KR20210016181A - Organic light emitting device - Google Patents

Abstract

The present invention provides an organic light emitting element which can improve life characteristics. The organic light emitting element comprises an anode, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode.

Description

Organic light emitting device TECHNICAL FIELD

The present invention relates to an organic light emitting device.

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.

On the other hand, in recent years, in order to reduce process cost, an organic light emitting device using a solution process, in particular an inkjet process, instead of a conventional deposition process has been developed. In the early days, an attempt was made to develop an organic light-emitting device by coating all organic light-emitting device layers by a solution process, but the current technology has limitations, so only HIL, HTL, and EML are processed in a solution process in the form of a regular structure, and the later process is the existing deposition process. A hybrid process that utilizes is being studied.

Korean Patent Publication No. 10-2000-0051826

The present invention relates to an organic light emitting device.

The present invention provides the following organic light emitting device:

anode;

Hole transport layer;

Light-emitting layer;

Electron transport layer; And

Including a cathode,

The emission layer includes a compound represented by Formula 1 below,

The electron transport layer comprises a compound represented by the following formula (2),

Organic light emitting element:

[Formula 1]

In Formula 1,

Ar ₁ is substituted or unsubstituted C _6-60 aryl,

Ar ₂ is substituted at the position of *1 or *2, and is -L-Ar ₃ ,

L is a substituted or unsubstituted C _6-60 arylene,

Ar ₃ is substituted or unsubstituted C _6-60 aryl,

R ₁ , R ₂ and R ₃ are each independently hydrogen, deuterium, substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,

n1 and n2 are each independently an integer of 1 to 4,

n3 is an integer of 1 to 3,

[Formula 2]

In Chemical Formula 2,

Each A'is independently a benzene ring, a naphthalene ring, or a pyridine ring fused with an adjacent ring,

One of R'is a substituent represented by the following formula (3), and the others are each independently hydrogen; heavy hydrogen; halogen; Nitrile; Nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; A substituted or unsubstituted C _2-60 alkenyl group; Substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heteroaryl including at least one of O, N, Si and S,

[Formula 3]

In Chemical Formula 3,

L'is a single bond; Substituted or unsubstituted C _6-60 arylene; Or a substituted or unsubstituted C _2-60 heteroarylene including at least one of O, N, Si and S,

X'is O, S, or Se,

을 형성한다.Ar' ₁ and Ar' ₂ are each independently a substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl including one or more of O, N, Si, and S, or Ar' ₁ , Ar' ₂ , and Ar' ₁ and Ar' ₂ are bonded P with

To form.

The organic light-emitting device described above may improve efficiency, low driving voltage, and/or lifespan characteristics in the organic light-emitting device by controlling the compound included in the emission layer.

1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, an electron transport layer 5, and a cathode 6.
2 is a substrate (1), an anode (2), a hole injection layer (7), a hole transport layer (3), a light emitting layer (4), an electron transport layer (5), an electron injection layer (8) and a cathode (6). An example of an organic light emitting device is shown.
3 shows GC-MS data of the compound prepared in Preparation Example 1-4.

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

또는

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

or

Means a bond connected to another substituent.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or it means 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.

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. 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, isoxazolyl group, thiiadia There may be a zolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.

In the present specification, the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group and the alkylamine group is the same as the example of the aforementioned alkyl group. In the present specification, for heteroaryl among heteroarylamines, the description of the aforementioned heterocyclic group may be applied. In the present specification, the alkenyl group of the aralkenyl group is the same as the example of the alkenyl group described above. In the present specification, the description of the aryl group described above may be applied except that the arylene is a divalent group. In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aryl group or 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.

The present invention, the anode; Hole transport layer; Light-emitting layer; Electron transport layer; And a cathode, wherein the emission layer includes the compound represented by Formula 1, and the electron transport layer includes the compound represented by Formula 2. It provides an organic light-emitting device.

The organic light-emitting device according to the present invention can improve efficiency, low driving voltage, and/or lifetime characteristics in the organic light-emitting device by controlling the compound included in the emission layer and the compound included in the electron transport layer.

Hereinafter, the present invention will be described in detail for each configuration.

Anode and cathode

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.

