KR20220166394A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to: a novel organic light emitting compound which is represented by chemical formula I, and can realize luminous properties such as low voltage driving and excellent luminous efficiency of an organic light emitting device by being applied to organic layers such as a hole transport layer and an electron transport layer in the organic light emitting device; and the organic light emitting device comprising the same.

Description

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

The present invention relates to an organic light-emitting compound, and more particularly, to an organic light-emitting compound characterized in that it is employed as an organic layer material in an organic light-emitting device, and organic light-emitting properties such as low-voltage driving of the device and excellent light-emitting efficiency are remarkably improved by employing the organic light-emitting compound. It is about light emitting devices.

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

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

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

In this regard, studies have recently been actively conducted to improve the mobility of existing organic materials for the hole transport layer material in the structure of the organic light emitting device.

Therefore, the present invention provides a novel organic light emitting compound capable of realizing excellent light emitting characteristics such as low voltage driving and improved light emitting efficiency by being employed in an organic layer such as a hole transport layer and an electron transport layer in an organic light emitting device, and an organic light emitting device including the same. want to provide

In order to solve the above problems, the present invention provides an organic light emitting device including an organic light emitting compound represented by the following [Chemical Formula I] and an organic layer such as a hole transport layer and an electron transport layer in the device.

[Formula I]

The characteristic structure of [Chemical Formula 1] and the definitions of the compounds, X, Y, A, and Ar ₁ to Ar ₂ implemented thereby will be described later.

When the organic light emitting compound according to the present invention is used as a material for an organic layer such as a hole transport layer and an electron transport layer in an organic light emitting device, low voltage driving of the device and luminous properties such as excellent luminous efficiency can be implemented, so that it can be usefully used in various display devices. there is.

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] capable of achieving light emitting characteristics such as low voltage driving of an organic light emitting device and excellent light emitting efficiency, and structurally having a skeleton structure represented by [Formula I] That is, it is characterized in that a characteristic substituent is introduced into the structure of an oxazolocarbazole or thiazolocarbazole derivative, and through this structural feature, low-voltage driving characteristics and luminous efficiency characteristics of an organic light emitting device can be improved.

[Formula I]

In the above [Formula I],

One of X and Y is N, and the other is O or S. According to an embodiment of the present invention, [Formula I] is any one selected from the following [Formula I-1] to [Formula I-12] can be one

[Formula Ⅰ-1] [Formula Ⅰ-2]

[Formula Ⅰ-3] [Formula Ⅰ-4]

[Formula I-5] [Formula Ⅰ-6]

[Formula Ⅰ-7] [Formula Ⅰ-8]

[Formula Ⅰ-9] [Formula Ⅰ-10]

[Formula Ⅰ-11] [Formula Ⅰ-12]

In [Formula I], [Formula I-1] to [Formula I-12],

Ar ₁ and Ar ₂ are the same as or different from each other, and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

A is 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 arylamine group having 6 to 30 carbon atoms, or a substituted or unsubstituted 3 to 30 carbon atoms It is selected from a heteroarylamine group of 6 to 30 substituted or unsubstituted arylheteroarylamine groups.

According to one embodiment of the present invention, the A may be any one selected from the following [Structural Formula 1] to [Structural Formula 3].

[Structural Formula 1]

[Structural Formula 2]

[Structural Formula 3]

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

L ₁ to L ₃ are the same as or different from each other, and are each independently selected from a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

Ar ₃ to Ar ₈ are the same as or different from each other, and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

Meanwhile, in the definition of A, L ₁ to L ₃ and Ar ₁ to Ar ₈ , 'substituted or unsubstituted' means that A, L ₁ to L ₃ and Ar ₁ to Ar ₈ are deuterium and halogen groups, respectively. , Cyano group, nitro group, hydroxyl group, alkyl group, halogenated alkyl group, deuterated alkyl group, cycloalkyl group, heterocycloalkyl group, alkoxy group, halogenated alkoxy group, deuterated alkoxy group, amine group, aryl group, heteroaryl group , It means that it is substituted with one or two or more substituents selected from the group consisting of an alkylsilyl group and an arylsilyl group, is substituted with a substituent in which two or more substituents are connected, or does not have any substituent.

For example, a 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, and the like 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 condensed heterocyclic groups thereof, such as a benzquinoline group. , It means that a benzimidazole group, a benzoxazole group, a benzthiazole group, a benzcarbazole group, a dibenzothiophenyl group, a dibenzofuran group, and the like are substituted with other substituents.

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

In the present invention, the alkyl group may be straight 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 chain. The number of carbon atoms in the alkoxy group is not particularly limited, but 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 , benzyloxy group, p-methylbenzyloxy group, etc., but is not limited thereto.

In the present invention, a deuterated alkyl or alkoxy group, a halogenated alkyl or alkoxy group means an alkyl or alkoxy group in which the alkyl or alkoxy group is substituted with deuterium or a halogen group.

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

,

,

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

,

,

etc.

,

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

,

etc.

,

,

,

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

,

,

,

etc.

In the present invention, the heteroaryl group is a heterocyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, and is a polycyclic group in which cycloalkyl or heterocycloalkyl is fused. It includes a heteroaryl group structure, and specific examples thereof in the present invention include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, and a bipyridyl group. , pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, Dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, phenoxazine group, phenothiazine group, etc., but only these It is not limited.

