TWI681945B - 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 compounds and organic light-emitting diodes containing the same

Cross-reference of related applications

This application claims that the Korean application filed on February 07, 2012 with the Korean Intellectual Property Agency was 10-2012-0012532 and the Korean application filed with the Korean Intellectual Property Agency on June 08, 2012 was 10-2012-0061676. The entire contents of equity are incorporated here by reference.

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

Organic light emitting diodes (OLEDs) are self-emitting diodes that have the advantages of, for example, wide viewing angle, good contrast, fast response, high brightness, and good driving voltage, and can provide color images.

The conventional organic light emitting diode includes a structure having a substrate, and an anode, a hole transport layer (HTL), a light emitting 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 layer are organic thin films containing organic compounds.

The operating principle of the organic light emitting diode with the above structure is as follows.

When a voltage is applied between the anode and the cathode, holes injected from the anode move to the light emitting layer through the hole transport layer, and electrons injected from the cathode move to the light emitting layer through the electron transport layer. The holes and electrons recombine in the light-emitting layer to generate excitons. The excitons emit light when they fall back from the excited state to the ground state.

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

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

Among them, 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 arylene group or substituted or unsubstituted C ₂ -C ₆₀ arylene group; m is an integer from 1 to 5; and each substituted C ₆ -C At least one substituent of ₆₀ aryl, substituted C ₂ -C ₆₀ heteroaryl, substituted C ₆ -C ₆₀ aryl aryl and substituted C ₂ -C ₆₀ aryl aryl is a deuterium atom;- F; -Cl; -Br; -I; -CN; hydroxyl; -NO ₂ ; amino; formamidine; hydrazine; hydrazone; carboxyl or its salt; sulfonic acid or its salt; phosphate or its salt; tri( C ₆ -C ₆₀ aryl) silane group; C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group; via deuterium atom, -F , -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, carboxamidine, hydrazone, hydrazone, carboxyl group or its salt, sulfonic acid group or its salt, or at least one of phosphate group or its salt 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, C ₆ -C ₆₀ arylthio; deuterium Atom, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, formamidine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, phosphate group or its salt , C ₁ -C ₆₀ alkyl, with at least one fluorine (F) of the substituted C ₁ -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group at least one of substituents C C ₆ -C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group ₃ -C ₆₀ cycloalkyl, C ₃ -C ₆₀ cycloalkenyl, C ₆ -C ₆₀ aryl, C _{One of 2} -C ₆₀ heteroaryl, C ₆ -C 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 ; C ₁ -C ₆₀ alkyl substituted with at least one -F; C ₂ -C ₆₀ heteroaryl; and Deuterium atom, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, formamidine, hydrazine, hydrazone, carboxyl group or its salt, sulfonic acid group or its salt, phosphate group or its salts, C ₁ -C ₆₀ alkyl, -F substituted with at least one of C ₁ -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, 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 consisting of at least one electron withdrawing substituent of C ₆ -C ₆₀ aryl group.

According to another aspect of the present invention, there is provided an organic light emitting diode including 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 includes At least one amine compound.

10‧‧‧ organic light emitting diode

11‧‧‧ substrate

13‧‧‧First electrode

15‧‧‧ Organic layer

17‧‧‧Second electrode

By describing the exemplary embodiments in detail with reference to the accompanying drawings, the above and other features and advantages of the present invention will become apparent and easy to understand, among which: FIG. 1 is a schematic diagram illustrating the structure of an organic light emitting diode according to an embodiment.

As used herein, the term "and/or" includes any or all combinations of one or more related listed elements. When an expression such as "at least one" is prefixed to a row of elements, it modifies the entire row of elements rather than the individual elements in that row.

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

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

At least at least one of each substituted C ₆ -C ₆₀ aryl group, substituted C ₂ -C ₆₀ heteroaryl group, substituted C ₆ -C ₆₀ aryl group and substituted C ₂ -C ₆₀ aryl group A substituent may be a deuterium atom; -F; -Cl; -Br; -I; -CN; hydroxyl; -NO ₂ ; amino; carboxamidine; hydrazine; hydrazone; carboxyl or its salt; sulfonic acid or its salt ; Phosphoric acid group or its salt; tri(C ₆ -C ₆₀ aryl) silane group; C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₂ -C ₆₀ alkenyl group and C ₂ -C ₆₀ Alkynyl; via deuterium atom, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, carboxamidine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt or C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₂ -C ₆₀ alkenyl group and C ₂ -C ₆₀ alkynyl group substituted with at least one of a phosphate group or a salt thereof; 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; via deuterium atom, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, carboxamidine, hydrazine, hydrazone, carboxyl or its salt, sulfonate or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl, substituted by at least one of fluorine (F) 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 -C ₆₀ heteroaryl substituted with at least one C ₃ -C ₆₀ cycloalkyl, C ₃ -C ₆₀ cycloalkenyl, C _{One of 6} -C ₆₀ aryl, C ₂ -C ₆₀ heteroaryl, C ₆ -C ₆₀ aralkyl, C ₆ -C ₆₀ aryloxy, and C ₆ -C ₆₀ arylthio.

In the above Chemical Formula 1, at least one of Ar ₁ and Ar ₂ is selected from -F; -CN; -NO ₂ ; C ₁ -C ₆₀ alkyl substituted with at least one -F; C ₂ -C ₆₀ hetero Aryl; and via deuterium atom, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, carboxamidine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt , a phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl, -F substituted with at least one of C ₁ -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy, C ₂ -C ₆₀ alkenyl, C ₂ - C ₆ -C ₆₀ alkynyl, C ₆ -C ₆₀ aryl and C ₂ -C ₆₀ heteroaryl substituted with at least one C ₂ -C ₆₀ heteroaryl group consisting of at least one electron-withdrawing group substituted C _6- C ₆₀ aryl.

For example, at least one electron-withdrawing group may be selected from: -F; -CN; -NO ₂ ; C ₁ -C ₂₀ alkyl substituted with at least one -F; including ring-forming N atom (ring-forming N atom) C ₂ -C ₂₀ heteroaryl group; and containing ring forming N atom and deuterium atom, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, formamidinyl, hydrazine, 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 ₂₀ alkyl, -F substituted with at least one of C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy 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 electron withdrawing group in Chemical Formula 1 may be selected from -F; -CN; C ₁ -C ₂₀ alkyl substituted with at least one -F; pyrrolyl (pyrrolyl group), pyrazolyl ( 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, phthalazine Phthalazinyl group, indolizinyl group, quinazolinyl group, quinazolinyl group, cirnnolinyl group, indazolyl group, carbazolyl group, phenazine Phenazinyl group, phenanthridinyl group, triazinyl group, pyridazinyl group, triazolyl group and tetrazolyl group and deuterated atoms, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, carboxamidine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkyl substituted with at least one -F, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, phenanthrenyl group, pyrenyl ( pyrenyl group), pyridyl, triazinyl and carbazolyl substituted pyrrolyl, pyrazolyl, imidazolyl, imidazolinyl, imidazolidinyl, imidazolylpyrimidinyl, pyridinyl, pyrazinyl, pyrimidine Group, benzimidazolyl, indolyl, purinyl, quinolinyl, isoquinolinyl, pyrazinyl, indolizinyl, quinazolinyl, cinnolinyl, indazolyl, carbazolyl, phen The group consisting of aziridinyl, phenanthridinyl, triazinyl, pyridazinyl, triazolyl and tetrazolyl.

For example, at least one electron withdrawing group in Chemical Formula 1 may be selected from: F; -CN; C ₁ -C ₂₀ alkyl substituted with at least one -F; pyridyl, pyrazinyl, pyrimidinyl, quinolinyl , Isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl; and deuterium atoms, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, formamidine group, 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 ₂₀ alkyl, -F substituted with at least one of C ₁ -C ₂₀ alkyl, C ₁ - C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, pyridyl, triazinyl and carbazolyl substituted pyridyl, pyrazinyl, pyrimidinyl, quinolinyl , Isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl and carbazolyl, but not limited to this group.

In some embodiments, at least one electron-withdrawing group 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 formed by the indicated groups:

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 deuterium atom, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO _2. Amino, formamidine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ substituted with at least one -F Alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, pyridyl, triazinyl or carbazolyl.

For example, Z ₁₁ to Z ₁₈ in the above Chemical Formula 2(1) to Chemical Formula 2(14) may be independently hydrogen atom, deuterium atom, -F, -Cl, -Br, -I, -CN, hydroxyl group , -NO ₂ , amino, carboxamidine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, phosphoric acid or its salt, methyl, ethyl, propyl, butyl, pentyl, methoxy Group, ethoxy group, propoxy group, butoxy group, pentyloxy group, phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, pyridyl group, triazinyl group or carbazolyl group, but not limited to this, * Indicates the bonding 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 phenyl, biphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, or fluorenyl group substituted with at least two electron withdrawing groups ). The electron withdrawing group may be independently selected from pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl and carbazolyl; via deuterium atom, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, carboxamidine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, phosphate or its salt, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkyl substituted with at least one -F, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, pyridyl, tri Pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, phthalazinyl, benzimidazolyl and carbazolyl 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 electron withdrawing group. 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), ring A and ring B 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 ; C ₁ -C ₆₀ alkyl substituted with at least one -F; C ₂ -C ₆₀ heteroaryl; and deuterium atom, -F, -Cl, -Br, -I, -CN , Hydroxyl, -NO ₂ , amino, carboxamidine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, phosphate or its salt, C ₁ -C ₆₀ alkyl, substituted by at least one -F 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 -C ₆₀ heteroaryl An electron-withdrawing group consisting of at least one substituted 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, so their detailed description will not be repeated here.

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

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

In some embodiments, the amine compound can be represented by the above Chemical Formula 1(1), wherein the A ring in Chemical Formula 1(1) can be substituted phenyl, substituted biphenyl, substituted naphthyl, Substituted anthracenyl, substituted phenanthrenyl, substituted pyrene or substituted fluorenyl, but not limited thereto.

In some embodiments, the amine compound can be represented by the above Chemical Formula 1(2), wherein the A ring and the B ring in the Chemical Formula 1(2) can each independently be substituted phenyl, substituted biphenyl, Substituted naphthyl, substituted anthracenyl, substituted phenanthrenyl, substituted pyrene or substituted stilbyl.

In some embodiments, the amine compound may be represented by Chemical Formula 1(1), wherein ring A may be substituted phenyl, substituted biphenyl, substituted naphthyl, substituted anthryl, substituted Phenanthrenyl, substituted pyrenyl or substituted fluorenyl; R ₁ can be selected from pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzene Imidazolyl and carbazolyl; with deuterium atom, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, carboxamidine, hydrazine, hydrazone, carboxyl or its salt, sulfonate acid group or a salt thereof, a phosphoric acid 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 group, a phenyl group, a naphthyl group, Anthryl, phenanthryl, pyrenyl, pyridyl, triazinyl and carbazolyl substituted pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, phthalide At least one electron-withdrawing group of the group consisting of aziridinyl, benzimidazolyl, and carbazolyl; and p may be 2, 3, or 4, for example, 2.

