Organic compound and electroluminescent device comprising the same

Abstract

The present invention relates to an organic compound represented by the following [Chemical Formula I] and an organic light-emitting device comprising the same, which is employed in a light efficiency improvement layer provided in an organic light-emitting device to realize low voltage driving of the device and light-emitting characteristics such as excellent color purity and light-emitting efficiency. [Chemical Formula I]

Description

Technology Field

[0001] The present invention relates to an organic compound characterized by being employed as a capping layer material for improving light efficiency in an organic light-emitting diode, and to an organic light-emitting diode in which the light-emitting characteristics, such as low-voltage driving of the device and excellent light-emitting efficiency, are significantly improved by employing the same. Background Technology

[0002] Organic light-emitting diodes (OLEDs) can be formed on transparent substrates, and compared to plasma display panels or inorganic light-emitting diode (EL) displays, they have the advantages of being able to operate at a low voltage of 10 V or less, consuming relatively little power, and having excellent color quality, and can display three colors of green, blue, and red, so they have recently become the subject of much interest as next-generation display devices.

[0003] However, for such organic light-emitting diodes to exhibit the characteristics described above, it is necessary for the materials forming the organic layer within the device—such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials—to be supported by stable and efficient materials; yet, the development of stable and efficient organic layer materials for organic light-emitting diodes has not yet been sufficiently achieved.

[0004] Therefore, in order to realize more stable organic light-emitting diodes and to achieve high efficiency, long lifespan, and large scale, further improvements in efficiency and lifespan characteristics are required; in particular, there is an urgent need for the development of materials constituting each organic layer of the organic light-emitting diode.

[0005] Furthermore, recently, in addition to research on improving the characteristics of organic light-emitting diodes by varying the performance of each organic layer material, technologies for enhancing color purity and increasing luminous efficiency through optimized optical thickness between the anode and cathode are being recognized as important factors in improving device performance. As an example of such a method, a capping layer is used on the electrode to achieve increased light efficiency and excellent color purity. The problem to be solved

[0006] Accordingly, the present invention aims to provide a novel organic compound that can be employed in a light efficiency improvement layer provided in an organic light-emitting device to realize excellent light-emitting characteristics, such as low-voltage driving of the device and improved light-emitting efficiency, and an organic light-emitting device including the same. means of solving the problem

[0007] To solve the above problem, the present invention provides an organic compound represented by the following [Chemical Formula I].

[0008] [Chemical Formula I]

[0009]

[0010] The characteristic structure of the above [Chemical Formula I] and the specific compounds, R1, R2, Ar1, and Ar2, realized by it will be described later.

[0012] In addition, the present invention provides 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, wherein the organic light-emitting device further comprises 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, and wherein the light efficiency improvement layer comprises an organic compound represented by [Chemical Formula I]. Effects of the invention

[0013] The organic compound according to the present invention is employed as a material for a light efficiency improvement layer provided in an organic light-emitting diode, and can realize improved light emission characteristics such as low-voltage driving of the organic light-emitting diode, excellent light emission efficiency, and color purity, so it can be usefully used in various lighting and display devices. Specific details for implementing the invention

[0014] The present invention will be described in more detail below.

[0015] The present invention relates to an organic compound represented by the following [Chemical Formula I], which is employed as a material for improving light efficiency in an organic light-emitting diode and can achieve low-voltage operation of the diode and light-emitting characteristics such as excellent light-emitting efficiency and color purity.

[0016] [Chemical Formula I]

[0017]

[0018] In the above [Chemical Formula I],

[0019] (i) R1 and R2 are identical or different from each other and are each independently selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted deuterated alkyl group having 1 to 20 carbon atoms.

[0020] In addition, the above R1 and R2 can be connected to each other to form a ring, and specifically, the structure may be as follows.

[0021]

[0022]

[0024] (ii) Ar1 and Ar2 are identical or different from each other, and independently, Ar1 and Ar2 are selected from an aryl group having 6 to 30 carbon atoms substituted with one or more substituents, a heteroaryl group having 3 to 30 carbon atoms substituted with one or more substituents, and the following [Structural Formula 1].

[0025] In addition, the above one or more substituents may be selected from deuterium, halogen group, alkyl group, halogenated alkyl group, deuteriumated alkyl group, cycloalkyl group, heterocycloalkyl group, alkoxy group, halogenated alkoxy group, deuteriumated alkoxy group, alkylsilyl group, arylsilyl group, and the following [Structural Formula 1].

[0026] [Structural Formula 1]

[0027]

[0028] In the above [Structural Formula 1],

[0029] R is independently selected within each structure from hydrogen, deuterium, halogen group, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C1 to C20 alkoxy group, substituted or unsubstituted C1 to C20 halogenated alkyl group, substituted or unsubstituted C1 to C20 halogenated alkoxy group, substituted or unsubstituted C3 to C20 cycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, and substituted or unsubstituted C2 to C30 heteroaryl group, and in each structure of [Structural Formula 1], a plurality of R are identical or different from each other.

[0030] In addition, according to one embodiment of the present invention, Ar1 and Ar2 may be selected from a phenyl group substituted with one or more substituents, a substituted biphenyl group substituted with a naphthyl group, a substituted pyridinyl group, and [Structural Formula 1].

