KR20240023369A - Organic compound and electroluminescent device comprising the same - Google Patents

Abstract

The present invention is an organic compound represented by the following [Chemical Formula I], and when it is used in an organic layer, preferably an electron blocking layer, in an organic light-emitting device, an organic light-emitting device with excellent luminous properties such as luminous efficiency and quantum efficiency can be realized. possible.
[Formula Ⅰ]

Description

Organic compound and electroluminescent device comprising the same}

The present invention relates to organic compounds, and more specifically, to organic compounds employed in organic layers such as electron blocking layers in organic light-emitting devices, and to organic light-emitting devices whose device characteristics, such as low-voltage operation, long life, and luminous efficiency, are significantly improved by employing the same. It's about.

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

However, in order for this organic light-emitting device to exhibit the above characteristics, the materials that make up the organic layer within the device, such as hole injection material, hole transport material, hole blocking material, light emitting material, electron transport material, electron injection material, and electron blocking material, are required. Support by stable and efficient materials should be a priority, but the development of stable and efficient organic layer materials for organic light-emitting devices has not yet been sufficiently developed.

Therefore, there is a continued need for the development of new materials that can improve luminescence characteristics and the development of organic layer structures within devices.

In particular, in order to achieve higher luminous efficiency, there is a need for the development of materials that can be more appropriately used as an electron blocking layer as well as an increase in hole mobility so that they can be used as a hole injection layer or hole transport layer.

Therefore, the present invention aims to provide an organic compound that can be used as an organic layer material such as an electron blocking layer in an organic light-emitting device to significantly improve device characteristics such as low-voltage driving characteristics, long life, and luminous efficiency, and an organic light-emitting device containing the same. do.

In order to solve the above problems, the present invention provides an organic compound represented by the following [Chemical Formula I] and an organic light-emitting device comprising the same in an electron blocking layer.

[Formula Ⅰ]

The specific structure of [Chemical Formula I], the specific compounds implemented thereby, and the definitions of R ₁ to R ₃ , R _A , Ar ₁ to Ar ₃ , D (deuterium), and n will be described later.

The organic compound according to the present invention has excellent hole injection and transport performance, high triplet exciton confinement performance, excellent electron blocking performance, and excellent stability in a thin film state, and is used as an electron blocking layer, hole transport layer, etc. Organic light-emitting devices used in the organic layer have significantly superior device characteristics such as low-voltage operation, long lifespan, and luminous efficiency compared to conventional devices, and can be usefully used in various lighting devices and display devices.

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

The present invention relates to a novel organic compound capable of realizing an organic light-emitting device with significantly improved device characteristics such as low-voltage operation, long life, and luminous efficiency when applied to various organic layers in an organic light-emitting device, preferably an electron blocking layer. , It is characterized by being represented by the following [Chemical Formula I].

The compound of [Chemical Formula I] according to the present invention has excellent hole injection and transport performance, high triplet exciton confinement performance, excellent electron blocking performance, and excellent stability in a thin film state, so it is adopted as an electron blocking layer. This makes it possible to implement organic light-emitting devices with high luminous efficiency.

[Formula Ⅰ]

In the above [Chemical Formula I],

Ar ₁ to Ar ₃ are the same 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 3 to 30 carbon atoms.

R _A is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted fluorene, and substituted or unsubstituted dibenzofuran.

R ₁ to R ₃ are the same or different from each other and are hydrogen or deuterium, respectively.

According to one embodiment of the present invention, R _A may be any one selected from [Structural Formula 1] to [Structural Formula 6] below.

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

[Structural Formula 4] [Structural Formula 5] [Structural Formula 6]

Among the [Structural Formula 1] to [Structural Formula 6],

_{and _ _ _} In any one of the above, R ₄ and R ₅ may be connected to each other to form a ring.

Each R is independently selected from hydrogen, deuterium, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a plurality of R in each structural formula is the same or different from each other.

n is an integer from 0 to 5, m is an integer from 0 to 7, o is an integer from 0 to 4, and p is an integer from 0 to 3.

In addition, D is deuterium, n refers to the number of hydrogens in the formula (I) replaced with deuterium (D), and n is an integer from 0 to 60.

According to one embodiment of the present invention, the compound represented by [Formula I] may contain at least one or more deuterium in the [Formula I] structure, that is, the compound represented by [Formula I] may have a skeleton as well as a skeleton. and is characterized in that it is a compound in which the hydrogens present in the substituents defined in the structure of [Formula I] are each partially substituted with deuterium (D), and as a result, an organic light-emitting device with superior luminous efficiency and significantly improved lifespan characteristics can be implemented.

According to one embodiment of the present invention, the deuterium (D) substitution rate may be 10 to 90%, according to a preferred embodiment, the deuterium (D) substitution rate may be 20 to 80%, and according to a more preferred embodiment, the deuterium (D) substitution rate may be 10 to 90%. D) The substitution rate may be 30 to 70%.

Meanwhile, in the definitions of Ar ₁ to Ar ₃ , R _A , R, R ₄ and R ₅ , substituted or unsubstituted means that Ar ₁ to Ar ₃ , R _A , R, R ₄ and R ₅ are respectively deuterium and cyanohydride. One or two or more substituents selected from the group consisting of a nitro group, a halogen group, a hydroxy group, a nitro group, an alkyl group, an alkoxy group, a halogenated alkoxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a fluorenyl group, a heteroaryl group, a silyl group, and an amine group. It means that it is substituted with a substituent, or is substituted with a substituent in which two or more of the above substituents are linked, or does not have any substituent.

