KR20220104859A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to a novel organic light emitting compound represented by chemical formula I, which is adopted in an organic layer in an organic light emitting device or a light efficiency improvement layer provided in the organic light emitting device to implement light emitting properties such as low-voltage driving of the device, and excellent color purity and luminous efficiency; and an organic light emitting device including the same.

Description

An organic light emitting compound and an organic light emitting device comprising the same

The present invention relates to an organic light emitting compound, and more particularly, to an organic layer such as a hole transport layer, an electron transport layer, a light emitting layer in an organic light emitting device, and a light efficiency improvement layer (Capping layer) provided in the device, characterized in that it is employed as a material It relates to an organic light emitting compound and an organic light emitting device having significantly improved light emitting characteristics such as low voltage driving and excellent light emission efficiency of the device by employing the same.

The organic light emitting device can be formed on a transparent substrate as well as being able to drive at a low voltage of 10 V or less compared to a plasma display panel or an inorganic electroluminescence (EL) display, and consume relatively little power. , has the advantage of excellent color, and can represent three colors of green, blue, and red, and has recently become a subject of much interest as a next-generation display device.

However, in order for such an organic light emitting device to exhibit the above characteristics, a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. However, the development of a stable and efficient organic layer material for an organic light emitting device has not yet been sufficiently developed.

Therefore, in order to realize a more stable organic light emitting device, and to achieve high efficiency, long lifespan, and large size of the device, additional improvements are required in terms of efficiency and lifespan characteristics. It is desperately needed.

In this regard, recently, with respect to the material of the hole transport layer in the structure of the organic light emitting device, research for improving the conductivity of the existing organic material has been actively conducted.

In addition, in order to obtain the maximum efficiency in the emission layer, the energy bandgap of the host and the dopant must be properly combined so that holes and electrons move to the dopant through a stable electrochemical path, respectively, to form excitons.

In addition, in recent years, research on improving the characteristics of an organic light emitting device by giving a change in the performance of each organic layer material, as well as a technology for improving color purity and increasing luminous efficiency by an optical thickness optimized between an anode and a cathode has been developed. It has been focused on one of the important factors for improving the performance, and as an example of this method, an increase in light efficiency and excellent color purity are achieved by using a capping layer on an electrode.

Therefore, the present invention is employed in organic layers such as a hole transport layer, an electron transport layer, and a light emitting layer in an organic light emitting device and a light efficiency improving layer provided in the device to realize excellent light emitting characteristics such as low voltage driving and improved luminous efficiency of the device. An object of the present invention is to provide a light emitting compound and an organic light emitting device including the same.

In order to solve the above problems, the present invention provides any one organic light emitting compound selected from the compounds represented by the following [Formula I].

[Formula Ⅰ]

The characteristic structure of the [Formula I] and specific compounds implemented thereby, and A ₁ to A ₂ will be described later.

In addition, the present invention is an organic light emitting device including a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein the first electrode and the upper or lower portion of the second electrode An organic light emitting device comprising an organic light emitting compound represented by the [Formula I] in the light efficiency improving layer while further comprising a light efficiency improving layer (Capping layer) formed on at least one side opposite to the organic layer among do.

In addition, there is provided an organic light emitting device including the compound represented by the [Formula I] in the hole transport layer, the electron transport layer, the light emitting layer in the organic light emitting device.

When the organic light emitting compound according to the present invention is employed as a material for an organic layer in an organic light emitting device or a light efficiency improving layer provided in the device, it is possible to realize improved light emitting characteristics such as low voltage driving of the device and excellent luminous efficiency and color purity, and thus various display devices. can be usefully used for

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

The present invention is employed as a material for a hole transport layer, an electron transport layer, a light emitting layer or a light efficiency improvement layer provided in the device in an organic light emitting device, so that the low voltage driving of the device, excellent luminous efficiency, and luminous properties such as color purity can be achieved. It relates to an organic light emitting compound, characterized in that represented by.

[Formula Ⅰ]

In the above [Formula I],

A ₁ and A ₂ are the same as or different from each other, and each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, and at least one of A ₁ and A ₂ is a substituted or unsubstituted 10 to 50 It is characterized in that it is an aromatic hydrocarbon ring.

A ₁ and A ₂ are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 2 to C 20 alkenyl group, a substituted or unsubstituted A cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 20 carbon atoms, substituted Or an unsubstituted C1 to C20 halogenated alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C6 to C30 of an arylamine group, a substituted or unsubstituted heteroarylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted arylheteroarylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, and It has at least one substituent selected from a substituted or unsubstituted C6-C30 arylsilyl group.

