KR101917858B1 - Novel hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel indenocarbazole-based compound and an organic light emitting device comprising the same.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel compound and an organic light emitting device including the same.

The present invention relates to a novel indenocarbazole-based 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 indenocarbazole-based 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,

A is a benzene ring fused to adjacent pentagonal rings and pyrrole rings,

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,

이고,R is

ego,

Two of X ₁ to X ₄ are N, the other is C bonded to L and the other is CR ₂ ,

Y is (CH ₃₎ S, O or -C ₂ -, and

R ₁ is hydrogen; heavy hydrogen; halogen; Nitrile; Nitro; Amino; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; A substituted or unsubstituted C _2-60 alkenyl group; Substituted or unsubstituted C _6-60 aryl; Or a C _2-60 heterocyclic group containing at least one of substituted or unsubstituted O, N, Si and S,

R ₂ is substituted or unsubstituted C _3-60 cycloalkyl; A substituted or unsubstituted C _2-60 alkenyl group; Substituted or unsubstituted C _6-60 aryl; Or a C _2-60 heterocyclic group containing 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).

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

Quot; means a bond connected to another substituent.

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; Cycloalkyl groups; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Arylphosphine groups; Or a heterocyclic group containing at least one of N, O and S atoms, or a substituted or unsubstituted group in which at least two of the above-exemplified substituents are connected to each other . For example, the "substituent group to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

In the present specification, the carbon number of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

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

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

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

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

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, But are not limited to, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl and 5-methylhexyl.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

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

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

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

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

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

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

In Formula 1, A is a benzene ring fused with adjacent pentagonal rings and pyrrole rings, and may be represented by any one of the following Formulas 1-1 to 1-6, depending on the fused position.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Chemical Formula 1-6]

Preferably, L is a bond; Or phenylene. More preferably, L is a bond; 1,3-phenylene; Or 1,4-phenylene.

Preferably, R < ₁ > is hydrogen.

Preferably, R is any one selected from the group consisting of:

Preferably, R < ₂ > is phenyl or biphenyl.

More preferably, R is any one selected from the group consisting of:

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

The compounds represented by Formulas 1-1 to 1-4 may be prepared according to the following Reaction Scheme 1.

[Reaction Scheme 1]

In the above Reaction Scheme 1, X is a halogen group.

X-L-R in the above Reaction Scheme 1 can be prepared by a process as shown in Reaction Scheme 2 below.

[Reaction Scheme 2]

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 material is a layer for injecting holes from the electrode. The hole injecting material has a hole injecting effect, a hole injecting effect in the anode, and an excellent hole injecting effect in the light emitting layer or the light emitting material. A compound which prevents the exciton from migrating to the electron injection layer or the electron injection material and is also excellent in the thin film forming ability is preferable. It is 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 material is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material 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 intermediate A

1) Preparation of intermediate A1

(60.0 g, 0.29 mol) was dissolved in CHCl _{3 (} 500 mL), NBS (46.8 g, 0.29 mol) was added in 5 portions at 0 ° C, and the mixture was stirred at room temperature And stirred for 1 hour. Thereafter, the solution was reduced in pressure, dissolved in ethyl acetate, washed with water, and then the organic layer was separated and reduced in pressure to remove any solvent. Intermediate A1 was obtained (67.1 g, yield 81%, MS: [M + H] ⁺ = 288) by column chromatography.

2) Preparation of intermediate A2

(67.1 g, 0.23 mol) and (2-chlorophenyl) boronic acid (31.2 g, 0.26 mol) were dissolved in 660 mL of tetrahydrofuran in a nitrogen atmosphere, and then a 1.5M aqueous potassium carbonate solution (200 mL) Bis (tri-tert-butylphosphine) palladium (0) (1.2 g, 2.3 mmol) was added thereto, followed by heating with stirring for 2 hours. (56.4 g, yield 76%, MS: [M + H 2] < + >. [0218] The intermediate A2 was prepared by recrystallization using hexane and drying, ] ⁺ = 320).

