Organic compound and electroluminescent device comprising the same

Abstract

The present invention relates to a 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 A1 to A4 and B1 to B2 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 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 light-emitting compound represented by the following [Chemical Formula I], which is employed as a material for improving light efficiency in an organic light-emitting device and can achieve low voltage driving of the device 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) A1 and A2 are identical or different from each other and are each independently selected from [Structure Formula 1] below.

[0020] [Structural Formula 1]

[0021]

[0022] In the above [Structural Formula 1],

[0023] R1 to R5 are identical or different from each other and are each independently selected from deuterium, cyano group, halogen group, substituted or unsubstituted C1 to 20 alkyl group, substituted or unsubstituted C1 to 20 alkoxy group, substituted or unsubstituted C1 to 20 halogenated alkyl group, substituted or unsubstituted C1 to 20 halogenated alkoxy group, substituted or unsubstituted C3 to 20 cycloalkyl group, substituted or unsubstituted C2 to 20 heterocycloalkyl group, substituted or unsubstituted C6 to 30 aryl group, substituted or unsubstituted C2 to 30 heteroaryl group and the following [Structural Formula 2].

[0024] [Structural Formula 2]

[0025]

[0026] In the above [Structural Formula 2],

[0027] R is independently selected within each structure from hydrogen, deuterium, cyano group, 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 2], a plurality of R are identical or different from each other.

[0029] (ii) B1 and B2 are identical or different from each other and are each independently selected from hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted halogenated alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted halogenated alkoxy group having 1 to 20 carbon atoms, and substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms.

[0031] (iii) In the definitions of R, R1 to R5, B1 and B2, the term “substituted or unsubstituted” means that R, R1 to R5, B1 and B2 are each substituted with one or more substituents selected from deuterium, halogen group, cyano 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.

[0032] 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.

[0033] 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.

[0035] In the present invention, examples of the substituents are described in detail below, but are not limited thereto.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] In the present invention, the fluorenyl group comprises the 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.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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.

[0047] Specific examples of halogen groups used as substituents in the present invention include fluorine (F), chlorine (Cl), bromine (Br), etc.

[0048] 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.

[0049] 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.

[0051] 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.

[0052] 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.

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0089] 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.

[0091] 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 light-emitting compound according to the present invention is used in the organic layer of the device.

[0092] 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.

[0094] An organic electroluminescent 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).

[0095] 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.

[0096] 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.

[0098] 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.

[0099] 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, a light-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.

[0100] 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.

[0101] 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.

[0102] 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.

[0103] 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.

[0104] 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.

[0105] 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.

[0107] 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.

[0108] In addition, the organic light-emitting compound according to the present invention can also function in organic electronic devices, including organic solar cells, organic photosensitive materials, and organic transistors, using a principle similar to that applied to organic light-emitting devices.

[0110] 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.

[0112] Synthetic example 1: Synthesis of Compound 5

[0113] (1) Preparation Example 1 : Sum of Compound 5

[0114]

[0115] 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O were added to 1,2,4,5-Tetrabromobenzene (10.0 g, 0.025 mol), 3,5-Dimethylphenyl boronic acid (18.3 g, 0.122 mol), K2CO3 (42.1 g, 0.305 mol), and Pd(PPh3)4 (2.3 g, 0.002 mol), and the mixture was reacted with stirring at 80 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 9.5 g (yield 75.6%) of <Compound 5>.

[0116] LC / MS: m / z=494[(M) + ]

[0118] Synthetic example 2: Synthesis of Compound 21

[0119] (1) Preparation Example 1: Synthesis of Compound 21

[0120]

[0121] 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O were added to 1,2,4,5-Tetrabromobenzene (10.0 g, 0.025 mol), 3,5-Bis(trifluoromethyl)phenylboronic acid (31.5 g, 0.122 mol), K2CO3 (42.1 g, 0.305 mol), and Pd(PPh3)4 (2.3 g, 0.002 mol), and the mixture was reacted with stirring at 80 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 16.9 g (yield 71.8%) of <Compound 21>.