[0032] (iii) In the definitions of R, R1 and R2 above, "substituted or unsubstituted" means that R, R1 and R2 are each substituted with one or more substituents selected from deuterium, halogen group, alkyl group, halogenated alkyl group, deuteriumated alkyl group, cycloalkyl group, heterocycloalkyl group, alkoxy group, halogenated alkoxy group, deuteriumated alkoxy group, aryl group, heteroaryl group, alkylsilyl group and arylsilyl group, or are substituted with a substituent in which two or more of the substituents are connected, or have no substituents.

[0033] For example, the term "substituted aryl group" means that the phenyl group, biphenyl group, naphthalene group, fluorenyl group, pyrenyl group, phenanthrenyl group, perylene group, tetracenyl group, anthracenyl group, etc., are substituted with the above-mentioned substituents.

[0034] In addition, the term "substituted heteroaryl group" means that pyridyl groups, thiophenyl groups, triazine groups, quinoline groups, phenanthroline groups, imidazole groups, thiazole groups, oxazole groups, carbazole groups, and condensed heteroaryl groups thereof, such as benzquinoline groups, benzimidazole groups, benzoxazole groups, benzthiazole groups, benzcarbazole groups, dibenzothiophenyl groups, dibenzofuran groups, etc., are substituted with such substituents.

[0036] In the present invention, examples of the substituents are described in detail below, but are not limited thereto.

[0037] In the present invention, the alkyl group may be a straight chain or a 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, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, an n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cycloheptylmethyl group, an octyl group, an n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group. There are, but are not limited to, 2-propylpentyl groups, n-nonyl groups, 2,2-dimethylheptyl groups, 1-ethyl-propyl groups, 1,1-dimethyl-propyl groups, isohexyl groups, 2-methylpentyl groups, 4-methylhexyl groups, 5-methylhexyl groups, etc.

[0038] In the present invention, the alkoxy group may be a straight chain or a branched chain. Specifically, it may be a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an i-propyloxy group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, an n-pentyloxy group, a neopentyloxy group, an isopentyloxy group, an n-hexyloxy group, a 3,3-dimethylbutyloxy group, a 2-ethylbutyloxy group, an n-octyloxy group, an n-nonyloxy group, an n-decyloxy group, a benzyloxy group, a p-methylbenzyloxy group, etc., but is not limited thereto.

[0039] In the present invention, the alkyl group or alkoxy group may be substituted with deuterium, a halogen group, etc., to become a deuterated alkyl group or alkoxy group, or a halogenated alkyl group or alkoxy group.

[0040] In the present invention, the aryl group may be monocyclic or polycyclic, and although the number of carbon atoms is not particularly limited, it is preferably 6 to 30. Additionally, it includes a polycyclic aryl group structure fused with cycloalkyl, etc. Examples of monocyclic aryl groups include phenyl groups, biphenyl groups, terphenyl groups, stilbene groups, etc. Examples of polycyclic aryl groups include naphthyl groups, anthracenyl groups, phenanthrenyl groups, pyrenyl groups, perylenyl groups, tetracenyl groups, chrysenyl groups, fluorenyl groups, acenaphthacenyl groups, triphenylene groups, fluoranthrene groups, etc., but the scope of the present invention is not limited only to these examples.

[0041] In the present invention, the fluorenyl group is a structure in which two ring organic compounds are connected through one atom, examples include , , There are others.

[0042] In the present invention, the fluorenyl group comprises a structure of an open fluorenyl group, wherein the open fluorenyl group is a structure in which the connection of one ring compound is broken in a structure in which two ring organic compounds are connected through one atom, examples include , There are others.

[0043] In addition, the carbon atoms of the above ring may be substituted with one or more heteroatoms selected from N, S, and O, examples include , , , There are others.

[0044] In the present invention, the heteroaryl group is a heterocyclic group comprising O, N, or S as a heteroatom, and although the number of carbon atoms is not particularly limited, it is preferably 3 to 30 carbon atoms, and comprises a polycyclic heteroaryl group structure fused with cycloalkyl or heterocycloalkyl, etc. 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, a bipyridyl group, a pyrimidyl group, a triazine group, a triazole group, an acryl group, a pyridazine group, a pyrazinyl group, a quinolinyl group, a quinazolin group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an indole group, a carbazole group, Benzooxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophen group, dibenzothiophen group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, isooxazolyl group, oxadiazoyl group, thiadiazolyl group, benzothiazoyl group, phenothiazinyl group, phenoxazine group, phenothiazine group, etc., are included, but are not limited to these.

[0045] In the present invention, the amine group may be -NH2, an alkylamine group, an arylamine group, a heteroarylamine group, an aryl-heteroarylamine group, etc., and the aryl (heteroaryl)amine group refers to an amine substituted with an aryl group and / or a heteroaryl group, and the alkylamine group refers to an amine substituted with an alkyl group. Examples of the aryl (heteroaryl)amine group include a substituted or unsubstituted mono-aryl (heteroaryl)amine group, a substituted or unsubstituted di-aryl (heteroaryl)amine group, or a substituted or unsubstituted tri-aryl (heteroaryl)amine group. The aryl group and the heteroaryl group among the aryl (heteroaryl)amine group are identical to the definitions of the aryl group and the heteroaryl group, and the alkyl group of the alkylamine group is also identical to the definition of the alkyl group.

