KR20230149244A - 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], which has excellent hole injection and transport performance, high triplet exciton confinement performance, excellent electron blocking performance, and excellent stability in a thin film state, When used as an organic layer in an organic light emitting device, preferably an electron blocking layer or a hole transport layer, it is possible to implement an organic light emitting device with excellent light emitting properties such as luminous efficiency and quantum efficiency.
[Formula Ⅰ]

Description

Organic compound and electroluminescent device comprising the same}

The present invention relates to organic compounds, and more specifically, organic compounds used in organic layers such as electron blocking layers and hole transport layers in organic light-emitting devices, and organic compounds whose device characteristics, such as low-voltage driving, long life, and luminous efficiency, are significantly improved by employing them. It is about light emitting devices.

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.

In an organic light emitting device, electrons injected from an electron injection electrode (cathode electrode) and holes injected from a hole injection electrode (anode electrode) combine in the light emitting layer to form an exciton, and the exciton produces energy. It is a self-luminous device that emits light while emitting light, and such organic light-emitting devices are attracting attention as next-generation light sources due to the advantages of low driving voltage, high luminance, wide viewing angle, fast response speed, and applicability to full-color flat panel light-emitting displays. .

However, in order for these organic light-emitting devices to exhibit the above characteristics, the structure of the organic layer within the device must be optimized, and the materials that make up each organic layer: hole injection material, hole transport material, hole blocking material, light-emitting material, electron transport material, and electron. Although injection materials, electron blocking materials, etc. must be supported by stable and efficient materials, there is still a need for the development of stable and efficient organic layer structures and materials for organic light-emitting 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 provides an organic compound that can be used as an organic layer material such as an electron blocking layer and a hole transport 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. We would like to provide.

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 containing the same.

[Formula Ⅰ]

The specific structure of [Chemical Formula I], the specific compounds implemented thereby, and the definitions of R ₁ , Ar ₁ to Ar ₃ , l, m, 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 an organic compound represented by the following [Chemical Formula I], which has device characteristics such as low voltage driving, long life, and luminous efficiency when employed in various organic layers in an organic light-emitting device, preferably in an electron blocking layer and a hole transport layer. It is possible to implement this significantly improved organic light emitting device.

[Formula Ⅰ]

In the above [Chemical Formula I],

Ar ₁ is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted fluorenyl group, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

Ar ₂ is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted fluorenyl group.

Ar ₃ is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

R ₁ is hydrogen or deuterium.

l is an integer from 1 to 4, and m is an integer from 2 to 5. When l and m are each 2 or more, a plurality of Ar ₃ and R ₁ are the same or different from each other.

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.

[Formula I] may be a compound in which not only the skeletal structure, but also R ₁ introduced thereto may be deuterium, and each of Ar ₁ to Ar ₃ is partially substituted with deuterium (D), that is, Ar ₁ to Ar ₃ are each It may include at least one deuterium as a substituent.

According to one embodiment of the present invention, the deuterium (D) substitution rate may be 10 to 90%.

In this way, the compound according to the present invention replaces some of the hydrogen in the structure of [Formula I] with deuterium, making it possible to implement an organic light-emitting device with a longer lifespan by compensating for the shortcomings of the low lifespan of organic light-emitting devices found according to the conventional moiety structure. do.

According to one embodiment of the present invention, the [Chemical Formula I] may be expressed as the following [Chemical Formula I-1].

[Formula Ⅰ-1]

In the above [Formula Ⅰ-1],

Ar ₁ is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted fluorenyl group, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

Ar ₂ is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted fluorenyl group.

R ₁ is hydrogen or deuterium.

l is an integer from 1 to 4, and when l is 2 or more, a plurality of R ₁ is the same or different from each other,

Ar ₄ corresponds to the phenyl structure in which Ar ₃ is substituted in the above [Chemical Formula I], and is characterized by being represented by 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],

R ₂ to R ₄ are the same as or different from each other, and each independently represents hydrogen, deuterium, or an aryl group having 6 to 30 carbon atoms.

o is an integer from 0 to 3, p and q are each an integer from 0 to 5, and when o, p and q are 2 or more, R ₂ to R ₄ are the same or different from each other.