According to an embodiment of the present invention, A ₁ and A ₂ are each independently selected from [Structural Formula 1] to [Structural Formula 3], and at least one of A ₁ and A ₂ is selected from the following [Structural Formula 2] to It is characterized in that it is selected from [Structural Formula 3].

[Structural Formula 1] [Structural Formula 2] [Structural Formula 3]

In the [Structural Formula 1] to [Structural Formula 3],

R ₁ To R ₃ are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 2 to C 20 alkenyl group, a substituted or unsubstituted C A cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 20 carbon atoms, a substituted or An unsubstituted C 1 to C 20 halogenated alkoxy group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 3 to C 30 heteroaryl group, a substituted or unsubstituted C 6 to C 30 An arylamine group, a substituted or unsubstituted heteroarylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted arylheteroarylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, and a substituted or an unsubstituted C6-C30 arylsilyl group.

n is an integer from 0 to 4, m is an integer from 0 to 6, l is an integer from 0 to 6, and when n, m and l are 2 or more, a plurality of R ₁ to R ₃ are the same as or different from each other, respectively. do.

'*' represents a site binding to [Formula I].

Meanwhile, in the definition of A ₁ , A ₂ , R ₁ to R ₃ , 'substituted or unsubstituted' means deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, an amine group, a silyl group, an alkyl group, a cycloalkyl group. , alkoxy group, alkenyl group, aryl group, heteroaryl group and substituted with one or two or more substituents selected from the group consisting of silyl group, or substituted with a substituent to which two or more of the substituents are connected, or means that it does not have any substituents do.

For specific examples, the substituted arylene group means that 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. are substituted with other substituents it means.

In addition, the substituted heteroarylene 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 a condensed heterocyclic group thereof, such as benzquinoline. It means that the group, benzimidazole group, benzoxazole group, benzthiazole group, benzcarbazole group, dibenzothiophenyl group, dibenzofuran group, etc. are substituted with other substituents.

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

In the present invention, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, 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, cyclopentylmethyl 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, and the like, but is not limited thereto.

In the present invention, the alkoxy group may be straight-chain or branched. Although the number of carbon atoms of the alkoxy group is not particularly limited, it is preferably 1 to 20, which is a range that does not cause steric hindrance. 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 , a benzyloxy group, a p-methylbenzyloxy group, etc., but is not limited thereto.

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. Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and a stilbene group, and examples of the polycyclic aryl group include a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, tetracenyl group. , chrysenyl group, fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthrene group, etc., but the scope of the present invention is not limited to these examples.

,

,

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

,

,

etc.

,

등이 있다.In the present invention, the fluorenyl group includes a structure of an open fluorenyl group, wherein the open fluorenyl group is a structure in which one ring compound is disconnected in 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 2 to 30 carbon atoms, and a specific example thereof in the present invention is a thiophene group , furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group, pyra Zinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxa Zol group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadia and a zolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, a phenoxazine group, a phenothiazine group, and the like, but are not limited thereto.

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

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

In the present invention, the cycloalkyl group refers to, and includes, monocyclic, polycyclic and spiro alkyl radicals, preferably containing 3 to 20 ring carbon atoms, cyclopropyl, cyclopentyl, cyclohexyl, bicyclo heptyl, spirodecyl, spirodecyl, adamantyl, and the like, wherein 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, wherein one or more heteroatoms are O, S, N, P, B, Si, and Se , Preferably it is selected from O, N, or S, and specifically, when N is included, it may be aziridine, pyrrolidine, piperidine, azepane, azocan, and the like.

In the present invention, an alkenyl group refers to and includes both straight and branched chain alkene radicals, and an alkenyl group is essentially an alkyl group comprising at least one carbon-carbon double bond in the alkyl chain. A cycloalkenyl group is essentially a cycloalkyl group comprising one or more carbon-carbon double bonds within the cycloalkyl ring.

In the present invention, the amine group may be -NH ₂ , an alkylamine group, an arylamine group, an arylheteroarylamine group, etc., the arylamine group means an amine substituted with aryl, and the alkylamine group means an amine substituted with an alkyl The aryl heteroarylamine group means an amine substituted with aryl and heteroaryl groups, and examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or There is an unsubstituted triarylamine group, and the aryl group and heteroaryl group in the arylamine group and the arylheteroarylamine group may be a monocyclic aryl group or a monocyclic heteroaryl group, and may be a polycyclic aryl group or a polycyclic heteroaryl group. and the aryl group, the arylamine group containing two or more heteroaryl groups, the arylheteroarylamine group is a monocyclic aryl group (heteroaryl group), a polycyclic aryl group (heteroaryl group), or a monocyclic aryl group (hetero) aryl group) and a polycyclic aryl group (heteroaryl group) may be included at the same time. In addition, the aryl group and the heteroaryl group in the arylamine group and the arylheteroarylamine group may be selected from the examples of the above-described aryl group and heteroaryl group.

