KR102392659B1 - 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 using the same.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and 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 layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device, and may include, for example, 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 the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up.

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

Korean Patent Publication No. 10-2013-073537

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

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

A 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 one or more heteroatoms 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 the compounds represented by

R ₁ is each 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;

In addition, the present invention is a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of the present invention as described above.

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

1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a light emitting layer 3 , and a cathode 4 .
2 is 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 a cathode 4 .

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

(Explanation of terms)

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

means a bond connected to another substituent.

As used herein, the term "substituted or unsubstituted" refers to deuterium (D); halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amino group; a phosphine oxide group; alkoxy group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; heteroarylamine group; arylamine group; an arylphosphine group; Or N, O, and S atom means that it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing one or more, or substituted or unsubstituted, two or more of the above-exemplified substituents are linked. . For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

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

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

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

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

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 10. 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 linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. 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 carbon number of the cycloalkyl group is 3 to 20. 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 is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, or a terphenyl group, but 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,

etc. can be However, the present invention 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 carbon atoms is not particularly limited, but it is preferably from 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an 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 group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but is not limited thereto.

In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as the 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 above-described alkyl group. In the present specification, the description of the heterocyclic group described above for heteroaryl among heteroarylamines may be applied. In the present specification, the alkenyl group among the aralkenyl groups is the same as the above-described examples of the alkenyl group. In the present specification, the description of the above-described aryl group may be applied, except that arylene is a divalent group. In the present specification, the description of the above-described heterocyclic group may be applied, except that heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the above-described aryl group or cycloalkyl group may be applied, except that it is formed by combining two substituents. In the present specification, the heterocyclic group is not a monovalent group, and the description of the above-described heterocyclic group may be applied, except that it is formed by combining two substituents.

(compound)

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

[Formula 1]

)가 치환되며, 코어의 다른 위치인 C₁, C₃, C₄, C₇, C₈, C₉의 탄소는 모두 수소로 치환된다.In Formula 1, an aryl group (Ra) is substituted at the 2nd position of the dibenzothiophene core, and a triazine-based substituent at the 6th position (

) is substituted, and all carbons of C ₁ , C ₃ , C ₄ , C ₇ , C ₈ , and C ₉ at 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 one or more heteroatoms 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 the compounds represented by

R ₁ is each 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;

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 including an aryl group at the 2-position and a triazine-based substituent at the 6-position of dibenzothiophene. In particular, the triazine-based substituent is dibenzofuran or dibenzothiophene. , by including an additional substituent of any one of carbazole, it is possible to improve the electron injection and electron transfer rate, and accordingly, the organic light emitting device employing the compound of the present invention exhibits high efficiency, low driving voltage, and high luminance, especially , excellent long life characteristics. In particular, when the triazine-based substituent is dibenzofuran or dibenzothiophene, lifespan characteristics can be significantly improved even without additional substituents.

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

[Scheme A]

In Scheme A, variables other than Z ₁ and Z ₂ are as defined above, and Z ₁ and Z ₂ are each independently halogen, preferably chloro or bromo.

In Scheme A, the reactants, catalysts, solvents, etc. used may be suitably changed for the desired product. The preparation method of the compound of Formula 1 may be more specific in Preparation Examples to be described later.

(organic light emitting element)

The present invention provides an organic light emitting device comprising the compound represented by Formula 1 above. In one example, the present invention provides a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound represented by Formula 1 above. 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 multi-layer 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, etc. 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 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, the hole transport layer, or a layer that simultaneously injects and transports holes is represented by Formula 1 The indicated compounds are included.

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

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

In addition, the organic layer may include an electron transport layer, an electron injection layer, or a layer that transports and injects electrons at the same time, and the electron transport layer, the electron injection layer, or a layer that simultaneously transports and injects electrons is represented by the above formula The compound represented by 1 is included.

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 the organic light emitting diode 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 including 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 light emitting layer.

2 is 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 a cathode 4 . 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 using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Formula 1 above. Also, 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 diode 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, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode And, after forming an organic 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 into 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 this 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.

In one example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

As the anode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, 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; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and as a hole injection material, it has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect on the light emitting layer or the light emitting material, and is produced in the light emitting layer A compound which prevents the movement of excitons to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferable. It is preferable that the highest occupied molecular orbital (HOMO) 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 the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, and conductive polymers of polyaniline and polythiophene series, but are not limited thereto.

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

The electron blocking layer is a layer placed between the hole transport layer and the emission layer in order to prevent electrons injected from the cathode from passing to the hole transport layer without recombination in the emission layer, and is also called an electron blocking layer. A material having an electron affinity lower than that of the electron transport layer is preferable for the electron suppressing layer.

