KR20230076982A - Organic compound and electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to a compound represented by chemical formula 1, and an organic light emitting device comprising the same, wherein the compound is employed in an optical efficiency improvement layer provided in an organic light emitting device, and can implement light emitting properties such as low voltage driving of the device, excellent color purity, and light emitting efficiency.

Description

Organic compound and organic light emitting device comprising the same {Organic compound and electroluminescent device comprising the same}

The present invention relates to an organic light-emitting device characterized in that it is employed as a material for a capping layer provided in an organic light-emitting device, and an organic light-emitting device having significantly improved light-emitting characteristics such as low-voltage driving and excellent light-emitting efficiency by employing the organic compound. will be.

Organic light emitting devices can not only be formed on a transparent substrate, but also can be driven at a low voltage of 10 V or less compared to plasma display panels or inorganic electroluminescent (EL) displays, and consume relatively little power. , It has the advantage of being excellent in color, and can show three colors of green, blue, and red, so it has recently become a subject of much interest as a next-generation display device.

However, in order for the organic light emitting device to exhibit the above characteristics, the materials constituting the organic layer in the device, such as hole injection materials, hole transport materials, light emitting materials, electron transport materials, and electron injection materials, are supported by stable and efficient materials. However, the development of stable and efficient organic layer materials for organic light emitting devices has not yet been sufficiently accomplished.

Therefore, in order to implement a more stable organic light emitting device, and to achieve high efficiency, long lifespan, and large size of the device, further improvement in terms of efficiency and lifespan characteristics is required, and in particular, development of materials forming each organic layer of the organic light emitting device is required. It is desperately needed.

In addition, recently, research on improving the characteristics of an organic light emitting device by changing the performance of each organic layer material, as well as technology for improving color purity and increasing luminous efficiency by optimizing optical thickness between an anode and a cathode, has been conducted. It is considered as one of the important factors to improve performance, and as an example of this method, a capping layer is used on an electrode to increase light efficiency and achieve excellent color purity.

Therefore, the present invention provides a novel organic compound capable of realizing excellent light emitting characteristics such as low-voltage driving and improved luminous efficiency by being employed in a light efficiency improvement layer (capping layer) provided in an organic light emitting device and an organic light emitting device including the same. want to provide

In order to solve the above problems, the present invention provides an organic compound having a structure represented by the following [Chemical Formula I].

[Formula I]

The characteristic structure of [Formula 1] and the specific compounds, Ar ₁ to Ar ₂ and L according to the present invention realized thereby will be described later.

In addition, the present invention is an organic light emitting device including a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein the upper or lower portions of the first electrode and the second electrode are provided. Further comprising a light efficiency improving layer (capping layer) formed on at least one side opposite to the organic layer, wherein the light efficiency improving layer provides an organic light emitting device including the organic compound represented by the [Chemical Formula I].

The organic compound according to the present invention is employed as a light efficiency improvement layer material provided in an organic light emitting device, and can realize improved light emitting characteristics such as low voltage driving of the organic light emitting device, excellent light emitting efficiency, and color purity, and thus can be used in various display devices as well as lighting devices. can be useful

Hereinafter, the present invention will be described in more detail.

The present invention relates to an organic compound characterized in that it is represented by the following [Formula I], which is employed as a material for a light efficiency improvement layer provided in an organic light emitting device and can obtain light emitting characteristics such as low voltage driving of the device and excellent light emitting efficiency and color purity. will be.

[Formula I]

In the above [Formula I],

L is each independently a direct bond or is selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, n is an integer of 0 to 3, wherein n When is 2 or more, a plurality of L's are the same as or different from each other.

Ar ₁ and Ar ₂ are the same as or different from each other, and are each independently deuterium (D), a cyano group (CN), a halogen group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. Alkoxy group, substituted or unsubstituted halogenated alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted halogenated alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and a substituted or unsubstituted amine group.

Meanwhile, 'substituted or unsubstituted' in the definition of L, Ar ₁ and Ar ₂ means that L, Ar ₁ and Ar ₂ are deuterium, halogen group, cyano group, alkyl group, halogenated alkyl group, deuterium, respectively. It is substituted with one or two or more substituents selected from an alkyl group, a cycloalkyl group, a heterocycloalkyl group, an alkoxy group, a halogenated alkoxy group, a deuterated alkoxy group, an aryl group, a heteroaryl group, an alkylsilyl group, an arylsilyl group, and a carbonyl group, It means that two or more substituents among the above substituents are substituted with linked substituents or do not have any substituents.

For example, a substituted aryl group refers to a phenyl group, a biphenyl group, a naphthalene group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a perylene group, a tetracenyl group, an anthracenyl group, etc. means it has been

In addition, the substituted heteroaryl group refers to a pyridyl group, a thiophenyl group, a triazine group, a quinoline group, a phenanthroline group, an imidazole group, a thiazole group, an oxazole group, a carbazole group, and condensed heterocyclic groups thereof, such as a benzquinoline group. , It means that a benzimidazole group, a benzoxazole group, a benzthiazole group, a benzcarbazole group, a dibenzothiophenyl group, a dibenzofuran group, etc. are substituted with the above substituents.

