TW201335116A - Amine-based compound and organic light-emitting diode including the same - Google Patents

Abstract

The present embodiments provide an amine-based compound and an organic light-emitting diode including the amine-based compound.

Description

Amine compound and organic light-emitting diode containing same

Cross-references to related applications

This application claims the Korean application filed on December 07, 2012 from the Korea Intellectual Property Office with the case number 10-2012-0012532 and June 08, 2012 to the Korea Intellectual Property Office with the case number 10-2012-0061676. Equity, the entire contents of which are incorporated herein by reference.

This embodiment relates to a compound for an organic light-emitting diode and an organic light-emitting diode comprising the same.

Organic light-emitting diodes (OLEDs) are self-luminous diodes having advantages such as wide viewing angle, good contrast, fast response, high brightness, and good driving voltage, and can provide color images.

A conventional organic light-emitting diode includes a structure having a substrate, and an anode, a hole transport layer (HTL), an emission layer (EML), an electron transport layer (ETL), and a cathode are sequentially stacked on the substrate. In this regard, the hole transport layer, the light-emitting layer and the electron transport The layer is an organic film containing an organic compound.

The principle of operation of the organic light-emitting diode having the above structure is as follows.

When a voltage is applied between the anode and the cathode, the hole injected from the anode moves to the light-emitting layer via the hole transport layer, and the electron injected from the cathode moves to the light-emitting layer via the electron transport layer. The holes are recombined with electrons in the luminescent layer to generate excitons. When the excitons fall back from the excited state to the ground state, they emit light.

Embodiments of the present invention provide an amine-based compound having a novel structure, and an organic light-emitting diode comprising the amine-based compound.

According to an aspect of the present invention, an amine compound represented by the following Chemical Formula 1 is provided:

Wherein, in Chemical Formula 1, Ar ₁ and Ar _{2 are} each independently a substituted or unsubstituted C ₆ -C ₆₀ aryl group or a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group; X ₁ is Substituted or unsubstituted C ₆ -C ₆₀ extended aryl or substituted or unsubstituted C ₂ -C ₆₀ heteroaryl; m is an integer from 1 to 5; and each substituted C ₆ -C _{a 60} aryl group, a substituted C ₂ -C ₆₀ heteroaryl group, a substituted C ₆ -C ₆₀ extended aryl group and at least one substituent of the substituted C ₂ -C ₆₀ heteroaryl group are a halogen atom; F; -Cl; -Br; -I; -CN; hydroxy; -NO ₂ ; amino group; formazan; hydrazine; hydrazine; carboxyl group or a salt thereof; sulfonic acid group or a salt thereof; C ₆ -C ₆₀ aryl)decyl; C ₁ -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl; fluorene atom, -F At least one of -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, methionyl, anthracene, fluorene, carboxy or a salt thereof, a sulfonic acid group or a salt thereof or a phosphate group or a salt thereof Substituted C ₁ -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy, C ₂ -C ₆₀ alkenyl, and C ₂ -C ₆₀ alkynyl; C ₃ -C ₆₀ cycloalkyl, C ₃ -C ₆₀ cycloalkenyl, C ₆ -C ₆₀ aryl , C ₂ -C ₆₀ heteroaryl, C ₆ -C ₆₀ aralkyl, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ aryl group; deuterium atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, formamidine, hydrazine, hydrazine, carboxyl or a salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C ₁ -C ₆₀ alkyl group, at least a fluorine (F) substituted C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₆ -C ₆₀ aryl group and a C ₂ group at least one of the substituted C ₃ -C ₆₀ cycloalkyl group -C ₆₀ heteroaryl, C ₃ -C ₆₀ cycloalkenyl, C ₆ -C ₆₀ aryl group, C2-C ₆₀ heteroaryl, C ₆ -C _{One of 60} aralkyl, C ₆ -C ₆₀ aryloxy and C ₆ -C ₆₀ arylthio, wherein at least one of Ar ₁ and Ar ₂ is selected from -F; -CN; -NO ₂ a C ₁ -C ₆₀ alkyl group substituted with at least one -F; a C ₂ -C ₆₀ heteroaryl group; and a ruthenium atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, formamidine, hydrazine, hydrazine, carboxyl or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkane substituted with at least one -F group, C ₁ -C ₆₀ alkoxy, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₆ -C ₆₀ Group and C ₂ -C ₆₀ heteroaryl groups substituted with at least one of C ₂ -C ₆₀ heteroaryl group consisting of at least one electron withdrawing substituent of C ₆ -C ₆₀ aryl group.

According to another aspect of the present invention, an organic light emitting diode includes a first electrode, a second electrode disposed relative to the first electrode, and a first electrode disposed An organic layer between the second electrode and the second electrode, the organic layer comprising at least one amine compound.

10‧‧‧Organic Luminescent Diodes

11‧‧‧Substrate

13‧‧‧First electrode

15‧‧‧Organic layer

17‧‧‧second electrode

The above and other features and advantages of the present invention will become more apparent from the detailed description of the embodiments illustrated in the accompanying drawings in which: FIG. 1 is a schematic diagram depicting the structure of an organic light emitting diode according to an embodiment.

As used herein, the <RTI ID=0.0>"and/or" </ RTI> includes any or all combinations of one or more of the associated list elements. When a phrase such as "at least one of" is recited in a list of elements, the <RTIgt;

According to an aspect of the present invention, an amine compound represented by Chemical Formula 1 is provided:

In Chemical Formula 1, Ar ₁ and Ar _{2 are} each independently a substituted or unsubstituted C ₆ -C ₆₀ aryl group or a substituted or unsubstituted C ₃ -C ₆₀ heteroaryl group; and X ₁ is a Substituted or unsubstituted C ₆ -C ₆₀ extended aryl or substituted or unsubstituted C ₂ -C ₆₀ heteroaryl, and m is an integer from 1 to 5.

Each substituted C ₆ -C ₆₀ aryl, substituted C ₂ -C ₆₀ heteroaryl, substituted C ₆ -C ₆₀ extended aryl and substituted C ₂ -C ₆₀ heteroaryl a substituent may be a halogen atom; -F; -Cl; -Br; -I; -CN; a hydroxyl group; -NO ₂ ; an amino group; a formazan group; an anthracene; an anthracene; a carboxyl group or a salt thereof; ; phosphate group or its salt; tris(C ₆ -C ₆₀ aryl)decylalkyl; C ₁ -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy, C ₂ -C ₆₀ alkenyl and C ₂ -C ₆₀ Alkynyl; through a halogen atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, methionyl, anthracene, fluorene, carboxy or a salt thereof, a sulfonic acid group or a salt thereof or a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₂ -C ₆₀ alkenyl group and a C ₂ -C ₆₀ alkynyl group substituted with at least one of a phosphate group or a salt thereof; a C ₃ -C ₆₀ ring Alkyl, C ₃ -C ₆₀ cycloalkenyl, C ₆ -C ₆₀ aryl, C ₂ -C ₆₀ heteroaryl, C ₆ -C ₆₀ aralkyl, C ₆ -C ₆₀ aryloxy, C ₆ - C ₆₀ arylthio; through a ruthenium atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, methionyl, anthracene, fluorene, carboxy or a salt thereof, sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl, with at least one (F) of the substituted C ₁ -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₆ -C ₆₀ aryl group and C ₂ -C at least one of substituents C ₆₀ heteroaryl group ₃ -C ₆₀ cycloalkyl, C ₃ -C ₆₀ cycloalkenyl, C ₆ -C ₆₀ aryl, C ₂ -C ₆₀ heteroaryl, C ₆ -C ₆₀ One of an aralkyl group, a C ₆ -C ₆₀ aryloxy group and a C ₆ -C ₆₀ arylthio group.

In the above Chemical Formula 1, at least one of Ar ₁ and Ar ₂ is a C ₁ -C ₆₀ alkyl group selected from -F; -CN; -NO ₂ ; substituted with at least one -F; C ₂ -C ₆₀ hetero Aryl; and ruthenium atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, formamidine, oxime, oxime, carboxyl or a salt thereof, sulfonic acid group or salt thereof a phosphate group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkyl group substituted with at least one -F, a C ₁ -C ₆₀ alkoxy group, a C ₂ -C ₆₀ alkenyl group, a C ₂ - C ₆₀ alkynyl group, at least one C ₆ -C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group substituted with aryl of C ₂ -C ₆₀ heteroaryl group consisting of at least one electron withdrawing substituent of C ₆ - C ₆₀ aryl.

For example, at least one of the electron withdrawing groups may be selected from: -F; -CN; -NO ₂ ; a C ₁ -C ₂₀ alkyl group substituted with at least one -F; and a ring-forming N atom a C ₂ -C ₂₀ heteroaryl; and a ring comprising a N atom and a ruthenium atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, methionyl, oxime, Anthracene, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one -F, a C ₁ -C ₂₀ alkoxy group the group consisting of the group, at least one C ₆ -C ₂₀ aryl and C ₂ -C ₂₀ heteroaryl group substituted with aryl of C ₂ -C ₂₀ heteroaryl group.

In some embodiments, at least one of the electron withdrawing groups in Chemical Formula 1 may be selected from -F; -CN; a C ₁ -C ₂₀ alkyl group substituted with at least one -F; a pyrrolyl group, a pyrazolyl group ( Pyrazolyl group), imidazolyl group, imidazolinyl group, imidazopyridinyl group, imidazopyrimidinyl group, pyridinyl group, pyrazinyl group, Pyrimidinyl group, benzoimidazolyl group, indolyl group, purinyl group, quinolinyl group, isoquinolinyl group, pyridazine (phthalazinyl group), indolizinyl group, quinazolinyl group, cinnolinyl group, indazolyl group, carazolyl group, phenazine Phenazinyl group, phenanthridinyl group, triazinyl group, pyridazinyl group, triazolyl group and tetrazolyl group, and ruthenium atoms, -F, -Cl, -Br, -I, -CN , a hydroxyl group, a -NO ₂ , an amino group, a decyl group, an anthracene, an anthracene group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₂₀ alkyl group, substituted by at least one -F C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, phenanthrenyl group, pyrenyl group, pyridyl, triazinyl and carbazolyl At least one substituted pyrrolyl, pyrazolyl, imidazolyl, imidazolinyl, imidazolidinyl, imidazopyridyl, pyridyl, pyrazinyl, pyrimidinyl, benzimidazolyl, fluorenyl, fluorenyl, Quinolinyl, isoquinolyl, pyridazinyl, pyridazinyl, quinazolinyl, porphyrinyl, oxazolyl, oxazolyl, phenazinyl, phenanthryl, triazinyl, pyridazinyl a group consisting of triazolyl and tetrazolyl.

For example, at least one of the electron withdrawing groups in Chemical Formula 1 may be selected from: F; -CN; a C ₁ -C ₂₀ alkyl group substituted with at least one -F; pyridyl, pyrazinyl, pyrimidinyl, quinolyl , isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl; and ruthenium atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, formamidine a base, an anthracene, an anthracene, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one -F, C ₁ - Pyridyl, pyrazinyl, pyrimidinyl, quinolinyl substituted with at least one of _C20 alkoxy, phenyl, naphthyl, anthracenyl, phenanthryl, anthryl, pyridyl, triazinyl and oxazolyl A group consisting of isoquinolyl, quinazolinyl, triazinyl, benzimidazolyl and oxazolyl, but is not limited thereto.

In some embodiments, at least one of the electron withdrawing groups in the above Chemical Formula 1 may be selected from -F; -CN; -CH ₂ F; -CHF ₂ ; -CF ₃ ; and from the following Chemical Formula 2 (1) to Chemical Formula 2 ( 14) The group consisting of the groups represented:

In the above Chemical Formula 2 (1) to Chemical Formula 2 (14), Z ₁₁ to Z ₁₈ may each independently be a hydrogen atom, a halogen atom, -F, -Cl, -Br, -I, -CN, a hydroxyl group, -NO ₂ , an amino group, a mercapto group, an anthracene, an anthracene, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ substituted with at least one -F Alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, phenanthryl, anthracenyl, pyridyl, triazinyl or oxazolyl.

For example, Z ₁₁ to Z ₁₈ in the above Chemical Formula 2 (1) to Chemical Formula 2 (14) may each independently be a hydrogen atom, a halogen atom, -F, -Cl, -Br, -I, -CN, a hydroxyl group. , -NO ₂ , amino, carbenyl, anthracene, anthracene, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a methoxy group , ethoxy, propoxy, butoxy, pentyloxy, phenyl, naphthyl, anthracenyl, phenanthryl, anthracenyl, pyridyl, triazinyl or oxazolyl, but are not limited thereto, * Indicates the bond position.

In the above Chemical Formula 1, at least one of Ar ₁ and Ar ₂ may be a C ₆ -C ₆₀ aryl group substituted with at least two electron withdrawing groups.

In some embodiments, at least one of Ar ₁ and Ar ₂ may be a phenyl, biphenyl, naphthyl, anthryl, phenanthryl, anthryl or fluorenyl group substituted with at least two electron withdrawing groups. ). The electron withdrawing groups may each independently be selected from the group consisting of pyridyl, pyrazinyl, pyrimidinyl, quinolyl, isoquinolyl, quinazolinyl, triazinyl, benzimidazolyl and oxazolyl; -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, methionyl, anthracene, fluorene, carboxy or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkyl substituted with at least one -F, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, phenanthryl, anthracenyl, pyridyl, three a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a pyridazinyl group, a benzimidazolyl group, and an oxazolyl group substituted with at least one of a pyridyl group and a carbazolyl group. Group.

At least one of Ar ₁ and Ar ₂ in the amine compound of the above Chemical Formula 1 is a C ₆ -C ₆₀ aryl group substituted with at least one or more electron withdrawing groups. Accordingly, the amine compound can be represented by the following Chemical Formula 1 (1) or Chemical Formula 1 (2):

In the above Chemical Formula 1 (1), Ar ₂ is a substituted or unsubstituted C ₆ -C ₂₀ aryl group or a substituted or unsubstituted C ₂ -C ₂₀ heteroaryl group. In the above Chemical Formula 1 (1) and Chemical Formula 1 (2), the A ring and the B ring are each independently a substituted C ₆ -C ₂₀ aryl group; R ₁ and R _{2 are} each independently selected from: -F; -CN; -NO ₂ ; a C ₁ -C ₆₀ alkyl group substituted with at least one -F; a C ₂ -C ₆₀ heteroaryl group; and a ruthenium atom, -F, -Cl, -Br, -I-CN, a hydroxyl group, -NO ₂ , an amino group, a decyl group, an anthracene, an anthracene group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C substituted with at least one -F _{At least 1} -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₆ -C ₆₀ aryl and C ₂ -C ₆₀ heteroaryl One of the substituted electron groups of the C ₂ -C ₆₀ heteroaryl group; and p and q are each independently an integer from 1 to 9.

The electron withdrawing groups in Chemical Formula 1(1) to Chemical Formula 1(2) are as described above, Therefore, the detailed description thereof will not be repeated here.

For example, the amine compound may be represented by the above Chemical Formula 1 (1), wherein at least one of the number of p and R ₁ in the chemical formula 1 (1) may be -CN.

In some embodiments, the amine compound may be represented by the above Chemical Formula 1 (2), wherein at least one of the number of p and the number of R ₂ and R ₂ in the chemical formula 1 (2) may be -CN.

In some embodiments, the amine compound can be from the above formula 1 (1) It is represented that the ring A in the formula 1 (1) may be a substituted phenyl group, a substituted biphenyl group, a substituted naphthyl group, a substituted indenyl group, a substituted phenanthryl group, a substituted fluorenyl group. Or substituted sulfhydryl, but is not limited to this.

In some embodiments, the amine compound can be from the above formula 1 (2) It is shown that the A ring and the B ring in the chemical formula 1 (2) may each independently be a substituted phenyl group, a substituted biphenyl group, a substituted naphthyl group, a substituted indenyl group, a substituted phenanthryl group. Substituted thiol or substituted thiol.

In some embodiments, the amine compound can be represented by the chemical formula 1 (1), wherein the A ring can be a substituted phenyl group, a substituted biphenyl group, a substituted naphthyl group, a substituted fluorenyl group, substituted Fenyl, substituted fluorenyl or substituted fluorenyl; R ₁ may be selected from pyridyl, pyrazinyl, pyrimidinyl, quinolyl, isoquinolinyl, quinazolinyl, triazinyl, benzene And imidazolyl and carbazolyl; and hydrazine atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, methyl sulfonium, hydrazine, hydrazine, carboxyl or its salt, sulfonate An acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one -F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, Pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, anthracene substituted with at least one of anthracenyl, phenanthryl, anthryl, pyridyl, triazinyl and oxazolyl At least one electron withdrawing group of the group consisting of a pyridyl group, a benzimidazolyl group, and an oxazolyl group; and p may be 2, 3 or 4, for example, may be 2.

In some other embodiments, the amine compound can be represented by the chemical formula 1 (2), wherein the A ring and the B ring can each independently be a substituted phenyl group, wherein the A ring can be a substituted phenyl group, a substituted biphenyl group. a substituted naphthyl group, a substituted indenyl group, a substituted phenanthryl group, a substituted indenyl group or a substituted indenyl group; R ₁ and R ₂ may each independently be selected from pyridinyl and pyrazinyl groups. , pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl and oxazolyl; with ruthenium atoms, -F, -Cl, -Br, -I, -CN , a hydroxyl group, a -NO ₂ , an amino group, a decyl group, an anthracene, an anthracene group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₂₀ alkyl group, substituted by at least one -F a pyridyl group substituted with at least one of C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, phenanthryl, anthracenyl, pyridyl, triazinyl and oxazolyl At least one electron group of the group consisting of pyrazinyl, pyrimidinyl, quinolyl, isoquinolinyl, quinazolinyl, pyridazinyl, benzimidazolyl and oxazolyl; and p and q are Each independently is an integer of 2, 3 or 4, For Example, it can be an integer of 2 are all.

At least one of Ar ₁ and Ar ₂ in the above Chemical Formula 1 may be a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, an anthracenyl group or a fluorenyl group substituted with at least one of the above-mentioned electron withdrawing groups.

In the above Chemical Formula 1, Ar ₁ and Ar ₂ may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted pentalenyl group, substituted or unsubstituted. An indenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted azulenyl group, a substituted or unsubstituted heptalenyl group, Substituted or unsubstituted dicyclohexadienyl group, substituted or unsubstituted acenaphthyl group, substituted or unsubstituted thiol group, substituted or unsubstituted a phenalenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted propylanthenyl group, substituted Or unsubstituted terphenylenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted fused tetraphenyl ( Naphthacenyl group), substituted or unsubstituted picenyl group, Alternate or unsubstituted perylenyl group, substituted or unsubstituted pentaphenyl group, substituted or unsubstituted hexacenyl group, substituted or unsubstituted Pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted imidazolinyl, substituted or unsubstituted imidazolidinyl, substituted or Unsubstituted imidazolidinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted benzimidazolyl , substituted or unsubstituted fluorenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted a pyridazinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted porphyrin group, substituted or unsubstituted Carbazolyl, substituted or unsubstituted carbazolyl, Alken or unsubstituted phenazinyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyranyl group, substituted or unsubstituted chromenyl group Substituted or unsubstituted furanyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted thienyl group, substituted or unsubstituted Substituted benzothienyl group, substituted or unsubstituted isothiazolyl group, substituted or unsubstituted benzoimidazolyl group, substituted or unsubstituted Isozolyl group, substituted or unsubstituted dibenzothienyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted three Azinyl, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazolyl, substituted or unsubstituted tetrazole Substituted or unsubstituted morpholine Phenanthrolinyl group. At least one of Ar ₁ and Ar ₂ may be a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, an anthracenyl group or an anthracenyl group substituted with at least one of the above-mentioned electron withdrawing groups.

For example, Ar ₁ and Ar ₂ in the above Chemical Formula 1 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, Substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted tert-triphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted fluorenyl , substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted Carbazolyl, substituted or unsubstituted triazinyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted morpholine base. At least one of Ar ₁ and Ar ₂ may be a C ₁ -C ₂₀ alkyl group selected from -F; -CN; substituted with at least one -F; pyridyl, pyrazinyl, pyrimidinyl, quinolyl, iso a quinolyl group, a quinazolinyl group, a triazinyl group, a benzimidazolyl group and a carbazolyl group; and a ruthenium atom, -F, -Cl, -Br, -I, -CN, a hydroxyl group, -NO ₂ , an amino group, Mercapto, anthracene, anthracene, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one -F, C Pyridyl, pyrazinyl, pyrimidinyl, quinolin substituted with at least one of ₁ -C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, phenanthryl, anthryl, pyridyl, triazinyl and oxazolyl At least one electron-substituted phenyl group, biphenyl group, naphthyl group, fluorenyl group substituted with a group consisting of a phenyl group, an isoquinolyl group, a quinazolinyl group, a triazinyl group, a benzimidazolyl group, and a carbazolyl group Fisino, thiol or sulfhydryl.

In some embodiments, Ar ₁ and Ar ₂ in Chemical Formula 1 may be bonded together by a single bond.

