KR101964437B1 - Novel hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel heterocyclic compound and an organic light emitting device using the same.

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. 10-2000-0051826

The present invention relates to a novel heterocyclic 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,

이고, 다른 하나는 -L-Ar₁이고,One of A and B is

And the other is -L-Ar ₁ ,

R ₁ and R ₂ are each independently hydrogen; heavy hydrogen; halogen; Nitrile; Nitro; Amino; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl comprising at least one of O, N, Si and S,

X ₁ is O, or S,

X ₂ is O, S, or NR ₃ ,

Wherein R ₃ is substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl comprising at least one of O, N, Si and S,

L is a bond; Substituted or unsubstituted C _6-60 arylene; Or C _2-60 heteroarylene containing at least one of substituted or unsubstituted O, N, Si and S,

Ar ₁ is any one selected from the group consisting of:

In the above,

Y ₁ to Y ₃ are each independently CH or N, with the proviso that at least one of Y ₁ to Y ₃ is N,

Y ₄ to Y ₇ are each independently CH or N, with the proviso that at least one of Y ₄ to Y ₇ is N,

Y ₈ and Y ₉ are each independently CH or N, with the proviso that at least one of Y ₈ and Y ₉ is N,

Y ₁₀ and Y ₁₁ are each independently CH or N, with the proviso that at least one of Y ₁₀ and Y ₁₁ is N,

Y ₁₂ and Y ₁₃ are each independently CH or N, with the proviso that at least one of Y ₁₂ and Y ₁₃ is N,

Y ₁₄ and Y ₁₅ are each independently CH or N, with the proviso that at least one of Y ₁₄ and Y ₁₅ is N,

Ar ₂ to Ar ₇ each independently represent 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 present invention also provides a plasma display panel 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 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 above formula (1).

, 또는

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

, or

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.

Formula 1 is represented by Formulas 1-1 and 1-2 according to A and B, respectively.

[Formula 1-1]

[Formula 1-2]

Preferably, R ₁ and R ₂ are hydrogen.

Preferably, R < ₃ > is phenyl.

L is a bond, phenylene, or naphthalenediyl.

Preferably, Ar ₂ and Ar ₃ are each independently phenyl, biphenyl, or pyridinyl.

Preferably, Ar ₄ to Ar ₇ are each independently phenyl, biphenyl, naphthyl, or carbazolyl.

Preferably, Ar < ₁ > is any one selected from the group consisting of:

Representative examples of the compound represented by the above formula (1) are as follows:

인 경우, 일례로 하기 반응식 1과 같은 제조 방법으로 제조할 수 있다. On the other hand, in the compounds represented by the above formula

, It can be prepared, for example, according to the production method shown in Reaction Scheme 1 below.

[Reaction Scheme 1]

In the above Reaction Scheme 1, the definitions other than X 'are as described above, and X' is halogen, more preferably bromo or chloro.

인 경우에도 아민 치환 반응을 응용하여 제조할 수 있다. 상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다. The reaction is preferably carried out in the presence of a palladium catalyst and a base as an amine substitution reaction, and the reactor for the amine substitution reaction can be modified as known in the art. In the compounds represented by the general formula (1), A is

Can also be prepared by applying an amine substitution reaction. 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).

Further, the electron transporting layer, the electron injecting layer, or the layer which simultaneously transports electrons and injects electrons includes the compound represented by the above formula (1).

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 comprising the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

[ Manufacturing example ]

Manufacturing example  1: Preparation of Compound A

1) Preparation of compound A-a

In a three-necked flask, 2-bromo-modify-benzo [b, d] was dissolved in THF (30.0 g, 121.4 mmol), (2-nitrophenyl) boronic acid (22.3 g, 133.6 mmol) to THF (450 mL), K ₂ CO ₃ (67.1 g, 485.71 mmol) was dissolved in water (225 mL). Here, insert the _{Pd (PPh 3) 4 (5.6} g, 4.9 mmol), and stirred for 8 hours under an argon atmosphere and reflux conditions. After the reaction was completed, the reaction solution was cooled to room temperature, transferred to a separatory funnel, and extracted with ethyl acetate. The extract was dried with MgSO ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography to obtain Compound Aa (30.9 g, yield 88%, MS [M + H] ⁺ = 289).

