KR20230069021A - 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 including 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 including the same.

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

An organic light emitting device generally has a structure including an anode, a cathode, and an organic material layer between the anode and the cathode. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. In the structure of this 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 when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows.

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

Korean Patent Publication No. 10-2000-0051826

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

The present invention provides a compound represented by Formula 1 below:

[Formula 1]

In Formula 1,

Any one of X ₁ to X ₁₀ is N, the others are CR,

Wherein R is each independently hydrogen, deuterium, or a substituent represented by the following formula (2),

[Formula 2]

In Formula 2,

Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-60 aryl; Or a C _2-60 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted N, O and S, except for biphenylyl substituted with a methoxy group,

L ₁ to L ₃ are each independently a single bond; Substituted or unsubstituted C _6-60 arylene; Or a C _2-60 heteroarylene containing at least one selected from the group consisting of substituted or unsubstituted N, O and S.

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

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

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

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

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

또는

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

or

means a bond connected to another substituent.

In this specification, the term "substituted or unsubstituted" means 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; an alkyl sulfoxy group; aryl sulfoxy group; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; Aralkenyl group; Alkyl aryl group; Alkylamine group; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroaryl group containing one or more of N, O, and S atoms, or substituted or unsubstituted with two or more substituents linked to each other among the substituents exemplified above. . 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 of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a substituent having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with an aryl group having 6 to 25 carbon atoms or a straight-chain, branched-chain or cyclic chain alkyl group having 1 to 25 carbon atoms in the ester group. Specifically, it may be a substituent 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 is preferably 1 to 25 carbon atoms. Specifically, it may be a substituent having the following structure, but is not limited thereto.

In the present specification, the silyl group is specifically 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. but not limited to

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

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

In the present specification, the alkyl group may be straight-chain or branched-chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of 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, etc., but is 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 one 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, etc., but is 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 number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, 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 heteroaryl group is a heteroaryl group containing one or more of O, N, Si, and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. According to one embodiment, the heteroaryl group has 6 to 30 carbon atoms. According to one embodiment, the carbon number of the heteroaryl group is 6 to 20. Examples of the heteroaryl 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, and an acridyl group. , pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl 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, thiadia A zolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.

In the present specification, an aralkyl group, an aralkenyl group, an alkylaryl group, and an aryl group among arylamine groups are the same as the examples 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 examples of the above-mentioned alkyl group. In the present specification, the description of the heteroaryl group described above may be applied to the heteroaryl of the heteroarylamine. In the present specification, the alkenyl group among the aralkenyl groups is the same as the examples 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 heteroaryl group described above 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 aryl group or cycloalkyl group described above may be applied, except that the hydrocarbon ring is formed by combining two substituents. In the present specification, heteroaryl is not a monovalent group, and the description of the above-described heteroaryl group may be applied, except that it is formed by combining two substituents.

Preferably, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1 to 1-10:

In Formulas 1-1 to 1-10,

R is as defined in Formula 1 above.

Preferably, in Formula 1, one of R is a substituent represented by Formula 2, and the others may be hydrogen or deuterium. More preferably, any one of R is a substituent represented by Formula 2, and the others may be hydrogen.

Preferably, Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-30 aryl; Or it may be a C _2-30 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted N, O, and S, except for biphenylyl substituted with a methoxy group. More preferably, Ar ₁ and Ar ₂ are each independently selected from phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, di It may be benzofuranyl, dibenzothiophenyl, or phenyl carbazolyl, and Ar ₁ and Ar ₂ may be unsubstituted or substituted with one or more deuterium atoms. Most preferably, Ar ₁ and Ar ₂ may each independently be any one selected from the group consisting of:

.

.

Preferably, L ₁ to L ₃ are each independently a single bond; Substituted or unsubstituted C _6-20 arylene; Or it may be a C _2-20 heteroarylene containing at least one selected from the group consisting of substituted or unsubstituted N, O and S. More preferably, L ₁ to L ₃ may each independently be a single bond, phenylene, naphthalenediyl, dimethylfluorenediyl, diphenylfluorenediyl, or carbazolediyl, wherein L ₁ to L ₃ are phenyl In the case of rene, naphthalenediyl, dimethylfluorenediyl, diphenylfluorenediyl, or carbazolediyl, L ₁ to L ₃ may be unsubstituted or substituted with one or more deuterium atoms. Most preferably, L ₁ to L ₃ may each independently be a single bond or any one selected from the group consisting of:

.