D is deuterium, n means the number of hydrogens in [Chemical Formula I-1] replaced with deuterium (D), and n is an integer from 0 to 60.

[Formula I-1] includes not only a skeletal structure, but also R ₁ introduced therein may be deuterium, and at least one of R ₂ , R ₃ and R ₄ may each be deuterium, and Ar ₁ and Compounds in which Ar ₂ is each partially substituted with deuterium (D), that is, Ar ₁ and Ar ₂ may each include at least one deuterium as a substituent.

According to one embodiment of the present invention, the deuterium (D) substitution rate may be 10 to 90%.

As such, the compound according to the present invention replaces some of the hydrogen in the structure of [Chemical Formula I-1] with deuterium, thereby making up for the shortcomings of the low lifespan of organic light-emitting devices identified according to the conventional moiety structure, thereby producing an organic light-emitting device with a longer lifespan. Make implementation possible.

Meanwhile, in the definition of Ar ₁ to Ar ₃ in [Formula I] and [Formula I-1], substituted or unsubstituted means that Ar ₁ to Ar ₃ are respectively deuterium, cyano group, halogen group, hydroxy group, and 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, or two or more of the above substituents. It means that the substituent is substituted with a linked substituent 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 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 or alkoxy group may be a deuterated alkyl group or alkoxy group, a halogenated alkyl group, or an alkoxy group, which means an alkyl group or alkoxy group in which the alkyl group or alkoxy group is 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.

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 linked 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, hole transport 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, the conditions required for each organic layer such as a hole transport layer and an electron blocking layer can be met. Organic compound materials that satisfy the requirements can be manufactured, and in particular, when the compound of [Chemical Formula I] according to the present invention is used for the electron blocking layer, hole transport 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.

Therefore, in the organic light emitting device according to the present invention, the organic layer may include a hole transport layer or an electron blocking layer, 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 1

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

4-(4-Chlorophenyl)-9-phenyl-9H-carbazole (10.0 g, 0.028 mol), [1,1':3',1"-Terphenyl]-4'-amine (10.4 g, 0.042 mol), _{150 mL} of After completion of the reaction, the extract was extracted and concentrated, followed by column and recrystallization to obtain 10.1 g of <Intermediate 1-1> (yield 63.5%).

(2) Manufacturing example 2: Synthesis of Compound 1

Intermediate 1-1 (10.0 g, 0.018 mol), 4-Bromobiphenyl (6.2 g, 0.027 mol), NaOtBu (5.1 g, 0.053 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t-Bu ₃ P (0.3 g, 1.4 mmol) was added with 150 mL of xylene 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 9.8 g of <Compound 1> (yield 77.1%).

LC/MS: m/z=714[(M) ⁺ ]

Synthesis example 2: Synthesis of Compound 8

(One) Manufacturing example 1: Synthesis of Compound 8

Intermediate 1-1 (10.0 g, 0.018 mol), 4-Bromo-p-terphenyl (8.2 g, 0.027 mol), NaOtBu (5.1 g, 0.053 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t 150 mL of Xylene was added to -Bu ₃ 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 10.5 g of <Compound 8> (yield 74.7%).

LC/MS: m/z=791[(M) ⁺ ]

Synthesis example 3: Synthesis of Compound 11

(One) Manufacturing example 1: Synthesis of intermediate 11-1

3-Bromo-5-iodo-1,1'-biphenyl (10.0 g, 0.028 mol), [1,1':3',1"-terphenyl]-5'-ylboronic acid (9.2 g, 0.033 mol), Add 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O to K ₂ CO ₃ (11.6 g, 0.084 mol) and Pd(PPh ₃ ) ₄ (0.6 g, 0.0006 mol) and stir at 80°C for 6 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 6.7 g of <Intermediate 11-1> (yield 52.1%).

