KR20230100665A - Novel organic compounds and an organic electroluminescent device comprising the same - Google Patents

Abstract

In an organic electroluminescent element wherein an organic thin film layer consisting of one layer or a plurality of layers comprising at least a light emitting layer is stacked between a negative pole and a positive pole, provided is the organic electroluminescent element wherein a compound constituting the organic thin film layer is characterized in which deuterium contains more than 50% compared to hydrogen, in a ratio of deuterium and hydrogen within a chemical structure. Therefore, the present invention is capable of improving light emitting efficiency and light emitting lifespan.

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, pyrene-based derivatives, and BN-based derivatives are used, but there are problems in that it is difficult to obtain deep blue and the emission lifetime becomes shorter as the wavelength goes shorter.

In addition, in this case, even in the case of green and red colors, it is difficult to obtain deep green and deep red colors, which is a technical limitation already recognized.

Therefore, development of deep blue materials, deep green materials, and deep red materials with long lifespan in realizing a full color display of natural colors, and these dopant materials The development of other organic materials that match the energy level is required.

Republic of Korea Patent No. 1022021710000 Republic of Korea Patent No. 1018256120000 Republic of Korea Patent No. 1012267000000 Republic of Korea Patent No. 1017453390000

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 material for a light emitting layer and improves the light emitting efficiency and light emitting 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 light emitting layer 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 lifespan by including the dopant material, the host material, and a specific hole transport layer material in combination.

Deuterium is one of the isotopes of hydrogen and has a deuteron as a nucleus composed of one proton and one neutron. The element symbol can also be written as D or 2H. On Earth, the ratio of 1H to D is about 6000:1. The proton, the nucleus of hydrogen (hydrogen-1), and the deuteron, the nucleus of deuterium (hydrogen-2), not only have a double mass difference, but also have spins of 1/2 and 1, respectively, which are called fermions and bosons. Physically, they have completely different properties. Since both have different spins, they both have a charge of +e, but they also have different magnetic dipole moments, so they appear in different shapes in the nuclear magnetic resonance (NMR) spectrum. The unstable hydrogen group of the compound comes off as H+ when it enters water, but it can be replaced with D+ by mixing a little heavy water in the water. In general, deuterium bonds are stronger than hydrogen. The energy level of deuterium atoms is lower than that of hydrogen atoms, and the light from deuterium appears slightly bluer than that of hydrogen atoms. Although it is a difference of 0.03%, a difference in wavelength is detected in the infrared region. If these characteristics are applied to OLED materials, lifespan and efficiency, which are the most problematic issues in organic light emitting devices, can be greatly improved.

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

[Formula 1]

in the above formula

Ar1, Ar2, Ar3 and Ar4 are each independently 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, pyridine An aromatic hydrocarbon group having 6 to 60 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of one, pyrazinyl, pyrimidinyl, and quinolinyl,

Deuterium, hydrogen, CN, straight chain 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, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, spirobi [fluorene], carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyridine substituted with a phenyl group A heteroaromatic hydrocarbon group having 5 to 70 carbon atoms that is unsubstituted or substituted with one or more selected from the group consisting of a midinyl group and a quinolinyl group and contains one or more elements selected from the group consisting of S, O, N and Si is,

B1 and B2 are each independently selected from 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, anthra Anthracenyl, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, and It is an aromatic hydrocarbon group having 6 to 60 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of quinolinyl groups,

n and m are independently 0 and 1, respectively;

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

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, Thioalkyl, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, di An aromatic hydrocarbon group having 6 to 60 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of benzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, and quinolinyl,

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, Thioalkyl, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, spirobi [fluorene], substituted or unsubstituted with one or more selected from the group consisting of carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl group, and quinolinyl group, and S, O, N and Si A heteroaromatic hydrocarbon group having 5 to 70 carbon atoms containing at least one element selected from the group consisting of

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, Phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with phenyl group, phenanthrenyl, pyrenyl unsubstituted or substituted with one or more selected from the group consisting of thioalkyl and cycloalkyl group having 3 to 40 carbon atoms , 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and substituted with one or more selected from the group consisting of pyrimidinyl groups is an amino group.

In addition, the present invention provides an organic compound represented by Formula 2 below:

[Formula 2]

in the above formula

Ar1 and Ar2 are each independently 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, bi Phenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl , 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,

Deuterium, hydrogen, CN, straight chain 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, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, spirobi [fluorene], carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyridine substituted with a phenyl group A heteroaromatic hydrocarbon group having 5 to 70 carbon atoms that is unsubstituted or substituted with one or more selected from the group consisting of a midinyl group and a quinolinyl group and contains one or more elements selected from the group consisting of S, O, N and Si is,

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

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, Thioalkyl, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, di An aromatic hydrocarbon group having 6 to 60 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of benzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, and quinolinyl,

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, Thioalkyl, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, spirobi [fluorene], substituted or unsubstituted with one or more selected from the group consisting of carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl group, and quinolinyl group, and S, O, N and Si A heteroaromatic hydrocarbon group having 5 to 70 carbon atoms containing at least one element selected from the group consisting of

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, Phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with phenyl group, phenanthrenyl, pyrenyl unsubstituted or substituted with one or more selected from the group consisting of thioalkyl and cycloalkyl group having 3 to 40 carbon atoms , 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and substituted with one or more selected from the group consisting of pyrimidinyl groups is an amino group.

In addition, the present invention provides an organic compound represented by the following formula (3):

[Formula 3]

in the above formula

M is Ir, Os or Pt;

Ar1, Ar2 and Ar3 are each independently deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, pyridine, pyrimidine, pyrazine, 1,3,5-triazine, quinolone , isoquinoline, indolizine, 1-phenyl1H-indole, 2-phenyl-2H-isoindole, benzofuran, benzo[b]thiophene, benzo[d]thiazole, 4H-quinolizine, cinnoline, furan, phthalazine, quinazoline, quinoxaline, 1,8 -naphthyridine, pteridine, thiophene, oxazole, thiazole, isoxazole, isothiazole, 1,2,3-oxadiazole, 1,2,3-thiadiazole, 1,3,4-thiadiazole, pyridazine, furo[2,3-b]pyridine , furo[2,3-c]pyridine, furo[3,2-c]pyridine furo[3,2-b]pyridine benzo[d]oxazole furo[2,3-d]pyrimidine, furo[3,2- d]pyrimidine, furo[2,3-b]pyrazine, thieno[2,3-,b]pyridine, thieno[3,2-c]pyridine, thieno[3,2-b]pyridine, benzo[d]thiazole , thieno[2,3-d]pyrimidine, thieno[2,3-d]pyridazine, thieno[2,3-b]pyrazine, benzofuro[2,3-b]pyridine, benzofuro[2,3-c]pyridine , benzofuro[3,2-c]pyridine, benzofuro[3,2-b]pyridine, benzofuro[2,3-d]pyrimidine, benzofuro[2,3-b]pyrazine, benzo[4,5]thieno[2 ,3-b]pyridine, benzo[4,5]thieno[3,2-c]pyridine, benzo[4,5]thieno[3,2-b]pyridine, benzo[4,5]thieno[3,2 -b]pyridine, benzo[4,5]thieno[2,3-d]pyrimidine, benzo[4,5]thieno[2,3-b]pyrazine, furo[2,3-b:5,4-b ']dipyridine, furo[2,3-b:4,5-c']dipyridine, furo[2,3-b:5,4-c']dipyridine, furo[2,3-b:4,5- b']dipyridine, pyrido[3',2':4,5]furo[3,2-d]pyrimidine, thieno[2,3-b:5,4-b']dipyridine, thieno[2,3- b:5,4-c']dipyridine, thieno[2,3-b:4,5-c']dipyridine, thieno[2,3-b:4,5-b']dipyridine, pyrido[3', 2':4,5]thieno[2,3-d]pyridazine, straight or branched chain alkyl of 1 to 60 carbon atoms, alkoxy of 1 to 60 carbon atoms, thioalkyl of 1 to 60 carbon atoms, or cyclo of 3 to 60 carbon atoms an alkyl group,

Deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, straight or branched chain alkyl of 1 to 60 carbon atoms, alkoxy of 1 to 60 carbon atoms, thio of 1 to 60 carbon atoms Alkyl, cycloalkyl having 3 to 60 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzo It is unsubstituted or substituted with one or more selected from the group consisting of furanyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, and quinolinyl, and selected from the group consisting of S, O, N, and Si A heteroaromatic hydrocarbon group having 5 to 80 carbon atoms containing at least one element,

Deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, straight or branched chain alkyl of 1 to 60 carbon atoms, alkoxy of 1 to 60 carbon atoms, thio of 1 to 60 carbon atoms phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, An amino group substituted with one or more selected from the group consisting of 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and pyrimidinyl groups am.

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 the following Chemical Formula 4 alone or in combination of two or more:

[Formula 4]

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 material for a light emitting layer and improves the light emitting efficiency and light emitting 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 light emitting layer 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 dopant material, the host material, and a specific hole transport layer material in combination. An object of the present invention is to provide a novel organic compound that is used as a material for a light emitting layer and improves the light emitting efficiency and light emitting lifetime of an organic light emitting device.

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

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

[Formula 1]

in the above formula

Ar1, Ar2, Ar3 and Ar4 are each independently 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, pyridine An aromatic hydrocarbon group having 6 to 60 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of one, pyrazinyl, pyrimidinyl, and quinolinyl,

Deuterium, hydrogen, CN, straight chain 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, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, spirobi [fluorene], carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyridine substituted with a phenyl group A heteroaromatic hydrocarbon group having 5 to 70 carbon atoms that is unsubstituted or substituted with one or more selected from the group consisting of a midinyl group and a quinolinyl group and contains one or more elements selected from the group consisting of S, O, N and Si is,

B1 and B2 are each independently selected from 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, anthra Anthracenyl, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, and It is an aromatic hydrocarbon group having 6 to 60 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of quinolinyl groups,

n and m are independently 0 and 1, respectively;

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

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, Thioalkyl, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, di An aromatic hydrocarbon group having 6 to 60 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of benzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, and quinolinyl,

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, Thioalkyl, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, spirobi [fluorene], substituted or unsubstituted with one or more selected from the group consisting of carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl group, and quinolinyl group, and S, O, N and Si A heteroaromatic hydrocarbon group having 5 to 70 carbon atoms containing at least one element selected from the group consisting of

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, Phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with phenyl group, phenanthrenyl, pyrenyl unsubstituted or substituted with one or more selected from the group consisting of thioalkyl and cycloalkyl group having 3 to 40 carbon atoms , 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and substituted with one or more selected from the group consisting of pyrimidinyl groups is an amino group.

Specific examples of the organic compound include any one of the following compounds 1-1 to 1-124.

In addition, the present invention provides an organic compound represented by Formula 2 below:

[Formula 2]

in the above formula

Ar1 and Ar2 are each independently 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, bi Phenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl , 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,

Deuterium, hydrogen, CN, straight chain 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, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, spirobi [fluorene], carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyridine substituted with a phenyl group A heteroaromatic hydrocarbon group having 5 to 70 carbon atoms that is unsubstituted or substituted with one or more selected from the group consisting of a midinyl group and a quinolinyl group and contains one or more elements selected from the group consisting of S, O, N and Si is,

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

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, Thioalkyl, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, di An aromatic hydrocarbon group having 6 to 60 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of benzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, and quinolinyl,

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, Thioalkyl, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, spirobi [fluorene], substituted or unsubstituted with one or more selected from the group consisting of carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl group, and quinolinyl group, and S, O, N and Si A heteroaromatic hydrocarbon group having 5 to 70 carbon atoms containing at least one element selected from the group consisting of

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, Phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with phenyl group, phenanthrenyl, pyrenyl unsubstituted or substituted with one or more selected from the group consisting of thioalkyl and cycloalkyl group having 3 to 40 carbon atoms , 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and substituted with one or more selected from the group consisting of pyrimidinyl groups is an amino group.