In addition, a hole injection layer may be additionally included on the anode. The hole injection layer is made of a hole injection material, and the hole injection material has the ability to transport holes, and thus has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material. A compound that prevents migration to the electron injection layer or the electron injection material and has excellent thin film formation ability 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 the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene There are a series of organic substances, anthraquinone, and polyaniline and a polythiophene series of conductive polymers, but are not limited thereto.

Hole injection layer

The organic light-emitting device according to the present invention may include a hole injection layer between the anode and the hole transport layer, if necessary.

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.

Hole transport layer

The hole transport layer used in the present invention is a layer that receives holes from the anode or the hole injection layer formed on the anode and transports holes to the emission layer, and can be transferred to the emission layer by transporting holes from the anode or the hole injection layer as a hole transport material. A material with high mobility for holes 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.

Emitting layer

The light-emitting material included in the light-emitting layer is a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. The light-emitting layer may include a host material and a dopant material. In particular, in the present invention, a compound represented by Formula 1 is used as the host material.

The compound represented by Formula 1 has a high solubility in an organic solvent due to its structural characteristics, and thus, a light emitting layer can be formed by a solution process when manufacturing an organic light emitting device.

In Formula 1, the meaning that Ar ₂ is substituted at the position of *1 or *2 means the following structures, respectively:

Preferably, Ar ₁ is phenyl or naphthyl, and the phenyl or naphthyl is unsubstituted or substituted with C _1-10 alkyl (more preferably tert-butyl).

Preferably, L is 1,2-phenylene, or 1,3-phenylene.

Preferably, Ar ₃ is phenyl, naphthyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, 9-phenyl-9H-carbazolyl, 9,9-dimethyl -9H-xanthenyl, or (naphthyl)anthracenyl.

Preferably, Ar ₂ is any one selected from the group consisting of:

.

.

Preferably, the sum of n1 and n2 is 1,

R ₁ and R ₂ are each independently hydrogen, or phenyl, or naphthyl, and the phenyl or naphthyl is unsubstituted or substituted with C _1-10 alkyl (preferably tert-butyl).

Preferably, R ₃ is hydrogen.

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

In addition, the compound represented by Formula 1 can be prepared in the same manner as in Scheme 1 below.

[Scheme 1]

In Reaction Scheme 1, the definitions other than X'are as defined above, and X'is halogen and more preferably chloro or bromo.

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

Meanwhile, examples of the dopant material 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.

Meanwhile, the compound represented by Formula 1 may form a light emitting layer through a solution process. To this end, the present invention provides a coating composition comprising the compound represented by Formula 1 and a solvent.

The solvent is not particularly limited as long as it is a solvent capable of dissolving or dispersing the compound represented by Formula 1, and examples thereof include chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, and chlorobenzene. and chlorine-based solvents such as o-dichlorobenzene; Ether solvents such as tetrahydrofuran and dioxane; Aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; Aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; Ketone solvents such as acetone, methyl ethyl ketone, and cyclohexanone; Ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; Polyvalents such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, etc. Alcohol and its derivatives; Alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; Sulfoxide solvents such as dimethyl sulfoxide; And amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; Benzoate solvents such as butyl benzoate and methyl-2-methoxybenzoate; Tetralin; Solvents, such as 3-phenoxytoluene, are mentioned. In addition, the above-described solvent may be used alone or in combination of two or more solvents. Preferably, toluene may be used as the solvent.

In addition, the coating composition may further include a compound used as the above-described dopant material.

In addition, the viscosity of the coating composition is preferably 1 cP to 10 cP, and coating is easy within the above range. In addition, the concentration of the compound represented by Chemical Formula 1 in the coating composition is preferably 0.1 wt/v% to 20 wt/v%.

Preferably, the solubility (wt%) of the coating composition in a solvent is 1.0 to 10.0, more preferably 2.5 to 10.0, based on the solvent toluene, and accordingly, the coating composition comprising the compound represented by Formula 1 is It is suitable for use in solution processing.

In addition, the present invention provides a method of forming a light emitting layer using the above-described coating composition. Specifically, coating the light emitting layer according to the present invention described above on the anode or on the hole transport layer formed on the anode by a solution process; And heat-treating the coated coating composition.

The solution process uses the coating composition according to the present invention described above, and means spin coating, dip coating, doctor blading, ink jet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.

In the heat treatment step, the heat treatment temperature is preferably 150 to 230°C. In addition, the heat treatment time is 1 minute to 3 hours, more preferably 10 minutes to 1 hour. In addition, the heat treatment is preferably performed in an inert gas atmosphere such as argon or nitrogen.

