KR20230099656A - Novel organic compounds and an organic electroluminescent device comprising the same - Google Patents

Abstract

In the organic electroluminescent device in which an organic thin film layer composed of one or a plurality of layers including at least a light emitting layer is laminated between a cathode and an anode,
The compound constituting the organic thin film layer provides an organic electroluminescent device characterized in that it contains tritium in its chemical structure.

Description

Novel organic compounds and an organic electroluminescent device comprising the same {Novel organic compounds and an organic electroluminescent device comprising the same}

The present invention relates to the display field, and more particularly, to an organic compound that can be used in manufacturing an organic light emitting device, which is a kind of display, and an organic light emitting device including the organic compound.

Until now, liquid crystal displays have occupied most of the flat panel displays, but efforts to develop new flat panel displays that are more economical and superior in performance and differentiated from liquid crystal displays are being actively conducted worldwide. Recently, an organic light emitting device that has been in the limelight as a next-generation flat panel display has advantages such as a low driving voltage, a fast response speed, and a wide viewing angle compared to a liquid crystal display.

The structure of the organic light emitting device is a substrate, an anode, a hole injection layer that accepts holes from the anode, a hole transport layer that transports holes, an electron blocking layer that blocks electrons from entering the hole transport layer from the light emitting layer, and a combination of holes and electrons to emit light. It consists of a light emitting layer that emits light, a hole blocking layer that blocks the entry of holes from the light emitting layer to the electron transport layer, an electron transport layer that accepts electrons from the cathode and transports them to the light emitting layer, an electron injection layer that accepts electrons from the cathode, and a cathode. In some cases, the light emitting layer may be formed by doping the electron transport layer or the hole transport layer with a small amount of fluorescent or phosphorescent dye without a separate light emitting layer. can be performed simultaneously. The organic thin film layers between the two electrodes are formed by methods such as vacuum deposition, spin coating, inkjet printing, or laser thermal transfer. The reason why the organic light emitting device is manufactured in a multi-layered thin film structure is to stabilize the interface between the electrode and the organic material, and in the case of the organic material, since the difference in movement speed between holes and electrons is large, an appropriate hole transport layer and electron transport layer are used to transport holes. This is because luminous efficiency can be increased by effectively transferring electrons and holes to the light emitting layer so that the density of holes and electrons is balanced.

The driving principle of the organic light emitting device is as follows. When a voltage is applied between the anode and the cathode, holes injected from the anode move to the light emitting layer via the hole injection layer and the hole transport layer. Meanwhile, electrons are injected into the light emitting layer from the cathode via the electron injection layer and the electron transport layer, and carriers recombine in the light emitting layer region to generate excitons. This exciton changes from an excited state to a ground state, and as a result, fluorescent molecules in the light emitting layer emit light, thereby forming an image. At this time, light emission while falling to the ground state through a singlet excited state is called "fluorescence", and light emission while falling to the ground state through a triplet excited state is called "phosphorescence". In the case of fluorescence, the probability of a singlet excited state is 25% (triplet state 75%), and there is a limit in luminous efficiency, whereas when phosphorescence is used, up to 75% of the triplet state and 25% of the singlet excited state can be used for light emission. Theoretically, up to 100% internal quantum efficiency is possible.

Lifespan and efficiency are the most problematic issues in organic light emitting devices, and as displays become larger, these efficiency and lifespan problems must be solved.

In particular, in the case of blue, materials such as ADN and DPVBi are used as host materials, and aromatic amine compounds, copper phthalocyanine compounds, carbazole derivatives, perylene derivatives, and coumarin are used as dopants. Materials such as coumarine-based derivatives and pyrene-based derivatives are used, but there is a problem in that it is difficult to obtain deep blue and the luminous lifetime becomes shorter as the wavelength goes shorter.

Therefore, development of a deep blue material with a long lifespan and development of other organic materials matching the energy level with the blue material are required to realize a full color display of natural color.

Republic of Korea Patent No. 1008462210000 Republic of Korea Patent No. 1023130450000 Republic of Korea Patent No. 1018256120000 Republic of Korea Patent No. 1012267000000 Republic of Korea Patent No. 1022021710000

The present invention was made to solve the above problems of the prior art,

An object of the present invention is to provide a novel organic compound that is used as a host material to improve the luminous efficiency and luminous lifetime of an organic light emitting device.

In addition, an object of the present invention is to provide an organic light emitting device with improved driving voltage, luminous efficiency, and luminous lifetime by including the host material as described above.

In addition, an object of the present invention is to provide an organic light emitting device with further improved driving voltage, device efficiency and lifetime by including the host material and a specific hole transport layer material in combination.

Tritium is a hydrogen that is heavier than normal hydrogen, which is the most abundant in nature, and is denoted by T or 3H. Usually, a hydrogen atom consists of one proton and one electron, but a tritium atom has two more neutrons attached to it. Since the weight of electrons is negligible, it is 'three times as heavy as hydrogen' as the name suggests. In addition to being heavy, tritium has radioactivity that normal hydrogen does not. Tritium gives off an energy of 18.6 keV as it changes to helium 3 (2 protons + 1 neutron), which has one less neutron than normal helium (2 protons + 2 neutrons). Because the energy is not great, it cannot penetrate paper or water, nor can it penetrate human skin. This means that compared to other radioactive substances, tritium is relatively safe. Such tritium can emit beta rays, and the emitted beta rays can stimulate fluorescent materials, so if such tritium is used as an OLED material, the lifespan and efficiency, which are the most problematic in organic light emitting devices, will be greatly improved. You will be able to. Since organic molecules or organic/metal molecules that actually emit fluorescence and phosphorescence per unit time when a voltage is applied to the organic light emitting device are only a small portion, such tritium is present in a very small amount in the compound constituting the organic light emitting device. It will be possible to greatly improve the lifetime and efficiency compared to the organic light emitting device.

In addition, the present invention provides an organic compound represented by Formula 1 below:

[Formula 1]

in the above formula

Ar1 and Ar2 are each independently selected from tritium, deuterium, hydrogen, CN, straight or branched chain alkyl having 1 to 40 carbon atoms, alkoxy having 1 to 40 carbon atoms, thioalkyl having 1 to 40 carbon atoms, cycloalkyl having 3 to 40 carbon atoms, Phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl , A pyrazinyl group, a pyrimidinyl group, and an aromatic hydrocarbon group having 6 to 60 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of a quinolinyl group,

tritium, deuterium, hydrogen, CN, straight or branched chain alkyl of 1 to 40 carbon atoms, alkoxy of 1 to 40 carbon atoms, thioalkyl of 1 to 40 carbon atoms, cycloalkyl of 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl , anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, spirobi [fluorene], carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyra Hetero having 5 to 70 carbon atoms, substituted or unsubstituted with one or more selected from the group consisting of zinyl, pyrimidinyl, and quinolinyl, and containing one or more elements selected from the group consisting of S, O, N, and Si It is an aromatic hydrocarbon group,

R1, R2, R3, R4, R5, R6, R7 and R8 are each independently tritium, deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , carbon atoms a straight-chain or branched-chain alkyl group of 1 to 40 carbon atoms, an alkoxy group of 1 to 40 carbon atoms, a thioalkyl group of 1 to 40 carbon atoms, or a cycloalkyl group of 3 to 40 carbon atoms;

tritium, deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , straight or branched chain alkyl of 1 to 40 carbon atoms, alkoxy of 1 to 40 carbon atoms, 1 carbon atom thioalkyl of 3 to 40 carbon atoms, cycloalkyl of 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carba An aromatic hydrocarbon group having 6 to 60 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of zoyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, and quinolinyl,

tritium, deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , straight or branched chain alkyl of 1 to 40 carbon atoms, alkoxy of 1 to 40 carbon atoms, 1 carbon atom thioalkyl of 3 to 40 carbon atoms, cycloalkyl of 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, spirobi[ fluorene], carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl group, and unsubstituted or substituted with one or more selected from the group consisting of S, O, A heteroaromatic hydrocarbon group having 5 to 70 carbon atoms containing at least one element selected from the group consisting of N and Si;

tritium, deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , straight or branched chain alkyl of 1 to 40 carbon atoms, alkoxy of 1 to 40 carbon atoms, 1 carbon atom Phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl, phenanthrenyl substituted or unsubstituted with one or more selected from the group consisting of thioalkyl groups having 3 to 40 carbon atoms and cycloalkyl groups having 3 to 40 carbon atoms At least one selected from the group consisting of pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and pyrimidinyl groups is an amino group substituted with

In addition, the present invention is an organic electroluminescent device in which an organic thin film layer composed of one or a plurality of layers including at least a light emitting layer is laminated between a cathode and an anode,

It provides an organic electroluminescent device characterized in that the light emitting layer contains the organic compound of the present invention alone or in combination of two or more.