Specific examples of the organic compound include any one of the following compounds 2-1 to 2-116.

In addition, the present invention provides an organic compound represented by the following formula (3):

[Formula 3]

in the above formula

M is Ir, Os or Pt;

Ar1, Ar2 and Ar3 are each independently deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, pyridine, pyrimidine, pyrazine, 1,3,5-triazine, quinolone , isoquinoline, indolizine, 1-phenyl1H-indole, 2-phenyl-2H-isoindole, benzofuran, benzo[b]thiophene, benzo[d]thiazole, 4H-quinolizine, cinnoline, furan, phthalazine, quinazoline, quinoxaline, 1,8 -naphthyridine, pteridine, thiophene, oxazole, thiazole, isoxazole, isothiazole, 1,2,3-oxadiazole, 1,2,3-thiadiazole, 1,3,4-thiadiazole, pyridazine, furo[2,3-b]pyridine , furo[2,3-c]pyridine, furo[3,2-c]pyridine furo[3,2-b]pyridine benzo[d]oxazole furo[2,3-d]pyrimidine, furo[3,2- d]pyrimidine, furo[2,3-b]pyrazine, thieno[2,3-,b]pyridine, thieno[3,2-c]pyridine, thieno[3,2-b]pyridine, benzo[d]thiazole , thieno[2,3-d]pyrimidine, thieno[2,3-d]pyridazine, thieno[2,3-b]pyrazine, benzofuro[2,3-b]pyridine, benzofuro[2,3-c]pyridine , benzofuro[3,2-c]pyridine, benzofuro[3,2-b]pyridine, benzofuro[2,3-d]pyrimidine, benzofuro[2,3-b]pyrazine, benzo[4,5]thieno[2 ,3-b]pyridine, benzo[4,5]thieno[3,2-c]pyridine, benzo[4,5]thieno[3,2-b]pyridine, benzo[4,5]thieno[3,2 -b]pyridine, benzo[4,5]thieno[2,3-d]pyrimidine, benzo[4,5]thieno[2,3-b]pyrazine, furo[2,3-b:5,4-b ']dipyridine, furo[2,3-b:4,5-c']dipyridine, furo[2,3-b:5,4-c']dipyridine, furo[2,3-b:4,5- b']dipyridine, pyrido[3',2':4,5]furo[3,2-d]pyrimidine, thieno[2,3-b:5,4-b']dipyridine, thieno[2,3- b:5,4-c']dipyridine, thieno[2,3-b:4,5-c']dipyridine, thieno[2,3-b:4,5-b']dipyridine, pyrido[3', 2':4,5]thieno[2,3-d]pyridazine, straight or branched chain alkyl of 1 to 60 carbon atoms, alkoxy of 1 to 60 carbon atoms, thioalkyl of 1 to 60 carbon atoms, or cyclo of 3 to 60 carbon atoms an alkyl group,

Deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, straight or branched chain alkyl of 1 to 60 carbon atoms, alkoxy of 1 to 60 carbon atoms, thio of 1 to 60 carbon atoms Alkyl, cycloalkyl having 3 to 60 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzo It is unsubstituted or substituted with one or more selected from the group consisting of furanyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, and quinolinyl, and selected from the group consisting of S, O, N, and Si A heteroaromatic hydrocarbon group having 5 to 80 carbon atoms containing at least one element,

Deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, straight or branched chain alkyl of 1 to 60 carbon atoms, alkoxy of 1 to 60 carbon atoms, thio of 1 to 60 carbon atoms phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, An amino group substituted with one or more selected from the group consisting of 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and pyrimidinyl groups am.

Specific examples of the organic compound include any one of the following compounds 3-1 to 3-225.

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 the following Chemical Formula 4 alone or in combination of two or more:

[Formula 4]

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 the following compounds 4-101 to 4-112.

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.

<Synthesis of compounds represented by Formulas 1, 2, 3, and 4>

<Synthesis of Intermediate-1>

Add 1.28 g (10 mmol) of naphthalene, 114 mg (0.50 mmol) of PtO ₂ , 2 mL of deuterium water (D ₂ O), 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 1.24 g (91%, deuterium conversion 94%) of Intermediate-1.

Intermediate-1 MS (FAB): 136 (M ⁺ )

<Synthesis of Intermediate-2>

After dissolving 1.36 g (10 mmol) of Intermediate-1 in 30 ml of MC in a 100 ml three-necked round bottom flask, 2.14 g (12 mmol) of NBS was slowly added thereto 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 1.78 g (83%) of Intermediate-2.

Intermediate-2 MS (FAB): 214 (M ⁺ )

<Synthesis of Intermediate-3>

After dissolving 100g (480mmol) of 1,2,3,6,7,8-hexahydropyrene in 1L of MC, 48ml of bromine was dissolved in 200ml of MC and added slowly. After 30 minutes, the resulting solid was washed with Ethanol, filtered, and dried to obtain 60 g (33% yield) of Intermediate-3.

Intermediate-3 MS (FAB): 366 (M ⁺ )

<Synthesis of Intermediate-4>

After dissolving 60g (163.9mmol) of Intermediate-3 in 2L of Toluene, 120mg of DDQ was added and refluxed for 4 hours. After completion of the reaction, toluene was distilled and column was performed to obtain 23 g (39% yield) of Intermediate-4.

Intermediate-4 MS (FAB): 360 (M ⁺ )

<Synthesis of Intermediate-5>

After dissolving 23 g (63.88 mmol) of Intermediate-4 in 100 ml of THF, -78 degrees was maintained in an Acetone/dryice bath. After slowly dropping 56ml (140mmol) of 2.5M n-BuLi, the mixture was stirred for 30 minutes. After adding iodomethane 22.7g (160mmol), the temperature was gradually raised to room temperature. The organic layer was extracted by adding 300ml of EA and 300ml of H ₂ O, and distilled. Column was performed to obtain 9.4 g (64% yield) of Intermediate-5.

Intermediate-5 MS (FAB): 230 (M ⁺ )

<Synthesis of Intermediate-6>

After dissolving 9.4g (40.8mmol) of Intermediate-5 in 100ml of MC, 14.35g (89.8mmol) of bromine was slowly added. After 6 hours, the completion of the reaction was confirmed, and MC was distilled and columned. 3.6 g (23% yield) of Intermediate-6 was obtained.

Intermediate-6 MS (FAB): 388 (M ⁺ )

<Synthesis of Intermediate-7>

100g (277.7mmol) of Intermediate-4 and 74.5g (611.0mmol) of phenylboronic acid were dissolved in 600ml of Toluene and 60ml of Ethanol. After adding 611 ml of 2M K ₂ CO ₃ and 16.04 g (13.9 mmol) of Pd(PPh ₃ ) ₄ , the mixture was refluxed for 12 hours. After completion of the reaction, the toluene layer was extracted and filtered through silica. Recrystallization from n-hexane/MC yielded 64 g (65% yield) of Intermediate-7.

Intermediate-7 MS (FAB): 354 (M ⁺ )

<Synthesis of Intermediate-8>

After dissolving 64g (180.57mmol) of Intermediate-7 in 1000ml of MC, 63.5g (397.25mmol) of Bromine was slowly added. After 6 hours, the completion of the reaction was confirmed, and MC was distilled and columned. 66.6 g (72% yield) of Intermediate-8 was obtained.

Intermediate-8 MS (FAB): 512 (M ⁺ )

<Synthesis of Intermediate-9>

After dissolving pyrene 100g (494.4mmol) in MC 1000ml, bromine 158g (988.8mmol) was slowly added. After 6 hours, the completion of the reaction was confirmed, and MC was distilled and columned. 71.2 g (40% yield) of Intermediate-9 was obtained.

Intermediate-9 MS (FAB): 360 (M ⁺ )

<Synthesis of Intermediate-10>

After dissolving 100 g (434.2 mmol) of Intermediate-5 in 1000 ml of MC, 138.8 g (868.4 mmol) of Bromine was slowly added. After 6 hours, the completion of the reaction was confirmed, and MC was distilled and columned. 27.0 g (16% yield) of Intermediate-10 was obtained.

Intermediate-10 MS (FAB): 388 (M ⁺ )

<Synthesis of Intermediate-11>

After dissolving 27 g (69.6 mmol) of Intermediate-10 in 100 ml of THF, -78 degrees was maintained in an Acetone/dryice bath. After slowly dropping 61ml (153.1mmol) of 2.5M n-BuLi, the mixture was stirred for 30 minutes. After adding iodomethane 22.7g (160mmol), the temperature was gradually raised to room temperature. The organic layer was extracted by adding 300ml of EA and 300ml of H ₂ O, and distilled. Column was performed to obtain 9.7 g (54% yield) of Intermediate-11.

Intermediate-11 MS (FAB): 258 (M ⁺ )

<Synthesis of Intermediate-12>

After dissolving 9.7g (37.5mmol) of Intermediate-11 in 1000ml of MC, 12.6g (78.8mmol) of Bromine was slowly added. After 6 hours, the completion of the reaction was confirmed, and MC was distilled and columned. 14.7 g (94% yield) of Intermediate-12 was obtained.

Intermediate-12 MS (FAB): 416 (M ⁺ )

<Synthesis of Intermediate-13>

After dissolving 100 g (277.8 mmol) of Intermediate-4 in 1000 ml of THF, -78 degrees was maintained in an Acetone/dryice bath. After slowly dropping 122ml (305.6mmol) of 2.5M n-BuLi, the mixture was stirred for 30 minutes. After adding iodomethane 47.3g (333.4mmol), the temperature was gradually raised to room temperature. After THF distillation, 1000 ml of EA and 100 ml of H ₂ O were added to extract the organic layer, followed by distillation. Column was performed to obtain 55.7 g (68% yield) of Intermediate-13.

Intermediate-13 MS (FAB): 295 (M ⁺ )

<Synthesis of Intermediate-14>

After dissolving 55.7g (188.9mmol) of Intermediate-13 in 500ml of THF, 2.58g (3.8mmol) of NiCl ₂ dppf was added. Cyclohexylmagnesium chloride (1M) 190ml was slowly added at room temperature. After stirring at room temperature for 6 hours and completing the reaction, 500 ml of H2O was slowly added to quench. THF was distilled off and extracted by adding 500 ml of MC. Column was performed to obtain 25.9 g (46% yield) of Intermediate-14.

Intermediate-14 MS (FAB): 298 (M ⁺ )

<Synthesis of Intermediate-15>

After dissolving 25.9g (86.9mmol) of Intermediate-14 in 500ml of MC, 30.6g (191.2mmol) of Bromine was slowly added. After 6 hours, the completion of the reaction was confirmed, and MC was distilled and columned. 10.3 g (26% yield) of Intermediate-15 was obtained.

Intermediate-15 MS (FAB): 456 (M ⁺ )

<Synthesis of Intermediate-16>

After dissolving 100g (404.7mmol) of 4-bromodibenzofuran and 54.7g (404.7mmol) of 4-isopropylaniline in 500ml of Toluene, 58.3g (607.1mmol) of sodium tert-butoxide was added. After adding 1.82 g (8.1 mmol) of palladium acetate and 6.55 g (16.2 mmol) of tri-tert-butylphosphine (50% in toluene), it was refluxed for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, and 500 ml of water was added thereto, and the organic layer was extracted. Recrystallization from N-hexane/MC yielded 122 g (63% yield) of Intermediate-16.