3) Preparation of intermediate A

(54.4 g, 0.18 mol) and K ₂ CO ₃ (48.7 g, 0.35 mol) were dissolved in 550 mL of dimethylacetamide, and Pd (OAc) ₂ (4.0 g, 17.6 mmol) Lt; / RTI > The temperature was lowered to room temperature and the precipitated solid was filtered and washed with water. The filter cake was dissolved in 1 L of chloroform, washed with water, and then the organic layer was separated to remove the solvent. Recrystallization with ethyl acetate gave 42.4 g (85% yield, MS: [M + H] ⁺ = 284) of intermediate A.

Manufacturing example  2: Preparation of intermediate B

1) Preparation of intermediate B1

(50.0 g, 0.25 mol) and (2- (2-hydroxypropan-2-yl) phenyl) boronic acid (49.1 g, 0.27 mol) were dissolved in 500 mL of dioxane in a nitrogen atmosphere. After dissolving, K ₃ PO ₄ (131.5 g, 0.62 mol) was added and bis (tri-tert-butylphosphine) palladium (0) (1.2 g, 2.5 mmol) was added and the mixture was heated with stirring for 7 hours. The intermediate B1 was prepared (61.2 g, yield 82%, MS: [M + H] +) after drying on anhydrous magnesium sulfate, followed by recrystallization using ethyl acetate and drying. H] < ⁺ > = 302).

2) Preparation of intermediate B

In a nitrogen atmosphere, Intermediate B1 (61.2 g, 0.20 mol) and 340 mL of acetic acid were added, 1.4 mL of H ₂ SO ₄ was slowly added, and the mixture was heated and stirred for 2.5 hours. The temperature was lowered to room temperature and the precipitated solid was filtered and washed with water. The filter cake was dissolved in 1 L of chloroform, washed with water, and then the organic layer was separated to remove the solvent. This intermediate B was obtained using ethyl acetate (52.1 g, 91% yield, MS: [M + H] < ⁺ > = 284).

Manufacturing example  3: Preparation of intermediates C and D

1) Preparation of intermediate C1

Intermediate C1 was prepared in the same manner as Intermediate B1 except that 2-chloro-9H-carbazole was used instead of 1-chloro-9H-carbazole.

2) Preparation of intermediates C and D

In a nitrogen atmosphere, Intermediate C1 (75.2 g, 0.25 mol) and 410 mL of acetic acid were added, and 1.8 mL of H ₂ SO ₄ was slowly added thereto, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature and the precipitated solid was filtered and washed with water. The filter cake was dissolved in 1 L of chloroform, washed with water, and then the organic layer was separated to remove the solvent. This was purified by column chromatography to separate intermediate C and intermediate D.

Manufacturing example  4: Preparation of intermediate E

1) Preparation of intermediate E1

Intermediate E1 was prepared in the same manner as Intermediate B1 except that 3-chloro-9H-carbazole was used instead of 1-chloro-9H-carbazole.

2) Preparation of intermediate E

Intermediate E was prepared in the same manner as Intermediates C and D except for using Intermediate E1 instead of Intermediate C1.

Manufacturing example  5: Preparation of intermediate G

1) Preparation of intermediate G1

Intermediate G1 was prepared in the same manner as Intermediate B1 except that 4-chloro-9H-carbazole was used instead of 1-chloro-9H-carbazole.

2) Preparation of intermediate G

Intermediate G was prepared in the same manner as Intermediate B except for using Intermediate G1 instead of Intermediate B1.

Manufacturing example  6: Preparation of Intermediate H

1) Preparation of intermediate H1

A mixture of methyl 3-aminobenzo-thiophene-2-carboxylate (65.0 g, 313.6 mmol) and urea (84.8 g, 1.41 mol) was stirred in a 2000 mL round-bottomed flask at 200 ° C for 2 hours. The reaction mixture was cooled to room temperature and then poured into sodium hydroxide solution. The impurities were removed by filtration and the reaction product was acidified (HCl, 2N) and the resulting precipitate was dried to obtain Intermediate H1 (52.6 g, yield 77%).

