KR102225488B1 - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

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

Description

Novel compound and organic light emitting device comprising the same

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

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic material. An organic light-emitting device using the organic light-emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.

An organic light-emitting device generally has a structure including an anode and a cathode, and an organic material layer between the anode and the cathode. The organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode 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.

Development of new materials for organic materials used in organic light emitting devices as described above is continuously required.

Korean Patent Publication No. 10-2000-0051826

The present invention relates to a novel organic light-emitting material and an organic light-emitting device including the same.

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

[Formula 1]

In Formula 1,

A is substituted or unsubstituted C _10-60 aryl,

X ₁ , X ₂ and X ₃ are each independently CH or N, provided that at least two of _{X 1,} X ₂ and X _{3 are N,}

Y is O or S,

L is a single bond; Substituted or unsubstituted C _6-60 arylene; _{Or a substituted or unsubstituted C 2-60} heteroarylene including at least one of N, O and S,

Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl including one or more of N, O and S.

In addition, the present invention is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Formula 1 do.

The compound represented by Chemical Formula 1 may be used as a material for an organic material layer of an organic light-emitting device, and may improve efficiency, low driving voltage, and/or lifetime characteristics in the organic light-emitting device. In particular, the compound represented by Formula 1 may be used as a hole injection, hole transport, hole injection, hole suppression and transport, light emission, electron transport, or electron injection material.

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.
2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (3), a hole blocking layer (7), an electron transport layer (8), an electron injection layer (9). And an example of an organic light-emitting device comprising the cathode 4 is shown.

Hereinafter, it will be described in more detail to aid the understanding of 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.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or it means substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing one or more of N, O, and S atoms, or substituted or unsubstituted with two or more substituents connected among the above-exemplified substituents. . For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent to which two phenyl groups are connected.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but 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 C1-C25 linear, branched or cyclic alkyl group or an aryl group having 6 to 25 carbon atoms in the oxygen of 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 it 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 is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

In the present specification, the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.

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 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 are not limited thereto.

In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms 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 an exemplary 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 is preferably 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 10 to 60 carbon atoms. 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 phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the 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,

Can be, etc. However, it is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing at least one of O, N, Si, and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but it is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group 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, acridyl 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, thiiadia There are a zolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.

In the present specification, the aryl group among 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 aforementioned alkyl group. In the present specification, for heteroaryl among heteroarylamines, the description of the aforementioned heterocyclic group may be applied. In the present specification, the alkenyl group of 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 heterocyclic group 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 aryl group or cycloalkyl group described above may be applied except that the hydrocarbon ring is formed by bonding of two substituents. In the present specification, the heterocycle is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied, except that two substituents are bonded to each other and formed.

Preferably, A is biphenylyl, terphenylyl, naphthyl, phenanthrenyl, chrysenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, phenyl-dimethylfluorenyl, spirobifluore Nyl, phenyl-triphenylenyl, naphthyl-phenyl, phenanthrenyl-phenyl, dimethylfluorenyl-phenyl, triphenylenyl-phenyl, or the following substituents:

More preferably, A is biphenylyl, terphenylyl, naphthyl, phenanthrenyl, chrysenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, phenyl-dimethylfluorenyl, spirobiflu Orenyl, naphthyl-phenyl, phenanthrenyl-phenyl, dimethylfluorenyl-phenyl, triphenylenyl-phenyl, or the following substituents:

Most preferably, A is biphenylyl, terphenylyl, naphthyl, phenanthrenyl, chrysenyl, triphenylenyl, 9,9-dimethyl-9H-fluorenyl, 9,9-diphenyl-9H- Fluorenyl, 9,9-dimethyl-2-phenyl-9H-fluorenyl, 9,9'-spirobifluorenyl, naphthyl-phenyl, phenanthrenyl-phenyl, 9,9-dimethyl-9H- Fluorenyl-phenyl, triphenylenyl-phenyl, or the following substituents:

Preferably, X _1, X ₂ and X ₃ may all be N.

Preferably, L is a single bond; Substituted or unsubstituted C _6-20 arylene; _{Or it may be a substituted or unsubstituted C 6-20} heteroarylene including one or more of N, O and S,

More preferably, L may be a single bond, phenylene, biphenylylene, or terphenylylene,

Most preferably, L may be a single bond or phenylene.