In the organic electroluminescent device, the organic thin film layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer,

The hole transport layer may contain an organic compound represented by Formula 2 below, alone or in combination of two or more:

[Formula 2]

In the above formula,

R1, R2, R3 and R4 are each independently hydrogen; a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms; Aromatic hydrocarbon having 6 to 60 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of C1~C10 straight chain or branched chain alkyl, C1~C10 alkoxy, halogen, CN, CF ₃ and Si(CH ₃ ) ₃ group energy; or C1~C10 straight-chain or branched-chain alkyl, C1~C10 alkoxy, halogen, CN, CF ₃ and Si(CH ₃ ) ₃ groups, substituted or unsubstituted with one or more selected from the group consisting of S, O, N and a heteroaromatic hydrocarbon group having 5 to 60 carbon atoms containing at least one element selected from the group consisting of Si;

Each of R1, R2, R3 and R4 may be independently bonded to the phenyl group of the basic structure to form an aromatic hydrocarbon or a heteroaromatic hydrocarbon.

The present invention provides a novel organic compound that is used as a host material to improve luminous efficiency and luminous lifetime of an organic light emitting device.

In addition, the present invention provides an organic light emitting device with improved driving voltage, luminous efficiency and luminous lifetime by including the host material as described above.

In addition, the present invention provides an organic light emitting device with further improved driving voltage, device efficiency and lifespan by including the host material and a specific hole transport layer material in combination.

The present invention provides an organic light emitting device characterized in that a compound constituting the organic light emitting device includes tritium in its chemical structure.

In addition, the present invention relates to a novel organic compound represented by the following formula (1):

[Formula 1]

in the above formula

Ar1 and Ar2 are each independently selected from tritium, deuterium, hydrogen, CN, straight or branched chain alkyl having 1 to 40 carbon atoms, alkoxy having 1 to 40 carbon atoms, thioalkyl having 1 to 40 carbon atoms, cycloalkyl having 3 to 40 carbon atoms, Phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl , A pyrazinyl group, a pyrimidinyl group, and an aromatic hydrocarbon group having 6 to 60 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of a quinolinyl group,

tritium, deuterium, hydrogen, CN, straight or branched chain alkyl of 1 to 40 carbon atoms, alkoxy of 1 to 40 carbon atoms, thioalkyl of 1 to 40 carbon atoms, cycloalkyl of 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl , anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, spirobi [fluorene], carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyra Hetero having 5 to 70 carbon atoms, substituted or unsubstituted with one or more selected from the group consisting of zinyl, pyrimidinyl, and quinolinyl, and containing one or more elements selected from the group consisting of S, O, N, and Si It is an aromatic hydrocarbon group,

R1, R2, R3, R4, R5, R6, R7 and R8 are each independently tritium, deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , carbon atoms a straight-chain or branched-chain alkyl group of 1 to 40 carbon atoms, an alkoxy group of 1 to 40 carbon atoms, a thioalkyl group of 1 to 40 carbon atoms, or a cycloalkyl group of 3 to 40 carbon atoms;

tritium, deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , straight or branched chain alkyl of 1 to 40 carbon atoms, alkoxy of 1 to 40 carbon atoms, 1 carbon atom thioalkyl of 3 to 40 carbon atoms, cycloalkyl of 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carba An aromatic hydrocarbon group having 6 to 60 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of zoyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, and quinolinyl,

tritium, deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , straight or branched chain alkyl of 1 to 40 carbon atoms, alkoxy of 1 to 40 carbon atoms, 1 carbon atom thioalkyl of 3 to 40 carbon atoms, cycloalkyl of 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, spirobi[ fluorene], carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl group, and unsubstituted or substituted with one or more selected from the group consisting of S, O, A heteroaromatic hydrocarbon group having 5 to 70 carbon atoms containing at least one element selected from the group consisting of N and Si;

tritium, deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , straight or branched chain alkyl of 1 to 40 carbon atoms, alkoxy of 1 to 40 carbon atoms, 1 carbon atom Phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl, phenanthrenyl substituted or unsubstituted with one or more selected from the group consisting of thioalkyl groups having 3 to 40 carbon atoms and cycloalkyl groups having 3 to 40 carbon atoms At least one selected from the group consisting of pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and pyrimidinyl groups is an amino group substituted with

Specific examples of the organic compound include any one of Compounds 1 to 463 below.

Since the organic compound can be used as a material for a blue host and can improve the performance of an organic light emitting device by mixing with other functional layers, its use is not limited.

The present invention also

In the organic electroluminescent device in which an organic thin film layer composed of one or a plurality of layers including at least a light emitting layer is laminated between a cathode and an anode,

It relates to an organic electroluminescent device characterized in that the light emitting layer contains the organic compound alone or in combination of two or more.

The organic thin film layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer,

The hole transport layer may contain an organic compound represented by Formula 2 below, alone or in combination of two or more:

[Formula 2]

In the above formula,

R1, R2, R3 and R4 are each independently hydrogen; a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms; Aromatic hydrocarbon having 6 to 60 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of C1~C10 straight chain or branched chain alkyl, C1~C10 alkoxy, halogen, CN, CF ₃ and Si(CH ₃ ) ₃ group energy; or C1~C10 straight-chain or branched-chain alkyl, C1~C10 alkoxy, halogen, CN, CF ₃ and Si(CH ₃ ) ₃ groups, substituted or unsubstituted with one or more selected from the group consisting of S, O, N and a heteroaromatic hydrocarbon group having 5 to 60 carbon atoms containing at least one element selected from the group consisting of Si;

Each of R1, R2, R3, and R4 may be independently bonded to a phenyl group of a back bone to form an aromatic hydrocarbon or a heteroaromatic hydrocarbon.

In the above formula, more preferably,

R1, R2, R3 and R4 may each independently be a phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl carbazole or pyrenyl group;

The R1, R2, R3, and R4 may each independently bond to a phenyl group of a basic structure to form naphthalene, anthracene, or phenanthrene.

Specific examples of the organic compound include any one of Compounds 464 to 475 below.

Hereinafter, the organic electroluminescent device of the present invention will be described as an example. However, the content exemplified below does not limit the organic electroluminescent device of the present invention.

In the method of manufacturing an organic electroluminescent device according to the present invention, first, an anode is formed by coating a substrate surface with an anode material in a conventional manner. At this time, the substrate used is preferably a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and water resistance. In addition, as the material for the anode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, may be used.

Next, a hole injection layer (HIL) material is vacuum thermally deposited or spin-coated on the surface of the anode in a conventional manner to form a hole injection layer. Materials for the hole injection layer include copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylamino)triphenylamine (m-MTDATA), and 4,4',4"-tris(3-methylphenyl). Amino) phenoxybenzene (m-MTDAPB), starburst type amines 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), 4,4',4"-tris (N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA) or IDE406 available from Idemitsu is exemplified.

A hole transport layer (HTL) material is vacuum thermally deposited or spin-coated on the surface of the hole injection layer in a conventional manner to form a hole transport layer. At this time, the hole transport layer material is bis (N- (1-naphthyl-n-phenyl)) benzidine (α-NPD), N, N'-di (naphthalen-1-yl) -N, N'-biphenyl Examples include -benzidine (NPB) or N,N'-biphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD); More preferably, the compound of Formula 2 of the present invention may be used.

A light-emitting layer (EML) material is vacuum thermally deposited or spin-coated on the surface of the hole transport layer in a conventional manner to form the light-emitting layer. At this time, examples of the light emitting material used include phosphorescent fluorescent materials, optical whitening agents, laser dyes, organic scintillators, and reagents for fluorescence analysis. Specifically, carbazole-based compounds, phosphine oxide-based compounds, carbazole-based phosphine oxide compounds, bis((3,5-difluoro-4-cyanophenyl)pyridine) iridium picolinate (FCNIrpic), tris( 8-hydroxyquinoline) aluminum (Alq3), polyaromatic compounds such as anthracene, phenanthrene, pyrene, chrysene, perylene, coronene, rubrene and quinacridone, oligophenylene compounds such as quaterphenyl, 1, 4-bis (2-methylstyryl) benzene, 1,4-bis (4-methylstyryl) benzene, 1,4-bis (4-methyl-5-phenyl-2-oxazolyl) benzene, 1,4 -bis(5-phenyl-2-oxazolyl)benzene, 2,5-bis(5-t-butyl-2-benzoxazolyl)thiophene, 1,4-diphenyl-1,3-butadiene, 1, Scintillators for liquid scintillation such as 6-diphenyl-1,3,5-hexatriene and 1,1,4,4-tetraphenyl-1,3-butadiene, metal complexes of auxin derivatives, coumarin pigments, dicyano Methylenepyran pigment, dicyanomethylenethiopyran pigment, polymethine pigment, oxobenzanthracene pigment, xanthene pigment, carbostyril pigment, perylene pigment, oxazine compound, stilbene derivative, spiro compound, oxadiazole compound, etc. can be heard In particular, in the case of a blue organic light emitting device, it may be preferable to use the organic compound represented by Chemical Formula 1 of the present invention as a dopant.

Optionally, an electron blocking layer (EBL) may be further formed between the hole transport layer and the light emitting layer.

An electron transport layer (ETL) material is vacuum thermally deposited or spin-coated on the surface of the light emitting layer in a conventional manner to form an electron transport layer. At this time, the electron transport layer material used is not particularly limited, and preferably tris(8-hydroxyquinolinolato) aluminum (Alq ₃ ) may be used.