Electron transport layer

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer. As an electron transport material, electrons are well injected from the cathode and can be transferred to the emission layer. In particular, in the present invention, it is represented by Formula 2 above. Use a compound that can be used.

In Formula 2, preferably, all of A'are benzene rings; One of A'is a pyridine ring and the other is a benzene ring; One of A'is a naphthalene ring, and the other is a benzene ring; Or two of A'are naphthalene rings, and the rest are benzene rings.

Preferably, L'is phenylene, biphenylylene, naphthylene, phenanthrenylene, anthracenylene, pyridinylene, quinolinylene, or isoquinolinylene.

을 형성한다. Preferably, Ar' ₁ and Ar' ₂ are each independently phenyl, biphenylyl, or naphthyl; Or Ar' ₁ , Ar' ₂ , and Ar' ₁ and Ar' ₂ with P to which it is bound

To form.

Representative examples of the compound represented by Formula 2 are as follows:

In addition, a compound having the following structure among the compounds represented by Formula 2 may be prepared in the same manner as in Scheme 2 below, and the remaining compounds may be prepared in a similar manner.

[Scheme 2]

In Reaction Scheme 2, definitions other than X" are as defined above, and X" is halogen and more preferably bromo or chloro.

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

Electron injection layer

The organic light-emitting device according to the present invention may include an electron injection layer between the electron transport layer and the cathode, if necessary.

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.

Organic light emitting element

The structure of the organic light emitting device according to the present invention is illustrated in FIG. 1. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, an electron transport layer 5, and a cathode 6. In such a structure, the compound represented by Formula 1 may be included in the emission layer, and the compound represented by Formula 2 may be included in the electron transport layer layer.

2 is a substrate (1), an anode (2), a hole injection layer (7), a hole transport layer (3), a light emitting layer (4), an electron transport layer (5), an electron injection layer (8) and a cathode (6). An example of an organic light emitting device is shown. In such a structure, the compound represented by Formula 1 may be included in the emission layer, and the compound represented by Formula 2 may be included in the electron transport layer layer.

The organic light-emitting device according to the present invention may be manufactured by sequentially stacking the above-described configurations. 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 each of the above-described layers 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 light emitting layer may be formed by a solution coating method as well as a vacuum deposition method of a host and a dopant. 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.

Meanwhile, 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.

The fabrication of the organic light emitting device according to the present invention will be described in detail below. However, the following specific information is for illustrating the present invention, and the scope of the present invention is not limited thereto.

[Production Example]

Preparation Example 1-1: Preparation of Compound 1-1

Step 1-1: Preparation of intermediate compound INT-1

2,2'-dibromo-1,1'-biphenyl (7.0 g, 22.4 mmol, 1.0 eq) and 1-naphthalenyl boronic acid (4.6 g, 26.9 mmol, 1.2 eq), Pd(PPh ₃ ) ₄ (2.6 g, 2.2 mmol, 0.1 eq), and potassium carbonate (9.3 g, 67.3 mmol, 3.0 eq) were added to a 250 ml round bottom flask along with toluene (150 ml) and water (50 ml). After the degassing process, nitrogen was substituted and the temperature was raised to 100°C, followed by stirring overnight. Thereafter, the product was cooled to room temperature and extracted with dichloromethane. Next, after water removal with magnesium sulfate, it was adsorbed on dichloromethane, and 2.0 g (yield 25%) of the title compound was obtained by column chromatography using hexane as a solvent.

Step 1-2: Preparation of compound 1-1

Intermediate compounds INT-1 (2.0 g, 5.6 mol, 1.0 eq) prepared in step 1-1 and 10-(naphthalen-1-yl) anthracene-9-ylboronic acid (2.9 g, 8.4 mmol, 1.5 eq), Pd(PPh ₃ ) ₄ (0.7 g, 0.6 mmol, 0.1 eq), and potassium carbonate (2.3 g, 16.7 mmol, 3.0 eq) in a 250 ml round bottom flask with toluene (150 ml) and water (50 ml) Was added to. After the degassing process, nitrogen was substituted and the temperature was raised to 100°C, followed by stirring overnight. Thereafter, the product was cooled to room temperature and extracted with dichloromethane. Next, water was removed with magnesium sulfate, adsorbed on dichloromethane, and then subjected to column chromatography using dichloromethane/hexane (1:10) as an eluent, and then precipitated with dichloromethane/methanol to obtain 1.0 g of the title compound. . LC-MS data of the prepared compound 1-1 are as follows.

