KR20240020688A - Organic compound and electroluminescent device comprising the same - Google Patents

Abstract

The present invention provides a novel organic compound represented by the following [Chemical Formula I] that can be employed as an organic layer material in an organic light-emitting device, and preferably as a light-emitting layer host material, to realize excellent light-emitting properties such as luminous efficiency and quantum efficiency of the device. and an organic light-emitting device including this in an organic layer within the device.
[Formula Ⅰ]

Description

Organic compound and electroluminescent device comprising the same}

The present invention relates to organic compounds, and more specifically, to organic compounds used as host materials for the light-emitting layer in organic light-emitting devices due to the structural characteristics of the compounds, and the use of these compounds to significantly improve device characteristics such as color purity, luminous efficiency, and quantum efficiency. It is about organic 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.

However, in order for such an organic light emitting device to exhibit the above characteristics, the materials that make up the organic layers in the device, such as a hole injection layer, hole transport layer, hole blocking layer, light emitting layer host and dopant, electron blocking layer, electron transport layer, electron injection layer, etc. This should be supported by stable and efficient materials, but the development of stable and efficient organic layer materials for organic light-emitting devices has not yet been sufficiently developed.

Therefore, in order to implement more stable organic light-emitting devices and achieve higher efficiency, longer lifespan, and enlargement of devices, additional improvements in terms of efficiency and lifespan characteristics are required. In particular, development of materials forming each organic layer of organic light-emitting devices is required. It is desperately needed.

In particular, in order to obtain maximum efficiency in the light emitting layer, the energy band gap of the host and the dopant must be appropriately combined so that holes and electrons can each move to the dopant through a stable electrochemical path to form excitons.

Therefore, the present invention seeks to provide a novel organic compound that can be employed as a host material in the light-emitting layer of an organic light-emitting device and realize excellent properties in terms of color purity, luminous efficiency, and quantum efficiency, and an organic light-emitting device containing the same.

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 characteristic structure of [Chemical Formula I], specific compounds realized thereby, and definitions of Ar ₁ to Ar ₂ , L, p, q, D (deuterium), and n will be described later.

The organic compound according to the present invention can be used as a light-emitting layer host material in an organic light-emitting device and can realize excellent device characteristics in terms of color purity, luminous efficiency, and quantum efficiency, and can be useful in various displays and lighting 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 can be employed as a light-emitting layer host in an organic light-emitting device due to its structural characteristics to realize an organic light-emitting device having excellent device characteristics in terms of color purity, luminous efficiency, and quantum efficiency. there is.

[Formula Ⅰ]

In the above [Chemical Formula I],

X is O or S.

Ar ₁ is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

L is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, p is an integer of 1 to 3, and when p is 2 or more, the plurality of L's are the same or different from each other.

Ar ₂ is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, and a substituted or unsubstituted aryl group with 6 to 20 carbon atoms. one selected from among, q is an integer of 1 to 2, and when q is 2, a plurality of Ar ₂ are the same or different from each other.

At this time, when q is 1 and Ar ₂ is defined as a substituted or unsubstituted aryl group, the aryl group is characterized in that it is a substituted or unsubstituted aryl group in which at least two or more aryl groups are connected.

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 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%.

According to one embodiment of the present invention, Ar ₁ may be a substituted or unsubstituted aryl group having 6 to 20 carbon atoms and including at least one deuterium as a substituent.

Additionally, according to one embodiment of the present invention, L may be a substituted or unsubstituted arylene group having 6 to 20 carbon atoms and including at least one deuterium as a substituent.

Meanwhile, in the definition of Ar ₁ to Ar ₂ and L, ‘substituted or unsubstituted’ means that Ar ₁ to Ar ₂ and L are each selected from deuterium, halogen group, cyano group, nitro group, hydroxy group, alkyl group, and cyclo. It is substituted with one or two or more substituents selected from the group consisting of an alkyl group, heterocycloalkyl group, alkoxy group, aryl group, heteroaryl group, amine group and silyl group, or is substituted with a substituent in which two or more of the substituents are connected, or any substituent. It means not having any.

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

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.

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 unsubstituted amine group. 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 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, depending on the characteristics of the introduced structure and substituents, it can be used as a light-emitting layer within the organic layer. It can be used as a host material.

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.

In this way, the organic compound according to the present invention can synthesize organic compounds with various properties through a characteristic skeletal structure with unique properties and a moiety with unique properties introduced thereto, and as a result, the present invention When the organic compound according to the invention is applied to various organic layer materials such as a light-emitting layer, the light-emitting properties such as luminous efficiency of the device can be further improved, and preferably, it is used as a host material in the light-emitting layer to create an organic light-emitting device with excellent light-emitting properties. can be implemented.