Preferably _{, at least one of Ar 1} and Ar ₂ may be a substituted or unsubstituted C _6-60 aryl,

More preferably _{, at least one of Ar 1} and Ar ₂ may be a substituted or unsubstituted C _6-20 aryl.

Preferably, Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-20 aryl; _{Or it may be a substituted or unsubstituted C 6-20} heteroaryl including one or more of N, O and S,

More preferably, Ar ₁ and Ar ₂ may each independently be phenyl, biphenylyl, terphenylyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, or carbazolyl substituted with phenyl,

Most preferably, Ar ₁ and Ar ₂ may each independently be phenyl, biphenylyl, terphenylyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, or 9-phenyl-9H-carbazolyl. have.

Preferably, Formula 1 may be represented by any one of the following Formulas 1-1 to 1-4:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4, A, X ₁ , X ₂ , X ₃ , Y, L, Ar ₁ and Ar ₂ are as defined in Formula 1 above.

Representative examples of the compound represented by Formula 1 are as follows:

The compound represented by Formula 1 may be prepared by the same method as in Scheme 1 below, for example, and other compounds may be prepared similarly.

[Scheme 1]

In Scheme 1, A, X ₁ , X ₂ , X ₃ , Y, L, Ar ₁ and Ar ₂ are as defined in Formula 1, X is halogen, and preferably X is chloro or bromo.

Reaction Scheme 1 is a Suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction may be changed as known in the art. The manufacturing method may be more specific in the manufacturing examples to be described later.

In addition, the present invention provides an organic light-emitting device including the compound represented by Formula 1 above. For example, the present invention provides a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material 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 injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

In addition, the organic material layer may include an emission layer, and the emission layer may include a compound represented by Formula 1 above. In particular, the compound according to the present invention can be used as a host of a light emitting layer.

In addition, the organic material layer may include the electron transport layer, the electron injection layer, or a layer for simultaneously transporting and injecting electrons, and the layer for transporting and injecting electrons at the same time, the electron transport layer, the electron injection layer, It may include a compound represented by Formula 1.

In addition, the organic material layer may include an emission layer and an electron transport layer, and the emission layer may include a compound represented by Formula 1 above.

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 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 inverted type organic light-emitting device 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.

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

2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (3), a hole blocking layer (7), an electron transport layer (8), an electron injection layer (9). And an example of an organic light-emitting device comprising the cathode 4 is shown. In such a structure, the compound represented by Formula 1 may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer, the hole blocking 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 of the organic material layers 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. At this time, using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, the anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate. And, after forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to this 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 material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

In addition to such a method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.

For 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 an anode.

As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode 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); Combinations of metals and oxides such as ZnO:Al or SnO _{2 :Sb;} Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as 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; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer that injects holes from the electrode, and has the ability to transport holes as a hole injection material, so that it has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and is generated from the light emitting layer. A compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent ability to form a thin film is preferable. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, 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.As a hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high mobility for holes This is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

As the light-emitting material, a material capable of emitting light in a visible light 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 for fluorescence or phosphorescence is preferable. Specific examples of 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The emission layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto. Preferably, the compound represented by Formula 1 may be included as a host material.

Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periflanthene and the like having an arylamino group, and the styrylamine compound is substituted or unsubstituted As a compound in which at least one arylvinyl group is substituted on the arylamine, 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, there are styrylamine, styryldiamine, styryltriamine, and styryltetraamine, but are not limited thereto. In addition, examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.

The hole blocking layer is a layer between the electron transport layer and the light emitting layer to prevent holes injected from the anode from being recombined in the light emitting layer and passing to the electron transport layer, and is also referred to as a hole suppressing layer or a hole blocking layer. A material having high ionization energy is preferable for the hole suppression layer.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer.As an electron transport material, a material capable of receiving electrons from the cathode and transferring them to the emission layer is suitable. Do. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq _3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium and samarium, and in each case an aluminum layer or a silver layer follows.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and is excellent in thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. Complex compounds and nitrogen-containing 5-membered ring derivatives, 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-naphtholato)gallium, etc. 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.