In the present invention, examples of the substituents will be described in detail below, but are not limited thereto.

In the present invention, the alkyl group may be a straight chain or branched chain, and specific examples include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group , sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1 -Methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentyl group methyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, etc., but is not limited thereto.

In the present invention, the alkoxy group may be straight chain or branched chain. Specifically, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, i-propyloxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group , Neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group , benzyloxy group, p-methylbenzyloxy group, etc., but is not limited thereto.

In the present invention, the alkyl group or alkoxy group may be a deuterated alkyl group or alkoxy group, a halogenated alkyl group, or an alkoxy group substituted with deuterium or a halogen group.

In the present invention, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 30, and also includes a polycyclic aryl group structure in which cycloalkyl or the like is fused, and a monocyclic aryl group Examples of include a phenyl group, a biphenyl group, a terphenyl group, a stilbene group, and the like, and examples of the polycyclic aryl group include a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a tetracenyl group, and a chrysenyl group. , fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthrene group, etc., but the scope of the present invention is not limited only to these examples.

,

,

등이 있다.In the present invention, the fluorenyl group is a structure in which two ring organic compounds are linked through one atom, for example

,

,

etc.

,

등이 있다.In the present invention, the fluorenyl group includes the structure of an open fluorenyl group, where the open fluorenyl group is a structure in which one ring compound is disconnected from a structure in which two ring organic compounds are connected through one atom. , for example

,

etc.

,

,

,

등이 있다.In addition, the carbon atom of the ring may be substituted with any one or more heteroatoms selected from N, S and O, for example

,

,

,

etc.

In the present invention, the heteroaryl group is a heterocyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but preferably has 3 to 30 carbon atoms, and is a polycyclic group in which cycloalkyl or heterocycloalkyl is fused. It includes a heteroaryl group structure, and specific examples thereof in the present invention 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, and a bipyridyl group. , pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, Dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, phenoxazinyl group, phenothiazine group, etc., but only these It is not limited.

In the present invention, the amine group may be -NH ₂ , an alkylamine group, an arylamine group, a heteroarylamine group, an arylheteroarylamine group, and the like, and the aryl (heteroaryl)amine group is substituted with an aryl group and/or a heteroaryl group. It means an amine, and the alkylamine group means an amine substituted with an alkyl, and examples of the aryl (heteroaryl) amine group include a substituted or unsubstituted mono aryl (heteroaryl) amine group, a substituted or unsubstituted diaryl ( There is a heteroaryl) amine group or a substituted or unsubstituted triaryl (heteroaryl) amine group, and the aryl group and the heteroaryl group in the aryl (heteroaryl) amine group are the same as the definitions of the aryl group and the heteroaryl group, and the above The alkyl group of the alkylamine group is also the same as the definition of the above alkyl group.

Illustratively, the arylamine group includes a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 3-methyl-phenylamine group, a 4-methyl-naphthylamine group, and a 2-methyl-biphenyl group. amine group, 9-methyl-anthracenylamine group, diphenyl amine group, phenyl naphthylamine group, ditolylamine group, phenyltolylamine group and triphenylamine group, but are not limited thereto.

In the present invention, the silyl group is an unsubstituted silyl group or an alkylsilyl group or an arylsilyl group substituted with an alkyl group or an aryl group, and specific examples of such a silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, and trimethylsilyl. and the like, but are not limited thereto.

Specific examples of the substituent halogen group used in the present invention include fluorine (F), chlorine (Cl), and bromine (Br).

In the present invention, the cycloalkyl group refers to and includes monocyclic, polycyclic and spiroalkyl radicals, preferably containing ring carbon atoms of 3 to 20 carbon atoms, cyclopropyl, cyclopentyl, cyclohexyl, bicyclo heptyl, spirodecyl, spirundecyl, adamantyl, and the like, and the cycloalkyl group may be optionally substituted.

In the present invention, heterocycloalkyl groups refer to and include aromatic and non-aromatic cyclic radicals containing one or more heteroatoms, one or more heteroatoms being O, S, N, P, B, Si, and Se , Preferably selected from O, N or S, specifically, when N is included, it may be aziridine, pyrrolidine, piperidine, azepane, azocan, and the like.

In the present invention, the carbonyl group is represented by -COR', where R' is hydrogen, an alkyl group, an aryl group, a cycloalkyl group, an alkenyl group, an alkynyl group, or a combination thereof.

The organic compound according to the present invention represented by [Chemical Formula I] may be used as a material for a light efficiency improvement layer (capping layer) provided in an organic light emitting device due to its structural specificity.

Preferred specific examples of the organic compound represented by [Chemical Formula I] according to the present invention include the following compounds, but are not limited thereto.