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 a light emitting layer, etc., and one or more of the layers may include an organic compound host material represented by [Chemical Formula I].

In addition, the organic light-emitting device according to the present invention may be composed of a plurality of host materials in the light-emitting layer, and may be formed by mixing or stacking one or more other compounds in addition to the compound according to the present invention.

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

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, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for illustrating the present invention in more detail, and the scope of the present invention is not limited thereto, and various changes and modifications are possible within the scope and technical idea of the present invention as is known in the art. It will be self-evident to those with knowledge.

Synthesis example 1: Synthesis of Compound 6

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

(6-Phenyldibenzo[b,d]furan-4-yl)boronic acid (10.0 g, 0.035 mol), 1-Bromo-4-fluorobenzene (7.3 g, 0.042 mol), K ₂ CO ₃ (14.4 g, 0.104 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 69.0%) of <Intermediate 6-1>.

(2) Manufacturing example 2: Synthesis of intermediate 6-2

Add DMF to Intermediate 6-1 (10.0 g, 0.030 mol), 9H-carbazol-4-ylboronic acid (7.5 g, 0.036 mol), and Cs ₂ CO ₃ (6.1 g, 0.044 mol) and reflux at 150°C for 12 hours. The reaction was stirred. After completion of the reaction, it was extracted, concentrated, and recrystallized with a column to obtain 10.7 g of <Intermediate 6-2> (yield 68.4%).

(3) Manufacturing example 3: Synthesis of Compound 6

Intermediate 6-2 (10.0 g, 0.019 mol), 4-Bromobiphenyl (5.3 g, 0.023 mol), K ₂ CO ₃ (7.8 g, 0.057 mol), Pd(PPh ₃ ) ₄ (0.4 g, 0.0004 mol) toluene 200 mL, 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 recrystallized with a column to obtain 9.1 g of <Compound 6> (yield 75.5%).

LC/MS: m/z=637[(M) ⁺ ]

Synthesis example 2: Synthesis of Compound 7

(One) Manufacturing example 1: Synthesis of Compound 7

Intermediate 6-2 (10.0 g, 0.019 mol), 3-Bromobiphenyl (5.3 g, 0.028 mol), K ₂ CO ₃ (7.8 g, 0.057 mol), Pd(PPh ₃ ) ₄ (0.4 g, 0.0004 mol) toluene 200 mL, 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 recrystallized with a column to obtain 8.6 g of <Compound 7> (yield 71.4%).

LC/MS: m/z=637[(M) ⁺ ]

Synthesis example 3: Synthesis of Compound 9

(One) Manufacturing example 1: Synthesis of Compound 9

Intermediate 6-2 (10.0 g, 0.019 mol), 2-Bromobiphenyl (5.3 g, 0.028 mol), K ₂ CO ₃ (7.8 g, 0.057 mol), Pd(PPh ₃ ) ₄ (0.4 g, 0.0004 mol) toluene 200 mL, 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 recrystallized with a column to obtain 8.8 g of <Compound 9> (yield 73.1%).

LC/MS: m/z=637[(M) ⁺ ]

Synthesis example 4: Synthesis of Compound 11

(One) Manufacturing example 1: Synthesis of Compound 11

Intermediate 6-2 (10.0 g, 0.019 mol), 5'-Bromo-1,1':3',1"-terphenyl (7.0 g, 0.023 mol), K ₂ CO ₃ (7.8 g, 0.057 mol), Pd To (PPh ₃ ) ₄ (0.4 g, 0.0004 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, extraction and concentration were performed on a column and recrystallization. Thus, 9.1 g (yield 67.5%) of <Compound 11> was obtained.

LC/MS: m/z=713[(M) ⁺ ]

Synthesis example 5: Synthesis of compound 24

(One) Manufacturing example 1: Synthesis of intermediate 24-1

(6-Phenyldibenzo[b,d]furan-4-yl)boronic acid (10.0 g, 0.035 mol) 1-Bromo-3-fluorobenzene (7.3 g, 0.042 mol), K ₂ CO ₃ (14.4 g, 0.104 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 7.6 g (yield 64.7%) of <Intermediate 24-1>.