2) Preparation of compound A-b

Compound Aa (30.0 g, 103.7 mmol), NBS (19.4, 108.9 mmol) and DMF (600 mL) were added to a two-necked flask, and the mixture was stirred at room temperature for 5 hours under argon atmosphere. After completion of the reaction, the reaction solution was transferred to a separatory funnel, and water (200 mL) was added thereto, followed by extraction with ethyl acetate. The sample was purified by silica gel column chromatography to give compound Ab (32.5 g, yield 48%, MS [M + H] ⁺ = 368).

3) Preparation of Compound A

Compound Ab (30.0 g, 81.5 mmol), triphenylphosphine (16.9 g, 122.2 mmol) and o-dichlorobenzene (300 mL) were placed in a two-necked flask and stirred under reflux for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, distilled under reduced pressure to remove the solvent, and extracted with water and CH ₂ Cl ₂ . The extract was dried with MgSO ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography to obtain Compound A (18.4 g, yield 64%, MS [M + H] ⁺ = 336).

Manufacturing example  2: Preparation of compound B

Compound B was prepared in the same manner as Compound A, except that 2-bromodibenzo [b, d] thiophene was used instead of 2-bromodibenzo [b, d] furan (18.4 g, 64%, MS [M + H] < ⁺ > = 352).

[ Example ]

Example  1: Preparation of compound 1

1) Preparation of compound 1-a

(13.6 g, 53.5 mmol), Pd (dba) ₂ (0.5 g, 0.9 mmol), tricyclohexylphosphine (15.0 g, 0.5 g, 1.8 mmol), KOAc (8.8 g, 89.2 mmol) and 1,4-dioxane (225 mL) were added and the mixture was stirred under an argon atmosphere and refluxing condition for 12 hours. After the reaction was completed, the reaction solution was transferred to a separatory funnel, and water (200 mL) was added thereto, followed by extraction with ethyl acetate. The extract was dried with MgSO ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography to obtain Compound 1-a (14.2 g, yield 83%, MS [M + H] ⁺ = 383).

2) Preparation of compound 1-b

To a three-necked flask, Compound 1-a (14.0 g, 36.5 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (10.8 g, 40.2 mmol) And K ₂ CO ₃ (20.2 g, 146.1 mmol) was dissolved in water (105 mL). Here, insert the _{Pd (PPh 3) 4 (1.7} g, 1.5 mmol), and stirred for 8 hours under an argon atmosphere and reflux conditions. After the reaction was completed, the reaction solution was cooled to room temperature, transferred to a separatory funnel, and extracted with ethyl acetate. The extract was dried with MgSO ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography to obtain Compound 1-b (13.9 g, yield 78%, MS [M + H] ⁺ = 489).

3) Preparation of compound 1

(7.2 g, 29.3 mmol) was dissolved in toluene (325 mL) and sodium tert-butoxide (7.7 g, 29.6 mmol) was added to a three-necked flask. g, 79.8 mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.5 mmol) were added thereto and stirred for 6 hours under argon atmosphere and refluxing conditions. After the reaction was completed, the reaction mixture was cooled to room temperature, and water (200 mL) was added thereto. The reaction mixture was transferred to a separatory funnel and extracted. The extract was dried with MgSO ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography, and Compound 1 was obtained through sublimation purification (7.3 g, yield 42%, MS [M ⁺ = 655).

Example  2: Preparation of compound 2

Compound 2 was prepared (6.1 g, yield 35%) in the same manner as in the preparation of compound 1, except that 4-bromodibenzo [b, d] furan was used instead of 2-bromodibenzo [b, , MS [M + H] < ⁺ > = 655).

Example  3: Preparation of compound 3

Compound 3 was prepared in the same manner as in the preparation of Compound 1 except that 2-bromodibenzo [b, d] thiophene was used in place of 2-bromodibenzo [b, d] furan (6.6 g, yield 37 %, MS [M + H] < ⁺ > = 671).

Example  4: Preparation of compound 4

Compound 4 was prepared in the same manner as in the preparation of Compound 1 except that 4-bromodibenzo [b, d] thiophene was used instead of 2-bromodibenzo [b, d] furan (7.1 g, 40%, MS [M + H] < ⁺ > = 671).

Example  5: Preparation of compound 5

Compound 5 was prepared in the same manner as in the preparation of Compound 1 except that 3-bromo-9-phenyl-9H-carbazole was used instead of 2-bromodibenzo [b, d] furan (6.0 g, yield 31%, MS [M + H] < ⁺ > = 730).

Example  6: Preparation of Compound 6

1) Preparation of compound 6-a

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, 2 - ([ (13.8 g, yield 78%, MS [M + H] < ⁺ > = 565) was prepared in the same manner as in the preparation of compound 1-b, except that 5-triazine was used.