In some embodiments, the amine compound can be represented by any one of the following Chemical Formula 1A to Chemical Formula 1J:

Ar ₂ in Chemical Formula 1A to Chemical Formula 1I may be the same as those described above in connection with other chemical formulas.

At least one of R ₁₁ to R ₁₅ in Chemical Formula 1A and Chemical Formula 1B, at least one of Chemical Formula 1C and at least one of R ₁₁ to R ₁₇ in Chemical Formula 1D, and at least one of Chemical Formula 1E and R ₁₁ to R ₁₈ in Chemical Formula 1J At least one of R ₁₁ to R ₁₉ in the chemical formula 1F and the chemical formula 1G, and the chemical formula 1H and the chemical formula 1I may each independently be selected from C ₁ - which is substituted by -F; -CN; -NO ₂ ; at least one -F; C ₆₀ alkyl; C ₂ -C ₆₀ heteroaryl; and ruthenium atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, formamyl, oxime, oxime, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkyl group substituted with at least one -F, a C ₁ -C ₆₀ alkoxy group, group C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₆ -C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl groups substituted with at least one of C ₂ -C ₆₀ heteroaryl group of Pull the electronic base.

For example, at least one of R ₁₁ to R ₁₅ in Chemical Formula 1A and Chemical Formula 1B, at least one of Chemical Formula 1C and R ₁₁ to R ₁₇ in Chemical Formula 1D, and Chemical Formula 1E and R ₁₁ to R _{18 in} Chemical Formula 1J At least one of at least one of Formula 1F and Formula 1G, and at least one of R ₁₁ to R ₁₉ of Formula 1H and Formula 1I may each independently be selected from C ₁ - substituted by -F; -CN; substituted by at least one -F C ₂₀ alkyl; pyridyl, pyrazinyl, pyrimidinyl, quinolyl, isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl and oxazolyl; fluorene atom, -F, - Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, formamidine, oxime, oxime, carboxyl or a salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C ₁ -C ₂₀ Alkyl, C ₁ -C ₂₀ alkyl substituted with at least one -F, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, phenanthryl, anthryl, pyridyl, triazinyl and anthracene a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a pyridazinyl group, a triazinyl group, a benzimidazolyl group, and an oxazolyl group substituted with at least one of an azolyl group The group pulls the electronic base, but is not limited to this

In some embodiments, Ar ₂ in Chemical Formula 1A to Chemical Formula 1I may be, but is not limited to, via -F; -CN; C ₁ -C ₂₀ alkyl substituted with at least one -F; pyridyl, pyrazinyl, Pyrimidinyl, quinolyl, isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl and oxazolyl; with ruthenium atoms, -F, -Cl, -Br, -I, -CN, a hydroxyl group, -NO ₂ , an amino group, a decyl group, an anthracene, an anthracene group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C substituted with at least one -F _a pyridyl group substituted with at least one of ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, phenanthryl, anthracenyl, pyridyl, triazinyl and oxazolyl, At least one electron-substituted benzene group of pyrazinyl, pyrimidinyl, quinolyl, isoquinolyl, quinazolinyl, pyridazinyl, triazinyl, benzimidazolyl and oxazolyl groups Base, biphenyl, naphthyl, anthracenyl, phenanthryl, anthracenyl or fluorenyl.

In some embodiments, the amine compound can be represented by the following Chemical Formula 1A-(1) or Chemical Formula 1A-(2):

In Chemical Formula 1A-(1) and Chemical Formula 1A-(2), R ₁₂ , R ₁₄ , R ₂₂ and R ₂₄ may each independently be selected from pyridinyl, pyrazinyl, pyrimidinyl, quinolyl, iso-quine. Alkyl, quinazolinyl, triazinyl, benzimidazolyl and oxazolyl; with ruthenium atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, A Anthracenyl, anthracene, anthracene, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one -F, C ₁ Pyridyl, pyrazinyl, pyrimidinyl, quinoline substituted with at least one of -C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, phenanthryl, anthryl, pyridyl, triazinyl and oxazolyl An electron withdrawing group of a group consisting of a group consisting of a quinolyl group, an isoquinolyl group, a quinazolinyl group, a pyridazinyl group, a benzimidazolyl group, and a carbazolyl group; and Ar ₂ may be a substituted or unsubstituted phenyl group, substituted Or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, Substituted or unsubstituted thiol.

In some embodiments, R ₁₂ , R ₁₄ , R ₂₂ and R _{24 in} Formula 1A-(1) and Formula 1A-(2) may each independently be selected from -F; -CN; -CH ₂ F; CHF ₂ ; -CF ₃ ; and a group consisting of the groups represented by the above Chemical Formula 2 (1) to Chemical Formula 2 (14).

In some embodiments, R ₁₂ , R ₁₄ , R ₂₂ and R ₂₄ in the above Chemical Formula 1A-(1) and Chemical Formula 1A-(2) may each independently be from the above Chemical Formula 2(1) to Chemical Formula 2 (8) ) the group indicated.

In some embodiments, R ₁₂ , R ₁₄ , R ₂₂ and R ₂₄ in the above Chemical Formula 1A-(1) and Chemical Formula 1A-(2) may each independently be represented by the above Chemical Formula 2 (2), but are not limited thereto. this.

In Chemical Formula 1A-(1), Ar ₂ may be a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, an anthracenyl group or a fluorenyl group, but is not limited thereto.

In Chemical Formula 1, X ₁ may be substituted or unsubstituted phenylene group, substituted or unsubstituted stretched pentalenylene group, substituted or unsubstituted Indenylene group, substituted or unsubstituted naphthylene group, substituted or unsubstituted azulenylene group, substituted or unsubstituted stretched heptane Heptalenylene group, substituted or unsubstituted indaceneylene group, substituted or unsubstituted acenaphthylene group, substituted or unsubstituted stretch Fluorylene group, substituted or unsubstituted phenalenylene group, substituted or unsubstituted phenanthrenylene group, substituted or unsubstituted thiol group ( Anthrylene group), substituted or unsubstituted fluoranthenylene group, substituted or unsubstituted stretched triphenylenylene group, substituted or unsubstituted stretch group (pyrenylene group), replaced Or unsubstituted chrysenylene group, substituted or unsubstituted naphthacenylene group, substituted or unsubstituted picenylene group, substituted or unsubstituted Substituted perylenylene group, substituted or unsubstituted pentaphenylene group, substituted or unsubstituted hexacenylene group, substituted or unsubstituted Pyrrolylene group, substituted or unsubstituted pyrazolylene group, substituted or unsubstituted imidazolylene group, substituted or unsubstituted extended imidazolinyl (imidazolinylene group), substituted or unsubstituted imidazopyridinylene group, substituted or unsubstituted imidazopyrimidinylene group, substituted or unsubstituted pyridinylene group , substituted or unsubstituted pyrazinylene group, substituted or unsubstituted pyrimidinylene group, substituted or unsubstituted thiol (ind Olylene group), substituted or unsubstituted purinylene group, substituted or unsubstituted quinolinylene group, substituted or unsubstituted phthalazinylene group , substituted or unsubstituted indolizinylene group, substituted or unsubstituted naphthyridinylene group, substituted or unsubstituted quinazolinylene group, Substituted or unsubstituted cinnolinylene group, substituted or unsubstituted indazolylene group, substituted or unsubstituted carbazolylene group, substituted Or unsubstituted phenazinylene group, substituted or unsubstituted phenanthridinylene group, substituted or unsubstituted pyranylene group, substituted or not Substituted chromenylene group, substituted or unsubstituted furanylene group, substituted or unsubstituted benzofuranylene group, substituted or unsubstituted a thienylene group, a substituted or unsubstituted benzothienylene group, a substituted or unsubstituted isothiazolylene group, a substituted or unsubstituted stretch Benzoimidazolylene group, substituted or unsubstituted isoxazolylene group, substituted or unsubstituted dibenzothienylene group, substituted or unsubstituted Dibenzofuranylene group, substituted or unsubstituted triazinylene group, substituted or unsubstituted oxadiazolylene group, substituted or unsubstituted extension Pyrazazinylene group, substituted or unsubstituted triazolylene group or substituted or unsubstituted tetrazolylene group. X ₁ in the chemical formula may have at least one substituent which may be selected from the above substituents.

In some embodiments, X ₁ in Chemical Formula 1 may be, but not limited to, substituted or unsubstituted phenyl, substituted or unsubstituted anthranyl, substituted or unsubstituted hydrazine, Substituted or unsubstituted phenanthrenyl, substituted or unsubstituted thiol, substituted or unsubstituted stretched triphenyl, substituted or unsubstituted thiol, substituted or unsubstituted Substituted extended, substituted or unsubstituted extended pyridyl, substituted or unsubstituted extended pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolin Alkyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted diphenyl And a furanyl group, a substituted or unsubstituted triazinyl group or a substituted or substituted or unsubstituted oxazinyl group, a substituted or unsubstituted zirazolyl group or a substituted or unsubstituted stretching group Azolyl.

For example, the above Chemical Formula 1 in which X ₁ may be represented by the following Chemical Formula 5 (1) to Chemical formula 5 wherein one (16) represents a group of the formula:

In Chemical Formula 5 (1) 5 to Chemical Formula (16), Z ₁ to Z ₈ may be each independently a hydrogen atom; a deuterium atom; -F; -Cl; -Br; -I ; -CN; hydroxy; -NO ₂ Amino group; formazan group; anthracene; anthracene; a carboxyl group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphate group or a salt thereof; a C ₁ - C ₂₀ alkyl group; a C ₁ - C ₂₀ alkoxy group; -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, formamidine, hydrazine, hydrazine, carboxyl or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof One substituted C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ aryl group; C ₂ -C ₂₀ heteroaryl group; ruthenium atom, -F, -Cl, -Br , -I, -CN, hydroxy, -NO ₂ , amino, formamidine, hydrazine, hydrazine, carboxyl or a salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, at least one C ₆ -C ₂₀ aryl and C ₂ -C ₂₀ heteroaryl group substituted with aryl of C ₆ -C ₂₀ aryl and C ₂ -C ₂₀ heteroaryl group.

In Chemical Formula 5(1) to Chemical Formula 5(16), * represents to Chemical Formula 1 The bonding position of the middle one, and *' indicates the bonding position of N to the chemical formula 1.

For example, Z ₁ to Z _{8 in} Chemical Formula 5(1) to Chemical Formula 5(16) may each independently be a hydrogen atom; a halogen atom; -F; -Cl; -Br; -I; -CN; a hydroxyl group; -NO ₂ ;amino group; formazan; hydrazine; hydrazine; carboxyl group or a salt thereof; sulfonic acid group or a salt thereof; phosphoric acid group or a salt thereof; methyl group, ethyl group, propyl group, butyl group and pentyl group; , ethoxy, propoxy, butoxy and pentyloxy; through a ruthenium atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, formazan, oxime, Methyl, ethyl, propyl, butyl, pentyl, methoxy, ethoxy, propoxy, substituted with at least one of hydrazine, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof , butoxy and pentyloxy; phenyl, naphthyl, anthracenyl, phenanthryl, anthracenyl, fluorenyl; pyridyl, pyrimidinyl, triazinyl, quinolyl and oxazolyl; -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, methionyl, anthracene, fluorene, carboxy or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, C ₁ -C ₂₀ alkyl group, at least one C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, anthryl, pyridyl substituted phenyl group of Naphthyl, anthryl, phenanthryl, pyrenyl, fluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl group and carbazolyl, but is not limited thereto.

In Chemical Formula 1, m is an integer from 1 to 5, and in some implementations In the example, it may be 1, 2 or 3, but is not limited thereto.

The amine compound of Chemical Formula 1 may be, for example, one of the following Compound 1 to Compound 109, but is not limited thereto:

At least one of Ar ₁ and Ar ₂ in the amine compound of the above Chemical Formula 1 is a C ₁ -C ₆₀ alkyl group substituted via at least one -F via -F; -CN; -NO ₂ ; C ₂ -C ₆₀ a heteroaryl group; and a ruthenium atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, methionyl, anthracene, fluorene, carboxy or a salt thereof, a sulfonic acid group or a salt, a phosphate group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₆ -C ₆₀ aryl group and a C at least one ₂ -C ₆₀ heteroaryl group substituted with aryl of C ₂ -C ₆₀ heteroaryl group consisting of at least one electron withdrawing substituent of C ₆ -C ₆₀ aryl group, a 1 'in the' following chemical formula Al The part indicated can pull electrons.

The amine compound of the formula 1' has a rich naphthalene-quinone core of electrons and an Al moiety having electron-trapping ability, and thus can have good electron transporting ability. When the electron withdrawing group is a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, the substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group is indirectly bonded via a C ₆ -C ₆₀ aryl group to N of the chemical formula 1'. Thus, the organic light-emitting diode comprising the amine compound of Chemical Formula 1 can have improved efficiency characteristics. When the electron-withdrawing group is -CN, the organic light-emitting diode containing the amine compound of Chemical Formula 1 can have improved service life characteristics.

Without wishing to be bound by a particular theory, i) any of the amine-based compounds comprising a naphthalene-quinone core lacking the above-described electron withdrawing group or ii) an amine-based compound comprising a naphthalene-quinone core directly bonded to the pyridine of N The highest occupied molecular orbital (HOMO) electron density may be concentrated near the 蒽 portion. However, in the lanthanide compound of the above Chemical Formula 1, the HOMO electron density may be dispersed near the amine moiety, so that the lowest unoccupied molecular orbital (LUMO) electron density may be relatively near the 蒽. This may impart improved dipole characteristics to the amine compound of Chemical Formula 1. Thereby, the electron transporting property of the amine compound of Chemical Formula 1 can be improved.

Thus, any of the amine compounds represented by the above Chemical Formula 1 is contained The organic light emitting diode may have a low driving voltage, high brightness, high efficiency, and long life.

The amine compound of Chemical Formula 1 can be synthesized by a known organic synthesis method. to make. From the examples which will be described in detail below, those skilled in the art can understand the synthesis method of the amine compound of Chemical Formula 1.

At least one amine compound of the formula 1 can be used for organic light-emitting One of the poles is between the electrodes. For example, at least one amine compound may be in the light-emitting layer and/or between the cathode and the light-emitting layer (eg, an electron transport layer, an electron injection layer, or a functional layer having both electron transport and electron injection capabilities).

According to other aspects of the embodiment, the organic light emitting diode includes the first An electrode, a second electrode disposed relative to the first electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises at least one amine compound of the above Chemical Formula 1.

As used herein, the phrase "(eg organic layer) comprises at least one amine The term "based compound" means "the organic layer contains one or more amine compounds of the above formula 1 or at least two different amine compounds of the above formula 1."

In some embodiments, the organic layer may comprise only compound 1 as an amine. a compound. Compound 1 may be in the light-emitting layer or electron transport layer of the organic light-emitting diode. In some embodiments, the organic layer may comprise Compound 1 and Compound 3 as the amine based compound. Compound 1 and Compound 3 may be in the same layer (for example, in an electron transport layer) or may be in different layers (for example, in the light-emitting layer and the electron transport layer, respectively).

The organic layer may comprise a hole injection layer (HIL), a hole transport layer (HTL), a functional layer that combines hole injection and hole transmission capability (hereinafter referred to as H-function) Layer), buffer layer, electron blocking layer (EBL), luminescent layer (EML), hole blocking layer (HBL), electron transport layer (ETL), electron injection layer (EIL), and both electron injection and electron transport capabilities At least one layer between the functional layers (hereinafter referred to as E-functional layers).

The term "organic layer" as used herein refers to an organic light-emitting diode. A single layer and/or a plurality of layers between the first electrode and the second electrode of the body.

The organic layer may comprise a light-emitting layer, wherein at least one amine compound may It is included in the light-emitting layer.

An amine compound in the light-emitting layer can be used as a matrix. When in the luminescent layer When the amine compound is used as a matrix, the light-emitting layer may further contain a fluorescent dopant. The fluorescent dopant can be a blue fluorescent dopant. In some embodiments, an amine compound in the luminescent layer can be used as a dopant. When the amine compound in the light-emitting layer is used as a dopant, the amine compound may be a blue fluorescent dopant.

In some embodiments, the organic layer can comprise an electron transport layer, wherein At least one amine compound may be included in the electron transport layer.

1 is a cross section of an organic light emitting diode 10 according to an embodiment. schematic diagram. Hereinafter, the structure of an organic light emitting diode according to an embodiment and a method of manufacturing the same will now be described with reference to FIG.

The substrate 11 can be any base for an existing organic light emitting diode board. In some embodiments, the substrate 11 can be, for example, a glass substrate or a transparent plastic substrate that is strong in mechanical strength, thermally stable, transparent, smooth in surface, easy to handle, and waterproof.

The first electrode 13 may be formed by depositing or sputtering a first electrode forming material on the substrate 11. When the first electrode 13 is constructed as an anode, a material having a high work function can be used as the first electrode forming material to facilitate hole injection. The first electrode 13 may be a reflective electrode or a transparent electrode. Suitable first electrode forming materials include transparent and conductive materials such as ITO, IZO, SnO ₂ and ZnO. The first electrode 13 may be formed using magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag). It is a reflective electrode.

The first electrode 13 may have a single layer structure or contain at least two layers Layer structure. For example, the first electrode 13 may have a three-layer structure of ITO/silver/ITO, but is not limited thereto.

The organic layer 15 may be disposed on the first electrode 13.

The organic layer 15 may include a hole injection layer, a hole transport layer, and a buffer a layer, a light emitting layer, an electron transport layer, and an electron injecting layer.

The hole injection layer can be vacuum deposited, spin coated, cast, and blue A Bolge (LB) deposit or the like is formed on the first electrode 13.

When the hole injection layer is formed by vacuum deposition, the deposition conditions may vary depending on the compound used to form the hole injection layer, the structure and thermal characteristics required to form the hole injection layer. For example, vacuum deposition can be performed at a temperature of from about 100 ° C to about 500 ° C, a vacuum of from about 10 ^-8 torr to about 10 ^-3 torr, and a deposition rate of from about 0.01 Å / sec to about 100 Å / sec. However, the deposition conditions are not limited to this.

When the hole injection layer is formed by spin coating, the coating conditions may be It varies depending on the compound used to form the hole injection layer, the structure and thermal characteristics required to form the hole injection layer. For example, the coating speed may range from about 2,000 rpm to about 5,000 rpm and after the coating to remove the residual solvent from a heat treatment temperature of from about 80 ° C to about 200 ° C. However, the coating conditions are not limited to this.

The hole injection layer may comprise any material generally used to form the hole injection layer. An example of a material that can be used to form the hole injection layer is N,N'-biphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4, 4'-diamine (N, N '-diphenyl-N , N' -bis- [4- (phenyl-m-tolyl-amino) -phenyl] -biphenyl-4,4 '- diamine, DNTPD), phthalocyanine e.g. Phthalocyanine phthalocyanine compound, 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine, m-MTDATA , N,N'-bis(1-naphthyl)-N,N'-diphenylbenzidine (N,N'-diphenylbenzidine, NPB), TDATA, 2T -NATA, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly(3,4-vinyldioxythiophene)/poly(4-styrenesulfonic acid) (poly( 3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate)(PEDOT/PSS), polyaniline/camphor sulfonic acid (Pani/CSA) or polyaniline/poly(4-thiostyrene) (polyaniline/) Poly(4-styrenesulfonate), PANI/PSS), but is not limited thereto.

The hole injection layer may have a thickness of about 100 Å to about 10,000 Å, and In some embodiments, it can be from about 100 Å to about 1,000 Å. When the thickness of the hole injection layer is within this range, there is no need to substantially increase the driving voltage, and hole injection The layer can achieve good hole injection capability.

Then, the hole transport layer can be vacuum deposited, spin coated, cast Or a Langmuer-Broggi (LB) deposit or the like is formed on the hole injection layer. When the hole transport layer is formed using vacuum deposition or spin coating, even if the deposition or coating conditions may vary depending on the material used to form the hole transport layer, deposition or coating conditions may be used to form hole injection. Layers are similar.

A non-limiting example of a suitable hole transport material is, for example, N- N-phenylcarbazole, carbazole derivative of polyvinylcarbazole, N,N'-bis(3-methylphenyl)-N,N'-diphenyl N-[1,1-biphenyl]-4,4'-diamine (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4' -dia mine,TPD),4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA), N,N'- N,N'-diphenylbenzidine (N, N'-diphenylbenzidine), NPB).

The hole transport layer can have a thickness of from about 50 Å to about 2,000 Å, and In some embodiments, it can be from about 100 Å to about 1,500 Å. When the thickness of the hole transport layer is within this range, the drive voltage is not required to be greatly increased, and the hole transport layer can be obtained well. Good hole transmission capability.

H-functional layer (functional layer with both hole injection and hole transmission capability) At least one material from each group of the hole injection layer material and the hole transport layer material may be included. The thickness of the H-functional layer can range from about 100 Å to about 10,000 Å, and in some embodiments, can range from about 100 Å to about 1,000 Å. When the thickness of the H-functional layer is within this range, the driving voltage is not required to be greatly increased, and the H-functional layer can have good hole injection and transmission capability.