The organic light emitting compound according to the present invention represented by the above [Formula I] can be used as various organic layers such as a hole transport layer, an electron transport layer, and a light emitting layer in an organic light emitting device due to its structural specificity, and in particular as a light efficiency improving layer material provided in the device can be used

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

As such, the organic light emitting compound according to the present invention can synthesize an organic light emitting compound having various characteristics by using a characteristic skeleton exhibiting intrinsic properties and a moiety having intrinsic properties introduced thereto, As a result, when the organic light emitting compound according to the present invention is applied as a material for various organic layers such as a hole transport layer, or, in particular, when applied to a light efficiency improving layer provided in a device, it is possible to further improve light emitting characteristics such as luminous efficiency of the device.

The organic light emitting device according to an embodiment of the present invention may have a structure including a first electrode and a second electrode and an organic layer disposed therebetween. Except that, it may be manufactured using conventional device manufacturing methods and materials.

The organic layer of the organic light emitting diode according to the present invention may have a single layer structure, but may have a multilayer 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 improving layer (Capping layer), and the like. However, the present invention is not limited thereto and may include a smaller number or a larger number of organic layers.

In addition, the organic electroluminescent 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 improving layer, wherein the light efficiency improving layer is a lower portion of the first electrode ( Bottom emission) or on the second electrode top (Top emission).

In the method of forming the second electrode on top (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 improvement layer (CPL) formed of the compound according to the present invention having a relatively high refractive index. The wavelength of is amplified and thus the light efficiency is increased .

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

In addition, the organic light emitting compound according to the present invention and the organic light emitting device including the same can be applied to the device according to a general organic light emitting device manufacturing method.

The organic light emitting device according to the present invention uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate. It can be prepared by forming 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 diode 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 in a smaller number by a solvent process rather than a deposition method using various polymer materials, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.

As the anode material, a material having a large 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, gold, or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc. 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) , a conductive polymer such as polypyrrole and polyaniline, but is not limited thereto.

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

The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and 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 porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene, quinacridone-based organic material, perylene-based organic material, 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 is suitable, and a material having high hole mobility is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together. can be further improved.

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, benzoxazole, benzthiazole and There are benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, rubrene, and the like, but is not limited thereto.

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

The organic light emitting diode according to the present invention may be a top emission type, a back emission type, or a double-sided emission type depending on the material used.

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

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for explaining the present invention in more detail, the scope of the present invention is not limited thereby, and it is common in the art that various changes and modifications are possible within the scope and spirit of the present invention. It will be self-evident to those with knowledge.

Synthesis example 1: Synthesis of compound 47

(One) Preparation Example 1 : Synthesis of intermediate 47-1

100 ml of Acetone was added to 4-Chloro-2-iodonaphthalen-1-ol (10.0 g, 0.033 mol) and K ₂ CO ₃ (6.4 g, 0.046 mol), and dimethyl sulfate (9.2 g, 0.043 mol) was slowly added dropwise. Thereafter, the reaction was stirred at 55° C. for 1 hour. After completion of the reaction, 7.9 g (yield 75.5%) of <Intermediate 47-1> was obtained after extraction and concentration.

(2) production example 2: Synthesis of intermediate 47-2

2-Bromo-6-chlorophenylboronic acid (10.0 g, 0.043 mol), intermediate 47-1 (16.3 g, 0.051 mol), K ₂ CO ₃ (17.6 g, 0.128 mol), Pd(PPh ₃ ) ₄ (1.0 g, 0.001 mol) was added 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, 8.5 g (yield 52.3%) of <Intermediate 47-2> was obtained by extraction, concentration, and column.

(3) production example 3: Synthesis of intermediate 47-3

Intermediate 47-2 (10.0 g, 0.026 mol) was dissolved in 60 mL of Anhydrous DCM, and then BBr ₃ (in DCM, 8.2 g, 0.033 mol) was added dropwise while maintaining 0 °C. Thereafter, the reaction was stirred at 25 °C for 16 hours. After completion of the reaction, the mixture was extracted with diethyl ether, concentrated, and columned to obtain 7.6 g (yield 78.9%) of <Intermediate 47-3>.