(2) Manufacturing example 2: Synthesis of Compound 11

Intermediate 1-1 (10.0 g, 0.018 mol), Intermediate 11-1 (12.3 g, 0.027 mol), NaOtBu (5.1 g, 0.053 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 11.1 g of <Compound 11> (yield 66.2%).

LC/MS: m/z=943[(M) ⁺ ]

Synthesis example 4: Synthesis of compound 25

(One) Manufacturing example 1: Synthesis of Compound 25

Intermediate 1-1 (10.0 g, 0.018 mol), 2-Bromo-9,9-dimethylfluorene (7.3 g, 0.027 mol), NaOtBu (5.1 g, 0.053 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol) , 150 mL of Xylene was added to t-Bu ₃ 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 12.4 g of <Compound 25> (yield 64.6%).

LC/MS: m/z=754[(M) ⁺ ]

Synthesis example 5: Synthesis of Compound 31

(One) Manufacturing example 1: Synthesis of Compound 31

Intermediate 1-1 (10.0 g, 0.018 mol), 2-Bromo-9,9'-spirobi[9H-fluorene] (10.5 g, 0.027 mol), NaOtBu (5.1 g, 0.053 mol), Pd(dba) ₂ ( 0.4 g, 0.7 mmol) and t-Bu ₃ P (0.3 g, 1.4 mmol) were added with 150 mL of Xylene 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 10.7 g of <Compound 31> (yield 68.7%).

LC/MS: m/z=877[(M) ⁺ ]

Synthesis example 6: Synthesis of Compound 43

(One) Manufacturing example 1: Synthesis of intermediate 43-1

9-phenyl-9H-carbazol-4-yl-4-boronic acid (10.0 g, 0.035 mol), 4-Bromochlorobenzene-2,3,5,6-d4 (8.2 g, 0.042 mol), K ₂ CO ₃ ( 14.4 g, 0.105 mol), Pd(PPh ₃ ) ₄ (0.8 g, 0.0007 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 62.6%) of <Intermediate 43-1>.

(2) Manufacturing example 2: Synthesis of intermediate 43-2

Intermediate 43-1 (10.0 g, 0.028 mol), [1,1':3',1"-Terphenyl]-4'-amine (10.3 g, 0.042 mol), NaOtBu (8.1 g, 0.084 mol), Pd( dba) ₂ (0.6 g, 1.1 mmol) and t-Bu ₃ P (0.5 g, 2.2 mmol) were mixed with 150 mL of and recrystallized to obtain 5.4 g (59.4% yield) of <Intermediate 43-2>.

(3) Manufacturing example 3: Synthesis of Compound 43

Intermediate 43-2 (10.0 g, 0.018 mol), 4-Bromobiphenyl (6.2 g, 0.027 mol), NaOtBu (5.1 g, 0.053 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t-Bu ₃ P (0.3 g, 1.4 mmol) was added with 150 mL of xylene and stirred at 70°C for 4 hours to react. After completion of the reaction, the extract was extracted, concentrated, and recrystallized using a column to obtain 8.7 g of <Compound 43> (yield 68.6%).

LC/MS: m/z=718[(M) ⁺ ]

Synthesis example 7: Synthesis of Compound 62

(One) Manufacturing example 1: Synthesis of intermediate 62-1

4-(4-Chlorophenyl)-9-phenyl-9H-carbazole (10.0 g, 0.028 mol), [1,1':3',1"-terphenyl]-5'-amine (10.4 g, 0.042 mol), _{150 mL} of After completion of the reaction, the extract was extracted, concentrated, and recrystallized using a column to obtain 8.5 g of <Intermediate 62-1> (yield 53.5%).

(2) Manufacturing example 2: Synthesis of Compound 62

Intermediate 62-1 (10.0 g, 0.018 mol), 4-Bromobiphenyl (6.2 g, 0.027 mol), NaOtBu (5.1 g, 0.053 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t-Bu ₃ P (0.3 g, 1.4 mmol) was added with 150 mL of xylene 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 <Compound 62> (yield 71.6%).