As described above, the organic compound according to the present invention can synthesize organic compounds having various characteristics by using a moiety having intrinsic characteristics, and as a result, the organic compound according to the present invention is provided in an organic light emitting device. When applied to the light efficiency improving layer, light emitting characteristics such as light emitting efficiency of the device can be further improved.

In addition, the compound of the present invention can be applied to a device according to a general organic light emitting device manufacturing method, and an organic light emitting device according to an embodiment of the present invention includes a first electrode and a second electrode and an organic layer disposed therebetween. It can be made of a structure, and can be manufactured using conventional device manufacturing methods and materials, except that the organic light emitting compound according to the present invention is used in the organic layer of the device.

The organic layer of the organic light emitting device according to the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are stacked. For example, it 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, an electron blocking layer, a hole blocking layer, a light efficiency improvement layer (capping layer), and the like. However, it is not limited thereto and may include fewer or more organic layers.

An organic light emitting device according to an embodiment of the present invention includes a substrate, a first electrode (anode), an organic layer, a second electrode (cathode), and a light efficiency improvement layer, wherein the light efficiency improvement layer is a bottom emission layer of the first electrode. ) or on top of the second electrode (top emission).

In the method formed on the second electrode (top emission), the light formed in the light emitting layer is emitted toward the cathode, and the light emitted toward the cathode passes through the light efficiency improving layer (CPL) formed of the compound according to the present invention having a relatively high refractive index. The wavelength of the light is amplified and thus the light efficiency is increased.

An organic layer structure of a preferred organic light emitting device according to the present invention will be described in more detail in Examples to be described later.

In addition, the organic light emitting device according to the present invention uses a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a metal or conductive metal oxide or an alloy thereof on a substrate. It can be manufactured by depositing an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then 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 layer, and an anode material on a substrate. The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic layer can be formed by using various polymer materials and using a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. Can be made in layers.

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 anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO). Metal oxides, combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT) , but conductive polymers such as 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 layer. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof, and multilayers such as LiF/Al or LiO ₂ /Al. structural materials, etc., but are not limited thereto.

The hole injection material is a material capable of injecting holes well from the anode at a low voltage, and the hole injection material preferably has a highest occupied molecular orbital (HOMO) 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 porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, Anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high hole mobility 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 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, benzoxazoles, benzthiazoles, and Examples include benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, and rubrene, but are not limited thereto.

As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is suitable. Specific examples include an Al complex of 8-hydroxyquinoline, a complex including Alq ₃ , an organic radical compound, and a hydroxyflavone-metal complex, but are not limited thereto.

The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a double side emission type depending on the material used.

In addition, the organic light emitting compound according to the present invention may act in organic electronic devices including organic solar cells, organic photoreceptors, organic transistors, and the like, on a principle similar to that applied to organic light emitting devices.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are intended to explain the present invention in more detail, and the scope of the present invention is not limited thereto, and various changes and modifications are possible within the scope and spirit of the present invention. It will be self-evident to those who have knowledge.

synthesis example 1: Synthesis of Compound 7

(One) manufacturing example 1: synthesis of intermediate 7-1

1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), Heptafluoro-2-iodopropane (32.9 g, 0.111 mol), Cu (18.8 g, 0.296 mol), and 30 mL of DMF were added and stirred for 24 hours under nitrogen conditions. While stirring at 100 ℃ was reacted. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 7.6 g of <Intermediate 7-1> (yield: 45.8%).

(2) manufacturing example 2: synthesis of intermediate 7-2

1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), Phenyl-D5-boronic acid (11.3 g, 0.089 mol), K ₂ CO ₃ (30.7 g, 0.222 mol), Pd(PPh ₃ ) ₄ ( 0.9 g, 0.74 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 80 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 7.3 g of <Intermediate 7-2> (yield: 71.8%).

(3) manufacturing example 3: synthesis of intermediate 7-3

Intermediate 7-2 (10.0 g, 0.036 mol), Bis(pinacolato)diboron (25.0 g, 0.043 mol), KOAc (7.1 g, 0.072 mol), Pd(dppf)Cl ₂ (0.8 g, 1.08 mmol), X- Dioxane (200 mL) was added to Phos (0.6 g, 1.29 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 9.1 g (yield 68.3%) of <Intermediate 7-3> was obtained by extraction and concentration, followed by column and recrystallization.

(4) manufacturing example 4: synthesis of compound 7

Intermediate 7-1 (10.0 g, 0.022 mol), Intermediate 7-3 (9.8 g, 0.027 mol), K ₂ CO ₃ (9.2 g, 0.066 mol), Pd(OAc) ₂ (1.3 g, 1.1 mmol), X -Phos (1.1 g, 2.2 mmol), 200 mL of THF and 50 mL of H ₂ O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 10.3 g of <Compound 7> (yield: 70.8%).