(4) production example 4: Synthesis of intermediate 47-4

Intermediate 47-3 (10.0 g, 0.027 mol), Et ₃ N in dichloromethane (3.7 g, 0.057 mol) at -70 ° C. Tf ₂ O (3.9 g, 0.030 mol) was added dropwise dropwise. After slowly raising the temperature to room temperature, the reaction was stirred for 12 hours. After completion of the reaction, 10.1 g (yield 74.3%) of <Intermediate 47-4> was obtained by extraction, concentration, and column.

(5) production example 5: Synthesis of intermediate 47-5

1-Adamantylamine (10.0 g, 0.066 mol), Intermediate 47-4 (33.1 g, 0.066 mol), rac-BINOL (7.6 g, 0.026 mol), Cs ₂ CO ₃ (27.4 g 0.198 mol), CuI (2.5 g, 0.013 mol), 150 mL of DMF was added, and the reaction was stirred at 80 °C for 24 hours. After completion of the reaction, 18.7 g (yield 67.3%) of <Intermediate 47-5> was obtained by extraction and concentration, followed by column and recrystallization.

(6) production example 6: Synthesis of compound 47

Intermediate 47-5 (10.0 g, 0.024 mol), 2-(Trifluoromethyl)naphthalene-6-boronic acid (13.7 g, 0.057 mol), K ₂ CO ₃ (19.7 g, 0.143 mol), X-phos (1.1 g, 0.002 mol), Pd(OAc) ₂ (1.4 g, 0.001 mol) was added with 180 mL of THF and 45 mL of H ₂ O, followed by stirring at 90° C. for 6 hours to react. After completion of the reaction, 10.3 g (yield 58.5%) of <Compound 47> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=739 [(M+1) ⁺ ]

Synthesis example 2: Synthesis of compound 63

(One) production example 1: Synthesis of intermediate 63-1

100 mL of Acetone was added to 3-Iodonaphthalen-2-ol (10.0 g, 0.037 mol) and K ₂ CO ₃ (7.2 g, 0.052 mol), and dimethyl sulfate (10.4 g, 0.048 mol) was slowly added dropwise. Thereafter, the reaction was stirred at 55° C. for 1 hour. After completion of the reaction, 8.4 g (yield 79.9%) of <Intermediate 63-1> was obtained after extraction and concentration.

(2) production example 2: Synthesis of intermediate 63-2

2-Bromo-4-chlorophenylboronic acid (10.0 g, 0.043 mol), intermediate 63-1 (14.5 g, 0.051 mol), K ₂ CO ₃ (17.6 g, 0.128 mol), Pd(PPh ₃ ) ₄ (1.0 g, 0.001 mol) was added 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, 7.4 g (yield 50.1%) of <Intermediate 63-2> was obtained by extraction, concentration, and column.

(3) production example 3: Synthesis of intermediate 63-3

Intermediate 63-2 (10.0 g, 0.029 mol) was dissolved in 60 mL of Anhydrous DCM, and then BBr ₃ (in DCM, 9.0 g, 0.036 mol) was added dropwise while maintaining 0 °C. Thereafter, the reaction was stirred at 25 °C for 16 hours. After completion of the reaction, the mixture was extracted with diethyl ether, concentrated, and then columned to obtain 7.2 g (yield 75.0%) of <Intermediate 63-3>.

(4) production example 4: Synthesis of intermediate 63-4

Intermediate 63-3 (10.0 g, 0.030 mol), Et ₃ N in dichloromethane (4.0 g, 0.063 mol) at -70 ° C. Tf ₂ O (4.3 g, 0.033 mol) was added dropwise dropwise. After slowly raising the temperature to room temperature, the reaction was stirred for 12 hours. After completion of the reaction, 10.4 g (yield 74.5%) of <Intermediate 63-4> was obtained by extraction, concentration, and column.

(5) production example 5: Synthesis of intermediate 63-5

1-Adamantylamine (10.0 g, 0.066 mol), Intermediate 63-4 (30.8 g, 0.066 mol), rac-BINOL (7.6 g, 0.026 mol), Cs ₂ CO ₃ (27.4 g, 0.198 mol), CuI (2.5 g) , 0.013 mol) was added with 150 mL of DMF, and reacted by stirring at 80 °C for 24 hours. After completion of the reaction, 15.2 g (yield 59.6%) of <Intermediate 63-5> was obtained by extraction and concentration, followed by column and recrystallization.