LC/MS: m/z=714[(M) ⁺ ]

Synthesis example 8: Synthesis of compound 68

(One) Manufacturing example 1: Synthesis of Compound 68

Intermediate 62-1 (10.0 g, 0.018 mol), 5'-Bromo-1,1':3',1"-terphenyl (8.2 g, 0.027 mol), NaOtBu (3.4 g, 0.036 mol), Pd(dba) ₂ (0.5 g, 0.9 mmol) and t-Bu ₃ P (0.4 g, 1.8 mmol) were added with 150 mL of 10.1 g (yield 71.9%) of <Compound 68> was obtained.

LC/MS: m/z=790[(M) ⁺ ]

Synthesis example 9: Synthesis of Compound 72

(One) Manufacturing example 1: Synthesis of Compound 72

Intermediate 62-1 (10.0 g, 0.018 mol), 1-bromo-4-(2-phenylphenyl)benzene (8.2 g, 0.027 mol), NaOtBu (5.1 g, 0.053 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), 150 mL of xylene was added to t-Bu ₃ 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 10.4 g of <Compound 72> (yield 74.0%).

LC/MS: m/z=791[(M) ⁺ ]

Synthesis example 10: Synthesis of Compound 96

(One) Manufacturing example 1: Synthesis of Compound 96

Intermediate 62-1 (10.0 g, 0.018 mol), 4-Bromo-9,9'-spirobi[9H-fluorene] (10.5 g, 0.027 mol), NaOtBu (5.1 g, 0.053 mol), Pd(dba) ₂ ( 0.4 g, 0.7 mmol) and t-Bu ₃ P (0.3 g, 1.4 mmol) were added with 150 mL of Xylene 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 9.7 g of <Compound 96> (yield 62.2%).

LC/MS: m/z=877[(M) ⁺ ]

Synthesis example 11: Synthesis of compound 107

(One) Manufacturing example 1: Synthesis of intermediate 107-1

Intermediate 43-1 (10.0 g, 0.028 mol), [1,1':3',1"-terphenyl]-5'-amine (10.3 g, 0.042 mol), NaOtBu (8.1 g, 0.084 mol), Pd( dba) ₂ (0.6 g, 1.1 mmol) and t-Bu ₃ P (0.4 g, 2.2 mmol) were mixed with 150 mL of and recrystallized to obtain 7.6 g (yield 48.0%) of <Intermediate 107-1>.

(2) Manufacturing example 2: Synthesis of Compound 107

Intermediate 107-1 (10.0 g, 0.018 mol), 4-Bromobiphenyl (6.2 g, 0.027 mol), NaOtBu (5.1 g, 0.053 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol), t-Bu ₃ P (0.3 g, 1.4 mmol) was added with 150 mL of xylene 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 9.2 g of <Compound 107> (yield 72.5%).

LC/MS: m/z=718[(M) ⁺ ]

Synthesis example 12: Synthesis of compound 117

(One) Manufacturing example 1: Synthesis of Compound 117

Intermediate 107-1 (10.0 g, 0.018 mol), 5'-Bromo-1,1':3',1"-terphenyl (8.2 g, 0.027 mol), NaOtBu (5.1 g, 0.053 mol), Pd(dba) ₂ (0.4 g, 0.7 mmol) and t-Bu ₃ P (0.3 g, 1.4 mmol) were added with 150 mL of 8.9 g (yield 63.4%) of <Compound 117> was obtained.