Optionally, by additionally forming a hole blocking layer (HBL) between the light emitting layer and the electron transport layer and using a phosphorescent dopant together with the light emitting layer, diffusion of triplet excitons or holes into the electron transport layer can be prevented.

Formation of the hole blocking layer may be carried out by vacuum thermal evaporation and spin coating of the hole blocking layer material in a conventional manner. In the case of the hole blocking layer material, it is not particularly limited, but preferably (8-hydroxyquinolinola To) lithium (Liq), bis(8-hydroxy-2-methylquinolinolnato)-aluminum biphenoxide (BAlq), bathocuproine (BCP), Bphen, and the like can be used.

An electron injection layer (EIL) material is vacuum thermally deposited or spin-coated on the surface of the electron transport layer in a conventional manner to form an electron injection layer. In this case, materials such as LiF, Liq, Li ₂ O, BaO, NaCl, and CsF may be used as the material for the electron injection layer.

A negative electrode is formed by vacuum thermal evaporation of a negative electrode material on the surface of the electron injection layer in a conventional manner.

At this time, the negative electrode material used is lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and the like may be used. In addition, in the case of a top emission organic electroluminescent device, a transparent cathode through which light can pass may be formed using indium tin oxide (ITO) or indium zinc oxide (IZO).

A capping layer (CPL) may be formed on the surface of the negative electrode by the composition for forming a capping layer according to the present invention.

The organic electroluminescent device according to the present invention may be manufactured in the order described above, that is, in the order of anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode, or vice versa, cathode/electron injection layer/ It may be prepared in the order of electron transport layer/light emitting layer/hole transport layer/hole injection layer/anode.

Hereinafter, a method for synthesizing the compound of Formula 1 will be described below as a representative example. However, the synthesis method of the compounds of the present invention is not limited to the methods exemplified below, and the compounds of the present invention may be prepared by methods exemplified below and methods known in the art.

In particular, in the preparation of the following tritium-containing intermediate, this example explains that a new tritium intermediate can be prepared by substituting tritium in an existing intermediate, and the method for preparing the compound of the present invention is illustrated below. method is not limited. In addition, it is obvious that the compound of Formula 1 can also prepare a tritium compound through such a tritium substitution method.

<Synthesis of Compound of Formula 1>

Synthesis of Intermediate-2

1.44 g (10 mmol) of intermediate-1 (naphthalen-2-ol), 98 mg (0.50 mmol) of Pt/C, 5 mL of tritiated water (T ₂ O), 3.0 mL of isopropanol, and 60 mL of cyclonucleic acid are added. After stirring at 140 ° C. for 12 hours in a high-pressure reactor, it is cooled to room temperature. After adding dichloromethane, the layers are separated to obtain an organic layer. After drying with MgSO4, filter. After concentrating the filtrate, isopropanol is added. The resulting solid was filtered and columned to obtain 1.25 g (78%, tritium conversion 79%) of Intermediate-2.

Intermediate-2 MS (FAB): 160 (M ⁺ )

Synthesis of Intermediate-3

Put 1.60 g (10 mmol) of Intermediate-2, 3.93 g (15 mmol) of triphenylphosphine, 0.96 g (6 mmol) of bromine, and 30 mL of acrylonitrile into a 100 ml three-necked round bottom flask. After stirring at 80°C for 18 hours, cool to room temperature. After adding 250 ml of EA and 250 ml of water, the layers were separated to obtain an organic layer. After distillation and column, 1.90 g (86%) of Intermediate-3 was obtained.

Intermediate-3 MS (FAB): 221 (M ⁺ )

Synthesis of Intermediate-5

Add 1.28g (10mmol) of intermediate-4 (naphthalene), 98mg (0.50mmol) of Pt/C, 3.0mL of isopropanol, and 60mL of cyclonucleic acid. After stirring at 140 ° C. for 24 hours under a T ₂ atmosphere in a high-pressure reactor, it is cooled to room temperature. After filtration under reduced pressure, the organic solvent was concentrated and the resulting compound was columned at Hex : EA = 5 : 1 to obtain 1.18 g of Intermediate-5 (91%, 14% tritium conversion).

Intermediate-5 MS (FAB): 130 (M ⁺ )

Synthesis of Intermediate-6

After dissolving 1.30 g (10 mmol) of Intermediate-5 in 30 ml of MC in a 100 ml three-necked round bottom flask, 2.14 g (12 mmol) of NBS was slowly added at 0 degrees. After removing the bath, the temperature was raised to room temperature to complete the reaction after 6 hours, and 250 ml of EA and 250 ml of water were added. The organic layer was extracted, distilled, and columnized to obtain 1.74 g (83%) of Intermediate-6.

Intermediate-6 MS (FAB): 209 (M ⁺ )

Synthesis of Intermediate-8

Add 1.78 g (10 mmol) of intermediate-7 (anthracene), 114 mg (0.50 mmol) of Pt/C, 2 mL of tritiated water (DTO), 3.0 mL of 2-pentanol, and 60 mL of decahydronaphthalene. After stirring at 140 ° C. for 12 hours in a high-pressure reactor, it is cooled to room temperature. After adding dichloromethane, the layers are separated to obtain an organic layer. After drying with MgSO4, filter. After concentrating the filtrate, isopropanol is added. The resulting solid was filtered and columned to obtain 1.25 g (78%, tritium conversion 9%) of Intermediate-8.

Intermediate-8 MS (FAB): 182 (M ⁺ )

Synthesis of Intermediate-9

After dissolving 1.82 g (10 mmol) of Intermediate-8 in 30 ml of MC in a 100 ml three-necked round bottom flask, 2.14 g (12 mmol) of NBS was slowly added at 0 degrees. After removing the bath, the temperature was raised to room temperature to complete the reaction after 6 hours, and 250 ml of EA and 250 ml of water were added. The organic layer was extracted, distilled, and columnized to obtain 2.21 g (85%) of Intermediate-9.

Intermediate-9 MS (FAB): 260 (M ⁺ )

Synthesis of Intermediate-11

In a 100ml three-necked round bottom flask, 2.07 g (10 mmol) of intermediate-10 (2-bromonaphthalene), 668 mg (2.4 mmol) of silver carbonate, 1.63 g (6.1 mmol) of cyclohexyldiphenylphosphine, 1.67 g (12 mmol) of potassium carbonate, Add 5.34 g (0.24 mol) of tritiated water (T ₂ O) and 10 mL of toluene. After stirring at 120°C for 12 hours, cool to room temperature. A saturated aqueous ammonia chloride solution was added to terminate the reaction, and after adding water and dichloromethane, the layers were separated to obtain an organic layer. After drying with Na ₂ SO ₄ , it is filtered. After concentrating the filtrate, isopropanol is added. The resulting solid was filtered and columned to obtain 1.94 g (91%, tritium conversion 43%) of Intermediate-11.

Intermediate-11 MS (FAB): 213 (M ⁺ )

Synthesis of Intermediate-12

2.09 g (10 mmol) of Intermediate-6 was dissolved in 40 ml of anhydrous THF under nitrogen, the temperature of the reaction was lowered to -78 ° C, 4 ml of 2.5M n-BuLi was slowly added dropwise, and the reaction was stirred at 0 ° C for 1 hour. . Thereafter, the temperature of the reactant was lowered to -78° C., and 12.47 g (12 mmol) of trimethyl borate was added dropwise, followed by stirring at room temperature for 12 hours. When the reaction was completed, a 2N-HCl aqueous solution was added, stirred for 30 minutes, and then extracted with ether.

After removing water in the organic layer with anhydrous MgSO ₄ , filtering under reduced pressure, and concentrating the organic solvent, the resulting compound was columned with Hex : EA = 5 : 1 to obtain 1.48 g (85%) of Intermediate-12.

Intermediate-12 MS (FAB): 174 (M ⁺ )

Synthesis of Intermediate-13

2.21 g (10 mmol) of Intermediate-3 was dissolved in 40 ml of anhydrous THF under nitrogen, the temperature of the reaction was lowered to -78 ° C, 4 ml of 2.5M n-BuLi was slowly added dropwise, and the reaction was stirred at 0 ° C for 1 hour. . Thereafter, the temperature of the reactant was lowered to -78° C., and 12.47 g (12 mmol) of trimethyl borate was added dropwise, followed by stirring at room temperature for 12 hours. When the reaction was completed, a 2N-HCl aqueous solution was added, stirred for 30 minutes, and then extracted with ether.

After removing water in the organic layer with anhydrous MgSO ₄ , filtering under reduced pressure, and concentrating the organic solvent, the resulting compound was columned with Hex : EA = 5 : 1 to obtain 1.54 g (83%) of Intermediate-13.