[0046] Examples of the above arylamine groups include, but are not limited to, phenylamine groups, naphthylamine groups, biphenylamine groups, anthracenylamine groups, 3-methyl-phenylamine groups, 4-methyl-naphthylamine groups, 2-methyl-biphenylamine groups, 9-methyl-anthracenylamine groups, diphenylamine groups, phenylnaphthylamine groups, ditolylamine groups, phenyltolylamine groups, and triphenylamine groups.

[0047] 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, an aryl group, etc. Specific examples of such silyl groups include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, etc., but are not limited thereto.

[0048] Specific examples of halogen groups used as substituents in the present invention include fluorine (F), chlorine (Cl), bromine (Br), etc.

[0049] In the present invention, the cycloalkyl group refers to a monocyclic, polycyclic, and spiroalkyl radical, and includes the same, preferably containing a cyclic carbon atom having 3 to 20 carbon atoms, including cyclopropyl, cyclopentyl, cyclohexyl, bicycloheptyl, spirodecyl, spirondecyl, adamantyl, etc., and the cycloalkyl group may be optionally substituted.

[0050] In the present invention, the heterocycloalkyl group refers to an aromatic and non-aromatic cyclic radical containing one or more heteroatoms, and includes the above, wherein one or more heteroatoms are selected from O, S, N, P, B, Si, and Se, preferably O, N or S, and specifically, when N is included, may be aziridine, pyrrolidine, piperidine, azephan, azocan, etc.

[0052] The organic compound according to the present invention represented by [Chemical Formula I] above can be used as a material for a capping layer that improves light efficiency in an organic light-emitting diode due to its structural specificity.

[0053] Preferred embodiments of the organic compound represented by [Chemical Formula I] according to the present invention include the following compounds, but are not limited thereto.

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0072] In this way, the organic compound according to the present invention can synthesize organic compounds having various characteristics by utilizing a moiety having unique characteristics, and as a result, when the organic compound according to the present invention is applied to a light efficiency improvement layer provided in an organic light-emitting device, the light emission characteristics such as the light emission efficiency of the device can be further improved.

[0074] In addition, the compound of the present invention can be applied to a device according to a general method for manufacturing an organic light-emitting device, and an organic light-emitting device according to one embodiment of the present invention may be formed with a structure including a first electrode, a second electrode, and an organic layer disposed between them, and may be manufactured using a conventional method and materials for manufacturing a device, except that the organic compound according to the present invention is used in the organic layer of the device.

[0075] The organic layer of the organic light-emitting diode according to the present invention may be formed as a single layer structure, but may also be formed as 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 improvement layer (Capping layer), etc. However, it is not limited thereto and may include a smaller or larger number of organic layers.

[0077] An organic light-emitting device according to one embodiment of the present invention comprises 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 may be formed at the bottom of the first electrode (bottom emission) or at the top of the second electrode (top emission).

[0078] In the method formed at the top of the second electrode (Top emission), light formed in the light-emitting layer is emitted toward the cathode, and as the light emitted toward the cathode passes through a light efficiency improvement layer (CPL) formed of a compound according to the present invention with a relatively high refractive index, the wavelength of the light is amplified and thus the light efficiency is increased.

[0079] The structure of the organic layer of a preferred organic light-emitting diode according to the present invention will be explained in more detail in the embodiments described below.

[0081] In addition, the organic light-emitting diode according to the present invention can be manufactured by using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, 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.

[0082] In addition to the above method, an organic light-emitting diode can also be fabricated 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, an emitting layer, and an electron transport layer, but is not limited thereto and may have a single-layer structure. Furthermore, the organic layer can be manufactured with fewer layers by using various polymer materials and a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

[0083] As for the anode material, a material with a large work function is generally preferred so that hole injection into the organic layer can be smooth. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metal and oxide such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited to these.

[0084] The above-mentioned cathode material is preferably a material with a small work function to facilitate electron injection into the organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof, and multilayer materials such as LiF / Al or LiO2 / Al, but are not limited to these.

[0085] A hole injection material is a material capable of effectively receiving holes from the anode at low voltage, and it is desirable that the HOMO (highest occupied molecular orbital) 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 hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited to these.

[0086] As hole transport materials, materials capable of receiving holes from the anode or hole injection layer and transferring them to the emissive layer are suitable if they have high hole mobility. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but are not limited to these.

[0087] As for the luminescent material, it is a material capable of emitting light in the visible light region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material with good quantum efficiency for fluorescence or phosphorescence is preferred. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole and benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, rubrene, etc., but are not limited to these.

[0088] As an electron transport material, a material capable of effectively receiving electrons from the cathode and transferring them to the emissive layer is suitable, provided that the material has high electron mobility. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, and hydroxyflavone-metal complexes, but are not limited to these.

[0089] The organic light-emitting device according to the present invention may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0091] The present invention will be described in more detail below with reference to preferred embodiments. However, these embodiments are intended to explain the invention more specifically, and the scope of the invention is not limited by them. It will be obvious to those skilled in the art that various changes and modifications are possible within the scope and spirit of the invention.