.

Preferably, L ₁ may be a single bond or phenylene which is unsubstituted or substituted with one or more deuterium atoms.

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

.

.

Among the compounds represented by Formula 1, when X ₁ is N, X ₂ is a substituent represented by Formula 2, X ₃ to X ₁₀ are CR, and L ₁ is not a single bond, for example, as shown in Scheme 1 below: It can be prepared by a manufacturing method, X ₁ is N, X ₂ is a substituent represented by Formula 2, X ₃ to X ₁₀ are CR, and L ₁ is a single bond, for example, as shown in Scheme 2 below method, and other compounds can be similarly prepared.

[Scheme 1]

[Scheme 2]

In Schemes 1 and 2, R, L ₂ , L ₃ , Ar ₁ and Ar ₂ are as defined in Formula 1, Z ₁ and Z ₂ are independently halogen, preferably Z ₁ and Z ₂ are each independently chloro or bromo.

Scheme 1 is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and a reactor for the Suzuki coupling reaction may be modified as known in the art. In addition, Reaction Scheme 2 is an amine substitution reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction may be modified as known in the art. The manufacturing method may be more specific in Preparation Examples to be described later.

In addition, the present invention provides an organic light emitting device including 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 one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Chemical Formula 1. do.

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

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

In addition, the organic material layer may include a hole transport layer, a hole injection layer, a layer that simultaneously transports and injects holes, or an electron blocking layer, and the hole transport layer, the hole injection layer, and a layer that simultaneously transports and injects holes Alternatively, the electron blocking layer may include the compound represented by Formula 1 above. Preferably, the hole transport layer, the hole injection layer, or the electron blocking layer may include the compound represented by Chemical Formula 1. More preferably, the electron blocking layer may include the compound represented by Formula 1 above.

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

1 shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a light emitting layer 3 and a cathode 4. 2 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, a hole blocking layer 8, an electron injection and transport layer ( 9) and an example of an organic light emitting element composed of a cathode 4 is shown. In such a structure, the compound represented by Formula 1 may be included in the hole injection layer, the hole transport layer, the electron blocking layer, or the light emitting layer. Preferably, the compound represented by Formula 1 may be included in the hole injection layer, the hole transport layer, or the electron blocking layer. More preferably, the compound represented by Chemical Formula 1 may be included in the electron blocking 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 of the organic layers includes the compound represented by Chemical Formula 1. 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 device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, depositing a metal or a metal oxide having conductivity or an alloy thereof on the substrate to form an anode And, after forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound represented by Chemical Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

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

In one example, the first electrode is an anode and 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 high work function is generally preferred so that holes can be smoothly injected into the organic 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; 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 so as to easily inject electrons 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; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material has the ability to transport holes and has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and generated in the light emitting layer A compound that prevents migration of excitons to the electron injecting layer or electron injecting material and has excellent thin film formation ability is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrins, oligothiophenes, arylamine-based organic materials, hexanitrilehexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene-based organic materials. of organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. As a hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer is a material having high hole mobility. this is suitable Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.

The electron blocking layer is a layer placed between the hole transport layer and the light emitting layer to prevent electrons injected from the cathode from passing to the hole transport layer without recombination in the light emitting layer, and is also called an electron blocking layer. A material having a smaller electron affinity than the electron transport layer is preferable for the electron blocking layer. Preferably, the compound represented by Chemical Formula 1 may be included as a material for the electron blocking layer.

The light emitting material is a material capable of emitting light in the visible ray region by receiving 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-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; Polyfluorene, rubrene, etc., but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a compound containing a hetero ring. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, periplanthene, etc. having an arylamino group, and styrylamine compounds include substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, wherein 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, etc., but is not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes and platinum complexes. For example, one or more selected from the following group may be used as a dopant material, but is not limited thereto:

.

.

The hole blocking layer is a layer placed between the electron transport layer and the light emitting layer to prevent holes injected from the anode from being recombinated in the light emitting layer and passing to the electron transport layer, and is also called a hole blocking layer. A material having high ionization energy is preferred for the hole-blocking layer.