LC/MS: m/z = 652 [(M) ⁺ ]

synthesis example 2: synthesis of compound 17

(One) manufacturing example 1: synthesis of intermediate 17-1

1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), 3,5-Bis(tert-butyl)phenyl-pinacolatoboronate (28.1 g, 0.089 mol), K ₂ CO ₃ (30.7 g, 0.222 mol), 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O were added to Pd(PPh ₃ ) ₄ (0.9 g, 0.74 mmol), followed by stirring at 80 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 13.8 g of <Intermediate 7-1> (yield: 76.3%).

(2) manufacturing example 2: synthesis of intermediate 17-2

Intermediate 17-1 (10.0 g, 0.020 mol), Bis(pinacolato)diboron (14.1 g, 0.024 mol), KOAc (4.0 g, 0.040 mol), Pd(dppf)Cl ₂ (0.5 g, 0.6 mmol), X- Dioxane (200 mL) was added to Phos (0.4 g, 0.72 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 8.4 g (yield 70.8%) of <Intermediate 17-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) manufacturing example 3: Synthesis of Compound 17

Intermediate 7-1 (10.0 g, 0.022 mol), Intermediate 17-2 (15.5 g, 0.026 mol), K ₂ CO ₃ (9.2 g, 0.066 mol), Pd(OAc) ₂ (1.3 g, 1.1 mmol), X -Phos (1.1 g, 2.2 mmol), 200 mL of THF and 50 mL of H ₂ O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted and concentrated, and then column and recrystallized to obtain 12.5 g of <Compound 17> (yield: 64.7%).

LC/MS: m/z=866 [(M) ⁺ ]

synthesis example 3: synthesis of compound 19

(One) manufacturing example 1: synthesis of intermediate 19-1

1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), 3,5-Bis(trifluoromethyl)phenylboronic acid (22.9 g, 0.089 mol), K ₂ CO ₃ (30.7 g, 0.222 mol), Pd (PPh) ₃ ) 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O were added to ₄ (0.9 g, 0.74 mmol), followed by stirring at 80 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 15.4 g of <Intermediate 19-1> (yield: 77.6%).

(2) manufacturing example 2: synthesis of intermediate 19-2

Intermediate 19-1 (10.0 g, 0.019 mol), Bis(pinacolato)diboron (12.8 g, 0.023 mol), KOAc (3.7 g, 0.038 mol), Pd(dppf)Cl ₂ (0.4 g, 0.57 mmol), X- Dioxane (200 mL) was added to Phos (0.3 g, 0.69 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 7.9 g (yield 67.5%) of <Intermediate 19-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) manufacturing example 3: synthesis of compound 19

Intermediate 7-1 (10.0 g, 0.022 mol), Intermediate 19-2 (16.8 g, 0.026 mol), K ₂ CO ₃ (9.2 g, 0.066 mol), Pd(OAc) ₂ (1.3 g, 1.1 mmol), X -Phos (1.1 g, 2.2 mmol), 200 mL of THF and 50 mL of H ₂ O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 14.7 g of <Compound 19> (yield: 72.1%).

LC/MS: m/z=914(M) ⁺ ]

synthesis example 4: synthesis of compound 34

(One) manufacturing example 1: synthesis of intermediate 34-1

4'-Bromo-3,5-Bis(Trifluoromethyl)-1,1'-Biphenyl (10.0 g, 0.027 mol), Bis(pinacolato)diboron (8.3 g, 0.032 mol), KOAc (8.0 g, 0.081 mol), 200 mL of Dioxane was added to Pd(dppf)Cl ₂ (1.0 g, 1.35 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 8.6 g of <Intermediate 34-1> (yield: 76.3%).

(2) manufacturing example 2: synthesis of intermediate 34-2

1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), intermediate 34-1 (36.9 g, 0.089 mol), K ₂ CO ₃ (30.7 g, 0.222 mol), Pd(PPh ₃ ) ₄ (0.9 g , 0.74 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 80 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 18.2 g of <Intermediate 34-2> (yield: 71.4%).

(3) manufacturing example 3: synthesis of intermediate 34-3

Intermediate 34-2 (10.0 g, 0.015 mol), Bis(pinacolato)diboron (10.0 g, 0.018 mol), KOAc (2.9 g, 0.030 mol), Pd(dppf)Cl ₂ (0.3 g, 0.45 mmol), X- 200 mL of Dioxane was added to Phos (0.3 g, 0.54 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 7.4 g (yield 65.3%) of <Intermediate 34-3> was obtained by extraction, concentration, column and recrystallization.

(4) manufacturing example 4: synthesis of compound 34

Intermediate 7-1 (10.0 g, 0.022 mol), Intermediate 34-3 (20.9 g, 0.026 mol), K ₂ CO ₃ (9.2 g, 0.066 mol), Pd(OAc) ₂ (1.3 g, 1.1 mmol), X -Phos (1.1 g, 2.2 mmol), 200 mL of THF and 50 mL of H ₂ O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 16.8 g of <Compound 34> (yield: 70.7%).