(2) Manufacturing example 2: Synthesis of intermediate 24-2

Add 500 mL of DMF to Intermediate 24-1 (10.0 g, 0.030 mol), 4-Fluoroiodobenzene (7.5 g, 0.036 mol), and Cs ₂ CO ₃ (6.1 g, 0.044 mol) and react by refluxing and stirring at 150°C for 12 hours. I ordered it. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 10.3 g of <Intermediate 24-2> (yield 63.8%).

(3) Manufacturing example 3: Synthesis of Compound 24

Intermediate 24-2 (10.0 g, 0.019 mol), 3-Bromobiphenyl (5.3 g, 0.023 mol), K ₂ CO ₃ (7.8 g, 0.057 mol), Pd(PPh ₃ ) ₄ (0.4 g, 0.0004 mol) toluene 200 mL, 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 recrystallized with a column to obtain 8.1 g of <Compound 24> (yield 67.2%).

LC/MS: m/z=637[(M) ⁺ ]

Synthesis example 6: Synthesis of Compound 85

(One) Manufacturing example 1: Synthesis of intermediate 85-1

2-Chloro-9H-carbazole (10.0 g, 0.050 mol), 4-Bromo-4'-fluoro-1,1'-biphenyl (14.9 g, 0.060 mol), Cs ₂ CO ₃ (10.3 g, 0.074 mol) DMF was added and the reaction was stirred under reflux at 150°C for 12 hours. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 11.5 g of <Intermediate 85-1> (yield 53.6%).

(2) Manufacturing example 2: Synthesis of intermediate 85-2

(6-Phenyldibenzo[b,d]furan-4-yl)boronic acid (10.0 g, 0.035 mol), intermediate 85-1 (18.0 g, 0.042 mol), K ₂ CO ₃ (14.4 g, 0.104 mol), Pd (PPh ₃ ) ₄ (0.8 g, 0.0007 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 completion of the reaction, the extract was extracted, concentrated, and recrystallized using a column to obtain 15.2 g of <Intermediate 85-2> (yield 73.5%).

(3) Manufacturing example 3: Synthesis of Compound 85

Intermediate 85-2 (10.0 g, 0.017 mol), 4-Biphenylboronic acid (4.0 g, 0.020 mol), K ₂ CO ₃ (7.0 g, 0.050 mol), Pd(OAc) ₂ (1.0 g, 0.8 mmol), -Phos (0.8 g, 1.7 mmol), 200 mL of THF, and 50 mL of H ₂ O were added and stirred at 70°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and recrystallized with a column to obtain 8.7 g of <Compound 85> (yield 72.7%).

LC/MS: m/z=713[(M) ⁺ ]

Synthesis example 7: Synthesis of Compound 108

(One) Manufacturing example 1: Synthesis of intermediate 108-1

Add DMF to 3-Chlorocarbazole (10.0 g, 0.050 mol), 1-Bromo-2-fluorobenzene (10.4 g, 0.060 mol), and Cs ₂ CO ₃ (10.3 g, 0.074 mol), reflux and stir at 150°C for 12 hours. reacted. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 10.2 g of <Intermediate 108-1> (yield 57.7%).

(2) Manufacturing example 2: Synthesis of intermediate 108-2

(6-Phenyldibenzo[b,d]furan-4-yl)boronic acid (10.0 g, 0.035 mol), intermediate 108-1 (14.9 g, 0.042 mol), K ₂ CO ₃ (14.4 g, 0.104 mol), Pd (PPh ₃ ) ₄ (0.8 g, 0.0007 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 completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 11.8 g of <Intermediate 108-2> (yield 65.4%).

(3) Manufacturing example 3: Synthesis of Compound 108

Intermediate 108-2 (10.0 g, 0.019 mol), B-[1,1':3',1"-Terphenyl]-4'-ylboronic acid (6.3 g, 0.023 mol), K ₂ CO ₃ (8.0 g, 0.058 mol), Pd(OAc) ₂ (1.1 g, 0.001 _mol ), After completion of the reaction, the extract was extracted, concentrated, and recrystallized with a column to obtain 7.5 g of <Compound 108> (yield 54.6%).

LC/MS: m/z=713[(M) ⁺ ]

Synthesis example 8: Synthesis of Compound 121

(One) Manufacturing example 1: Synthesis of intermediate 121-1

4-Bromo-2-chloro-1,1'-biphenyl (10.0 g, 0.037 mol), Bis(pinacolato)diboron (11.4 g, 0.045 mol), KOAc (11.0 g, 0.112 mol), Pd(dppf)Cl ₂ (1.4 g, 1.9 mmol) was added to 200 mL of dioxane and stirred at 100°C for 12 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 8.4 g (yield 71.4%) of <Intermediate 121-1>.