LC/MS: m/z=794[(M) ⁺ ]

Synthesis example 13: Synthesis of compound 131

(One) Manufacturing example 1: Synthesis of Compound 131

4-(4-Chlorophenyl)-9-phenyl-9H-carbazole (10.0 g, 0.028 mol), N-[1,1'-Biphenyl]-4-yl[1,1':2',1"-terphenyl ]-4'-amine (16.9 g, 0.042 mol), NaOtBu (8.2 g, 0.085 mol), Pd(dba) ₂ (0.7 g, 1.1 mmol), t-Bu ₃ P (0.5 g, 2.3 mmol) in Xylene 150 mL was added and stirred for 4 hours at 120° C. After the reaction was completed, extraction and concentration were performed, followed by column and recrystallization to obtain 14.2 g of <Compound 131> (yield 70.3%).

LC/MS: m/z=715[(M) ⁺ ]

Synthesis example 14: Synthesis of compound 138

(One) Manufacturing example 1: Synthesis of intermediate 138-1

Add 500ml of DMF to B-9H-Carbazol-4-ylboronic acid (10.0 g, 0.047 mol), Fluorobenzene-d5 (5.8 g, 0.057 mol), and Cs ₂ CO ₃ (9.8 g, 0.071 mol) and incubate at 150°C for 12 hours. The reaction was carried out under reflux and stirring. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 8.4 g (yield 60.7%) of <Intermediate 138-1>.

(2) Manufacturing example 2: Synthesis of intermediate 138-2

Intermediate 138-1 (10.0 g, 0.034 mol), 1-Bromo-4-chlorobenzene (7.9 g, 0.041 mol), K ₂ CO ₃ (14.2 g, 0.103 mol), Pd(PPh ₃ ) ₄ (0.8 g, 0.7 mmol), 200 mL of Toluene, 50 mL of EtOH, 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 138-2> (yield 61.9%).

(3) Manufacturing example 3: Synthesis of Compound 138

Intermediate 138-2 (10.0 g, 0.028 mol), N-[1,1'-Biphenyl]-4-yl[1,1':2',1"-terphenyl]-4'-amine (16.6 g, 0.042 mol), NaOtBu (8.0 g, 0.084 mol), Pd(dba) ₂ (0.6 g, 1.1 mmol), t-Bu ₃ P (0.5 g, 2.2 mmol), add 150 mL of After the reaction was completed, the extract was extracted, concentrated, and then recrystallized with a column to obtain 13.9 g of <Compound 138> (yield 69.3%).

LC/MS: m/z=720 [(M) ⁺ ]

Synthesis example 15: Synthesis of compound 148

(One) Manufacturing example 1: Synthesis of intermediate 148-1

2,4,6-Tribromoaniline (10.0 g, 0.030 mol), Phenylboronic acid (13.3 g, 0.109 mol), K ₂ CO ₃ (37.7 g, 0.273 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) Add 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O and stir 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 83.1%) of <Intermediate 148-1>.

(2) Manufacturing example 2: Synthesis of intermediate 148-2

4-(4-Chlorophenyl)-9-phenyl-9H-carbazole (10.0 g, 0.028 mol), intermediate 148-1 (13.6 g, 0.042 mol), NaOtBu (8.2 g, 0.085 mol), Pd(dba) ₂ ( 0.7 g, 1.1 mmol) and t-Bu ₃ P (0.5 g, 2.3 mmol) were added with 150 mL of Xylene 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 9.5 g of <Intermediate 148-2> (yield 52.6%).

(3) Manufacturing example 3: Synthesis of Compound 148

Intermediate 148-2 (10.0 g, 0.016 mol), 4-Bromobiphenyl (5.5 g, 0.024 mol), NaOtBu (4.5 g, 0.047 mol), Pd(dba) ₂ (0.4 g, 0.6 mmol), t-Bu ₃ P (0.3 g, 1.3 mmol) was added with 150 mL of xylene 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 9.2 g of <Compound 148> (yield 74.3%).

LC/MS: m/z=790[(M) ⁺ ]

Synthesis example 16: Synthesis of compound 174

(One) Manufacturing example 1: Synthesis of intermediate 174-1

3,5-Dibromoaniline (10.0 g, 0.040 mol), [1,1':3',1"-Terphenyl]-5'-ylboronic acid (26.2 g, 0.096 mol), K ₂ CO ₃ (33.1 g, 0.239 mol), Pd(PPh ₃ ) ₄ (0.9 g, 0.0008 mol) 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 the reaction was completed, the mixture was extracted and concentrated. After columnarization, 15.8 g (72.1% yield) of <Intermediate 174-1> was obtained.

(2) Manufacturing example 2: Synthesis of intermediate 174-2

4-(4-Chlorophenyl)-9-phenyl-9H-carbazole (10.0 g, 0.028 mol), intermediate 174-1 (23.3 g, 0.042 mol), NaOtBu (8.2 g, 0.085 mol), Pd(dba) ₂ ( 0.7 g, 1.1 mmol) and t-Bu ₃ P (0.5 g, 2.3 mmol) were added with 150 mL of Xylene 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 12.2 g of <Intermediate 174-2> (yield 49.8%).

(3) Manufacturing example 3: Synthesis of Compound 174

Intermediate 174-2 (10.0 g, 0.012 mol), Bromobenzene (2.7 g, 0.017 mol), NaOtBu (3.3 g, 0.035 mol), Pd(dba) ₂ (0.3 g, 0.5 mmol), t-Bu ₃ P (0.2 g, 0.9 mmol) and reacted by adding 150 mL of Xylene and stirring at 70°C for 4 hours. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 8.1 g of <Compound 174> (yield 74.5%).

LC/MS: m/z=943[(M) ⁺ ]

device Example

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 80

After manufacturing an organic light emitting device having the following device structure by employing the compound implemented according to the present invention in the electron blocking layer, the light emitted by the compound implemented according to the present invention and the organic light emitting device employing the same in the electron blocking layer and driving characteristics were measured.

ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (HT1, 100 nm) / electron blocking layer (10nm) / emission 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. According to the present invention described in [Table 1] below, The following compound was deposited to a thickness of 10 nm to form an electron blocking layer, the light emitting layer was formed by co-deposition to a thickness of 20 nm using [BH1] as the host compound and [BD1] as the dopant compound, and the electron transport layer ([ET1] below) After depositing 30 nm of compound Liq (50% doped), LiF was deposited to a thickness of 1 nm to form an electron injection layer, and Al was deposited to a thickness of 100 nm to produce an organic light emitting device.

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 80 except that [EB1] 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 Device Comparative Example 2 was manufactured in the same manner as the device structures of Examples 1 to 80, except that [EB2] 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 Device Comparative Example 3 was manufactured in the same manner as the device structures of Examples 1 to 80, except that [EB3] 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 80, except that [EB4] was used in the electron blocking layer instead of the compound according to the present invention.

device Comparative example 5

The organic light emitting device for Comparative Device Example 5 was manufactured in the same manner as the device structures of Examples 1 to 80, except that [EB5] was used instead of the compound according to the present invention in the electron blocking layer.

device Comparative example 6

The organic light emitting device for Comparative Device Example 6 was manufactured in the same manner as the device structures of Examples 1 to 80, except that [EB6] was used instead of the compound according to the present invention in the electron blocking layer.