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

The electron injection layer is a layer for injecting electrons from an electrode, has the ability to transport electrons, has an excellent electron injection effect from a cathode, an excellent electron injection effect for a light emitting layer or a light emitting material, and injects holes of excitons generated in the light emitting layer. A compound that prevents migration to a layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preonylidene methane, anthrone, etc. 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 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)( There are o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium. Not limited to this.

On the other hand, in the present invention, the "electron injection and transport layer" is a layer that performs both the roles of the electron injection layer and the electron transport layer, and materials that play the role of each layer may be used alone or in combination, but are limited thereto. It doesn't work.

The organic light emitting device according to the present invention may be a bottom emission device, a top emission device, or a double-sided light emitting device, and in particular, may be a bottom emission device requiring relatively high light emitting efficiency.

In addition, the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

Preparation of the compound represented by Formula 1 and the organic light emitting device including the same will be described in detail in the following Synthesis Examples and Examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

Preparation Example 1

5-bromo-2-chloropyridin-4-amine (15 g, 72.3 mmol) and (2-methoxynaphthalen-1-yl)boronic acid (15.3 g, 75.9 mmol) were added to 300 ml of THF and stirred and refluxed. Thereafter, potassium carbonate (30 g, 216.9 mmol) was dissolved in 100 ml of water, and after sufficiently stirred, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14 g of Compound A-1-1_P1. (Yield 68%, MS: [M+H] ⁺ = 285)

Compound A-1-1_P1 (15 g, 52.7 mmol) and HBF ₄ (9.3 g, 105.4 mmol) were added to 150 ml of Acetonitrile and stirred. Thereafter, NaNO ₂ (14.6 g, 105.4 mmol) was dissolved in 30 ml of water and added slowly at 0 °C. After reacting for 8 hours, the temperature was raised to room temperature, and diluted with 300 ml of water. After dissolving in chloroform and washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.9 g of Compound A-1-1. (Yield 52%, MS: [M+H] ⁺ = 254)

Preparation Example 2

4-bromopyridin-3-amine (15 g, 86.7 mmol) and (4-chloro-2-methoxynaphthalen-1-yl)boronic acid (21.5 g, 91 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (35.9 g, 260.1 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.9 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.5 g of compound A-2-4_P1. (Yield 67%, MS: [M+H] ⁺ = 285)

Compound A-2-4_P1 (15 g, 52.7 mmol) and HBF ₄ (9.3 g, 105.4 mmol) were added to 150 ml of Acetonitrile and stirred. Thereafter, NaNO ₂ (14.6 g, 105.4 mmol) was dissolved in 30 ml of water and added slowly at 0 °C. After reacting for 10 hours, the temperature was raised to room temperature, and diluted with 300 ml of water. After dissolving in chloroform and washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.7 g of Compound A-2-4. (Yield 50%, MS: [M+H] ⁺ = 254)

Preparation Example 3

3-bromopyridin-2-amine (15 g, 86.7 mmol) and (5-chloro-2-methoxynaphthalen-1-yl)boronic acid (21.5 g, 91 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (35.9 g, 260.1 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.9 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic layer and the water layer were separated, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.7 g of compound A-3-5_P1. (Yield 72%, MS: [M+H] ⁺ = 285)

Compound A-3-5_P1 (15 g, 52.7 mmol) and HBF ₄ (9.3 g, 105.4 mmol) were added to 150 ml of Acetonitrile and stirred. Thereafter, NaNO ₂ (14.6 g, 105.4 mmol) was dissolved in 30 ml of water and added slowly at 0 °C. After reacting for 9 hours, the temperature was raised to room temperature, and diluted with 300 ml of water. After dissolving in chloroform and washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.1 g of Compound A-3-5. (Yield 53%, MS: [M+H] ⁺ = 254)

Production Example 4

2-bromopyridin-3-amine (15 g, 86.7 mmol) and (5-chloro-2-methoxynaphthalen-1-yl)boronic acid (21.5 g, 91 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (35.9 g, 260.1 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.9 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic layer and the water layer were separated, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.2 g of compound A-4-6_P1. (Yield 70%, MS: [M+H] ⁺ = 285)