[0093] Synthetic example 1: Synthesis of Compound 10

[0094] (1) Preparation Example 1 : Synthesis of the intermediate 10⁻¹

[0095]

[0096] 2,2-Bis(4-hydroxyphenyl)propane (10.0 g, 0.044 mol) and Pyridine (17.3 g, 0.220 mol) were dissolved in DCM and cooled to 0 ℃. Then, Tf2O (in DCM, 16.2 g, 0.132 mol) was slowly added dropwise, raised to room temperature, and reacted by stirring for 12 hours. After the reaction was completed, the mixture was extracted and concentrated, then column-recrystallized to obtain 16.2 g (yield 75.1%) of <intermediate 10-1>.

[0098] (2) Preparation Example 2: Synthesis of Compound 10

[0099]

[0100] 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O were added to intermediate 10-1 (10.0 g, 0.020 mol), 3,5-Bis(trifluoromethyl)phenylboronic acid (12.6 g, 0.048 mol), K2CO3 (16.8 g, 0.120 mol), and Pd(PPh3)4 (0.5 g, 0.4 mmol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 9.3 g (yield 73.8%) of <Compound 10>.

[0101] LC / MS: m / z=620[(M) + ]

[0103] Synthetic example 2: Synthesis of Compound 14

[0104] (1) Preparation Example 1 : Synthesis of intermediate 14-1

[0105]

[0106] 200 mL of Dioxane was added to 1-Bromo-2-chlorobenzene (10.0 g, 0.052 mol), Bis(pinacolato)diboron (15.9 g, 0.062 mol), KOAc (15.4 g, 0.156 mol), and Pd(dppf)Cl2 (1.9 g, 2.6 mmol), and the mixture was reacted with stirring at 100 °C for 12 hours. After the reaction was complete, the mixture was extracted, concentrated, and column-coated to obtain 8.8 g (yield 70.6%) of <Intermediate 14-1>.

[0108] (2) Preparation Example 2 : Synthesis of intermediate 14-2

[0109]

[0110] 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O were added to intermediate 10-1 (10.0 g, 0.020 mol), intermediate 14-1 (11.6 g, 0.048 mol), K2CO3 (16.8 g, 0.120 mol), and Pd(PPh3)4 (0.5 g, 0.4 mmol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 6.5 g (yield 76.7%) of <intermediate 14-2>.

[0112] (3) Preparation Example 3: Synthesis of Compound 14

[0113]

[0114] Intermediate 14-2 (10.0 g, 0.024 mol), 3,5-Di-tert-butylphenylboronic acid (13.5 g, 0.058 mol), K2CO3 (16.6 g, 0.120 mol), Pd(Oac)2 (2.8 g, 2.4 mmol), X-Phos (2.3 g, 4.8 mmol), 200 mL of THF, and 50 mL of H2O were added and the mixture was reacted at 90 °C for 6 hours with stirring. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 12.9 g (yield 74.3%) of <Compound 14>.

[0115] LC / MS: m / z=724[(M) + ]

[0117] Synthetic example 3: Synthesis of Compound 29

[0118] (1) Preparation Example 1 : Synthesis of intermediate 29-1

[0119]

[0120] 1-Bromo-2-chlorobenzene (10.0 g, 0.052 mol), 2-Pyrrolidinone (5.3 g, 0.062 mol), K3PO4 (33.3 g, 0.156 mol), Pd(dba)2 (1.5 g, 2.6 mmol), Xant-Phos (5.4 g, 9.3 mmol), and Dioxane were added and the mixture was reacted under reflux stirring for 16 hours. After the reaction was complete, the mixture was extracted, concentrated, and column-coated to obtain 8.9 g (yield 87.1%) of <Intermediate 29-1>.

[0122] (2) Preparation Example 2 : Synthesis of intermediate 29-2

[0123]

[0124] 200 mL of Dioxane was added to intermediate 29-1 (10.0 g, 0.051 mol), Bis(pinacolato)diboron (35.2 g, 0.061 mol), CH3COOK (10.0 g, 0.102 mol), Pd(dppf)Cl2 (1.1 g, 1.53 mmol), and X-Phos (0.9 g, 1.83 mmol), and the mixture was reacted with stirring at 100 °C for 12 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 9.4 g (yield 64.0%) of <intermediate 29-2>.

[0126] (3) Preparation Example 3: Synthesis of Compound 29

[0127]

[0128] 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O were added to intermediate 10-1 (10.0 g, 0.020 mol), intermediate 29-2 (14.0 g, 0.048 mol), K2CO3 (16.8 g, 0.120 mol), and Pd(PPh3)4 (0.5 g, 0.4 mmol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 7.6 g (yield 72.7%) of <Compound 29>.

[0129] LC / MS: m / z=514[(M) + ]

[0131] Synthetic example 4: Synthesis of Compound 82

[0132] (1) Preparation Example 1 : Synthesis of intermediate 82-1

[0133]

[0134] 2,2-Bis(4-hydroxyphenyl)hexafluoropropane (10.0 g, 0.030 mol) and Pyridine (11.8 g, 0.150 mol) were dissolved in DCM and cooled to 0 ℃. Then, Tf2O (in DCM, 16.2 g, 0.090 mol) was slowly added dropwise, raised to room temperature, and reacted by stirring for 12 hours. After the reaction was completed, the product was extracted and concentrated, then column-recrystallized to obtain 12.6 g (yield 70.6%) of <Intermediate 82-1>.