[0122] LC / MS: m / z=926[(M) + ]

[0124] Synthetic example 3: Synthesis of Compound 27

[0125] (1) Preparation Example 1 : Synthesis of intermediate 27-1

[0126]

[0127] 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O were added to 1,4-Dibromo-2,5-dichlorobenzene (10.0 g, 0.033 mol), 3,5-Dimethylphenyl boronic acid (11.8 g, 0.079 mol), K2CO3 (27.2 g, 0.197 mol), and Pd(PPh3)4 (0.8 g, 0.0007 mol), and the mixture was reacted with stirring at 80 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 7.4 g (yield 63.5%) of <Intermediate 27-1>.

[0129] (2) Preparation Example 2: Synthesis of Compound 27

[0130]

[0131] Intermediate 27-1 (10.0 g, 0.028 mol), 3,5-Bis(trifluoromethyl)phenylboronic acid (17.4 g, 0.068 mol), K2CO3 (19.5 g, 0.141 mol), Pd(OAc)2 (3.3 g, 0.003 mol), X-Phos (2.7 g, 0.006 mol), 200 mL of THF, and 50 mL of H2O were added and the mixture was reacted by stirring at 70 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 13.3 g (yield 66.5%) of <Compound 27>.

[0132] LC / MS: m / z=710[(M) + ]

[0134] Synthetic example 4: Synthesis of Compound 34

[0135] (1) Preparation Example 1 : Synthesis of intermediate 34-1

[0136]

[0137] 1-Bromo-2-chlorobenzene (10.0 g, 0.052 mol), 2-Pyrrolidinone (5.3 g, 0.063 mol), Cs2CO3 (23.8 g, 0.073 mol), Pd(dba)2 (1.5 g, 0.003 mol), Xant-Phos (5.4 g, 0.009 mol), and dioxane were added and the mixture was reacted under reflux stirring for 16 hours. After the reaction was completed, the mixture was extracted, concentrated, and then column-processed to obtain 8.9 g (yield 87.1%) of <Intermediate 34-1>.

[0139] (2) Preparation Example 2 : Synthesis of intermediate 34-2

[0140]

[0141] Dioxane was added to intermediate 34-1 (10.0 g, 0.051 mol), Bis(pinacolato)diboron (15.6 g, 0.061 mol), CH3COOK (15.1 g, 0.153 mol), Pd(dppf)Cl2 (1.9 g, 0.003 mol), and XPhos (2.2 g, 0.005 mol), 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 10.5 g (yield 71.5%) of <intermediate 34-2>.

[0143] (3) Preparation Example 3: Synthesis of Compound 34

[0144]

[0145] 1,2,4,5-Tetrabromobenzene (10.0 g, 0.025 mol), intermediate 34-2 (35.0 g, 0.122 mol), K2CO3 (42.1 g, 0.305 mol), and Pd(PPh3)4 (2.4 g, 0.002 mol) were mixed with 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O and reacted at 80 °C for 6 hours with stirring. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 12.2 g (yield 67.2%) of <Compound 34>.

[0146] LC / MS: m / z=714[(M) + ]

[0148] Synthetic example 5: Synthesis of Compound 54

[0149] (1) Preparation Example 1 : Synthesis of intermediate 54-1

[0150]

[0151] 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O were added to 1,4-Dibromo-2,5-dichlorobenzene (10.0 g, 0.033 mol), 3,5-Bis(trifluoromethyl)phenylboronic acid (20.3 g, 0.079 mol), K2CO3 (27.2 g, 0.197 mol), and Pd(PPh3)4 (0.8 g, 0.0007 mol), and the mixture was reacted with stirring at 80 °C for 6 hours. After the reaction was complete, the mixture was extracted, concentrated, and then column-coated to obtain 11.5 g (yield 61.4%) of <Intermediate 54-1>.