(6) production example 6: Synthesis of compound 63

Intermediate 63-5 (10.0 g, 0.026 mol), 3,5-Di-tert-butylphenylboronic acid (7.3 g, 0.031 mol), K ₂ CO ₃ (10.7 g, 0.078 mol), X-phos (1.2 g, 0.003) mol), Pd(OAc) ₂ (1.5 g, 0.001 mol) was added with 180 mL of THF and 45 mL of H ₂ O, followed by stirring at 90° C. for 6 hours. After completion of the reaction, 8.8 g (yield 62.9%) of <Compound 63> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=539 [(M+1) ⁺ ]

Synthesis example 3: Synthesis of compound 92

(One) production example 1: Synthesis of intermediate 92-1

Intermediate 63-3 (10.0 g, 0.026 mol), Bis(pinacolato)diboron (7.9 g, 0.031 mol), CH ₃ COOK (5.1 g, 0.052 mol), Pd(dba) ₂ (0.6 g, 0.001 mol), X -Phos (0.7 g, 0.001 mol) was put in THF and reacted by stirring at 100 °C for 12 hours under nitrogen gas. After completion of the reaction, 8.9 g (yield 71.9%) of <Intermediate 92-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) production example 2: Synthesis of compound 92

4-(Biphenyl-4-yl)-6-phenyl-1,3,5-triazin-2-ylboronic acid (10.0 g, 0.029 mol), Intermediate 92-1 (16.7 g, 0.035 mol), K ₂ CO ₃ (12.1 g, 0.087 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.001 mol) was added with 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, 12.2 g (yield 63.7%) of <Compound 92> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=658[(M+1) ⁺ ]

Synthesis example 4: Synthesis of compound 98

(One) production example 1: Synthesis of intermediate 98-1

4-Bromobiphenyl (10.0 g, 0.043 mol), 9,9'-Spirobi[fluoren]-2-amine (21.3 g, 0.064 mol), NaO ^t Bu (8.3 g, 0.086 mol), Pd(dba) ₂ (1.2 g, 0.002 mol), t-Bu ₃ P (0.9 g, 0.004 mol) was added with 120 mL of Toluene and stirred at 100 °C for 6 hours to react. After completion of the reaction, 16.2 g (yield 78.1%) of <Intermediate 98-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) production example 2: Synthesis of compound 98

Intermediate 63-3 (10.0 g, 0.026 mol), Intermediate 98-1 (18.8 g, 0.039 mol), NaO ^t Bu (5.0 g, 0.052 mol), Pd(dba) ₂ (0.7 g, 0.001 mol), t- 120 mL of Toluene was added to Bu ₃ P (0.5 g, 0.003 mol), and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, 11.6 g (yield 53.7%) of <Compound 98> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=832 [(M+1) ⁺ ]

Synthesis example 5: Synthesis of compound 117

(One) production example 1: Synthesis of intermediate 117-1

100 mL of Acetone was added to 1-Iodo-2-naphthol (10.0 g, 0.037 mol) and K ₂ CO ₃ (7.2 g, 0.052 mol), and dimethyl sulfate (10.4 g, 0.048 mol) was slowly added dropwise. Thereafter, the reaction was stirred at 55° C. for 1 hour. After completion of the reaction, 8.6 g (yield 81.8%) of <Intermediate 117-1> was obtained after extraction and concentration.

(2) production example 2: Synthesis of intermediate 117-2

2-Bromo-4-chlorophenylboronic acid (10.0 g, 0.043 mol), intermediate 117-1 (14.5 g, 0.051 mol), K ₂ CO ₃ (17.6 g, 0.128 mol), Pd(PPh ₃ ) ₄ (1.0 g, 0.001 mol) was added 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, 8.2 g (yield 55.5%) of <Intermediate 117-2> was obtained by extraction, concentration, and column.

(3) production example 3: Synthesis of intermediate 117-3

Intermediate 117-2 (10.0 g, 0.029 mol) was dissolved in 60 ml of Anhydrous DCM, and then BBr ₃ (in DCM, 9.0 g, 0.036 mol) was added dropwise while maintaining 0 °C. Thereafter, the reaction was stirred at 25 °C for 16 hours. After completion of the reaction, the mixture was extracted with diethyl ether, concentrated, and columned to obtain 7.1 g (yield 74.0%) of <Intermediate 117-3>.

(4) production example 4: Synthesis of intermediate 117-4

Intermediate 117-3 (10.0 g, 0.030 mol), Et ₃ N in dichloromethane (4.0 g, 0.063 mol) at -70 ° C. Tf ₂ O (4.3 g, 0.033 mol) was added dropwise dropwise. After slowly raising the temperature to room temperature, the reaction was stirred for 12 hours. After completion of the reaction, 10.2 g (yield 73.1%) of <Intermediate 117-4> was obtained by extraction, concentration, and column.