For specific examples, a substituted aryl group refers to a phenyl group, biphenyl group, naphthalene group, fluorenyl group, pyrenyl group, phenanthrenyl group, perylene group, tetracenyl group, anthracenyl group, etc. substituted with another substituent such as deuterium. means, and substituted heteroaryl group refers to pyridyl group, thiophenyl group, triazine group, quinoline group, phenanthroline group, imidazole group, thiazole group, oxazole group, carbazole group and condensed heterocyclic groups thereof, such as This means that benzquinoline group, benzimidazole group, benzoxazole group, benzthiazole group, benzcarbazole group, dibenzothiophenyl group, dibenzofuran group, etc. are also substituted with other substituents such as deuterium.

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

In the present invention, the alkyl group may be straight chain 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, etc., but is not limited to these.

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 within 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, the alkyl group and the alkoxy group may be a deuterated alkyl group or alkoxy group, a halogenated alkyl group, or an alkoxy group, respectively, and the alkyl group or alkoxy group refers to an alkyl group or alkoxy group substituted with a deuterium or 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. It also includes a polycyclic aryl group structure fused with cycloalkyl, etc., and the monocyclic aryl group Examples of phenyl group, biphenyl group, terphenyl group, stilbene group, etc. Examples of polycyclic aryl groups include naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, tetracenyl group, and chrysenyl group. , fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthrene group, etc., but the scope of the present invention is not limited to these examples.

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 the structure of an open fluorenyl group, where the open fluorenyl group is a structure in which one ring compound is disconnected in a structure where two ring organic compounds are connected through one atom. , for example

, etc.

Additionally, the carbon atom of the ring may be substituted with one or more heteroatoms selected from N, S, and O, for example , , , etc.

Additionally, in the present invention, the fluorenyl group may have a structure in which a monocyclic or polycyclic aromatic ring and a monocyclic or polycyclic alicyclic ring, etc. are further condensed to the above connected structure or open structure.

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 is preferably 2 to 30 carbon atoms, and is a polycyclic group fused with cycloalkyl or heterocycloalkyl, etc. It contains a heteroaryl group structure, and specific examples thereof in the present invention include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, and 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, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole 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. Specific examples of such silyl groups include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, and dimethoxysilyl. Examples include phenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, etc., but are not limited thereto.

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

In the present invention, cycloalkyl groups refer to and include monocyclic, polycyclic and spiro alkyl radicals, and preferably contain ring carbon atoms having 3 to 20 carbon atoms, such as cyclopropyl, cyclopentyl, cyclohexyl, and bicyclo. It includes heptyl, spirodecyl, spiroundecyl, adamantyl, etc., 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, wherein one or more heteroatoms are O, S, N, P, B, Si and Se, It is preferably selected from O, N or S, and specifically, when it contains N, it may be aziridine, pyrrolidine, piperidine, azepane, azocan, etc.

In the present invention, the amine group may be -NH ₂ , an alkylamine group, an arylamine group, an arylheteroarylamine group, etc., an arylamine group refers to an amine substituted with aryl, and an alkylamine group refers to an amine substituted with alkyl. The arylheteroarylamine group refers to an amine substituted with aryl and heteroaryl groups. Examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or There is an unsubstituted triarylamine group, and the aryl group and heteroaryl group in the arylamine group and arylheteroarylamine group may be a monocyclic aryl group, a monocyclic heteroaryl group, or a polycyclic aryl group or a polycyclic heteroaryl group. and the aryl group, the arylamine group containing two or more heteroaryl groups, and the arylheteroarylamine group include a monocyclic aryl group (heteroaryl group), a polycyclic aryl group (heteroaryl group), or a monocyclic aryl group (heteroaryl group). It may contain both an aryl group) and a polycyclic aryl group (heteroaryl group). In addition, the aryl group and heteroaryl group of the arylamine group and the arylheteroarylamine group may be selected from examples of the above-mentioned aryl group and heteroaryl group.

Additionally, various specific examples of substituents according to the present invention can be clearly identified in the specific compounds described below.

As described above, the organic compound according to the present invention represented by [Chemical Formula I] can be used as an organic layer of an organic light-emitting device due to its structural specificity, and more specifically, electron blocking of the organic layer depending on the characteristics of various substituents introduced. It can be used as a material for layers, etc.

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

Through the above-mentioned characteristic skeletal structure and substituents, organic compounds with unique properties of the skeletal structure and substituents can be synthesized. For example, when manufacturing an organic light-emitting device, an organic compound material that satisfies the conditions required for each organic layer can be manufactured. In particular, when the compound of [Chemical Formula I] according to the present invention is used in the electron blocking layer, etc., device characteristics such as luminous efficiency of the device can be further improved.

The organic compound according to the present invention can be applied to an organic light-emitting device according to a conventional manufacturing method.

The 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 between them, except that the organic compound according to the present invention is used in the organic layer of the device. 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 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, etc. However, it is not limited to this and may include fewer or more organic layers.