[0136] (2) Preparation Example 2: Synthesis of Compound 82

[0137]

[0138] 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O were added to intermediate 82-1 (10.0 g, 0.017 mol), 3,5-Di-tert-butylphenylboronic acid (9.4 g, 0.041 mol), K2CO3 (13.8 g, 0.102 mol), and Pd(PPh3)4 (0.4 g, 0.34 mmol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 8.5 g (yield 75.0%) of <compound 82>.

[0139] LC / MS: m / z=680[(M) + ]

[0141] Synthetic example 5: Synthesis of Compound 84

[0142] (1) Preparation Example 1: Synthesis of Compound 84

[0143]

[0144] 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O were added to intermediate 82-1 (10.0 g, 0.017 mol), 3,5-Bis(trifluoromethyl)phenylboronic acid (10.3 g, 0.041 mol), K2CO3 (13.8 g, 0.102 mol), and Pd(PPh3)4 (0.4 g, 0.34 mmol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 8.8 g (yield 72.5%) of <compound 84>.

[0145] LC / MS: m / z=728[(M) + ]

[0147] Synthetic example 6: Synthesis of Compound 89

[0148] (1) Preparation Example 1 : Synthesis of intermediate 89-1

[0149]

[0150] 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O were added to intermediate 82-1 (10.0 g, 0.017 mol), intermediate 14-1 (9.5 g, 0.041 mol), K2CO3 (13.8 g, 0.102 mol), and Pd(PPh3)4 (0.4 g, 0.34 mmol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 6.7 g (yield 76.6%) of <intermediate 89-1>.

[0152] (2) Preparation Example 2: Synthesis of Compound 89

[0153]

[0154] Intermediate 89-1 (10.0 g, 0.019 mol), 3,5-Di-tert-butylphenylboronic acid (10.7 g, 0.046 mol), K2CO3 (13.2 g, 0.095 mol), Pd(Oac)2 (2.2 g, 1.9 mmol), X-Phos (1.8 g, 3.8 mmol), 200 mL of THF, and 50 mL of H2O were added and reacted at 90 °C for 6 hours with stirring. After the reaction was completed, the mixture was extracted and concentrated, then column-recrystallized to obtain 11.7 g (yield 73.8%) of <Compound 89>.

[0155] LC / MS: m / z=832[(M) + ]

[0157] Synthetic example 7: Synthesis of Compound 91

[0158] (1) Preparation Example 1: Synthesis of Compound 91

[0159]

[0160] Intermediate 89-1 (10.0 g, 0.019 mol), 3,5-Bis(trifluoromethyl)phenylboronic acid (11.8 g, 0.046 mol), K2CO3 (13.2 g, 0.095 mol), Pd(Oac)2 (2.2 g, 1.9 mmol), X-Phos (1.8 g, 3.8 mmol), 200 mL of THF, and 50 mL of H2O were added and reacted at 90 °C for 6 hours with stirring. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 12.0 g (yield 71.6%) of <Compound 91>.

[0161] LC / MS: m / z=880[(M) + ]

[0163] Synthetic example 8: Synthesis of Compound 104

[0164] (1) Preparation Example 1: Synthesis of Compound 104

[0165]

[0166] 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O were added to intermediate 82-1 (10.0 g, 0.017 mol), intermediate 29-2 (11.5 g, 0.041 mol), K2CO3 (13.8 g, 0.102 mol), and Pd(PPh3)4 (0.4 g, 0.34 mmol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 7.1 g (yield 68.5%) of <compound 104>.

[0167] LC / MS: m / z=622[(M) + ]

[0169] Synthetic example 9: Synthesis of Compound 106

[0170] (1) Preparation Example 1 : Synthesis of intermediate 106-1

[0171]

[0172] 1,3-Dibromo-5-chlorobenzene (10.0 g, 0.037 mol), 2-Pyrrolidinone (7.6 g, 0.089 mol), K3PO4 (47.1 g, 0.222 mol), Pd(dba)2 (2.1 g, 3.7 mmol), Xant-Phos (15.4 g, 0.027 mol), and Dioxane were added and the mixture was reacted under reflux stirring for 16 hours. After the reaction was complete, the mixture was extracted, concentrated, and then column-coated to obtain 8.4 g (yield 81.5%) of <intermediate 106-1>.

[0174] (2) Preparation Example 2 : Synthesis of intermediate 106-2

[0175]

[0176] 200 mL of Dioxane was added to intermediate 106-1 (10.0 g, 0.036 mol), Bis(pinacolato)diboron (24.7 g, 0.043 mol), CH3COOK (7.0 g, 0.072 mol), Pd(dppf)Cl2 (0.8 g, 1.08 mmol), and X-Phos (0.6 g, 1.29 mmol), and the mixture was reacted with stirring at 100 °C for 12 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 9.6 g (yield 72.3%) of <intermediate 106-2>.

