KR20190140659A - Novel compound and organic light emittng device comprising the same - Google Patents

Abstract

The present invention provides a novel compound and an organic light emitting device using the same. The compound represented by chemical formula 1 can be used as a material of an organic material layer of the organic light emitting device, and can improve efficiency, lower a driving voltage, and/or improve lifespan characteristics in the organic light emitting device.

Description

Novel compound and organic light emitting device using the same {NOVEL COMPOUND AND ORGANIC LIGHT EMITTNG DEVICE COMPRISING THE SAME}

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

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage and response speed characteristics, many studies have 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. In order to increase the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multi-layered structure composed of different materials. For example, the organic layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. When it falls back to the ground, it glows.

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

Korean Patent Publication No. 10-2000-0051826

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

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

[Formula 1]

In Chemical Formula 1,

X is O, S, Se, P (R ₇ ) or C (R ₇ ) ₂ ,

a, b, c and d are each independently an integer of 1 to 4,

R ₁ to R ₇ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _1-60 haloalkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkoxy; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted C _6-60 aryloxy; Substituted or unsubstituted C _6-60 arylamine; Or C _1-60 heteroaryl including one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S, wherein at least one of R ₃ to R ₆ is represented by the following Chemical Formula 2 Become,

[Formula 2]

In Chemical Formula 2,

L ₁ to L ₃ are each independently a single bond; Substituted or unsubstituted C _6-60 arylene; Or C _1-60 heteroarylene containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted O, N, Si, and S,

Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-60 aryl; Or C _1-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted O, N, Si and S.

In addition, the present invention is a first electrode; A second electrode provided to face 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 Chemical Formula 1. to provide.

The compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting diode, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode.

FIG. 1 shows an example of an organic light emitting element composed of 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 consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4. It is.

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

The present invention provides a compound represented by Chemical Formula 1.

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

Means a bond connected to another substituent.

As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Cyano group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl including one or more of N, O and S atoms, or substituted or unsubstituted with two or more substituents in the above-described substituents. . For example, when the "substituent to which two or more substituents are linked" is a biphenyl group, the biphenyl may be interpreted as an aryl group substituted with one phenyl group or a substituent to which two phenyl groups are linked.

Although carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

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

In this specification, although carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

In the present specification, specifically, the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. However, the present invention is not limited thereto.

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

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 chain, carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary 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, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 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 an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, but may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. The polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, or the like, but is not limited thereto.

In the present specification, the heteroaryl is a heteroaryl containing one or more of O, N, Si, and S as heterologous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heteroaryl include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridil group, Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, Carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiadiazolyl Groups, phenothiazinyl groups, dibenzofuranyl groups, and the like, but are not limited thereto.

In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the alkyl group described above. In the present specification, the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heteroaryl. In the present specification, the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above. In the present specification, the description of the aryl group described above may be applied except that the arylene is a divalent group. In the present specification, the description of the aforementioned heteroaryl may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aforementioned aryl group or cycloalkyl group may be applied except that two substituents are formed by bonding. In the present specification, the heterocycle is not a monovalent group, and the description of the aforementioned heteroaryl may be applied except that two substituents are formed by bonding.

In Formula 1, R ₁ and R ₂ are each independently a substituted or unsubstituted C _1-60 alkyl; Or substituted or unsubstituted C _6-60 aryl.

For example, R ₁ and R ₂ can be methyl or phenyl.

Preferably, Formula 1 may be any one of the compounds of Formulas 1-1 to 1-4.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Chemical Formulas 1-1 to 1-4, description of X, L ₁ to L ₃ , Ar _1, and Ar ₂ is as defined above.

Preferably, in Chemical Formula 1, L ₁ to L ₃ may each independently be any one selected from the group consisting of a single bond or the following.

Preferably, in Chemical Formula 1, X may be O, S, C (CH ₃ ) ₂ or C (C ₆ H ₅ ) ₂ .

Preferably, in Formula 1, Ar ₁ and Ar ₂ may each independently be any one selected from the group consisting of:

For example, the compound may be selected from the group consisting of the following compounds:

On the other hand, the compound represented by the formula (1) can be prepared by the production method such as the following schemes 1-2. In Schemes 1 and 2 below, X, R ₁ , R ₂ , L ₁ , L ₂ , L ₃ , Ar ₁ and Ar ₂ are as defined above, Y ₁ , Y ₂ are halogen, preferably bromo Or chloro.

Scheme 1

Scheme 2

Specifically, in Scheme 1, core 1 is synthesized through the coupling and cyclization reaction of 1-a and 1-b, and 1-c, which is core 1 and secondary amine, is 1-1 through amination coupling reaction. And 1-2 are synthesized through a Suzuki coupling reaction between core 1-1 and boronic acid 1-d. In addition, Core 2 is synthesized through coupling and cyclization reaction of 2-a and 2-b in Scheme 2, and 2-1 is synthesized through amination coupling reaction of 2-c which is core 2 and a secondary amine. 2-2 is synthesize | combined through the Suzuki coupling reaction of the core 2 and 2-d which is boronic acid.