Compound A-4-6_P1 (15 g, 52.7 mmol) and HBF ₄ (9.3 g, 105.4 mmol) were added to 150 ml of Acetonitrile and stirred. Thereafter, NaNO ₂ (14.6 g, 105.4 mmol) was dissolved in 30 ml of water and added slowly at 0 °C. After reacting for 10 hours, the temperature was raised to room temperature, and diluted with 300 ml of water. After dissolving in chloroform and washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.7 g of compound A-4-6. (Yield 73%, MS: [M+H] ⁺ = 254)

Preparation Example 5

2-bromo-6-chloroaniline (15 g, 72.6 mmol) and (3-methoxyisoquinolin-4-yl)boronic acid (15.5 g, 76.3 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (30.1 g, 217.9 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.8 g of Compound A-5-3_P1. (Yield 67%, MS: [M+H] ⁺ = 285)

Compound A-5-3_P1 (15 g, 52.7 mmol) and HBF ₄ (9.3 g, 105.4 mmol) were added to 150 ml of Acetonitrile and stirred. Thereafter, NaNO ₂ (14.6 g, 105.4 mmol) was dissolved in 30 ml of water and added slowly at 0 °C. After reacting for 10 hours, the temperature was raised to room temperature, and diluted with 300 ml of water. After dissolving in chloroform and washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.3 g of compound A-5-3. (Yield 62%, MS: [M+H] ⁺ = 254)

Preparation Example 6

2-bromoaniline (15 g, 87.2 mmol) and (7-chloro-3-methoxyquinolin-4-yl)boronic acid (21.7 g, 91.5 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (36.2 g, 261.6 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.9 mmol) was added. After reacting for 3 hours, the reaction mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.6 g of compound A-6-6_P1. (Yield 75%, MS: [M+H] ⁺ = 285)

Compound A-6-6_P1 (15 g, 52.7 mmol) and HBF ₄ (9.3 g, 105.4 mmol) were added to 150 ml of Acetonitrile and stirred. Thereafter, NaNO ₂ (14.6 g, 105.4 mmol) was dissolved in 30 ml of water and added slowly at 0 °C. After reacting for 8 hours, the temperature was raised to room temperature, and diluted with 300 ml of water. After dissolving in chloroform and washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.7 g of compound A-6-6. (Yield 58%, MS: [M+H] ⁺ = 254)

Preparation Example 7

2-bromoaniline (15 g, 87.2 mmol) and (7-chloro-6-methoxyquinolin-5-yl)boronic acid (21.7 g, 91.5 mmol) were added to 300 ml of THF and stirred and refluxed. Thereafter, potassium carbonate (36.2 g, 261.6 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.9 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18.1 g of Compound A-7-4_P1. (Yield 73%, MS: [M+H] ⁺ = 285)

Compound A-7-4_P1 (15 g, 52.7 mmol) and HBF ₄ (9.3 g, 105.4 mmol) were added to 150 ml of Acetonitrile and stirred. Thereafter, NaNO ₂ (14.6 g, 105.4 mmol) was dissolved in 30 ml of water and added slowly at 0 °C. After reacting for 10 hours, the temperature was raised to room temperature, and diluted with 300 ml of water. After dissolving in chloroform and washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.9 g of Compound A-7-4. (Yield 59%, MS: [M+H] ⁺ = 254)

Preparation Example 8

2-bromoaniline (15 g, 87.2 mmol) and (3-chloro-6-methoxyisoquinolin-5-yl)boronic acid (21.7 g, 91.5 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (36.2 g, 261.6 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.9 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18.3 g of compound A-8-7_P1. (Yield 74%, MS: [M+H] ⁺ = 285)

Compound A-8-7_P1 (15 g, 52.7 mmol) and HBF ₄ (9.3 g, 105.4 mmol) were added to 150 ml of Acetonitrile and stirred. Thereafter, NaNO ₂ (14.6 g, 105.4 mmol) was dissolved in 30 ml of water and added slowly at 0 °C. After reacting for 8 hours, the temperature was raised to room temperature, and diluted with 300 ml of water. After dissolving in chloroform and washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 6.7 g of Compound A-8-7. (Yield 50%, MS: [M+H] ⁺ = 254)