Intermediate-16 MS (FAB): 301 (M ⁺ )

<Synthesis of Intermediate-17>

After dissolving 100 g (739.6 mmol) of 4-isopropylaniline in 1 L of DMF, it was maintained at -20 degrees using an ice salt bath. After slowly adding 98.8 g (739.6 mmol) of NCS, the temperature was gradually raised to room temperature. After completion of the reaction, EA layer was extracted by adding 2L of EA and 2L of water, and distilled. column to obtain 41.4 g (33% yield) of Intermediate-17.

Intermediate-17 MS (FAB): 169 (M ⁺ )

<Synthesis of Intermediate-18>

60.3g (244mmol) of 4-bromodibenzofuran and 41.4g (244mmol) of Intermediate-17 were dissolved in 600ml of Toluene, and then 117.2g (1220mmol) of sodium tert-butoxide was added. After adding Palladium acetate 1.64g (7.32mmol) and t-Bu ₃ PHBF ₄ 2.12g (7.32mmol), it was refluxed for 6 hours. After completion of the reaction, the mixture was cooled to room temperature, and an organic layer was extracted by adding 1 L of EA and 1 L of water. After column, it was recrystallized with n-hexane/MC to obtain 59 g (72% yield) of Intermediate-18.

Intermediate-18 MS (FAB): 335 (M ⁺ )

<Synthesis of Intermediate-19>

After dissolving 59g (175.7mmol) of Intermediate-18 in 600ml of DMA, 33.8g (351.4mmol) of sodium tert-butoxide was added. After adding 1.18g (5.27mmol) of Palladium acetate and 1.53g (5.27mmol) of t-Bu ₃ PHBF _4, it was refluxed for 6 hours. After completion of the reaction, the mixture was cooled to room temperature, 500ml of EA and 1L of water were added thereto, and the EA layer was extracted. After column, it was recrystallized with n-hexane/MC to obtain 30.5 g (58% yield) of Intermediate-19.

Intermediate-19 MS (FAB): 299 (M ⁺ )

<Synthesis of Intermediate-20>

After adding 100 g (306.8 mmol) of 4,6-dibromodibenzofuran to a 2L high-pressure reactor, 1200 ml of PEG 300 and 400 ml of ammonium hydroxide (30% aq) were added. After adding 584 mg (3.07 mmol) of Copper(I) iodide, the mixture was reacted at 130 degrees for 24 hours. After completion of the reaction, the mixture was cooled to room temperature, and an organic layer was extracted by adding 500 ml of EA and 500 ml of water. After silica filter, it was recrystallized with n-hexane/MC to obtain 57.8 g (95% yield) of Intermediate-20.

Intermediate-20 MS (FAB): 198 (M ⁺ )

<Synthesis of Intermediate-21>

After dissolving 57.8 g (291.6 mmol) of Intermediate-20 in 600 ml of DMF, it was maintained at -20 degrees using an ice-salt bath. After slowly adding 103.8 g (583.2 mmol) of NBS, the temperature was gradually raised to room temperature. After completion of the reaction, 1 L of EA and 1 L of water were added, and the organic layer was extracted. After column, it was recrystallized with n-hexane/MC to obtain 84.1 g (81% yield) of Intermediate-21.

Intermediate-21 MS (FAB): 356 (M ⁺ )

<Synthesis of Intermediate-22>

After adding 84.1g (236.2mmol) of Intermediate-21 to 1L of ethanol, 100ml of H ₂ SO ₄ was slowly added. 48.9 g (708.6 mmol) of NaNO ₂ was added slowly. After refluxing for 2 hours, the completion of the reaction was confirmed and cooled to room temperature. After adding 1 L of EA and 2 L of water, the organic layer was extracted. Column with N-hexane to obtain 24.6 g (32% yield) of Intermediate-22.

Intermediate-22 MS (FAB): 325 (M ⁺ )

<Synthesis of Intermediate-23>

After dissolving 24.6g (75.6mmol) of 1,9-dibromodibenzofuran and 10.2g (75.6mmol) of 4-isopropylaniline in 300ml of toluene, 36.3g (378mmol) of sodium tert-butoxide was added. After adding 510 mg (2.27 mmol) of Palladium acetate and 660 mg (2.27 mmol) of t-Bu3PHBF4, it was refluxed for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, and an organic layer was extracted by adding 1 L of EA and 1 L of water. After column, it was recrystallized with n-hexane/MC to obtain 16.1 g (56% yield) of Intermediate-23.

Intermediate-23 MS (FAB): 380 (M ⁺ )

<Synthesis of Intermediate-24>

After dissolving 16.1 g (42.3 mmol) of Intermediate-23 in 300 ml of DMA, 8.1 g (84.6 mmol) of sodium tert-butoxide was added. After adding 285mg (1.27mmol) of Palladium acetate and 370mg (1.27mmol) of t-Bu3PHBF4, it was refluxed for 6 hours. After completion of the reaction, the mixture was cooled to room temperature, 300 ml of EA and 500 ml of water were added, and the EA layer was extracted. After column, it was recrystallized with n-hexane/MC to obtain 5.45 g (43% yield) of Intermediate-24.

Intermediate-24 MS (FAB): 299 (M ⁺ )

<Synthesis of Intermediate-25>

100g (404.7mmol) of 3-bromodibenzofuran and 74g (607.1mmol) of phenylboronic acid were dissolved in 600ml of Toluene and 60ml of Ethanol. After adding 607 ml of 2M K ₂ CO ₃ and 23.4 g (20.2 mmol) of Pd(PPh ₃ ) ₄ , the mixture was refluxed for 12 hours. After completion of the reaction, the toluene layer was extracted and filtered through silica. It was recrystallized from n-hexane/MC to obtain 83 g (84% yield) of Intermediate-25.

Intermediate-25 MS (FAB): 244 (M ⁺ )

<Synthesis of Intermediate-26>

After dissolving 83 g (340 mmol) of Intermediate-25 in 500 ml of THF, -78 degrees was maintained using an acetone/dryice bath.

After slowly adding 150ml (374mmol) of 2.5M n-BuLi, the bath was removed and the temperature was raised to room temperature. After 1 hour, -78 degrees was maintained using an acetone/dryice bath, and 38.9 g (374 mmol) of trimethylborate was added. After removing the bath, the temperature was raised to room temperature to terminate the reaction. After extracting the organic layer by adding EA 1L and water 1L, distillation and column to obtain 38.2g (39% yield) of Intermediate-26.

Intermediate-26 MS (FAB): 288 (M ⁺ )

<Synthesis of Intermediate-27>

After dissolving 100 g (739.6 mmol) of 4-isopropylaniline in 1 L of DMF, 131.6 g (739.6 mmol) of NBS was slowly added at 0 degrees. After removing the bath, the temperature was raised to room temperature to complete the reaction, and 2L of EA and 2L of water were added. The organic layer was extracted, distilled, and columnized to obtain 139.4 g (88% yield) of Intermediate-27.

Intermediate-27 MS (FAB): 214 (M ⁺ )

<Synthesis of Intermediate-28>

After dissolving 38.2g (132.6mmol) of Intermediate-26 and 28.4g (132.6mmol) of Intermediate-27 in 300ml of MC, 482mg (2.65mmol) of Cupper acetate was added and reacted for 24 hours while blowing air. After completion of the reaction, column was performed to obtain 52 g (86% yield) of Intermediate-28.

Intermediate-28 MS (FAB): 456 (M ⁺ )

<Synthesis of Intermediate-29>

After dissolving 52g (114mmol) of Intermediate-28 in 500ml of DMA, 21.9g (228mmol) of sodium tert-butoxide was added. After adding 768mg (3.42mmol) of Palladium acetate and 992mg (3.42mmol) of t-Bu ₃ PHBF ₄ , it was refluxed for 6 hours. After completion of the reaction, the mixture was cooled to room temperature, 1000 ml of EA and 1000 ml of water were added, and the EA layer was extracted. After column, it was recrystallized with n-hexane/MC to obtain 22.3 g (52% yield) of Intermediate-29.

Intermediate-29 MS (FAB): 375 (M ⁺ )

<Synthesis of Intermediate-30>

After dissolving 100 g (306.8 mmol) of 1,9-dibromodibenzofuran and 233.7 g (920.3 mmol) of B2pin2 in 1 L of 1,4-dioxane, 150.5 g (1534 mmol) of potassium acetate was added. After adding 6.89 g (30.68 mmol) of Palladium acetate and 17 g (30.68 mmol) of dppf, it was refluxed for 12 hours. After completion of the reaction, the solvent was distilled and column was performed to obtain 56.7 g (44% yield) of Intermediate-30.

Intermediate-30 MS (FAB): 420 (M ⁺ )

<Synthesis of Intermediate-31>

After dissolving 100g (739.6mmol) of 4-isopropylaniline in 1L of DMF, 166.4g (739.6mmol) of NIS was slowly added at 0°C. After removing the bath, the temperature was raised to room temperature to complete the reaction, and 2L of EA and 2L of water were added. The organic layer was extracted, distilled, and columnized to obtain 166.1 g (86% yield) of Intermediate-31.

Intermediate-31 MS (FAB): 261 (M ⁺ )

<Synthesis of Intermediate-32>

100g (383mmol) of Intermediate-31 and 76.9g (383mmol) of (2-bromophenyl)boronic acid were dissolved in 600ml of Toluene and 60ml of Ethanol. After adding 383 ml of 2M K2CO3 and 22.1 g (19.15 mmol) of Pd(PPh ₃ ) ₄ , it was refluxed for 12 hours. After completion of the reaction, the toluene layer was extracted and filtered through silica. It was recrystallized from n-hexane/MC to obtain 84.5 g (76% yield) of Intermediate-32.

Intermediate-32 MS (FAB): 290 (M ⁺ )

<Synthesis of Intermediate-33>

56.7g (135mmol) of Intermediate-30 and 39.2g (135mmol) of Intermediate-32 were dissolved in 500ml of Toluene and 50ml of Ethanol. After adding 135 ml of 2M K2CO3 and 7.8 g (6.75 mmol) of Pd(PPh ₃ ) ₄ , it was refluxed for 12 hours. After completion of the reaction, the toluene layer was extracted and columned to obtain 24.5 g (36% yield) of Intermediate-33.

Intermediate-33 MS (FAB): 503 (M ⁺ )

<Synthesis of Intermediate-34>

After dissolving 24.5g (48.6mmol) of Intermediate-33 in 300ml of MC, 177mg (0.97mmol) of Cupper acetate was added and reacted for 24 hours while blowing air. After completion of the reaction, column was obtained to obtain 15.3 g (84% yield) of Intermediate-34.

Intermediate-34 MS (FAB): 375 (M ⁺ )

<Synthesis of Intermediate-35>

After dissolving 100 g (404.7 mmol) of 3-bromodibenzofuran in 1000 ml of THF, -78 degrees was maintained using an acetone/dryice bath. After slowly adding 445ml (445mmol) of 1.0M LDA, the mixture was stirred for 1 hour. While maintaining -78 degrees, 147.6 g (445.2 mmol) of CBr ₄ was added. The reaction was terminated by removing the bath, raising the temperature to room temperature, and stirring for 1 hour. After extracting the organic layer by adding 1L of EA and 1L of water, it was distilled and columned to obtain 83.1 g (63% yield) of Intermediate-35.