The manufacturing method may be more specific in the synthesis examples to be described later.

The present invention also provides an organic light emitting device including the compound represented by Chemical Formula 1. In one embodiment, the present invention is a first electrode; A second electrode provided to face 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 Chemical Formula 1. to provide.

The organic material layer of the organic light emitting device of the present invention may be formed of a single layer structure, but may be formed of 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 injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

Specifically, the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1.

In this case, the compound represented by Chemical Formula 1 may be used as a host material in the emission layer.

In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure in which an anode, one or more organic material 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 organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.

FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer.

FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4. It is. In such a structure, the compound represented by Formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the light emitting layer and the electron transport layer.

The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1. In addition, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, an anode is formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. In addition, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, and then, a material that may be used as a cathode may be deposited thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound represented by Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.

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

As the anode material, a material having a large work function is generally preferred to facilitate hole injection into 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), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SNO ₂ : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is 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; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode. The hole injection material has a capability of transporting holes to have a hole injection effect at an anode, and has an excellent hole injection effect for a light emitting layer or a light emitting material. The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. A hole transporting material is a material capable of transporting holes from an anode or a hole injection layer and transferring them to the light emitting layer. This is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; 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 containing compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted. At least one arylvinyl group is substituted with the arylamine, and one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.

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

The electron injection layer is a layer for injecting electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, 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-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.

The organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-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 the organic light emitting device.

Preparation of the compound represented by Chemical Formula 1 and an organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.

Example  1: Synthesis of Compound 1

Step 1-1) Synthesis of Compound 1-A

1-bromo-2-phenoxybenzene (50.00 g, 200.71 mmol) was dissolved in tetrahydrofuran (THF) (300 ml) and the temperature was lowered to -78 ° C. 1.6 M n-butyllithium (125 ml) was slowly added to the solution, followed by stirring for 10 minutes. 2-bromo-10,10-dimethylanthracene-9 ( 10H ) -one (60.45 g, 200.71 mmol) was dissolved in tetrahydrofuran (THF) (300 ml) and slowly added to the solution. After completion of the reaction, 1 N hydrochloric acid (500 ml) was added thereto, and the layers were separated. After removing the solvent, acetic acid (800 ml) was added thereto, refluxed and stirred, and sulfuric acid (cat.) Was added dropwise. After completion of the reaction and filtration, the layers were separated by chloroform and aqueous sodium hydrogen carbonate (NaHCO 3) solution. After removal of the solvent, recrystallization with ethyl acetate yielded Compound 1-A (70.50 g, 76.92% yield).

Step 1-2) Synthesis of Compound 1

Compound 1-A (20 g, 44.11 mmol) and di ([1.1'-biphenyl] -4-yl) amine (14.46 g, 45.00 mmol) obtained in step 1-1 above and sodium tert-butoxide (5.93) g, 61.75 mmol) was added toluene (200 ml), followed by heating and stirring for 5 minutes. Bis (tri-tert-butylphosphine) palladium (0.045 g, 0.088 mmol) was slowly added dropwise to the solution, followed by heating and stirring for 1 hour. After completion of the reaction and filtration, layered with toluene and water. After removing the solvent and recrystallized with ethyl acetate to give compound 1 (27.30 g, 89.19% yield). (MS [M + H] ⁺ = 694)

Example  2: synthesis of compound 2

1-A (20.00 g, 44.11 mmol) obtained in Step 1-1 of Example 1 and N -([1,1'-biphenyl] -4-yl)-[1,1'-biphenyl] Compound 2 (24.70 g, 80.70% yield) was obtained by the same method as Step 1-2 of Example 1 using 2-amine (14.46 g, 45.00 mmol). (MS [M + H] ⁺ = 694)

Example  3: Synthesis of Compound 3

1-A (20.00 g, 44.11 mmol) and N -([1,1′-biphenyl] -4-yl) -9,9-dimethyl-9 H − obtained in step 1-1 of Example 1 Compound 3 (26.20 g, 80.93% yield) was obtained by the same method as Step 1-2 of Example 1 using fluorene-2-amine (16.26 g, 45.00 mmol). (MS [M + H] ⁺ = 734)

Example  4: Synthesis of Compound 4

1-A (20.00 g, 44.11 mmol) and (4- (di ([1,1'-biphenyl] -4-yl) amino) phenyl) boronic acid obtained in step 1-1 of Example 1 1,4-dioxane (200 ml) was added to 20.44 g, 46.32 mmol), followed by heating and stirring. An aqueous potassium carbonate (18.29 g, 132.33 mmol) solution (60 ml) was added to the solution, followed by heating and stirring for 5 minutes. Bis (tri-tert-butylphosphine) palladium (0.045 g, 0.088 mmol) was slowly added dropwise to the solution, followed by heating and stirring for 1 hour. After completion of the reaction and filtration, layered with toluene and water. After removing the solvent and recrystallized with ethyl acetate to give compound 4 (29.20 g, 85.97% yield). (MS [M + H] ⁺ = 770)