[0178] (3) Preparation Example 3: Synthesis of Compound 106

[0179]

[0180] Intermediate 89-1 (10.0 g, 0.019 mol), intermediate 106-2 (16.9 g, 0.046 mol), K2CO3 (13.2 g, 0.095 mol), Pd(Oac)2 (2.2 g, 1.9 mmol), X-Phos (1.8 g, 3.8 mmol), 200 mL of THF, and 50 mL of H2O were added and reacted at 90 °C for 6 hours with stirring. After the reaction was completed, the mixture was extracted and concentrated, then column-recrystallized to obtain 11.8 g (yield 65.9%) of <Compound 106>.

[0181] LC / MS: m / z=940[(M) + ]

[0183] Synthetic example 10: Synthesis of Compound 154

[0184] (1) Preparation Example 1 : Synthesis of intermediate 154-1

[0185]

[0186] 1,1-Bis(4-hydroxyphenyl)cyclopentane (10.0 g, 0.039 mol) and Pyridine (15.6 g, 0.195 mol) were dissolved in DCM and cooled to 0 ℃. Then, Tf2O (in DCM, 16.2 g, 0.117 mol) was slowly added dropwise, raised to room temperature, and reacted by stirring for 12 hours. After the reaction was completed, the product was extracted and concentrated, then column-recrystallized to obtain 14.4 g (yield 70.6%) of <Intermediate 154-1>.

[0188] (2) Preparation Example 2: Synthesis of Compound 154

[0189]

[0190] 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O were added to intermediate 154-1 (10.0 g, 0.019 mol), 3,5-Bis(trifluoromethyl)phenylboronic acid (11.9 g, 0.046 mol), K2CO3 (16.0 g, 0.114 mol), and Pd(PPh3)4 (0.5 g, 0.38 mol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 9.1 g (yield 73.0%) of <compound 154>.

[0191] LC / MS: m / z=646[(M) + ]

[0193] Synthetic example 11: Synthesis of Compound 217

[0194] (1) Preparation Example 1 : Synthesis of intermediate 217-1

[0195]

[0196] 1,1-Bis(4-hydroxyphenyl)cyclohexane (10.0 g, 0.037 mol) and Pyridine (14.7 g, 0.185 mol) were dissolved in DCM and cooled to 0 ℃. Then, Tf2O (in DCM, 16.2 g, 0.111 mol) was slowly added dropwise, raised to room temperature, and reacted by stirring for 12 hours. After the reaction was completed, the product was extracted and concentrated, then column-recrystallized to obtain 13.7 g (yield 69.1%) of <Intermediate 217-1>.

[0198] (2) Preparation Example 2: Synthesis of Compound 217

[0199]

[0200] 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O were added to intermediate 217-1 (10.0 g, 0.019 mol), 3,5-Bis(trifluoromethyl)phenylboronic acid (11.6 g, 0.046 mol), K2CO3 (15.6 g, 0.114 mol), and Pd(PPh3)4 (0.4 g, 0.38 mmol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 8.9 g (yield 71.7%) of <compound 217>.

[0201] LC / MS: m / z=660[(M) + ]

[0203] Synthetic example 12: Synthesis of Compound 223

[0204] (1) Preparation Example 1 : Synthesis of intermediate 223-1

[0205]

[0206] 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O were added to intermediate 217-1 (10.0 g, 0.019 mol), intermediate 14-1 (10.8 g, 0.046 mol), K2CO3 (15.6 g, 0.114 mol), and Pd(PPh3)4 (0.4 g, 0.38 mmol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 6.5 g (yield 75.7%) of <intermediate 223-1>.

[0208] (2) Preparation Example 2: Synthesis of Compound 223

[0209]

[0210] Intermediate 223-1 (10.0 g, 0.022 mol), 3,5-Di-tert-butylphenylboronic acid (13.5 g, 0.053 mol), K2CO3 (15.1 g, 0.110 mol), Pd(Oac)2 (2.5 g, 2.2 mmol), X-Phos (2.1 g, 4.4 mmol), 200 mL of THF, and 50 mL of H2O were added and reacted at 90 °C for 6 hours with stirring. After the reaction was completed, the mixture was extracted and concentrated, then column-recrystallized to obtain 11.8 g (yield 66.4%) of <Compound 223>.

[0211] LC / MS: m / z=812[(M) + ]

[0213] Synthetic example 13: Synthesis of Compound 234

[0214] (1) Preparation Example 1: Synthesis of Compound 234

[0215]

[0216] 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O were added to intermediate 217-1 (10.0 g, 0.019 mol), intermediate 29-1 (12.9 g, 0.046 mol), K2CO3 (15.6 g, 0.114 mol), and Pd(PPh3)4 (0.4 g, 0.38 mmol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 7.1 g (yield 68.2%) of <compound 234>.

[0217] LC / MS: m / z=554[(M) + ]

[0219] Synthetic example 14: Synthesis of Compound 320

[0220] (1) Preparation Example 1 : Synthesis of intermediate 320-1

[0221]

[0222] 2,3-Dichloropyridine (10.0 g, 0.068 mol), 3,5-Bis(trifluoromethyl)phenylboronic acid (20.9 g, 0.082 mol), K2CO3 (28.0 g, 0.204 mol), Pd(Oac)2 (3.9 g, 3.4 mmol), X-Phos (3.2 g, 6.8 mmol), 200 mL of THF, and 50 mL of H2O were added and the mixture was reacted at 90 °C for 6 hours with stirring. After the reaction was complete, the mixture was extracted, concentrated, and column-coated to obtain 11.3 g (yield 51.4%) of <intermediate 320-1>.