The light emitting material is a material capable of emitting light in the visible ray 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 include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

The emission layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. 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. As the styrylamine compound, a substituted or unsubstituted It is a compound in which at least one arylvinyl group is substituted in the arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but is not limited thereto. In addition, examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light emitting layer. 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 may be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum layer or a silver layer.

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 which prevents movement to a layer and is excellent in the ability to form a thin film is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals 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-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

The organic light emitting device according to the present invention may be a top emission type, a back emission type, or a double side 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 compound represented by Formula 1 and the preparation of an organic light emitting device including the same will be described in detail in Examples below. However, the following examples are intended to illustrate 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

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

Preparation 1-2: compound synthesis 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 placed in 600 ml of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (41.8 g, 302.4 mmol) was dissolved in 42 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (3.5 g, 3 mmol) was added. After the reaction 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, the organic layer was separated, anhydrous magnesium sulfate was added, 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 (25.6 g, 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, and stirred and refluxed. After that, potassium acetate (25 g, 260.5 mmol) was added, and after sufficient stirring, palladium dibenzylideneacetone palladium (1.5 g, 2.6 mmol) and tricyclohexylphosphine (1.5 g, 5.2 mmol) were added. After reaction for 7 hours, after cooling to room temperature, the organic layer was filtered to remove salt, and the filtered organic layer was distilled. This was added to 335 mL of chloroform to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to prepare an ivory-colored solid compound 2a-2 (26.8 g, 80%, MS: [M+H] + = 387.3).

Preparation 1-3: compound synthesis of intermediate 3a-2

1) Preparation of compound 3a-1

Except for using [1,1'-biphenyl]-4-yl boronic acid (10 g, 50.4 mmol) instead of phenylboronic acid, the same method as for preparing compound 2a-1 of Preparation Example 1-2 was prepared as 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+ H] ⁺ =463).

Preparation 1-4: compound synthesis of intermediate 4a-2

1) Preparation of compound 4a-1

Except for using [1,1'-biphenyl]-3-yl boronic acid (13.7 g, 50.4 mmol) instead of phenylboronic acid, the same method as the method for preparing compound 2a-1 of Preparation Example 1-2 was prepared as 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+ H] ⁺ =463).

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

1) Preparation of compound 5a-1

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

2) Preparation of compound 5a-2

Compound 5a-2 (17.8 g, yield 79%; MS:[M+ H] ⁺ =539) was prepared.

Preparation 1-6: compound synthesis of intermediate 6a-2

1) Preparation of compound 6a-1

A method of 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+ H] ⁺ =503) was prepared.

Preparation 1-7: compound synthesis 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 for 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+ H] ⁺ =437.2).

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 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+ H] ⁺ =487).

Preparation Example 1-9: Synthesis of 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, in the same manner as for preparing Compound 2a-1 of Preparation Example 1-2, 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+ 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) were prepared in a nitrogen atmosphere. It was put into 100ml of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (5.4 g, 38.8 mmol) was dissolved in 5 ml of water, and after stirring sufficiently, bis(tritertiary-butylphosphine)palladium (0.2 g, 0.4mmol) was added. After 8 hours of reaction, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 451 mL of dichlorobenzene, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, 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 (5 g, 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 -d5)-1,3,5-triazine was prepared in the same manner as in Preparation of Compound 1 of Preparation Example 2-1, except that Compound 2 was prepared (5.8 g, yield 74%, MS: [M+H ] ⁺ = 603).

Preparation 2-3: Preparation of compound 3

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

Preparation Example 2-4: Preparation of compound 4

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

Preparation Example 2-5: Preparation of compound 5

Compound 2a-2 and 2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine instead of compound 3a-2 and 9-(4-chloro-6-phenyl- 1,3,5-triazin-2-yl)-9H-carbazole was prepared in the same manner as in the preparation of compound 1 of Preparation Example 2-1, except that compound 5 was prepared (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 that compound 6 was prepared (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) -4-yl)-6-phenyl-1,3,5-triazine was prepared in the same manner as in Preparation of Compound 1 of Preparation Example 2-1, except that Compound 7 was prepared (5.0 g, yield 69%, MS:[M+H] ⁺ = 674

Preparation 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 compound 8 was prepared (5.1 g, yield 72%, MS :[M+H] ⁺ = 674)

Preparation Example 2-9: Preparation of compound 9

Compound 2a-2 and 2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine instead of compound 4a-2 and 9-(4-chloro-6-phenyl- 1,3,5-triazin-2-yl)-2-phenyl-9H-carbazole was prepared in the same manner as in Preparation of Compound 1 of Preparation Example 2-1, except that Compound 9 was prepared (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 of Compound 1 of Preparation Example 2-1, except that Compound 10 was prepared (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- 1,3,5-triazin-2-yl)-3-phenyl-9H-carbazole was prepared in the same manner as in Preparation of Compound 1 of Preparation Example 2-1, except that Compound 11 was prepared (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) -3-yl)-6-phenyl-1,3,5-triazine was prepared in the same manner as in Preparation of Compound 1 of Preparation Example 2-1, except that Compound 12 was prepared (5.2 g, yield 70%, MS:[M+H] ⁺ = 648)