In some embodiments, at least one of the hole injection layer, the hole transport layer, and the H-functional layer may comprise at least one of a compound of Formula 300 and a compound of Formula 350:

In Chemical Formula 300 and Chemical Formula 350, Ar ₁₁ and Ar ₁₂ may each independently be a substituted or unsubstituted C ₆ -C ₆₀ extended aryl group, and Ar ₂₁ and Ar ₂₂ may each independently be substituted or unsubstituted. Substituted C ₆ -C ₆₀ aryl. Ar ₁₁ and Ar ₁₂ may each independently be a phenyl, anthracenyl, phenanthrenyl and anthracene; and a phenyl group, a naphthyl group substituted with at least one of a phenyl group, a naphthyl group and an anthracenyl group; Stretching the base, stretching the base and stretching the base. Ar ₂₁ and Ar ₂₂ may each independently be a phenyl group, a naphthyl group, a phenanthryl group and a fluorenyl group; and a phenyl group, a naphthyl group, a phenanthryl group or a fluorenyl group substituted with at least one of a phenyl group, a naphthyl group and an anthracenyl group. And one of the period of the 芘基.

In the chemical formula 300, e and f may each independently be an integer of 0 to 5, For example, it can be 0, 1, or 2. In a non-limiting embodiment, e may be 1 and f may be 0, but the disclosure is not limited thereto.

In Chemical Formula 300 and Chemical Formula 350, R ₅₁ to R ₅₈ , R ₆₁ to R ₆₉ , R ₇₁ and R ₇₂ may each independently be a hydrogen atom, a halogen atom, a halogen atom, a hydroxyl group, a cyano group, a -NO ₂ , an amino group, Mercapto, anthracene, anthracene, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl, substituted or unsubstituted C ₂ -C ₆₀ alkynyl, substituted or unsubstituted C ₁ -C ₆₀ alkoxy, substituted or unsubstituted C ₃ -C ₆₀ ring Alkyl, substituted or unsubstituted C ₆ -C ₆₀ aryl, substituted or unsubstituted C ₆ -C ₆₀ aryloxy or substituted or unsubstituted C ₆ -C ₆₀ arylthio. In some non-limiting embodiments, R ₅₁ to R _58, R ₆₁ to R _69, R ₇₁ and R ₇₂ may be each independently a hydrogen atom; a deuterium atom; a halogen atom; a hydroxyl group; a cyano group; -NO _2; an amino group; Mercapto; hydrazine; hydrazine; a carboxyl group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphate group or a salt thereof; a C ₁ -C ₁₀ alkyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, Hexyl, etc.; C ₁ -C ₁₀ alkoxy (eg methoxy, ethoxy, propoxy, butoxy, pentyloxy, etc.); ruthenium atom, halogen atom, hydroxyl group, cyano group, -NO _a C ₁ -C ₁₀ alkyl group or a C ₁ -C ₁₀ alkoxy group substituted with at least one of an amino group, a decyl group, a hydrazine, a hydrazine, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphate group or a salt thereof Base; phenyl; naphthyl; anthracenyl; fluorenyl; fluorenyl; and fluorene atom, halogen atom, hydroxyl group, cyano group, -NO ₂ , amino group, methyl sulfonyl group, hydrazine, hydrazine, carboxyl group or its salt, sulfonate a phenyl, naphthyl, anthracenyl, fluorenyl and anthracenyl group substituted with at least one of an acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group one.

In the formula 300, R ₅₉ may be phenyl; naphthyl; anthracenyl; biphenyl; pyridyl; and a ruthenium atom, a halogen atom, a hydroxyl group, a cyano group, a -NO ₂ , an amino group, a decyl group, an anthracene group, Anthracene, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, and a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group At least one of the substituted phenyl, naphthyl, anthracenyl, biphenyl or pyridyl groups.

In the embodiment, the compound of Chemical Formula 300 may be a compound represented by the following Chemical Formula 300A:

R ₅₁ , R ₆₂ , R ₆₁ and R ₅₉ in the chemical formula 300A are the same as defined above, and thus a detailed description thereof will not be provided herein.

In some non-limiting embodiments, at least one of the hole injection layer, the hole transport layer, or the H-functional layer may include at least one compound represented by the following Chemical Formula 301 to Chemical Formula 320:

At least one of a hole injection layer, a hole transport layer, or an H-functional layer In addition to the above-described known hole injecting material, hole transporting material, and/or material having both hole injection and hole transporting ability, a charge generating material may be further included to increase layer conductivity.

The charge generating material can be, for example, a p dopant. Quinine One of quinine derivative, metal oxide and cyano-containing compound, but is not limited thereto. Non-limiting examples of p dopants include, for example, tetracyanoquinonedimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-dimethyl-p-benzoquinone (2) , quinone derivative such as 3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane, F4-TCNQ); metal such as tungsten oxide, molybdenum oxide, etc. An oxide; and a cyanide-containing compound such as the following compound 200.

When the hole injection layer, the hole transport layer or the H-functional layer contains more charge When the material is produced, the charge generating material may be uniformly or unevenly dispersed in the layer.

The buffer layer can be disposed in the hole injection layer, the hole transmission layer or the H-function At least one of the layers is between the luminescent layer. The buffer layer can compensate for the optical resonance distance by the wavelength of the light emitted by the light-emitting layer, and thus can increase the efficiency. The buffer layer may comprise a well-known hole injection material or a hole transmission material. In some other embodiments, the buffer layer may include a hole injection layer and a hole transmission layer included under the buffer layer. One of the layers or the H-functional layer is of the same material.

Then, the luminescent layer can be vacuum deposited, spin coated, cast or blue Mur-Brouge (LB) deposition or the like is formed on the hole transport layer, the H-functional layer or the buffer layer. When the light-emitting layer is formed using vacuum deposition or spin coating, the deposition or coating conditions may be similar to those used to form the hole injection layer, even though the deposition or coating conditions may vary depending on the material used to form the light-emitting layer.

The light-emitting layer may contain at least one amine compound of Chemical Formula 1.

An amine compound in the light-emitting layer can be used as a dopant, such as blue firefly Light doping. The luminescent layer may further comprise a matrix in addition to the amine compound.

Examples of the substrate are Alq ₃ , ₄ , 4'-N, N'-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) ( Poly(n-vinylcarbazole), PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN), TCTA, 1,3,5-three (N-phenylbenzimidazole-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di(naphthalene- 2-tert-butyl-9, 10-di-2-naphthylanthracene (TBADN), E3, distyrylarylene (DSA), dmCBP (see chemical formula below) and the following compounds 501 to 509, But it is not limited to this.

In some embodiments, the tethering represented by the following chemical formula 400 The compound can be used as a matrix.

In Chemical Formula 400, Ar ₁₁₁ and Ar _{112 are} each independently a substituted or unsubstituted C ₆ -C ₆₀ extended aryl group; and Ar ₁₁₃ to Ar _{116 are} each independently substituted or unsubstituted C ₁ -C ₁₀ An alkyl group or a substituted or unsubstituted C ₆ -C ₆₀ aryl group; and g, h, i and j are each independently an integer of 0 to 4.

In some non-limiting embodiments, Ar ₁₁₁ and Ar _{112 in} Formula 400 may each independently be a phenyl, anthracenyl, phenanthrenyl or anthracene group; or at least a phenyl group, a naphthyl group, and an anthracenyl group. One of the substituted phenyl, anthranyl, phenanthrenyl, fluorenyl group or thiol group.

In the above chemical formula 400, g, h, i, and j may each independently be 0, 1 or 2.

In some non-limiting embodiments, Ar ₁₁₃ to Ar _{116 of the} formula 400 may each independently be a C ₁ -C ₁₀ alkyl group substituted with at least one of a phenyl group, a naphthyl group or a fluorenyl group; a phenyl group; a naphthyl group; Sulfhydryl; fluorenyl; phenanthryl; fluorenyl; hydrazine atom, halogen atom, hydroxyl group, cyano group, -NO ₂ , amino group, methionyl group, anthracene, anthracene, carboxylic acid group or a salt thereof, sulfonic acid group or a salt, a phosphate group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a phenyl, naphthyl, anthracenyl, fluorenyl, phenanthryl and anthracenyl group substituted with at least one of an anthracenyl group, a phenanthryl group and a fluorenyl group; One of them.

For example, the oxime compound of the above formula 400 may be one of the compounds represented by the following chemical formula, but is not limited thereto:

In some embodiments, the tethering represented by the following chemical formula 401 The compound can be used as a matrix.

Ar ₁₂₂ to Ar ₁₂₅ in Chemical Formula 401 can be defined as described above with respect to Ar _{113 of} Chemical Formula 400, and thus a detailed description thereof will not be provided herein.

Ar ₁₂₆ to Ar ₁₂₇ in the above Chemical Formula 401 may each independently be a C ₁ -C ₁₀ alkyl group such as a methyl group, an ethyl group or a propyl group.

In Chemical Formula 401, k and l may each independently be an integer from 0 to 4. For example 0, 1 or 2.

For example, the oxime compound of the above formula 401 may be one of the compounds represented by the following chemical formulas, but is not limited thereto:

An amine compound in the light-emitting layer can be used as a matrix. In addition to amination In addition, the luminescent layer may further comprise a dopant such as a blue dopant, a green dopant or a red dopant.

A non-limiting embodiment of blue dopant is represented by the following chemical formula Compound.

A non-limiting example of a red dopant is represented by the following chemical formula Compound. In some embodiments, the red dopant can be DCM or DCJTB as shown below.

A non-limiting example of a green dopant is represented by the following chemical formula Compound. In some embodiments, the green dopant can be C545T presented below.

A non-limiting example of a dopant that can be used for the luminescent layer is the following chemical formula Indicates the complex.

A non-limiting example of a dopant that can be used for the luminescent layer is the following chemical formula Expressed as a complex.

When the luminescent layer comprises a matrix and a dopant, the amount of dopant in the luminescent layer may be It is approximately 0.01 to 15 parts by weight based on 100 parts by weight of the substrate. However, the amount of the dopant is not limited to this range.

The thickness of the luminescent layer can range from about 100 Å to about 1,000 Å, and some In embodiments, it may range from about 200 Å to about 600 Å. When the thickness of the light-emitting layer is within this range, the light-emitting layer can obtain good light-emitting capability without greatly increasing the driving voltage.

Next, the electron transport layer may be formed on the light-emitting layer by vacuum deposition, spin coating, casting, or the like. When the electron transport layer is formed by vacuum deposition or spin coating, even if the deposition or coating conditions may vary depending on the material used to form the electron transport layer, the deposition or coating conditions may be the same as those used to form the hole injection layer. similar. The material used to form the electron transport layer may be any material known to stably transport electrons injected from an electron injecting electrode (cathode). An example of a material used to form the electron transport layer is a quinoline derivative such as tris (8-quinolinorate aluminum, Alq ₃ ), TAZ, BAlq, bis (10) -hydroxybenzo[b]quinolin)(beryllium bis(benzoquinolin-10-olate,Bebq ₂ ), 9,10-di(naphthalen-2-yl)anthracene (ADN), compound 201 and compound 202, but not Limited to this.

The electron transport layer may comprise at least one of the above amine based compounds.

When the amine compound of Chemical Formula 1 is used as a material for forming an electron transport layer, the efficiency and/or the service life of the organic light emitting diode can be improved. Containing chemistry The electron transport layer of the amine compound of Formula 1 may further comprise a metal complex such as lithium quinolate.

The electron transport layer may have a thickness of from about 100 Å to about 1,000 Å, and In some embodiments, it can be from about 150 Å to about 500 Å. When the electron transport layer is in this range, the electron transport layer can obtain satisfactory electron transport capability without significantly increasing the driving voltage.

In some embodiments, in addition to known electron transport organic compounds In addition, the electron transport layer may further comprise a metal-containing material.

The metal-containing material can be a lithium complex. A non-limiting example of a lithium complex is lithium quinolate (Liq) with the following compound 203:

Next, an electron injecting layer that assists electron injection from the cathode can be formed on On the electron transport layer. Any suitable electron injecting material can be used to form the electron injecting layer.

Examples of materials for forming the electron injecting layer are LiF, NaCl, CsF, Li ₂ O and BaO known in the art. The deposition or coating conditions used to form the electron injecting layer may vary depending on the material used to form the electron injecting layer, and the deposition or coating conditions may be similar to those used to form the hole injecting layer.

The thickness of the electron injecting layer can be from about 1 Å to about 100 Å, and is one In some embodiments, it can range from about 3 Å to about 90 Å. When the thickness of the electron injecting layer is within this range, the electron injecting layer can obtain a satisfactory electron injecting capability without greatly increasing the driving voltage.

The second electrode 17 is disposed on the organic layer 15. The second electrode 17 can be The cathode of the electron injecting electrode. The material used to form the second electrode 17 may comprise a metal having a low work function, an alloy, a conductive compound, or a mixture thereof. In this regard, the second electrode 17 may include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium- Silver (Mg-Ag) or the like, and can behave as a transparent electrode in the form of a film. In some embodiments, to fabricate a top-emitting type of light-emitting diode, the transparent electrode may comprise indium tin oxide (ITO) or indium zinc oxide (IZO).

Although the organic light-emitting device of Fig. 1 is described above, the invention is not limited thereto.

When the phosphorescent dopant is used in the light-emitting layer, the hole barrier layer may be formed between the electron transport layer and the light-emitting layer by vacuum deposition, spin coating, casting, Langmuir-Brouge (LB) deposition, or the like. Between the functional layer and the light-emitting layer to prevent triplet excitons or holes from diffusing to the electron transport layer. When the hole blocking layer is formed using vacuum deposition or spin coating, even if the deposition or coating conditions may vary depending on the material used to form the hole blocking layer, the deposition or coating conditions may be used to form a hole injection. Layers are similar. Any known hole blocking material can be used. Non-limiting examples of hole blocking materials are oxadiazole derivatives, triazole derivatives, and phenanthroline derivatives. For example, a BCP represented by the following chemical formula can be used as a material for forming a hole barrier layer.

The thickness of the hole barrier layer can range from about 20 Å to about 1,000 Å, and In some embodiments, it can be from about 30 Å to about 300 Å. When the thickness of the hole blocking layer is within this range, the hole blocking layer can have a good hole blocking capability without greatly increasing the driving voltage.

Examples of unsubstituted C ₁ -C ₆₀ alkyl (or C ₁ -C ₆₀ alkyl) used herein are C ₁ -C ₆₀ linear or branched alkyl groups such as methyl, ethyl, propyl, Isobutyl, sec-butyl, pentyl, iso-amyl and hexyl. An example of a substituted C ₁ -C ₆₀ alkyl group is at least one hydrogen atom via a ruthenium atom; -F; -Cl; -Br; -I; -CN; a hydroxyl group; -NO ₂ ; an amino group; a fluorenyl group;羧基; a carboxyl group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphate group or a salt thereof; a tri(C ₆ -C ₆₀ aryl)decyl group; a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, C ₂ -C ₆₀ alkenyl and C ₂ -C ₆₀ alkynyl; at least one hydrogen atom via a ruthenium atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, formazan a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₂ -C ₆₀ substituted with at least one of ruthenium, osmium, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof or a phosphate group or a salt thereof Alkenyl or C ₂ -C ₆₀ alkynyl; C ₃ -C ₆₀ cycloalkyl, C ₃ -C ₆₀ cycloalkenyl, C ₆ -C ₆₀ aryl, C ₂ -C ₆₀ heteroaryl, C ₆ -C ₆₀ aralkyl, C ₆ -C ₆₀ aryloxy or C ₆ -C ₆₀ arylthio; or fluorenium atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino , mercapto, anthracene, anthracene, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkyl group substituted with at least one -F, C ₁ -C ₆₀ alkoxy, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkyne a C ₃ -C ₆₀ cycloalkyl group, a C ₃ -C ₆₀ cycloalkenyl group, a C ₆ -C ₆₀ aryl group substituted with at least one of a C ₆ -C ₆₀ aryl group or a C ₂ -C ₆₀ heteroaryl group, A C ₁ -C ₆₀ alkyl group substituted with at least one of C ₂ -C ₆₀ heteroaryl, C ₆ -C ₆₀ aralkyl, C ₆ -C ₆₀ aryloxy or C ₆ -C ₆₀ arylthio.

The unsubstituted C ₁ -C ₆₀ alkoxy group (or C ₁ -C ₆₀ alkoxy group) may be a group represented by the formula -OA, wherein A is an unsubstituted C ₁ -C ₆₀ alkane as described above base. Examples of unsubstituted C ₁ -C ₆₀ alkoxy groups are methoxy group and isopropyloxy group. At least one hydrogen atom of the alkoxy group may be substituted with a substituent described above in combination with a C ₁ -C ₆₀ alkyl group.

Unsubstituted C ₂ -C ₆₀ alkenyl (or C ₂ -C ₆₀ alkenyl) is a hydrocarbon having one or more carbon-carbon double bonds at the center or terminal of the unsubstituted C ₂ -C ₆₀ alkyl group chain. Examples of alkenyl groups are ethenyl, propenyl, butenyl and the like. At least one hydrogen atom of the unsubstituted C ₂ -C ₆₀ alkenyl group may be substituted with a substituent described above in combination with a C ₁ -C ₆₀ alkyl group.

The unsubstituted C ₂ -C ₆₀ alkynyl group (C ₂ -C ₆₀ alkynyl group) is an unsubstituted C ₂ -C ₆₀ alkyl group having at least one carbon-carbon bond at its center or terminal. Examples of the unsubstituted C ₂ -C ₆₀ alkynyl group (or C ₂ -C ₆₀ alkynyl group) include an ethynyl group, a propynyl group and the like. At least one hydrogen atom in the alkynyl group may be substituted with a substituent described above in combination with a C ₁ -C ₆₀ alkyl group.

As used herein, unsubstituted C ₃ -C ₆₀ cycloalkyl refers to a cyclic, monovalent C ₃ -C ₆₀ carbon saturated hydrocarbon group. Non-limiting examples of unsubstituted C ₃ -C ₆₀ cycloalkyl are cyclopropyl, cyclobutyl, cylcopentyl, cyclohexyl, cyclooctyl . At least one hydrogen atom in the cycloalkyl group may be substituted with a substituent described above in combination with a C ₁ -C ₆₀ alkyl group.

As used herein, unsubstituted C ₃ -C ₆₀ cycloalkenyl refers to a non-aromatic, cyclic unsaturated hydrocarbon group having at least one carbon-carbon double bond. Examples of unsubstituted C ₃ -C ₆₀ cycloalkenyl groups are cyclopropenyl, cyclobutenyl, cylcopentenyl, cyclohexcenyl, cycloheptenyl. (cycloheptenyl), 1,3-cyclohexadienyl group, 1,4-cyclohexadienyl group, 2,4-cycloheptadienyl ( 2,4-cycloheptadienyl group) and 1,5-cyclooctadineyl group. At least one hydrogen atom in the cycloalkenyl group may be substituted with a substituent described above in combination with a C ₁ -C ₆₀ alkyl group.

The unsubstituted C ₆ -C ₆₀ aryl group is a monovalent group of a carbocyclic ring system having 6 to 60 carbon atoms containing at least one aromatic ring. The unsubstituted C ₆ -C ₆₀ exoaryl group is a divalent group of a carbocyclic ring system having 6 to 60 carbon atoms containing at least one aromatic ring. When the aryl group and the extended aryl group have at least two rings, they may be fused to each other through a single bond. Referring to the C ₁ -C ₆₀ alkyl group, at least one hydrogen atom of the aryl group and the extended aryl group may be substituted with a substituent described above in combination with a C ₁ -C ₆₀ alkyl group.

Examples of substituted or unsubstituted C ₆ -C ₆₀ aryl groups are phenyl, C ₁ -C ₁₀ alkylphenyl groups (for example, ethylphenyl group), C ₁ -C ₁₀ alkane An alkylbiphenyl group (eg, ethylbiphenyl group), halophenyl group (for example, o-, m- or p-fluorophenyl group and dichloro Dichlorophenyl group, dicyanophenyl group, trifluoromethoxyphenyl group, o-, m- or p-tolyl group, o-, m- or p - cumenyl group, 2,4,6-trimethylol group, phenoxyphenyl group, (α,α-dimethylphenyl)phenyl ((α, Α-dimethylbenzene)phenyl group), (N,N'-dimethyl)aminophenyl group, (N,N'-diphenyl)amine phenyl (N , N'-diphenyl)aminophenyl group), and cyclopentadienyl, fluorenyl, naphthyl, halonaphthyl group (for example, fluoronaphthyl group), C ₁ -C ₁₀ alkyl naphthalene group (alkylnaphthyl group) (e.g., methyl naphthyl _{(methylnaphthyl group)), C 1} -C 10 An alkoxynaphthyl group (eg, methoxynaphthyl group), anthracenyl, fluorenyl, p-heptatrienyl, acenaphthylenyl group, phenalenyl group, Anthraquinolyl group, methylanthryl group, phenanthryl, ternary benzene, fluorenyl, fluorenyl, ethyl-chrysenyl group, fluorenyl Group), perylenyl group, chloroperylenyl group, pentaphenyl group, fused pentaphenyl, tetraphenylenyl group, hexaphenyl group, thick six Phenyl, rubicenyl group, coronenyl group, trinaphthylenyl group, heptaphenyl group, heptalenyl group, sulfhydryl group (pyranthrenyl group) and ovalenyl group. Examples of the substituted C ₆ -C ₆₀ aryl group can be inferred from the above-mentioned unsubstituted C ₆ -C ₆₀ aryl group and the substituted C ₁ -C ₆₀ alkyl group. The substituted or unsubstituted C ₆ -C ₆₀ extended aryl group can be inferred from the above substituted or unsubstituted C ₆ -C ₆₀ aryl group.