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

[Production Example]

Preparation Example 1: Preparation of Compound 1

1) Preparation of Intermediate A1

In a nitrogen atmosphere, 2,7-dichlorobenzothiazole (10.0 g, 49.0 mmol) and [1,1'-biphenyl]-3-ylboronic acid (16.6 g, 51.5 mmol) were added to 100 ml of dioxane, stirred and refluxed. I did. After that, cesium carbonate (31.9 g, 98.0 mmol) was dissolved in 50 ml of water and stirred sufficiently, and then bis(tri- t -butylphosphine)palladium(0)(0.25 g, 0.49 mmol) was added. After the reaction for 5 hours, the temperature was lowered to room temperature and filtered. After the filtrate was extracted with chloroform and water, the organic layer was dried over magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and recrystallized using a mixed solution of chloroform and ethyl acetate. The resulting solid was filtered and dried to prepare an intermediate A1 (11.3 g, yield 72%).

MS: [M+H]+ = 322

2) Preparation of Intermediate A2

Intermediate A1 (11.3 g, 27.3 mmol), bis (pinacolato) diboron (7.6 g, 30.1 mmol) and potassium acetate (8.05 g, 82.0 mmol) were mixed in a nitrogen atmosphere, added to 150 ml of dioxane, and stirred while Heated. In a refluxed state, bis(dibenzylidineacetone)palladium (0.47 g, 0.82 mmol) and tricyclohexylphosphine (0.46 g, 1.6 mmol) were added, followed by heating and stirring for 6 hours. After the reaction was completed, the temperature was lowered to room temperature and then filtered. Water was poured into the filtrate, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure and recrystallized with ethyl acetate, intermediate A2 (8.7 g, yield 77%) was prepared.

MS: [M+H]+ = 414

3) Preparation of compound 1

In a 250 mL round bottom flask in a nitrogen atmosphere, intermediate A2 (8.7 g, 21.0 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5 -After dissolving triazine (7.23 g, 21.0 mmol) in 100 mL of tetrahydrofuran, 1.5 M aqueous potassium carbonate solution (65 mL) was added, and bis (tri- t -butylphosphine) palladium (0) (0.11 g, 0.2 mmol) was added, followed by heating and stirring for 7 hours. The temperature was lowered to room temperature, the water layer was separated and removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized using tetrahydrofuran and ethyl acetate, and dried to prepare Compound 1 (7.1 g, yield 57%).

MS: [M+H] ⁺ = 595

Preparation Example 2: Preparation of Compound 2

1) Preparation of intermediate A3

[1,1'-biphenyl]-3-ylboronic acid, except that (9,9-dimethyl-9H-fluoren-2-yl) boronic acid was used in the same manner as in the method of preparing Intermediate A1, the intermediate A3 (12.6 g, yield 71%) was prepared

MS: [M+H] ⁺ = 362

2) Preparation of Intermediate A4

The intermediate A4 (11.7 g, yield 74%) was prepared in the same manner as the method of preparing the intermediate A2 except for using the intermediate A3 instead of the intermediate A1.

MS: [M+H] ⁺ = 454

3) Preparation of compound 2

Intermediate A2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of Intermediate A4 and 2-(4-bromophenyl) Compound 2 (10.5 g, yield 64%) was prepared in the same manner as in the method of preparing compound 1, except that -4,6-diphenyl-1,3,5-triazine was used.

MS: [M+H] ⁺ = 635

Preparation Example 3: Preparation of compound 3

1) Preparation of Intermediate A5

Intermediate A5 (13.0 g, yield 77%) was prepared in the same manner as in the method of preparing Intermediate A1, except that phenanthrene-3-ylboronic acid was used instead of [1,1′-biphenyl]-3-ylboronic acid. I did.

MS: [M+H] ⁺ = 346

2) Preparation of Intermediate A6

The intermediate A6 (13.6 g, yield 83%) was prepared in the same manner as the method of preparing intermediate A2, except that intermediate A5 was used instead of intermediate A1.

MS: [M+H] ⁺ = 438

3) Preparation of compound 3

Intermediate A2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of intermediate A6 and 9-(4-chloro-6- Compound 3 (12.7 g, yield 65%) was prepared in the same manner as in the method of preparing compound 1, except that phenyl-1,3,5-triazine-2-yl)-9H-carbazole was used.