2) Preparation of Compound 6

Except that the compound 6-a was used in place of the compound 1-b and 3-bromo-9-phenyl-9H-carbazole was used in place of 2-bromodibenzo [b, d] (6.0 g, yield 35%, MS [M + H] < ⁺ > = 806).

Example  7: Preparation of Compound 7

Except that the compound 6-a was used in place of the compound 1-b and 2-bromodibenzo [b, d] thiophene was used in place of 2-bromodibenzo [b, d] Compound 7 was prepared in the same manner (7.6 g, yield 38%, MS [M + H] ⁺ = 947).

Example  8: Preparation of compound 8

Compound 8 was prepared (6.5 g, yield 42%, MS [M + H] ⁺ = 731) in the same manner as in the preparation of Compound 1, except that Compound 6-a was used instead of Compound 1-b.

Example  9: Preparation of compound 9

1) Preparation of compound 9-a

(15.0 g, 42.6 mmol), bis (pinacolato) diboron (13.0 g, 51.1 mmol), Pd (dba) ₂ (0.5 g, 0.9 mmol), tricyclohexylphosphine 0.5 g, 1.7 mmol), KOAc (8.4 g, 85.2 mmol), and 1,4-dioxane (225 mL) were added and the mixture was stirred under an argon atmosphere and refluxing condition for 12 hours. After the reaction was completed, the reaction solution was transferred to a separatory funnel, and water (200 mL) was added thereto, followed by extraction with ethyl acetate. The extract was dried with MgSO ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography to obtain Compound 9-a (14.8 g, yield 87%, MS [M + H] ⁺ = 399).

2) Preparation of compound 9-b

(14.3 g, 35.1 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (13.3 g, 38.6 mmol) were dissolved in THF (210 mL), and K ₂ CO ₃ (19.4 g, 140.2 mmol) was dissolved in water (105 mL). Here, insert the _{Pd (PPh 3) 4 (1.6} g, 1.4 mmol), and stirred for 8 hours under an argon atmosphere and reflux conditions. After the reaction was completed, the reaction solution was cooled to room temperature, transferred to a separatory funnel, and extracted with ethyl acetate. The extract was dried with MgSO ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography to obtain Compound 9-b (14.5 g, yield 71%, MS [M + H] ⁺ = 581).

3) Preparation of Compound 9

B, d] furan (6.6 g, 26.5 mmol) was dissolved in toluene (350 mL) and sodium tert-butoxide (7.0 g, g, 72.3 mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.2 g, 0.5 mmol) were added thereto and stirred for 6 hours under argon atmosphere and refluxing conditions. After the reaction was completed, the reaction mixture was cooled to room temperature, and water (200 mL) was added thereto. The reaction mixture was transferred to a separatory funnel and extracted. The extract was dried with MgSO ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography, and the compound 9 was obtained by sublimation purification (6.3 g, yield 35%, MS [M ⁺ = 747).

Example  10: Preparation of compound 10

1) Preparation of compound 10-a

Preparation of 9-b was carried out except that 4-chloro-2,6-diphenylpyrimidine was used instead of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (13.8 g, yield 78%, MS [M + H] < ⁺ > = 504).

2) Preparation of Compound 10

Except that the compound 10-a was used in place of the compound 9-b and 4-bromodibenzo [b, d] thiophene was used in place of 2-bromodibenzo [b, d] Compound 10 was prepared in the same manner (6.2 g, yield 38%, MS [M + H] ⁺ = 686).

Example  11: Preparation of compound 11

1) Preparation of compound 11-a

In a three-necked flask, Compound 1-a (14.0 g, 36.5 mmol) and 2-bromodibenzo [b, d] furan (9.9 g, 40.2 mmol) were dissolved in THF (210 mL) and K ₂ CO ₃ , 146.1 mmol) was dissolved in water (105 mL). Here, insert the _{Pd (PPh 3) 4 (1.7} g, 1.5 mmol), and stirred for 8 hours under an argon atmosphere and reflux conditions. After the reaction was completed, the reaction solution was cooled to room temperature, transferred to a separatory funnel, and extracted with ethyl acetate. The extract was dried with MgSO ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography to obtain Compound 11-a (11.0 g, yield 71%, MS [M + H] ⁺ = 423).