As such, the organic light emitting device according to an embodiment of the present invention may include a hole injection layer, a hole transport layer, a light emitting layer, etc. formed on an anode, and may also include a hole blocking layer, an electron injection layer, an electron transport layer, an electron blocking layer, It may include a light emitting auxiliary layer, etc., but is not limited thereto.

Therefore, in the organic light emitting device according to the present invention, the organic layer may include an electron blocking layer, etc., and one or more of the layers may include the organic compound represented by [Chemical Formula I].

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

In addition to this method, an organic light-emitting device can also be made 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 hole blocking layer, a light emitting layer, an electron blocking layer, an electron transport layer, an electron blocking layer, etc., but is not limited to this and may have a single layer structure. In addition, the organic layer uses a variety of polymer materials and is formed using a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, to form a smaller number of layers. It can be manufactured in layers.

The anode is usually preferably a material with a large work function to ensure smooth hole injection into the organic layer. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof, 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) , conductive polymers such as polypyrrole and polyaniline, but are not limited to these.

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

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

The hole transport layer is a material that can transport holes from the anode or hole injection layer and transfer them to the light emitting layer, and a material with high mobility for holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.

The electron blocking layer is a layer that blocks the movement of electrons and can be formed on the hole transport layer. An electron blocking layer that can block the movement of electrons without affecting the transport of holes can be used. Additionally, a light-emitting layer may be formed on the electron blocking layer, and a hole blocking layer, an electron transport layer, and an electron injection layer may be formed.

The hole blocking layer can be used to prevent the movement of holes without affecting the transport of electrons. An example of such a hole blocking layer is TPBi (1,3,5-tri(1-phenyl-1H-benzo). [d]imidazol-2-yl)phenyl), BCP (2,9-dimethyl4,7-diphenyl-1,10-phenanthroline), CBP (4,4-bis(N-carbazolyl)-1,1'-biphenyl ), PBD (2-(4-biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole), PTCBI (bisbenzimidazo[2,1-a:1',2-b']anthra [2,1,9-def:6,5,10-d'e'f']diisoguinoline-10,21-dione) or BPhen (4,7-diphenyl-1,10-phenanthroline), etc. It is not limited.

The light-emitting layer is a material that can emit light in the visible light range by transporting holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining them, and a material with 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 Examples include benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, and rubrene, but are not limited to these.

The electron injection layer can be one that has high injection efficiency of electrons transferred from the cathode. Examples of such electron injection layers include, but are not limited to, lithium quinolate (Liq).

The electron transport layer is a material that can easily receive electrons from the cathode and transfer them to the light emitting layer, and a material with 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, and a hydroxyflavone-metal complex.

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

In addition, the organic compound according to the present invention can function in organic electronic devices, including organic solar cells, organic photoreceptors, organic transistors, etc., on a principle similar to that applied to organic light-emitting devices.

Hereinafter, synthesis examples of preferred compounds and device examples are presented to aid understanding of the present invention. However, the following examples are for illustrating the present invention and are not intended to limit the scope of the present invention.

Synthesis example 1: Synthesis of Compound 6

(One) Manufacturing example 1: Synthesis of intermediate 6-1

B-(9-Phenyl-9H-carbazol-4-yl)boronic acid (10.0 g, 0.035 mol), 3-Bromo-5-chloro-1,1'-biphenyl (11.2 g, 0.042 mol), K ₂ CO ₃ (14.4 g, 0.105 mol) and Pd(PPh ₃ ) ₄ (0.8 g, 0.0007 mol) were added with 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 9.6 g of <Intermediate 6-1> (yield 64.1%).

(2) Manufacturing example 2 : Synthesis of Compound 6

Intermediate 6-1 (10.0 g, 0.023 mol), Bis(4-biphenylyl)amine (11.2 g, 0.035 mol), NaOtBu (6.7 g, 0.070 mol), Pd(dba) ₂ (0.5 g, 0.9 mmol), t 150 mL of Xylene was added to -Bu ₃ P (0.4 g, 1.9 mmol) and stirred at 120°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 12.2 g of <Compound 6> (yield 73.4%).

LC/MS: m/z=714[(M) ⁺ ]

Synthesis example 2: Synthesis of Compound 13

(One) Manufacturing example 1: Synthesis of Compound 13

Intermediate 6-1 (10.0 g, 0.023 mol), N-[1,1'-Biphenyl]-4-yl[1,1':2',1"-terphenyl]-4'-amine (13.9 g, 0.035 mol), NaOtBu (6.7 g, 0.070 mol), Pd(dba) ₂ (0.5 g, 0.9 mmol), t-Bu ₃ P (0.4 g, 1.9 mmol), add 150 mL of After the reaction was completed, the extract was extracted, concentrated, and recrystallized with a column to obtain 13.1 g of <Compound 13> (yield 71.2%).

LC/MS: m/z=790[(M) ⁺ ]

Synthesis example 3: Synthesis of Compound 41

(One) Manufacturing example 1: Synthesis of Compound 41

Intermediate 4-1 (10.0 g, 0.023 mol), N-(Biphenyl-2-yl)dibenzo[b,d]furan-3-amine (11.7 g, 0.035 mol), NaOtBu (6.7 g, 0.070 mol), Pd (dba) ₂ (0.5 g, 0.9 mmol) and t-Bu ₃ P (0.4 g, 1.9 mmol) were mixed with 150 mL of xylene and stirred at 120°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 12.1 g of <Compound 41> (yield 71.4%).

