KR20220148353A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to a novel organic compound represented by chemical formula I, and an organic light emitting device including the same, wherein the novel organic compound can be used as an organic layer material such as a hole transport layer, an electron transport layer, and a luminous efficiency improvement layer in an organic light emitting device to realize luminous properties such as remarkably excellent luminous efficiency and quantum efficiency.

Description

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

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

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

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

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

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

In addition, in recent years, research on improving the characteristics of an organic light emitting device by giving a change in the performance of each organic layer material, as well as a technology for improving color purity and increasing luminous efficiency by an optical thickness optimized between an anode and a cathode has been developed. It has been focused on one of the important factors for improving the performance, and as an example of this method, in order to increase the light efficiency through improvement of internal light extraction efficiency, etc. A light efficiency improvement layer (capping layer) having a refractive index is used to increase light efficiency and achieve excellent color purity.

Accordingly, the present invention is to provide a novel organic compound capable of implementing a device having significantly improved light emitting characteristics such as driving voltage, luminous efficiency and quantum efficiency by being employed in various organic layers provided in an organic light emitting device and an organic light emitting device including the same. do.

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

[Formula Ⅰ]

The characteristic structures of the [Formula I] and the definitions of A, B, Y, and R and specific compounds implemented accordingly will be described later.

The organic light emitting compound according to the present invention is used as a material for various organic layers provided in an organic light emitting device, in particular, an organic layer material such as a hole transport layer, an electron transport layer, and a light efficiency improvement layer. Because it can be improved, it can be usefully used for various display devices.

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

The present invention relates to an organic light emitting compound represented by the following [Formula I], which can achieve excellent light emitting characteristics in driving voltage characteristics, luminous efficiency, quantum efficiency, and the like of an organic light emitting device.

[Formula Ⅰ]

In the above [Formula I],

Any one of A and B is characterized in that it is represented by the following [Structural Formula 1], and the other one is a cyano group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon number 3 to 20 of a cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted carbon number It is selected from a 6 to 30 arylamine group, a substituted or unsubstituted heteroarylamine group having 3 to 30 carbon atoms, and a substituted or unsubstituted arylheteroarylamine group having 6 to 30 carbon atoms.

[Structural Formula 1]

In the [Structural Formula 1],

X is O or S.

R ₁ to R ₅ are the same as or different from each other, and each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, It is selected from a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C3 to C30 heteroaryl group, wherein R ₁ to R ₅ Either one is bonded at the A or B position of the [Formula I].

Y is selected from O, S, NR ₆ and CR ₇ R ₈ , wherein R ₆ to R ₈ are the same as or different from each other, and each independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted carbon number 1 to 20 alkyl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, and a substituted or unsubstituted C 3 to C 30 heteroaryl group.

R is a cyano group, a halogen group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, a substituted or unsubstituted C 1 to C 20 alkoxy group, a substituted or unsubstituted It is selected from an aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

Meanwhile, in the definitions of A, B, R ₁ to R ₈ and R, 'substituted or unsubstituted' means that A, B, R ₁ to R ₈ and R are deuterium, a halogen group, a cyano group, and nitro, respectively. group, hydroxyl group, amine group, alkyl group, halogenated alkyl group, deuterated alkyl group, cycloalkyl group, heterocycloalkyl group, alkoxy group, halogenated alkoxy group, deuterated alkoxy group, aryl group, heteroaryl group, alkylsilyl group and It means that it is substituted with one or two or more substituents selected from the group consisting of an arylsilyl group, is substituted with a substituent to which two or more of the substituents are connected, or does not have any substituents.

For specific examples, the substituted aryl group means that a phenyl group, a biphenyl group, a naphthalene group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a perylene group, a tetracenyl group, an anthracenyl group, etc. are substituted with other substituents do.

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

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

In the present invention, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, and the like, but is not limited thereto.

In the present invention, the alkoxy group may be straight-chain or branched. Although the number of carbon atoms of the alkoxy group is not particularly limited, it is preferably 1 to 20, which is a range that does not cause steric hindrance. Specifically, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, i-propyloxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group , neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group , a benzyloxy group, a p-methylbenzyloxy group, etc., but is not limited thereto.

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

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

,

,

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

,

,

etc.

,

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

,

etc.

,

,

,

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

,

,

,

etc.

In the present invention, the heteroaryl group is a heterocyclic group containing O, N, or S as a heteroatom, and the number of carbon atoms is not particularly limited, but preferably has 3 to 30 carbon atoms, and is a polycyclic group in which cycloalkyl or heterocycloalkyl is fused. a heteroaryl group structure, and specific examples thereof in the present invention include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group , pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyridopyrazinyl group group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, There are dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, phenoxazine group, phenothiazine group, etc., but only these It is not limited.

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

Exemplarily, the arylamine group includes a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 3-methyl-phenylamine group, a 4-methyl-naphthylamine group, and a 2-methyl-biphenyl group. an amine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, and a triphenylamine group, but is not limited thereto.

In the present invention, the silyl group is an unsubstituted silyl group or an alkylsilyl group or an arylsilyl group substituted with an alkyl group, an aryl group, etc., and specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trime oxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, and the like, but is not limited thereto.

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

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

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

The organic light emitting compound according to the present invention represented by the above [Formula I] can be used in various organic layers provided in the organic light emitting device due to its structural specificity, and more specifically, it can be used in a hole transport layer, an electron transport layer, a light efficiency improvement layer, etc. have.

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

As such, the organic compound according to the present invention can synthesize an organic light emitting compound having various characteristics using a characteristic skeleton exhibiting intrinsic characteristics and a moiety having intrinsic characteristics introduced thereto, and the Result When the organic light emitting compound according to the present invention is applied as a material for various organic layers such as a hole transport layer and an electron transport layer, and when applied to a light efficiency improvement layer provided in an organic light emitting device, characteristics of device driving voltage, luminous efficiency, etc. can be further improved.

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

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

The organic layer of the organic light emitting diode according to the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, a light efficiency improving layer (Capping layer) and the like. However, the present invention is not limited thereto and may include a smaller number or a larger number of organic layers.