2) Preparation of Intermediate H

A 1000 mL round flask was charged with a mixture of compound H1 (52.6 g, 0.24 mol) and phosphorus oxychloride (750 mL) at reflux for 7.5 hours. The reaction mixture was cooled to room temperature and poured into ice / water with vigorous stirring to produce a precipitate. The resulting reaction product was filtered to obtain Intermediate H (51.0 g, yield 83%, white solid).

Manufacturing example  7: Preparation of intermediate I

1) Preparation of Compound I1

A mixture of methyl 3-aminobenzofuran-2-carboxylate (65.0 g, 340.0 mmol) and urea (91.9 g, 1.5 mol) was stirred in a 2000 mL round-bottomed flask at 200 ° C for 2 hours. The reaction mixture was cooled to room temperature and then poured into a sodium hydroxide solution and the impurities were removed by filtration. The reaction product was acidified (HCl, 2N) and the resulting precipitate was dried to obtain Intermediate I1 (49.4 g, yield 72%).

2) Preparation of Compound I

A 1000 mL round flask was charged with a mixture of intermediate I1 (49.4 g, 0.24 mol) and phosphorus oxychloride (720 mL) under reflux for 7.5 hours. The reaction mixture was cooled to room temperature and poured into ice / water with vigorous stirring to produce a precipitate. The resulting reaction product was filtered to obtain Intermediate I (45.1 g, yield 77%, white solid).

Manufacturing example  8: Preparation of intermediate H2

Intermediate H (15 g, 57.8 mmol) and phenylboronic acid (7.9 g, 64.7 mmol) were dissolved in 250 mL of tetrahydrofuran in a nitrogen atmosphere, and a 1.5M aqueous potassium carbonate solution (120 mL) (Triphenylphosphine) palladium (1.4 g, 1.28 mmol) was added thereto, followed by heating and stirring for 7 hours. (14.1 g, yield 83%, MS: [M + H] +) was prepared by reducing the temperature to room temperature, separating the water layer, drying with anhydrous magnesium sulfate, concentrating under reduced pressure, recrystallization using chloroform and ethanol, H] < ⁺ > = 297).

Manufacturing example  9: Preparation of intermediate H3

Intermediate H3 was prepared in the same manner as Intermediate H2 except that (1,1'-biphenyl) -4-ylboronic acid was used in place of phenylboronic acid.

Manufacturing example  10: Preparation of intermediate H4

Intermediate H4 was prepared in the same manner as Intermediate H2 except that (l, l'-biphenyl) -3-ylboronic acid was used in place of phenylboronic acid.

Manufacturing example  11: Preparation of intermediate H5

(21.4 g, 0.06 mol) was dissolved in 200 mL of dioxane followed by the addition of K ₃ PO ₄ (21.4 g, 0.1 mol), bis (4-chlorophenyl) boronic acid Palladium (0) (0.26 g, 0.5 mmol) were added thereto, and the mixture was heated and stirred for 13 hours. The reaction mixture was concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate to give Intermediate H4 (14.1 g, yield 81%, MS: [M + H] < ⁺ > = 373).

Manufacturing example  12: Preparation of intermediate H6

Intermediate H6 was prepared in the same manner as Intermediate H5 except that (3-chlorophenyl) boronic acid was used instead of (4-chlorophenyl) boronic acid.

Manufacturing example  13: Preparation of intermediate I2

Intermediate I2 was prepared in the same manner as Intermediate H2 except that Intermediate I was used instead of Intermediate H.

Manufacturing example  14: Preparation of intermediate I3

Intermediate I3 was prepared in the same manner as Intermediate H except that Intermediate I and (1,1'-biphenyl) -4-ylboronic acid were used instead of Intermediate H and phenylboronic acid.

Manufacturing example  15: Preparation of intermediate I4

Intermediate I4 was prepared in the same manner as Intermediate H except that Intermediate I and (1,1'-biphenyl) -3-ylboronic acid were used instead of Intermediate H and phenylboronic acid.

Manufacturing example  16: Preparation of intermediate I5

Intermediate I5 was prepared in the same manner as Intermediate H2 except that Intermediate I and (4-chlorophenyl) boronic acid were used in place of Intermediate H and phenylboronic acid.

Manufacturing example  17: Preparation of intermediate I6

Intermediate I6 was prepared in the same manner as Intermediate H, except that Intermediate I and (3-chlorophenyl) boronic acid were used instead of phenylboronic acid.