In some other embodiments, the amine compound can be represented by Chemical Formula 1(2), wherein ring A and ring B can each independently be substituted phenyl, and ring A can be substituted phenyl, substituted biphenyl Group, substituted naphthyl group, substituted anthracenyl group, substituted phenanthrenyl group, substituted pyrene group or substituted fluorenyl group; R ₁ and R ₂ may each independently be selected from pyridyl, pyrazinyl , Pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl and carbazolyl; with deuterium atoms, -F, -Cl, -Br, -I, -CN , Hydroxyl, -NO ₂ , amino, carboxamidine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C ₁ -C ₂₀ alkyl, substituted by at least one -F P ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, phenanthryl, pyrenyl, pyridyl, triazinyl and carbazolyl substituted pyridyl , Pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, phthalazinyl, benzimidazolyl, and carbazolyl; at least one electron-withdrawing group; and p and q may Each is independently an integer of 2, 3, or 4, for example, all may be integers of 2.

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

In the above Chemical Formula 1, Ar ₁ and Ar ₂ may each independently be substituted or unsubstituted phenyl, substituted or unsubstituted pentalenyl group, substituted or unsubstituted Indenyl group, substituted or unsubstituted naphthyl, substituted or unsubstituted azulenyl group, substituted or unsubstituted heptalenyl group, Substituted or unsubstituted dicyclopentadienyl (indacenyl group), substituted or unsubstituted acenaphthyl group, substituted or unsubstituted stilbene, substituted or unsubstituted Propylene naphthyl (phenalenyl group), substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthryl, substituted or unsubstituted propadienyl group (fluoranthenyl group), substituted Or unsubstituted triphenylenyl group, substituted or unsubstituted pyrenyl, substituted or unsubstituted chrysenyl group, substituted or unsubstituted fused tetraphenyl ( naphthacenyl group), substituted or unsubstituted picenyl group, substituted or unsubstituted perylenyl group, substituted or unsubstituted pentaphenyl group, substituted or Unsubstituted fused hexaphenylyl group, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted Imidazolinyl, substituted or unsubstituted imidazolyl, pyridyl substituted or unsubstituted, pyridyl substituted or unsubstituted, pyrazinyl substituted or unsubstituted, substituted Or unsubstituted pyrimidinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted purinyl, substituted or unsubstituted quinoline Group, substituted or unsubstituted phthalazinyl, substituted or unsubstituted indolizinyl, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted quinazoline Group, substituted or unsubstituted cinnoline, substituted or unsubstituted indazolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted Substituted phenanthridinyl, substituted or unsubstituted pyranyl group, substituted or unsubstituted chromenyl group, substituted or unsubstituted furanyl group , Substituted or unsubstituted benzofuranyl (benzofura nyl group), substituted or unsubstituted thienyl group, substituted or unsubstituted benzothienyl group, substituted or unsubstituted isothiazolyl group, substituted Or unsubstituted benzoimidazolyl group, substituted or unsubstituted isoxazolyl group, substituted or unsubstituted dibenzothienyl group, substituted or Unsubstituted dibenzofuranyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted pyridazine Radical, substituted or unsubstituted triazolyl, substituted or unsubstituted tetrazolyl or substituted or unsubstituted phenanthrolinyl group. At least one of Ar ₁ and Ar ₂ may be phenylbiphenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, or sulfenyl substituted with at least one electron withdrawing group listed above.

For example, Ar ₁ and Ar ₂ in the above Chemical Formula 1 may each independently be substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted stilbene, Substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted biphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted quinyl , 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 dibenzothienyl, 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, quinolinyl, iso Quinolinyl, quinazolinyl, triazinyl, benzimidazolyl and carbazolyl; and deuterium atoms, -F, -Cl, -Br, -I, -CN, hydroxyl, -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 ₂₀ alkyl, -F substituted with at least one of C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, pyridyl, triazinyl and carbazolyl substituted pyridyl, pyrazinyl, pyrimidinyl, quino Phenyl, isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl and carbazolyl at least one electron-withdrawing group substituted phenyl, biphenyl, naphthyl, anthracenyl, Phenyl, pyrene or fluorenyl.

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 described above in conjunction 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 R ₁₁ to R ₁₇ in Chemical Formula 1C and Chemical Formula 1D, at least one of R ₁₁ to R ₁₈ in Chemical Formula 1E and Chemical Formula 1J At least one of R ₁₁ to R ₁₉ in Chemical Formula 1F and Chemical Formula 1G, Chemical Formula 1H and Chemical Formula 1I may each independently be selected from -F; -CN; -NO ₂ ; C ₁ -substituted with at least one -F C ₆₀ alkyl; C ₂ -C ₆₀ heteroaryl; and deuterium atom, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, formamidinyl, hydrazine, 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 ₆₀ alkyl, -F substituted with at least one of C ₁ -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy, A group consisting of C ₂ -C ₆₀ heteroaryl substituted with at least one of C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₆ -C ₆₀ aryl and C ₂ -C ₆₀ heteroaryl The electronic base.