[0153] (2) Preparation Example 2 : Synthesis of intermediate 54-2

[0154]

[0155] 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O were added to 1-Bromo-2-chlorobenzene (10.0 g, 0.052 mol), 2-Trifluoromethylphenyl boronic acid (11.9 g, 0.063 mol), K2CO3 (21.7 g, 0.157 mol), and Pd(PPh3)4 (1.2 g, 0.001 mol), and the mixture was reacted with stirring at 80 °C for 6 hours. After the reaction was complete, the mixture was extracted, concentrated, and column-coated to obtain 9.1 g (yield 67.9%) of <intermediate 54-2>.

[0157] (3) Preparation Example 3 : Synthesis of intermediate 54-3

[0158]

[0159] Dioxane was added to intermediate 54-2 (10.0 g, 0.039 mol), Bis(pinacolato)diboron (11.9 g, 0.047 mol), CH3COOK (11.5 g, 0.117 mol), Pd(dppf)Cl2 (1.4 g, 0.002 mol), and XPhos (1.7 g, 0.004 mol), 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 9.5 g (yield 70.0%) of <intermediate 54-3>.

[0161] (4) Preparation Example 4: Synthesis of Compound 54

[0162]

[0163] Intermediate 54-1 (10.0 g, 0.018 mol), intermediate 54-3 (14.6 g, 0.042 mol), K2CO3 (12.1 g, 0.088 mol), Pd(OAc)2 (2.0 g, 0.002 mol), X-Phos (1.7 g, 0.004 mol), 200 mL of THF, and 50 mL of H2O were added and the mixture was reacted by stirring at 70 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 10.2 g (yield 61.8%) of <Compound 54>.

[0164] LC / MS: m / z=942[(M) + ]

[0166] Synthetic example 6: Synthesis of Compound 59

[0167] (1) Preparation Example 1 : Synthesis of intermediate 59-1

[0168]

[0169] 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O were added to 1,4-Dibromo-2,5-dichlorobenzene (10.0 g, 0.033 mol), (3,5-Di-tert-butylphenyl)boronic acid (18.4 g, 0.079 mol), K2CO3 (27.2 g, 0.197 mol), and Pd(PPh3)4 (0.8 g, 0.0007 mol), and the mixture was reacted with stirring at 80 °C for 6 hours. After the reaction was complete, the mixture was extracted, concentrated, and then column-coated to obtain 12.2 g (yield 71.0%) of <intermediate 59-1>.

[0171] (2) Preparation Example 2 : Synthesis of intermediate 59-2

[0172]

[0173] 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O were added to 1-Bromo-2-chlorobenzene (10.0 g, 0.052 mol), 3,5-Bis(trifluoromethyl)phenylboronic acid (16.2 g, 0.063 mol), K2CO3 (21.7 g, 0.157 mol), and Pd(PPh3)4 (1.2 g, 0.001 mol), and the mixture was reacted with stirring at 80 °C for 6 hours. After the reaction was complete, the mixture was extracted, concentrated, and then column-coated to obtain 10.8 g (yield 63.7%) of <intermediate 59-2>.

[0175] (3) Preparation Example 3 : Synthesis of intermediate 59-3

[0176]

[0177] Dioxane was added to intermediate 59-2 (10.0 g, 0.031 mol), Bis(pinacolato)diboron (9.4 g, 0.037 mol), CH3COOK (9.1 g, 0.092 mol), Pd(dppf)Cl2 (1.1 g, 0.002 mol), and XPhos (1.3 g, 0.003 mol), 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 9.2 g (yield 71.8%) of <intermediate 59-3>.

[0179] (4) Preparation Example 4: Synthesis of Compound 59

[0180]

[0181] Intermediate 59-1 (10.0 g, 0.019 mol), intermediate 59-3 (16.0 g, 0.046 mol), K2CO3 (13.2 g, 0.096 mol), Pd(OAc)2 (2.2 g, 0.002 mol), X-Phos (1.8 g, 0.004 mol), 200 mL of THF, and 50 mL of H2O were added and the mixture was reacted by stirring at 70 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 10.5 g (yield 53.3%) of <Compound 59>.

[0182] LC / MS: m / z=1031[(M) + ]

[0184] Synthetic example 7: Synthesis of Compound 140

[0185] (1) Preparation Example 1: Synthesis of Compound 140

[0186]

[0187] 1,2,4,5-Tetrachlorobenzene-d2 (10.0 g, 0.046 mol), B-[2,6-Bis(trifluoromethyl)phenyl]boronic acid (56.8 g, 0.220 mol), K2CO3 (76.1 g, 0.551 mol), Pd(OAc)2 (5.3 g, 0.005 mol), X-Phos (6.6 g, 0.014 mol), 200 mL of THF, and 50 mL of H2O were added and the mixture was reacted by stirring at 70 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 18.2 g (yield 42.7%) of <Compound 140>.

[0188] LC / MS: m / z=928[(M) + ]

[0190] Synthetic example 8: Synthesis of Compound 148

[0191] (1) Preparation Example 1 : Synthesis of intermediate 148-1

[0192]

[0193] 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O were added to 1,4-dibromo-2,5-dichloro-3,6-dideuteriobenzene (10.0 g, 0.033 mol), 4-tert-butylphenylboronic acid (13.9 g, 0.078 mol), K2CO3 (27.0 g, 0.196 mol), and Pd(PPh3)4 (0.8 g, 0.0007 mol), and the mixture was reacted with stirring at 80 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 8.2 g (yield 60.9%) of <Intermediate 148-1>.

[0195] (2) Preparation Example 2: Synthesis of Compound 148

[0196]

[0197] Intermediate 148-1 (10.0 g, 0.024 mol), 3,5-Bis(trifluoromethyl)phenylboronic acid (15.0 g, 0.058 mol), K2CO3 (16.7 g, 0.121 mol), Pd(OAc)2 (2.8 g, 0.002 mol), X-Phos (2.3 g, 0.005 mol), 200 mL of THF, and 50 mL of H2O were added and the mixture was reacted by stirring at 70 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 9.7 g (yield 52.2%) of <Compound 148>.

[0198] LC / MS: m / z=768[(M) + ]

[0200] Synthetic example 9: Synthesis of Compound 242

[0201] (1) Preparation Example 1 : Synthesis of intermediate 242-1

[0202]

[0203] 1,4-dibromo-2,5-dichloro-3,6-dimethylbenzene (10.0 g, 0.030 mol), (3,5-Di-tert-butylphenyl)boronic acid (16.9 g, 0.072 mol), K2CO3 (24.9 g, 0.180 mol), and Pd(PPh3)4 (0.7 g, 0.0006 mol) were mixed with 200 mL of toluene, 50 mL of ethanol, and 50 mL of H2O and reacted at 80 °C for 6 hours with stirring. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 7.9 g (yield 47.7%) of <Intermediate 242-1>.

[0205] (2) Preparation Example 2: Synthesis of Compound 242

[0206]

[0207] Intermediate 242-1 (10.0 g, 0.018 mol), intermediate 54-3 (15.2 g, 0.044 mol), K2CO3 (12.5 g, 0.091 mol), Pd(OAc)2 (2.1 g, 0.002 mol), X-Phos (1.7 g, 0.004 mol), 200 mL of THF, and 50 mL of H2O were added and the mixture was reacted by stirring at 70 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 7.1 g (yield 42.4%) of <Compound 242>.

[0208] LC / MS: m / z=923[(M) + ]

[0210] Synthetic example 10: Synthesis of Compound 328

[0211] (1) Preparation Example 1: Synthesis of Compound 328

[0212]

[0213] 1,2,4,5-tetrachloro-3,6-bis-trifluoromethyl-benzene (10.0 g, 0.028 mol), 3,5-Bis(trifluoromethyl)phenylboronic acid (35.2 g, 0.136 mol), K2CO3 (47.1 g, 0.341 mol), Pd(OAc)2 (3.3 g, 0.003 mol), X-Phos (4.1 g, 0.009 mol), 200 mL of THF, and 50 mL of H2O were added and the mixture was reacted by stirring at 70 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 17.2 g (yield 57.0%) of <Compound 328>.

[0214] LC / MS: m / z=1062[(M) + ]

[0216] Synthetic example 11: Synthesis of Compound 345

[0217] (1) Preparation Example 1: Synthesis of Compound 345

[0218]

[0219] 1,2,4,5-tetrachloro-3,6-bis-trifluoromethyl-benzene (10.0 g, 0.028 mol), intermediate 59-3 (56.8 g, 0.136 mol), K2CO3 (47.1 g, 0.341 mol), Pd(OAc)2 (3.3 g, 0.003 mol), X-Phos (4.1 g, 0.009 mol), 200 mL of THF, and 50 mL of H2O were added and the mixture was reacted with stirring at 70 °C for 6 hours. After the reaction was complete, the mixture was extracted and concentrated, then column-recrystallized to obtain 12.5 g (yield 67.3%) of <Compound 345>.

[0220] LC / MS: m / z=1366[(M) + ]

[0222] device Examples (CPL)

[0223] 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 -6 Organic materials and metals were deposited on a substrate with the following structure at a process pressure of torr or higher.

[0225] device Examples 1 to 91

[0226] 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 according to the compound implemented according to the present invention were measured.

[0228] 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)

[0230] 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, followed by forming a hole transport layer by depositing [α-NPB] to a thickness of 100 nm, and forming an electron blocking layer by depositing [TCTA] to a thickness of 10 nm. 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, and after depositing an electron transport layer (doped with 50% Liq of the [O2O1] compound below) 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. Furthermore, an organic light-emitting diode was fabricated by depositing a capping layer to a thickness of 70 nm using the compounds according to the present invention described in [Table 1] below.

[0232] device Comparative example 1

[0233] The organic light-emitting device for Comparative Example 1 was fabricated in the same way as the device structure of the above example, except that it does not have a light efficiency improvement layer.

[0235] device Comparative example 2

[0236] 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 light efficiency improvement layer compound.

[0238] device Comparative example 3

[0239] The organic light-emitting diode for device Comparison Example 3 was fabricated in the same manner as the device structure of the above example, except that [CP 1] was used instead of the compound according to the present invention as the light efficiency improvement layer compound.

[0241] device Comparative example 4

[0242] The organic light-emitting device for Comparative Example 4 was fabricated in the same manner as the device structure of the above example, except that [CP 2] was used instead of the compound according to the present invention as the light efficiency improvement layer compound.

[0244] device Comparative example 5

[0245] The organic light-emitting device for Comparative Example 5 was fabricated in the same manner as the device structure of the above example, except that [CP 3] was used instead of the compound of the present invention as the light efficiency improvement layer compound.

[0247] Experimental Example 1 : Element Examples Luminescence characteristics of 1 to 91

[0248] 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.