[ Example ]

Example  1: Preparation of compound 1

Intermediate A (8.0 g, 28.2 mmol), intermediate H2 (8.4 g, 28.2 mmol) and NaOt-Bu (5.42 g, 56.5 mmol) were dissolved in 120 mL of xylene and bis (tri- tert-butylphosphine) palladium (0) (0.29 g, 0.57 mmol) was added, and the mixture was refluxed and stirred. After 7 hours, the temperature was lowered to room temperature, filtered, and washed with water to remove the base. Methyl-2-pyrrolidone to obtain Compound 1 (10.7 g, yield 70%, MS: [M + H] ⁺ = 544).

Example  2: Preparation of compound 2

1) Preparation of intermediate J1

Intermediate A (12.0 g, 42.3 mmol), Intermediate H (10.8 g, 42.3 mmol) and NaOt-Bu (8.1 g, 84.7 mmol) were dissolved in 200 mL of xylene and bis (tri- tert-butylphosphine) palladium (0) (0.43 g, 0.85 mmol) were added, and the mixture was refluxed and stirred. After 4 hours, the temperature was lowered to room temperature, and the filter was washed with water to remove the base. Recrystallization using tetrahydrofuran and N-methyl-2-pyrrolidone gave 19.1 g (90% yield, MS: [M + H] ⁺ = 502) of intermediate J1.

2) Preparation of Example 2

After dissolving Intermediate J1 (7.0 g, 13.8 mmol) and phenylboronic acid (1.7 g, 13.8 mmol) in 100 mL of dioxane, K ₃ PO ₄ (5.91 g, 27.9 mmol) -Butylphosphine) palladium (0) (0.14 g, 0.28 mmol) were added thereto, followed by heating and stirring for 10 hours. After the mixture was cooled to room temperature, the water layer was separated and removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized using N-methyl-2-pyrrolidone and dried to obtain Compound 2 (6.3 g, yield 83% , MS: [M + H] < ⁺ > = 544).

Example  3: Preparation of compound 3

Compound 3 was prepared in the same manner as Compound 2 except for using (1,1'-biphenyl) -4-ylboronic acid in place of phenylboronic acid.

MS: [M + H] < ⁺ > = 620

Example  4: Preparation of compound 4

Compound 4 was prepared in the same manner as Compound 2 except for using (1,1'-biphenyl) -3-ylboronic acid in place of phenylboronic acid.

MS: [M + H] < ⁺ > = 620

Example  5: Preparation of compound 5

Compound 5 was prepared in the same manner as Compound 1 except that Intermediate H3 was used instead of Intermediate H2.

MS: [M + H] < ⁺ > = 620

Example  6: Preparation of Compound 6

Compound 6 was prepared in the same manner as Compound 1 except that Intermediate H4 was used instead of Intermediate H2.

MS: [M + H] < ⁺ > = 620

Example  7: Preparation of Compound 7

Compound 7 was prepared in the same manner as Compound 1 except that Intermediate B was used instead of Intermediate A.

MS: [M + H] < ⁺ > = 544

Example  8: Preparation of compound 8

Compound 8 was prepared in the same manner as Compound 1 except that Intermediate B and Intermediate H3 were used instead of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 620

Example  9: Preparation of Compound 9

Compound 9 was prepared in the same manner as Compound 1 except that Intermediate B and Intermediate H4 were used instead of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 620

Example  10: Preparation of compound 10

Compound 10 was prepared in the same manner as Compound 1 except for using Intermediate A instead of Intermediate C4.

MS: [M + H] < ⁺ > = 544

Example  11: Preparation of compound 11

Compound 11 was prepared in the same manner as Compound 1 except that Intermediate C and Intermediate H3 were used instead of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 620

Example  12: Preparation of Compound 12

Compound 12 was prepared in the same manner as Compound 1 except that Intermediate C and Intermediate H4 were used instead of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 620

Example  13: Preparation of compound 13

Compound 13 was prepared in the same manner as Compound 1 except for using Intermediate D instead of Intermediate A.

MS: [M + H] < ⁺ > = 544

Example  14: Preparation of compound 14

Compound 14 was prepared in the same manner as Compound 1 except that Intermediate D and Intermediate H3 were used instead of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 620

Example  15: Preparation of compound 15

Compound 15 was prepared in the same manner as Compound 1 except that Intermediate D and Intermediate H4 were used instead of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 620

Example  16: Preparation of compound 16

Compound 16 was prepared in the same manner as Compound 1 except that Intermediate E was used instead of Intermediate A.

MS: [M + H] < ⁺ > = 544

Example  17: Preparation of compound 17

Compound 17 was prepared in the same manner as Compound 1 except for using Intermediate E and Intermediate H3 in place of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 620

Example  18: Preparation of compound 18

Compound 18 was prepared in the same manner as Compound 1 except for using Intermediate E and Intermediate H4 instead of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 620

Example  19: Preparation of compound 19

Compound 19 was prepared in the same manner as Compound 1 except that Intermediate G was used instead of Intermediate A.

MS: [M + H] < ⁺ > = 544

Example  20: Preparation of compound 20

Compound 20 was prepared in the same manner as Compound 1 except for using Intermediate G and Intermediate H3 in place of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 620

Example  21: Preparation of compound 21

Compound 21 was prepared in the same manner as Compound 1 except for using Intermediate G and Intermediate H4 in place of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 620

Example  22: Preparation of compound 22

Compound 22 was prepared in the same manner as Compound 1 except that Intermediate H5 was used instead of Intermediate H2.

MS: [M + H] < ⁺ > = 620

Example  23: Preparation of compound 23

Compound 23 was prepared in the same manner as Compound 1 except that Intermediate H6 was used instead of Intermediate H2.

MS: [M + H] < ⁺ > = 620

Example  24: Preparation of Compound 24

Compound 24 was prepared in the same manner as Compound 1 except that Intermediate I2 was used instead of Intermediate H2.

MS: [M + H] < ⁺ > = 528

Example  25: Preparation of compound 25

Compound 25 was prepared in the same manner as Compound 1 except that Intermediate I3 was used instead of Intermediate H2.

MS: [M + H] < ⁺ > = 604

Example  26: Preparation of Compound 26

Compound 26 was prepared in the same manner as Compound 1 except that Intermediate I4 was used instead of Intermediate H2.

MS: [M + H] < ⁺ > = 604

Example  27: Preparation of compound 27

1) Preparation of intermediate J2

Intermediate J2 was prepared in the same manner as Intermediate J1 except that Intermediate I was used instead of Intermediate H.

2) Preparation of compound 27

Compound 27 was prepared in the same manner as compound 2 except that intermediate J2 was used instead of intermediate J1.

MS: [M + H] < ⁺ > = 528

Example  28: Preparation of compound 28

Compound 28 was prepared in the same manner as Compound 2 except that Intermediate J1 and Intermediate J2 were used instead of phenylboronic acid and (1,1'-biphenyl) -4-ylboronic acid was used.

MS: [M + H] < ⁺ > = 604

Example  29: Preparation of compound 29

Compound 29 was prepared in the same manner as compound 2 except that Intermediate J1 was used instead of Intermediate J2 and (1,1'-biphenyl) -3-ylboronic acid instead of phenylboronic acid.

MS: [M + H] < ⁺ > = 604

Example  30: Preparation of compound 30

Compound 30 was prepared in the same manner as Compound 1 except that Intermediate B and Intermediate I2 were used instead of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 528

Example  31: Preparation of Compound 31

Compound 31 was prepared in the same manner as Compound 1 except that Intermediate B and Intermediate I3 were used instead of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 604

Example  32: Preparation of compound 32

Compound 32 was prepared in the same manner as Compound 1 except that Intermediate C and Intermediate I2 were used instead of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 528

Example  33: Preparation of compound 33

Compound 33 was prepared in the same manner as Compound 1 except that Intermediate C and Intermediate I4 were used instead of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 604

Example  34: Preparation of compound 34

Compound 34 was prepared in the same manner as Compound 1 except that Intermediate D and Intermediate I2 were used instead of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 528

Example  35: Preparation of compound 35

Compound 35 was prepared in the same manner as Compound 1 except that Intermediate D and Intermediate I3 were used instead of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 604

Example  36: Preparation of compound 36

Compound 36 was prepared in the same manner as Compound 1 except for using Intermediate D and Intermediate I4 instead of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 604

Example  37: Preparation of Compound 37

Compound 37 was prepared in the same manner as Compound 1 except for using Intermediate E and Intermediate I2 instead of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 528

Example  38: Preparation of compound 38

Compound 38 was prepared in the same manner as Compound 1 except for using Intermediate E and Intermediate I3 instead of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 604

Example  39: Preparation of compound 39

Compound 39 was prepared in the same manner as Compound 1 except for using Intermediate G and Intermediate I2 instead of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 528

Example  40: Preparation of compound 40

Compound 40 was prepared in the same manner as Compound 1 except for using Intermediate G and Intermediate I4 in place of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 604

Example  41: Preparation of compound 41

Compound 41 was prepared in the same manner as Compound 1 except that Intermediate I5 was used instead of Intermediate H2.

MS: [M + H] < ⁺ > = 604

Example  42: Preparation of compound 42

Compound 42 was prepared in the same manner as Compound 1 except that Intermediate I6 was used instead of Intermediate H2.

MS: [M + H] < ⁺ > = 604

Example  43: Preparation of compound 43

Compound 43 was prepared in the same manner as Compound 1 except for using Intermediate D and Intermediate I5 instead of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 604

Example  44: Preparation of compound 44

Compound 44 was prepared in the same manner as Compound 1 except that Intermediate D and Intermediate I6 were used instead of Intermediate A and Intermediate H2.

MS: [M + H] < ⁺ > = 604

[ Experimental Example ]

Experimental Example  One

A thin glass substrate coated with ITO (indium tin oxide) at a thickness of 1,300 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water, which was filtered with a filter of Millipore Co., was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

The following HI-1 compound was thermally vacuum deposited on the ITO transparent electrode prepared above to a thickness of 50 Å to form a hole injection layer. The following HT-1 compound was thermally vacuum deposited on the hole injection layer to form a hole transport layer, and HT-2 compound was vacuum deposited on the HT-1 vapor deposition layer to a thickness of 50 Å to form an electron blocking layer. Subsequently, Compound 1 prepared above and Dp-25 compound shown below were co-deposited on the HT-2 deposited film at a weight ratio of 12% to form a 400 Å thick light emitting layer. The following ET-1 compound was vacuum-deposited on the light-emitting layer to a thickness of 250 ANGSTROM, and the following ET-2 compound was co-deposited with Li at a weight ratio of 2% to a thickness of 100 ANGSTROM to form an electron transport layer and an electron injection layer. Aluminum was deposited on the electron injecting layer to a thickness of 1000 to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the deposition rate of aluminum was maintained at 2 Å / sec, and the vacuum degree during deposition was maintained at 1 × 10 ^-7 to 5 × 10 ^-8 torr Respectively.

Experimental Example  2 to 12

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

compare Experimental Example  1 to 4

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that the compound described in the following Table 1 was used instead of the compound 1 in Experimental Example 1. In the following Table 1, C1, C2, C3 and C4 mean respectively the following compounds.

Experimental Example  13

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1 and H-2 were used in a ratio of 50:50 instead of Compound 1 in Experimental Example 1.

Experimental Example  14 to 20

An organic light emitting device was fabricated in the same manner as in Experimental Example 13, except that the compound described in the following Table 1 was used instead of the Compound 1 in Experimental Example 13. In the following Table 1, C1, C2, C3 and C4 mean respectively the following compounds.

compare Experimental Example  5 to 7

An organic light emitting device was fabricated in the same manner as in Experimental Example 13, except that the compound described in the following Table 1 was used instead of the Compound 1 in Experimental Example 13. C1, C2 and C3 in the following Table 1 are as described in Comparative Experimental Examples 1 to 4 above.