In the present invention, the silyl group is an unsubstituted silyl group or a silyl group substituted with an alkyl group, an aryl group, etc., and specific examples of such a silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxy phenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, and the like, but are not limited thereto.

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

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

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

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

The organic light emitting compound according to the present invention represented by [Chemical Formula I] can be used as various organic layers including hole transport layers and electron transport layers in organic light emitting devices due to its structural specificity.

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

As described above, the organic light emitting compound according to the present invention can synthesize organic light emitting compounds having various properties by using a characteristic skeleton exhibiting unique properties and a moiety having unique properties introduced thereto, As a result, the organic light-emitting compound according to the present invention can be applied to various organic layer materials such as a light emitting layer, a hole transport layer, an electron transport layer, an electron blocking layer, and a hole blocking layer, and preferably a hole transport or electron transport material, such as the luminous efficiency of a device, etc. It is possible to further improve the luminescent properties of.

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

An organic light emitting device according to an embodiment of the present invention may have a structure including a first electrode, a second electrode, and an organic layer disposed therebetween, and the organic light emitting compound according to the present invention is used in the organic layer of the device. Except for this, it can be manufactured using conventional device manufacturing methods and materials.

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

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

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

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

The cathode material is preferably a material having a small work function so as to easily inject electrons into the organic layer. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof, and multilayers such as LiF/Al or LiO ₂ /Al. structural materials, etc., but are not limited thereto.

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

As the hole transport material, a material capable of receiving holes transported from the anode or the hole injection layer and transferring them to the light emitting layer, and a material having high hole mobility is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts. can be further improved.

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

As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable, and the compound according to the present invention may be used, or may be used together with conventional compounds there is. Specific examples of such conventional compounds include Al complexes of 8-hydroxyquinoline, complexes containing Alq ₃ , organic radical compounds, hydroxyflavone-metal complexes, etc., but are not limited thereto, and organic light emitting compounds according to the present invention It is possible to further improve the low-voltage driving characteristics, luminous efficiency, and lifespan characteristics of the device by using.

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

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

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

synthesis example 1: Synthesis of Compound 2

(One) manufacturing example 1: Synthesis of Intermediate 2-1

2-Amino-6-bromo-3-chlorophenol (10.0 g, 0.045 mol), Benzaldehyde (4.8 g, 0.045 mol), p-Toluenesulfonic acid (1.6 g, 0.009 mol), and 200 mL of DMF were added and heated at 80 °C for 2 hours. reacted by stirring. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 9.8 g of <Intermediate 2-1> (yield: 70.7%).

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

Dioxane 200 in intermediate 2-1 (10.0 g, 0.032 mol), Bis(pinacolato)diboron (9.9 g, 0.039 mol), KOAc (9.5 g, 0.097 mol), Pd(dppf)Cl ₂ (1.2 g, 0.002 mol) mL was added and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 8.3 g of <Intermediate 2-2> (yield: 72.0%).

(3) manufacturing example 3: Synthesis of Intermediate 2-3

1-Bromo-2-nitrobenzene (10.0 g, 0.050 mol), intermediate 2-2 (21.1 g, 0.059 mol), K ₂ CO ₃ (20.5 g, 0.148 mol), Pd(PPh ₃ ) ₄ (1.1 g, 0.001 mol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 100 °C for 6 hours. After completion of the reaction, 13.4 g (yield 77.2%) of <Intermediate 2-3> was obtained by extraction, concentration, and column.

(4) manufacturing example 4: synthesis of intermediates 2-4

Intermediate 2-3 (10.0 g, 0.029 mol), PPh ₃ (18.7 g, 0.071 mol), and 200 mL of dichlorobenzene were added and stirred under reflux for 5 hours to react. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 6.2 g of <Intermediate 2-4> (yield: 68.2%).

(5) manufacturing example 5: synthesis of intermediates 2-5

155 mL of DMF was added to Intermediate 2-4 (10.0 g, 0.031 mol), 4-Fluorobiphenyl (6.5 g, 0.038 mol), and Cs ₂ CO ₃ (6.5 g, 0.047 mol), and reacted by stirring under reflux for 12 hours. After completion of the reaction, 10.5 g (yield 71.1%) of <Intermediate 2-5> was obtained by extraction, concentration, column and recrystallization.

(6) manufacturing example 6: Synthesis of Compound 2

Intermediate 2-5 (10.0 g, 0.021 mol), Phenylboronic acid (3.1 g, 0.026 mol), K ₂ CO ₃ (8.8 g, 0.064 mol), Catalyst Pd(OAc) ₂ (1.2 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, followed by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted and concentrated, followed by column and recrystallization to obtain 7.2 g of <Compound 2> (yield: 66.2%).

LC/MS: m/z = 512 [(M) ⁺ ]

synthesis example 2: synthesis of compound 13

(One) manufacturing example 1: synthesis of intermediate 13-1

155 mL of DMF was added to Intermediate 2-4 (10.0 g, 0.031 mol), Fluorobenzene (3.6 g, 0.038 mol), and Cs ₂ CO ₃ (6.5 g, 0.047 mol), and reacted by stirring under reflux for 12 hours. After completion of the reaction, 8.7 g (yield: 70.2%) of <Intermediate 13-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) manufacturing example 2: synthesis of compound 13

Intermediate 13-1 (10.0 g, 0.025 mol), 4-(10-Phenylanthracen-9-yl)benzeneboronic acid (11.4 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 reacted by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted and concentrated, and then column and recrystallized to obtain 11.7 g of <Compound 13> (yield: 67.1%).