Preparation Example 9

2-bromo-4-chloroaniline (15 g, 72.6 mmol) and (7-methoxyisoquinolin-8-yl)boronic acid (15.5 g, 76.3 mmol) were added to 300 ml of THF and stirred and refluxed. Thereafter, potassium carbonate (30.1 g, 217.9 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.2 g of Compound A-9-1_P1. (Yield 69%, MS: [M+H] ⁺ = 285)

Compound A-9-1_P1 (15 g, 52.7 mmol) and HBF ₄ (9.3 g, 105.4 mmol) were added to 150 ml of Acetonitrile and stirred. Thereafter, NaNO ₂ (14.6 g, 105.4 mmol) was dissolved in 30 ml of water and added slowly at 0 °C. After reacting for 10 hours, the temperature was raised to room temperature, and diluted with 300 ml of water. After dissolving in chloroform and washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.9 g of Compound A-9-1. (Yield 74%, MS: [M+H] ⁺ = 254)

Preparation Example 10

2-bromoaniline (15 g, 87.2 mmol) and (5-chloro-7-methoxyquinolin-8-yl)boronic acid (21.7 g, 91.5 mmol) were added to 300 ml of THF and stirred and refluxed. Thereafter, potassium carbonate (36.2 g, 261.6 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.9 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic layer and the water layer were separated, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.1 g of compound A-10-5_P1. (Yield 73%, MS: [M+H] ⁺ = 285)

Compound A-10-5_P1 (15 g, 52.7 mmol) and HBF ₄ (9.3 g, 105.4 mmol) were added to 150 ml of Acetonitrile and stirred. Thereafter, NaNO ₂ (14.6 g, 105.4 mmol) was dissolved in 30 ml of water and added slowly at 0 °C. After reacting for 8 hours, the temperature was raised to room temperature, and diluted with 300 ml of water. After dissolving in chloroform and washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.4 g of compound A-10-5. (Yield 63%, MS: [M+H] ⁺ = 254)

Precursor materials other than the precursor compounds synthesized in Preparation Examples 1 to 10 were obtained by synthesizing in the same manner as above, but using different intermediates. Each of the obtained precursor materials was used to prepare compounds in Synthesis Examples to be described later.

Synthesis Example 1

Compound A-4-8 (15 g, 59.1 mmol) and compound amine1 (32.5 g, 62.1 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (24.5 g, 177.3 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 25.8 g of Compound 1. (Yield 71%, MS: [M+H] ⁺ = 615)

Synthesis Example 2

In a nitrogen atmosphere, compound A-4-3 (15 g, 59.1 mmol), compound amine2 (18.3 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.6 g of Compound 2. (Yield 68%, MS: [M+H] ⁺ = 513)

Synthesis Example 3

In a nitrogen atmosphere, compound A-4-1 (15 g, 59.1 mmol), compound amine3 (22.4 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 23.6 g of Compound 3. (Yield 69%, MS: [M+H] ⁺ = 579)

Synthesis Example 4

In a nitrogen atmosphere, compound A-1-3 (15 g, 59.1 mmol), compound amine4 (22.4 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.9 g of Compound 4. (Yield 61%, MS: [M+H] ⁺ = 579)

Synthesis Example 5

In a nitrogen atmosphere, compound A-1-1 (15 g, 59.1 mmol), compound amine5 (20 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 21 g of Compound 5. (Yield 66%, MS: [M+H] ⁺ = 539)

Synthesis Example 6

In a nitrogen atmosphere, compound A-1-5 (15 g, 59.1 mmol), compound amine6 (23.7 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 24.8 g of Compound 6. (Yield 70%, MS: [M+H] ⁺ = 599)

Synthesis Example 7

In a nitrogen atmosphere, compound A-2-7 (15 g, 59.1 mmol), compound amine7 (21.7 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 24.8 g of Compound 7. (Yield 74%, MS: [M+H] ⁺ = 567)

Synthesis Example 8

In a nitrogen atmosphere, compound A-2-7 (15 g, 59.1 mmol), compound amine8 (25.5 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 26.7 g of Compound 8. (Yield 72%, MS: [M+H] ⁺ = 628)