Intermediate-13 MS (FAB): 186 (M ⁺ )

Synthesis of Intermediate-15

2.57g (10mmol) of Intermediate-14 (9-bromophenanthrene), 98mg (0.50mmol) of Pt/C, 3.0mL of isopropanol, and 60mL of cyclohexane were added. After stirring at 140 ° C. for 24 hours under a T ₂ atmosphere in a high-pressure reactor, it is cooled to room temperature. After filtration under reduced pressure, the organic solvent was concentrated and the resulting compound was columned at Hex: EA = 5: 1 to obtain 2.33 g of Intermediate-15 (90%, 11% tritium conversion).

Intermediate-15 MS (FAB): 259 (M ⁺ )

Synthesis of Intermediate-16

2.59g (10mmol) of Intermediate-15 was dissolved in 40ml of anhydrous THF under nitrogen, the temperature of the reaction was lowered to -78°C, 4ml of 2.5M n-BuLi was slowly added dropwise, and then the reaction was stirred at 0°C for 1 hour. . Thereafter, the temperature of the reactant was lowered to -78° C., and 12.47 g (12 mmol) of trimethyl borate was added dropwise, followed by stirring at room temperature for 12 hours. When the reaction was completed, a 2N-HCl aqueous solution was added, stirred for 30 minutes, and then extracted with ether.

After removing water in the organic layer with anhydrous MgSO ₄ , filtering under reduced pressure, and concentrating the organic solvent, the resulting compound was columned with Hex:EA = 4:1 to obtain 1.88 g (84%) of Intermediate-16.

Intermediate-16 MS (FAB): 224 (M ⁺ )

Synthesis of Intermediate-18

After injecting 1.86 g (10 mmol) of Intermediate-13 and 2.83 g (10 mmol) of Intermediate-17 (1-bromo-4-iodobenzene) under nitrogen and dissolving them in 30 ml of toluene, 0.58 g (0.5 mmol) of Pd (PPh ₃ ) ₄ and 2M K ₂ CO ₃ 15ml (30mmol) was added to each and then refluxed for 24 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, MC layer was extracted by adding 150 ml of MC and 150 ml of H ₂ O, dried with anhydrous MgSO ₄ , concentrated, and Hex: EA = 5: 1 column to obtain Intermediate-18 2.50 (84%) was obtained.

Intermediate-18 MS (FAB): 297 (M ⁺ )

Synthesis of Intermediate-19

After injecting 1.72 g (10 mmol) of Intermediate-12 and 2.83 g (10 mmol) of Intermediate-17 (1-bromo-4-iodobenzene) under nitrogen and dissolving them in 30 ml of toluene, 0.58 g (0.5 mmol) of Pd (PPh ₃ ) ₄ and 2M K ₂ CO ₃ 15ml (30mmol) was added to each and then refluxed for 24 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, MC layer was extracted by adding 150 ml of MC and 150 ml of H ₂ O, dried over anhydrous MgSO ₄ , concentrated, and Hex: EA = 5: 1 column to obtain Intermediate-19 2.31 (81%) was obtained.

Intermediate-19 MS (FAB): 285 (M ⁺ )

Synthesis of Intermediate-21

After injecting 2.24 g (10 mmol) of Intermediate-16 and 2.83 g (10 mmol) of Intermediate-20 (1-bromo-3-iodobenzene) under nitrogen and dissolving them in 30 ml of toluene, 0.58 g (0.5 mmol) of Pd (PPh ₃ ) ₄ and 2M K ₂ CO ₃ 15ml (30mmol) was added to each and then refluxed for 24 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, MC layer was extracted by adding 150 ml of MC and 150 ml of H ₂ O, dried with anhydrous MgSO ₄ , concentrated, and Hex: EA = 5: 1 column to obtain Intermediate-21 2.65 (79%) was obtained.

Intermediate-21 MS (FAB): 335 (M ⁺ )

Synthesis of Intermediate-23

After injecting 3.36 g (10 mmol) of Intermediate-22 (9,10-dibromoanthracene) and 1.86 g (10 mmol) of Intermediate-13 under nitrogen and dissolving them in 40 ml of toluene, Pd (PPh ₃ ) ₄ 0.58 g (0.5 mmol) and 2M K ₂ CO ₃ 15ml (30mmol) was added to each and then refluxed for 24 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, MC layer was extracted by adding 200 ml of MC and 200 ml of H ₂ O, dried over anhydrous MgSO ₄ , concentrated, and Hex: EA = 4: 1 column to obtain Intermediate-23 2.54 (64%).

Intermediate-23 MS (FAB): 397 (M ⁺ )

Synthesis of Intermediate-24

After injecting 3.36 g (10 mmol) of Intermediate-22 (9,10-dibromoanthracene) and 1.74 g (10 mmol) of Intermediate-12 under nitrogen and dissolving them in 45 ml of toluene, Pd (PPh ₃ ) ₄ 0.58 g (0.5 mmol) and 2M K ₂ CO ₃ 15ml (30mmol) was added to each and then refluxed for 24 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, and the MC layer was extracted by adding 200 ml of MC and 200 ml of H ₂ O, dried over anhydrous MgSO ₄ , concentrated, and columned with Hex: MC = 3: 1 to obtain Intermediate-24 2.39 (62%).

Intermediate-24 MS (FAB): 385 (M ⁺ )

Synthesis of Intermediate-25

After injecting 3.36 g (10 mmol) of Intermediate-22 (9,10-dibromoanthracene) and 2.24 g (10 mmol) of Intermediate-16 under nitrogen and dissolving them in 45 ml of toluene, Pd (PPh ₃ ) ₄ 0.58 g (0.5 mmol) and 2M K ₂ CO ₃ 15ml (30mmol) was added to each and then refluxed for 24 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, and the MC layer was extracted by adding 200 ml of MC and 200 ml of H ₂ O, dried over anhydrous MgSO ₄ , concentrated, and columned with Hex: MC = 3: 1 to obtain Intermediate-25 2.61 (60%) was obtained.

Intermediate-25 MS (FAB): 435 (M ⁺ )

Synthesis of Intermediate-26

3.97g (10mmol) of Intermediate-23 was dissolved in 40ml of anhydrous THF under nitrogen, the temperature of the reaction was lowered to -78°C, 4ml of 2.5M n-BuLi was slowly added dropwise, and then the reaction was stirred at 0°C for 1 hour. . Thereafter, the temperature of the reactant was lowered to -78° C., and 12.47 g (12 mmol) of trimethyl borate was added dropwise, followed by stirring at room temperature for 12 hours. When the reaction was completed, a 2N-HCl aqueous solution was added, stirred for 30 minutes, and then extracted with ether.

After removing water in the organic layer with anhydrous MgSO ₄ , filtering under reduced pressure, and concentrating the organic solvent, the resulting compound was columned with Hex : MC = 3 : 1 to obtain 3.22 g (89%) of Intermediate-26.

Intermediate-26 MS (FAB): 362 (M ⁺ )

Synthesis of Intermediate-27

3.85 g (10 mmol) of Intermediate-24 was dissolved in 40 ml of anhydrous THF under nitrogen, the temperature of the reaction was lowered to -78 ° C, 4 ml of 2.5 M n-BuLi was slowly added dropwise, and the reaction was stirred at 0 ° C for 1 hour. . Thereafter, the temperature of the reactant was lowered to -78° C., and 12.47 g (12 mmol) of trimethyl borate was added dropwise, followed by stirring at room temperature for 12 hours. When the reaction was completed, a 2N-HCl aqueous solution was added, stirred for 30 minutes, and then extracted with ether.

After removing water in the organic layer with anhydrous MgSO ₄ , filtering under reduced pressure, and concentrating the organic solvent, the resulting compound was columned with Hex:MC = 3:1 to obtain 3.01 g (86%) of Intermediate-27.

Intermediate-27 MS (FAB): 350 (M ⁺ )

Synthesis of Intermediate-28

4.35 g (10 mmol) of Intermediate-25 was dissolved in 45 ml of anhydrous THF under nitrogen, the temperature of the reaction was lowered to -78 ° C, 4 ml of 2.5 M n-BuLi was slowly added dropwise, and the reaction was stirred at 0 ° C for 1 hour. . Thereafter, the temperature of the reactant was lowered to -78° C., and 12.47 g (12 mmol) of trimethyl borate was added dropwise, followed by stirring at room temperature for 12 hours. When the reaction was completed, a 2N-HCl aqueous solution was added, stirred for 30 minutes, and then extracted with ether.

After removing water from the organic layer with anhydrous MgSO ₄ , filtering under reduced pressure, and concentrating the organic solvent, the resulting compound was columned with Hex:MC = 3:1 to obtain 3.32 g (83%) of Intermediate-28.

Intermediate-28 MS (FAB): 400 (M ⁺ )

Synthesis of Intermediate-29

After injecting 2.24 g (10 mmol) of Intermediate-16 and 2.83 g (10 mmol) of Intermediate-17 (1-bromo-4-iodobenzene) under nitrogen and dissolving in 40 ml of toluene, 0.58 g (0.5 mmol) of Pd (PPh ₃ ) ₄ and 2M K ₂ CO ₃ 15ml (30mmol) was added to each and then refluxed for 24 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, and the MC layer was extracted by adding 150 ml of MC and 150 ml of H ₂ O, dried over anhydrous MgSO ₄ , concentrated, and columned with Hex: MC = 4: 1 to obtain Intermediate-29 2.61 (78%) was obtained.