Intermediate-35 MS (FAB): 325 (M ⁺ )

<Synthesis of Intermediate-36>

After dissolving 83.1 g (255 mmol) of Intermediate-35 and 54.6 g (255 mmol) of Intermediate-25 in 300 ml of NMP, 166.2 g (510 mmol) of Cesium carbonate was added. After confirming the completion of the reaction by stirring at 180 degrees for 3 hours, the mixture was cooled to room temperature. The organic layer was extracted by adding 300 ml of EA and 300 ml of water. Column was performed to obtain 69.1 g (59% yield) of Intermediate-36.

Intermediate-36 MS (FAB): 459 (M ⁺ )

<Synthesis of Intermediate-37>

After dissolving 95.7g (306.8mmol) of 2,2'-dibromo-1,1'-biphenyl and 233.7g (920.3mmol) of B2pin2 in 1L of 1,4-dioxane, 150.5g (1534mmol) of potassium acetate was added. After adding 6.89 g (30.68 mmol) of Palladium acetate and 17 g (30.68 mmol) of dppf, it was refluxed for 12 hours. After completion of the reaction, the solvent was distilled off and column was performed to obtain 51.1 g (41% yield) of Intermediate-37.

Intermediate-37 MS (FAB): 406 (M ⁺ )

<Synthesis of Intermediate-38>

69g (150.3mmol) of Intermediate-36 and 61g (150.3mmol) of Intermediate-37 were dissolved in 1000ml of Toluene and 100ml of Ethanol. After adding 300 ml of 2M K ₂ CO ₃ and 17.4 g (15.03 mmol) of Pd(PPh ₃ ) ₄ , the mixture was refluxed for 12 hours. After completion of the reaction, the toluene layer was extracted and columned to obtain 23.8 g (35% yield) of Intermediate-38.

Intermediate-38 MS (FAB): 451 (M ⁺ )

<Synthesis of Intermediate-39>

After dissolving 20 g (51.5 mmol) of Intermediate-6 and 15.4 g (51.5 mmol) of Intermediate-26 in 500 ml of toluene, 19.8 g (206.1 mmol) of sodium tert-butoxide was added. After adding 231 mg (1.03 mmol) of Palladium acetate and 417 mg (2.06 mmol) of Tri-tert-butylphosphine, it was refluxed for 12 hours. After completion of the reaction, the mixture was cooled to room temperature and an organic layer was extracted by adding 500 ml of water. After column, it was recrystallized with n-hexane/MC to obtain 13.4 g (43% yield) of Intermediate-39.

Intermediate-39 MS (FAB): 606 (M ⁺ )

<Synthesis of Intermediate-40>

Dissolve 200g (386.2mmol) of 1,3,6,8-tetrabromopyrene and 129.2g (772.5mmol) of carbazole in 500ml of nitrobenzene. After adding 7.36g (115.9mmol) of copper powder and 160.1g (1158.7mmol) of potassium carbonate, reflux for 6 hours. After completion of the reaction, cool to room temperature and distill nitrobenzene. After washing with MC and column after celite filter, 34.7 g (13% yield) of Intermediate-40 was obtained.

Intermediate-40 MS (FAB): 690 (M ⁺ )

<Synthesis of Intermediate-41>

Add 1.78 g (10 mmol) of anthracene, 114 mg (0.50 mmol) of Pt/C, 2 mL of deuterium water (DTO), 3.0 mL of 2-pentanol, and 60 mL of decahydronaphthalene. After stirring at 140 ° C. for 24 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 1.47 g of Intermediate-41 (78%, 95% deuterium conversion).

Intermediate-41 MS (FAB): 188 (M ⁺ )

<Synthesis of Intermediate-42>

After dissolving 1.88 g (10 mmol) of Intermediate-41 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 2.26 g (85%) of Intermediate-42.

Intermediate-42 MS (FAB): 266 (M ⁺ )

<Synthesis of Intermediate-43>

In a 100ml three-necked round bottom flask, 2-bromonaphthalene 2.07g (10mmol), silver carbonate 668mg (2.4mmol), cyclohexyldiphenylphosphine 1.63g (6.1mmol), potassium carbonate 1.67g (12mmol), deuterium water (D ₂ O) Add 5.34 g (0.24 mol) and 10 mL of toluene. After stirring at 100°C for 3 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 (93%, deuterium conversion 11%) of Intermediate-43.

Intermediate-43 MS (FAB): 208 (M ⁺ )

<Synthesis of Intermediate-44>

3.83 g (10 mmol) of 9-bromo-10-(naphthalen-2-yl) anthracene, 668 mg (2.4 mmol) of silver carbonate, 1.63 g (6.1 mmol) of cyclohexyldiphenylphosphine, potassium carbonate in a 100 ml three-neck round bottom flask Add 1.67g (12mmol), 5.34g (0.24mol) of deuterium (D ₂ O) and 10mL of toluene. After stirring at 120°C for 36 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 3.62 g (91%, deuterium conversion 89%) of Intermediate-44.

Intermediate-44 MS (FAB): 398 (M ⁺ )

Synthesis of Intermediate-45

3.98 g (10 mmol) of Intermediate-44 was dissolved in 40 ml of anhydrous THF under nitrogen, the temperature of the reaction was lowered to -78 ° C, and 4 ml 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 = 5:1 to obtain 3.05 g (84%) of Intermediate-45.

Intermediate-45 MS (FAB): 363 (M ⁺ )

<Synthesis of Intermediate-46>

3.83g (10mmol) of 9-bromo-10-(naphthalen-1-yl)anthracene, 668mg (2.4mmol) of silver carbonate, 1.63g (6.1mmol) of cyclohexyldiphenylphosphine, potassium carbonate in a 100ml three-necked round bottom flask 1.67g (12mmol), 5.34g (0.24mol) of deuterium water (T ₂ O) and 10mL of toluene were added. After stirring at 120°C for 36 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 3.62 g (91%, deuterium conversion 43%) of Intermediate-46.

Intermediate-46 MS (FAB): 398 (M ⁺ )

Synthesis of Intermediate-47

3.98 g (10 mmol) of Intermediate-46 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 : EA = 5 : 1 to obtain 2.98 g (82%) of Intermediate-47.

Intermediate-47 MS (FAB): 363 (M+)

<Synthesis of Intermediate-48>

Add 1.44g (10mmol) of naphthalen-2-ol, 98mg (0.50mmol) of Pt/C, 5mL of deuterium water (T ₂ O), 3.0mL of isopropanol, and 60mL of cyclohexane. After stirring at 140 ° C. for 36 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 column to obtain 1.19 g of Intermediate-48 (78%, deuterium conversion 94%).

Intermediate-48 MS (FAB): 152 (M ⁺ )

<Synthesis of Intermediate-49>

Put 1.52 g (10 mmol) of Intermediate-48, 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, 1.84 g (86%) of Intermediate-49 was obtained.

Intermediate-49 MS (FAB): 214 (M ⁺ )

<Synthesis of Intermediate-50>

Add 1.63g (10mmol) of 1-chloronaphthalene, 98mg (0.50mmol) of Pt/C, 3.0mL of isopropanol, and 60mL of cyclohexane. After stirring at 140 ° C. for 24 hours in a D 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 1.17 g of Intermediate-50 (91%, 14% deuterium conversion).

Intermediate-50 MS (FAB): 129 (M ⁺ )

<Synthesis of Intermediate-51>

After dissolving 1.29 g (10 mmol) of Intermediate-50 in 30 ml of MC in a 100 ml three-neck round bottom flask, 2.14 g (12 mmol) of NBS was slowly added thereto 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 1.73 g (83%) of Intermediate-51.

Intermediate-51 MS (FAB): 208 (M ⁺ )

<Synthesis of Intermediate-52>

Add 2.57 g (10 mmol) of 1-bromoanthracene, 114 mg (0.50 mmol) of PtO ₂ , 3.0 mL of 2-pentanol, and 60 mL of decahydronaphthalene. After stirring at 140 ° C. for 4 hours under a D ₂ atmosphere 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 1.41 g (78%, deuterium conversion 9%) of Intermediate-52.

Intermediate-52 MS (FAB): 181 (M ⁺ )

<Synthesis of Intermediate-53>

After dissolving 1.81 g (10 mmol) of Intermediate-52 in 30 ml of MC in a 100 ml three-neck 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 4 hours, and 250 ml of EA and 250 ml of water were added. The organic layer was extracted, distilled, and columnized to obtain 2.20 g (85%) of Intermediate-53.

Intermediate-53 MS (FAB): 259 (M ⁺ )

<Synthesis of Intermediate-54>

In a 100ml three-neck round bottom flask, 2-bromonaphthalene 2.07g (10mmol), silver carbonate 668mg (2.4mmol), cyclohexyldiphenylphosphine 1.63g (6.1mmol), potassium carbonate 1.67g (12mmol), deuterium water (T ₂ O) Add 5.34 g (0.24 mol) and 10 mL of toluene. After stirring at 120°C for 7 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 1.91 g (91%, deuterium conversion 43%) of Intermediate-54.

Intermediate-54 MS (FAB): 210 (M ⁺ )

Synthesis of Intermediate-55

2.14g (10mmol) of Intermediate-2 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 = 5 : 1 to obtain 1.47 g (85%) of Intermediate-55.

Intermediate-55 MS (FAB): 173 (M ⁺ )

Synthesis of Intermediate-56

2.21 g (10 mmol) of Intermediate-49 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-56.

Intermediate-56 MS (FAB): 186 (M ⁺ )

<Synthesis of Intermediate-57>

Add 3.36g (10mmol) of 2,9-dibromophenanthrene, 98mg (0.50mmol) of Pt/C, 3.0mL of isopropanol, and 60mL of cyclohexane. 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 0.59 g of Intermediate-57 (23%, deuterium conversion 11%).

Intermediate-57 MS (FAB): 258 (M ⁺ )

Synthesis of Intermediate-58

2.58 g (10 mmol) of Intermediate-57 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:EA = 4:1 to obtain 1.87 g (84%) of Intermediate-58.

Intermediate-58 MS (FAB): 223 (M+)

<Synthesis of Intermediate-59>

3.01 g (10 mmol) of Intermediate-16, 114 mg (0.50 mmol) of Pt/C, 2 mL of deuterium water (D ₂ O), 3.0 mL of 2-pentanol, and 60 mL of decahydronaphthalene were 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 2.30 g (72%, deuterium conversion 91%) of Intermediate-59.

Intermediate-59 MS (FAB): 319 (M+)

<Synthesis of Intermediate-60>

2.99 g (10 mmol) of Intermediate-19, 114 mg (0.50 mmol) of Pt/C, 2 mL of deuterium water (D ₂ O), 3.0 mL of 2-pentanol, and 60 mL of decahydronaphthalene were 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 column to obtain 2.36 g of Intermediate-60 (75%, deuterium conversion 5.8%).

Intermediate-60 MS (FAB): 315 (M+)

<Synthesis of Intermediate-61>

In a 100ml three-necked round bottom flask, 3.88 g (10 mmol) of intermediate-6, 668 mg (2.4 mmol) of silver carbonate, 1.63 g (6.1 mmol) of cyclohexyldiphenylphosphine, 1.67 g (12 mmol) of potassium carbonate, deuterium water (D ₂ O) Add 5.34 g (0.24 mol) 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 2.72 g of Intermediate-61 (68%, deuterium conversion 33%).

Intermediate-61 MS (FAB): 400 (M ⁺ )

Synthesis of Intermediate-62

After injecting 2.14 g (10 mmol) of Intermediate-49 and 1.35 g (10 mmol) of 4-isopropylaniline under nitrogen and dissolving in 40 ml of toluene, 0.05 g (0.2 mmol) of Pd (OAc) ₂ and 0.4 ml of 1M t-Bu ₃ P (0.4 mmol) and 2.88 g (30 mmol) of t-BuONa, respectively, and then refluxed for 6 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted using 150 ml of toluene and 150 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 2.39 g (89%) of Intermediate-62.

Intermediate-62 MS (FAB): 268 (M ⁺ )

Synthesis of Intermediate-63

After injecting 2.14 g (10 mmol) of Intermediate-2 and 1.35 g (10 mmol) of 4-isopropylaniline under nitrogen and dissolving them in 40 ml of toluene, 0.05 g (0.2 mmol) of Pd (OAc) ₂ and 0.4 ml of 1M t-Bu ₃ P (0.4 mmol) and 2.88 g (30 mmol) of t-BuONa, respectively, and then refluxed for 6 hours.

After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted using 150 ml of toluene and 150 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 2.33 g (87%) of Intermediate-63.

Intermediate-63 MS (FAB): 268 (M ⁺ )

<Synthesis of Intermediate-64>

1,6-dibromo-3,8-diisopropylpyrene 4.44g (10mmol), silver carbonate 668mg (2.4mmol), cyclohexyldiphenylphosphine 1.63g (6.1mmol), potassium carbonate 1.67g ( 12mmol), deuterium (D ₂ O) 5.34g (0.24mol) and toluene 10mL were added. 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 3.14 g of Intermediate-64 (68%, 89% deuterium conversion).

Intermediate-64 MS (FAB): 462 (M ⁺ )

<Synthesis of Intermediate-65>

4-bromo-2-phenylpyridine 2.34g (10mmol), silver carbonate 668mg (2.4mmol), cyclohexyldiphenylphosphine 1.63g (6.1mmol), potassium carbonate 1.67g (12mmol), deuterium water (T ₂ O) 5.34 Add g (0.24 mol) 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 1.96 g (81%, deuterium conversion 91%) of Intermediate-65.

Intermediate-65 MS (FAB): 242 (M ⁺ )

<Synthesis of Intermediate-66>

9-methyl-9H-pyrido[3,4-b]indole-3-carboxylic acid 2.26g (10mmol), silver carbonate 668mg (2.4mmol), cyclohexyldiphenylphosphine 1.63g (6.1mmol), potassium carbonate 1.67 g (12 mmol), 5.34 g (0.24 mol) of deuterium water (T ₂ O) and 10 mL of toluene are added. 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 2.01 g (85%, deuterium conversion 92%) of Intermediate-66.

Intermediate-66 MS (FAB): 236 (M ⁺ )

<Synthesis of Intermediate-67>

10-(trifluoromethyl)benzo[h]imidazo[2,1-f][1,6]naphthyridine 2.87g (10mmol) and silver carbonate 668mg (2.4mmol), cyclohexyldiphenylphosphine 1.63g (6.1mmol), Add 1.67 g (12 mmol) of potassium carbonate, 5.34 g (0.24 mol) of deuterium 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 2.33 g (79%, deuterium conversion 90%) of Intermediate-67.

Intermediate-67 MS (FAB): 295 (M ⁺ )

Synthesis of Intermediate-68

After injecting 1.79g (10mmol) of Intermediate-55 and 2.42g (10mmol) of Intermediate-65 under nitrogen and dissolving them in 40ml 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, 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 = 4: 1 column was used to obtain Intermediate-68 2.13 g (72%) was obtained.

Intermediate-68 MS (FAB): 296 (M ⁺ )

Synthesis of Intermediate-69

After injecting 1.79g (10mmol) of Intermediate-56 and 2.34g (10mmol) of 4-bromo-2-phenylpyridine 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 Hex: EA = 4: 1 column to obtain Intermediate-69 2.02 g (68%) was obtained.

Intermediate-69 MS (FAB): 296 (M ⁺ )

<Synthesis of Intermediate-70>

2-(3,5-dimethylphenyl)-5-isobutylquinoline 2.89g (10mmol) and silver carbonate 668mg (2.4mmol), cyclohexyldiphenylphosphine 1.63g (6.1mmol), potassium carbonate 1.67g (12mmol), deuterium water (T ₂ O) 5.34 g (0.24 mol) and 10 mL of toluene were added. 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 2.07 g of Intermediate-70 (67%, 84% deuterium conversion).

Intermediate-70 MS (FAB): 309 (M ⁺ )

<Synthesis of Intermediate-71>

[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% yield) of Intermediate-71.

Intermediate-71 MS (FAB): 397 (M ⁺ )

<Synthesis of Intermediate-72>

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% yield) of Intermediate-72.

Intermediate-72 MS (FAB): 552 (M ⁺ )

<Synthesis of Intermediate-73>

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 2.38 g (74% yield) of Intermediate-73.

Intermediate-73 MS (FAB): 321 (M ⁺ )

<Synthesis of Intermediate-74>

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 1.99 g (81% yield) of Intermediate-74.

Intermediate-74 MS (FAB): 245 (M ⁺ )

<Synthesis of Intermediate-75>

After injecting 2.45 g (10 mmol) of Intermediate-74 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% yield) of Intermediate-75.

Intermediate-75 MS (FAB): 476 (M ⁺ )

<Synthesis of Compound 1-1>

After dissolving 20 g (43.8 mmol) of Intermediate-15 and 30.80 g (96.4 mmol) of Intermediate-59 in 500 ml of toluene, 21 g (219 mmol) of sodium tert-butoxide was added. After adding Palladium acetate 197mg (0.88mmol) and Tri-tert-butylphosphine 709mg (1.75mmol), it was refluxed for 12 hours. After completion of the reaction, the mixture was cooled to room temperature and an organic layer was extracted by adding 500 ml of water. After column, it was recrystallized with n-hexane/MC to obtain 22.38 g (55% yield) of Compound 1-1.

¹ H NMR was measured, but due to the reason that hydrogen was not partially substituted with deuterium, NMR spectrum peaks that were not separated and the area ratio was not constant appeared as shown in the figure below, and the synthesis was confirmed by mass spectrum as follows.

MS(FAB): 929(M ⁺ )

<Synthesis of Compound 1-13>

After dissolving 20 g (51.5 mmol) of Intermediate-6 and 34.13 g (108.2 mmol) of Intermediate-60 in 500 ml of toluene, 19.8 g (206.1 mmol) of sodium tert-butoxide was added. After adding 231 mg (1.03 mmol) of Palladium acetate and 417 mg (2.06 mmol) of Tri-tert-butylphosphine, it was refluxed for 12 hours. After completion of the reaction, the mixture was cooled to room temperature and an organic layer was extracted by adding 500 ml of water. After column, it was recrystallized with n-hexane/MC to obtain 23,34 g (53% yield) of Compound 1-13.

As in the synthesis of Compound 1-1, due to the fact that hydrogen and deuterium were not partially substituted, NMR spectrum peaks that were not separated and the area ratio were not constant appeared, and the synthesis was confirmed by mass spectrum as follows.

MS(FAB): 855(M ⁺ )

<Synthesis of Compound 1-73>

After dissolving 20g (39mmol) of Intermediate-8 and 25.87 (82mmol) of Intermediate-60 in 500ml of toluene, 15g (156.2mmol) of sodium tert-butoxide was added. After adding 175 mg (0.78 mmol) of Palladium acetate and 316 mg (1.56 mmol) of Tri-tert-butylphosphine, it was refluxed for 12 hours. After completion of the reaction, the mixture was cooled to room temperature and an organic layer was extracted by adding 500 ml of water. After column, it was recrystallized with n-hexane/MC to obtain 22.14 g (58% yield) of Compound 1-73.

As in the synthesis of Compound 1-1, due to the fact that hydrogen and deuterium were not partially substituted, NMR spectrum peaks that were not separated and the area ratio were not constant appeared, and the synthesis was confirmed by mass spectrum as follows.

MS(FAB): 979(M ⁺ )

<Synthesis of Compound 1-87>

After dissolving 15.0 g (21.7 mmol) of Intermediate-40 and 15.3 g (47.8 mmol) of Intermediate-59 in 300 ml of toluene, 8.4 g (86.9 mmol) of sodium tert-butoxide was added. After adding Palladium acetate 98mg (0.43mmol) and Tri-tert-butylphosphine 176mg (0.87mmol), it was refluxed for 12 hours. After completion of the reaction, the mixture was cooled to room temperature and an organic layer was extracted by adding 500 ml of water. After column, it was recrystallized with n-hexane/MC to obtain 7.84 g (31% yield) of compound 1-87.

As in the synthesis of Compound 1-1, due to the fact that hydrogen and deuterium were not partially substituted, NMR spectrum peaks that were not separated and the area ratio were not constant appeared, and the synthesis was confirmed by mass spectrum as follows.

MS(FAB): 1165(M ⁺ )

<Synthesis of Compound 1-105>

After dissolving 20 g (48.1 mmol) of Intermediate-12 and 31.83 g (100.9 mmol) of Intermediate-60 in 500 ml of toluene, 18.5 g (192.2 mmol) of sodium tert-butoxide was added. After adding Palladium acetate 216mg (0.96mmol) and Tri-tert-butylphosphine 389mg (1.92mmol), it was refluxed for 12 hours. After completion of the reaction, the mixture was cooled to room temperature and an organic layer was extracted by adding 500 ml of water. After column, it was recrystallized with n-hexane/MC to obtain 22.09 g (52% yield) of Compound 1-105.

As in the synthesis of Compound 1-1, due to the fact that hydrogen and deuterium were not partially substituted, NMR spectrum peaks that were not separated and the area ratio were not constant appeared, and the synthesis was confirmed by mass spectrum as follows.

MS(FAB): 883(M ⁺ )

<Synthesis of Compound 1-117>

After injecting 4.62g (10mmol) of Intermediate-64 and 5.91g (22mmol) of Intermediate-62 under nitrogen and dissolving in 60ml of toluene, 0.05g (0.2mmol) of Pd (OAc) _{2 and} 0.4ml (0.4ml) of 1M t-Bu ₃ P 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 = 3: 1 to obtain 6.19 g (74% yield) of compound 1-117.

As in the synthesis of Compound 1-1, due to the fact that hydrogen and deuterium were not partially substituted, NMR spectrum peaks that were not separated and the area ratio were not constant appeared, and the synthesis was confirmed by mass spectrum as follows.

MS(FAB): 837(M ⁺ )

<Synthesis of Compound 1-121>

After injecting 4.62g (10mmol) of Intermediate-64 and 5.91g (22mmol) of Intermediate-63 under nitrogen and dissolving them in 60ml of toluene, 0.05g (0.2mmol) of Pd(OAc) _{2 and} 0.4ml (0.4ml) of 1M t-Bu _3P 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 = 3: 1 column to obtain 6.36g (76% yield) of compound 1-121.

As in the synthesis of Compound 1-1, due to the fact that hydrogen and deuterium were not partially substituted, NMR spectrum peaks that were not separated and the area ratio were not constant appeared, and the synthesis was confirmed by mass spectrum as follows.

MS(FAB): 837(M ⁺ )

<Synthesis of Compound 2--69>

After injecting 3.33 g (10 mmol) of 1-bromo-2,2'-binaphthalene and 3.63 g (10 mmol) of Intermediate-45 under nitrogen and dissolving 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 = 2: 1 to obtain compound 2-69 4.63 g (81%) was obtained.

As in the synthesis of Compound 1-1, due to the fact that hydrogen and deuterium were not partially substituted, NMR spectrum peaks that were not separated and the area ratio were not constant appeared, and the synthesis was confirmed by mass spectrum as follows.

