, 0.046) 275 Experimental Example 1-3 Compound 3 4.64 5.52 (0.141, 0.045) 260 Experimental Examples 1-4 Compound 4 4.36 5.88 (0.142, 0.043) 275 Experimental Examples 1-5 Compound 5 4.57 5.67 (0.141, 0.045) 265 Experimental Example 1-6 Compound 6 4.38 5.85 (0.140, 0.044) 275 Experimental Example 1-7 Compound 7 4.24 5.95 (0.142, 0.043) 270 Comparative Experimental Example 1-2 ET 2 4.77 5.06 (0.140, 0.043) 235 Comparative Experimental Example 1-3 ET 3 4.63 5.01 (0.141, 0.046) 245

As shown in Table 1, the organic light emitting device manufactured using the compound of the present invention as an electron transport layer shows excellent characteristics in terms of efficiency, driving voltage and / or stability of the organic light emitting device.

The compounds of the present invention exhibit characteristics of low voltage, high efficiency, and long life, compared with organic light emitting devices manufactured using the compounds of Comparative Experimental Examples 1-2 and 1-3 in which two substituents are connected to one side thereof as an electron transport layer.

As shown in Table 1, it was confirmed that the compounds according to the present invention are excellent in electron transporting ability and applicable to organic light emitting devices.

< Experimental Example  2>

compare Experimental Example  2-1

In Comparative Experimental Example 1-1, instead of using BH and BD as the light emitting layer, the following compounds GH 1 and GD were vacuum deposited at a weight ratio of 20: 1 to a thickness of 350 Å to form a light emitting layer.

&Lt; Experimental Examples 2-1 to 2-7 >

An organic light emitting device was fabricated in the same manner as in Comparative Experiment Example 2 except that the compounds 1 to 7 were respectively used as shown in Table 2 instead of GH in the Comparative Experimental Example 2-1.

compare Experimental Example  2-2 to 2-4

An organic light emitting device was fabricated in the same manner as in Comparative Experiment Example 2, except that the following GH 2 to GH 4 compounds were used instead of GH 1 in Comparative Experiment Example 2 as shown in Table 1 below.

[GH 2]

[GH 3]

[GH 4]

The voltage, efficiency, color coordinate and lifetime were measured when current was applied to the organic light-emitting device manufactured in Experimental Examples 2-1 to 2-7 and Comparative Experimental Examples 2-1 to 2-4, 2]. T95 means the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.

division compound
(Green luminescent layer
Host) Voltage
(V @ 10mA
/ cm ² ) efficiency
(cd / A @ 10mA
/ cm ² ) Color coordinates
(x, y)
T95 (hr) Comparative Experimental Example 2-1 GH 1 4.12 105.26 (0.253, 0.705) 235 Experimental Example 2-1 Compound 1 3.84 121.91 (0.255, 0.702) 330 EXPERIMENTAL EXAMPLE 2-2 Compound 2 3.96 119.65 (0.256, 0.700) 330 Experimental Example 2-3 Compound 3 3.98 119.81 (0.254, 0.701) 325 Experimental Example 2-4 Compound 4 3.97 117.75 (0.255, 0.689) 335 Experimental Example 2-5 Compound 5 3.91 116.55 (0.257, 0.695) 325 Experimental Examples 2-6 Compound 6 3.95 118.46 (0.255, 0.699) 325 Experimental Example 2-7 Compound 7 3.84 121.91 (0.255, 0.695) 340 Comparative Experimental Example 2-2 GH 2 4.12 111.34 (0.253, 0.705) 260 Comparative Experimental Example 2-3 GH 3 4.72 103.48 (0.253, 0.705) 120 Comparative Experimental Example 2-4 GH 4 4.53 106.75 (0.253, 0.705) 165

As shown in Table 2, the organic light emitting device manufactured using the compound of the present invention as a green light emitting layer exhibits excellent characteristics in terms of efficiency, driving voltage and / or stability of the organic light emitting device.

It was confirmed that the lifetime characteristics were remarkably lowered when a compound containing only a carbazole group or a triazine group was used outside the structure of the present invention.

Although the preferred embodiments of the present invention (electron transport layer, green light emitting layer) have been described above, the present invention is not limited thereto, but can be variously modified and embodied within the scope of the claims and the detailed description of the invention This also falls within the scope of the invention.

1: substrate 2: anode
3: light emitting layer 4: cathode
5: Hole injection layer 6: Hole transport layer
7: light emitting layer 8: electron transporting layer

Claims (11)

A compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
X ₁ is O, S or NR ₁ ,
R ₁ is a substituted or unsubstituted unsubstituted C _1-60 alkyl,
X ₂ , X ₃ and X ₄ are each independently N or CR ', provided that at least one of them is N,
R 'is hydrogen or substituted or unsubstituted C _1-60 alkyl,
Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-60 aryl or substituted or unsubstituted C _5-60 heteroaryl containing at least one of N, O and S.
The method according to claim 1,
Wherein the compound represented by the formula (1) is any one selected from the compounds represented by the following formulas (1-1) to (1-4):
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In the above Formulas 1-1 to 1-4,
X ₁ , X ₂ , X ₃ , X ₄ , Ar ₁ and Ar ₂ are as defined in claim 1.
3. The method of claim 2,
Wherein the compound represented by Formula 1-1 is any one of compounds represented by the following Formulas 1-1a to 1-1c:
[Formula 1-1a]

[Formula 1-1b]

[Formula 1-1c]

In the above formulas 1-1a to 1-1c,
X ₁ , X ₂ , X ₃ , X ₄ , Ar ₁ and Ar ₂ are as defined in claim 1.
3. The method of claim 2,
Wherein the compound represented by Formula 1-2 is a compound represented by Formula 1-2a or 1-2b:
[Formula 1-2a]

[Formula 1-2b]

In the formula 1-2a or 1-2b,
X ₁ , X ₂ , X ₃ , X ₄ , Ar ₁ and Ar ₂ are as defined above.
3. The method of claim 2,
Wherein the compound represented by Formula 1-3 is any one of compounds represented by Formulas 1-3a to 1-3c:
[Formula 1-3a]

[Formula 1-3b]

[Chemical Formula 1-3c]

In the above formulas 1-3a to 1-3c,
X ₁ , X ₂ , X ₃ , X ₄ , Ar ₁ and Ar ₂ are as defined in claim 1.
3. The method of claim 2,
Wherein the formula 1-4 is a compound represented by the following formula 1-4a or 1-4b:
[Chemical Formula 1-4a]

[Chemical Formula (1-4b)

In the formula 1-4a or 1-4b,
X ₁ , X ₂ , X ₃ , X ₄ , Ar ₁ and Ar ₂ are as defined in claim 1.
The method according to claim 1,
Ar ₁ and Ar ₂ are each independently any one selected from the group consisting of:

.
The method according to claim 1,
Ar ₁ and Ar ₂ are each independently

or

/ RTI &gt;
The method according to claim 1,
The compound represented by the formula (1) is any one selected from the group consisting of:

.
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 at least one of the organic compound layers includes a compound according to any one of claims 1 to 9 The organic light-emitting device.
11. The method of claim 10,
The organic compound layer containing the compound may include an electron injection layer; An electron transport layer; Or an electron injection and electron transporting layer simultaneously.

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