Intermediate-29 MS (FAB): 335 (M ⁺ )

Synthesis of Intermediate-31

After injecting 2.24g (10mmol) of Intermediate-16 and 2.86g (10mmol) of Intermediate-30 (1,4-dibromonaphthalene) under nitrogen and dissolving in 40ml of toluene, Pd (PPh ₃ ) ₄ 0.58g (0.5mmol) and 2M K ₂ CO ₃ 15ml (30mmol) was added to each and then refluxed for 24 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, and the MC layer was extracted by adding 200 ml of MC and 200 ml of H ₂ O, dried over anhydrous MgSO ₄ , concentrated, and columned with Hex: MC = 3: 1 to obtain Intermediate-31 2.35 (61%).

Intermediate-31 MS (FAB): 385 (M ⁺ )

Synthesis of Intermediate-32

After injecting 2.86 g (10 mmol) of Intermediate-30 (1,4-dibromonaphthalene) and 1.74 g (10 mmol) of Intermediate-12 under nitrogen and dissolving them in 40 ml of toluene, Pd (PPh ₃ ) ₄ 0.58 g (0.5 mmol) and 2M K ₂ CO ₃ 15ml (30mmol) was added to each and then refluxed for 24 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, 150 ml of MC and 150 ml of H ₂ O were added to extract the MC layer, dried over anhydrous MgSO ₄ , concentrated, and Hex: EA = 4: 1 column was used to obtain Intermediate-32 1.94 (58%) was obtained.

Intermediate-32 MS (FAB): 335 (M ⁺ )

Synthesis of Intermediate-33

3.85 g (10 mmol) of Intermediate-31 was dissolved in 40 ml of anhydrous THF under nitrogen, the temperature of the reaction was lowered to -78 ° C, 4 ml of 2.5 M n-BuLi was slowly added dropwise, and the reaction was stirred at 0 ° C for 1 hour. . Thereafter, the temperature of the reactant was lowered to -78° C., and 12.47 g (12 mmol) of trimethyl borate was added dropwise, followed by stirring at room temperature for 12 hours. When the reaction was completed, a 2N-HCl aqueous solution was added, stirred for 30 minutes, and then extracted with ether.

After removing water in the organic layer with anhydrous MgSO ₄ , filtering under reduced pressure, and concentrating the organic solvent, the resulting compound was columned with Hex:MC = 3:1 to obtain 2.98 g (85%) of Intermediate-33.

Intermediate-33 MS (FAB): 350 (M ⁺ )

Synthesis of Intermediate-34

3.35 g (10 mmol) of Intermediate-32 was dissolved in 40 ml of anhydrous THF under nitrogen, the temperature of the reaction was lowered to -78 ° C, 4 ml of 2.5 M n-BuLi was slowly added dropwise, and the reaction was stirred at 0 ° C for 1 hour. . Thereafter, the temperature of the reactant was lowered to -78° C., and 12.47 g (12 mmol) of trimethyl borate was added dropwise, followed by stirring at room temperature for 12 hours. When the reaction was completed, a 2N-HCl aqueous solution was added, stirred for 30 minutes, and then extracted with ether.

After removing water in the organic layer with anhydrous MgSO ₄ , filtering under reduced pressure, and concentrating the organic solvent, the resulting compound was columned with Hex:MC = 3:1 to obtain 2.58 g (86%) of Intermediate-34.

Intermediate-34 MS (FAB): 300 (M ⁺ )

Synthesis of Intermediate-36

After injecting 1.86g (10mmol) of Intermediate-13 and 2.86g (10mmol) of Intermediate-35 (1,2-dibromonaphthalene) under nitrogen and dissolving in 40ml of toluene, Pd (PPh ₃ ) ₄ 0.58g (0.5mmol) and 2M K ₂ CO ₃ 15ml (30mmol) was added to each and then refluxed for 24 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, and the MC layer was extracted by adding 150 ml of MC and 150 ml of H ₂ O, dried over anhydrous MgSO ₄ , concentrated, and columned with Hex: MC = 4: 1 to obtain intermediate-36 2.26 g (65%) was obtained.

Intermediate-36 MS (FAB): 347 (M ⁺ )

Synthesis of Intermediate-37

After injecting 2.86 g (10 mmol) of Intermediate-35 (1,2-dibromonaphthalene) and 2.24 g (10 mmol) of Intermediate-16 under nitrogen and dissolving them in 50 ml of toluene, Pd (PPh ₃ ) ₄ 0.58 g (0.5 mmol) and 2M K ₂ CO ₃ 15ml (30mmol) was added to each and then refluxed for 24 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, and the MC layer was extracted by adding 200 ml of MC and 200 ml of H ₂ O, dried over anhydrous MgSO ₄ , concentrated, and columned with Hex: MC = 3: 1 to obtain Intermediate-37 2.35 g (61%) was obtained.

Intermediate-37 MS (FAB): 385 (M ⁺ )

Synthesis of Compound-10

After injecting 3.35 g (10 mmol) of Intermediate-29 and 3.50 g (10 mmol) of Intermediate-27 under nitrogen and dissolving in 50 ml of toluene, 0.58 g (0.5 mmol) of Pd (PPh ₃ ) ₄ and 15 ml (30 mmol) of 2M K ₂ CO ₃ were added and refluxed for 24 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, and the MC layer was extracted by adding 200 ml of MC and 200 ml of H ₂ O, dried over anhydrous MgSO ₄ , concentrated, and columned with Hex : MC = 3 : 1 to obtain Compound-10 4.71 g (84%) was obtained.

¹ H NMR (DMSO, 300 Hz): δ (ppm) = 9.15-9.05 (d, 1H), 9.01-8.92 (d, 1H), 8.89-8.81 (d, 1H), 8.69-8.51 (d, 1H), 8.35-8.13(m, 6H), 8.10-7.97(m, 2H), 7.93-7.87(m, 1H), 7.84-7.55(m, 5H), 7.52-7.01(m, 10H)

MS(FAB): 560(M+)

Synthesis of Compound-59

After injecting 3.35 g (10 mmol) of Intermediate-21 and 4.00 g (10 mmol) of Intermediate-28 under nitrogen and dissolving in 50 ml of toluene, 0.58 g (0.5 mmol) of Pd (PPh ₃ ) ₄ and 15 ml (30 mmol) of 2M K ₂ CO ₃ were added and refluxed for 24 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, and the MC layer was extracted by adding 200 ml of MC and 200 ml of H ₂ O, dried over anhydrous MgSO ₄ , concentrated, and columned with Hex: MC = 3: 1 to obtain Compound-59 4.95 g (81%) was obtained.

¹ H NMR (DMSO, 300 Hz): δ (ppm) = 9.14-9.05 (m, 2H), 8.95-8.81 (m, 2H), 8.35-8.13 (m, 6H), 8.10-7.97 (m, 2H), 7.93-7.87(m, 3H), 7.84-7.55(m, 11H), 7.52-7.09(m, 4H)

MS(FAB): 610(M+)

Synthesis of Compound-118

After injecting 2.97g (10mmol) of Intermediate-18 and 3.50g (10mmol) of Intermediate-27 under nitrogen and dissolving in 50ml of toluene, 0.58g (0.5mmol) of Pd (PPh ₃ ) ₄ and 15ml (30mmol) of 2M K ₂ CO ₃ were added and refluxed for 24 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, and the MC layer was extracted by adding 200 ml of MC and 200 ml of H ₂ O, dried over anhydrous MgSO ₄ , concentrated, and columned with Hex : MC = 3 : 1 to obtain Compound-118 4.29 g (82%) was obtained.

¹ H NMR (DMSO, 300 Hz): δ (ppm) = 8.29-8.18 (d, 1H), 8.09-8.02 (d, 1H), 7.98-7.73 (m, 8H), 7.69-7.57 (m, 6H), 7.55-7.41(m, 2H), 7.37-7.13(m, 8H)

MS(FAB): 522(M+)

Synthesis of Compound-242

After injecting 3.47g (10mmol) of Intermediate-36 and 3.62g (10mmol) of Intermediate-26 under nitrogen and dissolving them in 50ml of toluene, 0.58g (0.5mmol) of Pd (PPh ₃ ) ₄ and 15ml (30mmol) of 2M K ₂ CO ₃ were added and refluxed for 24 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, and the MC layer was extracted by adding 200 ml of MC and 200 ml of H ₂ O, dried over anhydrous MgSO ₄ , concentrated, and columned with Hex: MC = 2: 1 to obtain Compound-242 4.74 g (81%) was obtained.

¹ H NMR (DMSO, 300 Hz): δ (ppm) = 8.29-8.18 (m, 2H), 8.15-8.02 (m, 2H), 7.98-7.73 (m, 10H), 7.67-7.45 (m, 7H), 7.41-7.04(m, 7H)

MS(FAB): 584(M+)

Synthesis of Compound-279

After injecting 3.85 g (10 mmol) of Intermediate-37 and 4.00 g (10 mmol) of Intermediate-28 under nitrogen and dissolving them in 50 ml of toluene, 0.58 g (0.5 mmol) of Pd (PPh ₃ ) ₄ and 15 ml (30 mmol) of 2M K ₂ CO ₃ were added and refluxed for 24 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, and the MC layer was extracted by adding 200 ml of MC and 200 ml of H ₂ O, dried over anhydrous MgSO ₄ , concentrated, and columned with Hex: MC = 2: 1 to obtain Compound-279 5.15 g (78%) was obtained.