(5) production example 5: Synthesis of intermediate 117-5

1-Adamantylamine (10.0 g, 0.066 mol), Intermediate 117-4 (30.8 g, 0.066 mol), rac-BINOL (7.6 g, 0.026 mol), Cs ₂ CO ₃ (27.4 g 0.198 mol), CuI (2.5 g, 0.013 mol), 150 mL of DMF was added, and the reaction was stirred at 80 °C for 24 hours. After completion of the reaction, 15.8 g (yield 61.9%) of <Intermediate 117-5> was obtained by extraction and concentration, followed by column and recrystallization.

(6) production example 6: Synthesis of compound 117

Intermediate 117-5 (10.0 g, 0.026 mol), 2-(4-Dibenzothienyl)phenylboronic acid (9.5 g, 0.031 mol), K ₂ CO ₃ (10.7 g, 0.078 mol), X-phos (1.2 g, 0.003 mol) ), Pd(OAc) ₂ (1.5 g, 0.001 mol) was added with 180 mL of THF and 45 mL of H ₂ O, followed by stirring at 90° C. for 6 hours. After completion of the reaction, 9.5 g (yield 60.1%) of <Compound 117> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=609[(M+1) ⁺ ]

Synthesis example 6: Synthesis of compound 161

(One) production example 1: Synthesis of intermediate 161-1

(1-Bromonaphthalen-2-yl)boronic acid (10.0 g, 0.040 mol), intermediate 47-1 (15.2 g, 0.048 mol), K ₂ CO ₃ (16.5 g, 0.120 mol), Pd(PPh ₃ ) ₄ ( 0.9 g, 0.001 mol) was added 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, 8.9 g (yield 56.2%) of <Intermediate 161-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of intermediate 161-2

Intermediate 161-1 (10.0 g, 0.025 mol) was dissolved in 60 mL of Anhydrous DCM, and then BBr ₃ (in DCM, 7.9 g, 0.031 mol) was added dropwise while maintaining 0 °C. Thereafter, the reaction was stirred at 25 °C for 16 hours. After completion of the reaction, 7.7 g (yield 79.8%) of <Intermediate 161-2> was obtained by extraction with diethyl ether, concentration, and column.

(3) production example 3: Synthesis of intermediate 161-3

Intermediate 161-2 (10.0 g, 0.026 mol), Et ₃ N in dichloromethane (3.5 g, 0.055 mol) at -70 ° C. Tf ₂ O (3.7 g, 0.029 mol) was added dropwise dropwise. After slowly raising the temperature to room temperature, the reaction was stirred for 12 hours. After completion of the reaction, 9.8 g (yield 72.9%) of <Intermediate 161-3> was obtained by extraction, concentration, and column.

(4) production example 4: Synthesis of intermediate 161-4

1-Adamantylamine (10.0 g, 0.066 mol), Intermediate 161-3 (34.1 g, 0.066 mol), rac-BINOL (7.6 g, 0.026 mol), Cs ₂ CO ₃ (27.4 g 0.198 mol), CuI (2.5 g, 0.013 mol), 150 mL of DMF was added, and the reaction was stirred at 80 °C for 24 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 20.1 g (yield 69.7%) of <Intermediate 161-4>.

(5) production example 5: Synthesis of compound 161

Intermediate 161-4 (10.0 g, 0.023 mol), (9,9-Diphenyl-9H-fluoren-2-yl)-boronic acid (10.0 g, 0.028 mol), K ₂ CO ₃ (9.5 g, 0.069 mol), X-phos (1.1 g, 0.002 mol), Pd(OAc) ₂ (1.3 g, 0.001 mol) was added with 180 mL of THF and 45 mL of H ₂ O, followed by stirring at 90° C. for 6 hours to react. After completion of the reaction, 9.7 g (yield 58.9%) of <Compound 161> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=717 [(M+1) ⁺ ]

Synthesis example 7: Synthesis of compound 230

(One) production example 1: Synthesis of intermediate 230-1

(3-Bronaphthalen-2-yl)boronic acid (10.0 g, 0.040 mol), intermediate 63-1 (13.6 g, 0.048 mol), K ₂ CO ₃ (16.5 g, 0.120 mol), Pd(PPh ₃ ) ₄ ( 0.9 g, 0.001 mol) was added 200 mL of Toluene, 50 mL of Ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, 6.1 g (yield 42.1%) of <Intermediate 230-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of intermediate 230-2

Intermediate 230-1 (10.0 g, 0.028 mol) was dissolved in 60 mL of Anhydrous DCM, and then BBr ₃ (in DCM, 8.6 g, 0.034 mol) was added dropwise while maintaining 0 °C. Thereafter, the reaction was stirred at 25 °C for 16 hours. After completion of the reaction, the mixture was extracted with diethyl ether, concentrated and then columned to obtain 7.3 g (yield 75.9%) of <Intermediate 230-2>.