(2) Manufacturing example 2: Synthesis of intermediate 121-2

Intermediate 121-1 (10.0 g, 0.032 mol), 1-Iodo-2-nitrobenzene (9.5 g, 0.038 mol), K ₂ CO ₃ (13.2 g, 0.095 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 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 6.5 g of <Intermediate 121-2> (yield 66.0%).

(3) Manufacturing example 3: Synthesis of intermediate 121-3

Intermediate 121-2 (10.0 g, 0.032 mol), PPh ₃ (21.2 g, 0.081 mol), and 350 mL of dichlorobenzene were added and reacted by refluxing and stirring at 180°C for 3 hours. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 6.4 g of <Intermediate 121-3> (yield 71.4%).

(4) Manufacturing example 4: Synthesis of intermediate 121-4

DMF was added to Intermediate 6-1 (10.0 g, 0.030 mol), Intermediate 121-3 (9.8 g, 0.036 mol), and Cs ₂ CO ₃ (6.1 g, 0.044 mol), and the mixture was refluxed and stirred at 150°C for 12 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 <Intermediate 121-4> (yield 61.9%).

(5) Manufacturing example 5: Synthesis of Compound 121

Intermediate 121-4 (10.0 g, 0.017 mol), Phenylboronic acid (2.5 g, 0.020 mol), K ₂ CO ₃ (7.0 g, 0.050 mol), Pd(OAc) ₂ (1.0 g, 0.8 mmol), X-Phos (0.8 g, 1.7 mmol), 200 mL of THF and 50 mL of H ₂ O were added and stirred at 70°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 7.1 g of <Compound 121> (yield 66.4%).

LC/MS: m/z=637[(M) ⁺ ]

Synthesis example 9: Synthesis of Compound 136

(One) Manufacturing example 1: Synthesis of intermediate 136-1

(6-Phenyldibenzo[b,d]furan-4-yl)boronic acid (10.0 g, 0.035 mol), 3-Bromo-3'-fluoro-1,1'-biphenyl (10.5 g, 0.042 mol), K ₂ 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added to CO ₃ (14.4 g, 0.104 mol) and 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 8.8 g (yield 61.2%) of <Intermediate 136-1>.

(2) Manufacturing example 2: Synthesis of intermediate 136-2

DMF was added to Intermediate 136-1 (10.0 g, 0.024 mol), Intermediate 121-3 (8.0 g, 0.029 mol), and Cs ₂ CO ₃ (5.0 g, 0.036 mol), and the mixture was refluxed and stirred at 150°C for 12 hours to react. . After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 10.2 g of <Intermediate 136-2> (yield 62.9%).

(3) Manufacturing example 3: Synthesis of Compound 136

Intermediate 136-2 (10.0 g, 0.015 mol), Phenylboronic acid (2.2 g, 0.018 mol), K ₂ CO ₃ (6.2 g, 0.045 mol), Pd(OAc) ₂ (0.9 g, 0.7 mmol), X-Phos (0.7 g, 1.5 mmol), 200 mL of THF and 50 mL of H ₂ O were added and stirred at 70°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 6.8 g of <Compound 136> (yield 64.0%).

LC/MS: m/z=713[(M) ⁺ ]

Synthesis example 10: Synthesis of Compound 177

(One) Manufacturing example 1: Synthesis of intermediate 177-1

2-Bromo-6-chloro-1,1'-biphenyl (10.0 g, 0.037 mol), Bis(pinacolato)diboron (11.4 g, 0.045 mol), KOAc (11.0 g, 0.112 mol), Pd(dppf)Cl ₂ (1.4 g, 1.9 mmol) was added to 200 mL of dioxane and stirred at 100°C for 12 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 8.3 g (yield 70.6%) of <Intermediate 177-1>.

(2) Manufacturing example 2: Synthesis of intermediate 177-2

Intermediate 177-1 (10.0 g, 0.032 mol), 1-Iodo-2-nitrobenzene (9.5 g, 0.038 mol), K ₂ CO ₃ (13.2 g, 0.095 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 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 6.1 g (yield 62.0%) of <Intermediate 177-2>.

(3) Manufacturing example 3: Synthesis of intermediate 177-3

Intermediate 177-2 (10.0 g, 0.032 mol), PPh ₃ (21.2 g, 0.081 mol), and 350 mL of dichlorobenzene were added and reacted by refluxing and stirring at 180°C for 3 hours. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 6.8 g (yield 75.8%) of <Intermediate 177-3>.