¹ H NMR (DMSO, 300 Hz): δ (ppm) = 9.15-9.05 (m, 2H), 9.01-8.81 (m, 4H), 8.45-8.09 (m, 7H), 8.07-7.97 (m, 2H), 7.93-7.87(m, 2H), 7.84-7.51(m, 10H), 7.48-7.04(m, 5H)

MS(FAB): 660(M+)

Synthesis of Compound-358

After injecting 2.97 g (10 mmol) of Intermediate-38 (4-bromonaphtho [2,3-b] benzofuran) and 3.50 g (10 mmol) of Intermediate-27 under nitrogen and dissolving in 50 ml of toluene, Pd (PPh ₃ ) ₄ 0.58 g ( 0.5mmol) and 2M K ₂ CO ₃ 15ml (30mmol), respectively, and then refluxed for 24 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, and the MC layer was extracted by adding 200 ml of MC and 200 ml of H ₂ O, dried over anhydrous MgSO ₄ , concentrated, and columned with Hex: MC = 2: 1 to obtain Compound-358 4.13 g (79%) was obtained.

¹ H NMR (DMSO, 300 Hz): δ (ppm) = 8.39-8.32 (d, 1H), 8.25-8.13 (m, 2H), 8.10-7.93 (m, 3H), 7.84-7.58 (m, 8H), 7.55-7.14(m, 5H), 7.11-6.85(m, 5H)

MS(FAB): 522(M+)

Synthesis of Compound-434

After injecting 3.47g (10mmol) of Intermediate-39 (6-bromodinaphtho[1,2-b:1',2'-d]furan) and 3.50g (10mmol) of Intermediate-27 under nitrogen and dissolving in 50ml of toluene, Pd (PPh ₃ ) ₄ 0.58g (0.5mmol) and 2M K ₂ CO ₃ 15ml (30mmol) were added, respectively, and then refluxed for 24 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, and the MC layer was extracted by adding 200 ml of MC and 200 ml of H ₂ O, dried over anhydrous MgSO ₄ , concentrated, and columned with Hex: MC = 2: 1 to obtain Compound-434 4.35 g (76%) was obtained.

¹ H NMR (DMSO, 300 Hz): δ (ppm) = 8.41-8.32 (d, 1H), 8.26-8.13 (m, 2H), 8.10-7.93 (m, 3H), 7.88-7.51 (m, 10H), 7.48-7.14(m, 5H), 7.11-6.89(m, 5H)

MS(FAB): 572(M+)

<Synthesis of Compound of Formula 2>

Synthesis of Intermediate-38

[1,1'-biphenyl] -4-amine 1.69g (10mmol) and 4-iodo-1,1':4',1''-terphenyl 3.56g (10mmol) were injected under nitrogen, and toluene 50ml After dissolving in, Pd ₂ dba ₃ 0.18g (0.2mmol), 1M t-Bu _3P 0.4ml (0.4mmol), and t-BuONa 2.88g (30mmol) were added, respectively, and then refluxed for 8 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with 200 ml of toluene and 200 ml of H ₂ O, and a small amount of water in the organic layer was removed with anhydrous MgSO ₄ . After filtration under reduced pressure, the organic solvent was concentrated and the resulting compound was Hex : EA = 4: 1 to obtain 3.02 g (76%) of Intermediate-38.

Intermediate-38 MS (FAB): 397 (M ⁺ )

Synthesis of Intermediate-39

Inject 3.21 g (10 mmol) of di([1,1'-biphenyl]-4-yl)amine and 3.59 g (10 mmol) of 4-bromo-4'-iodo-1,1'-biphenyl under nitrogen. After dissolving in 60 ml of toluene, 0.18 g (0.2 mmol) of Pd ₂ dba _{3 ,} 0.4 ml (0.4 mmol) of 1M t-Bu ₃ P, and 2.88 g (30 mmol) of t-BuONa were added, respectively, and then refluxed for 8 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with 200 ml of toluene and 200 ml of H ₂ O, and a small amount of water in the organic layer was removed with anhydrous MgSO ₄ . After filtration under reduced pressure, the organic solvent was concentrated and the resulting compound was Hex : EA = 3: 1 to obtain 3.98 g (72%) of Intermediate-39.

Intermediate-39 MS (FAB): 552 (M ⁺ )

Synthesis of Intermediate-40

After injecting 0.93g (10mmol) of aniline and 3.56g (10mmol) of 4-iodo-1,1':4',1''-terphenyl under nitrogen and dissolving in 50ml of toluene, Pd ₂ dba ₃ 0.18g (0.2 mmol), 0.4 ml (0.4 mmol) of 1M t-Bu ₃ P, and 2.88 g (30 mmol) of t-BuONa, respectively, and then refluxed for 8 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with 200 ml of toluene and 200 ml of H ₂ O, and a small amount of water in the organic layer was removed with anhydrous MgSO ₄ . After filtration under reduced pressure, the organic solvent was concentrated and the resulting compound was Hex : EA = 5: 1 to obtain 2.38g (74%) of Intermediate-40.

Intermediate-40 MS (FAB): 321 (M ⁺ )

Synthesis of Intermediate-41

After injecting 0.93g (10mmol) of aniline and 2.80g (10mmol) of 4-iodo-1,1'-biphenyl under nitrogen and dissolving them in 50ml of toluene, Pd ₂ dba ₃ 0.18g (0.2mmol), 1M t-Bu 0.4ml (0.4mmol) of _3P and 2.88g (30mmol) of t-BuONa were added, respectively, and then refluxed for 8 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with 200 ml of toluene and 200 ml of H ₂ O, and a small amount of water in the organic layer was removed with anhydrous MgSO ₄ . After filtration under reduced pressure, the organic solvent was concentrated and the resulting compound was Hex : EA = 5: 1 to obtain 1.99g (81%) of Intermediate-41.

Intermediate-41 MS (FAB): 245 (M ⁺ )

Synthesis of Intermediate-42

After injecting 2.45 g (10 mmol) of Intermediate-40 and 3.59 g (10 mmol) of 4-bromo-4'-iodo-1,1'-biphenyl under nitrogen and dissolving in 60 ml of toluene, Pd ₂ dba ₃ 0.18 g ( 0.2 mmol), 0.4 ml (0.4 mmol) of 1M t-Bu ₃ P, and 2.88 g (30 mmol) of t-BuONa, respectively, and then refluxed for 8 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with 200 ml of toluene and 200 ml of H ₂ O, and a small amount of water in the organic layer was removed with anhydrous MgSO ₄ . After filtration under reduced pressure, the organic solvent was concentrated and the resulting compound was Hex : EA = 4: 1 to obtain 3.57 g (75%) of Intermediate-42.

Intermediate-42 MS (FAB): 476 (M ⁺ )

Synthesis of Compound-464

After injecting 5.53 g (10 mmol) of Intermediate-39 and 3.98 g (10 mmol) of Intermediate-38 under nitrogen and dissolving them in 80 ml of toluene, 0.18 g (0.2 mmol) of Pd ₂ dba ₃ and 0.4 ml (0.4 mmol) of 1M t-Bu ₃ P were added. ) and 2.88 g (30 mmol) of t-BuONa, respectively, and then refluxed for 8 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted using 250 ml of toluene and 250 ml of H ₂ O, and a small amount of water in the organic layer was removed with anhydrous MgSO ₄ . After filtration under reduced pressure, the organic solvent was concentrated and the resulting compound was Hex : EA = 3: 1 to obtain 6.69 g (77%) of Compound-464.

Compound-464 MS (FAB): 869 (M ⁺ )

Synthesis of Compound-466

After injecting 5.53g (10mmol) of Intermediate-39 and 3.21g (10mmol) of Intermediate-40 under nitrogen and dissolving them in 70ml of toluene, 0.18g (0.2mmol) of Pd ₂ dba ₃ and 0.4ml (0.4mmol) of 1M t-Bu ₃ P ) and 2.88 g (30 mmol) of t-BuONa, respectively, and then refluxed for 8 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted using 250 ml of toluene and 250 ml of H ₂ O, and a small amount of water in the organic layer was removed with anhydrous MgSO ₄ . After filtration under reduced pressure, the organic solvent was concentrated and the resulting compound was Hex : EA = 3: 1 to obtain 5.95 g (75%) of Compound-466.