MS [M+H] ⁺ = 583.4

Preparation Example 1-2: Preparation of compound 1-2

1.5 g of the title compound was prepared in the same manner as in Preparation Example 1-1, except that 2-naphthalenyl boronic acid was used instead of 1-naphthalenyl boronic acid in step 1-1 of Preparation Example 1-1. Got it. LC-MS data of the prepared compound 1-2 are as follows.

MS [M+H] ⁺ = 583.4

Preparation Example 1-3: Preparation of compound 1-3

Preparation Example 1-2, except that 10-(naphthalen-2-yl) anthracene-9-ylboronic acid was used instead of 10-(naphthalen-1-yl) anthracene-9-ylboronic acid in Preparation Example 1-2. Using the same method as described above, 2.6 g of the title compound was obtained. LC-MS data of the prepared compound 1-3 are as follows.

MS [M+H] ⁺ = 583.4

Preparation Example 1-4: Preparation of compound 1-4

Step 1-1: Preparation of intermediate compound A1

2-Bromoanthracene (5 g, 19.45 mmol), naphthalen-1-ylboronic acid (4 g, 23.3 mmol), potassium carbonate (8.1 g, 58 mmol) toluene (65 ml), ethanol (20 ml), water After (20 ml) was added, the temperature was raised to 90°C and melted. Pd(PPh ₃ ) ₄ (1.1 g, 0.97 mmol) was added and reacted at 90° C. for about 24 hours. After the temperature was lowered, the organic layer was extracted with ethyl acetate [EA], moisture was removed with magnesium sulfate [MgSO ₄ ], and the residual catalyst was adsorbed with charcoal, and then filtered through celite and silica. The filtrate was concentrated, slightly dissolved in methylene chloride, and precipitated in ethanol to obtain 8.4 g of a white solid intermediate compound A1.

Step 1-2: Preparation of intermediate compound A2

Intermediate compound A1 (8.8 g, 28.91 mmol) obtained in step 1-1 and N-bromosuccinimide (5.4 g, 30.4 mmol) were added to DMF (200 ml) to dissolve the reaction, and then at room temperature for about 3 hours Reacted for a while. After quenching the reaction with water, a brown solid was obtained by filtering with water and methanol. After dissolving this solid with an excess of THF and EA, brine was added to extract the organic layer. After removing moisture with magnesium sulfate [MgSO ₄ ], it was concentrated and precipitated in ethanol to obtain 4.1 g of a yellow solid intermediate compound A2.

Step 1-3: Preparation of intermediate compound A3

[ ml) and water (30 ml), the temperature was raised to 100° C. and dissolved. Pd(PPh ₃ ) ₄ (0.61 g, 0.53 mmol) was added and reacted at 100° C. for about 3 hours. After the temperature was lowered, the organic layer was extracted with ethyl acetate [EA], moisture was removed with magnesium sulfate [MgSO ₄ ], and the residual catalyst was adsorbed with charcoal, and then filtered through celite and silica. The filtrate was adsorbed on silica and subjected to column chromatography to obtain about 1.4 g of intermediate compound A3.

Step 1-4: Preparation of intermediate compound A4

Intermediate compound A3 (1.4 g, 3.68 mmol) obtained in step 1-3 and N-bromosuccinimide (0.67 g, 3.79 mmol) were added to DMF (20 ml) to dissolve the reaction, and then at room temperature for about 3 hours Reacted for a while. After quenching the reaction with water, a brown solid was obtained by filtering with water and methanol. After dissolving this solid with an excess of THF and EA, brine was added to extract the organic layer. After removing moisture with magnesium sulfate [MgSO ₄ ], it was concentrated and precipitated in ethanol to obtain 1.4 g of a yellow solid intermediate compound A4.