MS: [M+H] ⁺ = 632

Preparation Example 4: Preparation of compound 4

1) Preparation of intermediate B1

Instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl]-3-ylboronic acid, instead of 2,7-dichlorobenzoxazole and [1,1':4',1"-terphenyl]- Intermediate B1 (13.1 g, yield 65%) was prepared in the same manner as in the method of preparing Intermediate A1 except that 3-ylboronic acid was used.

MS: [M+H] ⁺ = 275

2) Preparation of intermediate B2

The intermediate B2 (10.6 g, yield 65%) was prepared in the same manner as the method of preparing the intermediate A2 except for using the intermediate B1 instead of the intermediate A1.

MS: [M+H] ⁺ = 382

3) Preparation of compound 4

Intermediate A2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of intermediate B2 and 2-chloro-4- (dibenzo Compound 4 (9.9 g, yield 66%) was prepared in the same manner as in the method of preparing compound 1 except that furan-4-yl)-6-phenyl-1,3,5-triazine was used.

MS: [M+H] ⁺ = 669

Preparation Example 5: Preparation of compound 5

1) Preparation of intermediate B3

Method for preparing intermediate A1 except that 2,7-dichlorobenzooxazole and naphthalene-1ylboronic acid were used instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl]-3-ylboronic acid, and The intermediate B3 (11.6 g, yield 78%) was prepared in the same manner.

MS: [M+H] ⁺ = 280

2) Preparation of intermediate B4

Intermediate B4 (9.7 g, yield 77%) was prepared in the same manner as the method of preparing Intermediate A2, except that Intermediate B3 was used instead of Intermediate A1.

MS: [M+H] ⁺ = 372

3) Preparation of compound 5

Intermediate A2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of intermediate B4 and 2-(4-chlorophenyl)- Compound 5 (10.0 g, yield 59%) by the same method as the method of preparing compound 1, except that 4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine was used. Was prepared.

MS: [M+H] ⁺ = 643

Preparation Example 6: Preparation of compound 6

1) Preparation of intermediate C1

Using 2,6-dichlorobenzothiazole and [1,1'-biphenyl]-4-ylboronic acid instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl]-3-ylboronic acid The intermediate C1 (10.9 g, yield 69%) was prepared in the same manner as the method for preparing intermediate A1 except.

MS: [M+H] ⁺ = 322

2) Preparation of intermediate C2

The intermediate C2 (10.5 g, yield 75%) was prepared in the same manner as the method of preparing the intermediate A2 except for using the intermediate C1 instead of the intermediate A1.

MS: [M+H] ⁺ = 414

3) Preparation of compound 6

Intermediate A2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of intermediate C2 and (4-chloro-6-phenyl- Compound 6 (10.7 g, yield 62%) was prepared in the same manner as in the method of preparing compound 1, except that 1,3,5-triazine-2yl)-9-phenyl-9H-carbazole was used. .

MS: [M+H] ⁺ = 684

Preparation Example 7: Preparation of compound 7

1) Preparation of intermediate C3

Instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl]-3-ylboronic acid, instead of 2,6-dichlorobenzothiazole and [1,1':4',1"-terphenyl]- Intermediate C3 (13.6 g, yield 70%) was prepared in the same manner as in the method of preparing Intermediate A1 except that 4-ylboronic acid was used.

MS: [M+H] ⁺ = 398

2) Preparation of intermediate C4

Intermediate C4 (12.7 g, yield 76%) was prepared in the same manner as the method of preparing Intermediate A2, except that Intermediate C2 was used instead of Intermediate A1.

MS: [M+H] ⁺ =490

3) Preparation of compound 7

Intermediate C4 and 2-chloro-4 (dibenzofuran instead of intermediate A2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine -1 day) -Compound 7 (12.9 g, yield 73%) was prepared in the same manner as in the method of preparing compound 1, except that -6-phenyl-1,3,5-triazine was used.

MS: [M+H] ⁺ = 685

Preparation Example 8: Preparation of compound 8

1) Preparation of intermediate C5

Method for preparing intermediate A1 except that 2,6-dichlorobenzothiazole and phenanthrene-3ylboronic acid were used instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl]-3-ylboronic acid The intermediate C5 (12.4 g, yield 73%) was prepared in the same manner as described above.

MS: [M+H] ⁺ = 346

2) Preparation of intermediate C6

Intermediate C6 (11.5 g, yield 73%) was prepared in the same manner as in the method of preparing Intermediate A2, except that Intermediate C5 was used instead of Intermediate A1.

MS: [M+H] ⁺ =438

3) Preparation of compound 8

Intermediate A2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of intermediate C6 and 9-(4-(4-chloro) Phenyl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole was used in the same manner as the method of preparing compound 1, except that compound 8 (13.0 g, yield 70%) ) Was prepared.

MS: [M+H] ⁺ = 708

Preparation Example 9: Preparation of compound 9

1) Preparation of intermediate D1

Instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl]-3-ylboronic acid, 2,6-dichlorobenzoxazole and (4-(9,9-dimethyl-9H-fluorene-2- Intermediate D1 (12.9 g, yield 58%) was prepared in the same manner as in the method of preparing Intermediate A1 except that 1) phenyl) boronic acid was used.

MS: [M+H] ⁺ = 422

2) Preparation of intermediate D2

The intermediate D2 (9.9 g, yield 63%) was prepared in the same manner as the method of preparing the intermediate A2 except for using the intermediate D1 instead of the intermediate A1.

MS: [M+H] ⁺ =514

3) Preparation of compound 9

Intermediate A2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of intermediate D2 and 2-chloro-4- (dibenzo Compound 9 (9.2 g, yield 67%) was prepared in the same manner as in the method of preparing compound 1, except that furan-3-yl)-6-phenyl-1,3,5-triazine was used.

MS: [M+H] ⁺ = 709

Preparation Example 10: Preparation of Compound 10

1) Preparation of intermediate D3

2,6-dichlorobenzoxazole and (3-(triphenylen-2-yl)phenyl)boronic acid instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl]-3-ylboronic acid The intermediate D3 (15.0 g, yield 62%) was prepared in the same manner as in the method of preparing Intermediate A1, except that it was used.

MS: [M+H] ⁺ = 456

2) Preparation of intermediate D4

The intermediate D4 (11.8 g, yield 65%) was prepared in the same manner as the method of preparing the intermediate A2 except for using the intermediate D3 instead of the intermediate A1.

MS: [M+H] ⁺ =548

3) Preparation of compound 10

Intermediate D2 and 2-chloro-4,6-phenyl instead of intermediate A2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine Compound 10 (10.0 g, yield 71%) was prepared in the same manner as in the method of preparing compound 1, except that -1,3,5-triazine was used.

MS: [M+H] ⁺ = 653

Preparation Example 11: Preparation of compound 11

1) Preparation of Intermediate E1

Intermediate E1 (12.0 g, yield 76%) was prepared in the same manner as in the method of preparing Intermediate A1, except that 2,5-dichlorobenzothiazole was used instead of 2,7-dichlorobenzothiazole.

MS: [M+H] ⁺ = 322

2) Preparation of Intermediate E2

The intermediate E2 (9.8 g, yield 63%) was prepared in the same manner as the method of preparing the intermediate A2 except for using the intermediate E1 instead of the intermediate A1.

MS: [M+H] ⁺ =414

3) Preparation of compound 11

Intermediate A2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of intermediate E2 and 2-([1,1'- Biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine was used in the same manner as in the preparation of compound 1, except that compound 11 (9.5 g, yield 67%) ) Was prepared.

MS: [M+H] ⁺ = 595

Preparation Example 12: Preparation of compound 12

1) Preparation of Intermediate E3

To prepare Intermediate A1 except that 2,5-dichlorobenzothiazole and phenanthrene-9-ylboronic acid were used instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl]-3-ylboronic acid. The intermediate E3 (11.7 g, yield 69%) was prepared in the same manner as in the method.

MS: [M+H] ⁺ = 346

2) Preparation of Intermediate E4

The intermediate E4 (11.0 g, yield 74%) was prepared in the same manner as the method of preparing the intermediate A2 except for using the intermediate E3 instead of the intermediate A1.

MS: [M+H] ⁺ =438

3) Preparation of compound 12

Intermediate A2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of intermediate E4 and 2-chloro-4- (dibenzo Compound 12 (10.6 g, yield 67%) was prepared in the same manner as in the method of preparing compound 1, except that furan-4-yl)-6-phenyl-1,3,5-triazine was used.

MS: [M+H] ⁺ = 633

Preparation Example 13: Preparation of compound 13

1) Preparation of Intermediate E5

Instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl]-3-ylboronic acid, instead of 2,5-dichlorobenzothiazole and (9,9-diphenyl-9H-fluoren-2-yl) Intermediate E5 (14.7 g, yield 59%) was prepared in the same manner as in the method of preparing Intermediate A1 except that boronic acid was used.

MS: [M+H] ⁺ = 486

2) Preparation of Intermediate E6

Intermediate E6 (11.9 g, yield 71%) was prepared in the same manner as in the method of preparing Intermediate A2, except that Intermediate E5 was used instead of Intermediate A1.

MS: [M+H] ⁺ =578

3) Preparation of compound 13

Intermediate E6 and 4-(4-chloro-6- instead of Intermediate A2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine Except for using phenyl-1,3,5-triazine-2-yl)-9-phenyl-9H-carbazole, compound 13 (11.2 g, yield 64%) in the same manner as the method of preparing compound 1 Was prepared.

MS: [M+H] ⁺ = 848

Preparation Example 14: Preparation of compound 14

1) Preparation of intermediate F1

Using 2,5-dichlorobenzoxazole and [1,1'-biphenyl]-4-ylboronic acid instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl]-3-ylboronic acid The intermediate F1 (10.4 g, yield 62%) was prepared in the same manner as the method for preparing intermediate A1 except.

MS: [M+H] ⁺ = 306

2) Preparation of intermediate F2

The intermediate F2 (8.9 g, yield 68%) was prepared in the same manner as the method of preparing the intermediate A2 except for using the intermediate F1 instead of the intermediate A1.

MS: [M+H] ⁺ =398

3) Preparation of compound 14

Intermediate A2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of intermediate F2 and 9-(4-(3-chloro) Phenyl)-6-phenyl-1,3,5-triazine-2-yl) -9H- Except for the use of carbazole, the compound 14 (9.5 g, yield 64%) in the same manner as the method of preparing compound 1 ) Was prepared.

MS: [M+H] ⁺ = 668

Preparation Example 15: Preparation of compound 15

1) Preparation of intermediate F3

Instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl]-3-ylboronic acid, instead of 2,5-dichlorobenzooxazole and [1,1':3',1"-terphenyl]- Intermediate F3 (12.3 g, yield 61%) was prepared in the same manner as in the method of preparing Intermediate A1, except that 5'-ylboronic acid was used.

MS: [M+H] ⁺ = 382

2) Preparation of intermediate F4

The intermediate F4 (10.8 g, 71%) was prepared in the same manner as the method of preparing the intermediate A2, except that intermediate F3 was used instead of the intermediate A1.

MS: [M+H] ⁺ =474

3) Preparation of compound 15

Intermediate A2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of intermediate F4 and 2-chloro-4- (dibenzo Compound 15 (10.6 g, yield 68%) was prepared in the same manner as in the method of preparing compound 1, except that thiophen-4-yl)-6-phenyl-1,3,5-triazine was used.

MS: [M+H] ⁺ = 685

Preparation Example 16: Preparation of compound 16

1) Preparation of intermediate G1

Method for preparing intermediate A1 except for using 2,4-dichlorothiazole and naphthalen-1-ylboronic acid instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl]-3-ylboronic acid, and The intermediate G1 (8.9 g, yield 62%) was prepared in the same manner.

MS: [M+H] ⁺ = 296

2) Preparation of intermediate G2

The intermediate G2 (8.1 g, yield 70%) was prepared in the same manner as the method of preparing intermediate A2, except that intermediate G1 was used instead of intermediate A1.

MS: [M+H] ⁺ =388

3) Preparation of compound 16

Intermediate A2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of intermediate G2 and 2-chloro-4- (dibenzo Compound 16 (8.6 g, yield 71%) was prepared in the same manner as in the method of preparing compound 1, except that furan-2-yl)-6-phenyl-1,3,5-triazine was used.

MS: [M+H] ⁺ =583

Preparation Example 17: Preparation of compound 17

1) Preparation of intermediate G3

2,4-dichlorothiazole and [1,1':4',1''-terphenyl]-3 instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl]-3-ylboronic acid -Intermediate G3 (12.6 g, yield 65%) was prepared in the same manner as in the method of preparing Intermediate A1 except that ilboronic acid was used.

MS: [M+H] ⁺ = 398

2) Preparation of intermediate G4

The intermediate G4 (10.9 g, yield 70%) was prepared in the same manner as the method of preparing intermediate A2, except that intermediate G3 was used instead of intermediate A1.

MS: [M+H] ⁺ =490

3) Preparation of compound 17

Intermediate A2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of intermediate G4 and 2-(3-chlorophenyl)- 4-(dibenzothiophen-4-yl)-6-phenyl-1,3,5-triazine was used in the same manner as for preparing compound 1, except that compound 17 (12.1 g, yield 70%) ) Was prepared.

MS: [M+H] ⁺ =777

Preparation Example 18: Preparation of compound 18

1) Preparation of intermediate G5

2,4-dichlorothiazole and (9,9-dimethyl-9H-fluoren-2-yl) boronic acid instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl]-3-ylboronic acid The intermediate G5 (10.8 g, yield 61%) was prepared in the same manner as the method of preparing Intermediate A1 except for using.

MS: [M+H] ⁺ = 362

2) Preparation of intermediate G6

The intermediate G4 (8.6 g, 63%) was prepared in the same manner as the method of preparing the intermediate A2, except that the intermediate G3 was used instead of the intermediate A1.

MS: [M+H] ⁺ =454

3) Preparation of compound 18

Intermediate G6 and 2-chloro-4,6-phenyl instead of Intermediate A2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine Compound 18 (7.2 g, yield 68%) was prepared in the same manner as in the method of preparing compound 1, except that -1,3,5-triazine was used.

MS: [M+H] ⁺ =559

Preparation Example 19: Preparation of compound 19

1) Preparation of intermediate H1

2,4-dichlorooxazole and [1,1':3',1''-terphenyl]-5 instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl]-3-ylboronic acid Intermediate H1 (12.8 g, yield 63%) was prepared in the same manner as in the method of preparing Intermediate A1 except that'-ilboronic acid was used.

MS: [M+H] ⁺ = 382

2) Preparation of intermediate H2

The intermediate H2 (11.2 g, yield 70%) was prepared in the same manner as the method of preparing intermediate A2, except that intermediate H1 was used instead of intermediate A1.

MS: [M+H] ⁺ =474

3) Preparation of compound 19

Intermediate A2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of intermediate H2 and 2-(4-chlorophenyl)- Compound 19 (12.6 g, yield 69%) by the same method as the method of preparing compound 1 except for using 4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine Was prepared.

MS: [M+H] ⁺ =745

Preparation Example 20: Preparation of compound 20

1) Preparation of intermediate H3

To prepare Intermediate A1 except that 2,4-dichlorooxazole and triphenylene-2-ylboronic acid were used instead of 2,7-dichlorobenzothiazole and [1,1'-biphenyl]-3-ylboronic acid. The intermediate H3 (14.0 g, yield 69%) was prepared in the same manner as in the method.

MS: [M+H] ⁺ = 380

2) Preparation of intermediate H4

The intermediate H4 (13.1 g, yield 75%) was prepared in the same manner as the method of preparing the intermediate A2 except for using the intermediate H3 instead of the intermediate A1.

MS: [M+H] ⁺ =472

3) Preparation of compound 20

Intermediate A2 and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine instead of intermediate H4 and 2-(3-bromophenyl) Compound 20 (12.7 g, yield 70%) was prepared in the same manner as in the method of preparing compound 1, except that -4,6-diphenyl-1,3,5-triazine was used.

MS: [M+H] ⁺ =653

[Example]

Example 1

A glass substrate coated with a thin film of ITO (Indium Tin Oxide) to a thickness of 1,300 Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

The following compound HI-A was thermally vacuum deposited to a thickness of 100 Å on the prepared ITO transparent electrode to form a hole injection layer. Subsequently, only the compound HT-A was thermally vacuum deposited to a thickness of 800 Å, and the compound HT-B was sequentially vacuum deposited to a thickness of 500 Å to form a hole transport layer. Subsequently, the light emitting layer was vacuum-deposited with Compound 1 prepared above and Compound H1 below in a weight ratio of 50:50, and Compound GD of 6% by weight of the sum of the weights of the two hosts to a thickness of 350 Å. Subsequently, the following compound ET-A was vacuum-deposited to a thickness of 50 Å as a hole blocking layer. Subsequently, as an electron transport and injection layer, the following compounds ET-B and Liq were thermally vacuum deposited to a thickness of 250 Å at a ratio of 1:1, and then LiF was vacuum deposited to a thickness of 30 Å. An organic light emitting device was manufactured by depositing aluminum to a thickness of 1000 Å on the electron injection layer to form a cathode.

Examples 2 to 16

Organic light-emitting devices of Examples 2 to 16 were manufactured using the same method as in Example 1, except that the host material was changed as shown in Table 1 below.

Comparative Examples 1 to 3

Organic light-emitting devices of Comparative Examples 1 to 3 were manufactured using the same method as in Example 1, except that the host material was changed as shown in Table 1 below. Compounds C1 to C3 in Table 1 are as follows.

[Experimental Example]

By applying a current to the organic light emitting device prepared in Examples 1 to 16 and Comparative Examples 1 to 3, voltage, efficiency, and lifetime (T95) were measured, and the results are shown in Table 1 below. At this time, the voltage and efficiency were ^{measured by applying a current density of 10 mA/cm 2} , and T95 refers to the time from the current density of 50 mA/cm ² until the initial luminance decreases to 95%.

Host material @ 10mA / cm ² @ 50mA / cm ² Voltage(V) Efficiency (cd/A) Life (T95, hr) Example 1 Compound 1 4.2 63.5 90 Example 2 Compound 2 4.1 62.4 88 Example 3 Compound 3 4.3 63.0 105 Example 4 Compound 4 4.2 62.9 95 Example 5 Compound 6 4.2 62.6 93 Example 6 Compound 7 4.3 62.8 85 Example 7 Compound 9 4.1 64.0 80 Example 8 Compound 10 4.2 63.7 82 Example 9 Compound 11 4.2 63.9 91 Example 10 Compound 13 4.2 63.0 80 Example 11 Compound 14 4.2 62.8 81 Example 12 Compound 15 4.2 63.4 80 Example 13 Compound 17 4.1 63.6 86 Example 14 Compound 18 4.2 63.0 90 Example 15 Compound 19 4.2 62.5 92 Example 16 Compound 20 4.2 62.6 85 Comparative Example 1 Compound C1 4.2 55 55 Comparative Example 2 Compound C2 4.9 50.6 25 Comparative Example 3 Compound C3 5.4 20.4 20

As shown in Table 1, it can be seen that the organic light-emitting device manufactured by using the compound according to the present invention as a host of the emission layer exhibits superior performance in terms of efficiency and lifetime compared to the organic light-emitting device of Comparative Example.

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

Claims (8)

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

In Formula 1,
A is substituted or unsubstituted C _10-60 aryl,
X ₁ , X ₂ and X ₃ are each independently CH or N, provided that at least two of _{X 1,} X ₂ and X _{3 are N,}
Y is O or S,
L is a single bond; Substituted or unsubstituted C _6-60 arylene; _{Or a substituted or unsubstituted C 2-60} heteroarylene including at least one of N, O and S,
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl including one or more of N, O and S.
The method of claim 1,
A is biphenylyl, terphenylyl, naphthyl, phenanthrenyl, chrysenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, phenyl-dimethylfluorenyl, spirobifluorenyl, phenyl- Triphenylenyl, naphthyl-phenyl, phenanthrenyl-phenyl, dimethylfluorenyl-phenyl, triphenylenyl-phenyl, or the following substituents,
compound:

.
The method of claim 1,
X _1, X ₂ and X ₃ are all N,
compound.
The method of claim 1,
L is a single bond, phenylene, biphenylylene, or terphenylylene,
compound.
The method of claim 1,
At least one of Ar ₁ and Ar ₂ is substituted or unsubstituted C _6-60 aryl,
compound.
The method of claim 1,
Ar ₁ and Ar ₂ are each independently phenyl, biphenylyl, terphenylyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, or carbazolyl substituted with phenyl,
compound.
The method of claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of the following,
compound:

. A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound according to any one of claims 1 to 7 To do,
Organic light emitting device.

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