Experiment example 1: element Example Luminous properties from 1 to 80

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 1 4.12 7.55 0.1343 0.1310 2 Formula 2 4.33 7.22 0.1327 0.1312 3 Formula 3 4.37 7.25 0.1387 0.1315 4 Formula 4 4.29 7.29 0.1358 0.1389 5 Formula 6 4.34 7.57 0.1365 0.1394 6 Formula 8 4.36 7.31 0.1353 0.1392 7 Formula 9 4.29 7.23 0.1357 0.1376 8 Formula 10 4.35 7.21 0.1335 0.1378 9 Formula 11 4.38 7.27 0.1325 0.1313 10 Formula 12 4.23 7.31 0.1334 0.1315 11 Formula 13 4.22 7.10 0.1378 0.1344 12 Formula 16 4.38 7.54 0.1384 0.1344 13 Formula 18 4.24 7.52 0.1354 0.1365 14 Formula 19 4.35 7.47 0.1353 0.1360 15 Formula 23 4.26 7.38 0.1354 0.1365 16 Formula 25 4.30 7.24 0.1361 0.1388 17 Formula 26 4.29 7.57 0.1333 0.1392 18 Formula 29 4.32 7.55 0.1344 0.1338 19 Formula 31 4.27 7.26 0.1367 0.1342 20 Formula 32 4.21 7.43 0.1385 0.1295 21 Formula 34 4.30 7.74 0.1383 0.1348 22 Formula 35 4.28 7.35 0.1341 0.1336 23 Formula 37 4.35 7.54 0.1334 0.1350 24 Formula 39 4.32 7.31 0.1358 0.1379 25 Formula 42 4.27 7.91 0.1346 0.1381 26 Formula 43 4.12 7.55 0.1343 0.1310 27 Formula 51 4.12 7.55 0.1343 0.1310 28 Formula 53 4.30 7.24 0.1361 0.1388 29 Formula 54 4.27 7.26 0.1367 0.1342 30 Formula 55 4.28 7.35 0.1341 0.1336 31 Formula 56 4.12 7.55 0.1343 0.1310 32 Formula 61 4.30 7.24 0.1361 0.1388 33 Formula 62 4.35 7.41 0.1342 0.1368 34 Formula 63 4.34 7.29 0.1397 0.1354 35 Formula 64 4.22 7.29 0.1402 0.1314 36 Formula 67 4.36 7.34 0.1398 0.1323 37 Formula 68 4.14 7.25 0.1371 0.1333 38 Formula 69 4.36 7.54 0.1397 0.1371 39 Formula 70 4.27 7.36 0.1375 0.1373 40 Formula 71 4.28 7.44 0.1379 0.1377 41 Formula 72 4.16 7.28 0.1395 0.1385 42 Formula 75 4.33 7.42 0.1363 0.1326 43 Formula 78 4.20 7.34 0.1347 0.1364 44 Formula 86 4.37 7.35 0.1318 0.1392 45 Formula 87 4.26 7.40 0.1345 0.1297 46 Formula 91 4.32 7.61 0.1345 0.1376 47 Formula 93 4.24 7.33 0.1396 0.1306 48 Formula 96 4.27 7.36 0.1369 0.1307 49 Formula 98 4.14 7.34 0.1351 0.1354 50 Formula 101 4.32 7.71 0.1373 0.1382 51 Formula 102 4.15 7.33 0.1327 0.1387 52 Formula 105 4.22 7.23 0.1351 0.1349 53 Formula 107 4.35 7.41 0.1342 0.1368 54 Formula 109 4.35 7.41 0.1342 0.1368 55 Formula 113 4.26 7.40 0.1345 0.1297 56 Formula 114 4.08 7.21 0.1333 0.1343 57 Formula 115 4.25 7.53 0.1388 0.1372 58 Formula 116 4.37 7.50 0.1332 0.1372 59 Formula 117 4.14 7.25 0.1371 0.1333 60 Formula 122 4.35 7.41 0.1342 0.1368 61 Formula 126 4.14 7.25 0.1371 0.1333 62 Formula 131 4.21 7.25 0.1387 0.1324 63 Formula 133 4.17 7.20 0.1393 0.1383 64 Formula 138 4.21 7.25 0.1387 0.1324 65 Formula 142 4.25 7.47 0.1353 0.1366 66 Formula 144 4.25 7.47 0.1353 0.1366 67 Formula 148 4.35 7.32 0.1375 0.1325 68 Formula 149 4.01 7.63 0.1352 0.1370 69 Formula 152 4.30 7.58 0.1353 0.1376 70 Formula 155 4.24 7.29 0.1355 0.1388 71 Formula 158 4.15 7.31 0.1362 0.1342 72 Formula 159 4.32 7.57 0.1353 0.1369 73 Chemical formula 160 4.08 7.24 0.1337 0.1376 74 Formula 161 4.12 7.36 0.1397 0.1311 75 Formula 163 4.19 7.21 0.1368 0.1341 76 Formula 167 4.26 7.59 0.1375 0.1324 77 Formula 169 4.25 7.33 0.1363 0.1346 78 Formula 172 4.07 7.31 0.1367 0.1343 79 Formula 174 4.23 7.29 0.1345 0.1374 80 Formula 175 4.28 7.39 0.1370 0.1352 Comparative Example 1 EB1 4.67 6.65 0.1353 0.1517 Comparative Example 2 EB2 4.51 7.02 0.1338 0.1391 Comparative Example 3 EB3 4.46 6.97 0.1347 0.1335 Comparative Example 4 EB4 4.55 7.03 0.1332 0.1375 Comparative Example 5 EB5 4.57 7.12 0.1335 0.1369 Comparative Example 6 EB6 4.63 6.95 0.1342 0.1351