Preparation Example 2-13: Preparation of compound 13

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

Preparation Example 2-14: Preparation of compound 14

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-(dibenzofuran- 4-yl)-6-(phenyl-d5)-1,3,5-triazine was prepared in the same manner as in Preparation of Compound 1 of Preparation Example 2-1, except that Compound 14 was prepared (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) -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 compound 15 was prepared (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- 1,3,5-triazin-2-yl)-9-phenyl-9H-carbazole was prepared in the same manner as in Preparation of Compound 1 of Preparation Example 2-1, except that Compound 16 was prepared (5.2 g, Yield 61%, MS: [M+H] ⁺ = 662)

Preparation Example 2-17: Preparation of compound 17

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

Preparation Example 2-18: Preparation of compound 18

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

[Example]

Example 1

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,300 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was 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. Then, on the hole transport layer, compound 1 prepared as a host, the following H1 compound, and phosphorescent dopant GD were co-deposited in a weight ratio of 47:47:6 to form an emission layer having a thickness of 350 Å. A hole blocking layer was formed by vacuum-depositing an ET-1 material to a thickness of 50 Å on the light emitting layer, and ET-2 material and Lithium Quinolate (LiQ) were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron of 250 Å. A transport layer was formed. Lithium fluoride (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 cathode.

In the above process, the deposition rate of organic material was maintained at 0.4 ~ 0.7 Å/sec, the deposition rate of lithium fluoride of the negative electrode 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 to 5 × 10 ^-8 torr was maintained.

Examples 2 to 18

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

Comparative Examples 1 to 5

Organic light emitting devices of Comparative Examples 1 to 5 were respectively manufactured using the same method as in Example 1, except that C1 to C5 as shown in Table 1 below were used instead of Compound 1 as a host when the light emitting layer was formed. did

[Experimental example]

By applying a current to the organic light emitting diodes manufactured 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 means the time required for the luminance to decrease from the initial luminance to 95%.

division compound Voltage (V)
(@10mA/cm ² ) Efficiency (Cd/A)
(@10mA/cm ² ) color coordinates
(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 Experimental Example 2 C2 3.9 66 0.36, 0.61 60 Comparative Experimental Example 3 C3 4.5 71 0.38, 0.60 55 Comparative Experimental Example 4 C4 4.2 55 0.35, 0.61 50 Comparative Experiment 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 using the compound according to the present invention as a host of the light emitting layer exhibits superior performance in terms of efficiency and lifespan compared to the organic light emitting device of Comparative Example.

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

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 a longer lifespan 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 includes any one of dibenzofuran, dibenzothiophene, and carbazole substituents exhibit high efficiency and long lifespan 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, in the case of the compound of the present invention in which the aryl substituent is substituted at the 2nd position, it can be confirmed that the lifespan is improved by about 2.5 to 3 times or more. can In addition, it was confirmed that compounds 2, 4, 14, and 16 to 18, which are compounds of the present invention in which deuterium is substituted, exhibit superior performance in terms of lifespan compared to materials in which deuterium is not substituted.

As described above, it was confirmed that the compounds of the present invention exhibit superior properties in terms of efficiency and lifespan according to the position of the substituent and the type of the substituent compared to the compounds of Comparative Examples.

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)

A 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, or phenylene,
Ra is C _6-60 aryl unsubstituted or substituted with one or more deuterium,
Rb is any one selected from the compounds represented by

R ₁ is each 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 from 1 to 7,
m is an integer from 1 to 8;
delete The method of claim 1,
Ra is phenyl, biphenylyl, terphenylyl, dimethylfluorenyl, naphthyl, phenanthrenyl or triphenylenyl,
They are unsubstituted or substituted with one or more deuterium.
The method of claim 1,
R ₁ is each independently hydrogen, deuterium, or phenyl unsubstituted or substituted with one or more deuterium.
The method of claim 1,
R ₂ is phenyl.
The method of claim 1,
n is an integer from 1 to 6.
The method of claim 1,
m is an integer from 1 to 6.
The method of claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of:

.
a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers is in any one of claims 1 and 3 to 8. Which comprises a compound according to the, organic light emitting device.
10. The method of claim 9,
The organic material layer including the compound is a light emitting layer, an organic light emitting device.
11. The method of claim 10,
The compound is a host compound, an organic light emitting device.
11. The method of claim 10,
The light emitting layer further comprises a dopant compound, the organic light emitting device.
10. The method of claim 9,
The organic material layer containing the compound may include an electron injection layer; electron transport layer; Or a layer that simultaneously injects and transports electrons, an organic light emitting device.

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