The unsubstituted C ₂ -C ₆₀ heteroaryl group is a monovalent group having at least one aromatic ring containing at least one hetero atom selected from N, O, P and S as a ring-forming atom. The unsubstituted C ₂ -C ₆₀ heteroaryl group is a divalent group having at least one aromatic ring containing at least one hetero atom selected from N, O, P and S. In this regard, when the heteroaryl group and the heteroaryl group have at least two rings, they may be fused to each other through a single bond. At least one hydrogen atom of the heteroaryl group and the heteroaryl group may be substituted with a substituent described above in combination with a C ₁ -C ₆₀ alkyl group.

Examples of unsubstituted C ₂ -C ₆₀ heteroaryl groups are pyrazolyl, imidazolyl, oxazolyl, thiazolyl, triazolyl, tetrazolyl, oxadiazolyl, pyridyl, pyridazinyl, pyrimidine , triazinyl, oxazolyl, fluorenyl, quinolyl, isoquinolinyl, benzimidazolyl, imidazolidinyl, imidazolyl, dibenzothiophenyl, dibenzofuranyl and phenanthroline base. The unsubstituted C ₂ -C ₆₀ extending Examples of the heteroaryl group may be inferred based on the above-described substituted or non-substituted C ₂ -C ₆₀ arylene group.

The substituted or unsubstituted C ₆ -C ₆₀ aryloxy group refers to the formula -OA ₂ (wherein A ₂ is the above substituted or unsubstituted C ₆ -C ₆₀ aryl group). The substituted or unsubstituted C ₆ -C ₆₀ arylthio group means -SA ₃ (wherein A ₃ is the above substituted or unsubstituted C ₆ -C ₆₀ aryl group).

Hereinafter, the present embodiment will refer to the following synthesis example and other examples. A detailed description. However, the examples are for illustrative purposes only and are not intended to limit the scope of the embodiments.

Instance Synthesis Example 1: Synthesis of Compound 1

Compound 1 was synthesized according to the following Reaction Scheme 1:

Synthesis of Intermediate 3-1

8.60 g (20.0 mmol) of intermediate 1-1, 5.66 g (20.0 mmol) of intermediate 2-1, 1.15 g (1.0 mmol) of tetrakis(triphenylphosphine) palladium (0) (Pd(PPh ₃ ) ₄ ) and 8.29 g (60.0 mmol) of K ₂ CO _{3 were} dissolved in 50 mL of a THF/H ₂ O (2:1) mixed solution, followed by stirring the resulting solution at 70 ° C for 5 hours. The resulting mixture was cooled to room temperature, then extracted three times with 50 mL of water and 50 mL of diethyl ether. The organic layer was collected and dried over magnesium sulfate to evaporate the solvent. The residue was separated and purified by silica gel column chromatography. The intermediate was obtained to obtain 7.33 g (yield 80%) of Intermediate 3-1.

Synthesis of Compound 1

4.58 g (10.0 mmol) of intermediate 3-1, 2.85 g (12.0 mmol) of intermediate 4-1, 0.18 g (0.2 mmol) of Pd ₂ (dba) ₃ (tris(dibenzylideneacetone) 2 Palladium [(tris(dibenzylidine acetone) dipalladium(0))]), 0.04 g (0.4 mmol) of tri-tert-butylphosphine (P(t-Bu) ₃ )) and 1.44 g (15.0 mmol) NaO t Bu was dissolved in 50 mL of toluene, and then the resulting solution was refluxed for about 3 hours. The resulting mixture was cooled to room temperature and then extracted three times with 40 mL of water and 40 mL of diethyl ether. The organic layer was collected and dried over magnesium sulfate to evaporate solvent. The residue was separated and purified by silica gel column chromatography to afford 4.80 g (yield 78%) of Compound 1. This compound was verified by mass spectrometry/fast atomic impact (MS/FAB) and ¹ H NMR.

C ₄₆ H ₃₀ FN: calculated value 615.24, and measured 615.22

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.13 - 8.11 (dd, 1H), 7.87-7.85 (m, 1H), 7.84-7.80 (m, 3H), 7.72-7.69 (m, 2H), 7.67 (d, 1H), 7.65 (d, 1H), 7.59-7.56 (m, 2H), 7.54-7.51 (dd, 1H), 7.48-7.41 (m, 4H), 7.37-7.23 (m, 6H), 7.18 -7.14(m,2H), 7.09-7.06(m,1H), 6.98-6.94(m,2H), 6.85-6.83(dd,1H),6.79-6.75(m,2H)

Synthesis Example 2: Synthesis of Compound 3

4.98 g of Compound 3 (yield 80%) was prepared in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Intermediate 4-3 was used instead of Intermediate 4-1. Compound 3 was verified using MS/FAB and ¹ H NMR.

C ₄₇ H ₃₀ N ₂ : calculated value 622.24, and measured 622.23

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 7.84-7.82 (m, 2H), 7.81 (d, 1H), 7.78-7.76 (m, 1H), 7.72-7.68 (m, 3H), 7.66 (d) , 1H), 7.65 (d, 1H), 7.63-7.59 (m, 2H), 7.57-7.52 (m, 3H), 7.47-7.43 (m, 3H), 7.41-7.38 (m, 2H), 7.37-7.27 (m, 6H), 7.17 (dd, 1H), 7.13-7.09 (m, 2H), 6.99-6.95 (m, 1H), 6.88-6.85 (m, 1H)

Synthesis Example 3: Synthesis of Compound 4

4.86 g of Compound 4 (yield 75%) was prepared in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Intermediate 4-4 was used instead of Intermediate 4-1. Compound 4 was verified using MS/FAB and ¹ H NMR.

C ₄₉ H ₃₂ N ₂ : calculated 648.26, and measured 648.27

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 7.86-7.82 (m, 2H), 7.81 (d, 1H), 7.73-7.68 (m, 2H), 7.66 (d, 1H), 7.65-7.52 (m) , 3H), 7.60-7.58 (m, 2H) 7.54-7.49 (m, 3H), 7.46-7.42 (m, 3H), 7.40-7.28 (m, 8H), 6.99-6.95 (m, 1H), 6.90- 6.84 (m, 4H), 6.74 - 6.70 (m, 2H)

Synthesis Example 4: Synthesis of Compound 5

In the same manner as the preparation of Compound 1 of Synthesis Example 1, except that Intermediate 4-5 was used instead of Intermediate 4-1, 4.77 g of Compound 5 (yield 70%) was prepared. Compound 5 was verified using MS/FAB and ¹ H NMR.

C ₅₁ H ₃₆ FN: calculated value 681.28, and measured 681.27

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 7.84-7.82 (m, 2H), 7.80 (d, 1H), 7.78-7.75 (m, 1H), 7.72-7.68 (m, 2H), 7.67 (d) , 1H), 7.65 (d, 1H), 7.62-7.58 (m, 2H), 7.56-7.52 (m, 2H), 7.47-7.44 (m, 1H), 7.38-7.27 (m, 6H), 7.14-7.08 (m, 2H), 6.98-6.96 (m, 1H), 6.94-6.89 (m, 2H), 6.85-6.83 (dd, 1H), 6.79-6.77 (m, 2H), 6.75 (d, 1H), 6.73 -6.70 (m, 2H), 1.66 (s, 6H)

Synthesis Example 5: Synthesis of Compound 6

4.87 g of Compound 6 (yield 66%) was prepared in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Intermediate 4-6 was used instead of Intermediate 4-1. Compound 6 was verified using MS/FAB and ¹ H NMR.

C ₅₅ H ₃₅ N ₃ : calculated value 737.28, while measured 737.29

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 8.07-8.05 (m, 1H), 7.86-7.83 (m, 2H), 7.81 (d, 1H), 7.73-7.69 (m, 2H), 7.68-7.64 (m, 2H), 7.62-7.58 (m, 2H), 7.50-7.44 (m, 6H), 7.42-7.28 (m, 11H), 7.26-7.23 (m, 2H), 6.99-6.96 (m, 1H) , 6.90-6.86 (m, 2H), 6.81-6.78 (dd, 1H), 6.73-6.69 (m, 2H)

Synthesis Example 6: Synthesis of Compound 7

4.82 g of Compound 7 (yield 71%) was prepared in the same manner as in the preparation of Compound 1 of Synthesis Example 1 except that Intermediate 4-7 was used instead of Intermediate 4-1. Compound 7 was verified using MS/FAB and ¹ H NMR.

C ₄₉ H ₃₀ N ₂ S: calculated value 678.21, and measured 678.22

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.15-8.13 (m, 1H), 8.09-8.06 (m, 1H), 7.84-7.80 (m, 4H), 7.72-7.69 (m, 2H), 7.68 -7.64(m,2H), 7.61-7.58(m,2H),7.54-7.51(m,1H),7.47-7.41(m,2H),7.39-7.27(m,8H),7.16(d,1H) , 7.13-7.10 (dd, 1H), 7.04-7.01 (m, 1H), 6.93-6.90 (m, 2H), 6.88-6.84 (m, 2H)

Synthesis Example 7: Synthesis of Compound 11

4.17 g of Compound 11 (yield 62%) was prepared in the same manner as in the preparation of Compound 1 of Synthesis Example 1 except that Intermediate 4-11 was used instead of Intermediate 4-1. Compound 11 was verified using MS/FAB and ¹ H NMR.

C ₄₈ H ₂₉ F ₂ NO: calculated value 673.22, and measured 673.21

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 7.87-7.85 (m, 1H), 7.84-7.81 (m, 3H), 7.76-7.70 (m, 3H), 7.68-7.66 (dd, 1H), 7.65 -7.64 (m, 1H), 7.62-7.58 (m, 3H), 7.55-7.50 (m, 3H), 7.46-7.40 (m, 2H), 7.37-7.29 (m, 5H), 7.16-7.13 (dd, 1H), 7.10-7.03 (m, 2H), 6.98-6.93 (m, 2H), 6.86-6.82 (m, 2H)

Synthesis Example 8: Synthesis of Compound 13

In the same manner as the preparation of Compound 1 of Synthesis Example 1, except that Intermediate 4-13 was used instead of Intermediate 4-1, 4.52 g of Compound 13 (yield: 79%) was prepared. Compound 13 was verified using MS/FAB and ¹ H NMR.

C ₄₃ H ₂₈ N ₂ : calculated value 572.23, while measured 572.23

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 7.84-7.82 (m, 2H), 7.80 (d, 1H), 7.73-7.70 (m, 2H), 7.67 (d, 1H), 7.65 (d, 1H) ), 7.62-7.58 (m, 2H), 7.54-7.52 (dd, 1H), 7.47-7.43 (m, 2H), 7.38-7.29 (m, 7H), 7.22-7.14 (m, 4H), 7.11-7.06 (m, 1H), 6.97-6.95 (m, 1H), 6.89-6.86 (m, 1H), 6.84-6.81 (m, 2H)

Synthesis Example 9: Synthesis of Compound 14

4.29 g of Compound 14 (yield 75%) was prepared in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Intermediate 4-14 was used instead of Intermediate 4-1. Compound 14 was verified using MS/FAB and ¹ H NMR.

C ₄₃ H ₂₈ N ₂ : calculated value 572.23, while measured 572.24

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 7.86-7.82 (m, 2H), 7.81 (d, 1H), 7.73-7.68 (m, 2H), 7.66 (d, 1H), 7.65 (d, 1H ), 7.61 - 7.57 (m, 2H), 7.54 - 7.49 (m, 1H), 7.46 - 7.42 (m, 1H), 7.40 - 7.28 (m, 7H), 7.22 - 7.17 (m, 4H), 7.10 - 7.06 (m, 1H), 6.98-6.95 (m, 2H), 6.88-6.84 (m, 1H), 6.80-6.76 (m, 2H)

Synthesis Example 10: Synthesis of Compound 17

In the same manner as the preparation of Compound 1 of Synthesis Example 1, except that Intermediate 4-17 was used instead of Intermediate 4-1, 4.94 g of Compound 17 (yield: 73%) was prepared. Compound 17 was verified using MS/FAB and ¹ H NMR.

C ₄₃ H ₂₈ F ₃ N: calculated value 615.22, and measured 615.23

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 7.85-7.81 (m, 2H), 7.79 (d, 1H), 7.74-7.69 (m, 2H), 7.67 (d, 1H), 7.66 (d, 1H) ), 7.62-7.59 (m, 2H), 7.56-7.48 (m, 3H), 7.43-7.41 (m, 1H), 7.34-7.23 (m, 5H), 7.18-7.15 (m, 4H), 7.06-7.03 (m, 1H), 6.97-6.95 (m, 2H), 6.86-6.83 (m, 1H), 6.78-6.74 (m, 2H)

Synthesis Example 11: Synthesis of Compound 18

In the same manner as the preparation of Compound 1 of Synthesis Example 1, except that the intermediate 4-18 was used instead of the intermediate 4-1, 5.81 g of Compound 18 (yield 70%) was prepared. Compound 18 was verified using MS/FAB and ¹ H NMR.

C ₆₁ H ₄₂ N ₂ Si: calculated value 830.31, and measured 830.30

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 7.82-7.80 (m, 2H), 7.79 (d, 1H), 7.73-7.68 (m, 2H), 7.66 (d, 1H), 7.65 (d, 1H) ), 7.60-7.55 (m, 8H), 7.52-7.49 (m, 1H), 7.45-7.42 (m, 1H), 7.37-7.26 (m, 15H), 7.24-7.20 (m, 3H), 7.16-7.14 (m, 1H), 7.06-7.02 (m, 2H), 6.96-6.94 (m, 2H), 6.80-6.76 (m, 2H)

Synthesis Example 12: Synthesis of Compound 19

3.70 g of Compound 19 (yield 58%) was prepared in the same manner as in the preparation of Compound 1 of Synthesis Example 1 except that Intermediate 4-19 was used instead of Intermediate 4-1. Compound 19 was verified using MS/FAB and ¹ H NMR.

C ₄₂ H ₂₄ F ₅ N: calculated value 637.18, and measured 637.19

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 7.85-7.83 (m, 2H), 7.81 (d, 1H), 7.75-7.71 (m, 2H), 7.68 (d, 1H), 7.66-62 (m) , 3H), 7.56-7.54 (dd, 1H), 7.50-7.46 (m, 1H), 7.40-7.31 (m, 5H), 7.25-7.20 (m, 2H), 7.12-7.09 (m, 1H), 7.02 -6.99(m,1H), 6.92-6.88(m,4H)

Synthesis Example 13: Synthesis of Compound 20

In the same manner as the preparation of Compound 1 of Synthesis Example 1, except that Intermediate 4-20 was used instead of Intermediate 4-1, 4.54 g of Compound 20 (yield 76%) was prepared. Compound 20 was verified using MS/FAB and ¹ H NMR.

C ₄₄ H ₂₇ N ₃ : calculated value 597.22, and measured 597.23

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 7.83-7.81 (m, 2H), 7.80 (d, 1H), 7.72-7.69 (m, 2H), 7.67 (d, 1H), 7.66 (d, 1H ), 7.62 - 7.58 (m, 2H), 7.54 - 7.51 (m, 1H), 7.47 - 7.43 (m, 1H), 7.40 - 7.28 (m, 9H), 7.13 - 7.10 (m, 1H), 7.02 - 6.99 (m, 4H), 6.89-6.85 (m, 2H)

Synthesis Example 14: Synthesis of Compound 21

3.44 g of Compound 21 (yield 59%) was prepared in the same manner as in the preparation of Compound 1 of Synthesis Example 1 except that Intermediate 4-21 was used instead of Intermediate 4-1. Compound 21 was verified using MS/FAB and ¹ H NMR.

C ₄₂ H ₂₇ F ₂ N: calculated value 583.21, and measured 583.22

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 7.84-7.82 (m, 2H), 7.81 (d, 1H), 7.74-7.70 (m, 2H), 7.68 (d, 1H), 7.67 (d, 1H) ), 7.64-7.61 (m, 2H), 7.55-7.52 (dd, 1H), 7.48-7.44 (m, 1H), 7.37-7.30 (m, 5H), 7.23-7.20 (m, 4H), 7.15-7.09 (m, 5H), 7.04-7.00 (m, 2H)

Synthesis Example 15: Synthesis of Compound 22

In the same manner as the preparation of Compound 1 of Synthesis Example 1, except that the intermediate 4-22 was used instead of the intermediate 4-1, 4.03 g of Compound 22 (yield 56%) was prepared. Compound 22 was verified using MS/FAB and ¹ H NMR.

C ₅₁ H ₃₃ FN ₄ : calculated value 720.27, and measured 720.28

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.52-8.47 (m, 4H), 7.87-7.82 (m, 5H), 7.76-7.73 (m, 2H), 7.70 (d, 1H), 7.68 (d) , 1H), 7.62-7.56 (m, 5H), 7.50-7.46 (m, 1H), 7.44-7.31 (m, 7H), 7.24-7.18 (m, 2H), 7.13-7.09 (m, 2H), 7.00 -6.98(m,1H), 6.85-6.82(m,2H)

Synthesis Example 16: Synthesis of Compound 23

5.35 g of Compound 23 (yield 70%) was prepared in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Intermediate 4-23 was used instead of Intermediate 4-1. Compound 23 was verified using MS/FAB and ¹ H NMR.

C ₅₆ H ₃₆ N ₄ : calculated 764.29, and measured 764.28

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 7.85-7.82 (m, 3H), 7.81-7.77 (m, 3H), 7.74-7.70 (m, 2H), 7.69-7.67 (m, 1H), 7.66 -7.65 (m, 2H), 7.61 - 7.52 (m, 5H), 7.47-7.30 (m, 12H), 7.27-7.23 (m, 1H), 7.12-7.10 (m, 1H), 7.02-6.98 (m, 4H), 6.93-6.91 (m, 2H)

Synthesis Example 17: Synthesis of Compound 24

In the same manner as the preparation of Compound 1 of Synthesis Example 1, except that Intermediate 4-24 was used instead of Intermediate 4-1, 4.74 g of Compound 24 (yield 76%) was prepared. Compound 24 was verified using MS/FAB and ¹ H NMR.

C ₄₇ H ₃₂ N ₂ : calculated value 624.26, and measured 624.25

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.49-8.46 (m, 1H), 7.84-7.78 (m, 5H), 7.76-7.68 (m, 3H), 7.67-7.64 (m, 3H), 7.62 -7.59 (m, 2H), 7.55-7.53 (m, 1H), 7.48-7.45 (m, 1H), 7.39-7.28 (m, 6H), 7.23-7.19 (m, 4H), 7.11-7.09 (m, 1H), 7.02-6.98 (m, 3H), 6.90-6.86 (m, 2H)

Synthesis Example 18: Synthesis of Compound 25

4.93 g of Compound 25 (yield 79%) was prepared in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Intermediate 4-25 was used instead of Intermediate 4-1. Compound 25 was verified using MS/FAB and ¹ H NMR.

C ₄₇ H ₃₂ N ₂ : calculated value 624.26, and measured 624.25

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.69 (d, 1H), 8.46-8.42 (m, 1H), 7.91-7.97 (m, 1H), 7.86-7.81 (m, 3H), 7.75-7.70 (m, 2H), 7.69-7.66 (m, 2H), 7.63-7.60 (m, 2H), 7.57-7.54 (m, 1H), 7.51-7.47 (m, 2H), 7.40-7.29 (m, 7H) , 7.15-7.10(m,4H), 6.98-6.91(m,3H), 6.87-6.85(m,1H),6.82-6.78(m,2H)

Synthesis Example 19: Synthesis of Compound 26

In the same manner as the preparation of Compound 1 of Synthesis Example 1, except that Intermediate 4-26 was used instead of Intermediate 4-1, 4.99 g of Compound 26 (yield 80%) was prepared. Compound 26 was verified using MS/FAB and ¹ H NMR.

C ₄₇ H ₃₂ N ₂ : calculated value 624.26, and measured 624.25

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.56-8.53 (m, 2H), 7.85-7.82 (m, 2H), 7.80 (d, 1H), 7.73-7.69 (m, 2H), 7.68-7.66 (m, 1H), 7.65 (d, 1H), 7.61-7.51 (m, 7H), 7.47-7.44 (m, 1H), 7.38-7.26 (m, 5H), 7.18-7.13 (m, 4H), 7.09 -7.04(m,1H),6.93-6.88(m,3H),6.84-6.80(m,2H)

Synthesis Example 20: Synthesis of Compound 27

4.29 g of Compound 27 (yield 66%) was prepared in the same manner as in the preparation of Compound 1 of Synthesis Example 1 except that Intermediate 4-27 was used instead of Intermediate 4-1. Compound 27 was verified using MS/FAB and ¹ H NMR.

C ₄₈ H ₃₁ N ₃ : calculated value 649.25, and measured 649.26

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.72 (d, 1H), 8.42-8.39 (m, 1H), 7.95-7.92 (m, 1H), 7.84-7.81 (m, 2H), 7.79 (d) , 1H), 7.71-7.68 (m, 2H), 7.66 (d, 1H), 7.64 (d, 1H), 7.62-7.57 (m, 2H), 7.55-7.52 (m, 1H), 7.49-7.44 (m , 2H), 7.40-7.26 (m, 9H), 7.11-7.06 (m, 1H), 7.02-7.00 (m, 2H), 6.93-6.89 (m, 2H), 6.79-6.77 (m, 2H)

Synthesis Example 21: Synthesis of Compound 30

In the same manner as the preparation of the compound 1 of Synthesis Example 1, except that the intermediate 4-30 was used instead of the intermediate 4-1, 4.99 g of Compound 30 (yield: 74%) was prepared. Compound 30 was verified using MS/FAB and ¹ H NMR.

C ₅₁ H ₃₄ N ₂ : calculated value 674.27, while measured 674.26

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.74 (d, 1H), 8.44-8.31 (m, 1H), 8.12-8.08 (dd, 1H), 7.94-7.90 (m, 1H), 7.87-7. (m, 4H), 7.75-7.71 (m, 2H), 7.68 (d, 1H), 7.65 (d, 1H), 7.60-7.56 (m, 2H), 7.54-7.52 (m, 1H), 7.49-7.41 (m, 5H), 7.38-7.21 (m, 8H), 7.11-7.07 (m, 2H), 7.03-7.00 (m, 3H), 6.87-6.85 (dd, 1H)

Synthesis Example 22: Synthesis of Compound 31

In the same manner as the preparation of the compound 1 of Synthesis Example 1, except that the intermediate 4-31 was used instead of the intermediate 4-1, 4.98 g of Compound 31 (yield 80%) was prepared. Compound 31 was verified using MS/FAB and ¹ H NMR.

C ₄₇ H ₃₀ N ₂ : calculated value 622.24, and measured 622.23

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 8.05-8.01 (dd, 1H), 7.89-7.86 (m, 1H), 7.84-7.80 (m, 3H), 7.74-7.69 (m, 2H), 7.67 (d, 1H), 7.65 (d, 1H), 7.59-7.56 (m, 2H), 7.53-7.50 (m, 1H), 7.48-7.41 (m, 4H), 7.40-7.22 (m, 8H), 7.13 -7.09 (m, 2H), 7.05-7.03 (m, 1H), 6.96-6.93 (dd, 1H), 6.88-6.84 (m, 2H)

Synthesis Example 23: Synthesis of Compound 32

5.40 g of Compound 32 (yield 73%) was prepared in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Intermediate 4-32 was used instead of Intermediate 4-1. Compound 32 was verified using MS/FAB and ¹ H NMR.

C ₅₆ H ₄₀ N ₂ : calculated value 740.32, and measured 740.31

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.76 (d, 1H), 8.51-8.47 (dd, 1H), 7.91-7.88 (m, 1H), 7.83-7.79 (m, 3H), 7.78-7.76 (m,1H), 7.73-7.69 (m, 2H), 7.68 (d, 1H), 7.66 (d, 1H), 7.62-7.58 (m, 2H), 7.56-7.51 (m, 2H), 7.47-7.43 (m, 2H), 7.39-7.26 (m, 8H), 7.15-7.10 (m, 2H), 7.06-7.04 (m, 1H), 6.94-6.90 (m, 3H), 6.87 (d, 1H), 6.83 -6.81(m,2H),1.67(s,6H)

Synthesis Example 24: Synthesis of Compound 35

In the same manner as the preparation of Compound 1 of Synthesis Example 1, except that the intermediate 4-35 was used instead of the intermediate 4-1, 5.05 g of Compound 35 (yield 67%) was prepared. Compound 35 was verified using MS/FAB and ¹ H NMR.

C ₅₈ H ₃₈ N ₂ O: calculated 778.30, and measured 778.29

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 7.84-7.80 (m, 4H), 7.78-7.76 (m, 1H), 7.74-7.65 (m, 6H), 7.62-7.59 (m, 3H), 7.55 -7.49 (m, 4H), 7.46-7.40 (m, 3H), 7.38-7.27 (m, 5H), 7.19-7.11 (m, 2H), 7.05 (d, 1H), 6.87 (d, 1H), 6.79 -6.74(m,2H),1.64(s,6H)

Synthesis Example 25: Synthesis of Compound 36

5.80 g of Compound 36 (yield 70%) was prepared in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Intermediate 4-36 was used instead of Intermediate 4-1. Compound 36 was verified using MS/FAB and ¹ H NMR.

C ₆₃ H ₄₄ N ₂ : calculated value 828.35, and measured 828.34

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 8.08-8.04 (m, 2H), 7.85-7.82 (m, 2H), 7.81 (d, 1H), 7.77-7.75 (m, 1H), 7.72-7.68 (m, 2H), 7.68 (d, 1H), 7.66 (d, 1H), 7.62-7.58 (m, 2H), 7.56-7.52 (m, 2H), 7.47-7.43 (m, 1H), 7.36-7.26 (m, 12H), 7.15-7.10 (m, 4H), 7.04-7.02 (m, 1H), 6.99-6.91 (m, 3H), 6.89 (d, 1H), 6.85-6.81 (m, 2H), 1.65 (s, 6H)

Synthesis Example 26: Synthesis of Compound 38

In the same manner as the preparation of the compound 1 of Synthesis Example 1, except that the intermediate 4-38 was used instead of the intermediate 4-1, 5.04 g of Compound 38 (yield: 75%) was prepared. Compound 38 was verified using MS/FAB and ¹ H NMR.

C ₅₁ H ₃₂ N ₂ : calculated value 672.26, and measured 672.25

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 8.50-8.47 (m, 1H), 8.16-8.12 (m, 1H), 7.96-7.92 (m, 1H), 7.86-7.82 (m, 2H), 7.80 (d,1H), 7.73-7.69 (m, 4H), 7.67 (d, 1H), 7.65 (d, 1H), 7.60-7.52 (m, 5H), 7.47-7.41 (m, 2H), 7.39-7.28 (m, 8H), 7.22-7.18 (m, 2H), 7.07-7.03 (m, 1H), 6.97-6.95 (m, 2H)

Synthesis Example 27: Synthesis of Compound 42 Synthesis of Intermediate 3-42

The intermediate 3 - 42 was prepared in the same manner as the preparation of the intermediate 3-1 of Synthesis Example 1, except that the intermediate 2 - 42 was used instead of the intermediate 2-1.

Synthesis of Compound 42

4.54 g of the compound was prepared in the same manner as in the preparation of the compound 1 of Synthesis Example 1, except that the intermediate 3-42 and the intermediate 4-27 were used instead of the intermediate 3-1 and the intermediate 4-1. 42 (yield 65%). Compound 42 was verified using MS/FAB and ¹ H NMR.

C ₅₂ H ₃₃ N ₃ : calculated value 699.27, and measured 699.28

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.78 (d, 1H), 8.45-8.42 (m, 1H), 8.11-8.08 (m, 1H), 7.94-7.91 (m, 1H), 7.89-7.86 (m, 1H), 7.83-7.80 (m, 2H), 7, 78 (d, 1H), 7.72-7.67 (m, 3H), 7.65-7.62 (dd, 1H), 7.58-7.55 (m, 3H) , 7.54-7.52 (m, 1H), 7.48-7.43 (m, 2H), 7.40-7.33 (m, 5H), 7.31-7.27 (m, 4H), 7.18-7.15 (dd, 1H), 6.99-6.95 ( m,1H),6.82-6.79(m,2H),6.77-6.73(m,2H)

Synthesis Example 28: Synthesis of Compound 43

5.24 g of Compound 43 (yield 71%) was prepared in the same manner as in the preparation of Compound 42 of Synthesis Example 27 except for using Intermediate 4-43 instead of Intermediate 4-27. Compound 43 was verified using MS/FAB and ¹ H NMR.

C ₅₆ H ₃₈ N ₂ : calculated value 738.30, and measured 738.31

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 8.10-8.08 (m, 1H), 7.90-7.87 (m, 1H), 7.85-7.82 (m, 2H), 7.80 (d, 1H), 7.78-7.75 (m, 1H), 7.71-7.65 (m, 4H), 7.59-7.57 (m, 1H), 7.55-7.51 (m, 4H), 7.46-7.42 (m, 1H), 7.39-7.27 (m, 8H) , 7.16-7.10 (m, 3H), 6.97-6.93 (m, 1H), 6.89-6.86 (m, 2H), 6.83-6.81 (dd, 1H), 6.79 (d, 1H), 1.66 (s, 6H)

Synthesis Example 29: Synthesis of Compound 45 Synthesis of Intermediate 3-45

The intermediate 3-45 was prepared in the same manner as in the preparation of the intermediate 3-1 of Synthesis Example 1, except that the intermediate 2-45 was used instead of the intermediate 2-1.

Synthesis of Compound 45

5.38 g of the compound was prepared in the same manner as in the preparation of the compound 1 of Synthesis Example 1, except that the intermediate 3-45 and the intermediate 4-31 were used instead of the intermediate 3-1 and the intermediate 4-1. 45 (yield 80%). Compound 45 was verified using MS/FAB and ¹ H NMR.

C ₅₁ H ₃₂ N ₂ : calculated value 672.26, and measured 672.27

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.03-8.00 (m, 1H), 7.88-7.85 (m, 1H), 7.84-7.79 (m, 5H), 7.73-7.68 (m, 2H), 7.65 -7.63 (m, 1H), 7.60 (d, 1H), 7.55-7.37 (m, 9H), 7.35-7.28 (m, 5H), 7.20-7.15 (m, 2H), 7.10-7.06 (m, 1H) , 6.97-6.92 (m, 1H), 6.86-6.85 (dd, 1H), 6.80-6.77 (m, 2H)

Synthesis Example 30: Synthesis of Compound 48

5.50 g of Compound 48 (yield 76%) was prepared in the same manner as in the preparation of Compound 45 of Synthesis Example 29 except for using Intermediate 4-48 instead of Intermediate 4-31. Compound 48 was verified using MS/FAB and ¹ H NMR.

C ₅₅ H ₃₆ N ₂ : calculated value 724.29, while measured 724.30

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 8.56-8.53 (dd, 1H), 8.06-8.03 (m, 1H), 7.85-7.78 (m, 6H), 7.76-7.69 (m, 5H), 7.66 - 7.60 (m, 3H), 7.55-7.40 (m, 7H), 7.36-7.32 (m, 5H), 7.29-7.25 (m, 1H), 7.21-7.17 (m, 2H), 7.11-7.07 (m, 1H), 6.99-6.94 (m, 1H), 6.87-6.85 (dd, 1H), 6.82-6.79 (m, 2H)

Synthesis Example 31: Synthesis of Compound 51 Synthesis of Intermediate 3-51

The intermediate 3-51 was prepared in the same manner as the preparation of the intermediate 3-1 of Synthesis Example 1, except that the intermediate 2-51 was used instead of the intermediate 2-1.

Synthesis of Compound 51

4.29 g of the compound was prepared in the same manner as in the preparation of the compound 1 of Synthesis Example 1, except that the intermediate 3-51 and the intermediate 4-4 were used instead of the intermediate 3-1 and the intermediate 4-1. 51 (yield 66%). Compound 51 was verified using MS/FAB and ¹ H NMR.

C ₄₈ H ₃₁ N ₃ : calculated value 649.25, and measured 649.26

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.50 (d, 1H), 7.93-7.90 (m, 2H), 7.89-7.87 (m, 2H), 7.85 (d, 1H), 7.84-7.81 (m) , 1H), 7.74-7.69 (m, 2H), 7.65-7.61 (m, 2H), 7.56-7.49 (m, 5H), 7.46-7.37 (m, 6H), 7.36-7.34 (m, 1H), 7.32 -7.27(m,2H),7.14-7.10(m,2H),6.99-6.94 (m,2H),6.83-6.79(m,2H)

Synthesis Example 32: Synthesis of Compound 54

4.23 g of Compound 54 (yield 65%) was prepared in the same manner as in the preparation of Compound 51 of Synthesis Example 31, except that Intermediate 4-27 was used instead of Intermediate 4-4. Compound 54 was verified using MS/FAB and ¹ H NMR.

C ₄₇ H ₃₀ N ₄ : calculated value 650.25, while measured 650.24

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 8.73 (m, 1H), 8.55 (d, 1H), 8.52-8.47 (m, 1H), 7.96-7.88 (m, 5H), 7.86 (d, 1H ), 7.84-7.81 (m, 1H), 7.73-7.68 (m, 2H), 7.56-7.53 (m, 1H), 7.49-7.38 (m, 6H), 7.36-7.28 (m, 5H), 7.16-7.13 (m, 2H), 7.00-6.95 (m, 2H), 6.89-6.85 (m, 2H)

Synthesis Example 33: Synthesis of Compound 57 Synthesis of Intermediate 3-57

The intermediates 3-57 were prepared in the same manner as in the preparation of the intermediate 3-1 of Synthesis Example 1, except that the intermediate 2-57 was used instead of the intermediate 2-1.

Synthesis of Compound 57

4.97 g of the compound was prepared in the same manner as in the preparation of the compound 1 of Synthesis Example 1, except that the intermediate 3-57 and the intermediate 4-32 were used instead of the intermediate 3-1 and the intermediate 4-1. 57 (yield 67%). Compound 57 was verified using MS/FAB and ¹ H NMR.

C ₅₅ H ₃₉ N ₃ : calculated value 741.31, and measured 741.32

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 8.77 (dd, 1H), 8.52 (d, 1H), 8.23-8.20 (m, 1H), 7.93-7.90 (m, 1H), 7.89 (d, 1H ), 7.87(d,1H), 7.85-7.82(m,1H), 7.78-7.75(m,1H),7.72-7.68(m,2H),7.53-7.44(m,6H),7.42-7.23(m , 9H), 7.14-7.09 (m, 2H), 6.99-6.95 (m, 1H), 6.87-6.83 (m, 4H), 6.78 (d, 1H), 1.63 (s, 6H)

Synthesis Example 34: Synthesis of Compound 58 Synthesis of Intermediate 3-58

Intermediates 3-58 were prepared in the same manner as in the preparation of Intermediate 3-1 of Synthesis Example 1, except that Intermediate 2-58 was used instead of Intermediate 2-1.

Synthesis of Compound 58

5.67 g of the compound was prepared in the same manner as in the preparation of the compound 1 of Synthesis Example 1, except that the intermediate 3-58 and the intermediate 4-25 were used instead of the intermediate 3-1 and the intermediate 4-1. 58 (yield 81%). Compound 58 was verified using MS/FAB and ¹ H NMR.

C ₅₃ H ₃₆ N ₂ : calculated value 700.29, while measured 700.30

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.74 (dd, 1H), 8.51-8.48 (m, 1H), 7.94-7.90 (m, 1H), 7.83-7.77 (m, 5H), 7.74-7.65 (m, 6H), 7.55-7.52 (m, 1H), 7.48-7.44 (m, 4H), 7.38-7.25 (m, 7H), 7.19-7.15 (m, 2H), 7.08-7.03 (m, 3H) , 6.96-6.92 (m, 2H), 6.86-6.83 (m, 1H), 6.80-6.79 (m, 2H)

Synthesis Example 35: Synthesis of Compound 59

5.46 g of Compound 59 (yield 78%) was prepared in the same manner as in the preparation of Compound 58 of Synthesis Example 34, except that Intermediate 4-24 was used instead of Intermediate 4-25. Compound 59 was verified using MS/FAB and ¹ H NMR.

C ₅₃ H ₃₆ N ₂ : calculated value 700.29, while measured 700.29

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.58-8.54 (m, 1H), 7.86-7.80 (m, 7H), 7.78-7.70 (m, 5H), 7.68-7.65 (m, 3H), 7.54 -7.51 (m, 1H), 7.47-7.44 (m, 3H), 7.37-7.26 (m, 6H), 7.17-7.13 (m, 2H), 7.09-7.07 (m, 1H), 7.01-6.97 (m, 2H), 6.98-6.93 (m, 3H), 6.84-6.81 (m, 2H)

Synthesis Example 36: Synthesis of Compound 60

In the same manner as the preparation of the compound 58 of Synthesis Example 34, 5.08 g of Compound 60 (yield 70%) was prepared, except that Intermediate 4-27 was used instead of Intermediate 4-25. Compound 60 was verified using MS/FAB and ¹ H NMR.

C ₅₄ H ₃₅ N ₃ : calculated value 725.28, and measured 725.27

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.71 - 8.69 (m, 1H), 8.44 - 8.41 (m, 1H), 7.93 - 7.91 (m, 1H), 7.84 - 7.78 (m, 5H), 7.74 - 7.69 (m, 4H), 7.68-7.65 (m, 2H), 7.55-7.52 (m, 1H), 7.48-7.43 (m, 4H), 7.39-7.24 (m, 9H), 7.12-7.11 (m, 1H), 7.03-6.99 (m, 2H), 6.93-6.89 (m, 2H), 6.82-6.80 (m, 2H)

Synthesis Example 37: Synthesis of Compound 61

In the same manner as the preparation of Compound 58 of Synthesis Example 34, 6.04 g of Compound 61 (yield: 74%) was obtained, except that Intermediate 4-32 was used instead of Intermediate 4-25. Compound 61 was verified using MS/FAB and ¹ H NMR.

C ₆₂ H ₄₄ N ₂ : calculated value 816.35, and measured 816.34

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 8.69-8.67 (dd, 1H), 8.41-8.38 (m, 1H), 7.91-7.88 (m, 1H), 7.83-7.76 (m, 6H), 7.74 -7.68 (m, 4H), 7.67-7.64 (m, 2H), 7.56-7.51 (m, 2H), 7.47-7.44 (m, 4H), 7.37-7.25 (m, 8H), 7.15-7.09 (m, 2H), 6.99-6.94 (m, 1H), 6.90-6.86 (m, 3H), 6.83-6.79 (m, 2H), 6.77-6.76 (m, 1H), 1.64 (s, 6H)

Synthesis Example 38: Synthesis of Compound 62

5.93 g of Compound 62 (yield 79%) was prepared in the same manner as in the preparation of Compound 58 of Synthesis Example 34 except for using Intermediate 4-30 instead of Intermediate 4-25. Compound 62 was verified using MS/FAB and ¹ H NMR.

C ₅₇ H ₃₈ N ₂ : calculated value 750.30, while measured 750.29

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.51-8.48 (m, 2H), 8.17-8.15 (dd, 1H), 7.87-7.78 (m, 6H), 7.74-7.65 (m, 6H), 7.55 -7.51 (m, 5H), 7.48-7.40 (m, 6H), 7.38-7.28 (m, 5H), 7.23 (t, 1H), 7.14-7.13 (m, 1H), 7.06-7.02 (m, 2H) , 6.95-6.93 (dd, 1H), 6.88-6.85 (m, 2H)

Synthesis Example 39: Synthesis of Compound 63

5.85 g of Compound 63 (yield 78%) was prepared in the same manner as in the preparation of Compound 58 of Synthesis Example 34, except that Intermediate 4-63 was used instead of Intermediate 4-25. Compound 63 was verified using MS/FAB and ¹ H NMR.

C ₅₇ H ₃₈ N ₂ : calculated value 750.30, and measured 750.31

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.50-8.47 (m, 2H), 8.15-8.13 (dd, 1H), 7.86-7.77 (m, 6H), 7.73-7.69 (m, 4H), 7.68 -7.65 (m, 2H), 7.56-7.52 (m, 5H), 7.49-7.39 (m, 6H), 7.37-7.29 (m, 5H), 7.22 (t, 1H), 7.18-7.16 (m, 1H) , 7.11-7.07 (m, 2H), 6.96-6.94 (dd, 1H), 6.89-6.86 (m, 2H)

Synthesis Example 40: Synthesis of Compound 64

5.40 g of Compound 64 (yield 72%) was prepared in the same manner as in the preparation of Compound 58 of Synthesis Example 34, except that Intermediate 4-48 was used instead of Intermediate 4-25. Compound 64 was verified using MS/FAB and ¹ H NMR.

C ₅₇ H ₃₈ N ₂ : calculated value 750.30, and measured 750.31

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.48-8.45 (m, 1H), 8.16-8.14 (dd, 1H), 7.87-7.82 (m, 3H), 7.81-7.68 (m, 10H), 7.67 -7.64 (m, 3H), 7.54-7.51 (m, 1H), 7.48-7.40 (m, 6H), 7.38-7.21 (m, 7H), 7.09-7.07 (m, 1H), 7.01-6.99 (m, 2H), 6.95-6.94 (dd, 1H), 6.87-6.83 (m, 2H)

Synthesis Example 41: Synthesis of Compound 66

5.38 g of Compound 66 (yield 77%) was prepared in the same manner as in the preparation of Compound 58 of Synthesis Example 34, except that Intermediate 4-31 was used instead of Intermediate 4-25. Compound 66 was verified using MS/FAB and ¹ H NMR.

C ₅₃ H ₃₄ N ₂ : calculated value 698.27, and measured 698.28

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 8.06-8.04 (dd, 1H), 7.88-7.85 (m, 1H), 7.84-7.79 (m, 4H), 7.78-7.76 (m, 1H), 7.74 -7.69(m,4H), 7.67-7.64(m,2H), 7.56-7.52(m,1H), 7.48-7.29(m,13H),7.22(t,1H),7.13-7.11(m,1H) , 7.05-7.01 (m, 2H), 6.96-6.94 (dd, 1H), 6.87-6.84 (m, 2H)

Synthesis Example 42: Synthesis of Compound 67

5.36 g of Compound 67 (yield 74%) was prepared in the same manner as in the preparation of Compound 58 of Synthesis Example 34, except that Intermediate 4-67 was used instead of Intermediate 4-25. Compound 67 was verified using MS/FAB and ¹ H NMR.

C ₅₅ H ₃₆ N ₂ : calculated value 724.29, while measured 724.30

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 7.85-7.82 (m, 2H), 7.81-7.79 (m, 2H), 7.78-7.76 (m, 1H), 7.73-7.68 (m, 4H), 7.67 (d, 1H), 7.65 (d, 1H), 7.60-7.57 (m, 2H), 7.54-7.52 (dd, 1H), 7.48-7.28 (m, 13H), 7.26-7.22 (m, 2H), 7.16 -7.15 (m, 1H), 7.06-7.01 (m, 2H), 6.94-6.90 (m, 2H), 6.87-6.84 (m, 2H)

Synthesis Example 43: Synthesis of Compound 68

In the same manner as the preparation of Compound 58 of Synthesis Example 34, 5.45 g of Compound 68 (yield 78%) was prepared, except for using Intermediate 4-68 instead of Intermediate 4-25. Compound 68 was verified using MS/FAB and ¹ H NMR.

C ₅₃ H ₃₄ N ₂ : calculated value 698.27, and measured 698.28

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 7.86-7.83 (m, 2H), 7.82-7.79 (m, 2H), 7.78-7.76 (m, 2H), 7.74-7.68 (m, 4H), 7.66 -7.63 (m, 3H), 7.57-7.54 (m, 2H), 7.53-7.50 (m, 2H), 7.47-7.43 (m, 3H), 7.41-7.28 (m, 8H), 7.18-7.16 (m, 1H), 7.06-7.05 (dd, 1H), 6.92-6.88 (m, 2H), 6.85-6.82 (m, 2H)

Synthesis Example 44: Synthesis of Compound 70

In the same manner as the preparation of the compound 58 of Synthesis Example 34, 3.56 g of Compound 70 (yield: 53%) was prepared, except that Intermediate 4-70 was used instead of Intermediate 4-25. Compound 70 was verified using MS/FAB and ¹ H NMR.

C ₅₀ H ₂₉ N ₃ : calculated value 671.24, and measured 671.23

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 8.22-8.20 (m, 2H), 7.92-7.88 (m, 2H), 7.85-7.82 (m, 2H), 7.80 (d, 1H), 7.75-7.69 (m, 4H), 7.67-7.66 (dd, 1H), 7.65-7.63 (m, 2H), 7.61 (d, 1H), 7.55-7.53 (dd, 1H), 7.49-7.42 (m, 7H), 7.38 -7.29 (m, 5H), 7.02-6.97 (m, 1H)

Synthesis Example 45: Synthesis of Compound 73

4.97 g of Compound 73 (yield 65%) was prepared in the same manner as in the preparation of Compound 58 of Synthesis Example 34 except for using Intermediate 4-43 instead of Intermediate 4-25. Compound 73 was verified using MS/FAB and ¹ H NMR.

C ₅₈ H ₄₀ N ₂ : calc.764.32, and found; 764.33

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 7.85-7.82 (m, 2H), 7.81-7.79 (m, 2H), 7.78-7.75 (m, 2H), 7.73-7.68 (m, 4H), 7.67 -7.64 (m, 2H), 7.56-7.52 (m, 2H), 7.47-7.44 (m, 3H), 7.39-7.27 (m, 8H), 7.13-7.09 (m, 2H), 7.02-7.00 (m, 1H), 6.96-6.92 (m, 2H), 6.86-6.84 (dd, 1H), 6.82-6.79 (m, 2H), 6.77 (d, 1H), 1.65 (s, 6H)

Synthesis Example 46: Synthesis of Compound 76

In the same manner as the preparation of the compound 58 of Synthesis Example 34, 6.06 g of Compound 76 (yield: 78%) was prepared, except that Intermediate 4-76 was used instead of Intermediate 4-25. Compound 76 was verified using MS/FAB and ¹ H NMR.

C ₅₉ H ₄₀ N ₂ : calculated 776.32, and measured 776.32

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 8.68-8.67 (m, 1H), 8.39-8.36 (m, 1H), 7.94-7.91 (m, 1H), 7.84-7.80 (m, 3H), 7.79 -7.78 (m, 1H), 7.73-7.69 (m, 4H), 7.67-7.61 (m, 4H), 7.55-7.38 (m, 10H), 7.37-7.24 (m, 7H), 7.18-7.16 (m, 1H), 7.06-7.02 (m, 2H), 6.91-6.88 (m, 2H), 6.82-6.78 (m, 2H)

Synthesis Example 47: Synthesis of Compound 77

5.22 g of Compound 77 (yield 72%) was prepared in the same manner as in the preparation of Compound 58 of Synthesis Example 34, except that Intermediate 4-77 was used instead of Intermediate 4-25. Compound 77 was verified using MS/FAB and ¹ H NMR.

C ₅₄ H ₃₅ N ₃ : calculated value 725.28, and measured 725.27

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.55-8.52 (m, 2H), 7.85-7.82 (m, 2H), 7.81-7.77 (m, 3H), 7.74-7.70 (m, 4H), 7.67 (d, 1H), 7.65 (d, 1H), 7.58-7.52 (m, 5H), 7.47-7.44 (m, 3H), 7.39-7.28 (m, 7H), 7.11-7.09 (m, 1H), 7.02 -6.99 (m, 2H), 6.93 - 6.89 (m, 2H), 6.81-6.77 (m, 2H)

Synthesis Example 48: Synthesis of Compound 78

5.63 g of Compound 78 (yield 75%) was prepared in the same manner as in the preparation of Compound 58 of Synthesis Example 34, except that Intermediate 4-78 was used instead of Intermediate 4-25. Compound 78 was verified using MS/FAB and ¹ H NMR.

C ₅₇ H ₃₈ N ₂ : calculated value 750.30, while measured 750.29

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.67-8.65 (dd, 1H), 8.40-8.37 (m, 1H), 7.95-7.92 (m, 1H), 7.85-7.82 (m, 2H), 7.81 -7.79 (m, 2H), 7.78-7.76 (m, 2H), 7.74-7.68 (m, 4H), 7.66-7.63 (m, 3H), 7.58-7.52 (m, 4H), 7.48-7.44 (m, 4H), 7.37-7.25 (m, 8H), 7.16-7.15 (m, 1H), 7.02-7.00 (dd, 1H), 6.95-6.91 (m, 2H), 6.84-6.81 (m, 2H)

Synthesis Example 49: Synthesis of Compound 79

In the same manner as the preparation of Compound 58 of Synthesis Example 34, 5.00 g of Compound 79 (yield 69%) was obtained, except that Intermediate 4-79 was used instead of Intermediate 4-25. Compound 79 was verified using MS/FAB and ¹ H NMR.

C ₅₄ H ₃₅ N ₃ : calculated value 725.28, and measured 725.27

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.49-8.46 (m, 1H), 7.84-7.77 (m, 7H), 7.74-7.68 (m, 5H), 7.67-7.63 (m, 3H), 7.56 -7.54 (dd, 1H), 7.47-7.43 (m, 3H), 7.39-7.26 (m, 8H), 7.19-7.17 (m, 1H), 7.03-6.99 (m, 2H), 6.92-6.88 (m, 2H), 6.81-6.78 (m, 2H)

Synthesis Example 50: Synthesis of Compound 82 Synthesis of Intermediate 3-82

The intermediate 3-82 was prepared in the same manner as the preparation of the intermediate 3-1 of Synthesis Example 1, except that the intermediate 2-82 was used instead of the intermediate 2-1.

Synthesis of Compound 82

5.20 g of the compound was prepared in the same manner as in the preparation of the compound 1 of Synthesis Example 1, except that the intermediate 3-82 and the intermediate 4-25 were used instead of the intermediate 3-1 and the intermediate 4-1. 82 (yield 67%). Compound 82 was verified using MS/FAB and ¹ H NMR.

C ₅₉ H ₄₀ N ₂ : calculated value 776.32, and measured 776.33

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.68 (d, 1H), 8.41-8.38 (m, 1H), 7.94-7.91 (m, 1H), 7.86-7.80 (m, 5H), 7.74-7.64 (m, 10H), 7.56-7.53 (m, 1H), 7.49-7.44 (m, 4H), 7.38-7.24 (m, 7H), 7.13-7.09 (m, 2H), 7.04-6.99 (m, 3H) , 6.96-6.92 (m, 2H), 6.87-6.83 (m, 1H), 6.81-6.78 (m, 2H)

Synthesis Example 51: Synthesis of Compound 83

5.58 g of Compound 83 (yield 68%) was prepared in the same manner as in the preparation of Compound 82 of Synthesis Example 50, except that Intermediate 4-48 was used instead of Intermediate 4-25. Compound 83 was verified using MS/FAB and ¹ H NMR.

C ₆₃ H ₄₂ N ₂ : calcd. 826.33, and found 826.32 ¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.46-8.43 (m, 1H), 8.17-8.14 (m, 1H), 7.87-7.80 (m) , 6H), 7.79-7.75 (m, 2H), 7.74-7.63 (m, 12H), 7.56-7.54 (dd, 1H), 7.49-7.40 (m, 6H), 7.38-7.22 (m, 7H), 7.16 -7.14(m,1H), 7.05-7.00(m,2H), 6.95-6.93(dd,1H), 6.85-6.82(m,2H)

Synthesis Example 52: Synthesis of Compound 84 Synthesis of Intermediate 3-84

The intermediate 3-84 was prepared in the same manner as in the preparation of the intermediate 3-1 of Synthesis Example 1, except that the intermediate 2-84 was used instead of the intermediate 2-1.

Synthesis of Compound 84

4.90 g of the compound was prepared in the same manner as in the preparation of the compound 1 of Synthesis Example 1, except that the intermediate 3-84 and the intermediate 4-30 were used instead of the intermediate 3-1 and the intermediate 4-1. 84 (yield 62%). Compound 84 was verified using MS/FAB and ¹ H NMR.

C ₆₀ H ₄₂ N ₂ : calculated value 790.33, and measured 790.32

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.69 (d, 1H), 8.40-8.37 (m, 1H), 8.11 - 8.08 (m, 1H), 7.93 - 7.90 (m, 2H), 7.89 - 7.85 (m, 2H), 7.84 - 7.79 (m, 4H), 7.72 - 7.68 (m, 2H), 7.62 - 7.59 (m, 2H), 7.53 - 7.51 (m, 1H), 7.49 - 7.42 (m, 6H) , 7.40-7.25 (m, 8H), 7.13-7.11 (m, 1H), 7.07-7.05 (dd, 1H), 6.98-6.96 (dd, 1H), 6.90-6.86 (m, 2H), 6.82 (d, 1H), 1.62 (s, 6H)

Synthesis Example 53: Synthesis of Compound 85

4.90 g of Compound 84 (yield 64%) was prepared in the same manner as in the preparation of Compound 84 of Synthesis Example 52 except for using Intermediate 4-27 instead of Intermediate 4-30. Compound 84 was verified using MS/FAB and ¹ H NMR.

C ₅₇ H ₃₉ N ₃ : calculated value 765.31, and measured 765.30

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.68 (d, 1H), 8.38-8.35 (m, 1H), 7.95-7.92 (m, 2H), 7.90-7.88 (m, 1H), 7.85-7. (m, 4H), 7.73-7.69 (m, 2H), 7.63-7.60 (m, 2H), 7.55-7.52 (m, 2H), 7.48-7.44 (m, 2H), 7.41-7.33 (m, 5H) , 7.32-7.25 (m, 4H), 7.12-7.09 (m, 1H), 7.03-6.96 (m, 2H), 6.93-6.90 (dd, 1H), 6.88-6.84 (m, 2H), 6.80 (d, 1H), 1.61 (s, 6H)

Synthesis Example 54: Synthesis of Compound 86

4.73 g of Compound 86 (yield 64%) was prepared in the same manner as in the preparation of Compound 84 of Synthesis Example 52 except for using Intermediate 4-31 instead of Intermediate 4-30. Compound 86 was verified using MS/FAB and ¹ H NMR.

C ₅₆ H ₃₈ N ₂ : calculated value 738.30, and measured 738.31

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.11 - 8.08 (m, 1H), 7.94 - 7.91 (m, 1H), 7.89 - 7.85 (m, 2H), 7.84 - 7.79 (m, 4H), 7.72 - 7.69 (m, 2H), 7.62 - 7.59 (m, 2H), 7.54 - 7.51 (m, 1H), 7.49 - 7.41 (m, 5H), 7.40 - 7.34 (m, 5H), 7.32 - 7.25 (m, 3H), 7.14-7.12 (m, 1H), 7.01-6.99 (m, 1H), 6.93-6.87 (m, 3H), 6.85 (d, 1H), 1.62 (s, 6H)

Synthesis Example 55: Synthesis of Compound 89 Synthesis of Intermediate 3-89

The intermediate 3-89 was prepared in the same manner as in the preparation of the intermediate 3-1 of Synthesis Example 1, except that the intermediate 2-89 was used instead of the intermediate 2-1.

Synthesis of Compound 89

5.61 g of the compound was prepared in the same manner as in the preparation of the compound 1 of Synthesis Example 1, except that the intermediate 3-89 and the intermediate 4-4 were used instead of the intermediate 3-1 and the intermediate 4-1. 89 (yield 75%). Compound 89 was verified using MS/FAB and ¹ H NMR.

C ₅₇ H ₃₆ N ₂ : calculated value 748.29, and measured 748.30

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.25-8.19 (m, 2H), 8.11-8.09 (m, 1H), 8.06-8.04 (m, 1H), 7.85-7.82 (m, 2H), 7.81 - 7.80 (m, 1H), 7.78-7.77 (m, 1H), 7.72-7.68 (m, 3H), 7.64-7.61 (m, 2H), 7.59-7.55 (m, 3H), 7.54-7.48 (m, 3H), 7.47-7.43 (m, 3H), 7.42-7.35 (m, 5H), 7.34-7.27 (m, 3H), 7.12-7.08 (m, 2H), 7.02-6.98 (m, 2H), 6.90- 6.86 (m, 2H)

Synthesis Example 56: Synthesis of Compound 92 Synthesis of Intermediate 3-92

The intermediate 3-92 was prepared in the same manner as the preparation of the intermediate 3-1 of Synthesis Example 1, except that the intermediate 2-92 was used instead of the intermediate 2-1.

Synthesis of Compound 92

4.61 g of the compound was prepared in the same manner as in the preparation of the compound 1 of Synthesis Example 1, except that the intermediate 3-92 and the intermediate 4-27 were used instead of the intermediate 3-1 and the intermediate 4-1. 92 (yield 61%). Compound 92 was verified using MS/FAB and ¹ H NMR.

C ₅₄ H ₃₃ N ₃ S: calculated value 755.24, and measured 755.25

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 8.70-8.68 (m, 1H), 8.40-8.37 (m, 2H), 8.01 (d, 1H), 7.93-7.91 (m, 1H), 7.88-7.86 (dd, 1H), 7.85-7.82 (m, 2H), 7.81-7.80 (m, 1H), 7.78-7.76 (m, 1H), 7.73-7.69 (m, 2H), 7.64 (d, 1H) 7.63 7.62 (m, 1H), 7.54 - 7.51 (m, 1H), 7.48 - 7.43 (m, 2H), 7.40 - 7.35 (m, 4H), 7.34 - 7.24 (m, 5H), 7.13 - 7.12 (m, 1H) ), 7.06-7.03 (dd, 1H), 6.98-6.93 (m, 1H), 6.92-6.84 (m, 4H)

Synthesis Example 57: Synthesis of Compound 95 Synthesis of Intermediate 3-95

The intermediate 3-95 was prepared in the same manner as in the preparation of the intermediate 3-1 of Synthesis Example 1, except that the intermediate 2-95 was used instead of the intermediate 2-1.

Synthesis of Compound 95

4.74 g of the compound was prepared in the same manner as in the preparation of the compound 1 of Synthesis Example 1, except that the intermediate 3-95 and the intermediate 4-30 were used instead of the intermediate 3-1 and the intermediate 4-1. 95 (yield 62%). Compound 95 was verified using MS/FAB and ¹ H NMR.

C ₅₇ H ₃₆ N ₂ O: calculated 764.28, and measured 764.29

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.69-8.67 (m, 1H), 8.41-8.38 (m, 1H), 8.11-8.08 (m, 1H), 8.04-8.02 (m, 1H), 7.99 -7.96(m,2H),7.94-7.91(m,1H),7.87-7.85(m,1H),7.84-7.77(m,6H),7.73-7.69(m,2H),7.55-7.52(m, 1H), 7.48-7.41 (m, 5H), 7.40-7.36 (m, 3H), 7.35-7.25 (m, 5H), 7.10-7.04 (m, 2H), 6.98-6.96 (m, 1H), 6.94 6.92 (dd, 1H), 6.88-6.85 (m, 2H)

Synthesis Example 58: Synthesis of Compound 97 Synthesis of Intermediate 3-97

In addition to using the intermediate 2-97 instead of the intermediate 2-1, The preparation of the intermediate 3-1 of Example 1 was prepared in the same manner as the intermediate 3-97.

Synthesis of Compound 97

4.96 g of the compound was prepared in the same manner as in the preparation of the compound 1 of Synthesis Example 1, except that the intermediate 3-97 and the intermediate 4-4 were used instead of the intermediate 3-1 and the intermediate 4-1. 97 (yield 61%). Compound 97 was verified using MS/FAB and ¹ H NMR.

C ₆₁ H ₃₉ N ₃ : calculated value 811.31, and measured 813.32

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.31-8.29 (m, 1H), 7.84-7.82 (m, 2H), 7.81-7.80 (m, 1H), 7.77-7.74 (m, 1H), 7.72 -7.68 (m, 4H), 7.64-7.61 (m, 2H), 7.60-7.58 (m, 1H), 7.54-7.47 (m, 7H), 7.46-7.41 (m, 4H), 7.40-7.36 (m, 5H), 7.34-7.28 (m, 4H), 7.24-7.22 (m, 1H), 7.16-7.14 (m, 1H), 7.06-7.00 (m, 2H), 6.86-6.80 (m, 3H)

Synthesis Example 59: Synthesis of Compound 98

4.65 g of Compound 98 (yield 59%) was prepared in the same manner as in the preparation of Compound 97 of Synthesis Example 58 except that Intermediate 4-31 was used instead of Intermediate 4-4. Compound 98 was verified using MS/FAB and ¹ H NMR.

C ₅₉ H ₃₇ N ₃ : Calculated value 787.30, and measured 787.29

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.32-8.30 (m, 1H), 8.10-8.07 (dd, 1H), 7.87-7.85 (m, 1H), 7.84-7.80 (m, 2H), 7.80 -7.79 (m, 1H), 7.76-7.74 (m, 1H), 7.73-7.68 (m, 4H), 7.61-7.58 (m, 1H), 7.55-7.51 (m, 1H), 7.50-7.43 (m, 7H), 7.42-7.35 (m, 6H), 7.34-7.23 (m, 6H), 7.13-7.10 (m, 1H), 7.04-7.03 (dd, 1H), 6.94-6.91 (dd, 1H), 6.87- 6.84 (m, 2H)

Synthesis Example 60: Synthesis of Compound 99 Synthesis of Intermediate 3-99

The intermediate 3-99 was prepared in the same manner as the preparation of the intermediate 3-1 of Synthesis Example 1, except that the intermediate 2-98 was used instead of the intermediate 2-1.

Synthesis of Compound 99

Preparing 5.03 g of compound in the same manner as in the preparation of Compound 1 of Synthesis Example 1, except that Intermediate 3-99 and Intermediate 4-30 were used instead of Intermediate 3-1 and Intermediate 4-1. 99 (yield 55%). Compound 99 was verified using MS/FAB and ¹ H NMR.

C ₆₉ H ₄₅ N ₃ : calculated value 915.36, and measured 915.35

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 8.90 (s, 1H), 8.60-8.58 (dd, 1H), 8.45 (s, 1H), 8.13 - 8.11 (dd, 1H), 7.94 - 7.91 (m) , 1H), 7.87-7.75 (m, 5H), 7.72-7.58 (m, 7H), 7.54-7.21 (m, 23), 7.16-7.14 (m, 1H), 7.03-6.99 (m, 2H), 6.89 -6.84(m,2H)

Synthesis Example 61: Synthesis of Compound 103

In the same manner as the preparation of Compound 1 of Synthesis Example 1, except that the intermediate B37 was used instead of the intermediate 4-1, 5.71 g of Compound 103 (yield 76%) was prepared. Compound 103 was verified using MS/FAB and ¹ H NMR.