For example, the formula 1A and Chemical Formula 1B in the R ₁₁ to R is at least one, the formula 1C and Chemical Formula 1D, the R ₁₅ at least one, of formula 1E Chemical Formula 1J in the R and ₁₁ to R ₁₇ is ₁₁ to R ₁₈ At least one of and at least one of R ₁₁ to R ₁₉ in Chemical Formula 1F and Chemical Formula 1G, Chemical Formula 1H and Chemical Formula 1I may each independently be selected from -F; -CN; C ₁ -substituted with at least one -F C ₂₀ alkyl; pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl and carbazolyl; via deuterium atom, -F,- Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, carboxamidine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C ₁ -C ₂₀ Alkyl, C ₁ -C ₂₀ alkyl substituted with at least one -F, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, pyridyl, triazinyl and carbo Pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, phthalazinyl, triazinyl, benzimidazolyl and carbazolyl The electronic group of the group 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, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl and carbazolyl; with deuterium atoms, -F, -Cl, -Br, -I, -CN, Hydroxy, -NO ₂ , amino, carboxamidine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C ₁ -C ₂₀ alkyl, C substituted with at least one -F Pyridyl substituted with at least one of ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, phenanthryl, pyrenyl, pyridyl, triazinyl and carbazolyl, Benzene substituted by at least one electron-withdrawing group consisting of pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, phthalazinyl, triazinyl, benzimidazolyl and carbazolyl Group, biphenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group or fluorenyl group.

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 be independently selected from pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquino Porphyrinyl, quinazolinyl, triazinyl, benzimidazolyl and carbazolyl; with deuterium atoms, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, methyl amidino, 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 ₂₀ alkyl, -F substituted with at least one of C ₁ -C ₂₀ -alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, pyridyl, triazinyl and carbazolyl substituted pyridyl, pyrazinyl, pyrimidinyl, quinoline Group, isoquinolinyl, quinazolinyl, phthalazinyl, benzimidazolyl and carbazolyl group; and Ar ₂ may be substituted or unsubstituted phenyl, substituted Or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, Substituted or unsubstituted stilbene.

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

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 be independently represented by the above Chemical Formula 2(2), but not limited to this.

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

In Chemical Formula 1, X ₁ may be substituted or unsubstituted phenylene group, substituted or unsubstituted pentanenylene group, substituted or unsubstituted Indenylene group, substituted or unsubstituted naphthylene group, substituted or unsubstituted azulenylene group, substituted or unsubstituted pendant cycloheptane Alkenyl (heptalenylene group), substituted or unsubstituted indacenylene group (indacenylene group), substituted or unsubstituted acenaphthylene group (acenaphthylene group), substituted or unsubstituted extension Fluorenylene group, substituted or unsubstituted phenalenylene group, substituted or unsubstituted phenanthrenylene group, substituted or unsubstituted phenanthrenylene group ( anthrylene group), substituted or unsubstituted fluoranthenylene group, substituted or unsubstituted triphenylenylene group, substituted or unsubstituted pyrenyl group (pyrenylene group), substituted or unsubstituted chrysenylene group, substituted or unsubstituted naphthacenylene group, substituted or unsubstituted picenylene group ), substituted or unsubstituted 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 Substituted imidazolinylene group, substituted or unsubstituted imidazopyridinylene group, substituted or unsubstituted imidazopyrimidinylene group, substituted or unsubstituted Pyridinyl gr oup), substituted or unsubstituted pyrazinylene group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted indolylene 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 Substituted 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 unsubstituted Chromenylene group, substituted or unsubstituted furanylene group, substituted or unsubstituted benzofuranylene group, substituted or unsubstituted thiophene group (thienylene group), substituted or unsubstituted benzothienylene group, substituted or unsubstituted isothiazolylene group, substituted or unsubstituted benzimidazolyl (benzoimidazolylene group), substituted or unsubstituted isoxazolylene group, substituted or unsubstituted dibenzothienylene group, substituted or unsubstituted dibenzothienylene group Dibenzofuranylene group, substituted or unsubstituted triazinylene group, substituted or unsubstituted oxadiazolylene group, substituted or unsubstituted pyridazinyl group ( pyri dazinylene group), substituted or unsubstituted triazolylene group (triazolylene group) or substituted or unsubstituted tetrazolylene group (tetrazolylene group). X ₁ in the chemical formula may have at least one substituent selected from the above-mentioned substituents.

In some embodiments, X ₁ in Chemical Formula 1 may be, but not limited to, substituted or unsubstituted phenylene, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, Substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted Substituted quinolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinidine Quinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted diphenylthiophene P-furanyl, substituted or unsubstituted triazinyl, substituted or substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazolyl, or substituted or unsubstituted stretch IV Oxazolyl.

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) to Chemical Formula 5(16), Z ₁ to Z ₈ may each independently be a hydrogen atom; a deuterium atom; -F; -Cl; -Br; -I; -CN; hydroxyl; -NO ₂ ; Amino; Carboxyamidine; Hydroxy; Hydrazone; Carboxy or its salt; Sulfonic acid or its salt; Phosphoric acid or its salt; C ₁ -C ₂₀ alkyl; C ₁ -C ₂₀ alkoxy; -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, formamidine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, phosphoric acid or its salt at least One substituted C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy; C ₆ -C ₂₀ aryl; C ₂ -C ₂₀ heteroaryl; via deuterium atom, -F, -Cl, -Br , -I, -CN, hydroxyl, -NO ₂ , amino, carboxamidine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C ₁ -C ₂₀ alkyl, 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), * indicates to Chemical Formula 1 The bonding position of anthracene, and *'represents the bonding position to N in 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 deuterium atom; -F; -Cl; -Br; -I; -CN; hydroxyl; -NO ₂ ; amino; carboxamidine; hydrazone; hydrazone; carboxyl or its salt; sulfonic acid or its salt; phosphate or its salt; methyl, ethyl, propyl, butyl and pentyl; methoxy , Ethoxy, propoxy, butoxy and pentyloxy; via deuterium atom, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, formamidinyl, hydrazine, Methyl, ethyl, propyl, butyl, pentyl, methoxy, ethoxy, propoxy substituted by at least one of hydrazone, carboxyl group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt Group, butoxy and pentyloxy; phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl; pyridyl, pyrimidinyl, triazinyl, quinolinyl and carbazolyl; via deuterium atoms, -F, -Cl, -Br, -I, -CN, hydroxy, -NO ₂ , amino, carboxamidine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, naphthyl, anthracenyl, pyridyl substituted phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl , Pyridyl, pyrimidinyl, triazinyl, quinolinyl and carbazolyl, but not limited to this.

In Chemical Formula 1, m is an integer of 1 to 5, and in some embodiments, 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 via -F; -CN; -NO ₂ ; C ₁ -C ₆₀ alkyl substituted with at least one -F; C ₂ -C ₆₀ Heteroaryl; and deuterium atom, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, carboxamidine, hydrazine, hydrazone, carboxyl or its salt, sulfonate or its Salt, phosphate group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₆ -C ₆₀ aryl group and C substituted with at least one of C ₂ -C ₆₀ heteroaryl group of group ₂ -C ₆₀ heteroaryl groups substituted with at least one electron withdrawing group of C ₆ -C ₆₀ aryl group, a 1 'of "the formula A1 "It means that the part can pull electrons.

The amine compound of Chemical Formula 1'has an electron-rich naphthalene-anthracene core and an A1 portion with electron-pulling ability, and therefore 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 connected to the C ₆ -C ₆₀ aryl group N in chemical formula 1'. Therefore, the organic light emitting diode including the amine compound of Chemical Formula 1 can have improved efficiency characteristics. When the electron-withdrawing group is -CN, the organic light-emitting diode including the amine compound of Chemical Formula 1 may have improved service life characteristics.

Without wishing to be bound by a particular theory, either i) an amine compound containing a naphthalene-anthracene core lacking the above electron-withdrawing group or ii) any one of an amine compound containing a naphthalene-anthracene core having pyridine directly linked to N, The highest occupied molecular orbital (HOMO) electron density may be concentrated near the anthracene part. However, in the anthracene-based compound of the above Chemical Formula 1, the HOMO electron density may be scattered near the amine portion, so that the lowest unoccupied molecular orbital (LUMO) electron density may be relatively set near the anthracene. This may give the amine compound of Chemical Formula 1 improved dipole characteristics. Thus, the electron transport characteristics of the amine compound of Chemical Formula 1 can be improved.

Therefore, the organic light-emitting diode including any amine compound represented by the above Chemical Formula 1 may have a low driving voltage, high brightness, high efficiency, and long service life.

The amine compound of Chemical Formula 1 can be synthesized by a known organic synthesis method. 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 Chemical Formula 1 can be used between the counter electrodes of one of the organic light emitting diodes. For example, at least one amine-based compound may be in the light-emitting layer and/or between the cathode and the light-emitting layer (for example, 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 this embodiment, the organic light emitting diode includes 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, wherein the organic layer includes at least one The amine compound of the above Chemical Formula 1.

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

In some embodiments, the organic layer may only contain Compound 1 as the amine compound. Compound 1 can be in the light-emitting layer or the electron transport layer of the organic light-emitting diode. In some embodiments, the organic layer may include Compound 1 and Compound 3 as amine compounds. Compound 1 and compound 3 may be in the same layer (for example, in the 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 include a hole injection layer (HIL), a hole transport layer (HTL), a functional layer having both hole injection and hole transport capabilities (hereinafter referred to as an H-functional layer), a buffer layer, and an electron blocking layer Layer (EBL), light-emitting layer (EML), hole blocking layer (HBL), electron transport layer (ETL), electron injection layer (EIL), and functions with both electron injection and electron transport capabilities At least one layer between layers (hereinafter referred to as E-functional layer).

The term "organic layer" used herein means a single layer and/or a plurality of layers between the first electrode and the second electrode of the organic light emitting diode.

The organic layer may include a light-emitting layer, wherein at least one amine-based compound may be included in the light-emitting layer.

The amine compound in the light-emitting layer can be used as a matrix. When the amine compound in the light-emitting layer is used as a matrix, the light-emitting layer may further contain a fluorescent dopant. The fluorescent dopant may be a blue fluorescent dopant. In some embodiments, the amine compound in the light-emitting 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 may include an electron transport layer, wherein at least one amine compound may be included in the electron transport layer.

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

The substrate 11 may be any substrate used for existing organic light emitting diodes. In some embodiments, the substrate 11 may be, for example, a glass substrate or a transparent plastic substrate with strong mechanical strength, thermal stability, transparency, smooth surface, easy handling, and waterproofness.

The first electrode 13 can 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 with 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), magnesium-silver (Mg-Ag), etc. It is a reflective electrode.

The first electrode 13 may have a single-layer structure or a multi-layer structure including at least two layers. For example, the first electrode 13 may have a three-layer structure of ITO/silver/ITO, but it 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, a buffer layer, a light emitting layer, an electron transport layer, and an electron injection layer.