LC/MS: m/z=688 [(M) ⁺ ]

synthesis example 3: synthesis of compound 23

(One) manufacturing example 1: synthesis of intermediate 23-1

2-Amino-3-bromo-6-chlorophenol (10.0 g, 0.045 mol), Benzaldehyde (4.8 g, 0.045 mol), p-Toluenesulfonic acid (1.6 g, 0.009 mol), and 200 mL of DMF were added and heated at 80 °C for 2 hours. reacted by stirring. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 10.1 g of <Intermediate 23-1> (yield: 72.8%).

(2) manufacturing example 2: synthesis of intermediate 23-2

Intermediate 23-1 (10.0 g, 0.032 mol), Bis(pinacolato)diboron (9.9 g, 0.039 mol), KOAc (9.5 g, 0.097 mol), Dioxane 200 in Pd(dppf)Cl ₂ (1.2 g, 0.002 mol) mL was added and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 8.7 g of <Intermediate 23-2> (yield: 75.5%).

(3) manufacturing example 3: synthesis of intermediate 23-3

1-Bromo-2-nitrobenzene (10.0 g, 0.050 mol), Intermediate 23-2 (21.1 g, 0.059 mol), K ₂ CO ₃ (20.5 g, 0.148 mol), Pd(PPh ₃ ) ₄ (1.1 g, 0.001 mol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 12.4 g of <Intermediate 23-3> (yield: 71.4%).

(4) manufacturing example 4: synthesis of intermediate 23-4

Intermediate 23-3 (10.0 g, 0.029 mol), PPh ₃ (18.7 g, 0.071 mol), and 200 mL of dichlorobenzene were added and stirred under reflux for 5 hours to react. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 6.1 g of <Intermediate 23-4> (yield: 67.1%).

(5) manufacturing example 5: synthesis of intermediate 23-5

Intermediate 23-4 (10.0 g, 0.031 mol), 5'-Fluoro-1,1:3',1"-terphenyl (9.3 g, 0.038 mol), Cs ₂ CO ₃ (6.5 g, 0.047 mol) in DMF 155 After the completion of the reaction, extraction and concentration were carried out, followed by column and recrystallization to obtain 12.2 g of <Intermediate 23-5> (yield: 71.1%).

(6) manufacturing example 6: synthesis of compound 23

Intermediate 23-5 (10.0 g, 0.025 mol), Phenylboronic acid (3.7 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, followed by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 10.3 g of <Compound 23> (yield: 69.1%).

LC/MS: m/z=588 [(M) ⁺ ]

synthesis example 4: synthesis of compound 53

(One) manufacturing example 1: synthesis of intermediate 53-1

155 mL of DMF was added to Intermediate 23-4 (10.0 g, 0.031 mol), Fluorobenzene (3.6 g, 0.038 mol), and Cs ₂ CO ₃ (6.5 g, 0.047 mol), and reacted by stirring under reflux for 12 hours. After completion of the reaction, 9.3 g (yield 75.1%) of <Intermediate 53-1> was obtained by extraction, concentration, and column.

(2) manufacturing example 2: synthesis of intermediate 53-2

Intermediate 53-1 (10.0 g, 0.025 mol), Bis(pinacolato)diboron (17.4 g, 0.030 mol), CH ₃ COOK (5.0 g, 0.051 mol), Pd(dppf)Cl ₂ (0.6 g, 0.001 mol), Dioxane was added to the ligand X-Phos (0.4 g, 0.001 mol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 8.8 g of <Intermediate 53-2> (yield: 71.4%).

(3) manufacturing example 3: synthesis of intermediate 53-3

1,3,5-Tribromobenzene (10.0 g, 0.032 mol), Intermediate 53-2 (18.5 g, 0.038 mol), K ₂ CO ₃ (13.2 g, 0.095 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.001 mol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 7.8 g of <Intermediate 53-3> (yield: 41.3%).

(4) manufacturing example 4: synthesis of intermediate 53-4

Intermediate 53-3 (10.0 g, 0.017 mol), 4-(Pyridin-3-yl)phenylboronic acid (8.0 g, 0.040 mol), K ₂ CO ₃ (14.0 g, 0.101 mol), Pd(PPh ₃ ) ₄ ( 0.4 g, 0.0003 mol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 100 °C for 6 hours. After completion of the reaction, 9.7 g (yield 77.6%) of <Compound 53> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=742 [(M) ⁺ ]

synthesis example 5: Synthesis of Compound 105

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

2,4-Dichloro-6-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine (10.0 g, 0.029 mol), 4-Biphenylboronic acid (6.9 g, 0.035 mol) Toluene 200 mL, EtOH 50 mL, and H ₂ O 50 mL were added to K ₂ CO ₃ (12.1 g, 0.088 mol) and Pd(PPh ₃ ) ₄ (0.7 g, 0.001 mol), followed by stirring at 100 °C for 6 hours. reacted After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 6.8 g of <Intermediate 105-1> (yield: 50.6%).

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

Intermediate 105-1 (10.0 g, 0.022 mol), 1,4-Phenylenediboronic acid (4.3 g, 0.026 mol), K ₂ CO ₃ (9.0 g, 0.065 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.0004 mol) ) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 100 °C for 6 hours. After completion of the reaction, 7.9 g (yield 66.6%) of <Intermediate 105-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) manufacturing example 3: Synthesis of compound 105

Intermediate 13-1 (10.0 g, 0.025 mol), Intermediate 105-2 (16.6 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, followed by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 13.8 g of <Compound 105> (yield: 63.4%).