LC/MS: m/z=728[(M) ⁺ ]

Synthesis example 4: Synthesis of Compound 90

(One) Manufacturing example 1: Synthesis of intermediate 90-1

B-(9-Phenyl-9H-carbazol-4-yl)boronic acid (10.0 g, 0.035 mol), 3,5-dibromochlorobenzene (11.3 g, 0.042 mol), K ₂ CO ₃ (14.4 g, 0.105 mol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added to Pd(PPh ₃ ) ₄ (0.8 g, 0.0007 mol) and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 8.1 g (yield 53.7%) of <Intermediate 90-1>.

(2) Manufacturing example 2: Synthesis of intermediate 90-2

Intermediate 90-1 (10.0 g, 0.023 mol), 2-Biphenylboronic acid (5.5 g, 0.028 mol), K ₂ CO ₃ (9.6 g, 0.069 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.0005 mol) 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 7.8 g (yield 66.7%) of <Intermediate 90-2>.

(3) Manufacturing example 3: Synthesis of intermediate 90-3

[1,1':3',1"-terphenyl]-5'-amine (10.0 g, 0.041 mol), 1-Bromo-3,5-diphenylbenzene (18.9 g, 0.061 mol), NaOtBu (11.75 g, 0.122 mol), Pd(dba) ₂ (0.9 g, 1.6 mmol), and t-Bu ₃ P (0.7 g, 3.3 mmol) were mixed with 150 mL of Xylene and stirred at 70°C for 4 hours to react. After completion of reaction, extraction After concentration, column and recrystallization were performed to obtain 12.1 g of <Intermediate 90-3> (yield 62.7%).

(4) Manufacturing example 4: Synthesis of Compound 90

Intermediate 90-2 (10.0 g, 0.020 mol), Intermediate 90-3 (14.0 g, 0.030 mol), NaOtBu (5.7 g, 0.059 mol), Pd(dba) ₂ (0.5 g, 0.8 mmol), t-Bu ₃ 150 mL of Xylene was added to P (0.3 g, 1.6 mmol) and stirred at 120°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and recrystallized with a column to obtain 12.7 g of <Compound 90> (yield 68.1%).

LC/MS: m/z=942[(M) ⁺ ]

Synthesis example 5: Synthesis of Compound 125

(One) Manufacturing example 1: Synthesis of intermediate 125-1

1-Chloro-2-bromobenzene-3,4,5,6-D4 (10.0 g, 0.051 mol), Phenyl-D5-boronic acid (7.8 g, 0.061 mol), K ₂ CO ₃ (21.2 g, 0.154 mol) , 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added to Pd(PPh ₃ ) ₄ (1.2 g, 0.001 mol) and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 6.2 g (yield 61.3%) of <Intermediate 125-1>.

(2) Manufacturing example 2: Synthesis of intermediate 125-2

Intermediate 125-1 (10.0 g, 0.051 mol), Bis(pinacolato)diboron (15.4 g, 0.061 mol), CH ₃ COOK (14.9 g, 0.152 mol), Pd(dppf)Cl ₂ (1.9 g, 2.5 mmol), Dioxane was added to XPhos (2.2 g, 4.6 mmol) and stirred at 100°C for 12 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 10.5 g of <Intermediate 125-2> (yield 71.8%).

(3) Manufacturing example 3: Synthesis of intermediate 125-3

Intermediate 90-1 (10.0 g, 0.023 mol), intermediate 125-2 (8.0 g, 0.028 mol), K ₂ CO ₃ (9.6 g, 0.070 mol), Pd(PPh ₃ ) ₄ (0.5 g, 5 mmol) 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 7.6 g of <Intermediate 125-3> (yield 65.5%).

(4) Manufacturing example 4: Synthesis of Compound 125

Intermediate 125-3 (10.0 g, 0.019 mol), Bis(4-biphenylyl)amine (9.4 g, 0.029 mol), NaOtBu (5.6 g, 0.058 mol), Pd(dba) ₂ (0.5 g, 0.8 mmol), t 150 mL of Xylene was added to -Bu ₃ P (0.3 g, 1.6 mmol) and stirred at 120°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 10.9 g of <Compound 125> (yield 70.2%).

LC/MS: m/z=799[(M) ⁺ ]

Synthesis example 6: Synthesis of Compound 143

(One) Manufacturing example 1: Synthesis of intermediate 143-1

Intermediate 90-1 (10.0 g, 0.023 mol), 3-Biphenylboronic acid (5.5 g, 0.028 mol), K ₂ CO ₃ (9.6 g, 0.069 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.5 mmol) 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 7.4 g of <Intermediate 143-1> (yield 63.3%).

(2) Manufacturing example 2: Synthesis of Compound 143

Intermediate 143-1 (10.0 g, 0.020 mol), N-(biphenyl-4-yl)-9,9-diphenyl-9H-fluoren-2-amine (9.5 g, 0.030 mol), NaOtBu (5.7 g, 0.059 mol) ), Pd(dba) ₂ (0.5 g, 0.8 mmol), and t-Bu ₃ P (0.3 g, 1.6 mmol) were added to 150 mL of Xylene and stirred at 120°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 12.6 g of <Compound 143> (yield 66.7%).