2) Preparation of compound 11

Compound 11-a (11.0 g, 26.0 mmol) and 2-chloro-4-phenylquinazoline (6.9 g, 28.6 mmol) were dissolved in toluene (300 mL) and sodium tert- 77.9 mmol), and bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.5 mmol) were added thereto and stirred for 6 hours under argon atmosphere and refluxing conditions. After the reaction was completed, the reaction mixture was cooled to room temperature, and water (200 mL) was added thereto. The reaction mixture was transferred to a separatory funnel and extracted. (5.1 g, yield 31%, MS [M + H] < ⁺ >] was obtained by sublimation purification, after which the extract was dried with MgSO ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography, = 628).

Example  12: Preparation of compound 12

Compound 12 was prepared in the same manner as Compound 11, except that 2-chloro-4- (naphthalen-2-yl) quinazoline was used in place of 2-chloro-4-phenylquinazoline 33%, MS [M + H] < ⁺ > = 678).

Example  13: Preparation of compound 13

1) Preparation of compound 13-a

Dibenzo [b, d] furan-4-ylboronic acid (10.4 g, 49.1 mmol) was dissolved in THF (225 mL) and K ₂ CO ₃ (24.7 g, 178.5 mmol) was dissolved in water (113 mL). Here, insert the _{Pd (PPh 3) 4 (2.1} g, 1.8 mmol), and stirred for 8 hours under an argon atmosphere and reflux conditions. After the reaction was completed, the reaction solution was cooled to room temperature, transferred to a separatory funnel, and extracted with ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography to obtain 13-a (13.6 g, yield 72%, MS [M + H] ⁺ = 423).

2) Preparation of compound 13

3-yl] pyrimidine (8.8 g, 31.2 mmol) was dissolved in toluene (300 mL), and a solution of the compound 13-a (0.2 g, 85.0 mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.6 mmol) were placed in a flask under argon atmosphere and refluxing for 6 hours Respectively. After the reaction was completed, the reaction mixture was cooled to room temperature, and water (200 mL) was added thereto. The reaction mixture was transferred to a separatory funnel and extracted. The extract was dried with MgSO ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography, and then Compound 13 was obtained through sublimation purification (7.9 g, yield 42%, MS [M ⁺ = 668).

Example  14: Preparation of compound 14

Except that 2-chloro-4-phenylbenzo [4,5] thieno [3,2-d] pyrimidine was used instead of 2-chloro-4-phenylbenzofuro [3,2- d] pyrimidine Compound 14 was prepared (7.8 g, yield 40%, MS [M + H] ⁺ = 684) in the same manner as compound 13.

Example  15: Preparation of compound 15

1) Preparation of compound 15-a

A was prepared in the same manner as in the production of compound 13-a, except that dibenzo [b, d] thiophen-4-ylboronic acid was used instead of dibenzo [b, (15.3 g, yield 78%, MS [M + H] < ⁺ > = 440).

2) Preparation of compound 15

Except that the compound 15-a was used in place of the compound 13-a and 4-chloro-2-phenylquinazoline was used in place of 2-chloro-4-phenylbenzofuro [3,2- d] pyrimidine Compound 13 was prepared (7.3 g, yield 33%, MS [M + H] ⁺ = 644).

Example  16: Preparation of compound 16

1) Preparation of compound 16-a

Compound 16-a was prepared (15.9 g, yield 85%, MS [M + H] ⁺ = 440) in the same manner as in the preparation of compound 13-a, except that compound B was used instead of compound A.

2) Preparation of Compound 16

Compound 16-a was used in the place of Compound 13-a and 2- (4-chlorophenyl) -4,6-diphenyl-1-yloxybenzo [ Compound 16 was prepared (8.6 g, yield 42%, MS [M + H] ⁺ = 747) in the same manner as in the preparation of Compound 13, except that 3,5-triazine was used.

Example  17: Preparation of compound 17

The compound 16-a was used in the place of the compound 13-a, and instead of 2- (4-chloronaphthalen-1-yl) -4,6-dimethylbenzo [b] Compound 9 was prepared (9.4 g, yield 43%, MS [M + H] ⁺ = 797) in the same manner as in the preparation of Compound 13, except that diphenyl-1,3,5- .

[ Experimental Example ]

Experimental Example  1-1

A glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1,400 Å was immersed 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 which was secondly 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.