LC/MS: m/z=859 [(M) ⁺ ]

synthesis example 6: synthesis of compound 120

(One) manufacturing example 1: synthesis of intermediate 120-1

2,4-Dichloro-6-(3-dibenzofuranyl)-1,3,5-triazine (10.0 g, 0.032 mol), 4-Biphenylboronic acid (7.5 g, 0.038 mol), K ₂ CO ₃ (13.1 g, 0.095 mol) and Pd(PPh ₃ ) ₄ (0.7 g, 0.001 mol), 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O were added, followed by stirring at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 7.3 g of <Intermediate 120-1> (yield: 53.2%).

(2) manufacturing example 2: synthesis of intermediate 120-2

Intermediate 120-1 (10.0 g, 0.023 mol), 1,4-Phenylenediboronic acid (4.6 g, 0.028 mol), K ₂ CO ₃ (9.6 g, 0.069 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.001 mol) ) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 100 °C for 6 hours. After completion of the reaction, 8.2 g (yield 68.5%) of <Intermediate 120-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) manufacturing example 3: Synthesis of Compound 120

Intermediate 53-1 (10.0 g, 0.025 mol), Intermediate 120-2 (15.8 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, followed by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 15.1 g of <Compound 120> (yield: 71.5%).

LC/MS: m/z=833 [(M) ⁺ ]

synthesis example 6: Synthesis of Compound 163

(One) manufacturing example 1: synthesis of intermediate 163-1

2-Amino-6-bromo-4-chlorophenol (10.0 g, 0.045 mol), Benzaldehyde (4.8 g, 0.045 mol), p-Toluenesulfonic acid (1.6 g, 0.009 mol), and 200 mL of DMF were added and heated at 80 °C for 2 hours. reacted by stirring. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 9.8 g of <Intermediate 163-1> (yield: 70.7%).

(2) manufacturing example 2: synthesis of intermediate 163-2

Intermediate 163-1 (10.0 g, 0.032 mol), Bis(pinacolato)diboron (9.9 g, 0.039 mol), KOAc (9.5 g, 0.097 mol), Dioxane 200 in Pd(dppf)Cl ₂ (1.2 g, 0.002 mol) mL was added and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 8.4 g of <Intermediate 163-2> (yield: 72.9%).

(3) manufacturing example 3: synthesis of intermediate 163-3

1-Bromo-2-nitrobenzene (10.0 g, 0.050 mol), intermediate 163-2 (21.1 g, 0.059 mol), K ₂ CO ₃ (20.5 g, 0.149 mol), Pd(PPh ₃ ) ₄ (1.1 g, 0.001 mol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 12.3 g of <Compound 163-3> (yield: 70.8%).

(4) manufacturing example 4: synthesis of intermediate 163-4

Intermediate 163-3 (10.0 g, 0.029 mol), PPh ₃ (18.7 g, 0.071 mol), and 200 mL of dichlorobenzene were added and stirred under reflux for 5 hours to react. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 6.0 g of <Intermediate 163-4> (yield: 66.0%).

(5) manufacturing example 5: synthesis of intermediate 163-5

155 mL of DMF was added to Intermediate 163-4 (10.0 g, 0.031 mol), Fluorobenzene (3.6 g, 0.038 mol), and Cs ₂ CO ₃ (6.5 g, 0.047 mol), and reacted by stirring under reflux for 12 hours. After completion of the reaction, 8.9 g (yield 71.9%) of <Intermediate 163-5> was obtained by extraction and concentration, followed by column and recrystallization.

(6) manufacturing example 6: Synthesis of Compound 163

Intermediate 163-5 (10.0 g, 0.025 mol), (4'-(Diphenylamino)-[1,1'-biphenyl]-4-yl)boronic acid (11.1 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), THF 200 mL, and H ₂ O 50 mL were added and stirred at 90 °C for 6 hours. reacted After completion of the reaction, the mixture was extracted and concentrated, followed by column and recrystallization to obtain 11.5 g of <Compound 163> (yield: 66.8%).

LC/MS: m/z=679 [(M) ⁺ ]

synthesis example 7: synthesis of compound 181

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

1,4-Dibromobenzene (10.0 g, 0.042 mol), N-(Biphenyl-2-yl)dibenzo[b,d]furan-3-amine (21.3 g, 0.064 mol), NaOtBu (12.2 g, 0.127 mol), 150 mL of Toluene was added to Pd(dba) ₂ (1.0 g, 0.0017 mol) and t-Bu ₃ P (0.7 g, 0.0034 mol), followed by stirring at 70 °C for 4 hours. After completion of the reaction, after extraction and concentration, 13.2 g (yield 63.5%) of <Intermediate 181-1> was obtained by column.

(2) manufacturing example 2: synthesis of intermediate 181-2

Intermediate 181-1 (10.0 g, 0.020 mol), Bis(pinacolato)diboron (6.2 g, 0.025 mol), KOAc (6.0 g, 0.061 mol), Dioxane 200 in Pd(dppf)Cl ₂ (0.8 g, 0.001 mol) mL was added and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 7.7 g (yield 70.3%) of <Intermediate 181-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) manufacturing example 3: Synthesis of compound 181

Intermediate 13-1 (10.0 g, 0.025 mol), Intermediate 181-2 (16.3 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, followed by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 12.3 g of <Compound 181> (yield: 63.1%).