Synthesis Example 9

Compound A-2-5 (15 g, 59.1 mmol) and compound amine9 (30.9 g, 62.1 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (24.5 g, 177.3 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic layer and the water layer were separated, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 26.1 g of Compound 9. (Yield 75%, MS: [M+H] ⁺ = 589)

Synthesis Example 10

In a nitrogen atmosphere, compound A-2-2 (15 g, 59.1 mmol), compound amine10 (23.1 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 21.9 g of Compound 10. (Yield 63%, MS: [M+H] ⁺ = 589)

Synthesis Example 11

In a nitrogen atmosphere, compound A-2-1 (15 g, 59.1 mmol), compound amine11 (24.7 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 26.1 g of Compound 11. (Yield 72%, MS: [M+H] ⁺ = 615)

Synthesis Example 12

In a nitrogen atmosphere, compound A-3-7 (15 g, 59.1 mmol), compound amine12 (20.8 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 24.5 g of Compound 12. (Yield 75%, MS: [M+H] ⁺ = 553)

Synthesis Example 13

In a nitrogen atmosphere, compound A-3-8 (15 g, 59.1 mmol), compound amine13 (24.7 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 22.5 g of Compound 13. (Yield 62%, MS: [M+H] ⁺ = 615)

Synthesis Example 14

In a nitrogen atmosphere, compound A-5-2 (15 g, 59.1 mmol), compound amine14 (25.5 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 22.7 g of Compound 14. (Yield 61%, MS: [M+H] ⁺ = 629)

Synthesis Example 15

Compound A-5-7 (15 g, 59.1 mmol) and compound amine15 (34.4 g, 62.1 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (24.5 g, 177.3 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 24 g of Compound 15. (Yield 63%, MS: [M+H] ⁺ = 645)

Synthesis Example 16

In a nitrogen atmosphere, compound A-6-2 (15 g, 59.1 mmol), compound amine16 (30.1 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 29.1 g of Compound 16. (Yield 70%, MS: [M+H] ⁺ = 703)

Synthesis Example 17

In a nitrogen atmosphere, compound A-6-7 (15 g, 59.1 mmol), compound amine17 (24.7 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 22.9 g of Compound 17. (Yield 63%, MS: [M+H] ⁺ = 615)

Synthesis Example 18

Compound A-7-2 (15 g, 59.1 mmol) and compound amine18 (30.9 g, 62.1 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (24.5 g, 177.3 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 21.6 g of Compound 18. (Yield 62%, MS: [M+H] ⁺ = 589)

Synthesis Example 19

In a nitrogen atmosphere, compound A-7-4 (15 g, 59.1 mmol), compound amine19 (22.7 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 23.1 g of Compound 19. (Yield 67%, MS: [M+H] ⁺ = 583)

Synthesis Example 20

In a nitrogen atmosphere, compound A-7-1 (15 g, 59.1 mmol), compound amine20 (23.1 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 24.7 g of compound 20. (Yield 71%, MS: [M+H] ⁺ = 589)

Synthesis Example 21

In a nitrogen atmosphere, compound A-8-1 (15 g, 59.1 mmol), compound amine21 (26.2 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 28.3 g of Compound 21. (Yield 75%, MS: [M+H] ⁺ = 639)

Synthesis Example 22

In a nitrogen atmosphere, compound A-8-5 (15 g, 59.1 mmol), compound amine22 (30.1 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 31.1 g of compound 22. (Yield 75%, MS: [M+H] ⁺ = 703)

Synthesis Example 23

Compound A-9-1 (15 g, 59.1 mmol) and compound amine23 (29.6 g, 62.1 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (24.5 g, 177.3 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, and an organic layer and an aqueous layer were separated, and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 24.1 g of compound 23. (Yield 73%, MS: [M+H] ⁺ = 559)

Synthesis Example 24

In a nitrogen atmosphere, compound A-9-5 (15 g, 59.1 mmol), compound amine24 (30 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 28.2 g of compound 24. (Yield 68%, MS: [M+H] ⁺ = 701)

Synthesis Example 25

Compound A-9-4 (15 g, 59.1 mmol) and compound amine25 (27.8 g, 62.1 mmol) were added to 300 ml of THF, stirred and refluxed. Thereafter, potassium carbonate (24.5 g, 177.3 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic layer was distilled after separating the organic layer and the water layer. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 23.9 g of compound 25. (Yield 75%, MS: [M+H] ⁺ = 539)