LC/MS: m/z=1066(M) ⁺ ]

synthesis example 5: Synthesis of Compound 42

(One) manufacturing example 1: synthesis of intermediate 42-1

1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), 2-Pyrrolidinone (7.6 g, 0.089 mol), K ₃ PO ₄ (33.7 g, 0.104 mol), Pd(dba) ₂ (2.1 g, 3.7 mmol), Xant-Phos (15.4 g, 0.027 mol), and dioxane were added and stirred under reflux for 16 hours to react. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 8.3 g of <Intermediate 42-1> (yield: 80.5%).

(2) manufacturing example 2: synthesis of intermediate 42-2

Intermediate 42-1 (10.0 g, 0.036 mol), Bis(pinacolato)diboron (24.7 g, 0.043 mol), KOAc (7.0 g, 0.072 mol), Pd(dppf)Cl ₂ (0.8 g, 1.08 mmol), X- Dioxane (200 mL) was added to Phos (0.6 g, 1.29 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, after extraction and concentration, 9.1 g (yield 68.5%) of <Intermediate 42-2> was obtained by column.

(3) manufacturing example 3: synthesis of intermediate 42-3

1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), intermediate 42-2 (32.9 g, 0.089 mol), K ₂ CO ₃ (30.7 g, 0.222 mol), Pd(PPh ₃ ) ₄ (0.9 g , 0.74 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 80 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 17.4 g of <Intermediate 42-3> (yield: 78.8%).

(4) manufacturing example 4: synthesis of intermediate 42-4

Intermediate 42-3 (10.0 g, 0.017 mol), Bis(pinacolato)diboron (11.5 g, 0.020 mol), KOAc (3.3 g, 0.034 mol), Pd(dppf)Cl ₂ (0.4 g, 0.51 mmol), X- Dioxane (200 mL) was added to Phos (0.3 g, 0.6 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 8.2 g (yield 71.1%) of <Intermediate 42-4> was obtained by extraction and concentration, followed by column and recrystallization.

(5) manufacturing example 5: Synthesis of Compound 42

Intermediate 7-1 (10.0 g, 0.022 mol), Intermediate 42-4 (18.4 g, 0.026 mol), K ₂ CO ₃ (9.2 g, 0.066 mol), Pd(OAc) ₂ (1.3 g, 1.1 mmol), X -Phos (1.1 g, 2.2 mmol), 200 mL of THF and 50 mL of H ₂ O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted and concentrated, followed by column and recrystallization to obtain 14.3 g of <Compound 42> (yield: 65.8%).

LC/MS: m/z=1974(M) ⁺ ]

synthesis example 6: synthesis of compound 52

(One) manufacturing example 1: synthesis of intermediate 52-1

1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), 5-(2-Trfluoromethylphenyl)pyridine-2-boronic acid pinacol ester (31.0 g, 0.089 mol), K ₂ CO ₃ (30.7 g, 0.222 mol) ) and Pd(PPh ₃ ) ₄ (0.9 g, 0.74 mmol), 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O were added and reacted by stirring at 80 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 15.1 g of <Intermediate 52-1> (yield: 73.6%).

(2) manufacturing example 2: synthesis of intermediate 52-2

Intermediate 52-1 (10.0 g, 0.018 mol), Bis(pinacolato)diboron (12.4 g, 0.022 mol), KOAc (3.5 g, 0.036 mol), Pd(dppf)Cl ₂ (0.4 g, 0.54 mmol), X- Dioxane (200 mL) was added to Phos (0.3 g, 0.66 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 7.1 g (yield: 61.0%) of <Intermediate 52-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) manufacturing example 3: Synthesis of Compound 52

Intermediate 7-1 (10.0 g, 0.022 mol), Intermediate 52-2 (17.3 g, 0.026 mol), K ₂ CO ₃ (9.2 g, 0.066 mol), Pd(OAc) ₂ (1.3 g, 1.1 mmol), X -Phos (1.1 g, 2.2 mmol), 200 mL of THF and 50 mL of H ₂ O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 14.3 g of <Compound 52> (yield: 68.8%).

LC/MS: m/z=932(M) ⁺ ]

synthesis example 7: synthesis of compound 105

(One) manufacturing example 1: synthesis of intermediate 105-1

Intermediate 7-1 (10.0 g, 0.022 mol), Bis(pinacolato)diboron (15.3 g, 0.026 mol), KOAc (4.4 g, 0.044 mol), Pd(dppf)Cl ₂ (0.5 g, 0.66 mmol), X- Dioxane (200 mL) was added to Phos (0.4 g, 0.78 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 8.6 g (yield 71.4%) of <Intermediate 105-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) manufacturing example 2: synthesis of intermediate 105-2

1-Bromo-4-chlorobenzene (10.0 g, 0.052 mol), intermediate 105-1 (33.9 g, 0.062 mol), K ₂ CO ₃ (21.7 g, 0.156 mol), Pd(PPh ₃ ) ₄ (1.2 g, 1.04 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 80 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 21.8 g of <Intermediate 105-2> (yield: 79.6%).