MS(FAB): 571(M+)

<Synthesis of Compound 2-116>

After injecting 3.47 g (10 mmol) of 6-bromodinaphtho [1,2-b: 1',2'-d] furan and 3.63 g (10 mmol) of Intermediate-47 under nitrogen and dissolving in 50 ml of toluene, Pd (PPh ₃ ) ₄ 0.58 g (0.5 mmol) and 15 ml (30 mmol) of 2M K ₂ CO ₃ 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 2-116 4.45 g (76%) was obtained.

As in the synthesis of Compound 1-1, due to the fact that hydrogen and deuterium were not partially substituted, NMR spectrum peaks that were not separated and the area ratio were not constant appeared, and the synthesis was confirmed by mass spectrum as follows.

MS(FAB): 585(M+)

<Synthesis of Compound 3-1>

3-1. Synthesis of iridium intermediates

Under nitrogen, 44.47 g (150 mmol) of Intermediate-68, 10.58 g (30 mmol) of Iridium (III) chloride trihydrate (IrCl ₃ -3H ₂ O), 450 mL of 2-ethoxyethanol, and 150 mL of distilled water were added and stirred under reflux for 24 hours. When the reaction was completed, it was cooled to room temperature and the precipitate was filtered. The obtained solid was washed with water and methanol, and recrystallized from nucleic acid to obtain 22.66 g (37%) of Ir-3-1.

Ir-3-1 MS (FAB): 1633 (M ⁺ )

3-1. Synthesis of iridium compounds

Ir-3-1 16.33 g (10 mmol), 2-phenylpyridine 4.66 g (30 mmol), AgOTf (trifluoromethanesulfonic acid silver salt) 7.71 g (30 mmol), 2-methoxy-ethyl ether (Diglyme) 50 mL for 12 hours Stir under reflux and cool to room temperature. The mixture was washed with water and methanol, and the resulting compound was columned at Hex:EA = 5:1 to obtain 8.60 g (46%) of crystalline compound 3-1 of the iridium compound represented by Formula 1.

MS(FAB): 935(M ⁺ )

<Synthesis of Compound 3-5>

3-5. Synthesis of iridium intermediates

Under nitrogen, 44.29 g (150 mmol) of Intermediate-67, 10.58 g (30 mmol) of Iridium (III) chloride trihydrate (IrCl ₃ -3H ₂ O), 450 mL of 2-ethoxyethanol, and 150 mL of distilled water were added and stirred under reflux for 24 hours. When the reaction was completed, it was cooled to room temperature and the precipitate was filtered. The obtained solid was washed with water and methanol, and recrystallized from nucleic acid to obtain 20.76 g (34%) of Ir-3-5.

Ir-3-5 MS(FAB): 1628(M ⁺ )

3-5. Synthesis of iridium compounds

16.28 g (10 mmol) of Ir-3-5, 7.09 g (30 mmol) of Intermediate-66, and 3.18 g of sodium carbonate anhydride were stirred under reflux in 150 ml of ethoxyethanol for 48 hours and cooled to room temperature. The mixture was washed with water and methanol, and the resulting compound was columned at Hex:EA = 5:1 to obtain 7.90 g (39%) of crystalline compound 3-5 of the iridium compound represented by Formula 1.

MS(FAB): 1013(M ⁺ )

<Synthesis of Compound 3-10>

3-10. Synthesis of iridium intermediates

Under nitrogen, 46.43 g (150 mmol) of Intermediate-70, 10.58 g (30 mmol) of Iridium (III) chloride trihydrate (IrCl ₃ -3H ₂ O), 450 mL of 2-ethoxyethanol, and 150 mL of distilled water were added and stirred under reflux for 24 hours. When the reaction was completed, it was cooled to room temperature and the precipitate was filtered. The obtained solid was washed with water and methanol, and recrystallized from nucleic acid to obtain 24.71 g (39%) of Ir-3-10.

Ir-3-10 MS (FAB): 1689 (M ⁺ )

3-10. Synthesis of iridium compounds

16.89 g (10 mmol) of Ir-3-10, 3 g (30 mmol) of pentane-2,4-dione, and 3.18 g of sodium carbonate anhydride were stirred under reflux in 150 ml of ethoxyethanol for 48 hours and cooled to room temperature. The mixture was washed with water and methanol, and the resulting compound was vacuum-dried to obtain a solid. This was again washed several times with dichloromethane and washed with the addition of isopropanol. The resulting solid was columned at Hex : EA = 5 : 1 to obtain 7.80 g (43%) of crystalline Compound 3-10 of the iridium compound represented by Chemical Formula 1.

MS(FAB): 907(M ⁺ )

<Synthesis of Compounds 3-12, 26, 38, 41, 55, 62, 73, 77, 81, 107, 119, 152, 163, 189, 197, 201, 212, 224>

Synthesis of compounds 3-12, 26, 38, 41, 55, 62, 73, 77, 81, 107, 119, 152, 163, 189, 197, 201, 212, and 224 were carried out using compounds 3-1 and 3-5. , synthesized in a similar manner to compound 3-10.

The reaction formulas of the iridium intermediates and final iridium compounds of compounds 3-12, 26, 38, 41, 55, 62, 73, 77, 81, 107, 119, 152, 163, 189, 197, 201, 212, and 224 are as follows: Same as

[Synthetic Reaction Formula of Iridium Intermediate]

[Synthetic Reaction Formula of Iridium Compound]

<Synthesis of Compound 4-101>

After injecting 5.53g (10mmol) of Intermediate-72 and 3.98g (10mmol) of Intermediate-71 under nitrogen and dissolving in 80ml 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 column to obtain 6.69g (77% yield) of compound 4-101.

Compound 4-101 MS (FAB): 869 (M ⁺ )

<Synthesis of Compound 4-103>

After injecting 5.53 g (10 mmol) of Intermediate-72 and 3.21 g (10 mmol) of Intermediate-73 under nitrogen and dissolving in 70 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 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% yield) of compound 4-103.

Compound 4-103 MS (FAB): 793 (M ⁺ )

<Synthesis of Compound 4-112>

After injecting 4.76g (10mmol) of Intermediate-75 and 3.21g (10mmol) of Intermediate-73 under nitrogen and dissolving them in 60ml of toluene, 0.18g (0.2mmol) of Pd ₂ dba _{3 and} 0.4ml (0.4mmol) 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 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 5.59g (78% yield) of compound 4-112.

Compound 4-112 MS (FAB): 716 (M ⁺ )

The compounds of Chemical Formula 4 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 of organic light emitting devices. 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). Compound 3-12 as a compound of Formula 3 of the present invention was doped by 8% as a dopant while depositing 5 nm of Compound 2-1 as a compound of Formula 2 of the present invention as a phosphorescent light emitting layer (EML1) on the hole transport layer. Compound 1-105 as a compound of Formula 1 of the present invention was doped by about 4% as a dopant while depositing 15 nm of Compound 2-69 as a compound of Formula 2 of the present invention as a fluorescent light emitting layer (EML2) on the phosphorescent light emitting layer (EML1). 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 2

In Example 1, compound 2-21 as the compound of formula 2 of the present invention was deposited at 5 nm as the phosphorescent light emitting layer (EML1), and compound 3-26 as the compound of formula 3 of the present invention was doped by about 8% as a dopant. Compound 2-69 as the compound of Chemical Formula 2 of the present invention is deposited at 15 nm as a fluorescent light emitting layer (EML2) on the phosphorescent light emitting layer (EML1), and doped with about 4% of Compound 1-1 as the compound of Chemical Formula 1 of the present invention as a dopant. An organic light emitting device of Example 2 was manufactured in the same manner as in Example 1 except for the above.

Example 3

In Example 1, while depositing 5 nm of compound 2-1 as the compound of formula 2 of the present invention as the phosphorescent light emitting layer (EML1), compound 3-12 as the compound of formula 3 of the present invention was doped by about 8% as a dopant. Compound 2-69 as the compound of Chemical Formula 2 of the present invention is deposited at 20 nm as a fluorescent light emitting layer (EML2) on the phosphorescent light emitting layer (EML1) and doped with about 4% of Compound 1-105 as the compound of Chemical Formula 1 of the present invention as a dopant. An organic light emitting device of Example 3 was prepared in the same manner as in Example 1 except for the above.

Example 4

In Example 1, while depositing 5 nm of compound 2-73 as the compound of formula 2 of the present invention as the phosphorescent light emitting layer (EML1), about 8% of compound 3-38 as the compound of formula 3 of the present invention was doped as a dopant. Compound 2-69 as the compound of Chemical Formula 2 of the present invention is deposited at 20 nm as a fluorescent light emitting layer (EML2) on the phosphorescent light emitting layer (EML1) and doped with about 4% of Compounds 1-13 as the compound of Chemical Formula 1 of the present invention as a dopant. An organic light emitting device of Example 4 was prepared in the same manner as in Example 1 except for the above.

Example 5

In Example 1, while depositing 5 nm of compound 2-1 as the compound of formula 2 of the present invention as the phosphorescent light emitting layer (EML1), compound 3-12 as the compound of formula 3 of the present invention was doped by about 8% as a dopant. Compound 2-69 as the compound of Chemical Formula 2 of the present invention is deposited at 25 nm as a fluorescent light emitting layer (EML2) on the phosphorescent light emitting layer (EML1) and doped with about 4% of Compound 1-105 as the compound of Chemical Formula 1 of the present invention as a dopant. An organic light emitting device of Example 5 was prepared in the same manner as in Example 1 except for the above.

Example 6

In Example 1, compound 2-81 as the compound of formula 2 of the present invention was deposited at 5 nm as the phosphorescent light emitting layer (EML1), and compound 3-62 as the compound of formula 3 of the present invention was doped by about 8% as a dopant. Compound 2-69 as the compound of Chemical Formula 2 of the present invention is deposited at 25 nm as a fluorescent light emitting layer (EML2) on the phosphorescent light emitting layer (EML1) and doped with about 4% of Compound 1-25 as the compound of Chemical Formula 1 of the present invention as a dopant. An organic light emitting device of Example 6 was manufactured in the same manner as in Example 1 except for the above.

Example 7

In Example 1, while depositing 1 nm of compound 2-1 as the compound of formula 2 of the present invention as the phosphorescent light emitting layer (EML1), compound 3-12 as the compound of formula 3 of the present invention was doped by about 8% as a dopant. Compound 1-105 as a compound of Formula 1 of the present invention is doped by 4% as a dopant while depositing 10 nm of Compound 2-69 as the compound of Formula 2 of the present invention as a fluorescent light emitting layer (EML2) on the phosphorescent light emitting layer (EML1). An organic light emitting device of Example 7 was manufactured in the same manner as in Example 1 except for the above.

Example 8

In Example 1, while depositing 1 nm of compound 2-92 as the compound of formula 2 of the present invention as the phosphorescent light emitting layer (EML1), compound 3-107 as the compound of formula 3 of the present invention was doped by about 8% as a dopant. Compound 2-69 as the compound of Chemical Formula 2 of the present invention is deposited at 10 nm as a fluorescent light emitting layer (EML2) on the phosphorescent light emitting layer (EML1) and doped with about 4% of Compound 1-37 as the compound of Chemical Formula 1 of the present invention as a dopant. An organic light emitting device of Example 8 was manufactured in the same manner as in Example 1 except for the above.

Example 9

In Example 1, while depositing 1 nm of compound 2-1 as the compound of formula 2 of the present invention as the phosphorescent light emitting layer (EML1), compound 3-12 as the compound of formula 3 of the present invention was doped by about 8% as a dopant. Compound 2-69 as the compound of Chemical Formula 2 of the present invention is deposited at 25 nm as a fluorescent light emitting layer (EML2) on the phosphorescent light emitting layer (EML1) and doped with about 4% of Compound 1-105 as the compound of Chemical Formula 1 of the present invention as a dopant. An organic light emitting device of Example 9 was prepared in the same manner as in Example 1 except for the above.

Example 10

In Example 1, while depositing 1 nm of compound 2-116 as the compound of formula 2 of the present invention as the phosphorescent light emitting layer (EML1), compound 3-119 as the compound of formula 3 of the present invention was doped by about 8% as a dopant. Compound 2-69 as the compound of Formula 2 of the present invention is deposited at 25 nm as a fluorescent light emitting layer (EML2) on the phosphorescent light emitting layer (EML1), and doped with about 4% of Compound 1-49 as the compound of Formula 1 of the present invention as a dopant. An organic light emitting device of Example 10 was manufactured in the same manner as in Example 1 except for the above.

Example 11

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). Compound 1-105 as a compound of Formula 1 of the present invention was doped by about 4% as a dopant while depositing 15 nm of Compound 2-69 as a compound of Formula 2 of the present invention as a fluorescent light emitting layer (EML1) on the hole transport layer. Compound 3-12 as a compound of Chemical Formula 3 of the present invention was doped by 8% as a dopant while depositing 5 nm of Compound 2-1 as a compound of Chemical Formula 2 of the present invention as a phosphorescent light emitting layer (EML2) on the fluorescent light emitting layer (EML1). 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 12

In Example 11, while depositing 15 nm of compound 2-69 as the compound of formula 2 of the present invention as the fluorescent light emitting layer (EML1), compound 1-61 as the compound of formula 1 of the present invention was doped by about 4% as a dopant. Compound 3-152 as a compound of Chemical Formula 3 of the present invention is doped by 8% as a dopant while depositing 5 nm of Compound 2-21 as the compound of Chemical Formula 2 of the present invention as a phosphorescent light emitting layer (EML2) on the fluorescent light emitting layer (EML1). An organic light emitting device of Example 12 was manufactured in the same manner as in Example 11 except for the above.

Example 13

In Example 11, compound 1-105 as a compound of formula 1 of the present invention was doped by 4% as a dopant while depositing 20 nm of compound 2-69 as a compound of formula 2 of the present invention as the fluorescent light emitting layer (EML1). Compound 2-1 as the compound of Chemical Formula 2 of the present invention was deposited at 5 nm as a phosphorescent light emitting layer (EML2) on the fluorescent light emitting layer (EML1), and Compound 3-12 as the compound of Chemical Formula 3 of the present invention was doped by about 8% as a dopant. An organic light emitting device of Example 13 was prepared in the same manner as in Example 11 except for the above.

Example 14

In Example 11, while depositing 20 nm of compound 2-69 as the compound of formula 2 of the present invention as the fluorescent light emitting layer (EML1), compound 1-73 as the compound of formula 1 of the present invention was doped by about 4% as a dopant. Compound 3-163 as a compound of Formula 3 of the present invention is doped by 8% as a dopant while depositing 5 nm of Compound 2-73 as a compound of Formula 2 of the present invention as a phosphorescent light emitting layer (EML2) on the fluorescent light emitting layer (EML1). An organic light emitting device of Example 14 was manufactured in the same manner as in Example 11 except for the above.

Example 15

In Example 11, compound 1-105 as a compound of formula 1 of the present invention was doped by 4% as a dopant while depositing 25 nm of compound 2-69 as a compound of formula 2 of the present invention as the fluorescent light emitting layer (EML1). Compound 2-1 as the compound of Chemical Formula 2 of the present invention was deposited at 5 nm as a phosphorescent light emitting layer (EML2) on the fluorescent light emitting layer (EML1) while doping with about 8% of Compound 3-12 as the compound of Chemical Formula 3 of the present invention as a dopant. An organic light emitting device of Example 15 was manufactured in the same manner as in Example 11 except for the above.

Example 16

In Example 11, while depositing 25 nm of compound 2-69 as the compound of formula 2 of the present invention as the fluorescent light emitting layer (EML1), compound 1-75 as the compound of formula 1 of the present invention was doped by about 4% as a dopant. Compound 3-197 as a compound of Formula 3 of the present invention is doped by 8% as a dopant while depositing 5 nm of compound 2-81 as a compound of Formula 2 of the present invention as a phosphorescent light emitting layer (EML2) on the fluorescent light emitting layer (EML1). An organic light emitting device of Example 16 was prepared in the same manner as in Example 11 except for the above.

Example 17

In Example 11, compound 1-105 as a compound of formula 1 of the present invention was doped by 4% as a dopant while depositing 10 nm of compound 2-69 as the compound of formula 2 of the present invention as the fluorescent light emitting layer (EML1). Compound 2-1 as the compound of Chemical Formula 2 of the present invention is deposited at a thickness of 1 nm as a phosphorescent light emitting layer (EML2) on the fluorescent light emitting layer (EML1) and doped with about 8% of Compound 3-12 as the compound of Chemical Formula 3 of the present invention as a dopant. An organic light emitting device of Example 17 was manufactured in the same manner as in Example 11 except for the above.

Example 18

In Example 11, while depositing 10 nm of compound 2-69 as the compound of formula 2 of the present invention as the fluorescent light emitting layer (EML1), compound 1-87 as the compound of formula 1 of the present invention was doped by about 4% as a dopant. Compound 2-92 as the compound of Chemical Formula 2 of the present invention is deposited at 1 nm as a phosphorescent light emitting layer (EML2) on the fluorescent light emitting layer (EML1), and compound 3-201 as the compound of Chemical Formula 3 of the present invention is doped by about 8% as a dopant. An organic light emitting device of Example 18 was manufactured in the same manner as in Example 11 except for the above.

Example 19

In Example 11, compound 1-105 as a compound of formula 1 of the present invention was doped by 4% as a dopant while depositing 25 nm of compound 2-69 as a compound of formula 2 of the present invention as the fluorescent light emitting layer (EML1). Compound 2-1 as the compound of Chemical Formula 2 of the present invention is deposited at a thickness of 1 nm as a phosphorescent light emitting layer (EML2) on the fluorescent light emitting layer (EML1) and doped with about 8% of Compound 3-12 as the compound of Chemical Formula 3 of the present invention as a dopant. An organic light emitting device of Example 19 was manufactured in the same manner as in Example 11 except for the above.

Example 20

In Example 11, compound 2-69 as the compound of formula 2 of the present invention was deposited at 25 nm as the fluorescent light emitting layer (EML1), and compound 1-121 as the compound of formula 1 of the present invention was doped by about 4% as a dopant. Compound 3-224 as a compound of Formula 3 of the present invention is doped by 8% as a dopant while depositing 1 nm of compound 2-116 as a compound of Formula 2 of the present invention as a phosphorescent light emitting layer (EML2) on the fluorescent light emitting layer (EML1). An organic light emitting device of Example 20 was manufactured in the same manner as in Example 11 except for the above.

Example 21

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, Compound-4-103 as a compound of Formula 4 was deposited to a thickness of 120 nm as a hole transport layer (HTL). Compound 3-12 as a compound of Formula 3 of the present invention was doped by 8% as a dopant while depositing 5 nm of Compound 2-1 as a compound of Formula 2 of the present invention as a phosphorescent light emitting layer (EML1) on the hole transport layer. Compound 1-105 as a compound of Formula 1 of the present invention was doped by about 4% as a dopant while depositing 15 nm of Compound 2-69 as a compound of Formula 2 of the present invention as a fluorescent light emitting layer (EML2) on the phosphorescent light emitting layer (EML1). 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 22

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, Compound-4-103 as a compound of Formula 4 was deposited to a thickness of 120 nm as a hole transport layer (HTL). Compound 1-105 as a compound of Formula 1 of the present invention was doped by about 4% as a dopant while depositing 15 nm of Compound 2-69 as a compound of Formula 2 of the present invention as a fluorescent light emitting layer (EML1) on the hole transport layer. Compound 3-12 as a compound of Chemical Formula 3 of the present invention was doped by 8% as a dopant while depositing 5 nm of Compound 2-1 as a compound of Chemical Formula 2 of the present invention as a phosphorescent light emitting layer (EML2) on the fluorescent light emitting layer (EML1). 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

20 nm of 9,10-bis(2-naphthyl)anthracene (ADN) is deposited on the hole transport layer without using a phosphorescent light emitting layer, and 2,5,8,11-Tetra-butyl-Perylene is used as a dopant. An organic light emitting device was manufactured in the same manner as in Example 1 except for using (t-Bu-Perylene).

Comparative Example 2

Compound 1-105 as the compound of Formula 1 of the present invention is used as a dopant at about 4% while depositing 20 nm of Compound 2-69 as the compound of Formula 2 of the present invention as a fluorescent light emitting layer (EML) without using a phosphorescent light emitting layer on the hole transport layer. An organic light emitting device was manufactured in the same manner as in Example 1 except for doping.

Comparative Example 3

Compound 1-105 as the compound of Formula 1 of the present invention is used as a dopant at about 4% while depositing 20 nm of Compound 2-69 as the compound of Formula 2 of the present invention as a fluorescent light emitting layer (EML) without using a phosphorescent light emitting layer on the hole transport layer. An organic light emitting device was manufactured in the same manner as in Example 21 except for doping.

Common compounds used in Examples 1 to 20, 21 and 22 and Comparative Examples 1, 2 and 3 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 10 and Comparative Examples 1 and 2

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

EQE
(%) CIE_x CIE_y T ₉₅ (hours) Example 1 16.8 0.143 0.062 317 Example 2 16.7 0.143 0.063 303 Example 3 16.4 0.141 0.060 289 Example 4 16.5 0.142 0.061 295 Example 5 15.7 0.140 0.058 274 Example 6 15.8 0.140 0.058 292 Example 7 14.2 0.137 0.054 255 Example 8 14.1 0.138 0.054 264 Example 9 12.1 0.135 0.053 228 Example 10 12.3 0.136 0.054 250 Comparative Example 1 6.2 0.135 0.063 94 Comparative Example 2 9.3 0.135 0.053 169

As a result of the above experiment, the multilayer light emitting layer using the organic compound of Formula 3 of the present invention as a phosphorescent dopant, the organic compound of Formula 2 of the present invention as a host, and the organic compound of Formula 1 of the present invention together as a fluorescent dopant The organic light emitting devices of Examples 1 to 10 showed improved results in efficiency and lifetime characteristics compared to the conventional organic light emitting device of Comparative Example 1.

In addition, an embodiment of a multi-layer light emitting layer in which the organic compound of Formula 3 of the present invention is used as a phosphorescent dopant, the organic compound of Formula 2 of the present invention is used as a host, and the organic compound of Formula 1 of the present invention is used together as a fluorescent dopant. Organic light emitting diodes of 1 to 10 showed improved results in efficiency and lifetime characteristics compared to the organic light emitting diodes of a single fluorescent light emitting layer of Comparative Example 2.

In particular, as a result of measuring the afterimage lifespan (T ₉₅ ), the organic electroluminescent devices of Comparative Examples 1 and 2 had a lifespan of 200 hours or less, whereas Examples 1 to 10 had a long lifespan of 200 hours or more. In particular, it was confirmed that the organic light emitting devices of Examples 1, 2, 4 and 6 had a long lifespan of 290 hours or more.

Therefore, an organic electric field of a multi-layer light emitting layer using the organic compound of Chemical Formula 3 of the present invention as a phosphorescent dopant, the organic compound of Chemical Formula 2 of the present invention as a host, and the organic compound of Chemical Formula 1 of the present invention together as a fluorescent dopant. It can be seen that the light emitting device has excellent efficiency and lifespan characteristics.

2. Evaluation of characteristics of organic light emitting devices of Examples 11 to 20 and Comparative Examples 1 and 2

The characteristics of the organic light emitting devices prepared in Examples 11 to 20 and Comparative Examples 1 and 2 were measured at a current density of 10 mA/cm ² , and the results are shown in Table 2 below.

EQE
(%) CIE_x CIE_y T ₉₅ (hours) Example 11 17.0 0.143 0.062 349 Example 12 16.8 0.142 0.062 319 Example 13 16.6 0.141 0.060 297 Example 14 16.7 0.141 0.061 307 Example 15 15.9 0.140 0.058 282 Example 16 16.1 0.139 0.056 318 Example 17 14.3 0.137 0.054 263 Example 18 15.2 0.138 0.054 272 Example 19 12.2 0.135 0.053 235 Example 20 12.5 0.136 0.054 277 Comparative Example 1 6.2 0.135 0.063 94 Comparative Example 2 9.3 0.135 0.053 169

As a result of the above experiment, the multilayer light emitting layer using the organic compound of formula 1 of the present invention as a fluorescent dopant, the organic compound of formula 2 of the present invention as a host, and the organic compound of formula 3 of the present invention together as a phosphorescent dopant The organic light emitting devices of Examples 11 to 20 showed improved results in efficiency and lifetime characteristics compared to the conventional organic light emitting device of Comparative Example 1.

In addition, an embodiment of a multilayer light emitting layer in which the organic compound of Formula 1 of the present invention is used as a fluorescent dopant, the organic compound of Formula 2 of the present invention is used as a host, and the organic compound of Formula 3 of the present invention is used together as a phosphorescent dopant. Organic light emitting devices of 11 to 20 showed improved results in efficiency and lifetime characteristics compared to organic light emitting devices of a single fluorescent light emitting layer of Comparative Example 2.

In particular, as a result of measuring the afterimage lifespan (T ₉₅ ), the organic electroluminescent devices of Comparative Examples 1 and 2 had a lifespan of 200 hours or less, whereas Examples 11 to 20 had a long lifespan of 200 hours or more. In particular, it was confirmed that the organic light emitting devices of Examples 11, 12, 14 and 16 had a long lifespan of 300 hours or more.

3. Evaluation of characteristics of organic light emitting devices of Examples 1, 11, 21, 22 and Comparative Example 3

The characteristics of the organic light emitting devices prepared in Examples 1, 11, 21, and 22 and Comparative Example 3 were measured at a current density of 10 mA/cm ² , and the results are shown in Table 3 below.

EQE
(%) CIE_x CIE_y T ₉₅ (hours) Example 1 16.8 0.143 0.062 317 Example 11 17.0 0.143 0.062 349 Example 21 17.2 0.140 0.060 324 Example 22 17.5 0.140 0.059 361 Comparative Example 3 9.5 0.135 0.053 173

As a result of the experiment, the organic compound of formula 1 of the present invention was used as a fluorescent dopant, the organic compound of formula 2 of the present invention was used as a host, the organic compound of formula 3 of the present invention was used as a phosphorescent dopant, and the present invention The organic electroluminescent devices of Examples 21 and 22 of a specific combination of multilayer light emitting layers using the organic compound of Chemical Formula 4 together as a hole transport layer, as well as Comparative Example 3, using the organic compound of Chemical Formula 1 of the present invention as a fluorescent dopant, Compared to Examples 1 and 11 in which the organic compound of Formula 2 of the present invention was used as a host and the organic compound of Formula 3 of the present invention was used as a phosphorescent dopant, color coordinate change, luminous efficiency and lifespan characteristics were remarkably excellent.

Therefore, the organic electric field of a multi-layer light emitting layer using the organic compound of formula 1 of the present invention as a fluorescent dopant, the organic compound of formula 2 of the present invention as a host, and the organic compound of formula 3 of the present invention together as a phosphorescent dopant It can be seen that the light emitting device has excellent efficiency and lifespan characteristics.

Claims (8)

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 is an organic electroluminescent device, characterized in that the ratio of deuterium to hydrogen in the chemical structure is 50% or more compared to hydrogen, The organic electroluminescent device according to claim 1, characterized in that it comprises an organic compound represented by the following formula (1)
[Formula 1]

in the above formula
Ar1, Ar2, Ar3 and Ar4 are each independently 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, pyridine An aromatic hydrocarbon group having 6 to 60 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of one, pyrazinyl, pyrimidinyl, and quinolinyl,
Deuterium, hydrogen, CN, straight chain 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, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, spirobi [fluorene], carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyridine substituted with a phenyl group A heteroaromatic hydrocarbon group having 5 to 70 carbon atoms that is unsubstituted or substituted with one or more selected from the group consisting of a midinyl group and a quinolinyl group and contains one or more elements selected from the group consisting of S, O, N and Si is,
B1 and B2 are each independently selected from 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, anthra Anthracenyl, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, and It is an aromatic hydrocarbon group having 6 to 60 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of quinolinyl groups,
n and m are independently 0 and 1, respectively;
R1, R2, R3, R4, R5, R6, R7 and R8 are each independently deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , 1 to 40 carbon atoms straight-chain or branched-chain alkyl, alkoxy of 1 to 40 carbon atoms, thioalkyl of 1 to 40 carbon atoms, or cycloalkyl group of 3 to 40 carbon atoms,
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, Thioalkyl, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, di An aromatic hydrocarbon group having 6 to 60 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of benzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, and quinolinyl,
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, Thioalkyl, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, spirobi [fluorene], substituted or unsubstituted with one or more selected from the group consisting of carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl group, and quinolinyl group, and S, O, N and Si A heteroaromatic hydrocarbon group having 5 to 70 carbon atoms containing at least one element selected from the group consisting of
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, Phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with phenyl group, phenanthrenyl, pyrenyl unsubstituted or substituted with one or more selected from the group consisting of thioalkyl and cycloalkyl group having 3 to 40 carbon atoms , 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and substituted with one or more selected from the group consisting of pyrimidinyl groups is an amino group. The organic electroluminescent device according to claim 1, characterized in that it comprises an organic compound represented by the following formula (2)
[Formula 2]

in the above formula
Ar1 and Ar2 are each independently 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, bi Phenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl , 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,
Deuterium, hydrogen, CN, straight chain 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, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, spirobi [fluorene], carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyridine substituted with a phenyl group A heteroaromatic hydrocarbon group having 5 to 70 carbon atoms that is unsubstituted or substituted with one or more selected from the group consisting of a midinyl group and a quinolinyl group and contains one or more elements selected from the group consisting of S, O, N and Si is,
R1, R2, R3, R4, R5, R6, R7 and R8 are each independently deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , 1 to 40 carbon atoms straight-chain or branched-chain alkyl, alkoxy of 1 to 40 carbon atoms, thioalkyl of 1 to 40 carbon atoms, or cycloalkyl group of 3 to 40 carbon atoms,
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, Thioalkyl, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, di An aromatic hydrocarbon group having 6 to 60 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of benzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, and quinolinyl,
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, Thioalkyl, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, spirobi [fluorene], substituted or unsubstituted with one or more selected from the group consisting of carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl group, and quinolinyl group, and S, O, N and Si A heteroaromatic hydrocarbon group having 5 to 70 carbon atoms containing at least one element selected from the group consisting of
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, Phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with phenyl group, phenanthrenyl, pyrenyl unsubstituted or substituted with one or more selected from the group consisting of thioalkyl and cycloalkyl group having 3 to 40 carbon atoms , 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and substituted with one or more selected from the group consisting of pyrimidinyl groups is an amino group. The organic electroluminescent device according to claim 1, characterized in that it comprises an organic compound represented by the following formula (3)
[Formula 3]

in the above formula
M is Ir, Os or Pt;
Ar1, Ar2 and Ar3 are each independently deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, pyridine, pyrimidine, pyrazine, 1,3,5-triazine, quinolone , isoquinoline, indolizine, 1-phenyl1H-indole, 2-phenyl-2H-isoindole, benzofuran, benzo[b]thiophene, benzo[d]thiazole, 4H-quinolizine, cinnoline, furan, phthalazine, quinazoline, quinoxaline, 1,8 -naphthyridine, pteridine, thiophene, oxazole, thiazole, isoxazole, isothiazole, 1,2,3-oxadiazole, 1,2,3-thiadiazole, 1,3,4-thiadiazole, pyridazine, furo[2,3-b]pyridine , furo[2,3-c]pyridine, furo[3,2-c]pyridine furo[3,2-b]pyridine benzo[d]oxazole furo[2,3-d]pyrimidine, furo[3,2- d]pyrimidine, furo[2,3-b]pyrazine, thieno[2,3-,b]pyridine, thieno[3,2-c]pyridine, thieno[3,2-b]pyridine, benzo[d]thiazole , thieno[2,3-d]pyrimidine, thieno[2,3-d]pyridazine, thieno[2,3-b]pyrazine, benzofuro[2,3-b]pyridine, benzofuro[2,3-c]pyridine , benzofuro[3,2-c]pyridine, benzofuro[3,2-b]pyridine, benzofuro[2,3-d]pyrimidine, benzofuro[2,3-b]pyrazine, benzo[4,5]thieno[2 ,3-b]pyridine, benzo[4,5]thieno[3,2-c]pyridine, benzo[4,5]thieno[3,2-b]pyridine, benzo[4,5]thieno[3,2 -b]pyridine, benzo[4,5]thieno[2,3-d]pyrimidine, benzo[4,5]thieno[2,3-b]pyrazine, furo[2,3-b:5,4-b ']dipyridine, furo[2,3-b:4,5-c']dipyridine, furo[2,3-b:5,4-c']dipyridine, furo[2,3-b:4,5- b']dipyridine, pyrido[3',2':4,5]furo[3,2-d]pyrimidine, thieno[2,3-b:5,4-b']dipyridine, thieno[2,3- b:5,4-c']dipyridine, thieno[2,3-b:4,5-c']dipyridine, thieno[2,3-b:4,5-b']dipyridine, pyrido[3', 2':4,5]thieno[2,3-d]pyridazine, straight or branched chain alkyl of 1 to 60 carbon atoms, alkoxy of 1 to 60 carbon atoms, thioalkyl of 1 to 60 carbon atoms, or cyclo of 3 to 60 carbon atoms an alkyl group,
Deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, straight or branched chain alkyl of 1 to 60 carbon atoms, alkoxy of 1 to 60 carbon atoms, thio of 1 to 60 carbon atoms Alkyl, cycloalkyl having 3 to 60 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzo It is unsubstituted or substituted with one or more selected from the group consisting of furanyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, and quinolinyl, and selected from the group consisting of S, O, N, and Si A heteroaromatic hydrocarbon group having 5 to 80 carbon atoms containing at least one element,
Deuterium, hydrogen, F, Cl, Br, I, CN, Si(CH3)3, B(OH)2, straight or branched chain alkyl of 1 to 60 carbon atoms, alkoxy of 1 to 60 carbon atoms, thio of 1 to 60 carbon atoms phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, An amino group substituted with one or more selected from the group consisting of 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and pyrimidinyl groups am. The method of claim 2,
The organic compound is characterized in that any one of the following compounds 1-1 to 1-124.

The method of claim 3,
The organic compound is characterized in that any one of the following compounds 2-1 to 2-116.

The method of claim 4,
The organic compound is characterized in that any one of the following compounds 3-1 to 3-225.

The organic electroluminescent device according to claim 1, wherein the light emitting layer is composed of two or more layers in which a fluorescent light emitting layer having a thickness of m and a phosphorescent light emitting layer having a thickness smaller than m are attached.