The hole injection layer may be formed on the first electrode 13 by vacuum deposition, spin coating, casting, Lanmul-Brugge (LB) deposition, or the like.

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

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

The hole injection layer may include any material commonly used to form a 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. Copper phthalocyanine compound, 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (4,4',4"-tris(3-methylphenylphenylamino)triphenylamine,m-MTDATA) , N,N'-bis(1-naphthyl)-N,N'-diphenylbenzidine (N,N'-di(1-naphthyl)-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 sulfonicacid (Pani/CSA) or polyaniline/poly(4-sulfostyrene) (polyaniline/ poly(4-styrenesulfonate), PANI/PSS), but not limited to this.

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

Next, the hole transport layer may be formed on the hole injection layer by vacuum deposition, spin coating, casting, or Lamborg-Brogee (LB) deposition. When the hole transport layer uses true When forming by vacuum deposition or spin coating, although the deposition or coating conditions may vary according to the material used to form the hole transport layer, the deposition or coating conditions may be similar to those used to form the hole injection layer.

Non-limiting examples of suitable conventional hole transport materials are, for example, N-phenylcarbazole, polyvinylcarbazole, carbazole derivative, N,N'-bis (3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (N,N'-bis(3-methylphenyl)-N,N '-diphenyl-[1,1-biphenyl]-4,4'-diamine,TPD), 4,4',4"-tri(N-carbazole) triphenylamine (4,4',4"-tris( N-carbazolyl)triphenylamine,TCTA),N,N'-bis(1-naphthyl)-N,N'-diphenylbenzidine (N,N'-di(1-naphthyl)-N,N'- diphenylbenzidine), NPB).

The thickness of the hole transport layer can be about 50Å to about 2,000Å, and in some embodiments, can be about 100Å to about 1,500Å. When the thickness of the hole transmission layer is within this range, the hole transmission layer can obtain good hole transmission capacity without significantly increasing the driving voltage.

The H-functional layer (a functional layer having both hole injection and hole transmission capabilities) may include at least one material from each group of hole injection layer materials and hole transmission layer materials. H- The thickness of the functional layer may be about 100Å to about 10,000Å, and in some embodiments, may be about 100Å to about 1,000Å. When the thickness of the H-functional layer is within this range, there is no need to significantly increase the driving voltage, the H-functional layer can have good hole injection and transmission capabilities.

In some embodiments, at least one of the hole injection layer, the hole transport layer, and the H-functional layer may include at least one of the compound of Chemical Formula 300 and the compound of Chemical 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 arylene group, and Ar ₂₁ and Ar ₂₂ may each independently be a substituted or unsubstituted Substituted C ₆ -C ₆₀ aryl. Ar ₁₁ and Ar ₁₂ may independently be phenylene, naphthyl, phenanthrenyl, and pyrenyl; and phenylene, naphthyl, and naphthyl substituted with at least one of phenyl, naphthyl, and anthryl. Sphenanthrene, Stilbene and Pyrene. Ar ₂₁ and Ar ₂₂ may each independently be phenyl, naphthyl, phenanthrenyl, and pyrenyl; and phenyl, naphthyl, phenanthrenyl, fluorenyl substituted with at least one of phenyl, naphthyl, anthracenyl And one of the midterms of Pyrene.

In the chemical formula 300, e and f may each independently be an integer of 0 to 5, for example, may 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 deuterium atom, a halogen atom, a hydroxyl group, a cyano group, -NO ₂ , an amino group, Formamidine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, phosphoric acid or its salt, substituted or unsubstituted C ₁ -C ₆₀ alkyl, 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 each independently be a hydrogen atom; a deuterium atom; a halogen atom; a hydroxyl group; a cyano group; -NO ₂ ; an amino group; Formamidine; hydrazine; hydrazone; carboxyl group or its salt; sulfonic acid group or its salt; phosphoric acid group or its salt; C ₁ -C ₁₀ alkyl group (such as methyl, ethyl, propyl, butyl, pentyl, Hexyl, etc.); C ₁ -C ₁₀ alkoxy (eg methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.); via deuterium atoms, halogen atoms, hydroxyl groups, cyano groups, -NO _2. C ₁ -C ₁₀ alkyl or C ₁ -C ₁₀ alkoxy substituted by at least one of amino, formamidine, hydrazine, hydrazone, carboxyl or its salt, sulfonic acid or its salt, and phosphoric acid or its salt Phenyl; naphthyl; anthracenyl; sulfenyl; pyrenyl; and deuterium atom, halogen atom, hydroxyl group, cyano group, -NO ₂ , amino group, formamidine group, hydrazine, hydrazone, carboxyl group or its salt, sulfonate Among acid group or its salt, phosphoric acid group or its salt, C ₁ -C ₁₀ alkyl group and C ₁ -C ₁₀ alkoxy group substituted by at least one of phenyl, naphthyl, anthracenyl, sulfonyl and pyrenyl one.

In Chemical Formula 300, R ₅₉ may be phenyl; naphthyl; anthracenyl; biphenyl; pyridyl; and deuterium atom, halogen atom, hydroxyl group, cyano group, -NO ₂ , amino group, formamidine group, hydrazine, Hydrazone, carboxyl group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C ₁ -C ₂₀ alkyl group and substituted or unsubstituted C ₁ -C ₂₀ alkoxy group At least one of substituted phenyl, naphthyl, anthracenyl, biphenyl or pyridyl.