LC/MS: m/z=954 [(M) ⁺ ]

Synthesis example 7: Synthesis of Compound 178

(One) Manufacturing example 1: Synthesis of intermediate 178-1

Intermediate 90-1 (10.0 g, 0.023 mol), 4-Biphenylboronic acid (5.5 g, 0.028 mol), K ₂ CO ₃ (9.6 g, 0.069 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.5 mmol) 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, it was extracted, concentrated, and recrystallized with a column to obtain 7.3 g of <Intermediate 178-1> (yield 62.4%).

(2) Manufacturing example 2: Synthesis of Compound 178

Intermediate 178-1 (10.0 g, 0.020 mol), N-[1,1'-Biphenyl]-4-yl[1,1':2',1"-terphenyl]-4'-amine (10.4 g, 0.030 mol), NaOtBu (5.7 g, 0.059 mol), Pd(dba) ₂ (0.5 g, 0.8 mmol), t-Bu ₃ P (0.3 g, 1.6 mmol), add 150 mL of After the reaction was completed, the extract was extracted, concentrated, and recrystallized with a column to obtain 11.4 g of <Compound 178> (yield 66.5%).

LC/MS: m/z=866[(M) ⁺ ]

Synthesis example 8: Synthesis of Compound 210

(One) Manufacturing example 1: Synthesis of Compound 210

Intermediate 178-1 (10.0 g, 0.020 mol), N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]thiophen-4-amine (10.4 g, 0.030 mol), NaOtBu (5.7 g, 0.059 mol), Pd(dba) ₂ (0.5 g, 0.8 mmol), and t-Bu ₃ P (0.3 g, 1.6 mmol) were mixed with 150 mL of xylene and stirred at 120°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 10.9 g of <Compound 210> (yield 67.2%).

LC/MS: m/z=820[(M) ⁺ ]

Synthesis example 9: Synthesis of Compound 231

(One) Manufacturing example 1: Synthesis of intermediate 231-1

Intermediate 90-1 (10.0 g, 0.023 mol), [1,1':3',1"-Terphenyl]-4'-ylboronic acid (7.6 g, 0.028 mol), K ₂ CO ₃ (9.6 g, 069 mol) ), Pd(PPh ₃ ) ₄ (0.5 g, 0.5 mmol) was mixed with 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, and stirred at 80°C for 6 hours to react. After the reaction was completed, the mixture was extracted and concentrated. By column and recrystallization, 8.5 g (yield 63.2%) of <Intermediate 231-1> was obtained.

(2) Manufacturing example 2: Synthesis of Compound 231

Intermediate 231-1 (10.0 g, 0.017 mol), N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (9.3 g, 0.026 mol), NaOtBu (5.0 g, 0.052 mol) ), Pd(dba) ₂ (0.4 g, 0.7 mmol), and t-Bu ₃ P (0.3 g, 1.4 mmol) were added to 150 mL of Xylene and stirred at 120°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 11.3 g of <Compound 231> (yield 72.5%).

LC/MS: m/z=906[(M) ⁺ ]

Synthesis example 10: Synthesis of compound 247

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

4-Aminobiphenyl (10.0 g, 0.059 mol), 4-Bromo-6-phenyldibenzofuran (28.7 g, 0.087 mol), NaOtBu (17.0 g, 0.177 mol), Pd(dba) ₂ (1.4 g, 2.4 mmol), t- 150 mL of Xylene was added to Bu ₃ P (1.0 g, 4.7 mmol) and stirred at 70°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 14.5 g of <Intermediate 247-1> (yield 59.6%).

(2) Manufacturing example 2: Synthesis of Compound 247

Intermediate 231-1 (10.0 g, 0.017 mol), Intermediate 247-1 (10.6 g, 0.026 mol), NaOtBu (5.0 g, 0.052 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t-Bu ₃ 150 mL of Xylene was added to P (0.3 g, 1.4 mmol) and stirred at 120°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 11.8 g of <Compound 247> (yield 71.8%).

LC/MS: m/z=956[(M) ⁺ ]

Synthesis example 11: Synthesis of Compound 284

(One) Manufacturing example 1: Synthesis of intermediate 284-1

Intermediate 90-1 (10.0 g, 0.023 mol), [1,1':3',1"-terphenyl]-5'-ylboronic acid (7.6 g, 0.028 mol), K ₂ CO ₃ (9.6 g, 0.069 mol) ), Pd(PPh ₃ ) ₄ (0.5 g, 0.5 mmol) was mixed with 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, and stirred at 80°C for 6 hours to react. After the reaction was completed, the mixture was extracted and concentrated. By column, 8.4 g (yield 62.4%) of <Intermediate 284-1> was obtained.

(2) Manufacturing example 2: Synthesis of intermediate 284-2

4-bromo-9-phenyl-9H-carbazole (10.0 g, 0.031 mol), 4-Aminobiphenyl (7.9 g, 0.047 mol), NaOtBu (9.0 g, 0.093 mol), Pd(dba) ₂ (0.7 g, 1.2 mmol) ), 150 mL of Xylene was added to t-Bu ₃ P (0.5 g, 2.5 mmol) and stirred at 70°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 9.1 g of <Intermediate 284-2> (yield 71.4%).