(4) Manufacturing example 4: Synthesis of intermediate 177-4

DMF was added to Intermediate 24-1 (10 g, 0.030 mol), Intermediate 177-3 (9.8 g, 0.036 mol), and Cs ₂ CO ₃ (6.1 g, 0.044 mol), and the reaction was stirred under reflux at 150°C for 12 hours. . After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 11.5 g of <Intermediate 177-4> (yield 65.3%).

(5) Manufacturing example 5: Synthesis of Compound 177

Intermediate 177-4 (10.0 g, 0.017 mol), Phenylboronic acid (2.5 g, 0.020 mol), K ₂ CO ₃ (7.0 g, 0.050 mol), Pd(OAc) ₂ (1.0 g, 0.8 mmol), X-Phos (0.8 g, 1.7 mmol), 200 mL of THF and 50 mL of H ₂ O were added and stirred at 70°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 7.7 g of <Compound 177> (yield 72.0%).

LC/MS: m/z=637[(M) ⁺ ]

Synthesis example 11: Synthesis of Compound 185

(One) Manufacturing example 1: Synthesis of intermediate 185-1

(6-Phenyldibenzo[b,d]furan-4-yl)boronic acid (10.0 g, 0.035 mol), 4-Fluoro-4'-iodo-1,1'-biphenyl (12.4 g, 0.042 mol), K ₂ 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added to CO ₃ (14.4 g, 0.104 mol) and 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, extraction was performed, concentration was performed, and then column was used to obtain 9.8 g of <Intermediate 185-1> (yield 68.1%).

(2) Manufacturing example 2: Synthesis of intermediate 185-2

DMF was added to Intermediate 185-1 (10 g, 0.024 mol), Intermediate 177-3 (8.0 g, 0.029 mol), and Cs ₂ CO ₃ (5.0 g, 0.036 mol), and the mixture was refluxed and stirred at 150°C for 12 hours to react. . After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 10.6 g of <Intermediate 185-2> (yield 65.4%).

(3) Manufacturing example 3: Synthesis of Compound 185

Intermediate 185-2 (10.0 g, 0.015 mol), Phenylboronic acid (2.2 g, 0.018 mol), K ₂ CO ₃ (6.2 g, 0.047 mol), Pd(OAc) ₂ (0.9 g, 0.7 mmol), X-Phos (0.7 g, 1.5 mmol), 200 mL of THF and 50 mL of H ₂ O were added and stirred at 70°C for 6 hours to react. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 8.2 g of <Compound 185> (yield 77.2%).

LC/MS: m/z=713[(M) ⁺ ]

Synthesis example 12: Synthesis of compound 192

(One) Manufacturing example 1: Synthesis of Compound 192

Intermediate 6-2 (10.0 g, 0.019 mol), 2-Bromo-9,9-dimethylfluorene (6.2 g, 0.023 mol), K ₂ CO ₃ (7.8 g, 0.057 mol), Pd(PPh ₃ ) ₄ (0.4 g , 0.0004 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, it was extracted, concentrated, and recrystallized with a column to obtain 8.1 g of <Compound 192> (yield 63.3%).

LC/MS: m/z=677[(M) ⁺ ]

Synthesis example 13: Synthesis of compound 197

(One) Manufacturing example 1: Synthesis of Compound 197

Add DMF to Intermediate 6-1 (10.0 g, 0.030 mol), 1,3-diphenyl-9H-carbazole (11.3 g, 0.036 mol), and Cs ₂ CO ₃ (6.1 g, 0.044 mol) and stir at 150°C for 12 hours. The reaction was stirred under reflux. After completion of the reaction, the extract was extracted, concentrated, and recrystallized with a column to obtain 11.8 g of <Compound 197> (yield 62.6%).

LC/MS: m/z=637[(M) ⁺ ]

Synthesis example 14: Synthesis of compound 208

(One) Manufacturing example 1: Synthesis of Compound 208

Add 500 mL of DMF to Intermediate 24-1 (10.0 g, 0.030 mol), 2,4-diphenyl-9H-carbazole (11.3 g, 0.036 mol), and Cs ₂ CO ₃ (6.1 g, 0.044 mol) and stir at 150°C for 12 days. The reaction was stirred under reflux for an hour. After completion of the reaction, the extract was extracted, concentrated, and recrystallized with a column to obtain 12.8 g of <Compound 208> (yield 67.9%).