[0224] (2) Preparation Example 2 : Synthesis of intermediate 320-2

[0225]

[0226] 200 mL of Dioxane was added to intermediate 320-1 (10.0 g, 0.031 mol), Bis(pinacolato)diboron (21.1 g, 0.037 mol), CH3COOK (6.0 g, 0.062 mol), Pd(dppf)Cl2 (0.7 g, 0.93 mmol), and X-Phos (0.5 g, 1.11 mmol), and the mixture was reacted with stirring at 100 °C for 12 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 9.1 g (yield 71.0%) of <intermediate 320-2>.

[0228] (3) Preparation Example 3: Synthesis of Compound 320

[0229]

[0230] 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O were added to intermediate 82-1 (10.0 g, 0.017 mol), intermediate 320-2 (16.7 g, 0.041 mol), K2CO3 (13.8 g, 0.102 mol), and Pd(PPh3)4 (0.4 g, 0.34 mmol), and the mixture was reacted with stirring at 100 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 10.8 g (yield 73.5%) of <compound 320>.

[0231] LC / MS: m / z=882[(M) + ]

[0233] device Examples (CPL)

[0234] In an embodiment according to the present invention, the anode was patterned using an Ag-containing ITO glass substrate of 25 mm × 25 mm × 0.7 mm to have a light-emitting area of ​​2 mm × 2 mm, and then cleaned. After mounting the patterned ITO substrate in a vacuum chamber, 1 × 10 -6Organic materials and metals were deposited on a substrate with the following structure at a process pressure of torr or higher.

[0236] device Examples 1 to 48

[0237] A compound implemented according to the present invention was employed in a light efficiency improvement layer provided in an organic light-emitting diode, and after fabricating an organic light-emitting diode having the device structure as described below, the light emission and driving characteristics of the organic light-emitting diode containing the compound implemented according to the present invention were measured.

[0239] Ag / ITO / Hole injection layer (HAT-CN, 5 nm) / Hole transport layer (α-NPB, 100 nm) / Electron blocking layer (TCTA, 10 nm) / Emitting layer (20 nm) / Electron transport layer (201:Liq, 30 nm) / LiF (1 nm) / Mg:Ag (15 nm) / Photometric efficiency enhancement layer (70 nm)

[0241] A hole injection layer was formed by depositing [HAT-CN] to a thickness of 5 nm on an Ag-containing ITO transparent electrode on a glass substrate, a hole transport layer was formed by depositing [α-NPB] to a thickness of 100 nm, and an electron blocking layer was formed by depositing [TCTA] to a thickness of 10 nm. Then, an emissive layer was formed by co-depositing [BH1] as the host compound and [BD1] as the dopant compound to a thickness of 20 nm. Subsequently, an electron transport layer (doped with 50% Liq of the

[0201] compound below) was deposited to a thickness of 30 nm, an electron injection layer was formed by depositing LiF to a thickness of 1 nm, and a cathode was formed by depositing Mg:Ag to a thickness of 15 nm in a ratio of 1:9.

[0242] In addition, an organic light-emitting diode was fabricated by forming a film with a thickness of 70 nm of a compound implemented according to the present invention as described in [Table 1] below as a light efficiency improvement layer (capping layer).

[0244] device Comparative example 1

[0245] The organic light-emitting device for Comparative Example 1 was manufactured in the same manner as the device structure of the above example, except that it does not have a light efficiency improvement layer.

[0247] device Comparative example 2

[0248] The organic light-emitting diode for device Comparison Example 2 was fabricated in the same manner as the device structure of the above example, except that Alq3 was used instead of the compound according to the present invention as the compound employed in the light efficiency improvement layer.

[0250] Experimental Example 1 : Element Examples Luminescence characteristics of 1 to 48

[0251] For the organic light-emitting diodes manufactured according to the above examples and comparative examples, the driving voltage, current efficiency, and color coordinates were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), and the results based on 1,000 nit are as shown in [Table 1] below.