The driving voltage, efficiency, luminescent color, and lifetime were measured by applying current to the organic light emitting device manufactured in the Experimental Examples and Comparative Experimental Examples, and the results are shown in Table 1 below. The lifetime (T95) is defined as the time required for the luminance to decrease to 95% when the initial luminance is taken as 100%, and is measured at a current density of 20 mA / cm ² .

compound Voltage (V)
(@ 10 mA / cm ² ) Efficiency (cd / A)
(@ 10 mA / cm ² ) Luminous color T95 (hr)
(@ 20 mA / cm ² ) Experimental Example 1 One 2.80 65.0 green 61 Experimental Example 2 2 2.77 66.0 green 60 Experimental Example 3 6 2.76 65.9 green 58 Experimental Example 4 8 2.79 65.7 green 62 Experimental Example 5 12 2.76 65.6 green 57 Experimental Example 6 13 2.75 65.5 green 60 Experimental Example 7 16 2.74 65.3 green 57 Experimental Example 8 22 2.86 65.8 green 55 Experimental Example 9 24 2.91 64.3 green 57 Experimental Example 10 27 2.93 64.9 green 56 Experimental Example 11 34 2.95 65.2 green 59 Experimental Example 12 37 2.94 65.1 green 57 Experimental Example 13 1, H-2 3.20 73.9 green 175 Experimental Example 14 3, H-2 3.23 72.8 green 170 Experimental Example 15 15, H-2 3.25 74.0 green 177 Experimental Example 16 16, H-2 3.25 73.5 green 175 Experimental Example 17 20, H-2 3.29 74.2 green 173 Experimental Example 18 22, H-2 3.30 74.1 green 174 Experimental Example 19 24, H-2 3.35 74.5 green 170 Experimental Example 20 34, H-2 3.35 75.0 green 168 Comparative Experimental Example 1 C1 3.01 60.0 green 40 Comparative Experimental Example 2 C2 3.19 64.5 green 42 Comparative Experimental Example 3 C3 3.20 64.2 green 46 Comparative Experimental Example 4 C4 3.35 63.9 green 43 Comparative Experiment Example 5 C1, H-2 3.52 67.0 green 140 Comparative Experimental Example 6 C2, H-2 3.73 70.5 green 140 Comparative Example 7 C3, H-2 3.80 70.0 green 141

As shown in Table 1, the compound of the present invention showed an advantage in terms of voltage and efficiency, and the lifetime of the compound of the present invention was increased by about 40 to 50% more than that of Compound C1 which was a conventional green luminescent host material. In addition, when two-component host was used, it was confirmed that it exhibited better performance in that it has long-life characteristics and low-voltage 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 (11)

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

In Formula 1,
A is a benzene ring fused to adjacent pentagonal rings and pyrrole rings,
L is a bond; Or phenylene,
R is

ego,
Two of X ₁ to X ₄ are N, the other is C bonded to L and the other is CR ₂ ,
Y is (CH ₃₎ S, O or -C ₂ -, and
R ₁ is hydrogen; heavy hydrogen; halogen; Nitrile; Nitro; Amino; C _1-60 alkyl; C _3-60 cycloalkyl; A C _2-60 alkenyl group; C _6-60 aryl; Or a C _2-60 heterocyclic group containing at least one of O, N, Si and S,
R ₂ is phenyl or biphenyl. The method according to claim 1,
(1) is represented by any one of the following formulas (1-1) to (1-6)
compound:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Chemical Formula 1-6]

.
delete The method according to claim 1,
And R is any one selected from the group consisting of:
compound:

.
delete The method according to claim 1,
And R 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 the following compounds:
compound:

.
A first electrode; A second electrode facing the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes at least one layer selected from the group consisting of the first, second, fourth, sixth, And a compound according to any one of claims 1 to 7.
9. The method of claim 8,
The organic compound layer containing the compound may include a hole injection layer; A hole transport layer; Or a layer which simultaneously injects holes and transports holes.
Organic light emitting device.
9. The method of claim 8,
The organic compound layer containing the compound may include an electron injection layer; An electron transport layer; Or a layer which simultaneously performs electron injection and electron transport.
Organic light emitting device.
9. The method of claim 8,
Wherein the organic compound layer containing the compound is a light emitting layer.
Organic light emitting device.

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