Compound-466 MS (FAB): 793 (M ⁺ )

Synthesis of Compound-475

After injecting 4.76 g (10 mmol) of Intermediate-42 and 3.21 g (10 mmol) of Intermediate-40 under nitrogen and dissolving in 60 ml of toluene, Pd ₂ dba ₃ 0.18 g (0.2 mmol), 1M t-Bu ₃ P 0.4 ml (0.4 mmol) ) and 2.88 g (30 mmol) of t-BuONa, respectively, and then refluxed for 8 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with 200 ml of toluene and 200 ml of H ₂ O, and a small amount of water in the organic layer was removed with anhydrous MgSO ₄ . After filtration under reduced pressure, the organic solvent was concentrated and the resulting compound was Hex : EA = 4: 1 to obtain 5.59 g (78%) of Compound-475.

Compound-475 MS (FAB): 716 (M ⁺ )

The compounds of Formula 2 are known compounds, and methods disclosed in known literature may be used for their synthesis.

Hereinafter, the present invention will be described in more detail through examples and experimental examples. Since these Examples and Experimental Examples are only for exemplifying the present invention, the scope of the present invention is not limited to these Examples and Experimental Examples.

<Manufacture of organic light emitting device>

Example 1

An anode was formed with ITO on the substrate on which the reflective layer was formed, and the surface was treated with N ₂ plasma or UV-Ozone. HAT-CN was deposited thereon to a thickness of 10 nm as a hole injection layer (HIL). Subsequently, NPD was deposited to a thickness of 120 nm as a hole transport layer (HTL). 2,5,8,11-Tetra-butyl-Perylene (t-Bu- Perylene) was doped by about 5%. Anthracene derivative and LiQ were mixed 1:1 thereon to deposit an electron transport layer (ETL) to a thickness of 30 nm, and LiQ was deposited thereon to a thickness of 10 nm as an electron injection layer (EIL). Thereafter, a mixture of magnesium and silver (Ag) in a ratio of 9:1 was deposited to a thickness of 15 nm as a cathode, and N4,N4′-bis[4-[bis(3-methylphenyl) Amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD) was deposited to a thickness of 65 nm. An organic light emitting device was manufactured by bonding a seal cap containing a moisture absorbent with a UV curable adhesive thereon to protect the organic light emitting device from O ₂ or moisture in the air.

Examples 2 to 15

In Example 1, instead of Compound 10 of Formula 1 as a host of blue EML, Formulas 31, 59, 77, 106, 118, 159, 203, 242, 279, 301, 334, 358, 434 and 454 of Formula 1 The organic light emitting devices of Examples 2 to 15 were prepared in the same manner as in Example 1 except for using the compound.

Example 16

An anode was formed with ITO on the substrate on which the reflective layer was formed, and the surface was treated with N ₂ plasma or UV-Ozone. HAT-CN was deposited thereon to a thickness of 10 nm as a hole injection layer (HIL). Subsequently, as a hole transport layer (HTL), compound 464 as a compound of Formula 2 was deposited to a thickness of 120 nm. 2,5,8,11-Tetra-butyl-Perylene (t-Bu- Perylene) was doped by about 5%. Anthracene derivative and LiQ were mixed 1:1 thereon to deposit an electron transport layer (ETL) to a thickness of 30 nm, and LiQ was deposited thereon to a thickness of 10 nm as an electron injection layer (EIL). Thereafter, a mixture of magnesium and silver (Ag) in a ratio of 9:1 was deposited to a thickness of 15 nm as a cathode, and N4,N4′-bis[4-[bis(3-methylphenyl) Amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD) was deposited to a thickness of 65 nm. An organic light emitting device was manufactured by bonding a seal cap containing a moisture absorbent with a UV curable adhesive thereon to protect the organic light emitting device from O ₂ or moisture in the air.

Examples 17 to 30

In Example 16, instead of Compound 10 of Formula 1 as a host of blue EML, Formulas 31, 59, 77, 106, 118, 159, 203, 242, 279, 301, 334, 358, 434 and 454 of Formula 1, respectively Organic electroluminescent devices of Examples 17 to 30 were prepared in the same manner as in Example 16, except that the compound was used.

Example 31

An anode was formed with ITO on the substrate on which the reflective layer was formed, and the surface was treated with N ₂ plasma or UV-Ozone. HAT-CN was deposited thereon to a thickness of 10 nm as a hole injection layer (HIL). Subsequently, as a hole transport layer (HTL), compound 466 as a compound of Formula 2 was deposited to a thickness of 120 nm. 2,5,8,11-Tetra-butyl-Perylene (t-Bu- Perylene) was doped by about 5%. Anthracene derivative and LiQ were mixed 1:1 thereon to deposit an electron transport layer (ETL) to a thickness of 30 nm, and LiQ was deposited thereon to a thickness of 10 nm as an electron injection layer (EIL). Thereafter, a mixture of magnesium and silver (Ag) in a ratio of 9:1 was deposited to a thickness of 15 nm as a cathode, and N4,N4′-bis[4-[bis(3-methylphenyl) Amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD) was deposited to a thickness of 65 nm. An organic light emitting device was manufactured by bonding a seal cap containing a moisture absorbent with a UV curable adhesive thereon to protect the organic light emitting device from O ₂ or moisture in the air.

Example 32

An anode was formed with ITO on the substrate on which the reflective layer was formed, and the surface was treated with N ₂ plasma or UV-Ozone. HAT-CN was deposited thereon to a thickness of 10 nm as a hole injection layer (HIL). Subsequently, as a hole transport layer (HTL), compound 475 as a compound of Formula 2 was deposited to a thickness of 120 nm. 2,5,8,11-Tetra-butyl-Perylene (t-Bu- Perylene) was doped by about 5%. Anthracene derivative and LiQ were mixed 1:1 thereon to deposit an electron transport layer (ETL) to a thickness of 30 nm, and LiQ was deposited thereon to a thickness of 10 nm as an electron injection layer (EIL). Thereafter, a mixture of magnesium and silver (Ag) in a ratio of 9:1 was deposited to a thickness of 15 nm as a cathode, and N4,N4′-bis[4-[bis(3-methylphenyl) Amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD) was deposited to a thickness of 65 nm. An organic light emitting device was manufactured by bonding a seal cap containing a moisture absorbent with a UV curable adhesive thereon to protect the organic light emitting device from O ₂ or moisture in the air.

Comparative Example 1

An organic light emitting device was manufactured in the same manner as in Example 1, except that 9,10-bis(2-naphthyl)anthracene (ADN) was used as the blue EML host for the light emitting layer (EML).

Comparative Example 2

An organic light emitting device was manufactured in the same manner as in Example 16, except that 9,10-bis(2-naphthyl)anthracene (ADN) was used as the blue EML host for the light emitting layer (EML).

The compounds used in Examples 1 to 30, 31 and 32 and Comparative Examples 1 and 2 are shown below.

Test Example: Characteristic evaluation of organic light emitting device

1. Evaluation of characteristics of organic light emitting devices of Examples 1 to 15 and Comparative Example 1

The characteristics of the organic light emitting devices prepared in Examples 1 to 15 and Comparative Example 1 were measured at a current density of 10 mA/cm ² , and the results are shown in Table 1 below.

Voltage
(V) Efficiency
(Cd/A) CIE_x CIE_y T ₉₅ (hours) Example 1 3.6 6.5 0.135 0.057 168 Example 2 3.5 6.2 0.136 0.054 156 Example 3 3.7 6.7 0.135 0.059 152 Example 4 3.8 7.0 0.135 0.059 165 Example 5 3.6 6.1 0.137 0.053 173 Example 6 3.7 6.6 0.135 0.056 151 Example 7 3.5 6.2 0.136 0.055 165 Example 8 3.7 6.5 0.136 0.054 171 Example 9 3.6 6.4 0.136 0.055 174 Example 10 3.7 6.5 0.135 0.058 165 Example 11 3.6 6.7 0.137 0.057 184 Example 12 3.5 6.3 0.135 0.056 175 Example 13 3.7 6.5 0.136 0.055 177 Example 14 3.7 6.6 0.135 0.055 179 Example 15 3.6 6.2 0.138 0.053 181 Comparative Example 1 4.5 4.4 0.135 0.061 93

As a result of the experiment, the organic light emitting devices of Examples 1 to 15 including the organic compound of Formula 1 as a dopant in the light emitting layer of the present invention showed improved results in efficiency and voltage characteristics compared to the conventional organic light emitting device of Comparative Example 1. seemed

In addition, as a result of measuring the afterimage lifespan (T ₉₅ ), the organic electroluminescent device of Comparative Example 1 had a lifespan of 100 hours or less, whereas Examples 1 to 15 had a long lifespan of 150 hours or more, In particular, it was confirmed that the organic electroluminescent devices of Examples 11 and 15 had a long lifespan of 180 hours or more.

Therefore, it can be seen that the organic light emitting device including the organic compound of Chemical Formula 1 as a host in the light emitting layer of the present invention has excellent efficiency, voltage and lifetime characteristics.

2. Evaluation of characteristics of organic light emitting devices of Examples 16 to 30 and Comparative Example 2

The characteristics of the organic light emitting devices prepared in Examples 16 to 30 and Comparative Example 2 were measured at a current density of 10 mA/cm ² , and the results are shown in Table 2 below.