In an 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 have the same definitions as above, so a detailed description thereof will not be provided here.

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 the hole injection layer, the hole transport layer, or the H-functional layer is in addition to the above-mentioned known hole injection materials, hole transport materials, and/or materials having both hole injection and hole transport capabilities, A charge generating material may be further included to increase the layer conductivity.

The charge generating material may be, for example, p-doped. p-doped may be quinine derivatives (quinine derivative), one of metal oxides and cyanide compounds, but not limited to this. Non-limiting examples of p dopants include, for example, tetracyanoquinonedimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-dimethylp-benzoquinone (2 , 3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane, F4-TCNQ) and other quinone derivatives; such as tungsten oxide, molybdenum oxide and other metals Oxides; and cyanide compounds such as the following compound 200.

When the hole injection layer, the hole transport layer, or the H-functional layer further includes a charge generating material, the charge generating material may be uniformly or unevenly dispersed in the layer.

The buffer layer may be disposed between at least one of the hole injection layer, the hole transport layer, or the H-functional layer and the light-emitting layer. The buffer layer can compensate for the optical resonance distance according to the wavelength of light emitted by the light emitting layer, and thus can increase efficiency. The buffer layer may include well-known hole injection materials or hole transmission materials. In some other embodiments, the buffer layer may include the same material as one of the hole injection layer, the hole transport layer, or the H-functional layer included under the buffer layer.

Next, the light emitting layer may be formed on the hole transport layer, the H-functional layer, or the buffer layer by vacuum deposition, spin coating, casting, or Lanmul-Brugge (LB) deposition. When the light emitting layer is formed using vacuum deposition or spin coating, although the deposition or coating conditions may vary according to the material used to form the light emitting layer, the deposition or coating conditions may be similar to those used to form the hole injection layer.

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

The amine compound in the light-emitting layer can be used as a dopant, such as a blue fluorescent dopant. In addition to the amine-based compound, the light-emitting layer may further include a matrix.

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

In some embodiments, an anthracene compound represented by the following chemical formula 400 may be used as a matrix.

In Chemical Formula 400, Ar ₁₁₁ and Ar _{112 are} each independently substituted or unsubstituted C ₆ -C ₆₀ arylene groups; Ar ₁₁₃ to Ar _{116 are} each independently substituted or unsubstituted C ₁ -C ₁₀ Alkyl or substituted or unsubstituted C ₆ -C ₆₀ aryl; and g, h, i and j are each independently an integer from 0 to 4.

In some non-limiting embodiments, Ar ₁₁₁ and Ar ₁₁₂ in Chemical Formula 400 may each independently be phenylene, naphthyl, phenanthrenyl, or pyrenyl; or at least one of phenyl, naphthyl, and anthracenyl One of the substituted phenylene, naphthyl, phenanthrenyl, fluorenyl group or fluorenyl group.

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

的其中之一。 In some non-limiting embodiments, Ar ₁₁₃ to Ar _{116 of} Chemical Formula 400 may each independently be C ₁ -C ₁₀ alkyl substituted with at least one of phenyl, naphthyl, or anthracenyl; phenyl; naphthyl; Anthryl; pyrenyl; phenanthryl; sulfonyl; deuterium atom, halogen atom, hydroxyl group, cyano group, -NO ₂ , amino group, formamidine group, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or Salt, phosphate group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, Phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl and stilbyl substituted with at least one of pyrenyl, phenanthrenyl and fluorenyl; and

One of them.

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

In some embodiments, an anthracene compound represented by the following chemical formula 401 may be used as a matrix.

Ar ₁₂₂ to Ar ₁₂₅ in Chemical Formula 401 may be defined as described above for Ar _{113 of} Chemical Formula 400, so a detailed description thereof will not be provided here.

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

In Chemical Formula 401, k and l may each independently be an integer of 0 to 4, such as 0, 1, or 2.

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

The amine compound in the light-emitting layer can be used as a matrix. In addition to the amine-based compound, the light-emitting layer may further contain dopants, such as blue dopants, green dopants, or red dopants.

Non-limiting examples of blue doping are compounds represented by the following chemical formula.

Non-limiting examples of red doping are compounds represented by the following chemical formula. In some embodiments, the red dopant may be DCM or DCJTB shown later.

Non-limiting examples of green dopants are compounds represented by the following chemical formulas. In some embodiments, the green dopant may be C545T presented below.

Non-limiting examples of dopants that can be used in the light-emitting layer are complex compounds represented by the following chemical formulas.

Non-limiting examples of dopants that can be used in the light-emitting layer are osmium complexes represented by the following chemical formulas.

When the light-emitting layer includes a matrix and a dopant, the amount of the dopant in the light-emitting layer may be based on 100 parts by weight of the matrix, which is approximately 0.01 to 15 parts by weight. However, the amount of doping is not limited to this range.

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

Next, the electron transport layer can 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, although the deposition or coating conditions may vary according to the material used to form the electron transport layer, the deposition or coating conditions may be different from those used to form the hole injection layer similar. The material used to form the electron transport layer may be any known material that can stably transport electrons injected from the electron injection electrode (cathode). Examples of materials used to form the electron transport layer are quinoline derivatives, such as tris (8-quinolinorate) aluminum (Alq ₃ ), TAZ, BAlq, bis (10 -Hydroxybenzo[h]quinoline) beryllium (beryllium bis (benzoquinolin-10-olate, Bebq ₂ ), 9,10-bis(naphthalen-2-yl)anthracene (ADN), compound 201 and compound 202, but not Limited to this.