LC/MS: m/z=637[(M) ⁺ ]

Synthesis example 15: Synthesis of compound 240

(One) Manufacturing example 1: Synthesis of intermediate 240-1

(6-Phenyldibenzo[b,d]thiophen-4-yl)boronic acid (10.0 g, 0.033 mol), 1-Bromo-4-fluorobenzene-d4 (7.1 g, 0.040 mol), K ₂ CO ₃ (13.6 g, 0.099 mol), Pd(PPh ₃ ) ₄ (0.8 g, 0.7 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 columnarized to obtain 6.8 g of <Intermediate 240-1> (yield 57.7%).

(2) Manufacturing example 2: Synthesis of intermediate 240-2

Add DMF to intermediate 240-1 (10.0 g, 0.028 mol), 9H-carbazol-4-ylboronic acid (7.1 g, 0.034 mol), and Cs ₂ CO ₃ (5.8 g, 0.042 mol) and reflux at 150°C for 12 hours. The reaction was stirred. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 10.4 g of <Intermediate 240-2> (yield 67.9%).

(3) Manufacturing example 3: Synthesis of Compound 240

Intermediate 240-2 (10.0 g, 0.018 mol), 4-Bromobiphenyl (5.1 g, 0.022 mol), K ₂ CO ₃ (7.6 g, 0.055 mol), Pd(PPh ₃ ) ₄ (0.4 g, 0.0004 mol) toluene 200 mL, 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 recrystallized with a column to obtain 6.2 g of <Compound 240> (yield 51.8%).

LC/MS: m/z=657[(M) ⁺ ]

Synthesis example 16: Synthesis of compound 263

(One) Manufacturing example 1: Synthesis of intermediate 263-1

4,6-dibromodibenzo[b,d]thiophene (10.0 g, 0.029 mol), [1,1'-biphenyl]-4-ylboronic acid (7.0 g, 0.035 mol), K ₂ CO ₃ (12.1 g, 0.088 mol) ), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added to Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 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 5.1 g (yield 42.0%) of <Intermediate 263-1>.

(2) Manufacturing example 2: Synthesis of intermediate 263-2

Intermediate 263-1 (10.0 g, 0.024 mol), Bis(pinacolato)diboron (7.3 g, 0.029 mol), KOAc (7.1 g, 0.072 mol), Pd(dppf)Cl ₂ (0.9 g, 0.001 mol) dioxane 200 mL was added and stirred at 100°C for 12 hours to react. After completion of the reaction, the extract was extracted, concentrated, and columnarized to obtain 7.8 g of <Intermediate 263-2> (yield 70.1%).

(3) Manufacturing example 3: Synthesis of intermediate 263-3

Intermediate 263-2 (10.0 g, 0.022 mol), 1-Bromo-4-fluorobenzene (4.5. g, 0.026 mol), K ₂ CO ₃ (9.0 g, 0.065 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.0004 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 6.2 g (yield 66.6%) of <Intermediate 263-3>.

(4) Manufacturing example 4: Synthesis of intermediate 263-4

Add DMF to intermediate 263-3 (10 g, 0.023 mol), 9H-carbazol-3-ylboronic acid (5.9 g, 0.028 mol), and Cs ₂ CO ₃ (4.8 g, 0.035 mol) and reflux at 150°C for 12 hours. The reaction was stirred. After completion of the reaction, the extract was extracted, concentrated, and then recrystallized with a column to obtain 8.6 g of <Intermediate 263-4> (yield 59.6%).

(5) Manufacturing example 5: Synthesis of Compound 263

Intermediate 263-4 (10.0 g, 0.016 mol), 4-Bromobiphenyl (4.5 g, 0.019 mol), K ₂ CO ₃ (6.7 g, 0.048 mol), Pd(PPh ₃ ) ₄ (0.4 g, 0.0003 mol) toluene 200 mL, 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 recrystallized with a column to obtain 7.2 g of <Compound 263> (yield 61.3%).

LC/MS: m/z=729[(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 24

Using the compound implemented according to the present invention as a host, an organic light-emitting device having the following device structure was manufactured, and then the light-emitting properties including current efficiency were measured.

ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (HT1, 100 nm) / electron blocking layer (EB1, 10 nm) / light emitting layer (first host (compound according to the present invention): second host ( BH2), 30 nm) / electron transport layer (ET1, 30 nm) / LiF (1 nm) / Al (100 nm)

To form a hole injection layer on the top of the ITO transparent electrode, [HAT-CN] was deposited to a thickness of 5 nm, and then a hole transport layer of 100 nm was formed using [HT1]. The hole blocking layer was deposited to a thickness of 10 nm using [EB1]. In addition, the first host of the light emitting layer used a compound according to the present invention shown in Table 1 below, the second host used a 6:4 mixture using [BH2], and the dopant was doped with [BD1]. It was co-deposited to a thickness of 30 nm. Additionally, a 30 nm electron transport layer (50% doped with [ET1] compound Liq below) was deposited. Then, LiF was deposited to a thickness of 1 nm as an electron injection layer, and then Al 100 nm was deposited 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 in the device structure of Example 1, except that the following [BH1] was used as the first host instead of the compound according to the present invention.