LC/MS: m/z=769 [(M) ⁺ ]

synthesis example 8: Synthesis of compound 200

(One) manufacturing example 1: Synthesis of Compound 200

Intermediate 53-1 (10.0 g, 0.025 mol), 2-(2-Biphenylyl)amino-9,9-dimethylfluorene (13.7 g, 0.038 mol), NaOtBu (7.3 g, 0.076 mol), Pd(dba) ₂ (0.6 g, 0.001 mol) and t-Bu ₃ P (0.4 g, 0.002 mol) were added with 150 mL of Toluene, followed by stirring at 70 °C for 4 hours. After completion of the reaction, 13.2 g (yield 72.4%) of <Compound 200> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=719 [(M) ⁺ ]

synthesis example 9: synthesis of compound 212

(One) manufacturing example 1: synthesis of intermediate 212-1

Add 2-Amino-6-bromo-3-chlorobenzene-1-thiol (10.0 g, 0.042 mol), Benzaldehyde (4.5 g, 0.042 mol), p-Toluenesulfonic acid (1.4 g, 0.008 mol), and 200 mL of DMF. The mixture was reacted by stirring at 80 °C for 1 hour. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 9.4 g of <Intermediate 212-1> (yield: 69.1%).

(2) manufacturing example 2: synthesis of intermediate 212-2

Intermediate 212-1 (10.0 g, 0.031 mol), Bis(pinacolato)diboron (9.4 g, 0.037 mol), KOAc (9.1 g, 0.092 mol), Dioxane 200 in Pd(dppf)Cl ₂ (1.1 g, 0.002 mol) mL was added and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 8.3 g of <Intermediate 212-2> (yield: 72.5%).

(3) manufacturing example 3: synthesis of intermediate 212-3

1-Bromo-2-nitrobenzene (10.0 g, 0.050 mol), intermediate 212-2 (22.1 g, 0.059 mol), K ₂ CO ₃ (20.5 g, 0.149 mol), Pd(PPh ₃ ) ₄ (1.1 g, 0.001 mol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 12.7 g of <Compound 212-3> (yield: 69.9%).

(4) manufacturing example 4: synthesis of intermediate 212-4

Intermediate 212-3 (10.0 g, 0.027 mol), PPh ₃ (17.9 g, 0.068 mol), and 200 mL of dichlorobenzene were added and stirred under reflux for 5 hours to react. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 5.9 g of <Intermediate 212-4> (yield: 64.6%).

(5) manufacturing example 5: synthesis of intermediate 212-5

155 mL of DMF was added to Intermediate 212-4 (10.0 g, 0.030 mol), 1-Fluoronaphthalene (5.2 g, 0.036 mol), and Cs ₂ CO ₃ (6.2 g, 0.045 mol), followed by stirring under reflux for 12 hours. After completion of the reaction, 9.7 g (yield 70.5%) of <Intermediate 212-5> was obtained by extraction and concentration, followed by column and recrystallization.

(6) manufacturing example 6: synthesis of compound 212

Intermediate 212-5 (10.0 g, 0.022 mol), 4-Biphenylboronic acid (5.2 g, 0.026 mol), K ₂ CO ₃ (9.0 g, 0.065 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, followed by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 8.5 g of <Compound 212> (yield: 67.7%).

LC/MS: m/z=578 [(M) ⁺ ]

synthesis example 10: synthesis of compound 289

(One) manufacturing example 1: synthesis of intermediate 289-1

155 mL of DMF was added to Intermediate 212-4 (10.0 g, 0.030 mol), Fluorobenzene (3.4 g, 0.036 mol), and Cs ₂ CO ₃ (6.2 g, 0.045 mol), and reacted by stirring under reflux for 12 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 8.9 g of <Intermediate 289-1> (yield: 72.5%).

(2) manufacturing example 2: synthesis of intermediate 289-2

2,4-Dichloro-6-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine (10.0 g, 0.029 mol), 9,9-Dimethylfluoren-2-boronic acid ( 8.4 g, 0.035 mol), K ₂ CO ₃ (12.1 g, 0.088 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.001 mol), 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O were added and stirred for 6 hours. While stirring at 100 ℃ was reacted. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 8.6 g of <Compound 289-2> (yield: 58.9%).

(3) manufacturing example 3: synthesis of intermediate 289-3

Intermediate 289-2 (10.0 g, 0.020 mol), 1,4-Phenylenediboronic acid (4.0 g, 0.024 mol), K ₂ CO ₃ (8.3 g, 0.060 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.0004 mol) ) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, and reacted by stirring at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 7.8 g of <Intermediate 289-3> (yield: 66.6%).

(4) manufacturing example 4: Synthesis of Compound 289

Intermediate 289-1 (10.0 g, 0.024 mol), Intermediate 289-3 (17.1 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, followed by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 16.2 g of <Compound 289> (yield: 72.7%).