(3) production example 3: Synthesis of intermediate 230-3

Intermediate 230-2 (10.0 g, 0.029 mol), Et ₃ N in dichloromethane (3.9 g, 0.060 mol) at -70 ° C. Tf ₂ O (4.1 g, 0.032 mol) was added dropwise dropwise. After slowly raising the temperature to room temperature, the reaction was stirred for 12 hours. After completion of the reaction, 9.7 g (yield 70.4%) of <Intermediate 230-3> was obtained by extraction and concentration, followed by column and recrystallization.

(4) production example 4: Synthesis of compound 230

1-Adamantylamine (10.0 g, 0.066 mol), Intermediate 230-3 (31.8 g, 0.066 mol), rac-BINOL (7.6 g, 0.026 mol), Cs ₂ CO ₃ (27.4 g 0.198 mol), CuI (2.5 g, 0.013 mol), 150 mL of DMF was added, and the reaction was stirred at 80 °C for 24 hours. After completion of the reaction, 19.2 g (yield 72.3%) of <Compound 230> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=401[(M+1) ⁺ ]

Device embodiment (capping layer)

In an embodiment according to the present invention, the ITO transparent electrode was cleaned after patterning so that the light emitting area was 2 mm × 2 mm using an ITO glass substrate containing Ag of 25 mm × 25 mm × 0.7 mm. After mounting the substrate in a vacuum chamber, the base pressure was 1 × 10 ^-6 torr or more, and the organic material and the metal were deposited on the Ag-containing ITO glass substrate in the following structure.

Device Examples 1 to 20

By employing the compound implemented according to the present invention in the light efficiency improving layer, an organic light emitting device having the following device structure was manufactured, and light emission characteristics including light emission efficiency were measured.

Ag/ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (α-NPB, 100 nm) / electron blocking layer (TCTA, 10 nm) / light emitting layer (20 nm) / electron transport layer (201: Liq, 30 nm) / LiF (1 nm) / Mg:Ag (15 nm) / Light efficiency improvement layer (70 nm)

HAT-CN was formed to a thickness of 5 nm to form a hole injection layer on an ITO transparent electrode containing Ag on a glass substrate, and then α-NPB was formed into a film of 100 nm for the hole transport layer. The electron blocking layer was formed of TCTA with a thickness of 10 nm. In addition, the light emitting layer was co-deposited at 20 nm using BH1 as a host compound and BD1 as a dopant compound. In addition, an electron transport layer (50% doped with [201] compound Liq below) was formed to a thickness of 30 nm and LiF 1 nm. Then, a film of 15 nm was formed of Mg:Ag in a ratio of 1:9. And as the light efficiency improvement layer (capping layer) compound, compounds 47, 48, 51, 54, 61, 63, 81, 92, 98, 99, 117, 137, 143, 161, 171, 196, 200 implemented in the present invention , 230, 239, and 307 were deposited to a thickness of 70 nm to fabricate an organic light emitting diode.

Device Comparative Example 1

The organic light emitting device for Device Comparative Example 1 was manufactured in the same manner except that the light efficiency improving layer was not used in the device structures of Examples 1 to 20.

Device Comparative Example 2

The organic light emitting device for Device Comparative Example 2 was manufactured in the same manner except that Alq ₃ was used instead of the compound according to the present invention as the light efficiency improving layer compound in the device structures of Examples 1 to 20.

Experimental Example 1: Light emitting characteristics of Device Examples 1 to 20

The organic light emitting device manufactured according to the above example was measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research) to measure driving voltage, current efficiency, and color coordinates, and the result value based on 1,000 nits is shown in [Table 1] below.

Example Light Efficiency Improvement Layer V cd/A CIEx CIEy One Formula 47 3.5 8.8 0.136 0.057 2 Formula 48 3.8 8.4 0.139 0.055 3 Formula 51 4.0 8.0 0.141 0.050 4 Formula 54 3.9 8.0 0.142 0.047 5 Formula 61 4.0 8.0 0.143 0.050 6 Formula 63 3.7 8.6 0.141 0.053 7 Formula 81 3.8 8.4 0.139 0.056 8 Formula 92 4.0 8.0 0.142 0.048 9 Formula 98 3.9 8.0 0.142 0.047 10 Formula 99 3.5 8.7 0.138 0.056 11 Formula 117 3.7 8.6 0.141 0.056 12 Formula 137 3.8 8.4 0.140 0.054 13 Formula 143 3.5 8.8 0.136 0.059 14 Formula 161 3.8 8.4 0.141 0.052 15 Formula 171 4.0 8.0 0.141 0.043 16 Formula 196 3.9 8.0 0.142 0.045 17 Formula 200 4.0 8.0 0.141 0.052 18 Formula 230 3.7 8.6 0.141 0.056 19 Formula 239 3.8 8.4 0.141 0.050 20 Formula 307 3.8 8.3 0.142 0.050 Comparative Example 1 not used 4.5 7.0 0.151 0.140 Comparative Example 2 Alq ₃ 4.3 7.8 0.145 0.063