Example  5: Synthesis of Compound 5

Example 1 A 1-A obtained in the step 1-1 of (20.00 g, 44.11 mmol) and (4 - ([1,1'-biphenyl] -4-yl (9,9-dimethyl -9 H - Compound 5 (28.5 g, 79.76% yield) was obtained by the same method as Example 4 using fluoren-2-yl) amino) phenyl) boronic acid (22.30 g, 46.32 mmol). (MS [M + H] ⁺ = 810)

Example  6: Synthesis of Compound 6

Step 6-1) Synthesis of Compound 6-A

This example using 1-bromo-2-phenoxybenzene (50.00 g, 200.71 mmol) and 3-bromo-10,10-dimethylanthracene-9 (10 H ) -one (60.45 g, 200.71 mmol) Compound 6-A (65.50 g, 71.98% yield) was obtained by the same method as Step 1-1 of 1.

Step 6-2) Synthesis of Compound 6

Using compound 6-A (20 g, 44.11 mmol) and di ([1.1'-biphenyl] -4-yl) amine (14.46 g, 45.00 mmol) obtained in step 6-1 of Example 6, Compound 6 (25.50 g, 83.31% yield) was obtained by the same method as Step 1-2 of Example 1. (MS [M + H] ⁺ = 694)

Example  7: Synthesis of Compound 7

Example 6 A 6-A obtained in the step 6-1 of (20.00 g, 44.11 mmol) and N - ([1,1'- biphenyl] -2-yl) 9,9-dimethyl -9 H - Compound 7 (26.40 g, 81.54% yield) was obtained by the same method as Step 1-2 of Example 1 using fluorene-2-amine (16.26 g, 45.00 mmol). (MS [M + H] ⁺ = 734)

Example  8: Synthesis of Compound 8

6-A (20.00 g, 44.11 mmol) and N- (4- (dibenzo [b, d] furan-4-yl) phenyl) -1 [1,1 obtained in step 6-1 of Example 6 Compound 8 (30.2 g, 87.33% yield) was obtained by the same method as Step 1-2 of Example 1 using '-biphenyl] -4-amine (18.52 g, 45.00 mmol). (MS [M + H] ⁺ = 784)

Example  9: Synthesis of Compound 9

6-A (20.00 g, 44.11 mmol) and (4- (di ([1,1'-biphenyl] -4-yl) amino) phenyl) boronic acid obtained in step 6-1 of Example 6 20.44 g, 46.32 mmol) was obtained in the same manner as in Example 4, to obtain compound 9 (28.2 g, 83.03% yield). (MS [M + H] ⁺ = 770)

Example  10: Synthesis of Compound 10

Example 6 A 6-A obtained in the step 6-1 of (20.00 g, 44.11 mmol) and (4 - ([1,1'-biphenyl] -4-yl (9,9-dimethyl -9 H - Compound 10 (29.10 g, 81.44% yield) was obtained by the same method as Example 4 using fluoren-2-yl) amino) phenyl) boronic acid (22.30 g, 46.32 mmol). (MS [M + H] ⁺ = 810)

Example  11: Synthesis of Compound 11

Step 11-1) Synthesis of Compound 11-A

This example using 1-bromo-2-phenoxybenzene (50.00 g, 200.71 mmol) and 4-bromo-10,10-dimethylanthracene-9 (10 H ) -one (60.45 g, 200.71 mmol) Compound 11-A (62.50 g, 68.68% yield) was obtained by the same method as Step 1-1 of 1.

Step 11-2) Synthesis of Compound 11

Using Compound 11-A (20 g, 44.11 mmol) and di ([1.1'-biphenyl] -4-yl) amine (14.46 g, 45.00 mmol) obtained in step 11-1 of Example 11, Compound 11 (23.40 g, 76.45% yield) was obtained by the same method as Step 1-2 of Example 1. (MS [M + H] ⁺ = 694)

Example  12: Synthesis of Compound 12

Step 12-1) Synthesis of Compound 12-A

This example using 1-bromo-2-phenoxybenzene (50.00 g, 200.71 mmol) and 1-bromo-10,10-dimethylanthracene-9 (10 H ) -one (60.45 g, 200.71 mmol) Compound 12-A (60.80 g, 66.81% yield) was obtained by the same method as Step 1-1 of 1.

Step 12-2) Synthesis of Compound 12

Using Compound 12-A (20 g, 44.11 mmol) and di ([1.1'-biphenyl] -4-yl) amine (14.46 g, 45.00 mmol) obtained in step 12-1 of Example 12, Compound 12 (24.30 g, 79.39% yield) was obtained by the same method as Step 1-2 of Example 1. (MS [M + H] ⁺ = 694)

Example  13: Synthesis of Compound 13

Step 13-1) Synthesis of Compound 13-A

The procedure was carried out with 1-bromo-2-phenoxybenzene (50.00 g, 200.71 mmol) and 2-bromo-10,10-diphenylanthracene-9 (10 H ) -one (85.37 g, 200.71 mmol) Compound 13-A (81.80 g, 70.57% yield) was obtained by the same method as Step 1-1 of Example 1.