[0249] Examples Light efficiency improvement layer V cd / A CIEx CIEy 1 Chemical formula 2 3.43 9.25 0.1291 0.0579 2 Chemical formula 5 3.39 8.57 0.1338 0.0535 3 Chemical formula 8 3.41 8.67 0.1385 0.0493 4 Chemical formula 10 3.42 8.39 0.1381 0.0497 5 Chemical formula 11 3.43 8.29 0.1382 0.0473 6 Chemical formula 12 3.39 8.83 0.1374 0.0537 7 Chemical formula 13 3.42 8.53 0.1382 0.0522 8 Chemical formula 15 3.35 8.48 0.1409 0.0466 9 Chemical formula 18 3.46 9.15 0.1385 0.0492 10 Chemical formula 21 3.39 8.67 0.1404 0.0459 11 Chemical formula 22 3.40 8.69 0.1412 0.0460 12 Chemical formula 23 3.42 9.47 0.1321 0.0579 13 Chemical formula 25 3.48 8.51 0.1351 0.0501 14 Chemical formula 26 3.28 8.90 0.1372 0.0553 15 Chemical formula 27 3.29 8.67 0.1363 0.0568 16 Chemical formula 28 3.30 8.69 0.1379 0.0491 17 Chemical formula 29 3.41 8.46 0.1345 0.0507 18 Chemical formula 32 3.37 8.77 0.1373 0.0568 19 Chemical formula 34 3.38 8.68 0.1386 0.0487 20 Chemical formula 36 3.53 8.95 0.1331 0.0569 21 Chemical formula 40 3.30 8.90 0.1374 0.0520 22 Chemical formula 45 3.31 8.76 0.1389 0.0469 23 Chemical formula 51 3.32 8.95 0.1392 0.0480 24 Chemical formula 54 3.35 8.76 0.1389 0.0490 25 Chemical formula 55 3.43 9.03 0.1321 0.0569 26 Chemical formula 56 3.41 8.73 0.1410 0.0460 27 Chemical formula 57 3.35 8.86 0.1340 0.0583 28 Chemical formula 59 3.36 8.81 0.1405 0.0479 29 Chemical formula 60 3.37 8.90 0.1369 0.0561 30 Chemical formula 62 3.41 8.81 0.1375 0.0509 31 Chemical formula 65 3.43 8.63 0.1372 0.0513 32 Chemical formula 66 3.31 8.84 0.1369 0.0568 33 Chemical formula 67 3.32 8.93 0.1373 0.0538 34 Chemical formula 86 3.55 8.41 0.1369 0.0516 35 Chemical formula 100 3.42 8.71 0.1380 0.0500 36 Chemical formula 102 3.23 8.60 0.1360 0.0541 37 Chemical formula 108 3.54 9.22 0.1310 0.0581 38 Chemical formula 119 3.25 8.65 0.1353 0.0573 39 Chemical formula 123 3.50 8.97 0.1331 0.0609 40 Chemical formula 140 3.51 8.67 0.1372 0.0495 41 Chemical formula 141 3.53 9.05 0.1331 0.0589 42 Chemical formula 147 3.54 8.25 0.1370 0.0473 43 Chemical formula 148 3.53 8.93 0.1331 0.0579 44 Chemical formula 159 3.41 8.49 0.1353 0.0498 45 Chemical formula 171 3.51 8.85 0.1331 0.0589 46 Chemical formula 186 3.55 8.74 0.1382 0.0510 47 Chemical formula 191 3.41 9.02 0.1311 0.0579 48 Chemical formula 196 3.63 8.75 0.1351 0.0539 49 Chemical formula 201 3.52 8.53 0.1389 0.0480 50 Chemical formula 202 3.23 8.61 0.1373 0.0569 51 Chemical formula 205 3.53 8.91 0.1331 0.0589 52 Chemical formula 217 3.63 8.75 0.1351 0.0529 53 Chemical formula 221 3.55 8.78 0.1381 0.0496 54 Chemical formula 223 3.56 8.93 0.1365 0.0567 55 Chemical formula 234 3.67 8.21 0.1392 0.0436 56 Chemical formula 240 3.67 8.64 0.1381 0.0488 57 Chemical formula 242 3.69 8.75 0.1351 0.0549 58 Chemical formula 246 3.52 8.57 0.1348 0.0478 59 Chemical formula 252 3.43 9.35 0.1311 0.0549 60 Chemical formula 268 3.44 8.34 0.1385 0.0454 61 Chemical formula 272 3.45 8.58 0.1397 0.0472 62 Chemical formula 285 3.62 8.98 0.1331 0.0589 63 Chemical formula 287 3.63 8.33 0.1382 0.0486 64 Chemical formula 300 3.53 8.83 0.1331 0.0589 65 Chemical formula 306 3.62 8.83 0.1355 0.0579 66 Chemical formula 308 3.56 8.83 0.1376 0.0516 67 Chemical formula 310 3.56 8.91 0.1376 0.0506 68 Chemical formula 312 3.63 8.34 0.1384 0.0460 69 Chemical formula 313 3.53 8.85 0.1321 0.0589 70 Chemical formula 328 3.67 8.33 0.1370 0.0445 71 Chemical formula 333 3.63 8.75 0.1351 0.0517 72 Chemical formula 335 3.64 8.74 0.1364 0.0523 73 Chemical formula 337 3.55 9.04 0.1363 0.0575 74 Chemical formula 338 3.56 8.27 0.1359 0.0515 75 Chemical formula 345 3.64 9.02 0.1340 0.0561 76 Chemical formula 349 3.53 8.85 0.1331 0.0589 77 Chemical formula 353 3.63 8.65 0.1351 0.0519 78 Chemical formula 354 3.52 8.88 0.1331 0.0589 79 Chemical formula 359 3.64 8.92 0.1350 0.0581 80 Chemical formula 360 3.52 8.95 0.1321 0.0569 81 Chemical formula 365 3.53 8.94 0.1353 0.0561 82 Chemical formula 367 3.53 8.75 0.1341 0.0509 83 Chemical formula 369 3.63 8.65 0.1361 0.0529 84 Chemical formula 371 3.58 8.64 0.1395 0.0496 85 Chemical formula 372 3.59 8.41 0.1374 0.0440 86 Chemical formula 375 3.66 8.23 0.1378 0.0470 87 Chemical formula 377 3.61 8.11 0.1371 0.0518 88 Chemical formula 378 3.60 8.78 0.1358 0.0573 89 Chemical formula 381 3.63 8.65 0.1351 0.0529 90 Chemical formula 385 3.61 8.15 0.1366 0.0523 91 Chemical formula 386 3.61 8.75 0.1353 0.0519 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 Comparative Example 3 CP 1 4.26 8.06 0.1420 0.0635 Comparative Example 4 CP 2 4.05 7.62 0.1391 0.0642 Comparative Example 5 CP 3 4.19 7.78 0.1401 0.0613