In addition, the organic electroluminescent device according to an embodiment of the present invention includes a substrate, a first electrode (anode), an organic layer, a second electrode (cathode) and a light efficiency improving layer, wherein the light efficiency improving layer is a lower portion of the first electrode ( Bottom emission) or it may be formed on top of the second electrode (Top emission).

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

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

In addition, the organic light emitting diode according to the present invention is a metal or conductive metal oxide or an alloy thereof on a substrate by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation. It can be prepared by depositing an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.

In addition to this method, an organic light emitting diode may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate. The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic layer can be formed in a smaller number by a solvent process rather than a deposition method using various polymer materials, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.

As the anode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc. Metal oxides, combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT) , a conductive polymer such as polypyrrole and polyaniline, but is not limited thereto.

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

The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene, quinacridone-based organic material, perylene-based organic material, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

As the hole transport material, a material capable of transporting holes from the anode or hole injection layer to the light emitting layer is suitable, and a material with high hole mobility is suitable. There are block copolymers having a non-conjugated portion, and the like, but the low voltage driving characteristics, luminous efficiency, and lifespan characteristics of the device can be further improved by using the organic light emitting compound according to the present invention.

The light emitting material is a material capable of emitting light in the visible ray region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole and There are benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, rubrene, and the like, but is not limited thereto.

As the electron transport material, a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is suitable. Specific examples include, but are not limited to, an Al complex of 8-hydroxyquinoline, a complex containing Alq ₃ , an organic radical compound, a hydroxyflavone-metal complex, and the like, and a device using the organic light emitting compound according to the present invention of low voltage driving characteristics, luminous efficiency and lifespan characteristics can be further improved.

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

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

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

Synthesis example 1: Synthesis of compound 45

(One) production example 1: Synthesis of intermediate 45-1

3-Bromo-5-chlorobiphenyl (10.0 g, 0.037 mol), Benzoxazole (6.7 g, 0.056 mol), K ₂ CO ₃ (10.3 g, 0.075 mol), PPh ₃ (4.9 g, 0.019 mol), Cu(OAc) Toluene was added to ₂ (0.1 g, 0.0007 mol), Pd(OAc) ₂ (0.08 g, 0.0004 mol), and the reaction was stirred under reflux at 110° C. for 4 hours. After completion of the reaction, 8.5 g (yield 74.4%) of <Intermediate 45-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) production example 2: Synthesis of compound 45

6-Phenyldibenzofuran-4-boronic acid (10.0 g, 0.035 mol), intermediate 45-1 (12.7 g, 0.042 mol), K ₂ CO ₃ (14.4 g, 0.104 mol), catalyst Pd(OAc) ₂ (2.01 g, 0.002 mol), the ligand X-Phos (1.7 g, 0.004 mol), 200 mL of THF and 50 mL of H ₂ O were added, and the reaction was stirred at 90° C. for 6 hours. After completion of the reaction, 13.3 g (yield 74.6%) of <Compound 45> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=513 [(M+1) ⁺ ]

Synthesis example 2: Synthesis of compound 78

(One) production example 1: Synthesis of intermediate 78-1

4,6-Dibromodibenzofuran (10.0 g, 0.031 mol), (1,1'-Biphenyl)-4-boronic acid (7.3 g, 0.037 mol), K ₂ CO ₃ (12.8 g, 0.093 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) was added to 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H ₂ O, followed by stirring at 100 °C for 6 hours. After completion of the reaction, 5.8 g (yield 55.7%) of <Intermediate 78-1> was obtained by extraction and concentration by column.

(2) production example 2: Synthesis of intermediate 78-2

Intermediate 78-1 (10.0 g, 0.025 mol), Bis(pinacolato)diboron (7.6 g, 0.030 mol), KOAc (7.4 g, 0.075 mol), dioxane 200 in Pd(dppf)Cl ₂ (0.9 g, 0.001 mol) mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 8.1 g (yield 72.5%) of <Intermediate 78-2>.

(3) production example 3: Synthesis of compound 78

Intermediate 78-2 (10.0 g, 0.022 mol), Intermediate 45-1 (8.2 g, 0.027 mol), K ₂ CO ₃ (9.3 g, 0.067 mol), Catalyst Pd(OAc) ₂ (1.3 g, 0.001 mol), Ligand X-Phos (1.0 g, 0.002 mol), 200 mL of THF and 50 mL of H ₂ O were added, and the reaction was stirred at 90 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 8.9 g (yield 67.4%) of <Compound 78>.

LC/MS: m/z=589 [(M+1) ⁺ ]

Synthesis example 3: Synthesis of compound 122

(One) production example 1: Synthesis of intermediate 122-1

4,6-Dibromodibenzofuran (10.0 g, 0.031 mol), Benzoxazole (5.5 g, 0.046 mol), K ₂ CO ₃ (8.5 g, 0.061 mol), PPh ₃ (4.0 g, 0.15 mol), Cu(OAc) ₂ ( Toluene was added to 0.1 g, 0.0006 mol) and Pd(OAc) ₂ (0.07 g, 0.0003 mol), and the reaction was stirred under reflux at 110° C. for 4 hours. After completion of the reaction, 5.3 g (yield 47.4%) of <Intermediate 122-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of intermediate 122-2

Intermediate 122-1 (10.0 g, 0.028 mol), Bis(pinacolato)diboron (8.4 g, 0.033 mol), KOAc (8.1 g, 0.082 mol), Pd(dppf)Cl ₂ (1.0 g, 0.001 mol) dioxane 200 mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, 8.0 g (yield 70.8%) of <Intermediate 122-2> was obtained by extraction, concentration, and column.

(3) production example 3: Synthesis of intermediate 122-3

3,5-Dichlorobromobenzene (10.0 g, 0.044 mol), Benzoxazole (7.9 g, 0.066 mol), K ₂ CO ₃ (12.2 g, 0.089 mol), PPh ₃ (5.8 g, 0.22 mol), Cu(OAc) ₂ ( 0.2 g, 0.0009 mol), Pd(OAc) ₂ (0.1 g, 0.0004 mol) was added to Toluene, and the reaction was stirred under reflux at 110° C. for 4 hours. After completion of the reaction, 8.1 g (yield 69.3%) of <Intermediate 122-3> was obtained by extraction and concentration by column.