Step 13-2) Synthesis of Compound 13

Using compound 13-A (20 g, 34.63 mmol) and diphenylamine (5.98 g, 35.32 mmol) obtained in step 13-1 of Example 13, in the same manner as in Step 1-2 of Example 1 Compound 13 (18.50 g, 80.23% yield) was obtained. (MS [M + H] ⁺ = 666)

Example  14: Synthesis of Compound 14

13-A (20.00 g, 34.63 mmol) obtained in Step 13-1 of Example 13 and N -([1,1'-biphenyl] -4-yl)-[1,1'-biphenyl] Compound 14 (23.70 g, 83.66% yield) was obtained by the same method as Step 1-2 of Example 1 using 2-amine (11.35 g, 35.32 mmol). (MS [M + H] ⁺ = 818)

Example  15: Synthesis of Compound 15

Step 15-1) Synthesis of Compound 15-A

The procedure was carried out using 1-bromo-2-phenoxybenzene (50.00 g, 200.71 mmol) and 3-bromo-10,10-diphenylanthracene-9 (10 H ) -one (85.37 g, 200.71 mmol) Compound 15-A (85.00 g, 73.33% yield) was obtained by the same method as Step 1-1 of Example 1.

Step 15-2) Synthesis of Compound 15

Using compound 15-A (20 g, 34.63 mmol) and diphenylamine (5.98 g, 35.32 mmol) obtained in step 15-1 of Example 15, the same method as Step 1-2 of Example 1 was used. Compound 15 (18.80 g, 81.53% yield) was obtained. (MS [M + H] ⁺ = 666)

Example  16: Synthesis of Compound 16

Step 16-1) Synthesis of Compound 16-A

The above was carried out using (2-bromophenyl) (phenyl) sulfan (50.00 g, 188.56 mmol) and 2-bromo-10,10-dimethylanthracene-9 (10 H ) -one (56.79 g, 188.56 mmol) Compound 16-A (62.50 g, 70.61% yield) was obtained by the same method as Step 1-1 of Example 1.

Step 16-2) Synthesis of Compound 16

Using Compound 16-A (20 g, 42.60 mmol) and di ([1.1'-biphenyl] -4-yl) amine (13.97 g, 43.46 mmol) obtained in step 16-1 of Example 16, Compound 16 (26.50 g, 87.62% yield) was obtained by the same method as Step 1-2 of Example 1. (MS [M + H] ⁺ = 710)

Example  17: Synthesis of Compound 17

Step 17-1) Synthesis of Compound 17-A

The above was carried out using (2-bromophenyl) (phenyl) sulfan (50.00 g, 188.56 mmol) and 3-bromo-10,10-dimethylanthracene-9 (10 H ) -one (56.79 g, 188.56 mmol) Compound 17-A (63.80 g, 72.08% yield) was obtained by the same method as Step 1-1 of Example 1.

Step 2) Synthesis of Compound 17

Compound 17-A (20 g, 42.60 mmol) obtained in Step 17-1 of Example 17 with N -([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9 H Compound 17 (25.80 g, 80.75% yield) was obtained by the same method as Step 1-2 of Example 1 using -fluoren-2-amine (15.71 g, 43.46 mmol). (MS [M + H] ⁺ = 750)

Example  18: Synthesis of Compound 18

Step 18-1) Synthesis of Compound 18-A

Using (2-bromophenyl) (phenyl) sulfan (50.00 g, 188.56 mmol) and 3-bromo-10,10-diphenylanthracene-9 (10 H ) -one (80.20 g, 188.56 mmol) Compound 18-A (83.60 g, 74.69% yield) was obtained by the same method as Step 1-1 of Example 1.

Step 18-2) Synthesis of Compound 18

Using compound 18-A (20 g, 33.69 mmol) and diphenylamine (5.82 g, 34.37 mmol) obtained in step 18-1 of Example 18 in the same manner as in Step 1-2 of Example 1 Compound 18 (17.50 g, 76.18% yield) was obtained. (MS [M + H] ⁺ = 682)

Example  19: Synthesis of Compound 19

Step 19-1) Synthesis of Compound 19-A

2-bromo-4-chloro-1-phenoxybenzene (50.00 g, 176.34 mmol) was dissolved in tetrahydrofuran (THF) (300 ml) and the temperature was lowered to -78 ° C. 1.6 M n-butyllithium (110 ml) was slowly added to the solution, followed by stirring for 10 minutes. 10,10-dimethylanthracene-9 ( 10H ) -one (39.20 g, 176.34 mmol) was dissolved in tetrahydrofuran (THF) (300 ml) and slowly added to the solution. After completion of the reaction, 1 N hydrochloric acid (300 ml) was added thereto, and the layers were separated. After removing the solvent, acetic acid (600 ml) was added thereto, refluxed and stirred, and sulfuric acid (cat.) Was added dropwise. After completion of the reaction and filtration, the layers were separated by chloroform and aqueous sodium hydrogen carbonate (NaHCO 3) solution. After removal of the solvent, recrystallization with ethyl acetate yielded Compound 19-A (54.50 g, 75.58% yield).