C ₅₆ H ₃₇ N ₃ : calculated value 751.30, measured 751.28

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 8.76 (s, 2H), 8.57 (d, 2H), 8.12 (d, 1H), 7.93 (d, 2H), 7.87-7.65 (m, 9H), 7.61-7.27 (m, 15H), 7.14-7.10 (m, 2H), 7.08-7.05 (m, 3H), 6.98 (d, 1H)

Synthesis Example 62: Synthesis of Compound 104

In the same manner as the preparation of Compound 1 of Synthesis Example 1, except that the intermediate B38 was used instead of the intermediate 4-1, 5.23 g of Compound 104 (yield: 72%) was prepared. Compound 104 was verified using MS/FAB and ¹ H NMR.

C ₅₃ H ₃₄ N ₄ : calculated value 726.28, measured 726.27

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 8.78 (s, 2H), 8.56 (d, 2H), 7.94 (d, 2H), 7.84-7.80 (m, 3H), 7.72-7.60 (m, 7H ), 7.54 - 7.25 (m, 11H), 7.12 - 7.08 (m, 5H), 7.02 - 6.99 (m, 2H)

Synthesis Example 63: Synthesis of Compound 107

6.21 g of the compound 107 were prepared in the same manner as in the preparation of the compound 1 of Synthesis Example 1, except that the intermediate 3-58 and the intermediate B37 were used instead of the intermediate 3-1 and the intermediate 4-1. Yield 75%). Compound 107 was verified using MS/FAB and ¹ H NMR.

C ₆₂ H ₄₁ N ₃ : calculated value 827.33, measured 827.31

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 8.76 (s, 2H), 8.57 (d, 2H), 8.11 (d, 1H), 7.94 (d, 2H), 7.87-7.62 (m, 13H), 7.54-7.26(m,15H), 7.12-7.10(m,3H),7.06-7.03(m,1H),6.96-6.92(m,2H)

Intermediate

Example 1

To make the anode, the Corning 15 Ω/cm ² (1200 Å) ITO glass substrate was cut to a size of 50 mm x 50 mm x 0.7 mm, followed by each ultrasonic wave in isopropanol and pure water for 5 minutes, and irradiated with ultraviolet light 30. Minutes and exposed to ozone. The resulting glass substrate was placed in a vacuum deposition diode.

2-TNATA was deposited on an ITO glass substrate to form a hole injection layer having a thickness of 600 Å on the anode, followed by deposition of 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl ( 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPS) was formed on the hole injection layer to form a hole transport layer having a thickness of 300 Å.

Next, 9,10-di(naphthalen-2-yl)anthracene (9,10-di-naphthalene-2-yl-anthracene (ADN)) and 4,4'-bis[2-(4-(N,N-diphenylamino)-phenyl)vinyl]biphenyl ( 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl(DPAVBi)) is co-deposited on the hole transport layer in a weight ratio of 98:2 to form a thickness of about 300 Å. Light-emitting layer.

Next, the compound 1 is deposited on the light-emitting layer to form about 300 Å. A thickness of the electron transport layer is then deposited on the electron transport layer to form an electron injecting layer having a thickness of about 10 Å. Next, Al is deposited on the electron injecting layer to form a second electrode (cathode) having a thickness of about 3,000 Å, thereby completing the fabrication of the organic light emitting diode.

<DPAVBi>

Example 2

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the compound 4 was used instead of the compound 1 to form an electron transport layer.

Example 3

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the compound 14 was used instead of the compound 1 to form an electron transport layer.

Example 4

In addition to using compound 23 instead of compound 1, an electron transport layer is formed Further, an organic light-emitting diode manufactured in the same manner as in Example 1.

Example 5

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the compound 25 was used instead of the compound 1 to form an electron transport layer.

Example 6

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the compound 27 was used instead of the compound 1 to form an electron transport layer.

Example 7

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the compound 31 was used instead of the compound 1 to form an electron transport layer.

Example 8

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the compound 32 was used instead of the compound 1 to form an electron transport layer.

Example 9

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the compound 42 was used instead of the compound 1 to form an electron transport layer.

Example 10

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the compound 48 was used instead of the compound 1 to form an electron transport layer.

Example 11

In addition to using compound 58 instead of compound 1, an electron transport layer is formed Further, an organic light-emitting diode manufactured in the same manner as in Example 1.

Example 12

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the compound 60 was used instead of the compound 1 to form an electron transport layer.

Example 13

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the compound 62 was used instead of the compound 1 to form an electron transport layer.

Example 14

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the compound 66 was used instead of the compound 1 to form an electron transport layer.

Example 15

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the compound 70 was used instead of the compound 1 to form an electron transport layer.

Example 16

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the electron transport layer was formed using Compound 77 instead of Compound 1.

Example 17

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the compound 82 was used instead of the compound 1 to form an electron transport layer.

Example 18

In addition to using compound 86 instead of compound 1, an electron transport layer is formed Further, an organic light-emitting diode manufactured in the same manner as in Example 1.

Example 19

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the electron transporting layer was formed using Compound 97 instead of Compound 1.

Example 20

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the light-emitting layer was formed using Compound 25 instead of DPAVBi, and Alq _{3 was used} instead of Compound 1.

Example 21

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the light-emitting layer was formed using Compound 86 instead of DPAVBi, and Alq _{3 was} formed instead of Compound 1.

Example 22

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the compound 103 was used instead of the compound 1 to form an electron transport layer.

Example 23

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the compound 104 was used instead of the compound 1 to form an electron transport layer.

Example 24

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the compound 107 was used instead of the compound 1 to form an electron transport layer.

Comparative example 1

An organic light-emitting diode manufactured in the same manner as in Example 1 except that an electron transport layer was formed using Alq ₃ instead of Compound 1.

Comparative example 2

Compound A was synthesized according to the following Reaction Scheme A:

Synthesis of Intermediate 3-A

The intermediate 3-A was prepared in the same manner as the preparation of the intermediate 3-1 of Synthesis Example 1, except that the intermediate 1-A was used instead of the intermediate 1-1.

Synthesis of Compound A

In addition to the use of 4.24 g (10 mmol) of intermediate 3-A and 2.23 g (12.0 mmol) of intermediate 4-A instead of intermediate 3-1 and intermediate 4-1, with compound 1 of Synthesis Example 1. In the same manner as in the preparation, 3.23 g of Compound A (yield 63%) was prepared.

Manufacture of organic light-emitting diodes

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the compound A was used instead of the compound 1 to form an electron transport layer.

Comparative example 3

Compound B was synthesized according to the following Reaction Scheme B:

Synthesis of Compound B

Compound B was prepared in the same manner as in the preparation of Compound A of Comparative Example 2 except that Intermediate 4-B was used instead of Intermediate 4-A.

Manufacture of organic light-emitting diodes

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the compound B was used instead of the compound 1 to form an electron transport layer.

Comparative example 4

Compound C was synthesized according to the following reaction scheme C:

Synthesis of Compound C

Compound C was prepared in the same manner as in the preparation of Compound A of Comparative Example 2 except that Intermediate 4-C was used instead of Intermediate 4-A.

Manufacture of organic light-emitting diodes

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the compound C was used instead of the compound 1 to form an electron transport layer.

Comparative Example 5

Compound D was synthesized according to the following reaction scheme D:

Synthesis of Compound D

Compound D was prepared in the same manner as in the preparation of Compound A of Comparative Example 2 except that Intermediate 4-D was used instead of Intermediate 4-A.

Manufacture of organic light-emitting diodes

An organic light-emitting diode manufactured in the same manner as in Example 1 except that the compound D was used instead of the compound 1 to form an electron transport layer.

Evaluation Example 1

Driving voltage, brightness, luminescent color, and efficiency of the organic light-emitting diodes of Examples 1 to 24 and Comparative Examples 1 to 5 using PR650 (Spectroscan) light source measuring unit (from Photo Research, Inc.) (@50 mA/ Current density of cm ² ) and service life (@100 mA/cm ² ). The results are presented in Table 1 below.

Referring to Table 1, it was found that compared with the organic matter of Comparative Example 1 to Comparative Example 5 The light-emitting diodes, the organic light-emitting diodes of Examples 1 to 19 and Examples 22 to 24 have a lower driving voltage, higher brightness, higher efficiency, and better Service life characteristics. The organic light-emitting diodes of Examples 20 to 21 were found to have a lower driving voltage and a better service life than the organic light-emitting diode of Comparative Example 1.

As described above, the organic light-emitting diode including any amine compound according to the embodiment can have a low driving voltage, high luminance, high efficiency, and long service life.

While the present invention has been particularly shown and described with reference to the exemplary embodiments thereof, it will be understood by those skilled in the art The scope and spirit of this embodiment.

10‧‧‧Organic Luminescent Diodes

11‧‧‧Substrate

13‧‧‧First electrode

15‧‧‧Organic layer

17‧‧‧second electrode

Claims (39)