(4) production example 4: Synthesis of intermediate 122-4

Intermediate 122-3 (10.0 g, 0.038 mol), (1,1'-Biphenyl)-4-boronic acid (9.0 g, 0.045 mol), K ₂ CO ₃ (15.7 g, 0.114 mol), catalyst Pd(OAc) ₂ (2.2 g, 0.002 mol), ligand X-Phos (1.8 g, 0.004 mol), THF 200 mL and H ₂ O 50 mL were added, and the reaction was stirred at 90 ° C. for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 7.8 g (yield 54.0%) of <Intermediate 122-4>.

(5) production example 5: Synthesis of compound 122

Intermediate 122-2 (10.0 g, 0.024 mol), Intermediate 122-4 (11.2 g, 0.025 mol), K ₂ CO ₃ (17.3 g, 0.125 mol), Catalyst Pd(OAc) ₂ (2.41 g, 0.002 mol), Ligand X-Phos (1.2 g, 0.002 mol), 200 mL of THF and 50 mL of H ₂ O were added, and the reaction was stirred at 90 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 10.3 g (yield 67.2%) of <Compound 122>.

LC/MS: m/z=630[(M+1) ⁺ ]

Synthesis example 4: Synthesis of compound 124

(One) production example 1: Synthesis of Intermediate 124-1

Intermediate 122-3 (10.0 g, 0.038 mol), 3-Dibenzofuranboronic acid (9.6 g, 0.045 mol), K ₂ CO ₃ (15.7 g, 0.114 mol), catalyst Pd(OAc) ₂ (2.2 g, 0.002 mol), Ligand X-Phos (1.8 g, 0.004 mol), 200 mL of THF and 50 mL of H ₂ O were added, and the reaction was stirred at 90 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 7.2 g (yield 48.0%) of <Intermediate 124-1>.

(2) production example 2: Synthesis of compound 124

Intermediate 122-2 (10.0 g, 0.024 mol), Intermediate 124-1 (11.6 g, 0.029 mol), K ₂ CO ₃ (10.1 g, 0.073 mol), Catalyst Pd(OAc) ₂ (1.4 g, 0.001 mol), Ligand X-Phos (1.2 g, 0.002 mol), 200 mL of THF and 50 mL of H ₂ O were added, and the reaction was stirred at 90 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 11.2 g (yield 71.5%) of <Compound 124>.

LC/MS: m/z=644 [(M+1) ⁺ ]

Synthesis example 5: Synthesis of compound 150

(One) production example 1: Synthesis of intermediate 150-1

4,6-Dibromodibenzothiophene (10.0 g, 0.029 mol), 4-Cyanobenzeneboronic acid (5.2 g, 0.035 mol), K ₂ CO ₃ (12.1 g, 0.088 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) Toluene 140 mL, EtOH 35 mL, H ₂ O 35 mL, and stirred for 6 hours at 100 ℃ reacted. After completion of the reaction, 4.8 g (yield 45.0%) of <Intermediate 150-1> was obtained by extraction and concentration by column.

(2) production example 2: Synthesis of intermediate 150-2

Intermediate 150-1 (10.0 g, 0.028 mol), Bis(pinacolato)diboron (8.4 g, 0.033 mol), KOAc (8.1 g, 0.082 mol), dioxane 200 in Pd(dppf)Cl ₂ (1.0 g, 0.001 mol) mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 8.2 g (yield 72.6%) of <Intermediate 150-2>.

(3) production example 3: Synthesis of compound 150

Intermediate 150-2 (10.0 g, 0.024 mol), Intermediate 122-4 (11.1 g, 0.029 mol), K ₂ CO ₃ (10.1 g, 0.073 mol), Catalyst Pd(OAc) ₂ (1.4 g, 0.001 mol), Ligand X-Phos (1.2 g, 0.002 mol), 200 mL of THF and 50 mL of H ₂ O were added, and the reaction was stirred at 90° C. for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 11.8 g (yield 77.0%) of <Compound 150>.

LC/MS: m/z=630[(M+1) ⁺ ]

Synthesis example 6: Synthesis of compound 237

(One) production example 1: Synthesis of intermediate 237-1

3-Bromo-5-chlorobiphenyl (10.0 g, 0.037 mol), Benzothiazole (7.6 g, 0.056 mol), K ₂ CO ₃ (10.3 g, 0.075 mol), PPh ₃ (4.9 g, 0.019 mol), Cu(OAc) Toluene was added to ₂ (0.1 g, 0.0007 mol), Pd(OAc) ₂ (0.1 g, 0.0004 mol), and the reaction was stirred under reflux at 110° C. for 4 hours. After completion of the reaction, 8.4 g (yield 69.8%) of <Intermediate 237-1> was obtained by extraction and concentration by column.

(2) production example 2: Synthesis of intermediate 237-2

4,6-Dibromodibenzofuran (10.0 g, 0.031 mol), 1-Naphthaleneboronic Acid (6.3 g, 0.037 mol), K ₂ CO ₃ (12.7 g, 0.092 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) Toluene 140 mL, EtOH 35 mL, H ₂ O 35 mL, and stirred for 6 hours at 100 ℃ reacted. After completion of the reaction, 5.6 g (yield 48.9%) of <Intermediate 237-2> was obtained by extraction, concentration, and column.

(3) production example 3: Synthesis of intermediate 237-3

Intermediate 237-2 (10.0 g, 0.024 mol), Bis(pinacolato)diboron (7.2 g, 0.028 mol), KOAc (4.6 g, 0.047 mol), dioxane 200 in Pd(dppf)Cl ₂ (0.5 g, 0.001 mol) mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, 7.9 g (yield 71.1%) of <Intermediate 237-3> was obtained by extraction and concentration, followed by column and recrystallization.