A mixture of 95% by weight of the following HT-A compound and 5% by weight of the following P-DOPANT compound was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 100 Å. Then, only HT- To form a transport layer. The HT-B compound was thermally vacuum deposited to a thickness of 450 Å to form an electron blocking layer. Then, Compound 1, the following GH-P compound, and the following GD compound were vapor deposited in a thickness of 400 Å at a weight ratio of 45:45:10 to form a light emitting layer. The following ET-A compound was vacuum-deposited to a thickness of 50 Å to form a hole blocking layer. Then, the following ET-B compound and the following Liq compound were thermally vacuum-deposited to a thickness of 250 Å at a weight ratio of 2: 1 to form an electron transport layer. LiF and magnesium were then deposited thereon at a weight ratio of 30: Vacuum deposition was performed to form an electron injection layer. Then, magnesium and silver were vapor-deposited at a weight ratio of 1: 4 to a thickness of 160 ANGSTROM to form a cathode, thereby preparing an organic light emitting device.

Experimental Example  1-2 to 1-10

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the compound described in Table 1 was used instead of Compound 1.

Comparative Experimental Example  1-1 to 1-5

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the compound described in Table 1 was used instead of Compound 1. In Table 1, the compounds of GH-A, GH-B, GH-C, GH-D and GH-E are as follows.

The voltage, efficiency, and lifetime (T ₉₅ ) were measured by applying a current to the organic light emitting device manufactured in Experimental Examples and Comparative Experimental Examples, and the results are shown in Table 1 below. At this time, the voltage and efficiency were measured by applying a current density of 10 mA / cm ² , and T ₉₅ means the time until the initial luminance decreased to 95% at a current density of 20 mA / cm ² .

compound Voltage (V)
(@ 10 mA / cm ² ) Efficiency (cd / A)
(@ 10 mA / cm ² ) Life (T ₉₅ , hr)
(@ 20 mA / cm ² ) Experimental Example 1-1 Compound 1 4.26 59.55 120 Experimental Example 1-2 Compound 2 4.13 54.15 130 Experimental Example 1-3 Compound 3 4.28 56.43 110 Experimental Examples 1-4 Compound 4 4.18 55.25 140 Experimental Examples 1-5 Compound 5 4.26 57.39 130 Experimental Example 1-6 Compound 6 4.21 53.73 120 Experimental Example 1-7 Compound 7 4.34 57.39 130 Experimental Examples 1-8 Compound 8 4.48 53.73 120 Experimental Examples 1-9 Compound 9 4.26 57.39 130 Experimental Example 1-10 Compound 10 4.30 53.73 120 Comparative Experimental Example 1-1 GH-A 4.65 48.11 80 Comparative Experimental Example 1-2 GH-B 4.81 38.19 70 Comparative Experimental Example 1-3 GH-C 4.91 41.15 30 Comparative Experimental Examples 1-4 GH-D 4.71 40.15 30 Comparative Experimental Examples 1-5 GH-E 5.26 20.81 15

Experimental Example  2-1

A glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1,400 Å was immersed 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 which was secondly 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 following HI-A compound and the following HAT compound were sequentially deposited by thermal vacuum deposition to a thickness of 800 ANGSTROM and 50 ANGSTROM, respectively, on the thus-prepared ITO transparent electrode to form a hole injection layer. Then, the following HT-C compound was vacuum-deposited to a thickness of 800 Å to form a hole transport layer, and then the following EB-A compound was thermally vacuum deposited to a thickness of 600 Å to form an electron blocking layer. Compound 11 and RD compound prepared above were vacuum deposited at a weight ratio of 98: 2 to a thickness of 400 Å to form a light emitting layer. Subsequently, the following ET-C compound and the following Liq compound were thermally vacuum-deposited at a weight ratio of 1: 1 to a thickness of 360 Å as an electron transporting and injecting layer, and then the following Liq compound was vacuum-deposited to a thickness of 5 Å to form an electron transport layer and an electron An injection layer was sequentially formed. Magnesium and silver were sequentially deposited on the electron injection layer at a weight ratio of 10: 1 to a thickness of 220 ANGSTROM and aluminum to a thickness of 1,000 ANGSTROM to form a cathode. Thus, an organic light emitting device was prepared.

Experimental Example  2-2 to 2-7

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1 except that the compound described in Table 2 was used instead of Compound 11.

Comparative Experimental Example  2-1 to 2-4

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1 except that the compound described in Table 2 was used instead of Compound 11. In Table 2, the compounds of RH-A, RH-B, RH-C and RH-D are as follows.