Voltage
(V) Efficiency
(Cd/A) CIE_x CIE_y T ₉₅ (hours) Example 16 3.5 6.7 0.135 0.056 185 Example 17 3.4 6.4 0.136 0.053 171 Example 18 3.6 7.0 0.135 0.058 166 Example 19 3.7 7.4 0.135 0.058 180 Example 20 3.5 6.3 0.137 0.052 189 Example 21 3.6 6.9 0.136 0.055 165 Example 22 3.4 6.4 0.137 0.054 180 Example 23 3.6 6.8 0.136 0.053 186 Example 24 3.5 6.7 0.135 0.054 190 Example 25 3.6 6.8 0.135 0.057 180 Example 26 3.5 7.1 0.137 0.056 215 Example 27 3.4 6.6 0.136 0.055 191 Example 28 3.6 6.8 0.136 0.054 193 Example 29 3.6 6.8 0.135 0.054 195 Example 30 3.5 6.4 0.138 0.052 206 Comparative Example 2 4.4 4.6 0.135 0.060 98

As a result of the experiment, the organic light emitting devices of Examples 16 to 30 using the compounds of Formulas 1 and 2 of the present invention in the light emitting layer and the hole transport layer were compared with the conventional organic light emitting device of Comparative Example 2 in efficiency and voltage characteristics. showed markedly improved results. In particular, the organic light emitting devices of Examples 17, 19, 22 and 27 exhibited remarkably improved characteristics in voltage characteristics and luminous efficiency.

In addition, as a result of measuring the afterimage lifespan (T ₉₅ ), the organic electroluminescent device of Comparative Example 2 had a lifespan of 100 hours or less, whereas Examples 16 to 30 had a long lifespan of 160 hours or more. In particular, it was confirmed that the organic light emitting devices of Examples 26 and 30 had a long lifespan of 200 hours or more.

Therefore, it can be seen that the organic electroluminescent device including the organic compound of Formula 1 as a host and the compound of Formula 2 in the hole transport layer of the present invention has significantly better efficiency, voltage, and lifespan compared to the conventional technology. there is.

3. Evaluation of characteristics of organic light emitting devices of Examples 1, 16, 31, 32 and Comparative Examples 1 and 2

The characteristics of the organic light emitting devices prepared in Examples 1, 16, 31, and 32 and Comparative Examples 1 and 2 were measured at a current density of 10 mA/cm ² , and the results are shown in Table 3 below.

Voltage
(V) Efficiency
(Cd/A) CIE_x CIE_y T ₉₅ (hours) Example 1 3.6 6.5 0.135 0.057 168 Example 16 3.5 6.7 0.135 0.056 185 Example 31 3.4 6.9 0.135 0.058 201 Example 32 3.5 6.7 0.136 0.056 192 Comparative Example 1 4.5 4.4 0.135 0.061 93 Comparative Example 2 4.4 4.6 0.135 0.060 98

As a result of the above experiment, the organic electroluminescent devices of Examples 16, 31, and 32 using the compounds of Formulas 1 and 2 of the present invention in the light emitting layer and the hole transport layer were the organic compounds of Formula 1 of the present invention as well as Comparative Examples 1 and 2. As a host, it exhibited remarkably excellent voltage characteristics, luminous efficiency and lifespan characteristics compared to Example 1 including the light emitting layer. These results are clearly confirmed through comparisons of Example 2 and Example 17, Example 3 and Example 18, Example 4 and Example 19, Example 5 and Example 20, and the like.

Therefore, it can be seen that the organic electroluminescent device including the organic compound of Formula 1 as a host in the light emitting layer and the compound of Formula 2 in the hole transport layer of the present invention is significantly superior in efficiency, voltage, and lifespan compared to the conventional technology. there is.

The above result can be seen as obtained by using the compound of Formula 2, which is well compatible with the host structure of the compound of Formula 1, as a hole transport material.

In the case of a general organic light emitting device, as degradation progresses at the interface between the hole transport layer and the light emitting layer, electrons are diffused into the hole transport layer through the interface, thereby accelerating the degradation and reducing the lifetime of the organic light emitting device.

However, in the present invention, as the compound of Formula 2 is used as a hole transport material, the charge balance of the device is achieved and excitons cannot migrate to the interface of the light emitting layer, so the efficiency of the organic light emitting device seems to be improved. In addition, it seems that the compound of Chemical Formula 2 prevents excitons from diffusing into the hole transport layer, thereby preventing overall deterioration, thereby increasing the lifetime of the organic light emitting device.

Claims (7)

In the organic electroluminescent device in which an organic thin film layer composed of one or a plurality of layers including at least a light emitting layer is laminated between a cathode and an anode,
An organic electroluminescent device, characterized in that the compound constituting the organic thin film layer contains tritium in its chemical structure, The organic electroluminescent device according to claim 1, characterized in that it contains an organic compound represented by the following formula (1)
[Formula 1]

in the above formula
Ar1 and Ar2 are each independently selected from tritium, deuterium, hydrogen, CN, straight or branched chain alkyl having 1 to 40 carbon atoms, alkoxy having 1 to 40 carbon atoms, thioalkyl having 1 to 40 carbon atoms, cycloalkyl having 3 to 40 carbon atoms, Phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl , A pyrazinyl group, a pyrimidinyl group, and an aromatic hydrocarbon group having 6 to 60 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of a quinolinyl group,
tritium, deuterium, hydrogen, CN, straight or branched chain alkyl of 1 to 40 carbon atoms, alkoxy of 1 to 40 carbon atoms, thioalkyl of 1 to 40 carbon atoms, cycloalkyl of 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl , anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, spirobi [fluorene], carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyra Hetero having 5 to 70 carbon atoms, substituted or unsubstituted with one or more selected from the group consisting of zinyl, pyrimidinyl, and quinolinyl, and containing one or more elements selected from the group consisting of S, O, N, and Si It is an aromatic hydrocarbon group,
R1, R2, R3, R4, R5, R6, R7 and R8 are each independently tritium, deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , carbon atoms a straight-chain or branched-chain alkyl group of 1 to 40 carbon atoms, an alkoxy group of 1 to 40 carbon atoms, a thioalkyl group of 1 to 40 carbon atoms, or a cycloalkyl group of 3 to 40 carbon atoms;
tritium, deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , straight or branched chain alkyl of 1 to 40 carbon atoms, alkoxy of 1 to 40 carbon atoms, 1 carbon atom thioalkyl of 3 to 40 carbon atoms, cycloalkyl of 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carba An aromatic hydrocarbon group having 6 to 60 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of zoyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, and quinolinyl,
tritium, deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , straight or branched chain alkyl of 1 to 40 carbon atoms, alkoxy of 1 to 40 carbon atoms, 1 carbon atom thioalkyl of 3 to 40 carbon atoms, cycloalkyl of 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, spirobi[ fluorene], carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl group, and substituted or unsubstituted with one or more selected from the group consisting of S, O, A heteroaromatic hydrocarbon group having 5 to 70 carbon atoms containing at least one element selected from the group consisting of N and Si;
tritium, deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , straight or branched chain alkyl of 1 to 40 carbon atoms, alkoxy of 1 to 40 carbon atoms, 1 carbon atom substituted or unsubstituted phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl, phenanthrenyl substituted with one or more selected from the group consisting of thioalkyl groups having 3 to 40 carbon atoms and cycloalkyl groups having 3 to 40 carbon atoms. At least one selected from the group consisting of pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and pyrimidinyl groups is an amino group substituted with The method of claim 2,
The organic compound is characterized in that any one of the following compounds 1 to 463.

In the organic electroluminescent device in which an organic thin film layer composed of one or a plurality of layers including at least a light emitting layer is laminated between a cathode and an anode,
An organic electroluminescent device characterized in that the light emitting layer contains the organic compound of claim 1 alone or in combination of two or more. The method of claim 4,
The organic thin film layer includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer,
The organic electroluminescent device, characterized in that the hole transport layer contains an organic compound represented by the following formula (2) alone or in combination of two or more:
[Formula 2]

In the above formula,
R1, R2, R3 and R4 are each independently hydrogen; a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms; Aromatic hydrocarbon having 6 to 60 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of C1~C10 straight chain or branched chain alkyl, C1~C10 alkoxy, halogen, CN, CF ₃ and Si(CH ₃ ) ₃ group energy; or C1~C10 straight-chain or branched-chain alkyl, C1~C10 alkoxy, halogen, CN, CF ₃ and Si(CH ₃ ) ₃ groups, substituted or unsubstituted with one or more selected from the group consisting of S, O, N and a heteroaromatic hydrocarbon group having 5 to 60 carbon atoms containing at least one element selected from the group consisting of Si;
Each of R1, R2, R3 and R4 may be independently bonded to the phenyl group of the basic structure to form an aromatic hydrocarbon or a heteroaromatic hydrocarbon. The method of claim 5,
Wherein R1, R2, R3 and R4 are each independently a phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl carbazole or pyrenyl group;
Wherein R1, R2, R3 and R4 are each independently bonded to the phenyl group of the basic structure to form naphthalene, anthracene, or phenanthrene. The method of claim 5,
An organic compound, characterized in that the organic compound is any one of the following compounds 464 to 475: