WO2020235955A1 - Novel compound and organic light-emitting device using same - Google Patents

Abstract

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

Description

Novel compound and organic light emitting device using the same

Cross-reference with related application(s)

This application claims the benefit of priority based on Korean Patent Application No. 10-2019-0060196 filed May 22, 2019 and Korean Patent Application No. 10-2020-0061052 filed May 21, 2020. All contents disclosed in the literature are included as part of this specification.

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

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy 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.

The 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. It glows when it falls back to the ground.

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

Prior art literature

Patent Literature

(Patent Document 0001) Korean Patent Publication No. 10-2013-073537

The present invention relates to an organic light-emitting device comprising the novel compound.

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

Compound represented by the following formula (1):

[Formula 1]

In Formula 1,

X ₁ , X ₂ , and X ₃ are each independently N or CH, provided that at least one of X ₁ , X ₂ and X ₃ is N,

L is a direct bond, a substituted or unsubstituted C _6-60 arylene, or a substituted or unsubstituted C _5-60 heteroarylene containing at least one hetero atom selected from the group consisting of N, O and S ,

Ra is substituted or unsubstituted C _6-60 aryl,

Rb is any one selected from compounds represented by the following,

Each R ₁ is independently hydrogen, deuterium, or substituted or unsubstituted C _6-60 aryl,

R ₂ is substituted or unsubstituted C _6-60 aryl,

p is an integer from 0 to 5,

n is each independently an integer of 1 to 7,

m is an integer of 1 to 8.

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 comprises the compound of the present invention.

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 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), an electron suppression layer (7), a light emitting layer (3), an electron transport layer (8), an electron injection layer (9). And an example of an organic light-emitting device including the cathode 4 is shown.

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

(Explanation of terms)

In this specification,

Means a bond connected to another substituent.

In the present specification, the term "substituted or unsubstituted" refers to deuterium (D); 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 a substituted or unsubstituted 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 linked with two or more substituents 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 it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with an oxygen of the ester group with a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. 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, and a phenyl boron group, 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 a linear or branched chain, 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, cycloheptylmethyl, 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 is preferably 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 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.

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,

Etc. However, it is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group including at least one of O, N, Si and S as a heterogeneous element, and the number of carbons 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, thiazolyl group, isoxazolyl Group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, 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 the 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 above-described heterocyclic group may be applied, except that two substituents are bonded to each other.

(compound)

The present invention provides a compound represented by Formula 1:

[Formula 1]

In Formula 1, an aryl group (Ra) is substituted at position 2 of the dibenzothiophene core, and a triazine-based substituent at position 6 (

) Is substituted, and all carbons of C ₁ , C ₃ , C ₄ , C ₇ , C ₈ , C ₉ , which are other positions of the core, are replaced with hydrogen.

In Formula 1, D means deuterium.

X ₁ , X ₂ , and X ₃ are each independently N or CH, provided that at least one of X ₁ , X ₂ and X ₃ is N,

L is a direct bond, a substituted or unsubstituted C _6-60 arylene, or a substituted or unsubstituted C _5-60 heteroarylene containing at least one hetero atom selected from the group consisting of N, O and S ,

Ra is substituted or unsubstituted C _6-60 aryl,

Rb is any one selected from compounds represented by the following,

Each R ₁ is independently hydrogen, deuterium, or substituted or unsubstituted C _6-60 aryl,

R ₂ is substituted or unsubstituted C _6-60 aryl,

p is an integer from 0 to 5,

n is each independently an integer of 1 to 7,

m is an integer of 1 to 8.

Preferably, L is a direct bond, or phenylene.

Preferably, Ra is phenyl, biphenylyl, terphenylyl, dimethylfluorenyl, naphthyl, phenanthrenyl or triphenylenyl, which are unsubstituted or substituted with one or more deuterium. On the other hand, when deuterium is further substituted at the terminal, lifespan characteristics are improved when applied to an organic light emitting device, which is preferable.

Preferably, each R ₁ is independently hydrogen, deuterium, or phenyl unsubstituted or substituted with one or more deuterium. On the other hand, when deuterium is further substituted at the terminal, lifespan characteristics are improved when applied to an organic light emitting device, which is preferable.

Preferably, R ₂ is phenyl.

Preferably, n is an integer from 1 to 6.

Preferably, m is an integer from 1 to 6.

Preferably, the compound represented by Formula 1 may be any one selected from the group consisting of:

.

The compound represented by Formula 1 according to the present invention is a compound containing an aryl group at position 2 and a triazine substituent at position 6 of dibenzothiophene. In particular, the triazine substituent group is dibenzofuran and dibenzothiophene. By including an additional substituent of any one of, carbazole, electron injection and electron transfer speed can be improved, and accordingly, the organic light emitting device employing the compound of the present invention exhibits high efficiency, low driving voltage, and high luminance. , It has excellent long life characteristics. In particular, when the triazine-based substituent is dibenzofuran or dibenzothiophene, it is possible to remarkably improve the lifespan characteristics even if no additional substituent is included.

The compound represented by Formula 1 can be prepared through the following Scheme A.

[Scheme A]

In Reaction Scheme A, Z _1, and the remaining variables except for the Z ₂ are as defined above, Z ₁ and Z ₂ are each independently halogen, preferably chloro or bromo.

In Reaction Scheme A, the reactants, catalysts, solvents, and the like to be used can be changed to suit the desired product. The method for preparing the compound of Formula 1 may be more specific in Preparation Examples to be described later.

(Organic light emitting device)

The present invention provides an organic light-emitting device including the compound represented by Chemical Formula 1. 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, an electron suppression 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 a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes is represented by Formula 1 above. Including the indicated compound.

In addition, the organic material layer may include an electron suppressing layer, and the electron suppressing layer includes the compound represented by Formula 1 above.

In addition, the organic material layer may include an emission layer, and the emission layer includes the compound represented by Chemical Formula 1. Preferably, the compound represented by Formula 1 may be included as a host of the emission layer. In addition, the emission layer may further include a dopant compound.

In addition, the organic material layer may include an electron transport layer, an electron injection layer, or a layer for simultaneous electron transport and electron injection, and the electron transport layer, an electron injection layer, or a layer for simultaneous electron transport and electron injection is represented by the formula It includes the compound represented by 1.

In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) 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), an electron suppression layer (7), a light emitting layer (3), an electron transport layer (8), an electron injection layer (9). And an example of an organic light-emitting device including 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 electron suppression layer, the light-emitting layer, the electron transport layer, and the electron injection 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 an 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 a light emitting layer or a light emitting material. 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.

The electron-suppression layer is a layer between the hole-transport layer and the light-emitting layer in order to prevent electrons injected from the cathode from passing over to the hole-transport layer without being recombined in the light-emitting layer, and is also called an electron-blocking layer. The electron-suppressing layer is preferably a material having less electron affinity than the electron transport layer.

As the light-emitting material, a material capable of emitting light in a 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 against fluorescence or phosphorescence is preferable. Specific examples of 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-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.

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, and periflanthene 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 an aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

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 on 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 has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, 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.

Preparation of the compound represented by 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 for illustrating the present invention, and the scope of the present invention is not limited thereto.

[Production Example 1]

Preparation Example 1-1: Synthesis of the compound of Intermediate 1a

(A) Preparation of intermediate 1a

In a nitrogen atmosphere, add 4-chlorodibenzothiophene (100 g, 0.45 mol) and 300 ml of acetic acid to a 1000 ml round bottom flask, and slowly add bromine (73.1 g, 0.47 mol) at low temperature using a dropping funnel. And stirred at room temperature for 15 hours. After that, the solid obtained by the filter was dissolved in tetrahydrofuran, washed with water and sodium thiosulfate solution, and the organic layer was separated and recrystallized using ethanol to obtain intermediate 1a (85 g, yield 62%, MS:[ M+H] ⁺ = 296).

Preparation Example 1-2: Synthesis of the compound of Intermediate 2a-2

1) Preparation of compound 2a-1

In a nitrogen atmosphere, 1a (30 g, 100.8 mmol) and phenylboronic acid (12.3 g, 100.8 mmol) were added to 600 ml of tetrahydrofuran, followed by stirring and refluxing. Thereafter, potassium carbonate (41.8 g, 302.4 mmol) was dissolved in 42 ml of water, and after sufficiently stirring, tetrakistriphenyl-phosphinopalladium (3.5 g, 3 mmol) was added. After reacting for 8 hours, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 594 mL of chloroform, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound 2a-1 (25.6g, 86%, MS: [M+H]+ = 295.8).

2) Preparation of compound 2a-2

In a nitrogen atmosphere, 2a-1 (25.6 g, 86.8 mmol) and bis (pinacolato) diboron (33.1 g, 130.3 mmol) were added to 512 ml of Diox, followed by stirring and refluxing. Thereafter, potassium acetate (25 g, 260.5 mmol) was added and sufficiently stirred, and then palladium dibenzylidene acetone palladium (1.5 g, 2.6 mmol) and tricyclohexylphosphine (1.5 g, 5.2 mmol) were added. After reaction for 7 hours, the organic layer was allowed to cool to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 335 mL of chloroform to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to prepare an ivory solid compound 2a-2 (26.8g, 80%, MS: [M+H]+ = 387.3).

Preparation Example 1-3: Synthesis of the compound of Intermediate 3a-2

1) Preparation of compound 3a-1

The same method as the method of preparing compound 2a-1 of Preparation Example 1-2, except that [1,1'-biphenyl]-4-yl boronic acid (10 g, 50.4 mmol) was used instead of phenylboronic acid. To prepare compound 3a-1 (16.4 g, yield 88%; MS:[M+H] ⁺ =371).

2) Preparation of compound 3a-2

Compound 3a-2 (16.4 g, yield 80%; MS:[M+) in the same manner as the method of preparing compound 2a-1, except that compound 3a-1 (16.4g, 44.3 mmol) was used instead of compound 2a-1. H] ⁺ =463) was prepared.

Preparation Example 1-4: Synthesis of the compound of Intermediate 4a-2

1) Preparation of compound 4a-1

The same method as the method of preparing compound 2a-1 of Preparation Example 1-2, except that [1,1'-biphenyl]-3-yl boronic acid (13.7 g, 50.4 mmol) was used instead of phenylboronic acid. To prepare compound 4a-1 (14.7 g, yield 72%; MS:[M+H] ⁺ =371).

2) Preparation of compound 4a-2

Compound 4a-2 (14.5 g, yield 79%; MS:[M+) in the same manner as the method of preparing compound 2a-1, except that compound 4a-1 (14.7g, 39.7 mmol) was used instead of compound 2a-1. H] ⁺ =463) was prepared.

Preparation Example 1-5: Synthesis of the compound of Intermediate 5a-2

1) Preparation of compound 5a-1

Compound 2a- of Preparation Example 1-2, except that [1,1':3',1"-terphenyl]-5'-yl boronic acid (13.8 g, 50.4 mmol) was used instead of phenylboronic acid. Compound 5a-1 (18.7 g, yield 83%; MS:[M+H] ⁺ =448) was prepared in the same manner as in the method of preparing 1.

2) Preparation of compound 5a-2

Compound 5a-2 (17.8 g, yield 79%; MS:[M+) in the same manner as the method of preparing compound 2a-1, except that compound 5a-1 (18.7g, 41.8 mmol) was used instead of compound 2a-1. H] ⁺ =539) was prepared.

Preparation Example 1-6: Synthesis of the compound of Intermediate 6a-2

1) Preparation of compound 6a-1

A method for preparing compound 2a-1 of Preparation Example 1-2, except that (9,9-dimethyl-9H-fluoren-2-yl) boronic acid (12.0 g, 50.4 mmol) was used instead of phenylboronic acid Compound 6a-1 (15.5 g, yield 75%; MS:[M+H] ⁺ =411) was prepared in the same manner as described above.

2) Preparation of compound 6a-2

Compound 6a-2 (14.4 g, yield 76%; MS:[M+) in the same manner as the method of preparing compound 2a-1, except that compound 6a-1 (15.5g, 87.8 mmol) was used instead of compound 2a-1. H] ⁺ =503) was prepared.

Preparation Example 1-7: Synthesis of the compound of Intermediate 7a-2

1) Preparation of compound 7a-1

Except for using naphthalen-1-yl boronic acid (6.9 g, 40.3 mmol) instead of phenylboronic acid, compound 7a-1 (10.0 g) in the same manner as the method of preparing compound 2a-1 of Preparation Example 1-2 , Yield 72%; MS:[M+H] ⁺ =345) was prepared.

2) Preparation of compound 7a-2

Compound 7a-2 (9.5 g, yield 75%; MS:[M+) in the same manner as the method of preparing compound 2a-1, except that compound 7a-1 (10.0g, 29.1 mmol) was used instead of compound 2a-1 H] ⁺ =437.2) was prepared.

Preparation Example 1-8: Synthesis of the compound of Intermediate 8a-2

1) Preparation of compound 8a-1

Except for using phenanthren-2-yl boronic acid (9.0 g, 40.3 mmol) instead of phenylboronic acid, compound 8a-1 (11.1) was used in the same manner as in the preparation of compound 2a-1 of Preparation Example 1-2. g, yield 70%; MS:[M+H] ⁺ =395) was prepared.

2) Preparation of compound 8a-2

Compound 8a-2 (10.7 g, yield 78%; MS:[M+) in the same manner as the method of preparing compound 2a-1, except that compound 8a-1 (11.1 g, 28.1 mmol) was used instead of compound 2a-1. H] ⁺ =487) was prepared.

Preparation Example 1-9: Synthesis of the compound of Intermediate 9a-2

1) Preparation of compound 9a-1

Except for using (phenyl-d5) boronic acid (8.5 g, 67.2 mmol) instead of phenylboronic acid, compound 9a-1 (15.9 g , Yield 79%; MS:[M+H] ⁺ =300) was prepared.

2) Preparation of compound 9a-2

Compound 9a-2 (15.6 g, yield 75%; MS:[M+) in the same manner as the method of preparing compound 2a-1, except that compound 9a-1 (15.9g, 53.2 mmol) was used instead of compound 2a-1. H] ⁺ =392) was prepared.

[Production Example 2]

Preparation Example 2-1: Preparation of Compound 1

2a-2 (5 g, 12.9 mmol) and 2-chloro-4- (dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine (4.6 g, 12.9 mmol) in a nitrogen atmosphere Into 100 ml of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (5.4 g, 38.8 mmol) was dissolved in 5 ml of water, and after sufficiently stirring, bis (tritertiary-butylphosphine) palladium (0.2 g, 0.4 mmol) was added. After reacting for 8 hours, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 451 mL of dichlorobenzene, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from dichlorobenzene and ethyl acetate to prepare a white solid compound 1 (5g, 67%, MS: [M+H]+ = 582.2).

Preparation Example 2-2: Preparation of Compound 2

2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine instead of 2-chloro-4-(dibenzothiophen-4-yl)-6-(phenyl Compound 2 was prepared in the same manner as in Preparation Example 2-1 except that -d5)-1,3,5-triazine was used (5.8 g, yield 74%, MS: [M+H ] ⁺ = 603).

Preparation Example 2-3: Preparation of Compound 3

2-(4-chloro-6-phenyl-1,3,5-triazine-2 instead of 2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine Compound 3 was prepared in the same manner as in Preparation Example 2-1 except that -yl)-9-phenyl-9H-carbazole was used (5.6 g, yield 66%, MS: [M+H ] ⁺ = 657).

Preparation Example 2-4: Preparation of compound 4

2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine instead of 9-(4-chloro-6-phenyl-1,3,5-triazine-2 -Yl)-9H-carbazole-1,3,4,5,6,8-d6 Except for using the compound 4 was prepared in the same manner as the preparation of compound 1 of Preparation Example 2-1 (5.7 g, Yield 75%, MS:[M+H] ⁺ = 587).

Preparation Example 2-5: Preparation of compound 5

Compound 3a-2 and 9-(4-chloro-6-phenyl- instead of compound 2a-2 and 2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine- Compound 5 was prepared in the same manner as in Preparation Example 2-1 except for using 1,3,5-triazin-2-yl)-9H-carbazole (5.1 g, yield 72%, MS:[M+H] ⁺ = 657).

Preparation Example 2-6: Preparation of Compound 6

Compound 2a-2 and 2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine instead of compound 3a-2 and 2-chloro-4-(dibenzofuran- 1-yl)-6-phenyl-1,3,5-triazine was prepared in the same manner as in the preparation of compound 1 of Preparation Example 2-1 except for using compound 6 (4.8 g, yield 68%, MS :[M+H] ⁺ = 658).