An amine compound represented by the following Chemical Formula 1: Wherein in Chemical Formula 1, Ar ₁ and Ar _{2 are} each independently a substituted or unsubstituted C ₆ -C ₆₀ aryl group or a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group; X ₁ is a Substituted or unsubstituted C ₆ -C ₆₀ extended aryl or substituted or unsubstituted C ₂ -C ₆₀ heteroaryl; m is an integer from 1 to 5; and each substituted C ₆ -C ₆₀ The aryl group, the substituted C ₂ -C ₆₀ heteroaryl group, the substituted C ₆ -C ₆₀ extended aryl group and the substituted C ₂ -C ₆₀ heteroaryl group are at least one substituent; ;-Cl; -Br; -I; -CN; hydroxy; -NO ₂ ; amino group; formazan; hydrazine; hydrazine; carboxyl group or its salt; sulfonic acid group or its salt; phosphate group or its salt; _6- C ₆₀ aryl)decylalkyl; C ₁ -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl; fluorene atom, -F, Substituting at least one of -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, methionyl, anthracene, fluorene, carboxy or a salt thereof, a sulfonic acid group or a salt thereof or a phosphate group or a salt thereof C ₁ -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy, C ₂ -C ₆₀ alkenyl, and C ₂ -C ₆₀ alkynyl; C ₃ -C ₆₀ cycloalkyl, C ₃ -C ₆₀ ring Alkenyl, C ₆ -C ₆₀ aryl, C ₂ -C ₆₀ heteroaryl, C ₆ -C ₆₀ aralkyl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio; fluorene atom, -F, -Cl, -Br, - I, -CN, hydroxy, -NO ₂ , amino, methionyl, hydrazine, hydrazine, carboxyl or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₆₀ alkyl group, at least one Fluorine (F) substituted C ₁ -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₆ -C ₆₀ aryl and C ₂ - of at least one substituted heteroaryl C C ₆₀ aryl group ₃ -C ₆₀ cycloalkyl, C ₃ -C ₆₀ cycloalkenyl, C ₆ -C ₆₀ aryl, C ₂ -C ₆₀ heteroaryl, C ₆ -C _{One of 60} aralkyl, C ₆ -C ₆₀ aryloxy and C ₆ -C ₆₀ arylthio, wherein at least one of Ar ₁ and Ar ₂ is selected from -F; -CN; -NO ₂ a C ₁ -C ₆₀ alkyl group substituted with at least one -F; a C ₂ -C ₆₀ heteroaryl group; and a ruthenium atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, formamidine, hydrazine, hydrazine, carboxyl or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkane substituted with at least one -F , C ₁ -C ₆₀ alkoxy, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₆ -C ₆₀ aromatic Group and C ₂ -C ₆₀ heteroaryl groups substituted with at least one of C ₂ -C ₆₀ heteroaryl group consisting of at least one electron withdrawing substituent of C ₆ -C ₆₀ aryl group. The amine-based compound according to claim 1, wherein at least one of the electron-donating groups is selected from the group consisting of: -F; -CN; -NO ₂ ; C ₁ -C ₂₀ alkyl substituted by at least one -F; Forming a C ₂ -C ₂₀ heteroaryl group of a N atom; and comprising a ring to form a N atom and passing through a halogen atom, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, methyl group , hydrazine, hydrazine, carboxyl or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one -F, a C ₁ -C ₂₀ group consisting of alkoxy, C ₆ -C ₂₀ aryl and C ₂ -C ₂₀ heteroaryl groups substituted with at least one of C ₂ -C ₂₀ heteroaryl group. The amine-based compound according to claim 1, wherein at least one of the electron-donating groups is selected from the group consisting of -F; -CN; C ₁ -C ₂₀ alkyl substituted by at least one -F; pyrrolyl, pyrazolyl, Imidazolyl, imidazolinyl, imidazolidinyl, imidazopyridyl, pyridyl, pyrazinyl, pyrimidinyl, benzimidazolyl, indolyl, fluorenyl, quinolyl, isoquinolinyl, pyridazinyl, Pyridazinyl, quinazolinyl, porphyrinyl, oxazolyl, oxazolyl, phenazinyl, phenanthryl, triazinyl, pyridazinyl, triazolyl and tetrazolyl; , -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, formamidine, hydrazine, hydrazine, carboxyl or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, C ₁ -C ₂₀ alkyl, -F substituted with at least one of C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, anthryl, phenanthryl, pyrenyl group, a pyridyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, an imidazolinyl group, an imidazolidinyl group, an imidazolidinyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a benzimidazolyl group substituted with at least one of a triazinyl group and an oxazolyl group;吲哚基,嘌呤基, Lolinyl, isoquinolyl, pyridazinyl, pyridazinyl, quinazolinyl, porphyrinyl, oxazolyl, oxazolyl, phenazinyl, phenanthryl, triazinyl, pyridazinyl, A group consisting of triazolyl and tetrazolyl. The amine compound according to claim 1, wherein Ar ₁ and Ar _{2 are} each independently substituted or unsubstituted phenyl, substituted or unsubstituted cyclopentadienyl, substituted Or unsubstituted fluorenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted cycloheptatrienyl, substituted or unsubstituted Cyclopentadienylphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted propylene naphthyl, substituted or unsubstituted phenanthryl, Substituted or unsubstituted fluorenyl, substituted or unsubstituted allyldienyl, substituted or unsubstituted tert-triphenyl, substituted or unsubstituted fluorenyl, substituted or not Substituted thiol, substituted or unsubstituted fused tetraphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pentaphenyl, Substituted or unsubstituted hexaphenyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyridyl Substituted, substituted or unsubstituted imidazolyl, substituted or unsubstituted imidazolinyl, substituted or unsubstituted imidazolidinyl, substituted or unsubstituted imidazolidine, substituted or unsubstituted Substituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted fluorenyl, Substituted or unsubstituted fluorenyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted Naphthyridinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted porphyrin, substituted or unsubstituted carbazolyl, substituted or unsubstituted carbazolyl, Substituted or unsubstituted phenazinyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyranyl, substituted or unsubstituted alkenyl, substituted or unsubstituted Furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted a thienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted isoxazole group a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted oxadiazolyl group, Substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazolyl, substituted or unsubstituted tetrazolyl or substituted or unsubstituted morpholinyl, wherein Ar ₁ and Ar ₂ At least one of them is a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, an anthracenyl group or an anthracenyl group substituted with at least one electron-donating group. The amine-based compound according to claim 1, wherein Ar ₁ and Ar _{2 are} each independently substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted Mercapto, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted tert-triphenyl, substituted or unsubstituted fluorenyl, substituted or not Substituted indenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted Or unsubstituted carbazolyl, substituted or unsubstituted triazinyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl or substituted or not a substituted morpholinyl group, wherein at least one of Ar ₁ and Ar ₂ is a C ₁ -C ₂₀ alkyl group selected from -F; -CN; substituted with at least one -F; pyridyl, pyrazinyl, pyrimidine Group, quinolyl, isoquinolyl, quinazolinyl, triazinyl, benzimidazolyl and oxazolyl; and ruthenium atom, -F -Cl, -Br, -I, -CN, hydroxy, -NO _2, amino, carbamimidoyl, corpus, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C _{a 20} alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one -F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, a fluorenyl group, a pyridyl group, a triazinyl group and a group consisting of at least one of a carbazolyl group substituted with a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a triazinyl group, a benzimidazolyl group, and a carbazolyl group At least one electron-substituted phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, anthracenyl or fluorenyl group. The amine compound according to claim 1, wherein at least one of Ar ₁ and Ar _{2 is} a C ₆ -C ₆₀ aryl group substituted with at least two electron withdrawing groups. The amine compound according to claim 1, wherein at least one of Ar ₁ and Ar _{2 is} a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group substituted with at least two electron withdrawing groups. a mercapto or fluorenyl group; and the electron withdrawing groups are each independently selected from the group consisting of pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl and carbazole And a ruthenium atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, formamyl, oxime, oxime, carboxyl or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one -F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, Pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, pyridazinyl, benzimidazole substituted with at least one of a mercapto group, a pyridyl group, a triazinyl group and an oxazolyl group a group consisting of a base and a carbazolyl group. The amine compound according to claim 1, wherein the amine compound is represented by the following Chemical Formula 1 (1) or Chemical Formula 1 (2): Wherein in the chemical formula 1 (1), Ar ₂ is a substituted or unsubstituted C ₆ -C ₂₀ aryl group or a substituted or unsubstituted C ₂ -C ₂₀ heteroaryl group; and in the chemical formula 1 (1) And in the chemical formula 1 (2), the A ring and the B ring are each independently a substituted C ₆ -C ₂₀ aryl group; R ₁ and R _{2 are} each independently selected from the group consisting of: -F; -CN; -NO ₂ ; a C ₁ -C ₆₀ alkyl group substituted with at least one -F; a C ₂ -C ₆₀ heteroaryl group; and a ruthenium atom, -F, -Cl, -Br, -I, -CN, a hydroxyl group, -NO ₂ , Amino, formamidine, anthracene, anthracene, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkyl group substituted with at least one -F a C ₁ -C ₆₀ alkoxy group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₆ -C ₆₀ aryl group, and a C ₂ -C ₆₀ heteroaryl group substituted with at least one C ₂ a -C ₆₀ heteroaryl group of electron withdrawing groups; and p and q are each independently an integer from 1 to 9. The amine-based compound according to claim 8, wherein the amine-based compound is represented by the chemical formula 1 (1), and at least one of the p-numbers of R ₁ is -CN; or represented by the chemical formula 1 (2) One of the p number of R ₁ and one of the q number of R ₂ is -CN. The amine compound according to claim 8, wherein the amine compound is represented by Chemical Formula 1 (2), and at least one of p number of R ₁ and q number of R ₂ is -CN. The amine-based compound according to claim 8, wherein the amine compound is represented by the chemical formula 1 (1), and the ring A is a substituted phenyl group, a substituted biphenyl group, a substituted naphthyl group, a substituted fluorenyl group, a substituted phenanthryl group, a substituted fluorenyl group or a substituted fluorenyl group; or wherein the amine compound is represented by the chemical formula 1 (2), and the A ring and the B ring are each independently substituted A phenyl group, a substituted biphenyl group, a substituted naphthyl group, a substituted indenyl group, a substituted phenanthryl group, a substituted indenyl group or a substituted indenyl group. The amine-based compound according to claim 8, wherein the amine compound is represented by the chemical formula 1 (1), wherein the ring A is a substituted phenyl group, a substituted biphenyl group, a substituted naphthyl group, Substituted fluorenyl, substituted phenanthryl, substituted fluorenyl or substituted fluorenyl; R ₁ is selected from pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazoline a porphyrin group, a triazinyl group, a benzimidazolyl group and a carbazolyl group; and a ruthenium atom, -F, -Cl, -Br, -I, -CN, a hydroxyl group, -NO ₂ , an amino group, a decyl group, an anthracene group, Anthracene, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one -F, a C ₁ -C ₂₀ alkoxy group Pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinoline substituted with at least one of phenyl, naphthyl, anthracenyl, phenanthryl, anthryl, pyridyl, triazinyl and oxazolyl At least one electron group of the group consisting of a quinazolinyl group, a pyrazinyl group, a benzimidazolyl group, and a carbazolyl group; and p is 2, 3 or 4. The amine-based compound according to claim 8, wherein the amine compound is represented by the chemical formula 1 (2), wherein the A ring and the B ring are each independently a substituted phenyl group, a substituted biphenyl group, Substituted naphthyl, substituted fluorenyl, substituted phenanthryl, substituted fluorenyl or substituted fluorenyl; R ₁ and R _{2 are} each independently selected from pyridinyl, pyrazinyl, pyrimidinyl , quinolyl, isoquinolyl, quinazolinyl, triazinyl, benzimidazolyl and oxazolyl; with ruthenium atoms, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, formamyl, hydrazine, hydrazine, carboxyl or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ - substituted with at least one -F Pyridyl, pyrazine substituted with at least one of C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, phenanthryl, anthryl, pyridyl, triazinyl and oxazolyl At least one electron group of the group consisting of pyridyl, pyrimidinyl, quinolyl, isoquinolyl, quinazolinyl, pyridazinyl, benzimidazolyl and oxazolyl; and p and q are each independently 2, 3 or 4. The amine-based compound according to claim 1, wherein at least one of the electron-donating groups in Chemical Formula 1 is selected from the group consisting of F; -CN; C ₁ -C ₂₀ alkyl substituted by at least one -F; pyridyl group, Pyrazinyl, pyrimidinyl, quinolyl, isoquinolyl, quinazolinyl, triazinyl, and benzimidazolyl; and ruthenium atom, -F, -Cl, -Br, -I, -CN , a hydroxyl group, a -NO ₂ , an amino group, a decyl group, an anthracene, an anthracene group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₂₀ alkyl group, substituted by at least one -F a pyridyl group substituted with at least one of C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, phenanthryl, anthracenyl, pyridyl, triazinyl and oxazolyl a group consisting of pyrazinyl, pyrimidinyl, quinolyl, isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl and oxazolyl. The amine compound according to claim 14, wherein at least one of Ar ₁ and Ar ₂ is a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, an anthracene group substituted with at least one electron withdrawing group. Base or thiol. The amine compound according to claim 1, wherein at least one of the electron withdrawing groups is selected from the group consisting of -F; -CN; -CH ₂ F; -CHF ₂ ; -CF ₃ ; and the following chemical formula 2 (1) To the group consisting of the groups represented by Chemical Formula 2 (14): Wherein in the chemical formula 2 (1) to the chemical formula 2 (14), each of Z ₁₁ to Z _{18 is} independently a hydrogen atom, a halogen atom, -F, -Cl, -Br, -I, -CN, a hydroxyl group, -NO ₂ , amino, formamidine, hydrazine, hydrazine, carboxyl or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkane substituted with at least one -F A C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a fluorenyl group, a pyridyl group, a triazinyl group or a carbazolyl group; wherein * represents a bonding position. The amine compound according to claim 16, wherein at least one of Ar ₁ and Ar ₂ is a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, an anthracene group substituted with at least one electron withdrawing group. Base or thiol. The amine compound according to claim 1, wherein Ar ₁ and Ar ₂ are bonded by a single bond. The amine compound according to claim 1, wherein the amine compound is represented by one of the following Chemical Formula 1A to Chemical Formula 1J: Wherein in Chemical Formula 1A to Chemical Formula 1J, Ar ₂ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted cyclopentadienyl group, a substituted or unsubstituted fluorenyl group, substituted or not Substituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted cycloheptatrienyl, substituted or unsubstituted dicyclopentadienylphenyl, substituted or not Substituted fluorenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted propylene naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted Or unsubstituted alkadienyl, substituted or unsubstituted tert-triphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted A thick tetraphenyl, substituted or unsubstituted fluorenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pentaphenyl group, a substituted or unsubstituted hexaphenyl group, Substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted Substituted, substituted or unsubstituted imidazolinyl, substituted or unsubstituted imidazolidinyl, substituted or unsubstituted imidazolidine, substituted or unsubstituted pyridyl, substituted or unsubstituted Substituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted fluorenyl, Substituted or unsubstituted quinolinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted a quinazolinyl group, a substituted or unsubstituted porphyrin group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenazinyl group, Substituted or unsubstituted phenanthryl, substituted or unsubstituted pyranyl, substituted or unsubstituted alkenyl, substituted or unsubstituted furyl, substituted or unsubstituted Benzofuranyl, substituted or unsubstituted thienyl, substituted or unsubstituted Benzothiophenyl, substituted or unsubstituted isothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted isoxazolyl, substituted or unsubstituted diphenyl And a thienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted pyridazinyl group , substituted or unsubstituted triazolyl, substituted or unsubstituted tetrazolyl or substituted or unsubstituted morpholinyl, substituted phenyl, substituted cyclopentadienyl, Substituted fluorenyl, substituted naphthyl, substituted fluorenyl, substituted cycloheptatrienyl, substituted dicyclopentadienylphenyl, substituted fluorenyl, substituted hydrazine Substituted, substituted propylene naphthyl, substituted phenanthryl, substituted fluorenyl, substituted alkadienyl fluorenyl, substituted triphenyl, substituted fluorenyl, substituted hydrazine Substituted, substituted fused tetraphenyl, substituted fluorenyl, substituted fluorenyl, substituted pentaphenyl, substituted thick Phenyl, substituted pyrrolyl, substituted pyrazolyl, substituted imidazolyl, substituted imidazolinyl, substituted imidazolidinyl, substituted imidazolidinyl, substituted pyridyl, Substituted pyrazinyl, substituted pyrimidinyl, substituted benzimidazolyl, substituted fluorenyl, substituted fluorenyl, substituted quinolyl, substituted pyridazinyl, substituted Pyridazinyl, substituted naphthyridinyl, substituted quinazolinyl, substituted porphyrin, substituted carbazolyl, substituted carbazolyl, substituted phenazinyl, substituted Fenridinyl, substituted pyranyl, substituted alkenyl, substituted furanyl, substituted benzofuranyl, substituted thienyl, substituted benzothienyl, substituted Isothiazolyl, substituted benzimidazolyl, substituted isoxazolyl, substituted dibenzothiophenyl, substituted dibenzofuranyl, substituted triazinyl, substituted dim Azolyl, substituted pyridazinyl, substituted triazolyl, substituted tetrazolyl and Substituent group instead phenanthroline group, and R ₁₁ to R ₁₉ are each independently a hydrogen atom; a deuterium atom; -F; -Cl; -Br; -I ; -CN; hydroxy; -NO _2; an amino group; formamidine Carboxy; hydrazine; hydrazine; a carboxyl group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphate group or a salt thereof; a tris(C ₆ -C ₆₀ aryl)decylalkyl group; a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ Alkoxy, C ₂ -C ₆₀ alkenyl and C ₂ -C ₆₀ alkynyl; via fluorene atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, formazan a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₂ -C ₆₀ substituted with at least one of hydrazine, hydrazine, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphate group or a salt thereof Alkenyl and C ₂ -C ₆₀ alkynyl; C ₃ -C ₆₀ cycloalkyl, C ₃ -C ₆₀ cycloalkenyl, C ₆ -C ₆₀ aryl, C ₂ -C ₆₀ heteroaryl, C ₆ -C _{a 60-} aralkyl group, a C ₆ -C ₆₀ aryloxy group, and a C ₆ -C ₆₀ arylthio group; and a ruthenium atom, -F, -Cl, -Br, -I, -CN, a hydroxyl group, -NO ₂ , Amino, formamidine, anthracene, anthracene, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkyl group substituted with at least one -F , C ₁ -C ₆₀ alkoxy, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkyne a C ₃ -C ₆₀ cycloalkyl group, a C ₃ -C ₆₀ cycloalkenyl group, a C ₆ -C ₆₀ aryl group substituted with at least one of a C ₆ -C ₆₀ aryl group and a C ₂ -C ₆₀ heteroaryl group, a C ₂ -C ₆₀ heteroaryl group, a C ₆ -C ₆₀ arylalkyl group, a C ₆ -C ₆₀ aryloxy group and a C ₆ -C ₆₀ arylthio group, wherein R ₁₁ to R ₁₅ in the chemical formula 1A and the chemical formula 1B At least one of, at least one of R ₁₁ to R ₁₇ in Chemical Formula 1C and Chemical Formula 1D, at least one of Chemical Formula 1E and R ₁₁ to R ₁₈ in Chemical Formula 1J, and Chemical Formula 1F, Chemical Formula 1G, Chemical Formula 1H, and Chemical Formula 1I At least one of R ₁₁ to R ₁₉ is independently selected from the group consisting of -F; -CN; -NO ₂ ; C ₁ -C ₆₀ alkyl substituted with at least one -F; C ₂ -C ₆₀ heteroaryl And a ruthenium atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, formamidine, oxime, oxime, carboxyl or a salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkyl group substituted with at least one -F, a C ₁ -C ₆₀ alkoxy group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ electron withdrawing groups of alkynyl groups, at least one C ₆ -C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group substituted with aryl of C ₂ -C ₆₀ heteroaryl of. An amine-based compound according to claim 19, wherein Ar ₁ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, substituted Or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted tert-triphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted thiol, Substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted anthracene An oxazolyl group, a substituted or unsubstituted triazinyl group or a substituted or unsubstituted morpholinyl group; and at least one of R ₁₁ to R ₁₅ in the chemical formula 1A and the chemical formula 1B, and the chemical formula 1C and the chemical formula 1D At least one of R ₁₁ to R ₁₇ , at least one of Chemical Formula 1E and at least one of R ₁₁ to R ₁₈ in Chemical Formula 1J, and at least one of Chemical Formula 1F to Chemical Formula 1I, each of R ₁₁ to R ₁₉ are each independently selected from -F; -CN; -NO ₂ ; C ₁ -C ₂₀ alkyl substituted by at least one -F; pyridyl, pyrazinyl, pyrimidine Pyridyl, quinolyl, isoquinolyl, quinazolinyl, triazinyl, benzimidazolyl and carbazolyl; through ruthenium atom, -F, -Cl, -Br, -I, -CN, hydroxy , -NO ₂ , amino, carbenyl, anthracene, anthracene, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ substituted with at least one -F -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, phenanthryl, anthracenyl, pyridyl, triazinyl and at least one substituted carbazole group, pyridyl An electron withdrawing group consisting of a group consisting of a pyridyl group, a pyrimidinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a pyridazinyl group, a triazinyl group, a benzimidazolyl group, and a carbazolyl group. The amine-based compound according to claim 19, wherein Ar ₂ is a C ₁ -C ₂₀ alkyl group selected from -F; -CN; -NO ₂ ; substituted by at least one -F; pyridyl, pyridyl Azinyl, pyrimidinyl, quinolyl, isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl and oxazolyl; and ruthenium atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, methionyl, anthracene, fluorene, carboxy or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₂₀ alkyl group, via at least one -F Substituting at least one of a substituted C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a fluorenyl group, a pyridyl group, a triazinyl group and an oxazolyl group At least one electron-donating group consisting of pyridyl, pyrazinyl, pyrimidinyl, quinolyl, isoquinolinyl, quinazolinyl, pyridazinyl, triazinyl, benzimidazolyl and oxazolyl groups Substituted phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, anthryl or fluorenyl. The amine-based compound according to claim 1, wherein the amine-based compound is represented by the following Chemical Formula 1A-(1) or Chemical Formula 1A-(2): Wherein in Chemical Formula 1A-(1) and Chemical Formula 1A-(2), R ₁₂ , R ₁₄ , R ₂₂ and R _{24 are} each independently selected from pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, iso-quine. a phenyl group, a quinazolinyl group, a triazinyl group, a benzimidazolyl group and a carbazolyl group; and a ruthenium atom, -F, -Cl, -Br, -I, -CN, hydroxy group, -NO ₂ , amino group, A Anthracenyl, anthracene, anthracene, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one -F, C ₁ Pyridyl, pyrazinyl, pyrimidinyl, quinoline substituted with at least one of -C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, phenanthryl, anthryl, pyridyl, triazinyl and oxazolyl a group of electron withdrawing groups consisting of a group consisting of a quinolyl group, an isoquinolyl group, a quinazolinyl group, a pyridazinyl group, a benzimidazolyl group, and a carbazolyl group; and Ar ₂ is a substituted or unsubstituted phenyl group, substituted or Unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, or Substituted or unsubstituted thiol. The amine-based compound according to claim 22, wherein R ₁₂ , R ₁₄ , R ₂₂ and R _{24 are} each independently selected from -F; -CN; -CH ₂ F; -CHF ₂ ; -CF ₃ ; a group consisting of a group represented by the following Chemical Formula 2 (1) to Chemical Formula 2 (14): Wherein in the chemical formula 2 (1) to the chemical formula 2 (14), each of Z ₁₁ to Z _{18 is} independently a hydrogen atom, a halogen atom, -F, -Cl, -Br, -I, -CN, a hydroxyl group, -NO ₂ , amino, formamidine, hydrazine, hydrazine, carboxyl or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkane substituted with at least one -F A C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a fluorenyl group, a pyridyl group, a triazinyl group or a carbazolyl group; wherein * represents a bonding position. The amine-based compound of claim 1, wherein X ₁ is substituted or unsubstituted phenyl, substituted or unsubstituted extended cyclopentadienyl, substituted or unsubstituted An extended or unsubstituted anthranyl group, a substituted or unsubstituted stretch group, a substituted or unsubstituted stretched cycloheptatrienyl group, substituted or unsubstituted stretched Cyclopentadienylphenyl, substituted or unsubstituted hydrazino, substituted or unsubstituted hydrazino, substituted or unsubstituted propylene naphthyl, substituted or unsubstituted Phenanthrenyl, substituted or unsubstituted thiol, substituted or unsubstituted extended alkadiene fluorenyl, substituted or unsubstituted stretched triphenyl, substituted or unsubstituted Derivatized, substituted or unsubstituted thiol, substituted or unsubstituted fused tetraphenyl, substituted or unsubstituted thiol, substituted or unsubstituted hydrazine, Substituted or unsubstituted pentaphenyl, substituted or unsubstituted hexaphenyl, substituted or unsubstituted Pyrrrolyl, substituted or unsubstituted extended pyrazolyl, substituted or unsubstituted extended imidazolyl, substituted or unsubstituted extended imidazolinyl, substituted or unsubstituted extended imidazolium pyridyl Substituted or unsubstituted imidazolidinyl, substituted or unsubstituted extended pyridyl, substituted or unsubstituted extended pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or Unsubstituted hydrazino, substituted or unsubstituted hydrazino, substituted or unsubstituted quinolinyl, substituted or unsubstituted hydrazinyl, substituted or unsubstituted a hydrazine, a substituted or unsubstituted anthranilyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted fluorenyl group, substituted or unsubstituted Extended oxazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted thiophene Meryl, substituted or unsubstituted extended alkenyl, substituted or unsubstituted extended furanyl, Substituted or unsubstituted benzofuranyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted isothiazolyl, substituted Or unsubstituted benzoimidazolyl, substituted or unsubstituted isoxazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, Substituted or unsubstituted threazine, substituted or unsubstituted oxadiazole, substituted or unsubstituted hydrazinyl, substituted or unsubstituted terazolyl or substituted or Unsubstituted tetrazolium. The amine-based compound according to claim 1, wherein X ₁ is a substituted or unsubstituted phenyl, substituted or unsubstituted anthranyl group, substituted or unsubstituted hydrazine group. Substituted or unsubstituted phenanthrenyl, substituted or unsubstituted hydrazine, substituted or unsubstituted stretched triphenyl, substituted or unsubstituted thiol, substituted or Unsubstituted anthracenyl, substituted or unsubstituted stretched pyridyl, substituted or unsubstituted extended pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted stretched Quinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted Benzofuranyl, substituted or unsubstituted threazine, substituted or substituted or unsubstituted oxazinyl, substituted or unsubstituted terazolyl or substituted or unsubstituted stretching Tetrazolyl. The amine-based compound according to claim 1, wherein X _{1 is a group represented} by one of the following Chemical Formula 5 (1) to Chemical Formula 5 (16): Wherein in the Chemical Formula 5 (1) 5 to Chemical Formula (16), Z ₁ to Z ₈ are each independently a hydrogen atom; a deuterium atom; -F; -Cl; -Br; -I ; -CN; hydroxy; -NO ₂ Amino group; formazan group; anthracene; anthracene; a carboxyl group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphate group or a salt thereof; a C ₁ - C ₂₀ alkyl group; a C ₁ - C ₂₀ alkoxy group; -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, formamidine, hydrazine, hydrazine, carboxyl or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphate group or a salt thereof At least one substituted C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ aryl group; C ₂ -C ₂₀ heteroaryl group; and ruthenium atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, methionyl, anthracene, fluorene, carboxy or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₂₀ alkyl group at least one C ₁ -C ₂₀ alkoxy, C ₆ -C ₂₀ aryl and C ₂ -C ₂₀ heteroaryl group substituted with aryl of C ₆ -C ₂₀ aryl and C ₂ -C ₂₀ heteroaryl wherein One; wherein * represents the bonding position to the oxime in Chemical Formula 1; and wherein *' represents the bonding position to N in Chemical Formula 1. The scope of patent application 26 of the amine compound, wherein Z ₁ to Z ₈ are each independently a hydrogen atom; a deuterium atom; -F; -Cl; -Br; -I ; -CN; hydroxy; -NO ₂ Amino group; formazan group; anthracene; anthracene; a carboxyl group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphate group or a salt thereof; a methyl group, an ethyl group, a propyl group, a butyl group and a pentyl group; Base, propoxy, butoxy and pentyloxy; ruthenium atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, formamidine, oxime, oxime, carboxyl Methyl, ethyl, propyl, butyl, pentyl, methoxy, ethoxy, propoxy, butyl substituted by at least one of its salt, sulfonic acid group or its salt, phosphate group or a salt thereof Oxyl and pentyloxy; phenyl, naphthyl, anthracenyl, phenanthryl, anthracenyl, and fluorenyl; pyridyl, pyrimidinyl, triazinyl, quinolinyl and oxazolyl; fluorene atom, -F , -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, formamidine, hydrazine, hydrazine, carboxyl or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, C ₁ - at least one of the phenyl substituted C ₂₀ alkyl group, and C ₁ -C ₂₀ alkoxy group, a naphthyl group, anthracenyl group, phenanthrene , One pyrenyl, fluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, carbazolyl and the. An amine compound as described in claim 1, wherein m is 1, 2 or 3. The amine-based compound according to claim 1, wherein the amine-based compound is one of the following compounds 1 to 109: An organic light emitting diode comprising a first electrode, a second electrode disposed opposite to the first electrode, and an organic layer disposed between the first electrode and the second electrode, the organic layer comprising at least one An amine compound as described in claim 1 of the patent application. An organic light-emitting diode according to claim 30, wherein the The machine layer comprises a hole injection layer, a hole transmission layer, a functional layer having both hole injection and hole transmission capability, a buffer layer, an electron blocking layer, a light emitting layer, a hole blocking layer, and a hole At least one of an electron transport layer, an electron injection layer, and a functional layer having both electron transport and electron injection capabilities. The organic light-emitting diode according to claim 31, wherein the organic layer comprises the electron transport layer, and the amine compound is contained in the electron transport layer. The organic light-emitting diode according to claim 32, wherein the electron transport layer further comprises a metal complex. The organic light-emitting diode according to claim 33, wherein the metal complex is lithium quinolate. The organic light-emitting diode according to claim 31, wherein the organic layer comprises the light-emitting layer, and the amine compound is contained in the light-emitting layer. The organic light-emitting diode according to claim 35, wherein the amine compound in the light-emitting layer is used as a substrate, and the light-emitting layer further comprises a blue fluorescent dopant. The organic light-emitting diode according to claim 35, wherein the amine compound in the light-emitting layer is used as a dopant, and the light-emitting layer further comprises an onion compound represented by the following chemical formula 400 and the following chemical formula 401 represents at least one of the onion compounds: Wherein in Chemical Formula 400 and Chemical Formula 401, Ar ₁₁₁ and Ar _{112 are} each independently a substituted or unsubstituted C ₆ -C ₆₀ extended aryl group; and Ar ₁₁₃ to Ar ₁₁₆ and Ar ₁₂₂ to Ar _{125 are} each independently a substituted or unsubstituted C ₁ -C ₁₀ alkyl group or a substituted or unsubstituted C ₆ -C ₆₀ aryl group; Ar ₁₂₆ and Ar _{127 are} each independently a C ₁ -C ₁₀ alkyl group; and g, h , i, j, k and l are each independently an integer from 0 to 4. The organic light-emitting diode according to claim 37, wherein Ar ₁₁₁ and Ar _{112 are} each independently a phenyl, anthracenyl, phenanthrenyl or anthracene group; or a phenyl group, a naphthyl group and a phenyl group, an anthranyl group, a phenanthrenyl group, a fluorenyl group or a fluorenyl group substituted with at least one of the fluorenyl groups; Ar ₁₁₃ to Ar ₁₁₆ and Ar ₁₂₂ to Ar _{125 are} each independently a phenyl group or a naphthyl group. And a C ₁ -C ₁₀ alkyl group substituted with at least one of a fluorenyl group; a phenyl group; a naphthyl group; an anthracenyl group; an anthracenyl group; a phenanthryl group; a fluorenyl group; a fluorene atom, a halogen atom, a hydroxyl group, a cyano group, -NO ₂ Or an amino group, a decyl group, an anthracene, an anthracene, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ - Phenyl, naphthyl, anthracenyl, fluorenyl, substituted with at least one of C ₆₀ alkynyl, C ₁ -C ₆₀ alkoxy, phenyl, naphthyl, anthracenyl, fluorenyl, phenanthryl and anthracenyl Fiji and thiol; and One of them; Ar ₁₂₆ and Ar _{127 are} each independently methyl, ethyl or propyl; and g, h, i, j, k and l are each independently 0, 1 or 2. The organic light emitting diode according to claim 31, wherein the organic layer comprises at least the hole injection layer, the hole transport layer, and the functional layer having both hole injection and hole transport capability. And wherein at least one of the hole injection layer, the hole transport layer, and the functional layer having both hole injection and hole transport capability comprises a p dopant.