(3) Manufacturing example 3: Synthesis of Compound 284

Intermediate 284-1 (10.0 g, 0.017 mol), Intermediate 284-2 (10.6 g, 0.026 mol), NaOtBu (5.0 g, 0.052 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t-Bu ₃ 150 mL of Xylene was added to P (0.3 g, 1.4 mmol) and stirred at 120°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 12.1 g of <Compound 284> (yield 73.6%).

LC/MS: m/z=955[(M) ⁺ ]

Synthesis example 12: Synthesis of Compound 308

(One) Manufacturing example 1: Synthesis of intermediate 308-1

Intermediate 90-1 (10.0 g, 0.023 mol), [1,1':2',1"-terphenyl]-4'-ylboronic acid (7.6 g, 0.028 mol), K ₂ CO ₃ (9.6 g, 0.069 mol) ), Pd(PPh ₃ ) ₄ (0.5 g, 0.5 mmol) was mixed with 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, and stirred at 80°C for 6 hours to react. After the reaction was completed, the mixture was extracted and concentrated. By column, 8.5 g (yield 63.2%) of <Intermediate 308-1> was obtained.

(2) Manufacturing example 2: Synthesis of intermediate 308-2

2-Aminobiphenyl (10.0 g, 0.059 mol), 4-bromo-9,9'-spirobi[fluorene] (35.0 g, 0.089 mol), NaOtBu (17.0 g, 0.178 mol), Pd(dba) ₂ (1.4 g, 2.4 mmol), 150 mL of Xylene was added to t-Bu ₃ P (1.0 g, 4.7 mmol) and stirred at 70°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and recrystallized with a column to obtain 17.3 g of <Intermediate 308-2> (yield 60.5%).

(3) Manufacturing example 3: Synthesis of Compound 308

Intermediate 308-1 (10.0 g, 0.017 mol), Intermediate 308-2 (12.5 g, 0.026 mol), NaOtBu (5.0 g, 0.052 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t-Bu ₃ 150 mL of Xylene was added to P (0.3 g, 1.4 mmol) and stirred at 70°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 12.6 g of <Compound 308> (yield 71.3%).

LC/MS: m/z=1029[(M) ⁺ ]

Synthesis example 13: Synthesis of Compound 342

(One) Manufacturing example 1: Synthesis of intermediate 342-1

Intermediate 90-1 (10.0 g, 0.023 mol), (9,9-dimethyl-9H-fluoren-2-yl)boronic acid (6.6 g, 0.028 mol), K ₂ CO ₃ (9.6 g, 0.069 mol), Pd (PPh ₃ ) ₄ (0.5 g, 0.5 mmol) was added with 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, and stirred at 80°C for 6 hours to react. After completion of the reaction, it was extracted, concentrated, and recrystallized with a column to obtain 8.1 g of <Intermediate 342-1> (yield 64.2%).

(2) Manufacturing example 2: Synthesis of Compound 342

Intermediate 342-1 (10.0 g, 0.018 mol), N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (9.9 g, 0.028 mol), NaOtBu (5.3 g, 0.055 mol) ), Pd(dba) ₂ (0.4 g, 0.7 mmol), and t-Bu ₃ P (0.3 g, 1.5 mmol) were added to 150 mL of Xylene and stirred at 120°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 11.7 g of <Compound 342> (yield 73.4%).

LC/MS: m/z=870[(M) ⁺ ]

Synthesis example 14: Synthesis of Compound 373

(One) Manufacturing example 1: Synthesis of intermediate 373-1

Intermediate 90-1 (10.0 g, 0.023 mol), B-(9,9-diphenyl-9H-fluoren-3-yl)boronic acid (10.0 g, 0.028 mol), K ₂ CO ₃ (9.6 g, 0.069 mol) , 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added to Pd(PPh ₃ ) ₄ (0.5 g, 0.5 mmol) and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 9.9 g of <Intermediate 373-1> (yield 63.9%).

(2) Manufacturing example 2: Synthesis of Compound 373

Intermediate 373-1 (10.0 g, 0.015 mol), N-[1,1'-Biphenyl]-2-yl[1,1'-biphenyl]-2-amine (7.2 g, 0.022 mol), NaOtBu (4.3 g , 0.045 mol), Pd(dba) ₂ (0.3 g, 0.6 mmol), and t-Bu ₃ P (0.2 g, 1.2 mmol) were mixed with 150 mL of xylene and stirred at 120°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and recrystallized using a column to obtain 10.0 g of <Compound 373> (yield 70.2%).

LC/MS: m/z=954[(M) ⁺ ]

Synthesis example 15: Synthesis of compound 383

(One) Manufacturing example 1: Synthesis of intermediate 383-1

Intermediate 90-1 (10.0 g, 0.023 mol), 9,9'-spirobi[fluorene]-2-ylboronic acid (10.0 g, 0.028 mol), K ₂ CO ₃ (9.6 g, 0.069 mol), Pd(PPh ₃ ) 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added to ₄ (0.5 g, 0.5 mmol) and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and recrystallized using a column to obtain 10.3 g of <Intermediate 383-1> (yield 66.7%).