LC/MS: m/z=915 [(M) ⁺ ]

synthesis example 11: synthesis of compound 293

(One) manufacturing example 1: synthesis of intermediate 293-1

Intermediate 289-1 (10.0 g, 0.024 mol), Bis(pinacolato)diboron (16.8 g, 0.029 mol), CH ₃ COOK (4.8 g, 0.049 mol), Pd(dppf)Cl ₂ (0.5 g, 0.001 mol), Dioxane was added to the ligand X-Phos (0.4 g, 0.001 mol) and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 8.6 g (yield 70.3%) of <Intermediate 293-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) manufacturing example 2: Synthesis of Compound 293

2-Chloro-4,6-di(naphthalen-2-yl)-1,3,5-triazine (10.0 g, 0.027 mol), intermediate 293-1 (16.4 g, 0.033 mol), K ₂ CO ₃ (11.3 g, 0.082 mol) and Pd(PPh ₃ ) ₄ (0.6 g, 0.001 mol) were added with 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours. After completion of the reaction, 13.2 g (yield 68.6%) of <Compound 293> was obtained by extraction and concentration, followed by column and recrystallization.

synthesis example 12: synthesis of compound 356

(One) manufacturing example 1: synthesis of intermediate 356-1

2-Bromo-9,9'-spirobi[9H-fluorene] (10.0 g, 0.025 mol), 2-Aminobiphenyl (6.4 g, 0.038 mol), NaOtBu (7.3 g, 0.076 mol), Pd(dba) ₂ (0.6 g, 0.001 mol) and t-Bu ₃ P (0.4 g, 0.002 mol) were added with 150 mL of Toluene, followed by stirring at 70 °C for 4 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 7.4 g of <Intermediate 356-1> (yield: 60.5%).

(2) manufacturing example 2: synthesis of intermediate 356-2

1,4-Dibromobenzene (10.0 g, 0.042 mol), intermediate 356-1 (30.8 g, 0.064 mol), NaOtBu (12.2 g, 0.127 mol), Pd(dba) ₂ (1.0 g, 0.0017 mol), t-Bu 150 mL of Toluene was added to ₃ P (0.7 g, 0.0034 mol), followed by stirring at 70 °C for 4 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 17.9 g of <Intermediate 356-2> (yield: 66.1%).

(3) manufacturing example 3: synthesis of intermediate 356-3

Intermediate 356-2 (10.0 g, 0.016 mol), Bis(pinacolato)diboron (4.8 g, 0.019 mol), KOAc (4.6 g, 0.047 mol), Dioxane 200 in Pd(dppf)Cl ₂ (0.6 g, 0.001 mol) mL was added and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 8.2 g (yield 76.4%) of <Intermediate 356-3> was obtained by extraction and concentration, followed by column and recrystallization.

(4) manufacturing example 4: compound 356 synthesis

Intermediate 289-1 (10.0 g, 0.024 mol), Intermediate 356-3 (20.0 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, followed by stirring at 90 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 15.5 g of <Compound 356> (yield: 68.2%).

LC/MS: m/z = 933 [(M) ⁺ ]

device Example ( HTL )

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

device Example 1 to 50

After employing the compound implemented according to the present invention as a hole transport layer and manufacturing an organic light emitting device having the following device structure, 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 (ET1:Liq, 30 nm) / LiF (1 nm) / Al (100 nm)

[HAT-CN] was formed on top of the ITO transparent electrode to form a hole injection layer with a thickness of 5 nm, and then the compound according to the present invention described in [Table 1] was formed to a thickness of 100 nm to form a hole transport layer. Thereafter, [EBL1] was deposited to a thickness of 10 nm to form an electron blocking layer, and an emission layer was formed by co-evaporation to a thickness of 20 nm using [BH1] as a host compound and [BD1] as a dopant compound. Thereafter, an electron transport layer (the [ET1] compound Liq 50% doped) was deposited to a thickness of 30 nm, and then LiF was deposited to a thickness of 1 nm to form an electron injection layer. Thereafter, an Al film was formed to a thickness of 100 nm to fabricate an organic light emitting device.

device comparative example One

The organic light emitting device for Device Comparative Example 1 was manufactured in the same manner as in the device structures of Examples 1 to 50, except that [α-NPB] was used instead of the compound according to the present invention in the hole transport layer.

device comparative example 2

The organic light emitting device for Device Comparative Example 2 was manufactured in the same manner as in the device structures of Examples 1 to 50, except that [HT 1] was used instead of the compound according to the present invention in the hole transport layer.

Experimental example 1: element Example Luminescence characteristics from 1 to 50