Step 1-5: Preparation of compound 1-4

4,4,5,5-tetramethyl-2-(3-(10-(naphthalen-1-yl)anthracene-9-yl)phenyl)-1,3,2-dioxaborane (2.3 g, 4.6 mmol), intermediate compound A4 (1.4 g, 3.05 mmol) obtained in step 1-4, potassium carbonate (1.3 g, 9.15 mmol) in toluene (30 ml), ethanol (5 ml), and water (5 ml) After the addition, the temperature was raised to 90°C and melted. Pd(PPh ₃ ) ₄ (1.06g, 9.15mmol) was added and reacted at 90°C for about 3 hours. After lowering the temperature, the organic layer was extracted with ethyl acetate [EA], moisture was removed with magnesium sulfate [MgSO4], and the residual catalyst was adsorbed with charcoal, and then filtered through celite and silica. The filtrate was adsorbed on silica and subjected to column chromatography to obtain compound 1-4 (1.8 g). GC-MS data of the prepared compound 1-4 is shown in FIG. 3.

Preparation Example 1-5: Preparation of compound 1-5

The title compound was prepared in the same manner as in Preparation Example 1-4, except that (4-(tert-butyl)phenyl)boronic acid was used instead of phenylboronic acid in Steps 1-3 of Preparation Example 1-4.

MS [M+H] ⁺ = 816.37

Preparation Example 1-6: Preparation of compound 1-6

The title compound was prepared in the same manner as in Preparation Example 1-4, except that (4-(tert-butyl)phenyl)boronic acid was used instead of naphthalen-1-ylboronic acid in step 1-1 of Preparation Example 1-4. Was prepared.

MS [M+H] ⁺ = 766.35

Preparation Example 1-7: Preparation of Compound 1-7

The title compound was prepared in the same manner as in Preparation Example 1-4, except that naphthalene-1ylboronic acid was used instead of phenylboronic acid in Steps 1-3 of Preparation Example 1-4.

MS [M+H] ⁺ = 810.32

Preparation Example 2-1: Preparation of Compound 2-1

1) Preparation of compound 2-1-1

2,4-dichlorophenylboronic acid (18.3 g, 95.8 mmol) and 1-bromo-2-naphthaldehyde (20.5 g, 87.2 mmol) were completely dissolved in THF (300 mL) and then 2 M aqueous potassium carbonate solution ( 180 mL) was added and Pd(PPh ₃ ) ₄ (2.0 g, 2 mol%) was added, followed by stirring and refluxing for 5 hours. The temperature was lowered to room temperature, the water layer was removed, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, followed by column with tetrahydrofuran:hexane = 1:10 (v:v) to prepare compound 2-1-1 (21.0 g, 80%).

MS [M+H] ⁺ = 301

2) Preparation of compound 2-1-2

Compound 2-1-1 (26.2 g, 87.0 mmol) and benzene-1,2-diamine (9.4 g, 87.0 mmol) were suspended in dioxane (200 mL) and acetic acid (20 mL). The resulting mixture was stirred and refluxed for 6 hours, and then cooled to room temperature. After the mixture was diluted with water (100 mL), the resulting solid was filtered and washed with water and ethyl ether to prepare compound 2-1-2 (19.3 g, yield 57%).

MS [M+H] ⁺ = 389

3) Preparation of compound 2-1-3

Compound 2-1-2 (1.99 g, 5.10 mmol) and sodium-tertiary-butoxide (NaOt-Bu) (0.58 g, 6.01 mmol) and Pd[P(t-Bu) ₃ ] ₂ (51 mg, 2 mol%) was suspended in toluene (50 mL). The resulting mixture was stirred and refluxed for 6 hours, and then cooled to room temperature. Distilled water was added to the reaction solution to complete the reaction, and the organic layer was extracted, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and columned with tetrahydrofuran:hexane = 1:5 (v:v) to prepare compound 2-1-3 (0.756 g, yield 42%).

MS [M+H] ⁺ = 353

4) Preparation of compound 2-1-4

After dissolving compound 2-1-3 (12 g, 34 mmol), bis (pinacolato) diboron (12 g, 47 mmol), and potassium acetate (12 g, 118 mmol) in dioxane (150 mL), 50 The temperature was raised to °C, and Pd(dba) ₂ (0.23 g, 0.4 mmol) and P(Cy) ₃ (0.22 g, 0.8 mmol) were added, followed by heating and stirring for 12 hours. After cooling the reaction solution to room temperature, distilled water (100 mL) was added and extracted with methylene chloride (100 mL×3). The organic layer was concentrated and recrystallized with ethanol to obtain compound 2-1-4 (14 g, yield 90%).