(3) manufacturing example 3: synthesis of intermediate 105-3

1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), 9,9-Dimethylfluoren-2-boronic acid (21.1 g, 0.089 mol), K ₂ CO ₃ (30.7 g, 0.222 mol), Pd (PPh) ₃ ) 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O were added to ₄ (0.9 g, 0.74 mmol), followed by stirring at 80 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 13.7 g of <Intermediate 105-3> (yield: 74.5%).

(4) manufacturing example 4: synthesis of intermediate 105-4

Intermediate 105-3 (10.0 g, 0.020 mol), Bis(pinacolato)diboron (13.9 g, 0.024 mol), KOAc (4.0 g, 0.040 mol), Pd(dppf)Cl ₂ (0.4 g, 0.6 mmol), X- Dioxane (200 mL) was added to Phos (0.4 g, 0.72 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 8.1 g (yield 68.4%) of <Intermediate 105-4> was obtained by extraction and concentration, followed by column and recrystallization.

(5) manufacturing example 5: Synthesis of Compound 105

Intermediate 105-2 (10.0 g, 0.019 mol), Intermediate 105-4 (13.5 g, 0.023 mol), K ₂ CO ₃ (7.9 g, 0.057 mol), Pd(OAc) ₂ (1.1 g, 0.95 mmol), X -Phos (0.9 g, 1.9 mmol), 200 mL of THF and 50 mL of H ₂ O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted and concentrated, followed by column and recrystallization to obtain 12.7 g of <Compound 105> (yield: 70.1%).

LC/MS: m/z=950(M) ⁺ ]

synthesis example 8: synthesis of compound 129

(One) manufacturing example 1: synthesis of intermediate 129-1

2-Bromo-5-chloropyridine (10.0 g, 0.052 mol), 3,5-Bis(trifluoromethyl)phenylboronic acid (16.1 g, 0.062 mol), K ₂ CO ₃ (21.6 g, 0.156 mol), Pd(PPh ₃ ) 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O were added to ₄ (1.2 g, 1.04 mmol) and reacted by stirring at 80 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 12.7 g of <Intermediate 129-1> (yield: 75.1%).

(2) manufacturing example 2: synthesis of intermediate 129-2

Intermediate 129-1 (10.0 g, 0.031 mol), Bis(pinacolato)diboron (21.1 g, 0.037 mol), KOAc (6.0 g, 0.062 mol), Pd(dppf)Cl ₂ (0.7 g, 0.93 mmol), X- 200 mL of Dioxane was added to Phos (0.5 g, 1.11 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, after extraction and concentration, 9.1 g (yield 71.0%) of <Intermediate 129-2> was obtained by column.

(3) manufacturing example 3: synthesis of intermediate 129-3

1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), intermediate 129-2 (37.0 g, 0.089 mol), K ₂ CO ₃ (30.7 g, 0.222 mol), Pd(PPh ₃ ) ₄ (0.9 g , 0.74 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 80 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 18.7 g of <Intermediate 129-3> (yield: 73.2%).

(4) manufacturing example 4: synthesis of intermediate 129-4

Intermediate 129-3 (10.0 g, 0.015 mol), Bis(pinacolato)diboron (10.0 g, 0.018 mol), KOAc (2.8 g, 0.030 mol), Pd(dppf)Cl ₂ (0.3 g, 0.45 mmol), X- 200 mL of Dioxane was added to Phos (0.3 g, 0.54 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 7.6 g (yield: 67.1%) of <Intermediate 129-4> was obtained by extraction and concentration, followed by column and recrystallization.

(5) manufacturing example 5: Synthesis of Compound 129

Intermediate 105-2 (10.0 g, 0.019 mol), Intermediate 129-4 (17.9 g, 0.023 mol), K ₂ CO ₃ (7.9 g, 0.057 mol), Pd(OAc) ₂ (1.1 g, 0.95 mmol), X -Phos (0.9 g, 1.9 mmol), 200 mL of THF and 50 mL of H ₂ O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 14.2 g of <Compound 129> (yield: 65.1%).

LC/MS: m/z=1144(M) ⁺ ]

synthesis example 9: synthesis of compound 139

(One) manufacturing example 1: synthesis of intermediate 139-1

1-Bromo-4-tert-butylbenzene (10.0 g, 0.047 mol), 2-Aminobenzotrifluoride (11.3 g, 0.071 mol), NaOtBu (13.5 g, 0.142 mol), Pd(dba) ₂ (1.1 g, 1.88 mmol), 150 mL of Toluene was added to t-Bu ₃ P (0.8 g, 3.76 mmol), followed by stirring at 70 °C for 4 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 9.7 g of <Intermediate 139-1> (yield: 70.5%).