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

Example hole transport layer V cd/A CIEx CIEy One Formula 2 3.70 7.66 0.1313 0.1342 2 Formula 8 3.67 7.98 0.1333 0.1364 3 Formula 23 3.64 7.50 0.1317 0.1358 4 Formula 32 3.92 7.87 0.1340 0.1376 5 Formula 126 3.48 7.64 0.1329 0.1380 6 Formula 134 3.67 7.38 0.1334 0.1317 7 Formula 135 3.81 7.43 0.1342 0.1388 8 Formula 136 4.03 7.28 0.1348 0.1347 9 Formula 139 3.96 7.78 0.1334 0.1360 10 Formula 152 3.72 7.56 0.1325 0.1341 11 Formula 156 3.79 7.79 0.1314 0.1347 12 Formula 162 3.67 7.61 0.1333 0.1311 13 Formula 164 3.83 7.94 0.1333 0.1335 14 Formula 170 3.42 7.83 0.1320 0.1375 15 Formula 172 3.73 7.68 0.1303 0.1347 16 Formula 173 3.59 7.34 0.1325 0.1360 17 Formula 174 3.58 7.67 0.1341 0.1311 18 Formula 181 3.67 7.82 0.1303 0.1392 19 Formula 185 3.98 7.87 0.1302 0.1386 20 Formula 186 3.77 7.48 0.1311 0.1404 21 Formula 188 3.96 7.81 0.1283 0.1408 22 Formula 192 3.80 7.61 0.1309 0.1345 23 Formula 193 3.78 7.76 0.1293 0.1375 24 Formula 194 3.52 7.78 0.1301 0.1388 25 Formula 195 4.08 7.30 0.1311 0.1369 26 Formula 197 3.85 7.31 0.1295 0.1375 27 chemical formula 200 3.67 7.58 0.1317 0.1339 28 Formula 204 3.62 8.18 0.1306 0.1363 29 Formula 207 3.89 7.39 0.1295 0.1385 30 Formula 216 3.62 7.63 0.1329 0.1379 31 Formula 220 3.58 7.38 0.1294 0.1397 32 Formula 241 4.08 7.60 0.1298 0.1382 33 Formula 304 3.73 7.54 0.1285 0.1395 34 Formula 310 3.49 7.79 0.1313 0.1376 35 Formula 311 3.60 7.63 0.1294 0.1382 36 Formula 312 3.85 7.41 0.1307 0.1346 37 Formula 318 3.89 7.38 0.1315 0.1370 38 Formula 326 4.05 7.46 0.1330 0.1335 39 Formula 330 3.98 7.96 0.1316 0.1348 40 Formula 333 3.74 7.74 0.1307 0.1329 41 Formula 347 3.81 7.97 0.1296 0.1335 42 Formula 349 3.69 7.79 0.1315 0.1299 43 Formula 356 3.85 8.12 0.1315 0.1323 44 Formula 357 3.44 8.01 0.1302 0.1363 45 Formula 359 3.75 7.86 0.1285 0.1335 46 Formula 363 3.61 7.52 0.1307 0.1348 47 Formula 364 3.60 7.85 0.1323 0.1299 48 Formula 365 3.69 8.00 0.1285 0.1380 49 Formula 366 4.00 8.05 0.1284 0.1374 50 Formula 367 3.79 7.66 0.1293 0.1392 Comparative Example 1 α-NPB 4.67 6.65 0.1353 0.1517 Comparative Example 2 HT 1 4.71 6.49 0.1349 0.1520

Looking at the results shown in [Table 1], when the hole transport layer according to the present invention is applied to a compound device, a device employing a compound used as a conventional hole transport material or a compound that contrasts with the characteristic structure of the compound according to the present invention Compared to (Comparative Examples 1 and 2), it can be confirmed that the driving voltage is reduced and the current efficiency is improved.

[HAT_CN] [α-NPB] [BH1] [BD1] [ET1]

[EBL1] [HT 1]

device Example ( ETL )

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

device Example 51 to 100

After fabricating an organic light emitting device having the following device structure using the compound implemented according to the present invention as an electron transport material, 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)

In order to form a hole injection layer on the ITO transparent electrode, [HAT-CN] was deposited to a thickness of 5 nm, and then a hole transport layer was formed using α-NPB to a thickness of 100 nm. 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 the dopant compound to have a thickness of 20 nm, and the electron transport layer was composed of the compounds according to the present invention as shown in [Table 2] below. After depositing 30 nm (Liq doped) using , LiF was deposited to a thickness of 1 nm to form an electron injection layer. Thereafter, an Al film was formed to a thickness of 100 nm to fabricate an organic light emitting device.

device comparative example 3

The organic light emitting device for Device Comparative Example 3 was manufactured in the same manner as in the device structures of Examples 51 to 100, except that [ET1] was used instead of the compound according to the present invention for the electron transport layer.

Experimental example 2: device Example Luminescent properties of 51 to 100

Voltage, current, and luminous efficiency were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research) for the organic light emitting device manufactured according to the above Examples and Comparative Examples, based on 1000 nit The result values are shown in [Table 2] below.