Step 19-2) Synthesis of Compound 19

Compound 19-A (20.00 g, 48.91 mmol) and di ([1.1'-biphenyl] -4-yl) amine (16.03 g, 49.89 mmol) obtained in step 19-1 of Example 19, and sodium tert- Xylene (200 ml) was added to butoxide (6.58 g, 68.47 mmol), then heated and stirred for 5 minutes. Bis (tri-tert-butylphosphine) palladium (0.125 g, 0.245 mmol) was slowly added dropwise to the solution, followed by heating and stirring for 1 hour. After completion of the reaction and filtration, layered with toluene and water. After removal of the solvent, recrystallization with ethyl acetate afforded Compound 19 (27.10 g, 79.85% yield). (MS [M + H] ⁺ = 694)

Example  20: Synthesis of Compound 20

19-A (20.00 g, 48.91 mmol) obtained in Step 19-1 of Example 19 and N -([1,1'-biphenyl] -4-yl)-[1,1'-biphenyl] Compound 20 (25.30 g, 74.55% yield) was obtained by the same method as Step 19-2 of Example 19 using 2-amine (16.03 g, 49.89 mmol). (MS [M + H] ⁺ = 694)

Example  21: Synthesis of Compound 21

19-A (20.00 g, 48.91 mmol) and N -([1,1′-biphenyl] -2-yl) -9,9-dimethyl-9 H − obtained in step 19-1 of Example 19; Compound 21 (28.30 g, 78.83% yield) was obtained by the same method as Step 19-2 of Example 19, using fluorene-2-amine (18.03 g, 49.89 mmol). (MS [M + H] ⁺ = 734)

Example  22: Synthesis of Compound 22

19-A (20.00 g, 48.91 mmol) and (4- (di ([1,1'-biphenyl] -4-yl) amino) phenyl) boronic acid obtained in step 19-1 of Example 19 22.67 g, 51.36 mmol) was obtained in the same manner as in Example 4, to obtain Compound 22 (29.2 g, 77.54% yield). (MS [M + H] ⁺ = 770)

Example  23: Synthesis of Compound 23

Step 23-1) Synthesis of Compound 23-A

Example 19 using 1-bromo-4-chloro-2-phenoxybenzene (50.00 g, 176.34 mmol) and 10,10-dimethylanthracene-9 (10 H ) -one (39.20 g, 176.34 mmol) Compound 23-A (56.10 g, 77.80% yield) was obtained in the same manner as in Step 19-1.

Step 23-2) Synthesis of Compound 23

Using compound 23-A (20.00 g, 48.91 mmol) and di ([1.1'-biphenyl] -4-yl) amine (16.03 g, 49.89 mmol) obtained in step 23-1 of Example 23, Compound 23 (27.30 g, 80.44% yield) was obtained by the same method as Step 19-2 of Example 19. (MS [M + H] ⁺ = 694)

Example  24: Synthesis of Compound 24

23-A (20.00 g, 48.91 mmol) obtained in step 23-1 of Example 23 and N -([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9 H- Compound 24 (28.40 g, 79.11% yield) was obtained by the same method as Step 19-2 of Example 19, using fluorene-2-amine (18.03 g, 49.89 mmol). (MS [M + H] ⁺ = 734)

Example  25: Synthesis of Compound 25

Step 25-1) Synthesis of Compound 25-A

Example 19 using 1-bromo-3-chloro-2-phenoxybenzene (50.00 g, 176.34 mmol) and 10,10-dimethylanthracene-9 (10 H ) -one (39.20 g, 176.34 mmol) Compound 25-A (45.10 g, 62.54% yield) was obtained in the same manner as in Step 19-1.

Step 25-2) Synthesis of Compound 25

Using Compound 25-A (20.00 g, 48.91 mmol) and di ([1.1'-biphenyl] -4-yl) amine (16.03 g, 49.89 mmol) obtained in step 25-1 of Example 25, Compound 25 (26.20 g, 77.20% yield) was obtained by the same method as Step 19-2 of Example 19. (MS [M + H] ⁺ = 694)

Example  26: Synthesis of Compound 26

Example 25 A 25-A (20.00 g, 48.91 mmol) obtained in the step 25-1 and the (4 - ([1,1'-biphenyl] -4-yl (9,9-dimethyl -9 H - Compound 26 (30.8 g, 77.74% yield) was obtained by the same method as Example 4 using fluoren-2-yl) amino) phenyl) boronic acid (24.72 g, 51.36 mmol). (MS [M + H] ⁺ = 810)

Example  27: Synthesis of Compound 27

Step 27-1) Synthesis of Compound 27-A

Example 19 above using 2-bromo-1-chloro-3-phenoxybenzene (50.00 g, 176.34 mmol) and 10,10-dimethylanthracene-9 (10 H ) -one (39.20 g, 176.34 mmol) Compound 25-A (48.50 g, 67.26% yield) was obtained in the same manner as in Step 19-1.