The voltage, the efficiency, and the lifetime (T ₉₅ ) were measured by applying a current to the organic light emitting device manufactured in Experimental Examples and Comparative Experimental Examples, and the results are shown in Table 2 below. At this time, the voltage and efficiency were measured by applying a current density of 10 mA / cm ² , and T ₉₅ means the time until the initial luminance decreased to 95% at a current density of 20 mA / cm ² .

compound Voltage (V)
(@ 10 mA / cm ² ) Efficiency (cd / A)
(@ 10 mA / cm ² ) Life (T ₉₅ , hr)
(@ 20 mA / cm ² ) Experimental Example 2-1 Compound 11 4.56 24.51 220 EXPERIMENTAL EXAMPLE 2-2 Compound 12 4.45 24.33 230 Experimental Example 2-3 Compound 13 4.51 23.42 210 Experimental Example 2-4 Compound 14 4.65 24.16 240 Experimental Example 2-5 Compound 15 4.66 22.76 230 Experimental Examples 2-6 Compound 16 4.51 24.73 220 Experimental Example 2-7 Compound 17 4.76 24.91 230 Comparative Experimental Example 2-1 RH-A 5.23 21.93 130 Comparative Experimental Example 2-2 RH-B 5.12 17.51 70 Comparative Experimental Example 2-3 RH-C 6.15 16.41 30 Comparative Experimental Example 2-4 RH-D 4.80 19.87 80

In the compound represented by the formula (1) according to the present invention, the portions having the n-type property and the p-type property are divided and located in A and B, respectively. The positions where A and B are substituted face each other in space, and charge is transferred from the portion having the n-type property internally to the portion having the p-type property to form the Intra-ChargeTransfer state. When a material having such a property is used as a host of a light emitting layer of an organic light emitting device, both a hole transfer and an electron transfer are remarkably effective, thereby exhibiting low voltage, high efficiency, and long life characteristics.

Specifically, as can be seen from the structure of the compound 1 prepared in Example 1, when a portion having an n-type property is present at the position of A and a portion having a p-type property is present at the position of B, . On the other hand, when the positions of A and B are changed, the red light emitting layer host has appropriate characteristics as a host of the red light emitting layer. In comparison with the materials of the comparative example in which the structure, It can be confirmed that it shows excellent characteristics.

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 (9)

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

In Formula 1,
One of A and B is

And the other is -L-Ar ₁ ,
R ₁ and R ₂ are each independently hydrogen; heavy hydrogen; halogen; Nitrile; Nitro; Amino; C _1-60 alkyl; C _3-60 cycloalkyl; C _2-60 alkenyl; C _6-60 aryl; Or C _2-60 heteroaryl containing one or more of O, N, Si and S,
X ₁ is O, or S,
X ₂ is O, S, or NR ₃ ,
Wherein R ₃ is C _6-60 aryl; Or C _2-60 heteroaryl containing one or more of O, N, Si and S,
L is a bond; C _6-60 arylene; Or C _2-60 heteroarylene containing one or more of O, N, Si and S,
Ar ₁ is any one selected from the group consisting of:

In the above,
Y ₁ to Y ₃ are each independently CH or N, with the proviso that at least one of Y ₁ to Y ₃ is N,
Y ₄ to Y ₇ are each independently CH or N, with the proviso that at least one of Y ₄ to Y ₇ is N,
Y ₈ and Y ₉ are each independently CH or N, with the proviso that at least one of Y ₈ and Y ₉ is N,
Y ₁₀ and Y ₁₁ are each independently CH or N, with the proviso that at least one of Y ₁₀ and Y ₁₁ is N,
Y ₁₂ and Y ₁₃ are each independently CH or N, with the proviso that at least one of Y ₁₂ and Y ₁₃ is N,
Y ₁₄ and Y ₁₅ are each independently CH or N, with the proviso that at least one of Y ₁₄ and Y ₁₅ is N,
Ar ₂ to Ar ₇ are each independently C _6-60 aryl; Or C _2-60 heteroaryl containing one or more of O, N, Si and S;
The method according to claim 1,
R < ₁ > and R < ₂ >
compound.
The method according to claim 1,
R < ₃ > is phenyl,
compound.
The method according to claim 1,
L is a bond, phenylene, or naphthalene diyl,
compound.
The method according to claim 1,
Ar ₂ and Ar ₃ are each independently phenyl, biphenyl, or pyridinyl,
compound.
The method according to claim 1,
Ar ₄ to Ar ₇ are each independently phenyl, biphenyl, naphthyl, or carbazolyl,
compound.
The method according to claim 1,
Ar < _{1 >} is any one selected from the group consisting of:
compound:

The method according to claim 1,
Wherein said compound is any one selected from the group consisting of:
compound:

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 a compound according to any one of claims 1 to 8 The organic light-emitting device.

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