Experiment example 1: element Example Luminous properties from 1 to 24

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 first host second host V cd/A CIEx CIey One Compound 1 BH2 4.63 25.09 0.127 0.132 2 compound 2 BH2 4.71 25.02 0.120 0.129 3 Compound 6 BH2 4.80 25.16 0.131 0.133 4 Compound 7 BH2 4.68 24.66 0.126 0.130 5 Compound 9 BH2 4.72 24.73 0.120 0.138 6 Compound 11 BH2 4.56 25.21 0.124 0.135 7 Compound 42 BH2 4.62 24.98 0.125 0.136 8 Compound 53 BH2 4.70 25.05 0.116 0.131 9 Compound 85 BH2 4.57 25.19 0.125 0.135 10 Compound 90 BH2 4.71 25.37 0.229 0.133 11 compound 101 BH2 4.78 25.04 0.133 0.139 12 Compound 103 BH2 4.64 25.42 0.133 0.131 13 Compound 108 BH2 4.68 25.09 0.128 0.132 14 Compound 121 BH2 4.70 25.11 0.129 0.133 15 Compound 136 BH2 4.58 25.24 0.121 0.130 16 Compound 162 BH2 4.52 25.40 0.123 0.135 17 Compound 171 BH2 4.62 25.20 0.124 0.136 18 Compound 199 BH2 4.67 25.14 0.133 0.139 19 Compound 205 BH2 4.61 24.42 0.133 0.131 20 Compound 207 BH2 4.64 24.95 0.125 0.133 21 Compound 237 BH2 4.70 24.73 0.134 0.137 22 Compound 238 BH2 4.64 24.97 0.131 0.139 23 Compound 261 BH2 4.50 24.62 0.127 0.133 24 Compound 266 BH2 4.67 25.09 0.128 0.132 Comparative Example 1 BH1 BH2 5.63 22.41 0.130 0.145

Looking at the results shown in [Table 1], in an organic light-emitting device in which the host material in the light-emitting layer is composed of a plurality of hosts, when the compound according to the present invention is used as a host material for the light-emitting layer in the organic light-emitting device, the light-emitting layer composed of a conventional host material It can be confirmed that characteristics such as low-voltage driving and luminous efficiency are significantly superior to the organic light-emitting device (Comparative Example 1) employing .

[HAT-CN] [HT1] [EB1] [ET1]

[BH1] [BH2] [BD1]

device Example 25 to 56

Using the compound implemented according to the present invention as a host, an organic light-emitting device having the following device structure was manufactured, and then the light-emitting properties including current efficiency were measured.

ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (HT1, 100 nm) / electron blocking layer (EB1, 10 nm) / light emitting layer (first host (compound according to the present invention): second host: (GH2), 30 nm) / electron transport layer (ET1, 30 nm) / LiF (1 nm) / Al (100 nm)

To form a hole injection layer on the top of the ITO transparent electrode, [HAT-CN] was deposited to a thickness of 5 nm, and then a hole transport layer was deposited at 100 nm using [HT1]. The hole blocking layer was deposited to a thickness of 10 nm using [EB1]. In addition, the first host of the light emitting layer used a compound according to the present invention shown in Table 1 below, the second host used a 6:4 mixture using [GH2], and the dopant was Ir(ppy) _3. was doped and co-deposited to a thickness of 30 nm. Additionally, a 30 nm electron transport layer (50% doped with [ET1] compound Liq below) was deposited. Then, LiF was deposited to a thickness of 1 nm as an electron injection layer, and then Al 100 nm was deposited to produce an organic light emitting device.

device Comparative example 2

The organic light emitting device for Device Comparative Example 2 was manufactured in the same manner as in Example 25, except that [GH1] below was used as the first host instead of the compound according to the present invention.