(4) Preparation 4 : Synthesis of compound 237

Intermediate 237-3 (10.0 g, 0.024 mol), Intermediate 237-1 (9.2 g, 0.029 mol), K ₂ CO ₃ (9.9 g, 0.071 mol), Catalyst Pd(OAc) ₂ (1.4 g, 0.001 mol), Ligand X-Phos (1.1 g, 0.002 mol), 200 ml of THF and 50 ml of H 2 O were added, and the reaction was stirred at 90° C. for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 9.7 g (yield 70.3%) of <Compound 237>.

LC/MS: m/z=579 [(M+1) ⁺ ]

Synthesis example 7: Synthesis of compound 247

(One) production example 1: Synthesis of intermediate 247-1

3,5-Dichlorobromobenzene (10.0 g, 0.044 mol), Benzoxazole (9.0 g, 0.066 mol), K ₂ CO ₃ (12.2 g, 0.089 mol), PPh ₃ (5.8 g, 0.22 mol), Cu(OAc) ₂ ( 0.2 g, 0.0009 mol), Pd(OAc) ₂ (0.1 g, 0.0004 mol) was added to Toluene, and the reaction was stirred under reflux at 110° C. for 4 hours. After completion of the reaction, 8.5 g (yield 68.5%) of <Intermediate 247-1> was obtained by extraction and concentration by column.

(2) production example 2: Synthesis of intermediate 247-2

Intermediate 247-1 (10.0 g, 0.036 mol), (4-Naphthalen-2-ylphenyl)boronic acid (10.6 g, 0.043 mol), K ₂ CO ₃ (14.8 g, 0.107 mol), catalyst Pd(OAc) ₂ ( 2.1 g, 0.002 mol), ligand X-Phos (1.7 g, 0.004 mol), 200 ml of THF and 50 ml of H 2 O were added, and the reaction was stirred at 90° C. for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 7.5 g (yield 46.9%) of <Intermediate 247-2>.

(3) production example 3: Synthesis of compound 247

Intermediate 78-2 (10.0 g, 0.022 mol), Intermediate 247-2 (12.0 g, 0.027 mol), K ₂ CO ₃ (9.3 g, 0.067 mol), Catalyst Pd(OAc) ₂ (1.3 g, 0.001 mol), Ligand X-Phos (1.1 g, 0.002 mol), 200 mL of THF and 50 mL of H ₂ O were added, and the reaction was stirred at 90 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 11.4 g (yield 69.5%) of <Compound 247>.

LC/MS: m/z=731 [(M+1) ⁺ ]

Synthesis example 8: Synthesis of compound 249

(One) production example 1: Synthesis of Intermediate 249-1

Intermediate 247-1 (10.0 g, 0.036 mol), 4-(Dibenzofuranyl)boronic acid (9.1 g, 0.043 mol), K ₂ CO ₃ (14.8 g, 0.107 mol), catalyst Pd(OAc) ₂ (2.1 g, 0.002) mol), the ligand X-Phos (1.7 g, 0.004 mol), 200 mL of THF and 50 mL of H ₂ O were added, and the reaction was stirred at 90 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 7.5 g (yield 51.0%) of <Intermediate 249-1>.

(2) production example 2: Synthesis of compound 249

Intermediate 78-2 (10.0 g, 0.022 mol), Intermediate 249-1 (11.1 g, 0.027 mol), K ₂ CO ₃ (9.3 g, 0.067 mol), Catalyst Pd(OAc) ₂ (1.3 g, 0.001 mol), Ligand X-Phos (1.1 g, 0.002 mol), 200 mL of THF and 50 mL of H ₂ O were added, and the reaction was stirred at 90 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 10.2 g (yield: 65.4%) of <Compound 249>.

LC/MS: m/z=695[(M+1) ⁺ ]

Synthesis example 9: Synthesis of compound 380

(One) production example 1: Synthesis of intermediate 380-1

Intermediate 122-3 (10.0 g, 0.038 mol), Bis(4-biphenylyl)amine (18.3 g, 0.057 mol), NaOtBu (7.3 g, 0.076 mol), Pd(dba) ₂ (1.1 g, 0.002 mol), t 150 mL of Toluene was added to -Bu ₃ P (0.8 g, 0.004 mol), and the reaction was stirred at 70 °C for 4 hours. After completion of the reaction, 9.1 g (yield 43.8%) of <Intermediate 380-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) production example 2: Synthesis of compound 380

6-Phenyldibenzofuran-4-boronic acid (10.0 g, 0.035 mol), intermediate 380-1 (22.9 g, 0.042 mol), K ₂ CO ₃ (14.4 g, 0.104 mol), catalyst Pd(OAc) ₂ (2.0 g, 0.002 mol), the ligand X-Phos (1.7 g, 0.004 mol), 200 mL of THF and 50 mL of H ₂ O were added, and the reaction was stirred at 90° C. for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 15.3 g (yield 58.2%) of <Compound 380>.

LC/MS: m/z=756[(M+1) ⁺ ]

Synthesis example 10: Synthesis of compound 443

(One) production example 1: Synthesis of intermediate 443-1

Intermediate 122-3 (10.0 g, 0.038 mol), N-[1,1'-Biphenyl]-4-yl-3-dibenzofuranamine (19.1 g, 0.057 mol), NaOtBu (7.3 g, 0.076 mol), Pd(dba ) ₂ (1.1 g, 0.002 mol), t-Bu ₃ P (0.8 g, 0.004 mol) was added with 150 mL of Toluene and stirred at 70 °C for 4 hours to react. After completion of the reaction, 9.8 g (yield 45.9%) of <Intermediate 443-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) production example 2: Synthesis of compound 443

Intermediate 78-2 (10.0 g, 0.022 mol), Intermediate 443-1 (15.1 g, 0.027 mol), K ₂ CO ₃ (9.3 g, 0.067 mol), Catalyst Pd(OAc) ₂ (1.3 g, 0.001 mol), Ligand X-Phos (1.1 g, 0.002 mol), 200 mL of THF and 50 mL of H ₂ O were added, and the reaction was stirred at 90 °C for 6 hours. After completion of the reaction, 13.1 g (yield 69.0%) of <Compound 443> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=846[(M+1) ⁺ ]

Synthesis example 11: Synthesis of compound 567

(One) production example 1: Synthesis of intermediate 567-1

Intermediate 122-3 (10.0 g, 0.038 mol), N-[1,1'-Biphenyl]-2-yl-9,9-dimethyl-9H-fluoren-4-amine (20.5 g, 0.057 mol), NaOtBu ( Toluene 150 mL was added to 7.3 g, 0.076 mol), Pd(dba) ₂ (1.1 g, 0.002 mol), and t-Bu ₃ P (0.8 g, 0.004 mol), and the reaction was stirred at 70 °C for 4 hours. After completion of the reaction, 11.7 g (yield 52.5%) of <Intermediate 567-1> was obtained by extraction and concentration by column.