Example electron transport layer V cd/A CIEx CIEy 51 Formula 1 4.00 7.75 0.1329 0.1353 52 Formula 3 3.76 7.53 0.1320 0.1334 53 Formula 13 3.83 7.96 0.1309 0.1340 54 Formula 26 3.71 7.58 0.1328 0.1304 55 Formula 42 3.87 7.91 0.1328 0.1328 56 Formula 44 3.46 7.80 0.1315 0.1368 57 Formula 45 3.77 7.65 0.1298 0.1340 58 Formula 48 3.63 7.31 0.1320 0.1353 59 Formula 52 3.62 7.64 0.1336 0.1304 60 Formula 53 3.71 7.79 0.1298 0.1385 61 Formula 54 4.02 7.84 0.1297 0.1379 62 Formula 55 3.81 7.45 0.1326 0.1397 63 Formula 70 3.74 7.63 0.1308 0.1335 64 Formula 72 3.71 7.95 0.1328 0.1357 65 Formula 74 3.68 7.47 0.1312 0.1351 66 Formula 76 3.96 7.84 0.1335 0.1369 67 Formula 83 3.52 7.61 0.1324 0.1373 68 chemical formula 100 3.71 7.75 0.1329 0.1310 69 Formula 105 3.85 7.40 0.1337 0.1381 70 Formula 106 4.07 7.55 0.1343 0.1340 71 Formula 107 3.64 7.60 0.1289 0.1375 72 Formula 116 3.89 7.38 0.1302 0.1339 73 Formula 117 3.93 7.35 0.1310 0.1363 74 Formula 120 4.09 7.43 0.1325 0.1328 75 Formula 123 4.02 7.93 0.1311 0.1341 76 Formula 212 3.78 7.71 0.1302 0.1322 77 Formula 215 3.85 7.94 0.1291 0.1328 78 Formula 217 3.73 7.26 0.1310 0.1292 79 Formula 250 4.00 7.38 0.1278 0.1401 80 Formula 255 3.84 7.59 0.1304 0.1338 81 Formula 265 3.82 7.73 0.1288 0.1368 82 Formula 267 3.56 7.35 0.1296 0.1381 83 Formula 268 4.16 7.27 0.1306 0.1362 84 Formula 269 3.89 7.28 0.1290 0.1368 85 Formula 270 3.71 7.55 0.1312 0.1332 86 Formula 273 3.66 8.15 0.1301 0.1356 87 Formula 274 3.93 7.36 0.1390 0.1378 88 Formula 275 3.66 7.60 0.1324 0.1372 89 Formula 276 3.62 7.35 0.1289 0.1390 90 Formula 281 4.23 7.57 0.1293 0.1375 91 Formula 287 3.77 7.51 0.1380 0.1388 92 Formula 289 3.53 7.76 0.1308 0.1369 93 Formula 291 3.86 7.39 0.1386 0.1326 94 Formula 293 3.84 7.91 0.1370 0.1356 95 Formula 298 3.58 7.93 0.1378 0.1369 96 Formula 399 4.14 7.45 0.1288 0.1350 97 chemical formula 300 3.91 7.46 0.1372 0.1356 98 Formula 301 3.94 7.17 0.1333 0.1347 99 Formula 302 3.91 8.03 0.1306 0.1341 100 Formula 303 3.78 7.94 0.1380 0.1359 Comparative Example 3 ET 1 4.67 6.65 0.1353 0.1517

Looking at the results shown in [Table 2], in the case of an organic light emitting device employing the compound according to the present invention in the electron transport layer in the device, the driving voltage compared to the device employing the compound used as the conventional electron transport material (Comparative Example 3) It can be seen that this decreases and the current efficiency improves.

[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 above [Formula I],
One of X and Y is N, the other is O or S,
Ar ₁ and Ar ₂ are the same as or different from each other, and are each independently any one selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,
A is 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 arylamine group having 6 to 30 carbon atoms, or a substituted or unsubstituted 3 to 30 carbon atoms It is any one selected from a heteroarylamine group of 6 to 30 substituted or unsubstituted arylheteroarylamine groups. According to claim 1,
[Formula I] is an organic light emitting compound represented by any one selected from the following [Formula I-1] to [Formula I-12]:
[Formula I-1] [Formula I-2]

[Formula Ⅰ-3] [Formula Ⅰ-4]

[Formula Ⅰ-5] [Formula Ⅰ-6]

[Formula Ⅰ-7] [Formula Ⅰ-8]

[Formula Ⅰ-9] [Formula Ⅰ-10]

[Formula Ⅰ-11] [Formula Ⅰ-12]

In [Formula I-1] to [Formula I-12], A, Ar ₁ and Ar ₂ are the same as defined in [Formula I]. According to claim 1,
Wherein A is an organic light-emitting compound, characterized in that any one selected from the following [Structural Formula 1] to [Structural Formula 3]:
[Structural Formula 1]

[Structural Formula 2]

[Structural Formula 3]

In [Structural Formula 1] to [Structural Formula 3],
L ₁ to L ₃ are the same as or different from each other, and are each independently any one selected from a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms; ,
Ar ₃ to Ar ₈ are the same as or different from each other, and are each independently any one selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. According to any one of claims 1 to 3,
In the definition of A, L ₁ to L ₃ and Ar ₁ to Ar ₈ , 'substituted or unsubstituted' means that A, L ₁ to L ₃ and Ar ₁ to Ar ₈ are deuterium, a halogen group, or cyanide, respectively. No group, nitro group, hydroxyl group, alkyl group, halogenated alkyl group, deuterated alkyl group, cycloalkyl group, heterocycloalkyl group, alkoxy group, halogenated alkoxy group, deuterated alkoxy group, amine group, aryl group, heteroaryl group, alkyl 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 silyl group and an arylsilyl group, or is substituted with a substituent in which two or more substituents are connected, or does not have any substituents. According to claim 1,
[Formula I] is an organic light-emitting compound, characterized in that any one selected from the following [Compound 1] to [Compound 367]:

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,
At least one of the organic layers comprises an organic light emitting compound of [Chemical Formula I] according to claim 1. According to claim 6,
The organic layer is selected from a hole injection layer, a hole transport layer, a layer that simultaneously performs hole injection and hole transport functions, an electron transport layer, an electron injection layer, a layer that simultaneously performs electron transport and electron injection functions, an electron blocking layer, a hole blocking layer, and a light emitting layer. Including one or more floors,
An organic light emitting device, wherein at least one of the layers includes the organic light emitting compound represented by [Chemical Formula I]. According to claim 7,
An organic light emitting device comprising the organic light emitting compound represented by the [Chemical Formula I] in any one of the hole transport layer, the hole injection layer, and the hole transport and hole injection layers. According to claim 7,
An organic light emitting device comprising the organic light emitting compound represented by [Chemical Formula I] in any one of the electron transport layer, the electron injection layer, and the electron transport and electron injection layer.