Looking at the results shown in [Table 1], in the case of an organic light-emitting device employing the compound according to the present invention as an electron blocking layer in the device, the characteristic structure of the compound according to the present invention as a compound conventionally used as an electron blocking layer material 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 compounds contrasting with (Comparative Examples 1 to 6).

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

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

[EB5] [EB6]

Claims (13)

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

In the above [Chemical Formula I],
Ar ₁ is any one selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted fluorenyl group, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,
Ar ₂ is any one selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted fluorenyl group,
Ar ₃ is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
R ₁ is hydrogen or deuterium,
l is an integer from 1 to 4, m is an integer from 2 to 5, and when l and m are each 2 or more, a plurality of Ar ₃ and R ₁ are the same or different from each other,
D is deuterium, n means the number of hydrogens in [Formula I] replaced with deuterium (D), and n is an integer from 0 to 60. According to paragraph 1,
The [Formula I] is an organic compound represented by the following [Formula I-1]:
[Formula Ⅰ-1]

In the above [Formula Ⅰ-1],
Ar ₁ is any one selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted fluorenyl group, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,
Ar ₂ is any one selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted fluorenyl group,
R ₁ is hydrogen or deuterium,
l is an integer from 1 to 4, and when l is 2 or more, a plurality of R ₁ is the same or different from each other,
Ar ₄ is represented by 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],
R ₂ to R ₄ are the same as or different from each other, and are each independently hydrogen, deuterium, or an aryl group having 6 to 30 carbon atoms,
o is an integer from 0 to 3, p and q are each an integer from 0 to 5, and when o, p and q are 2 or more, R ₂ to R ₄ are the same or different from each other,
D is deuterium, n means the number of hydrogens in [Chemical Formula I-1] replaced with deuterium (D), and n is an integer from 0 to 60. According to paragraph 2,
The organic compound wherein Ar ₁ and Ar ₂ each contain at least one deuterium. According to paragraph 2,
Wherein o, p and q are each integers of 1 or more, and at least one of R ₂ , R ₃ and R ₄ is each deuterium. According to claim 1 or 2,
In the definition of Ar ₁ to Ar ₃ , substituted or unsubstituted means that Ar ₁ to Ar ₃ are respectively deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group, alkoxy group, halogenated alkoxy group, cycloalkyl group, hetero group. substituted with one or two or more substituents selected from cycloalkyl groups, aryl groups, fluorenyl groups, heteroaryl groups, silyl groups, and amine groups, or substituted with substituents in which two or more of the above substituents are linked, or without any substituents. meaning organic compounds. 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 clause 6,
An organic compound characterized in that the deuterium (D) substitution rate is 20 to 80%. According to clause 6,
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 175]:



















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 10,
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 11,
An organic light-emitting device comprising an organic compound represented by [Chemical Formula I] in the hole transport layer. According to clause 11,
An organic light-emitting device comprising an organic compound represented by [Chemical Formula I] in the electron blocking layer.