(2) manufacturing example 2: synthesis of intermediate 139-2

1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), intermediate 139-1 (32.6 g, 0.111 mol), NaOtBu (21.3 g, 0.222 mol), Pd(dba) ₂ (0.9 g, 1.48 mmol) , Toluene 150 mL was added to t-Bu ₃ P (0.6 g, 2.96 mmol) and reacted by stirring at 70 °C for 4 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 18.9 g of <Intermediate 139-2> (yield: 73.5%).

(3) manufacturing example 3: synthesis of intermediate 139-3

Intermediate 139-2 (10.0 g, 0.014 mol), Bis(pinacolato)diboron (9.9 g, 0.017 mol), KOAc (2.8 g, 0.028 mol), Pd(dppf)Cl ₂ (0.3 g, 0.42 mmol), X- Dioxane (200 mL) was added to Phos (0.3 g, 0.51 mmol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 7.3 g (yield 64.5%) of <Intermediate 139-3> was obtained by extraction and concentration, followed by column and recrystallization.

(4) manufacturing example 4: Synthesis of Compound 139

Intermediate 105-2 (10.0 g, 0.019 mol), Intermediate 139-3 (18.0 g, 0.023 mol), K ₂ CO ₃ (7.9 g, 0.057 mol), Pd(OAc) ₂ (1.1 g, 0.95 mmol), X -Phos (0.9 g, 1.9 mmol), 200 mL of THF and 50 mL of H ₂ O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 14.5 g of <Compound 139> (yield: 66.2%).

LC/MS: m/z=1148(M) ⁺ ]

synthesis example 10: synthesis of compound 181

(One) manufacturing example 1: synthesis of intermediate 181-1

2-Bromo-6-chloronaphthalene (10.0 g, 0.041 mol), intermediate 105-1 (26.8 g, 0.049 mol), K ₂ CO ₃ (17.2 g, 0.123 mol), Pd(PPh ₃ ) ₄ (1.0 g, 0.82 mmol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 80 °C for 6 hours. After completion of the reaction, 17.9 g (yield 75.2%) of <Intermediate 181-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) manufacturing example 2: Synthesis of Compound 181

Intermediate 181-1 (10.0 g, 0.017 mol), Intermediate 17-2 (12.1 g, 0.020 mol), K ₂ CO ₃ (7.2 g, 0.051 mol), Pd(OAc) ₂ (1.0 g, 0.85 mmol), X -Phos (0.8 g, 1.7 mmol), 200 mL of THF and 50 mL of H ₂ O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 12.6 g of <Compound 181> (yield: 72.9%).

LC/MS: m/z=992(M) ⁺ ]

synthesis example 11: synthesis of compound 191

(One) manufacturing example 1: Synthesis of Compound 191

Intermediate 181-1 (10.0 g, 0.017 mol), Intermediate 42-2 (7.7 g, 0.020 mol), K ₂ CO ₃ (7.2 g, 0.051 mol), Pd(OAc) ₂ (1.0 g, 0.85 mmol), X -Phos (0.8 g, 1.7 mmol), 200 mL of THF and 50 mL of H ₂ O were added and reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 9.3 g of <Compound 191> (yield: 68.3%).

LC/MS: m/z=782(M) ⁺ ]

device Example (CPL)

In an example according to the present invention, the anode was patterned to have a light emitting area of 2 mm × 2 mm using an ITO glass substrate containing Ag of 25 mm × 25 mm × 0.7 mm, and then washed. After mounting the patterned ITO substrate in a vacuum chamber, an organic material and a metal were deposited on the substrate at a process pressure of 1 × 10 ^-6 torr or more in the following structure.

device Example 1 to 31

After employing the compound implemented according to the present invention in the light efficiency improvement layer provided in the device to manufacture an organic light emitting device having the following device structure, light emission and driving of the compound implemented according to the present invention and the device including the same properties were measured.

Ag/ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (α-NPB, 100 nm) / electron blocking layer (EB1, 10 nm) / light emitting layer (20 nm) / electron transport layer (ET1:Liq, 30 nm) / LiF (1 nm) / Mg:Ag (15 nm) / light efficiency improvement layer (70 nm)

A hole injection layer was formed by depositing [HAT-CN] to a thickness of 5 nm on top of an ITO transparent electrode containing Ag on a glass substrate, and a hole transport layer was formed by depositing [α-NPB] to a thickness of 100 nm, [ EB1] was formed to a thickness of 10 nm to form an electron blocking layer. Thereafter, [BH1] as a host compound and [BD1] as a dopant compound were used to form a light emitting layer by co-evaporation to 20 nm, and an electron transport layer (50% doped with Liq of [201] compound) was deposited at 30 nm, followed by LiF was formed to a thickness of 1 nm to form an electron injection layer, and Mg:Ag was formed to a thickness of 15 nm at a ratio of 1:9 to form a cathode. In addition, a light efficiency improvement layer (capping layer) was formed to a thickness of 70 nm with a compound implemented according to the present invention to manufacture an organic light emitting device.

device comparative example One

The organic light emitting device for Device Comparative Example 1 was manufactured in the same manner as the device structures of Examples 1 to 31, except that the light efficiency improving layer was not provided.

device comparative example 2

The organic light emitting device for Device Comparative Example 2 was manufactured in the same manner as in the device structures of Examples 1 to 31, except that Alq ₃ was used instead of the compound according to the present invention as a light efficiency improving layer compound.