Looking at the results shown in [Table 1], when the compound according to the present invention is employed in the light efficiency improving layer provided in the organic light emitting device, the device without the conventional light efficiency improving layer and the compound used as the conventional light efficiency improving layer material It can be seen that the driving voltage is reduced and the current efficiency is improved compared to the devices employing ? (Comparative Examples 1 and 2).

[HAT-CN] [α-NPB] [BH1] [BD1] [201]

[TCTA]

Claims (11)

An organic light emitting compound represented by the following [Formula I]:
[Formula Ⅰ]

In the [Formula I],
A ₁ and A ₂ are the same as or different from each other, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms,
At least one of A ₁ and A ₂ is a substituted or unsubstituted 10 to 50 aromatic hydrocarbon ring,
A ₁ and A ₂ are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 2 to C 20 alkenyl group, a substituted or unsubstituted A cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 20 carbon atoms, substituted Or an unsubstituted C1 to C20 halogenated alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C6 to C30 of an arylamine group, a substituted or unsubstituted heteroarylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted arylheteroarylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, and It has at least one substituent selected from a substituted or unsubstituted C6-C30 arylsilyl group. According to claim 1,
wherein A ₁ and A ₂ are each independently selected from the following [Structural Formula 1] to [Structural Formula 3], and at least one of A ₁ and A ₂ is selected from the following [Structural Formula 2] to [Structural Formula 3] An organic light-emitting compound comprising:
[Structural formula 1] [Structural formula 2] [Structural formula 3]

In the [Structural Formula 1] to [Structural Formula 3],
R ₁ to R ₃ are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 2 to C 20 alkenyl group, a substituted or unsubstituted carbon number A cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 20 carbon atoms, substituted or An unsubstituted C1 to C20 halogenated alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C6 to C30 An arylamine group, a substituted or unsubstituted heteroarylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted arylheteroarylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, and a substituted or an unsubstituted C6-C30 arylsilyl group,
n is an integer from 0 to 4, m is an integer from 0 to 6, l is an integer from 0 to 6, and when n, m and l are 2 or more, a plurality of R ₁ to R ₃ are the same as or different from each other, respectively. and
'*' indicates a site binding to the [Formula I]. 3. The method of claim 1 or 2,
In the definition of A ₁ , A ₂ , R ₁ to R ₃ , 'substituted or unsubstituted' means deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, an amine group, a silyl group, an alkyl group, a cycloalkyl group, or an alkoxy group. It is characterized in that it is substituted with one or two or more substituents selected from the group consisting of a group, an alkenyl group, an aryl group, a heteroaryl group and a silyl group, or is substituted with a substituent to which two or more substituents are connected among the substituents, or does not have any substituents an organic light emitting compound. According to claim 1,
The [Formula I] is an organic light emitting compound, characterized in that selected from the following [Compound 1] to [Compound 316]:

An organic light emitting device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode,
At least one of the organic layers is an organic light emitting device comprising an organic light emitting compound represented by [Formula I] according to claim 1. 6. The method of claim 5,
The organic layer is selected from a hole injection layer, a hole transport layer, a layer that performs both hole injection and hole transport functions, an electron transport layer, an electron injection layer, a layer that performs both electron transport and electron injection functions, an electron blocking layer, a hole blocking layer and a light emitting layer including one or more floors that become
At least one of the layers comprises an organic light emitting compound represented by the [Formula I]. 7. The method of claim 6,
An organic light emitting device comprising an organic light emitting compound represented by the [Formula I] in the electron transport layer or a layer that performs both electron transport and electron injection functions. 7. The method of claim 6,
An organic light emitting device comprising an organic light emitting compound represented by the [Formula I] in the hole transport layer or a layer that performs both hole injection and hole transport functions. 7. The method of claim 6,
An organic light emitting device comprising an organic light emitting compound represented by the [Formula I] in the light emitting layer. 6. The method of claim 5,
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, characterized in that it comprises an organic light emitting compound represented by the [Formula I]. 11. The method of claim 10,
The light efficiency improving layer is an organic light emitting device, characterized in that formed on at least one of a lower portion of the first electrode or an upper portion of the second electrode.