(2) production example 2: Synthesis of intermediate 567-2

4-Bromo-6-phenyldibenzothiophene (10.0 g, 0.030 mol), Bis(pinacolato)diboron (9.0 g, 0.035 mol), KOAc (8.7 g, 0.088 mol), Pd(dppf)Cl ₂ (1.1 g, 0.002 mol) 200 mL of dioxane was added, and the reaction was stirred at 100 °C for 12 hours. After completion of the reaction, 8.3 g (yield 72.9%) of <Intermediate 567-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) production example 3: Synthesis of compound 567

Intermediate 567-2 (10.0 g, 0.026 mol), Intermediate 567-1 (18.3 g, 0.031 mol), K ₂ CO ₃ (10.7 g, 0.078 mol), Catalyst Pd(OAc) ₂ (1.5 g, 0.001 mol), Ligand X-Phos (1.2 g, 0.003 mol), 200 mL of THF and 50 mL of H ₂ O were added, and the reaction was stirred at 90 °C for 6 hours. After completion of the reaction, 13.3 g (yield 63.2%) of <Compound 567> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=626[(M+1) ⁺ ]

Synthesis example 12: Synthesis of compound 629

(One) production example 1: Synthesis of intermediate 629-1

6-Phenyldibenzofuran-4-boronic acid (8.0 g, 0.035 mol), intermediate 122-3 (11.0 g, 0.042 mol), K ₂ CO ₃ (14.4 g, 0.104 mol), catalyst Pd(OAc) ₂ (2.0 g, 0.002 mol), the ligand X-Phos (1.7 g, 0.004 mol), 200 mL of THF and 50 mL of H ₂ O were added, and the reaction was stirred at 90° C. for 6 hours. After completion of the reaction, 7.5 g (yield 45.8%) of <Intermediate 629-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of intermediate 629-2

Intermediate 629-1 (10.0 g, 0.021 mol), Bis(pinacolato)diboron (6.5 g, 0.025 mol), CH ₃ COOK (4.2 g, 0.042 mol), Pd(dppf)Cl ₂ (0.5 g, 0.0006 mol), Dioxane was added to XPhos (0.4 g, 0.0008 mol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 8.7 g (yield 72.9%) of <Intermediate 629-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) production example 3: Synthesis of compound 629

Intermediate 629-2 (10.0 g, 0.018 mol), 2-Chloro-4,6-diphenyl-1,3,5-triazine (5.7 g, 0.021 mol), K ₂ CO ₃ (7.4 g, 0.053 mol), Pd (PPh ₃ ) ₄ (0.4 g, 0.0004 mol) was put into 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H ₂ O, followed by stirring at 100° C. for 6 hours. After completion of the reaction, 8.5 g (yield 71.6%) of <Compound 629> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=668[(M+1) ⁺ ]

Synthesis example 13: Synthesis of compound 668

(One) production example 1: Synthesis of intermediate 668-1

4,6-Dibromodibenzofuran (10.0 g, 0.031 mol), 4-Cyanobenzeneboronic acid (5.4 g, 0.037 mol), K ₂ CO ₃ (12.7 g, 0.092 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) Toluene 140 mL, EtOH 35 mL, H ₂ O 35 mL, and stirred for 6 hours at 100 ℃ reacted. After completion of the reaction, 5.2 g (yield 48.7%) of <Intermediate 668-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of intermediate 668-2

Intermediate 668-1 (10.0 g, 0.029 mol), Bis(pinacolato)diboron (8.8 g, 0.035 mol), KOAc (8.5 g, 0.086 mol), Pd(dppf)Cl ₂ (1.1 g, 0.001 mol) dioxane 200 mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, 8.1 g (yield 71.4%) of <Intermediate 668-2> was obtained by extraction and concentration by column.

(3) production example 3: Synthesis of intermediate 668-3

Intermediate 668-2 (10.0 g, 0.025 mol), Intermediate 247-1 (8.5 g, 0.030 mol), K ₂ CO ₃ (10.5 g, 0.076 mol), Catalyst Pd(OAc) ₂ (1.5 g, 0.001 mol), Ligand X-Phos (1.2 g, 0.003 mol), 200 mL of THF and 50 mL of H ₂ O were added, and the reaction was stirred at 90 °C for 6 hours. After completion of the reaction, 6.1 g (yield 47.0%) of <Intermediate 668-3> was obtained by extraction, concentration, and column.

(4) production example 4: Synthesis of intermediate 668-4

Intermediate 668-3 (10.0 g, 0.020 mol), Bis(pinacolato)diboron (5.9 g, 0.023 mol), CH ₃ COOK (3.8 g, 0.039 mol), Pd(dppf)Cl ₂ (0.4 g, 0.0006 mol), Dioxane was added to XPhos (0.3 g, 0.0007 mol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 8.9 g (yield 75.5%) of <Intermediate 668-4> was obtained by extraction and concentration, followed by column and recrystallization.