MS [M+H] ⁺ = 445

5) Preparation of compound 2-1-5

2,6-dibromonaphthalene (20 g, 69.94 mmol) was dissolved in THF (100 mL), and then cooled to -78°C. After slowly adding n-BuLi (2.5 M, 37 ml, 93 mmol) dropwise, the mixture was stirred for 30 minutes. Chlorodiphenylphosphine (17 g, 76 mmol) was slowly added dropwise, stirred for 3 hours, raised to room temperature, water (100 mL) was added, and extracted with THF. The organic layer was concentrated and recrystallized with hexane to obtain compound 2-1-5 (21 g, yield 76.8%).

MS [M+H] ⁺ = 391

6) Preparation of compound 2-1-6

Compound 2-1-5 (20 g, 51 mmol) was dissolved in trichloromethane (200 mL), and then hydrogen peroxide solution (20 mL) was added, followed by stirring for 12 hours. MgSO ₄ , stirred to remove water, filtered, concentrated, and recrystallized with hexane to give compound 2-1-6 (18 g, yield 86.5%).

MS [M+H] ⁺ = 407

7) Preparation of compound 2-1

Compound 2-1-4 (9.0 g, 20.3 mmol) and compound 2-1-6 (9.1 g, 22.4 mmol) were added to THF (200 mL), heated to completely dissolve, and then a 2 M aqueous potassium carbonate solution (100 mL) Was added, and Pd(PPh ₃ ) ₄ (0.26 g, 0.22 mmol) was added and stirred for 12 hours. After lowering to room temperature, the water layer was removed, and the resulting solid was filtered. The filtered solid was recrystallized from tetrahydrofuran and acetone to obtain compound 2-1 (8.5 g, yield 65%).

MS [M+H] ⁺ = 645

Preparation Example 2-2: Preparation of Compound 2-2

1) Preparation of compound 2-2-1

2,4-dichlorophenylboronic acid (18.3 g, 95.8 mmol) and 2-bromo-1-naphthaldehyde (20.5 g, 87.2 mmol) were completely dissolved in THF (300 mL) and then 2 M aqueous potassium carbonate solution ( 180 mL) was added and Pd(PPh ₃ ) ₄ (2.0 g, 2 mol%) was added, followed by stirring and refluxing for 5 hours. The temperature was lowered to room temperature, the water layer was removed, and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and columned with tetrahydrofuran:hexane = 1:10 (v:v) to prepare compound 2-2-1 (21.0 g, yield 80%).

MS [M+H] ⁺ = 301

2) Preparation of compound 2-2-2

Compound 2-2-1 (26.2 g, 87.0 mmol) and benzene-1,2-diamine (9.4 g, 87.0 mmol) were suspended in dioxane (200 mL) and acetic acid (20 mL). The resulting mixture was stirred and refluxed for 6 hours, and then cooled to room temperature. After the mixture was diluted with water (100 mL), the resulting solid was filtered and washed with water and ethyl ether to prepare compound 2-2-2 (19.3 g, yield 57%).

MS [M+H] ⁺ = 389

3) Preparation of compound 2-2-3

Compound 2-2-2 (1.99 g, 5.10 mmol) and sodium-tertiary-butoxide (NaOt-Bu) (0.58 g, 6.01 mmol) and Pd[P(t-Bu) ₃ ] ₂ (51 mg, 2 mol%) was suspended in toluene (50 mL). The resulting mixture was stirred and refluxed for 6 hours, and then cooled to room temperature. Distilled water was added to the reaction solution to complete the reaction, and the organic layer was extracted, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and column with tetrahydrofuran:hexane = 1:5 (v:v) to prepare compound 2-2-3 (0.756 g, yield 42%).

MS [M+H] ⁺ = 353

4) Preparation of compound 2-2-4

After dissolving compound 2-2-3 (12 g, 34 mmol), bis (pinacolato) diboron (12 g, 47 mmol), and potassium acetate (12 g, 118 mmol) in dioxane (150 mL), 50 The temperature was raised to °C, and Pd(dba) ₂ (0.23 g, 0.4 mmol) and P(Cy) ₃ (0.22g, 0.8 mmol) were added, followed by heating and stirring for 12 hours. After cooling the reaction solution to room temperature, distilled water (100 mL) was added and extracted with methylene chloride (100 mL×3). The organic layer was concentrated and recrystallized with ethanol to obtain compound 2-2-4 (14 g, yield 90%).