Preparation Example 2-7: Preparation of Compound 7

Compound 2a-2 and 2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine instead of compound 4a-2 and 2-chloro-4-(dibenzothiophene Compound 7 was prepared in the same manner as in Preparation Example 2-1, except that -4-yl)-6-phenyl-1,3,5-triazine was used (5.0 g, yield 69%, MS:[M+H] ⁺ = 674

Preparation Example 2-8: Preparation of compound 8

Compound 2a-2 and 2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine instead of compound 4a-2 and 2-chloro-4-(dibenzofuran- 2-yl)-6-phenyl-1,3,5-triazine was prepared in the same manner as in the preparation of compound 1 of Preparation Example 2-1 except that the compound 8 was prepared (5.1 g, yield 72%, MS :[M+H] ⁺ = 674)

Preparation Example 2-9: Preparation of Compound 9

Compound 4a-2 and 9-(4-chloro-6-phenyl- instead of compound 2a-2 and 2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine- Compound 9 was prepared in the same manner as in Preparation Example 2-1 except for using 1,3,5-triazin-2-yl)-2-phenyl-9H-carbazole (5.2 g, Yield 66%, MS: [M+H] ⁺ = 733)

Preparation Example 2-10: Preparation of Compound 10

Compound 2a-2 and 2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine instead of compound 6a-2 and 2-chloro-4-(dibenzofuran- 4-yl)-6-phenyl-1,3,5-triazine was prepared in the same manner as in Preparation Example 2-1, except that compound 1 was used (4.6 g, yield 66%, MS :[M+H] ⁺ = 698)

Preparation Example 2-11: Preparation of Compound 11

Compound 2a-2 and 2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine instead of compound 6a-2 and 9-(4-chloro-6-phenyl- Compound 11 was prepared in the same manner as in Preparation Example 2-1 except for using 1,3,5-triazin-2-yl)-3-phenyl-9H-carbazole (5.3 g, Yield 69%, MS:[M+H] ⁺ = 773)

Preparation Example 2-12: Preparation of Compound 12

Compound 2a-2 and 2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine instead of compound 7a-2 and 2-chloro-4-(dibenzothiophene Compound 12 was prepared in the same manner as in Preparation Example 2-1, except that -3-yl)-6-phenyl-1,3,5-triazine was used (5.2 g, yield 70%, MS:[M+H] ⁺ = 648)

Preparation Example 2-13: Preparation of compound 13

Instead of compound 2a-2 and 2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine, compound 7a-2 and 3-(4-chloro-6-phenyl- Compound 13 was prepared in the same manner as in Preparation Example 2-1 except for using 1,3,5-triazin-2-yl)-9-phenyl-9H-carbazole (5.1 g, Yield 63%, MS:[M+H] ⁺ = 707)

Preparation Example 2-14: Preparation of compound 14

Instead of compound 2a-2 and 2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine, compound 8a-2 and 2-chloro-4-(dibenzofuran- 4-yl)-6-(phenyl-d5)-1,3,5-triazine was prepared in the same manner as in Preparation Example 2-1 except for using compound 14 (4.4 g, yield 64%, MS:[M+H] ⁺ = 687)

Preparation Example 2-15: Preparation of compound 15

Compound 2a-2 and 2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine instead of compound 8a-2 and 2-chloro-4-(dibenzothiophene Compound 15 was prepared in the same manner as in Preparation Example 2-1, except that -2-yl)-6-phenyl-1,3,5-triazine was used (4.7 g, yield 67%, MS:[M+H] ⁺ = 698)

Preparation Example 2-16: Preparation of compound 16

Compound 2a-2 and 2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine instead of compound 9a-2 and 4-(4-chloro-6-phenyl- Compound 16 was prepared in the same manner as in Preparation Example 2-1 except that 1,3,5-triazin-2-yl)-9-phenyl-9H-carbazole was used (5.2 g, Yield 61%, MS:[M+H] ⁺ = 662)

Preparation Example 2-17: Preparation of compound 17

Instead of compound 2a-2 and 2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine, compound 9a-2 and 2-chloro-4-(dibenzofuran- Compound 17 was prepared in the same manner as in Preparation Example 2-1 except for using 4-yl)-6-phenyl-1,3,5-triazine (4.1 g, yield 55%, MS :[M+H] ⁺ = 587)

Preparation Example 2-18: Preparation of compound 18

Compounds 9a-2 and 9-(4-(3-chlorophenyl) instead of compound 2a-2 and 2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine Compound 18 was prepared in the same manner as in Preparation Example 2-1 except for using -6-phenyl-1,3,5-triazine-2-yl)-9H-carbazole (5.7 g, Yield 67%, MS: [M+H] ⁺ = 662)

[Example]

Example 1

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,300 Å was placed in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. 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.

On the ITO transparent electrode prepared as described above, the following hexanitrile hexaazatriphenylene (HAT) compound was thermally vacuum deposited to a thickness of 500 Å to form a hole injection layer. The HT-1 compound was thermally vacuum deposited to a thickness of 800 Å on the hole injection layer, and the HT-2 compound was sequentially vacuum deposited to a thickness of 500 Å to form a hole transport layer. Subsequently, on the hole transport layer, compound 1 prepared as a host, the following H1 compound, and a phosphorescent dopant GD were co-deposited at a weight ratio of 47:47:6 to form a light emitting layer having a thickness of 350Å. A hole blocking layer is formed by vacuum depositing an ET-1 material to a thickness of 50 Å on the emission layer, and 250 Å electrons by vacuum depositing an ET-2 material and LiQ (Lithium Quinolate) on the hole blocking layer at a weight ratio of 1:1 A transport layer was formed. Lithium pyride (LiF) having a thickness of 10 Å was sequentially deposited on the electron transport layer, and aluminum was deposited thereon to a thickness of 1000 Å to form a negative electrode.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 Å/sec, the deposition rate of lithium fluoride at the cathode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum degree during deposition was 1 × 10. ^-7 ~ 5 × 10 ^-8 torr was maintained.

Examples 2 to 18

Organic light-emitting devices of Examples 2 to 18 were fabricated in the same manner as in Example 1, except that the emission layer was formed as a host instead of Compound 1 as shown in Table 1 below.

Comparative Examples 1 to 5

Organic light-emitting devices of Comparative Examples 1 to 5 were fabricated using the same method as in Example 1, except that the following C1 to C5 were used as in Table 1 instead of Compound 1 as a host when forming the emission layer. I did.

[Experimental Example]

By applying a current to the organic light emitting device prepared in Examples 1 to 18 and Comparative Examples 1 to 5, voltage, efficiency and lifetime were measured, and the results are shown in Table 1 below. T95 refers to the time it takes for the luminance to decrease to 95% from the initial luminance.

division	compound	Voltage(V)(@10mA/cm 2 )	Efficiency(Cd/A)(@10mA/cm 2 )	Color coordinate (x,y)	Life (h)(LT 95 at 50mA/cm 2 )
Experimental Example 1	Compound 1	4.3	60	0.36, 0.61	100
Experimental Example 2	Compound 2	4.3	62	0.36, 0.62	115
Experimental Example 3	Compound 3	4.2	60	0.35, 0.60	97
Experimental Example 4	Compound 4	4	59	0.35, 0.61	110
Experimental Example 5	Compound 5	4.1	60	0.35, 0.60	105
Experimental Example 6	Compound 6	4.2	58	0.36, 0.61	95
Experimental Example 7	Compound 7	4.2	61	0.36, 0.61	100
Experimental Example 8	Compound 8	4.2	62	0.36, 0.63	100
Experimental Example 9	Compound 9	4.1	62	0.35, 0.62	103
Experimental Example 10	Compound 10	4.2	61	0.36, 0.62	98
Experimental Example 11	Compound 11	4	60	0.35, 0.61	95
Experimental Example 12	Compound 12	4.4	57	0.35, 0.63	90
Experimental Example 13	Compound 13	4.4	56	0.36, 0.62	96
Experimental Example 14	Compound 14	4.3	60	0.36, 0.62	98
Experimental Example 15	Compound 15	4.3	61	0.36, 0.61	90
Experimental Example 16	Compound 16	4.2	62	0.35, 0.61	110
Experimental Example 17	Compound 17	4.2	62	0.35, 0.61	115
Experimental Example 18	Compound 18	4	60	0.36, 0.63	102
Comparative Experimental Example 1	C1	4.2	55	0.35, 0.61	80
Comparative Experiment 2	C2	3.9	66	0.36, 0.61	60
Comparative Experiment 3	C3	4.5	71	0.38, 0.60	55
Comparative Experimental Example 4	C4	4.2	55	0.35, 0.61	50
Comparative Experimental Example 5	C5	4.9	56	0.35, 0.61	35

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 light-emitting layer exhibits superior performance in terms of efficiency and lifetime compared to the organic light-emitting device of Comparative Example.