Step 27-2) Synthesis of Compound 27

Using compound 27-A (20.00 g, 48.91 mmol) and di ([1.1'-biphenyl] -4-yl) amine (16.03 g, 49.89 mmol) obtained in step 27-1 of Example 27, Compound 27 (25.20 g, 74.25% yield) was obtained by the same method as Step 19-2 of Example 19. (MS [M + H] ⁺ = 694)

Example  28: Synthesis of Compound 28

Step 28-1) Synthesis of Compound 28-A

This example using 2-bromo-4-chloro-1-phenoxybenzene (50.00 g, 176.34 mmol) and 10,10-diphenylanthracene-9 (10 H ) -one (61.09 g, 176.34 mmol) Compound 28-A (62.50 g, 66.49% yield) was obtained by the same method as 19-1 of 19.

Step 28-2) Synthesis of Compound 28

Using compound 28-A (20.00 g, 37.52 mmol) and diphenylamine (6.48 g, 38.27 mmol) obtained in step 28-1 of Example 28 in the same manner as in Step 19-2 of Example 19 Compound 28 (21.30 g, 85.26% yield) was obtained. (MS [M + H] ⁺ = 666)

Example  29: Synthesis of Compound 29

Step 29-1) Synthesis of Compound 29-A

This example using 1-bromo-3-chloro-2-phenoxybenzene (50.00 g, 176.34 mmol) and 10,10-diphenylanthracene-9 (10 H ) -one (61.09 g, 176.34 mmol) Compound 29-A (61.80 g, 65.74% yield) was obtained by the same method as 19-1 of 19.

Step 29-2) Synthesis of Compound 29

Using compound 29-A (20.00 g, 37.52 mmol) and di ([1.1'-biphenyl] -4-yl) amine (12.30 g, 38.27 mmol) obtained in step 29-1 of Example 29, Compound 29 (25.70 g, 83.73% yield) was obtained by the same method as Step 19-2 of Example 19. (MS [M + H] ⁺ = 818)

Example  30: Synthesis of Compound 30

Step 30-1) Synthesis of Compound 30-A

This example using (2-bromo-4-chlorophenyl) (phenyl) sulfan (50.00 g, 166.88 mmol) and 10,10-dimethylanthracene-9 (10 H ) -one (37.10 g, 166.88 mmol) Compound 30-A (52.50 g, 74.02% yield) was obtained by the same method as 19-1 of 19.

Step 30-2) Synthesis of Compound 30

Compound 30-A (20.00 g, 47.06 mmol) obtained in step 30-1 of Example 30 and N -([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9 H Compound 30 (26.20 g, 74.23% yield) was obtained by the same method as Step 19-2, Example 19, using -fluoren-2-amine (17.35 g, 48.00 mmol). (MS [M + H] ⁺ = 750)

Example  31: Synthesis of Compound 31

Step 31-1) Synthesis of Compound 31-A

This example using (2-bromo-6-chlorophenyl) (phenyl) sulfan (50.00 g, 166.88 mmol) and 10,10-dimethylanthracene-9 (10 H ) -one (37.10 g, 166.88 mmol) Compound 31-A (48.20 g, 67.96% yield) was obtained by the same method as 19-1 of 19.

Step 31-2) Synthesis of Compound 31

Using compound 31-A (20.00 g, 47.06 mmol) and di ([1.1'-biphenyl] -4-yl) amine (15.43 g, 48.00 mmol) obtained in step 31-1 of Example 31 above Compound 31 (25.40 g, 76.02% yield) was obtained by the same method as Step 19-2 of Example 19. (MS [M + H] ⁺ = 710)

Example  32: Synthesis of Compound 32

Step 32-1) Synthesis of Compound 32-A

This was carried out using (2-bromo-4-chlorophenyl) (phenyl) sulfan (50.00 g, 166.88 mmol) and 10,10-diphenylanthracene-9 (10 H ) -one (57.81 g, 166.88 mmol) Compound 32-A (60.20 g, 65.69% yield) was obtained by the same method as Step 19-1 of Example 19.

Step 32-2) Synthesis of Compound 32

Example 32 using Compound 32-A (20.00 g, 36.42 mmol) and di ([1.1'-biphenyl] -4-yl) amine (11.94 g, 37.15 mmol) obtained in Step 1 of Example 32. Compound 32 (25.80 g, 84.93% yield) was obtained by the same method as Step 19-2 of 19. (MS [M + H] ⁺ = 834)

Experimental Example  1-1

The glass substrate coated with ITO (Indium Tin Oxide) having a thickness of 1,400 kPa was put in distilled water in which detergent was dissolved and ultrasonically cleaned. In this case, Fischer Co. was used as a detergent, and distilled water was filtered secondly as a filter of Millipore Co. as a distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.