Synthesis Example 26

In a nitrogen atmosphere, compound A-10-2 (15 g, 59.1 mmol), compound amine26 (20 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.4 g of compound 26. (Yield 64%, MS: [M+H] ⁺ = 539)

Synthesis Example 27

In a nitrogen atmosphere, compound A-10-7 (15 g, 59.1 mmol), compound amine27 (21.4 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 23.9 g of compound 27. (Yield 72%, MS: [M+H] ⁺ = 563)

Synthesis Example 28

In a nitrogen atmosphere, compound A-10-8 (15 g, 59.1 mmol), compound amine28 (26.5 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 24 g of compound 28. (Yield 63%, MS: [M+H] ⁺ = 645)

Synthesis Example 29

In a nitrogen atmosphere, compound A-10-5 (15 g, 59.1 mmol), compound amine29 (25.5 g, 62.1 mmol), and sodium tert-butoxide (7.4 g, 76.8 mmol) were added to 300 ml of xylene, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Thereafter, the compound was completely dissolved again in chloroform, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 24.1 g of compound 29. (Yield 65%, MS: [M+H] ⁺ = 628)

Example 1

A glass substrate coated with ITO (indium tin oxide) to a thickness of 1000 Å was put in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a Fischer Co. product was used as the detergent, and distilled water filtered through a second filter of a Millipore Co. product was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum deposition machine.

The following compound HI-1 was formed to a thickness of 1150 Å as a hole injection layer on the prepared ITO transparent electrode, but the following compound A-1 was p-doped at a concentration of 1.5% by weight. The following compound HT-1 was vacuum deposited on the hole injection layer to form a hole transport layer having a thickness of 800 Å. Subsequently, an electron blocking layer was formed on the hole transport layer by vacuum depositing the previously prepared Compound 1 to a film thickness of 150 Å. Subsequently, the following compound RH-1 as a host and the following compound Dp-7 as a dopant were vacuum deposited on the compound 1 at a weight ratio of 98:2 to form a red light emitting layer having a thickness of 400 Å. A hole blocking layer was formed on the light emitting layer by vacuum depositing the following compound HB-1 to a film thickness of 30 Å. Subsequently, the following ET-1 compound and the following LiQ compound were vacuum deposited at a weight ratio of 2:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300 Å. A negative electrode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1000 Å on the electron injection and transport layer.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 Å/sec, the deposition rate of lithium fluoride on the anode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum level during deposition was 2 * 10 Maintaining ^-7 to 5 * 10 ^-6 torr, an organic light emitting device was fabricated.

Examples 2 to 29

An organic light emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in the organic light emitting device of Example 1.

Comparative Examples 1 to 6

An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in the organic light emitting device of Example 1. The structures of compounds C-1 to C-6 in Table 1 are as follows.

Experimental Example

When current was applied to the organic light emitting devices prepared in Examples 1 to 29 and Comparative Examples 1 to 6, voltage and efficiency were measured (15 mA/cm ² ), and the results are shown in Table 1 below. . The lifetime T95 means the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.

division matter Driving voltage (V) Efficiency (cd/A) Lifetime T95(hr) luminescent color Example 1 compound 1 3.68 19.08 141 Red Example 2 compound 2 3.72 19.44 155 Red Example 3 compound 3 3.76 19.23 148 Red Example 4 compound 4 3.46 19.82 186 Red Example 5 compound 5 3.40 20.20 176 Red Example 6 compound 6 3.41 20.30 184 Red Example 7 compound 7 3.40 21.35 174 Red Example 8 compound 8 3.39 21.55 170 Red Example 9 compound 9 3.42 22.28 173 Red Example 10 compound 10 3.42 21.71 185 Red Example 11 compound 11 3.46 21.29 180 Red Example 12 compound 12 3.57 21.18 161 Red Example 13 compound 13 3.55 20.79 174 Red Example 14 compound 14 3.64 20.00 164 Red Example 15 compound 15 3.61 20.39 150 Red Example 16 compound 16 3.64 19.43 155 Red Example 17 compound 17 3.65 19.79 141 Red Example 18 compound 18 3.46 19.75 190 Red Example 19 compound 19 3.47 20.08 182 Red Example 20 compound 20 3.47 19.80 172 Red Example 21 compound 21 3.43 22.09 178 Red Example 22 compound 22 3.43 21.22 189 Red Example 23 compound 23 3.67 19.18 154 Red Example 24 compound 24 3.68 19.10 143 Red Example 25 compound 25 3.80 19.30 151 Red Example 26 compound 26 3.67 19.44 147 Red Example 27 compound 27 3.56 19.96 150 Red Example 28 compound 28 3.65 20.20 152 Red Example 29 compound 29 3.55 20.13 146 Red Comparative Example 1 compound C-1 4.31 8.93 23 Red Comparative Example 2 compound C-2 3.91 17.68 108 Red Comparative Example 3 compound C-3 3.84 18.23 126 Red Comparative Example 4 compound C-4 3.97 17.14 101 Red Comparative Example 5 compound C-5 4.13 14.65 64 Red Comparative Example 6 compound C-6 4.22 14.32 52 Red

When current was applied to the organic light emitting devices manufactured in Examples 1 to 29 and Comparative Examples 1 to 6, the results shown in Table 1 were obtained. A conventionally widely used material was used as a constituent material of the red organic light emitting device of Example 1, and the compound Dp-7 was used as a dopant of the red light emitting layer.

In Comparative Examples 1 to 6, organic light emitting diodes were prepared using C-1 to C-6 instead of Compound 1. Looking at the results of Table 1, when the compound of the present invention was used as an electron blocking layer, the driving voltage was lowered compared to the comparative example material, and the efficiency was also increased, indicating that energy transfer from the host to the red dopant was well achieved. Could know. In addition, it was found that the lifetime characteristics can be greatly improved while maintaining high efficiency. This can eventually be determined because the compound of the present invention has higher electron and hole stability than the comparative example compound.

In conclusion, it was confirmed that the driving voltage, luminous efficiency and lifetime characteristics of the organic light emitting device can be improved when the compound of the present invention is used as an electron blocking layer of the red light emitting layer.

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

Claims (10)

A compound represented by Formula 1 below:
[Formula 1]

In Formula 1,
Any one of X ₁ to X ₁₀ is N, the others are CR,
Wherein R is each independently hydrogen, deuterium, or a substituent represented by the following formula (2),
[Formula 2]

In Formula 2,
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-60 aryl; Or a C _2-60 heteroaryl containing at least one selected from the group consisting of substituted or unsubstituted N, O and S, except for biphenylyl substituted with a methoxy group,
L ₁ to L ₃ are each independently a single bond; Substituted or unsubstituted C _6-60 arylene; Or a C _2-60 heteroarylene containing at least one selected from the group consisting of substituted or unsubstituted N, O and S.
According to claim 1,
Any one of R is a substituent represented by Formula 2, and the others are hydrogen or deuterium,
compound.
According to claim 1,
Ar ₁ and Ar ₂ are each independently selected from phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, dibenzofuranyl, di benzothiophenyl, or phenyl carbazolyl;
Wherein Ar ₁ and Ar ₂ are unsubstituted or substituted with one or more deuterium,
compound.
According to claim 1,
Ar ₁ and Ar ₂ are each independently any one selected from the group consisting of
compound:

.
According to claim 1,
L ₁ to L ₃ are each independently a single bond, phenylene, naphthalenediyl, dimethylfluorenediyl, diphenylfluorenediyl, or carbazoldiyl;
When L ₁ to L ₃ are phenylene, naphthalenediyl, dimethylfluorenediyl, diphenylfluorenediyl, or carbazolediyl, L ₁ to L ₃ are unsubstituted or substituted with one or more deuterium,
compound.
According to claim 1,
L ₁ to L ₃ are each independently a single bond, or any one selected from the group consisting of
compound:

.
According to claim 1,
L ₁ is a single bond or phenylene unsubstituted or substituted with one or more deuterium atoms;
compound.
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of
compound:

.
a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound according to any one of claims 1 to 8. doing,
organic light emitting device.
According to claim 9,
The organic material layer is a hole injection layer, a hole transport layer, or an electron blocking layer,
organic light emitting device.

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