Experiment example 2: element Example Luminous properties of 25 to 56

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

Example first host second host V cd/A CIEx CIey 25 Compound 1 GH2 3.63 54.09 0.327 0.612 26 compound 2 GH2 3.71 53.02 0.320 0.621 27 Compound 6 GH2 3.80 55.16 0.331 0.613 28 Compound 7 GH2 3.68 54.66 0.326 0.612 29 Compound 9 GH2 3.72 52.73 0.320 0.618 30 Compound 11 GH2 3.56 54.21 0.324 0.615 31 Compound 24 GH2 3.41 54.51 0.332 0.607 32 Compound 30 GH2 3.53 55.93 0.328 0.612 33 Compound 37 GH2 3.62 53.00 0.323 0.615 34 Compound 41 GH2 3.61 54.20 0.324 0.616 35 Compound 52 GH2 3.59 57.18 0.317 0.622 36 Compound 85 GH2 3.65 54.84 0.329 0.617 37 Compound 109 GH2 3.73 54.03 0.320 0.620 38 Compound 114 GH2 3.81 55.16 0.328 0.613 39 Compound 119 GH2 3.72 53.66 0.326 0.613 40 Compound 120 GH2 3.79 51.43 0.322 0.616 41 Compound 121 GH2 3.56 54.21 0.323 0.615 42 Compound 124 GH2 3.52 52.51 0.332 0.607 43 Compound 156 GH2 3.63 55.93 0.328 0.612 44 Compound 177 GH2 3.73 57.18 0.317 0.622 45 Compound 185 GH2 3.69 53.05 0.316 0.621 46 Compound 192 GH2 3.51 54.19 0.325 0.615 47 Compound 197 GH2 3.58 52.37 0.329 0.613 48 Compound 208 GH2 3.56 53.74 0.320 0.618 49 Compound 211 GH2 3.59 52.39 0.324 0.614 50 Compound 213 GH2 3.71 52.04 0.326 0.615 51 Compound 217 GH2 3.50 53.10 0.323 0.616 52 Compound 222 GH2 3.57 56.92 0.326 0.611 53 Compound 223 GH2 3.46 51.37 0.329 0.612 54 Compound 224 GH2 3.54 55.46 0.329 0.614 55 Compound 240 GH2 3.71 55.53 0.326 0.613 56 Compound 263 GH2 3.57 57.07 0.324 0.617 Comparative Example 2 GH1 GH2 4.05 45.27 0.328 0.604

Looking at the results shown in [Table 2], in an organic light-emitting device in which the host material in the light-emitting layer is composed of a plurality of hosts, when the compound according to the present invention is used as a host material for the light-emitting layer in the organic light-emitting device, the light-emitting layer composed of a conventional host material It can be confirmed that characteristics such as low-voltage driving and luminous efficiency are significantly superior to those of the organic light-emitting device (Comparative Example 2) employing .

[HAT-CN] [HT1] [EB1] [ET1]

[GH1] [GH2] [Ir(ppy) ₃ ]

Claims (11)

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

In the above [Chemical Formula I],
X is O or S,
Ar ₁ is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms,
L is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, p is an integer of 1 to 3, and when p is 2 or more, the plurality of Ls are the same or different from each other,
Ar ₂ is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, and a substituted or unsubstituted aryl group with 6 to 20 carbon atoms. any one selected from among, q is an integer of 1 to 2, and when q is 2, a plurality of Ar ₂ are the same or different from each other,
However, when q is 1 and Ar ₂ is a substituted or unsubstituted aryl group, the aryl group is a substituted or unsubstituted aryl group in which at least two or more aryl groups are connected,
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,
In the definition of Ar ₁ to Ar ₂ and L, ‘substituted or unsubstituted’ means that Ar ₁ to Ar ₂ and L are each deuterium, halogen group, cyano group, nitro group, hydroxy group, alkyl group, cycloalkyl group, It is substituted with one or two or more substituents selected from the group consisting of heterocycloalkyl group, alkoxy group, aryl group, heteroaryl group, amine group and silyl group, or is substituted with a substituent in which two or more of the above substituents are connected, or has no substituent. An organic compound that does not mean anything. 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 3,
An organic compound characterized in that the deuterium (D) substitution rate is 20 to 80%. According to paragraph 3,
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 [Compound 1] to [Compound 307]:

























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 an organic compound of [Chemical Formula I] according to claim 1. In clause 7,
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 8,
An organic light-emitting device comprising an organic compound represented by [Chemical Formula I] in the light-emitting layer. According to clause 9,
An organic light-emitting device, characterized in that the organic compound represented by [Chemical Formula I] is a host material in the light-emitting layer. According to clause 10,
An organic light-emitting device characterized in that the host material is composed of a plurality of compounds including one or more other compounds in addition to the organic compound represented by [Chemical Formula I] and mixed or stacked.