(5) production example 5: Synthesis of compound 668

Intermediate 668-4 (10.0 g, 0.017 mol), 2-Chloro-4,6-bis(3-dibenzofuranyl)-1,3,5-triazine (8.9 g, 0.020 mol), K ₂ CO ₃ (6.9 g, 0.050 mol), Pd(PPh ₃ ) ₄ (0.4 g, 0.0003 mol) was added to 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H ₂ O, followed by stirring at 100° C. for 6 hours. After completion of the reaction, 10.8 g (yield 73.4%) of <Compound 668> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=889[(M+1) ⁺ ]

Synthesis example 14: Synthesis of compound 738

(One) production example 1: Synthesis of intermediate 738-1

3,5-Dichlorobromobenzene (10.0 g, 0.044 mol), B-(2-Phenyl-6-benzoxazolyl)boronic acid (12.7 g, 0.053 mol), K ₂ CO ₃ (18.4 g, 0.133 mol), Pd(PPh ₃ ) ₄ (1.0 g, 0.0009 mol) was added to 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H ₂ O, followed by stirring at 100 °C for 6 hours. After completion of the reaction, 9.1 g (yield 60.4%) of <Intermediate 738-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of intermediate 738-2

6-Phenyldibenzofuran-4-boronic acid (10.0 g, 0.035 mol), intermediate 738-1 (14.2 g, 0.042 mol), K ₂ CO ₃ (14.4 g, 0.104 mol), catalyst Pd(OAc) ₂ (2.0 g, 0.002 mol), the ligand X-Phos (1.7 g, 0.004 mol), 200 mL of THF and 50 mL of H ₂ O were added, and the reaction was stirred at 90° C. for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and columned to obtain 8.6 g (yield: 45.2%) of <Intermediate 738-2>.

(3) production example 3: Synthesis of intermediate 738-3

Intermediate 738-3 (10.0 g, 0.018 mol), Bis(pinacolato)diboron (5.6 g, 0.022 mol), CH ₃ COOK (3.6 g, 0.037 mol), Pd(dppf)Cl ₂ (0.4 g, 0.0005 mol), Dioxane was added to XPhos (0.3 g, 0.0007 mol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 8.4 g (yield 72.0%) of <Intermediate 738-3> was obtained by extraction and concentration, followed by column and recrystallization.

(4) production example 4: Synthesis of compound 738

Intermediate 738-3 (10.0 g, 0.016 mol), 2-Chloro-4,6-bis(4-phenylphenyl)-1,3,5-triazine (7.9 g, 0.019 mol), K ₂ CO ₃ (6.5 g, 0.047 mol), Pd(PPh ₃ ) ₄ (0.4 g, 0.0003 mol) was added to 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H ₂ O, followed by stirring at 100° C. for 6 hours. After completion of the reaction, 10.5 g (yield 74.9%) of <Compound 738> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=896[(M+1) ⁺ ]

Synthesis example 15: Synthesis of compound 756

(One) production example 1: Synthesis of intermediate 756-1

Intermediate 738-1 (10.0 g, 0.029 mol), Bis(4-biphenylyl)amine (14.2 g, 0.044 mol), NaOtBu (5.7 g, 0.059 mol), Pd(dba) ₂ (0.9 g, 0.002 mol), t 150 mL of Toluene was added to -Bu ₃ P (0.6 g, 0.003 mol), and the reaction was stirred at 70 °C for 4 hours. After completion of the reaction, 8.9 g (yield 48.4%) of <Intermediate 756-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) production example 2: Synthesis of compound 756

6-Phenyldibenzofuran-4-boronic acid (10.0 g, 0.035 mol), intermediate 756-1 (26.0 g, 0.042 mol), K ₂ CO ₃ (14.4 g, 0.104 mol), catalyst Pd(OAc) ₂ (2.0 g, 0.002 mol), the ligand X-Phos (1.7 g, 0.004 mol), 200 mL of THF and 50 mL of H ₂ O were added, and the reaction was stirred at 90° C. for 6 hours. After completion of the reaction, 21.1 g (yield 73.0%) of <Compound 756> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=832 [(M+1) ⁺ ]

device Example (CPL)

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

device Example 1 to 31

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

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

[HAT-CN] was formed on a glass substrate to a thickness of 5 nm on an ITO transparent electrode containing Ag to form a hole injection layer, and then [α-NPB] was formed to a thickness of 100 nm to form a hole transport layer, [TCTA] was formed into a film to a thickness of 10 nm to form an electron-blocking layer, and then [BH1] as a host compound and [BD1] as a dopant compound were co-deposited at 20 nm to form an emission layer. After depositing an electron transport layer (50% doped with [201] compound Liq below) at 30 nm, LiF was deposited to a thickness of 1 nm to form an electron injection layer. Then, Mg:Ag was formed into a film to a thickness of 15 nm in a ratio of 1:9 to form a cathode.

And as for the light efficiency improving layer (capping layer), the compound according to the present invention described in [Table 1] was formed into a film to a thickness of 70 nm to prepare an organic light emitting diode.

device comparative example One

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

device comparative example 2

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

Experimental Example 1: Light emission characteristics of device Examples 1 to 31

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

Example Light Efficiency Improvement Layer V cd/A CIEx CIEy One Formula 1 3.6 8.6 0.143 0.053 2 Formula 24 3.5 8.8 0.139 0.061 3 Formula 36 3.7 8.7 0.141 0.056 4 Formula 45 3.4 8.8 0.139 0.061 5 chemical formula 57 3.5 8.4 0.144 0.050 6 Formula 67 3.8 8.7 0.141 0.054 7 Formula 72 3.6 8.4 0.146 0.054 8 Formula 78 3.8 9.0 0.139 0.062 9 Formula 85 3.6 8.6 0.141 0.057 10 Formula 99 3.5 8.8 0.138 0.049 11 Formula 101 3.7 9.0 0.137 0.060 12 Formula 117 3.6 8.8 0.139 0.048 13 Formula 120 3.8 8.3 0.146 0.059 14 Formula 122 3.5 8.7 0.138 0.060 15 Formula 124 3.6 9.0 0.137 0.054 16 Formula 141 3.7 8.8 0.141 0.061 17 Formula 150 3.4 8.6 0.143 0.059 18 Formula 177 3.5 8.4 0.140 0.051 19 Formula 186 3.8 9.0 0.139 0.048 20 Formula 189 3.6 8.9 0.143 0.056 21 Formula 237 3.4 8.6 0.141 0.053 22 Formula 247 3.5 8.9 0.146 0.061 23 Formula 249 3.6 8.7 0.140 0.049 24 Formula 252 3.8 8.8 0.138 0.052 25 Formula 261 3.4 9.0 0.137 0.049 26 Formula 267 3.5 8.4 0.142 0.061 27 Formula 288 3.6 8.9 0.146 0.059 28 Formula 297 3.4 8.4 0.135 0.060 29 Formula 315 3.5 8.9 0.139 0.047 30 Formula 330 3.5 9.0 0.141 0.056 31 Formula 344 3.8 8.8 0.139 0.061 Comparative Example 1 not used 4.6 7.0 0.150 0.141 Comparative Example 2 Alq ₃ 4.3 7.8 0.147 0.058