[0252] Examples Light efficiency improvement layer V cd / A CIEx CIEy 1 Chemical formula 3 3.89 8.49 0.1372 0.0548 2 Chemical formula 6 3.90 8.60 0.1372 0.0549 3 Chemical formula 7 3.86 8.33 0.1406 0.0475 4 Chemical formula 10 3.92 8.13 0.1374 0.0533 5 Chemical formula 13 3.91 8.40 0.1371 0.0526 6 Chemical formula 14 3.92 8.45 0.1433 0.0481 7 Chemical formula 15 3.73 8.56 0.1388 0.0512 8 Chemical formula 16 3.69 8.37 0.1374 0.0576 9 Chemical formula 20 3.75 8.14 0.1377 0.0467 10 Chemical formula 22 3.83 8.61 0.1430 0.0445 11 Chemical formula 26 3.69 8.75 0.1324 0.0556 12 Chemical formula 29 3.61 8.17 0.1418 0.0476 13 Chemical formula 31 3.82 8.33 0.1407 0.0514 14 Chemical formula 39 3.67 8.33 0.1415 0.0489 15 Chemical formula 41 3.72 8.65 0.1418 0.0479 16 Chemical formula 51 3.55 8.17 0.1437 0.0486 17 Chemical formula 57 3.71 8.19 0.1445 0.0475 18 Chemical formula 59 3.68 8.95 0.1354 0.0556 19 Chemical formula 61 3.82 8.40 0.1405 0.0518 20 Chemical formula 62 3.67 8.13 0.1396 0.0545 21 Chemical formula 63 3.56 8.19 0.1412 0.0478 22 Chemical formula 70 3.63 8.25 0.1406 0.0545 23 Chemical formula 79 3.64 8.18 0.1419 0.0461 24 Chemical formula 82 3.79 8.45 0.1364 0.0546 25 Chemical formula 83 3.56 8.40 0.1407 0.0497 26 Chemical formula 84 3.57 8.26 0.1422 0.0446 27 Chemical formula 85 3.58 8.45 0.1425 0.0463 28 Chemical formula 88 3.91 8.26 0.1422 0.0460 29 Chemical formula 89 3.59 8.53 0.1354 0.0546 30 Chemical formula 90 3.67 8.23 0.1383 0.0497 31 Chemical formula 91 3.73 8.36 0.1373 0.0560 32 Chemical formula 93 3.62 8.39 0.1385 0.0456 33 Chemical formula 96 3.83 8.40 0.1392 0.0538 34 Chemical formula 101 3.67 8.31 0.1388 0.0486 35 Chemical formula 104 3.59 8.13 0.1405 0.0490 36 Chemical formula 106 3.61 8.34 0.1392 0.0505 37 Chemical formula 110 3.58 8.43 0.1386 0.0515 38 Chemical formula 128 3.49 8.10 0.1393 0.0518 39 Chemical formula 130 3.80 8.72 0.1343 0.0558 40 Chemical formula 154 3.51 8.15 0.1366 0.0550 41 Chemical formula 167 3.76 8.49 0.1364 0.0586 42 Chemical formula 173 3.62 8.17 0.1405 0.0472 43 Chemical formula 217 3.79 8.55 0.1364 0.0566 44 Chemical formula 223 3.77 8.35 0.1364 0.0523 45 Chemical formula 234 3.81 8.24 0.1415 0.0487 46 Chemical formula 275 3.67 8.52 0.1344 0.0556 47 Chemical formula 296 3.84 8.25 0.1384 0.0512 48 Chemical formula 320 3.65 8.21 0.1383 0.0527 Comparative Example 1 Not in use 4.68 7.03 0.1502 0.1412 Comparative Example 2 Alq3 4.33 7.84 0.1471 0.0583

[0253] Looking at the results shown in [Table 1] above, it can be confirmed that in the case of an organic light-emitting device in which the compound according to the present invention is employed in a light efficiency improvement layer provided in the device, the driving voltage is reduced and the current efficiency is improved compared to a device without a conventional light efficiency improvement layer or a device in which a compound conventionally used in the light efficiency improvement layer is employed (Comparative Examples 1 and 2).

[0254]

[0255] [HAT_CN] [α-NPB] [BH1] [BD1] [ET1]

[0256]

[0257] [EB1]

Claims

Claim 1 Organic compound represented by the following [Chemical Formula I]: [Chemical Formula I] In the above [Chemical Formula I], R1 and R2 are identical or different from each other and are each independently selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted deuterated alkyl group having 1 to 20 carbon atoms; R1 and R2 may be connected to each other to form a ring; Ar1 ​​and Ar2 are identical or different from each other and are each independently selected from a phenyl group, a substituted biphenyl group, a substituted naphthyl group, a substituted pyridinyl group substituted with one or more substituents, and [Structural Formula 1], or are a structure in which these are connected; and the one or more substituents are deuterium, a halogen group, an alkyl group, a halogenated alkyl group, a deuterated alkyl group, a cycloalkyl group, a heterocycloalkyl group, an alkylsilyl group, an arylsilyl group, and [Structural Formula 1] below. Selected, [Structure Formula 1] In the above [Structural Formula 1], R is independently selected within each structure from hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group having 1 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 unsubstituted halogenated alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and in each structure of the above [Structural Formula 1], a plurality of Rs are identical or different from each other. Claim 2 An organic compound according to claim 1, wherein the term "substituted or unsubstituted" in the definitions of R, R1, and R2 means that R, R1, and R2 are each substituted with one or more substituents selected from deuterium, halogen group, alkyl group, halogenated alkyl group, deuteriumated alkyl group, cycloalkyl group, heterocycloalkyl group, alkoxy group, halogenated alkoxy group, deuteriumated alkoxy group, aryl group, heteroaryl group, alkylsilyl group, and arylsilyl group, or are substituted with a substituent in which two or more of the said substituents are connected, or have no substituents. Claim 3 delete Claim 4 In claim 1, the compound is characterized in that [Chemical Formula I] is selected from the following compounds: Claim 5 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, wherein the organic light-emitting device further comprises 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, and wherein the light efficiency improvement layer comprises a compound represented by [Chemical Formula I] according to claim 1. Claim 6 An organic light-emitting device according to claim 5, wherein the light efficiency improvement layer is formed on at least one of the lower part of the first electrode or the upper part of the second electrode. Claim 7 Any one organic compound selected from the following compounds:

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