[0251] Looking at the results shown in [Table 1] above, it can be confirmed that an organic light-emitting device having a compound according to the present invention in a light efficiency improvement layer provided in the organic light-emitting device has a lower driving voltage and improved current efficiency compared to a device without a conventional light efficiency improvement layer (Comparative Example 1), a device using a compound used as a conventional light efficiency improvement layer material (Comparative Example 2), and a device using a compound that is contrasted with the characteristic structure of the compound according to the present invention (Comparative Examples 3 to 5).

[0252]

[0253] [HAT_CN] [α-NPB] [BH1] [BD1] [ET1]

[0254]

[0255] [EB1] [CP1] [CP2] [CP3]

Claims

Claim 1 Compounds represented by the following [Chemical Formula I]: [Chemical Formula I] In the above [Chemical Formula I], (i) A1 to A4 are identical or different from each other and each is independently selected from any one of the following [Structural Formula 1], and [Structural Formula 1] In the above [Structural Formula 1], R1 to R5 are identical or different from each other and are each independently a deuterium, a cyano group, 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 heterocycloalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and any one selected from the following [Structural Formula 2]. In the above [Structural Formula 2], R is independently selected within each structure from hydrogen, deuterium, cyano group, 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 the above [Structural Formula 2], a plurality of R are identical or different from each other, and (ii) B1 and B2 are identical or different from each other and are independently deuterium, cyano group, substituted or unsubstituted C1 to C20 alkyl group, substituted or Any one selected from an 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, and a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, and in the definitions of R, R1 to R5, B1 and B2, "substituted or unsubstituted" means that R, R1 to R5, B1 and B2 are each substituted with one or more substituents selected from deuterium, alkyl group, halogenated alkyl group, deuteriumated alkyl group, cycloalkyl group, heterocycloalkyl group, alkoxy group, halogenated alkoxy group, deuteriumated alkoxy group, aryl 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 2 delete Claim 3 In claim 1, the compound is characterized in that [Chemical Formula I] is selected from the following compounds: Claim 4 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 5 An organic light-emitting device according to claim 4, 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.

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