(2) Manufacturing example 2: Synthesis of Compound 383

Intermediate 383-1 (10.0 g, 0.015 mol), diphenylamine (3.8 g, 0.022 mol), NaOtBu (4.3 g, 0.045 mol), Pd(dba) ₂ (0.3 g, 0.6 mmol), t-Bu ₃ P (0.2 g, 1.2 mmol) was added to 150 mL of xylene and stirred at 120°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 8.6 g of <Compound 383> (yield 71.8%).

LC/MS: m/z=800[(M) ⁺ ]

Synthesis example 16: Synthesis of Compound 422

(One) Manufacturing example 1: Synthesis of intermediate 422-1

Intermediate 90-1 (10.0 g, 0.023 mol), 4-dibenzofuranboronic acid (5.9 g, 0.028 mol), K ₂ CO ₃ (9.6 g, 0.069 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.5 mmol) 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added and stirred at 80°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 7.8 g of <Intermediate 422-1> (yield 64.9%).

(2) Manufacturing example 2: Synthesis of Compound 422

Intermediate 422-1 (10.0 g, 0.019 mol), N-[1,1'-biphenyl]-2-yl-9,9-dimethyl-9H-Fluoren-4-amine (10.4 g, 0.029 mol), NaOtBu ( 5.5 g, 0.058 mol), Pd(dba) ₂ (0.4 g, 0.8 mmol), and t-Bu ₃ P (0.3 g, 1.5 mmol) were mixed with 150 mL of After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 11.5 g of <Compound 422> (yield 70.7%).

LC/MS: m/z=844[(M) ⁺ ]

device Example ( EBL )

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 using an ITO glass substrate to which the ITO transparent electrode is attached on a glass substrate of 25 mm × 25 mm × 0.7 mm. and then washed. After the substrate was mounted in a vacuum chamber and the base pressure was set to 1 × 10 ^-6 torr, organic materials and metals were deposited on the ITO in the following structure.

device Example 1 to 45

The compound implemented according to the present invention was employed in the electron blocking layer to manufacture an organic light-emitting device having the following device structure, and then the 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 (HT1, 100 nm) / electron blocking layer (10 nm) / emitting layer (20 nm) / electron transport layer (ET1:Liq, 30 nm) / LiF ( 1 nm) / Al (100 nm)

[HAT-CN] was deposited to a thickness of 5 nm on the top of the ITO transparent electrode to form a hole injection layer, and then [HT1] was deposited to a thickness of 100 nm to form a hole transport layer. Afterwards, the compound according to the present invention shown in [Table 1] below was deposited to a thickness of 10 nm to form an electron blocking layer, and the light emitting layer was formed at a thickness of 20 nm using [BH1] as the host compound and [BD1] as the dopant compound. It was formed by vapor deposition. Afterwards, 30 nm of an electron transport layer (50% doped with [ET1] compound Liq below) was deposited, and then LiF was deposited to a thickness of 1 nm to form an electron injection layer. Afterwards, an organic light-emitting device was manufactured by forming an Al film to a thickness of 100 nm.

device Comparative example One

The organic light-emitting device for Comparative Device Example 1 was manufactured in the same manner as the device structures of Examples 1 to 45, except that [EB1] below was used instead of the compound according to the present invention in the electron blocking layer.

device Comparative example 2

The organic light emitting device for Comparative Device Example 2 was manufactured in the same manner as the device structures of Examples 1 to 45, except that [EB2] below was used instead of the compound according to the present invention in the electron blocking layer.

device Comparative example 3

The organic light-emitting device for Comparative Device Example 3 was manufactured in the same manner as the device structures of Examples 1 to 45, except that [EB3] below was used in the electron blocking layer instead of the compound according to the present invention.

device Comparative example 4

The organic light-emitting device for Comparative Device Example 4 was manufactured in the same manner as the device structures of Examples 1 to 45, except that [EB4] below was used in the electron blocking layer instead of the compound according to the present invention.