MS [M+H] ⁺ = 445

5) Preparation of compound 2-2-5

2,7-dibromonaphthalene (20 g, 69.94 mmol) was dissolved in THF (100 mL), and then cooled to -78°C. After slowly adding n-BuLi (2.5 M, 37 mL, 93 mmol) dropwise, the mixture was stirred for 30 minutes. Chlorodiphenylphosphine (17 g, 76 mmol) was slowly added dropwise, stirred for 3 hours, raised to room temperature, water (100 mL) was added, and extracted with THF. The organic layer was concentrated and recrystallized with hexane to obtain compound 2-2-5 (21 g, yield 76.8%).

MS [M+H] ⁺ = 391

6) Preparation of compound 2-2-6

Compound 2-2-6 was obtained in the same manner as in the preparation method of compound 2-1-6, except that compound 2-2-5 was used instead of compound 2-1-5.

MS [M+H] ⁺ = 407

7) Preparation of compound 2-2

Compound 2-2 in the same manner as in the preparation of compound 2-1, except that compound 2-2-4 was used instead of compound 2-1-4 and compound 2-2-6 was used instead of compound 2-1-6. Got it.

MS [M+H] ⁺ = 445

[Example]

Example 1

A glass substrate coated with a thin film of 1,500 Å of ITO (indium tin oxide) was put 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, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl and acetone, followed by drying, the substrate was washed for 5 minutes, and the substrate was transported to a glove box.

On the ITO transparent electrode prepared as described above, a 2 wt% cyclohexanone ink composition containing the following compound A and the following compound E (p dopant) in a weight ratio of 8:2 was spin-coated (4000 rpm) on the ITO surface, and 200 Heat treatment was performed at °C for 30 minutes to form a hole injection layer with a thickness of 40 nm. Thereafter, Compound B was dissolved in toluene at 0.7 wt%, spin-coated on the hole injection layer to form a film at 20 nm, and heated at 200° C. for 30 minutes in a nitrogen atmosphere to form a hole transport layer. On the hole transport layer, a toluene ink composition (0.5 wt% of compound 1-1 concentration 0.5 wt%) in which Compound 1-1 prepared above was mixed with Compound C at a concentration of 8 wt% was spin-coated to form a light emitting layer having a thickness of 20 nm. I did. Compound 2-1 prepared above was vacuum-deposited to a thickness of 35 nm on the emission layer to form an electron injection and electron transport layer. A cathode was formed by sequentially depositing LiF to a thickness of 1 nm and aluminum to a thickness of 100 nm on the electron injection and transport layer.

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

Examples 2 to 10

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound used in Table 1 below was used instead of compound 1-1 or compound 2-1.

Comparative Examples 1 to 7

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound used in Table 1 below was used instead of compound 1-1 or compound 2-1. In Table 1 below, compounds EML A and ETM 1 are as follows.

Table 1 shows the results of measuring the driving voltage, luminous efficiency, external quantum efficiency, luminance and lifetime of the organic light-emitting devices prepared in the above Examples and Comparative Examples at a current density of 10 mA/cm ² . Done. The external quantum efficiency can be calculated as (number of emitted photons)/(number of injected charge carriers), and T95 is a measure of the time to be 95% of the initial luminance at a current density of 10 mA/cm ² .

EML Host ETL Volt(V) cd/A EQE(%) T95(hr) Example 1 Compound 1-1 Compound 2-1 4.42 5.70 5.32 72 Example 2 Compound 1-1 Compound 2-2 4.47 5.62 5.48 75 Example 3 Compound 1-2 Compound 2-1 4.35 5.25 5.11 63 Example 4 Compound 1-3 Compound 2-2 4.47 5.13 5.01 81 Example 5 Compound 1-4 Compound 2-1 4.54 8.51 8.07 58 Example 6 Compound 1-4 Compound 2-2 4.59 8.34 8.11 60 Example 7 Compound 1-5 Compound 2-1 4.18 7.65 6.32 68 Example 8 Compound 1-5 Compound 2-2 4.27 7.32 7.16 77 Example 9 Compound 1-6 Compound 2-2 4.47 7.48 7.21 62 Example 10 Compound 1-7 Compound 2-2 4.56 8.15 7.98 59 Comparative Example 1 Compound 1-1 ETM 1 4.73 4.90 4.33 46 Comparative Example 2 Compound 1-2 ETM 1 4.47 4.63 4.17 52 Comparative Example 3 Compound 1-4 ETM 1 4.41 8.25 8.01 41 Comparative Example 4 Compound 1-6 ETM 1 4.64 7.51 5.09 31 Comparative Example 5 Compound 1-7 ETM 1 4.43 8.16 7.97 38 Comparative Example 6 EML A Compound 2-1 7.90 2.75 2.30 10 Comparative Example 7 EML A Compound 2-2 7.66 2.36 2.11 16