The compound represented by the following formula HAT was thermally vacuum deposited to a thickness of 100 kPa on the prepared ITO transparent electrode to form a hole injection layer. After vacuum depositing a compound represented by the following formula HT1 as a hole transport layer to a thickness of 1150 kPa, the compound 1 prepared in Example 1 was thermally vacuum deposited to a thickness of 150 kPa as an electron blocking layer. Subsequently, the compound represented by the following formula BH and the compound represented by the following formula BD were vapor deposited to a thickness of 200 kPa in a weight ratio of 25: 1 as a light emitting layer. Subsequently, the compound represented by the following formula HB1 was vacuum deposited to a thickness of 50 kV as a hole blocking layer. Subsequently, the compound represented by the following formula ET1 and the compound represented by the following Liq were thermally vacuum deposited to a thickness of 310 kPa in a weight ratio of 1: 1 as the electron transport layer and the electron injection layer. On the electron transporting and electron injection layer, lithium fluoride (LiF) and aluminum were deposited to a thickness of 1000 kW in order to form a cathode, thereby manufacturing an organic light emitting device.

Experimental Example  1-2 to 1-26 and Comparative Experiment  1-1 to 1-5

Except for using the compound shown in Table 1 in place of Compound 1 in Experimental Example 1-1, Experimental Examples 1-2 to 1-26 and Comparative Experimental Example 1-1 in the same manner as in Experimental Example 1-1 To 1-5 to fabricate the organic light emitting device. When a current of 10 mA / cm ² was applied to the organic light emitting diodes manufactured in the Experimental and Comparative Examples, voltage, efficiency, color coordinate, and lifetime were measured, and the results are shown in Table 1 below. On the other hand, T95 refers to the time taken for the luminance to be reduced to 95% from the initial luminance (6000 nit).

 Electronic floor Voltage
(V) efficiency
(cd / A) Color coordinates (x, y) life span
(T ₉₅ , hr) Experimental Example 1-1 Compound 1 3.55 6.33 0.141, 0.044 285 Experimental Example 1-2 Compound 2 3.51 6.23 0.142, 0.045 270 Experimental Example 1-3 Compound 4 3.46 6.32 0.141, 0.044 295 Experimental Example 1-4 Compound 6 3.55 6.17 0.141, 0.044 285 Experimental Example 1-5 Compound 7 3.45 6.28 0.140, 0.044 290 Experimental Example 1-6 Compound 8 3.53 6.12 0.141, 0.044 285 Experimental Example 1-7 Compound 9 3.51 6.13 0.141, 0.044 280 Experimental Example 1-8 Compound 11 3.48 6.18 0.139, 0.044 275 Experimental Example 1-9 Compound 12 3.53 6.19 0.140, 0.043 270 Experimental Example 1-10 Compound 13 3.49 6.25 0.140, 0.044 295 Experimental Example 1-11 Compound 14 3.55 6.17 0.139, 0.043 285 Experimental Example 1-12 Compound 15 3.51 6.18 0.141, 0.043 280 Experimental Example 1-13 Compound 16 3.50 6.16 0.140, 0.045 270 Experimental Example 1-14 Compound 18 3.56 6.09 0.140, 0.043 285 Experimental Example 1-15 Compound 19 3.55 6.19 0.140, 0.043 285 Experimental Example 1-16 Compound 20 3.51 6.11 0.141, 0.043 285 Experimental Example 1-17 Compound 21 3.51 6.16 0.140, 0.044 285 Experimental Example 1-18 Compound 22 3.49 6.09 0.140, 0.044 290 Experimental Example 1-19 Compound 23 3.56 6.17 0.142, 0.043 275 Experimental Example 1-20 Compound 25 3.52 6.23 0.142, 0.045 265 Experimental Example 1-21 Compound 26 3.49 6.24 0.141, 0.045 280 Experimental Example 1-22 Compound 27 3.48 6.18 0.142, 0.044 275 Experimental Example 1-23 Compound 28 3.53 6.18 0.141, 0.044 270 Experimental Example 1-24 Compound 29 3.51 6.20 0.140, 0.043 290 Experimental Example 1-25 Compound 31 3.50 6.14 0.142, 0.045 290 Experimental Example 1-26 Compound 32 3.53 6.12 0.141, 0.044 280 Comparative Experimental Example 1-1 EB1 3.89 5.74 0.143, 0.045 230 Comparative Experimental Example 1-2 EB2 4.01 5.55 0.143, 0.047 210 Comparative Experimental Example 1-3 EB3 4.05 5.49 0.144, 0.048 215 Comparative Experimental Example 1-4 EB4 4.15 5.25 0.143, 0.048 180 Comparative Experimental Example 1-5 EB5 4.10 5.33 0.144, 0.048 160

As shown in Table 1, the compound of the present invention was excellent in electron blocking ability, it was confirmed that the organic light emitting device using this as an electron blocking layer has a significant effect in terms of driving voltage, efficiency, and lifespan.