Experiment example 1: element Example Luminous properties from 1 to 45

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

Example electronic low layer V cd/A CIEx CIey One Formula 6 4.42 7.21 0.1330 0.1363 2 Formula 13 4.29 6.93 0.1324 0.1376 3 Formula 23 4.38 6.84 0.1338 0.1345 4 Formula 27 4.26 7.07 0.1328 0.1375 5 Formula 32 4.44 6.82 0.1335 0.1362 6 Formula 39 4.31 6.97 0.1348 0.1359 7 Formula 41 4.48 6.89 0.1354 0.1346 8 Formula 44 4.33 7.04 0.1343 0.1355 9 Formula 59 4.30 6.98 0.1344 0.1367 10 Formula 64 4.39 7.30 0.1342 0.1358 11 Formula 73 4.42 7.21 0.1330 0.1363 12 Formula 81 4.28 7.08 0.1342 0.1368 13 Formula 83 4.40 7.12 0.1352 0.1349 14 Formula 90 4.46 6.89 0.1340 0.1362 15 Formula 95 4.47 7.09 0.1340 0.1362 16 Formula 106 4.35 6.94 0.1329 0.1357 17 Formula 109 4.42 7.18 0.1314 0.1384 18 Formula 115 4.25 7.23 0.1343 0.1357 19 Formula 117 4.39 6.91 0.1352 0.1348 20 Formula 125 4.44 6.79 0.1326 0.1371 21 Formula 134 4.35 7.16 0.1351 0.1349 22 Formula 143 4.43 7.09 0.1314 0.1384 23 Formula 159 4.28 7.22 0.1328 0.1375 24 Formula 169 4.35 7.16 0.1351 0.1349 25 Formula 178 4.21 7.07 0.1332 0.1366 26 Formula 197 4.40 7.02 0.1340 0.1363 27 Formula 210 4.34 6.87 0.1345 0.1354 28 Formula 231 4.23 7.25 0.1334 0.1367 29 Formula 247 4.27 7.18 0.1358 0.1342 30 Formula 263 4.38 7.21 0.1343 0.1356 31 Formula 277 4.55 7.25 0.1358 0.1341 32 Formula 284 4.43 7.56 0.1353 0.1348 33 Formula 293 4.31 6.91 0.1324 0.1375 34 Chemical formula 308 4.36 7.06 0.1352 0.1346 35 Formula 321 4.43 6.88 0.1339 0.1364 36 Formula 330 4.35 7.04 0.1351 0.1352 37 Formula 342 4.21 7.05 0.1353 0.1346 38 Formula 348 4.37 6.93 0.1318 0.1381 39 Formula 362 4.28 7.02 0.1316 0.1385 40 Formula 373 4.39 6.85 0.1323 0.1372 41 Formula 383 4.26 7.04 0.1321 0.1378 42 Formula 398 4.15 7.23 0.1310 0.1386 43 Chemical formula 409 4.18 6.74 0.1302 0.1392 44 Formula 422 4.25 6.69 0.1333 0.1369 45 Formula 426 4.19 6.82 0.1328 0.1371 Comparative Example 1 EB1 4.67 6.65 0.1353 0.1517 Comparative Example 2 EB2 4.61 6.58 0.1320 0.1390 Comparative Example 3 EB3 4.59 6.61 0.1329 0.1376 Comparative Example 4 EB4 4.65 6.56 0.1347 0.1358

Looking at the results shown in [Table 1], when the compound according to the present invention is employed in the electron blocking layer in an organic light-emitting device, the characteristic structure of the compound according to the present invention as a compound used as a conventional electron blocking layer material is compared. It can be seen that the luminous properties such as low-voltage driving characteristics, luminous efficiency, and quantum efficiency are significantly superior to those of devices employing the compound (Comparative Examples 1 to 4).

[HAT-CN] [HT1] [BH1] [BD1] [ET1]

[EB1] [EB2] [EB3] [EB4]

Claims (10)

Organic compounds represented by the following [Chemical Formula I]:
[Formula Ⅰ]

In the above [Chemical Formula I],
Ar ₁ to Ar ₃ are the same 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 3 to 30 carbon atoms,
R _A is any one selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted fluorine, and substituted or unsubstituted dibenzofuran,
R ₁ to R ₃ is the same or different from each other and is hydrogen or deuterium, respectively,
D is deuterium, n means the number of hydrogens in [Chemical Formula I] replaced with deuterium (D), and n is an integer from 0 to 60. According to paragraph 1,
The R _A is an organic compound selected from the following [Structural Formula 1] to [Structural Formula 6]:
[Structural Formula 1] [Structural Formula 2] [Structural Formula 3]

[Structural Formula 4] [Structural Formula 5] [Structural Formula 6]

Among the [Structural Formula 1] to [Structural Formula 6],
X is O or CR ₄ R ₅ ,
R ₄ and R ₅ are each independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and R ₄ and R ₅ can be connected to each other to form a ring,
Each R is independently selected from hydrogen, deuterium, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and each of the plurality of R in each structural formula is the same or different from each other,
n is an integer from 0 to 5, m is an integer from 0 to 7, o is an integer from 0 to 4, and p is an integer from 0 to 3. According to claim 1 or 2,
In the definition of Ar ₁ to Ar ₃ , R _A , R, R ₄ and R ₅ , substituted or unsubstituted means that Ar ₁ to Ar ₃ , R _A , R, R ₄ and R ₅ are respectively deuterium, cyano group, Substituted with one or two or more substituents selected from halogen group, hydroxy group, nitro group, alkyl group, alkoxy group, halogenated alkoxy group, cycloalkyl group, heterocycloalkyl group, aryl group, fluorenyl group, heteroaryl group, silyl group and amine group. Or, an organic compound meaning that two or more of the above substituents are substituted with a linked substituent, or that it does not have any substituents. According to paragraph 1,
[Formula I] is an organic compound characterized in that the hydrogen present in [Formula I] is partially substituted with deuterium (D), and the deuterium (D) substitution rate is 10 to 90%. According to paragraph 4,
An organic compound characterized in that the deuterium (D) substitution rate is 20 to 80%. According to clause 5,
An organic compound characterized in that the deuterium (D) substitution rate is 30 to 70%. According to paragraph 1,
[Formula I] is an organic compound selected from the following [Formula 1] to [Formula 434]:





































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,
An organic light-emitting device, wherein at least one of the organic layers includes at least one organic compound represented by [Chemical Formula I] according to claim 1. According to clause 8,
The organic layer includes one or more of an electron injection layer, an electron transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, and a light emitting layer,
An organic light-emitting device, wherein at least one of the layers includes an organic compound represented by the formula (I). According to clause 9,
An organic light-emitting device comprising an organic compound represented by [Chemical Formula I] in the electron blocking layer.