In particular, the organic light-emitting device according to the embodiment of the present invention has a high efficiency characteristic by 10% increase compared to Comparative Experimental Example 1 using compound C1, which is a phosphorescent host material that is commonly used, and has a lifespan of about 10-43%. As it increased, it could be confirmed that it is a compound having long life characteristics.

It can be seen that the device characteristics are significantly different depending on the type of the triazine-based substituent substituted at the 6th position of dibenzothiophene. When the substituent of Rb is dibenzofuran, it can be confirmed that the compounds of the present invention have long life characteristics compared to Comparative Example C2 in which an additional aryl substituent is substituted. In addition, it was confirmed that the compounds of the present invention in which Rb contains any one of dibenzofuran, dibenzothiophene and carbazole substituents exhibit high efficiency and long life characteristics compared to Comparative Examples C4 and C5 containing only an aryl group.

In addition, compared to Comparative Experimental Example C3 in which the aryl substituent at the 2nd position of dibenzothiophene is not substituted, it can be confirmed that in the case of the compound of the present invention substituted with the aryl substituent at the 2nd position, the lifespan is improved by about 2.5 to 3 times or more. I can. In addition, it was confirmed that the compounds 2, 4, 14, and 16 to 18, which are compounds of the present invention in which deuterium is substituted, exhibits superior performance in terms of life as compared to materials in which deuterium is not substituted.

As described above, it was confirmed that the compounds of the present invention exhibited superior properties in terms of efficiency and life according to the position of the substituent and the type of the substituent compared to the comparative compounds.

Explanation of sign

1: substrate 2: anode

3: light emitting layer 4: cathode

5: hole injection layer 6: hole transport layer

7: electron suppression layer 8: electron transport layer

9: electron injection layer

Claims (13)

1. Compound represented by the following formula (1):

   [Formula 1]

   

   In Formula 1,

   X ₁ , X ₂ , and X ₃ are each independently N or CH, provided that at least one of X ₁ , X ₂ and X ₃ is N,

   L is a direct bond, a substituted or unsubstituted C _6-60 arylene, or a substituted or unsubstituted C _5-60 heteroarylene containing at least one hetero atom selected from the group consisting of N, O and S ,

   Ra is substituted or unsubstituted C _6-60 aryl,

   Rb is any one selected from compounds represented by the following,

   

   Each R ₁ is independently hydrogen, deuterium, or substituted or unsubstituted C _6-60 aryl,

   R ₂ is substituted or unsubstituted C _6-60 aryl,

   p is an integer from 0 to 5,

   n is each independently an integer of 1 to 7,

   m is an integer from 1 to 8.
2. The method of claim 1,

   L is a direct bond, or phenylene, the compound.
3. The method of claim 1,

   Ra is phenyl, biphenylyl, terphenylyl, dimethylfluorenyl, naphthyl, phenanthrenyl or triphenylenyl,

   These compounds are substituted or unsubstituted with one or more deuterium.
4. The method of claim 1,

   Each R ₁ is independently hydrogen, deuterium, or phenyl unsubstituted or substituted with one or more deuterium.
5. The method of claim 1,

   R ₂ is phenyl.
6. The method of claim 1,

   n is an integer of 1 to 6, the compound.
7. The method of claim 1,

   m is an integer of 1 to 6, the compound.
8. The method of claim 1,

   The compound represented by Formula 1 is any one selected from the group consisting of:

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   .
9. 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 8. That is, an organic light-emitting device.
10. The method of claim 9,

    The organic material layer including the compound is an emission layer, an organic light-emitting device.
11. The method of claim 10,

    The compound is a host compound, an organic light-emitting device.
12. The method of claim 10,

    The emission layer further includes a dopant compound.
13. The method of claim 9,

    The organic material layer containing the compound may include an electron injection layer; Electron transport layer; Or an organic light-emitting device that is a layer that simultaneously injects and transports electrons.

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