As shown in Table 1, the organic light-emitting device using the compound represented by Formula 1 in the present specification as an emission layer and the compound represented by Formula 2 as an electron transport layer has higher efficiency and longer life than the organic light-emitting device of Comparative Example. And it can be seen that it is applicable to an organic light emitting device.

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

Claims (12)

anode;
Hole transport layer;
Light-emitting layer;
Electron transport layer; And
Including a cathode,
The emission layer includes a compound represented by Formula 1 below,
The electron transport layer comprises a compound represented by the following formula (2),
Organic light emitting element:
[Formula 1]

In Formula 1,
Ar ₁ is substituted or unsubstituted C _6-60 aryl,
Ar ₂ is substituted at the position of *1 or *2, and is -L-Ar ₃ ,
L is a substituted or unsubstituted C _6-60 arylene,
Ar ₃ is substituted or unsubstituted C _6-60 aryl,
R ₁ , R ₂ and R ₃ are each independently hydrogen, deuterium, substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
n1 and n2 are each independently an integer of 1 to 4,
n3 is an integer of 1 to 3,
[Formula 2]

In Chemical Formula 2,
Each A'is independently a benzene ring, a naphthalene ring, or a pyridine ring fused with an adjacent ring,
One of R'is a substituent represented by the following formula (3), and the others are each independently hydrogen; heavy hydrogen; halogen; Nitrile; Nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; A substituted or unsubstituted C _2-60 alkenyl group; Substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heteroaryl including at least one of O, N, Si and S,
[Formula 3]

In Chemical Formula 3,
L'is a single bond; Substituted or unsubstituted C _6-60 arylene; Or a substituted or unsubstituted C _2-60 heteroarylene including at least one of O, N, Si and S,
X'is O, S, or Se,
Ar' ₁ and Ar' ₂ are each independently a substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl including one or more of O, N, Si, and S, or Ar' ₁ , Ar' ₂ , and Ar' ₁ and Ar' ₂ are bonded P with

To form.
The method of claim 1,
Ar ₁ is phenyl or naphthyl, and the phenyl or naphthyl is unsubstituted or substituted with C _1-10 alkyl,
Organic light emitting device.
The method of claim 1,
L is 1,2-phenylene, or 1,3-phenylene,
Organic light emitting device.
The method of claim 1,
Ar ₃ is phenyl, naphthyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, 9-phenyl-9H-carbazolyl, 9,9-dimethyl-9H-c Santenyl, or (naphthyl) anthracenyl,
Organic light emitting device.
The method of claim 1,
Ar ₂ is any one selected from the group consisting of,
Organic light emitting element:

.
The method of claim 1,
the sum of n1 and n2 is 1,
R ₁ and R ₂ are each independently hydrogen, or phenyl, or naphthyl, and the phenyl or naphthyl is unsubstituted or substituted with C _1-10 alkyl,
Organic light emitting device.
The method of claim 1,
R ₃ is hydrogen,
Organic light emitting device.
The method of claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of,
Organic light emitting element:

The method of claim 1,
Are all benzene rings;
One of A'is a pyridine ring and the other is a benzene ring;
One of A'is a naphthalene ring, and the other is a benzene ring; or
Two of A'are naphthalene rings, and the rest are benzene rings,
Organic light emitting device.
The method of claim 1,
L'is phenylene, biphenylylene, naphthylene, phenanthrenylene, anthracenylene, pyridinylene, quinolinylene, or isoquinolinylene,
Organic light emitting device.
The method of claim 1,
Ar' ₁ and Ar' ₂ are each independently phenyl, biphenylyl, or naphthyl; Or Ar' ₁ , Ar' ₂ , and Ar' ₁ and Ar' ₂ with P to which it is bound

To form,
Organic light emitting device.
The method of claim 1,
The compound represented by Formula 2 is any one selected from the group consisting of,
Organic light emitting element:

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