Experimental example 1: element Example Luminescence characteristics of 1 to 31

Driving voltage, current efficiency and color coordinates were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research) for the organic light emitting device manufactured according to the above Examples and Comparative Examples, 1,000 nit The standard result values are shown in [Table 1] below.

Example Light Efficiency Improvement Layer V cd/A CIEx CIEy One Formula 2 3.73 8.95 0.1384 0.0556 2 Formula 5 3.77 8.19 0.1414 0.0481 3 Formula 8 3.91 8.75 0.1384 0.0549 4 Formula 10 3.67 8.17 0.1405 0.0526 5 Formula 11 3.82 8.13 0.1366 0.0518 6 Formula 12 3.73 8.60 0.1386 0.0545 7 Formula 13 3.42 8.19 0.1393 0.0478 8 Formula 15 3.62 8.34 0.1406 0.0545 9 Formula 18 3.83 8.21 0.1312 0.0515 10 Formula 21 3.61 8.72 0.1388 0.0497 11 Formula 22 3.64 8.15 0.1392 0.0456 12 Formula 23 3.56 8.49 0.1373 0.0538 13 Formula 25 3.80 8.20 0.1306 0.0512 14 Formula 26 3.64 8.34 0.1364 0.0487 15 Formula 27 3.79 8.43 0.1366 0.0523 16 Formula 28 3.67 8.13 0.1396 0.0566 17 Formula 29 3.77 8.39 0.1405 0.0457 18 Formula 32 3.62 8.23 0.1422 0.0463 19 Formula 34 3.80 8.25 0.1352 0.0497 20 Formula 36 3.61 8.40 0.1407 00546 21 Formula 40 3.73 8.25 0.1374 0.0545 22 Formula 45 3.90 8.41 0.1372 0.0541 23 Formula 51 3.68 8.24 0.1388 0.0526 24 Formula 54 3.73 8.52 0.1415 0.0544 25 Formula 55 3.83 8.15 0.1377 0.0473 26 Formula 56 3.67 8.21 0.1437 0.0506 27 Formula 57 3.72 8.34 0.1373 0.0512 28 Formula 59 3.55 8.41 0.1422 0.0487 29 Formula 60 3.89 8.26 0.1383 0.0523 30 Formula 62 3.86 8.40 0.1393 0.0515 31 Formula 65 3.72 8.18 0.1343 0.0490 Comparative Example 1 not used 4.68 7.03 0.1502 0.1412 Comparative Example 2 Alq ₃ 4.33 7.84 0.1471 0.0583

Looking at the results shown in [Table 1], in the case of an organic light emitting device employing the compound according to the present invention in the light efficiency improvement layer provided in the device, it is used as a conventional light efficiency improvement layer material and a device without a light efficiency improvement layer. It can be confirmed that the driving voltage is reduced and the current efficiency is improved compared to the devices (Comparative Examples 1 and 2) employing the compound having the compound.

[HAT_CN] [α-NPB] [BH1] [BD1] [ET1]

[EB1]

Claims (5)

A compound represented by the following [Formula I]:
[Formula I]

In the above [Formula I],
L is each independently a direct bond, or any one selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms,
n is an integer from 0 to 3, and when n is 2 or more, a plurality of L's are the same as or different from each other;
Ar ₁ and Ar ₂ are the same as or different from each other, and are each independently deuterium (D), a cyano group (CN), a halogen group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. Alkoxy group, substituted or unsubstituted halogenated alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted halogenated alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted It is any one selected from a heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and a substituted or unsubstituted amine group. According to claim 1,
In the definition of L, Ar ₁ and Ar ₂ , 'substituted or unsubstituted' means that L, Ar ₁ and Ar ₂ are deuterium, a halogen group, a cyano group, an alkyl group, a halogenated alkyl group, a deuterated alkyl group, Substituted with one or two or more substituents selected from a cycloalkyl group, a heterocycloalkyl group, an alkoxy group, a halogenated alkoxy group, a deuterated alkoxy group, an aryl group, a heteroaryl group, an alkylsilyl group, an arylsilyl group, and a carbonyl group, or the above substituents A compound which means that two or more of the substituents are substituted with linked substituents or have no substituents. According to claim 1,
[Formula I] is any one compound selected from the following [Compound 1] to [Compound 206]:

An organic light emitting device comprising a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode,
Further comprising a light efficiency improvement layer (Capping layer) formed on at least one side opposite to the organic layer among the upper or lower portions of the first electrode and the second electrode,
The light efficiency improving layer is an organic light emitting device including a compound represented by [Chemical Formula I]. According to claim 4,
The light efficiency improving layer is formed on at least one of a lower portion of the first electrode and an upper portion of the second electrode.