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

[HAT-CN] [α-NPB] [BH1] [BD1] [201]

[TCTA]

device Example ( HTL )

In an embodiment according to the present invention, the ITO transparent electrode is patterned so that the light emitting area is 2 mm × 2 mm on a glass substrate of 25 mm × 25 mm × 0.7 mm, using an ITO glass substrate to which an ITO transparent electrode is attached. and then washed. After the substrate was mounted in a vacuum chamber, the base pressure was set to 1 × 10 ^-6 torr, and the organic material and the metal were deposited on the ITO in the following structure.

device Example 32 to 60

The compound implemented according to the present invention was employed in the hole transport layer to fabricate an organic light emitting device having the following device structure, and then, light emission and driving characteristics of the compound implemented according to the present invention were measured.

ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (100 nm) / electron blocking layer (EBL1, 10 nm) / light emitting layer (20 nm) / electron transport layer (201:Liq, 30 nm) / LiF (1 nm) / Al (100 nm)

[HAT-CN] was formed on top of the ITO transparent electrode to a thickness of 5 nm to form a hole injection layer, and then the compound according to the present invention described in [Table 2] was formed at 100 nm to form a hole transport layer, and then [EBL1] was formed into a film to a thickness of 10 nm to form an electron blocking layer, and [BH1] as a host compound and [BD1] as a dopant compound were co-deposited at 20 nm to form an emission layer. After depositing an electron transport layer (50% doping of [201] compound Liq below) at 30 nm, LiF was deposited to a thickness of 1 nm to form an electron injection layer. Then, Al was formed into a film to a thickness of 100 nm to fabricate an organic light emitting diode.

device comparative example 3

The organic light emitting device for Device Comparative Example 3 was manufactured in the same manner except that α-NPB was used as the hole transport layer material in the device structures of Examples 32 to 60.

Experimental Example 2: Emission characteristics of device examples 32 to 60

The organic light emitting device manufactured according to the above example was measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research) to measure driving voltage, current efficiency, and color coordinates, and the result value based on 1,000 nits is shown in [Table 2] below.

Example hole transport layer V cd/A CIEx CIEy 32 Formula 376 3.8 7.8 0.136 0.150 33 Formula 380 3.7 7.5 0.134 0.151 34 Formula 397 3.8 8.1 0.135 0.148 35 Formula 402 4.0 7.6 0.135 0.149 36 Formula 407 3.9 8.1 0.138 0.147 37 Formula 423 4.0 7.5 0.134 0.151 38 Formula 441 3.7 7.6 0.137 0.150 39 Formula 443 4.0 7.6 0.135 0.149 40 Formula 468 3.7 8.0 0.132 0.152 41 Formula 492 3.8 7.7 0.135 0.147 42 Formula 500 3.5 8.0 0.134 0.152 43 Formula 502 4.0 7.8 0.135 0.147 44 Formula 513 3.9 8.1 0.133 0.145 45 Formula 527 3.6 7.5 0.137 0.150 46 Formula 530 3.7 7.8 0.136 0.148 47 Formula 536 3.6 7.8 0.134 0.149 48 Formula 542 3.8 8.1 0.137 0.145 49 Formula 551 4.0 7.6 0.136 0.152 50 Formula 553 3.6 7.5 0.131 0.147 51 Formula 558 3.6 7.8 0.133 0.149 52 Formula 560 4.0 7.5 0.136 0.152 53 Formula 562 3.9 7.8 0.132 0.147 54 Formula 567 3.6 7.8 0.133 0.145 55 Formula 577 3.7 8.1 0.135 0.150 56 Formula 581 3.6 7.6 0.134 0.148 57 Formula 590 3.8 7.5 0.135 0.146 58 Formula 596 4.0 7.8 0.132 0.148 59 Formula 756 3.6 8.1 0.137 0.152 60 Formula 761 3.6 7.5 0.136 0.147 Comparative Example 3 α-NPB 4.7 6.6 0.135 0.151

Looking at the results shown in [Table 2], in the case of the device employed in the hole transport layer in the compound organic light emitting device according to the present invention, compared to the device employing α-NPB used as a conventional hole transport material (Comparative Example 3) It can be seen that the characteristics such as driving voltage and luminous efficiency are remarkably excellent.

[HAT_CN] [α-NPB] [BH1] [BD1] [201]

[EBL1]

device Example ( ETL )

In an embodiment according to the present invention, the ITO transparent electrode is patterned so that the light emitting area is 2 mm × 2 mm on a glass substrate of 25 mm × 25 mm × 0.7 mm, using an ITO glass substrate to which an ITO transparent electrode is attached. and then washed. After the substrate was mounted in a vacuum chamber, the base pressure was set to 1 × 10 ^-6 torr or more, and the organic material and the metal were deposited on the ITO in the following structure.

device Example 61 to 83

After manufacturing an organic light emitting device having the following device structure by using the compound implemented according to the present invention as an electron transport layer, light emission and driving characteristics of the compound implemented according to the present invention were measured.

ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (α-NPB, 100 nm) / electron blocking layer (EBL1 10 nm) / light emitting layer (20 nm) / electron transport layer (201:Liq, 30 nm) / LiF (1 nm) / Al (100 nm)

To form a hole injection layer on the ITO transparent electrode, [HAT-CN] was used to deposit at 5 nm, and then the hole transport layer was deposited at 100 nm using α-NPB. The electron blocking layer was deposited to a thickness of 10 nm using [EBL1]. In addition, [BH1] was used as a host compound for the light emitting layer, and [BD1] was used as a dopant compound to be co-deposited to a thickness of 20 nm. In addition, the electron transport layer was deposited at 30 nm (Liq doping) using the compound according to the present invention described in Table 3 below, and then LiF was deposited to a thickness of 1 nm to form an electron injection layer. Then, Al was formed into a film to a thickness of 100 nm to fabricate an organic light emitting diode.

device comparative example 4

The organic light emitting device for Device Comparative Example 4 was manufactured in the same manner except that the following [ET1] was used instead of the compound according to the present invention as the electron transport layer material in the device structures of Examples 21 to 40.

Experimental example 3: element Example luminescence properties of 61 to 83

The organic light emitting device manufactured according to the above example was measured for voltage, current and luminous efficiency using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), and the result value based on 1000 nit was It is shown in [Table 3] below.

Example electron transport layer V cd/A CIEx CIEy 61 Formula 600 3.9 7.4 0.133 0.155 62 Formula 605 3.6 7.9 0.134 0.150 63 Formula 622 3.8 7.8 0.136 0.153 64 Formula 629 3.7 7.6 0.132 0.156 65 Formula 635 3.9 8.1 0.134 0.152 66 Formula 644 3.7 7.5 0.133 0.156 67 Formula 653 3.6 7.6 0.135 0.147 68 Formula 659 3.7 7.6 0.137 0.134 69 Formula 660 3.8 7.7 0.135 0.153 70 Formula 662 3.9 7.6 0.132 0.156 71 Formula 668 3.8 7.5 0.131 0.151 72 Formula 670 3.9 7.7 0.132 0.153 73 Formula 679 3.8 8.1 0.135 0.157 74 Formula 682 3.5 7.6 0.136 0.149 75 Formula 688 3.8 7.9 0.131 0.156 76 chemical formula 700 3.6 7.7 0.132 0.150 77 Formula 718 3.9 7.4 0.134 0.151 78 Formula 726 4.0 7.8 0.137 0.150 79 Formula 733 3.7 7.4 0.136 0.155 80 Formula 736 4.0 8.1 0.134 0.157 81 Formula 737 3.6 7.6 0.135 0.154 82 Formula 738 3.8 7.8 0.136 0.153 83 Formula 742 3.9 7.9 0.131 0.154 Comparative Example 4 ET1 4.6 6.8 0.134 0.149

Looking at the results shown in [Table 3], in the case of the device employing the compound according to the present invention to the electron transport layer in the organic light emitting device, compared to the device employing the electron transport material (Comparative Example 4), the driving voltage, luminous efficiency, quantum It can be seen that the luminous properties such as efficiency are remarkably excellent.

[HAT_CN] [α-NPB] [BH1] [BD1] [EBL1]

[ET1]

Claims (9)

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

In the [Formula I],
Any one of A and B is represented by the following [Structural Formula 1], and the other one is a cyano group, a halogen group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, A substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C6 to C30 Any one selected from an arylamine group, a substituted or unsubstituted C3 to C30 heteroarylamine group, and a substituted or unsubstituted C6 to C30 arylheteroarylamine group,
[Structural Formula 1]

In the [Structural Formula 1],
X is O or S;
R ₁ to R ₅ are the same as or different from each other, and each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, Any one selected from a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C3 to C30 heteroaryl group,
Any one of R ₁ to R ₅ is bonded at the A or B position of the [Formula I],
Y is any one selected from O, S, NR ₆ and CR ₇ R ₈ ,
wherein R ₆ to R ₈ are the same as or different from each other, and each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C 1 to C 20 alkyl group, or a substituted or unsubstituted C 3 to C 20 cycloalkyl group , is any one selected from a substituted or unsubstituted C 6 to C 30 aryl group and a substituted or unsubstituted C 3 to C 30 heteroaryl group,
R is a cyano group, a halogen group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, a substituted or unsubstituted C 1 to C 20 alkoxy group, a substituted or unsubstituted Any one selected from an aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms. According to claim 1,
In the definition of A, B, R ₁ to R ₈ and R, 'substituted or unsubstituted' means that A, B, R ₁ to R ₈ and R are deuterium, a halogen group, a cyano group, a nitro group, Hydroxy group, amine group, alkyl group, halogenated alkyl group, deuterated alkyl group, cycloalkyl group, heterocycloalkyl group, alkoxy group, halogenated alkoxy group, deuterated alkoxy group, aryl group, heteroaryl group, alkylsilyl group and arylsilyl group An organic light-emitting compound, characterized in that it is substituted with one or two or more substituents selected from the group consisting of a group, or is substituted with a substituent to which two or more of the substituents are connected, or does not have any substituents. The method of claim 1,
The [Formula I] is an organic light emitting compound, characterized in that selected from the following [Compound 1] to [Compound 765]:

An organic light emitting device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode,
At least one of the organic layers is an organic light emitting device comprising the organic light emitting compound of [Formula I] according to claim 1. 5. The method of claim 4,
The organic layer is selected from a hole injection layer, a hole transport layer, a layer that performs both hole injection and hole transport functions, an electron transport layer, an electron injection layer, a layer that performs both electron transport and electron injection functions, an electron blocking layer, a hole blocking layer and a light emitting layer including one or more floors that become
At least one of the layers comprises an organic light emitting compound represented by the [Formula I]. 6. The method of claim 5,
An organic light emitting device comprising an organic light emitting compound represented by the [Formula I] in the hole transport layer or a layer that performs both hole injection and hole transport functions at the same time. 6. The method of claim 5,
An organic light emitting device comprising an organic light emitting compound represented by the [Formula I] in the electron transport layer or a layer that performs both electron transport and electron injection functions. 5. The method of claim 4,
Further comprising a light efficiency improvement layer (Capping Layer) formed on at least one side opposite to the organic layer among the upper or lower portions of the first electrode and the second electrode,
The light efficiency improving layer is an organic light emitting device, characterized in that it comprises an organic light emitting compound represented by the [Formula I]. 9. The method of claim 8,
The light efficiency improving layer is an organic light emitting device, characterized in that formed on at least one of a lower portion of the first electrode or an upper portion of the second electrode.