Experimental Example  2-1 to 2-20 and Comparative example  1-1, 2-1 to 2-4

Except for using the compound represented by the formula EB1 instead of compound 1 as the electron blocking layer in Experimental Example 1-1, and using the compound shown in Table 2 instead of the compound represented by the formula HT1 as the major transport layer, In the same manner as in Experimental Example 1-1, organic light emitting diodes of Experimental Examples 2-1 to 2-20 and Comparative Experimental Examples 2-1 to 2-4 were prepared. When a current of 10 mA / cm ² was applied to the organic light emitting diodes manufactured in the Experimental and Comparative Examples, voltage, efficiency, color coordinate, and lifetime were measured, and the results are shown in Table 1 below. On the other hand, T95 refers to the time taken for the luminance to be reduced to 95% from the initial luminance (6000 nit).

Hole transport layer Voltage
(V) efficiency
(cd / A) Color coordinates (x, y) life span
(T ₉₅ , hr) Experimental Example 2-1 Compound 1 3.55 6.21 0.141, 0.043 295 Experimental Example 2-2 Compound 2 3.52 6.16 0.142, 0.044 275 Experimental Example 2-3 Compound 3 3.54 6.24 0.141, 0.045 280 Experimental Example 2-4 Compound 5 3.56 6.23 0.141, 0.043 270 Experimental Example 2-5 Compound 6 3.53 6.17 0.141, 0.045 285 Experimental Example 2-6 Compound 7 3.51 6.15 0.141, 0.043 270 Experimental Example 2-7 Compound 10 3.51 6.14 0.141, 0.044 285 Experimental Example 2-8 Compound 13 3.52 6.10 0.139, 0.045 275 Experimental Example 2-9 Compound 14 3.51 6.17 0.141, 0.044 285 Experimental Example 2-10 Compound 15 3.54 6.21 0.140, 0.045 295 Experimental Example 2-11 Compound 16 3.56 6.15 0.139, 0.044 280 Experimental Example 2-12 Compound 17 3.51 6.18 0.142, 0.044 270 Experimental Example 2-13 Compound 18 3.60 6.21 0.142, 0.043 275 Experimental Example 2-14 Compound 19 3.60 6.18 0.139, 0.044 280 Experimental Example 2-15 Compound 20 3.54 6.17 0.141, 0.045 275 Experimental Example 2-16 Compound 21 3.55 6.18 0.142, 0.043 285 Experimental Example 2-17 Compound 24 3.51 6.18 0.142, 0.043 275 Experimental Example 2-18 Compound 28 3.63 6.21 0.143, 0.043 280 Experimental Example 2-19 Compound 30 3.62 6.20 0.139, 0.044 280 Experimental Example 2-20 Compound 32 3.58 6.19 0.141, 0.044 275 Comparative Experimental Example 1-1 HT1 3.89 5.74 0.143, 0.045 230 Comparative Experimental Example 2-1 HT2 4.05 5.48 0.143, 0.048 210 Comparative Experimental Example 2-2 HT3 4.06 5.45 0.143, 0.047 215 Comparative Experimental Example 2-3 HT4 4.14 5.24 0.144, 0.048 180 Comparative Experimental Example 2-4 HT5 4.16 5.33 0.144, 0.047 155

As shown in Table 2, the compound of the present invention was excellent in hole transporting ability, it was confirmed that the organic light emitting device using this as a hole transporting layer exhibits significant effects in terms of driving voltage, efficiency, and lifespan.

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

Claims (9)

Compound represented by the following formula (1):
[Formula 1]

In Chemical Formula 1,
X is O, S, Se, P (R ₇ ) or C (R ₇ ) ₂ ,
a, b, c and d are each independently an integer of 1 to 4,
R ₁ to R ₇ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _1-60 haloalkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkoxy; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted C _6-60 aryloxy; Substituted or unsubstituted C _6-60 arylamine; Or C _1-60 heteroaryl including one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S, wherein at least one of R ₃ to R ₆ is represented by the following Chemical Formula 2 Become,
[Formula 2]

In Chemical Formula 2,
L ₁ to L ₃ are each independently a single bond; Substituted or unsubstituted C _6-60 arylene; Or C _1-60 heteroarylene containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted O, N, Si, and S,
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-60 aryl; Or C _1-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted O, N, Si and S.
The method of claim 1,
R ₁ and R ₂ are each independently substituted or unsubstituted C _1-60 alkyl; Or substituted or unsubstituted C _6-60 aryl.
The method of claim 1,
R ₁ and R ₂ are methyl or phenyl.
The method of claim 1,
Formula 1 is any one of the compounds of Formulas 1-1 to 1-4, Compound:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

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

The method of claim 1,
X is O, S, C (CH ₃ ) ₂ or C (C ₆ H ₅ ) ₂ .
The method of claim 1,
Ar ₁ and Ar ₂ are each independently any one selected from the group consisting of:

The method of claim 1,
The compound is any one selected from the group consisting of the following compounds:

A first electrode; A second electrode provided to face the first electrode; And at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers is a compound according to any one of claims 1 to 8. That includes, an organic light emitting device.

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