The electron transport layer may contain at least one of the aforementioned amine compounds.

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

The thickness of the electron transport layer may be from about 100Å to about 1,000Å, and in some embodiments, may be from about 150Å to about 500Å. When the electron transport layer is within 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-transporting organic compounds, the electron-transporting layer may further include a metal-containing material.

The metal-containing material may be a lithium complex. Non-limiting examples of lithium complexes are lithium quinolate (Liq) and the following compound 203:

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

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

The thickness of the electron injection layer may be from about 1Å to about 100Å, and in some embodiments, may be from about 3Å to about 90Å. When the thickness of the electron injection layer is within this range, the electron injection layer can obtain satisfactory electron injection energy without significantly increasing the driving voltage force.

The second electrode 17 is provided on the organic layer 15. The second electrode 17 may be a cathode which is an electron injection electrode. The material used to form the second electrode 17 may include a metal, alloy, conductive compound or mixture thereof with a low work function. 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), etc., and can be a transparent electrode in the form of a thin film. In some embodiments, in order to manufacture top-emitting light-emitting diodes, the transparent electrode may include indium tin oxide (ITO) or indium zinc oxide (IZO).

Although the organic light emitting device of FIG. 1 is described above, the present invention is not limited to this.

When phosphorescent dopants are used in the light-emitting layer, the hole blocking layer can be formed between the electron transport layer and the light-emitting layer by vacuum deposition, spin coating, casting, Lanmul-Brugge (LB) deposition, or E- 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 by vacuum deposition or spin coating, although 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 different from the hole injection The 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, BCP represented by the following chemical formula can be used as a material for forming a hole blocking layer.

The thickness of the hole blocking layer may be from about 20Å to about 1,000Å, and in some embodiments, may be from about 30Å to about 300Å. When the thickness of the hole blocking layer is within this range, the hole blocking layer can have good hole blocking ability without significantly 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. Examples of substituted C ₁ -C ₆₀ alkyl groups are at least one hydrogen atom via a deuterium atom; -F; -Cl; -Br; -I; -CN; hydroxyl; -NO ₂ ; amino; formamidinyl; hydrazine; Hydrazone; carboxyl group or its salt; sulfonic acid group or its salt; phosphate group or its salt; tri(C ₆ -C ₆₀ aryl) silane group; C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₂ -C ₆₀ alkenyl and C ₂ -C ₆₀ alkynyl; at least one hydrogen atom is deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, formamidinyl C ₁ -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy, C ₂ -C ₆₀ substituted with at least one of sulfonyl group, hydrazone, hydrazone, carboxyl group or its salt, sulfonic acid group or its salt or phosphate group or its salt 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 deuterium atom, -F, -Cl, -Br, -I, -CN, hydroxyl, -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 ₆₀ alkyl, -F substituted with at least one of C ₁ -C ₆₀ alkyl, C ₃ -substituted with at least one of C ₁ -C ₆₀ alkoxy, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₆ -C ₆₀ aryl or C ₂ -C ₆₀ heteroaryl 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 ₁ -C ₆₀ alkyl substituted with at least one C ₆ -C ₆₀ arylthio group.

The unsubstituted C ₁ -C ₆₀ alkoxy group (or C ₁ -C ₆₀ alkoxy group) may be a group represented by the chemical formula -OA, where A is an unsubstituted C ₁ -C ₆₀ alkane group as described above base. Examples of unsubstituted C ₁ -C ₆₀ alkoxy groups are methoxy group and isopropyloxy group. At least one hydrogen atom in the alkoxy group may be substituted by the substituent described above in conjunction with the 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 an unsubstituted C ₂ -C ₆₀ alkyl group chain. Examples of alkenyl groups are ethenyl, propenyl, butenyl and the like. At least one hydrogen atom in the unsubstituted C ₂ -C ₆₀ alkenyl group may be substituted by the substituent described above in conjunction with the 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 reference bond at its center or terminal. Examples of the unsubstituted C ₂ -C ₆₀ alkynyl group (or C ₂ -C ₆₀ alkynyl group) to include ethynyl (ethynyl), an alkynyl group of at least one hydrogen atom propynyl (propynyl) group may be C ₁ binding -C ₆₀ alkyl and substituted by the substituent described above.

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, cyclopentyl, cyclohexyl, cyclooctyl . At least one hydrogen atom in the cycloalkyl group may be substituted by the substituent group described above in combination with the 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, cyclopentenyl, cylcopentenyl, cyclohexcenyl, cycloheptenyl (cycloheptenyl), 1,3-cyclohexadienyl group (1,3-cyclohexadienyl group), 1,4-cyclohexadienyl group (1,4-cyclohexadienyl group), 2,4-cycloheptadienyl ( 2,4-cycloheptadienyl group) and 1,5-cyclooctadieneyl (1,5-cyclooctadineyl group). At least one hydrogen atom in the cycloalkenyl group may be substituted by the substituent group described above in combination with the 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 including at least one aromatic ring. The unsubstituted C ₆ -C ₆₀ arylene group is a divalent group of a carbocyclic ring system having 6 to 60 carbon atoms including at least one aromatic ring. When the aryl group and the arylene group have at least two rings, they can be fused with each other through a single bond. Referring to the C ₁ -C ₆₀ alkyl group, at least one hydrogen atom in the aryl group and the aryl group may be substituted by the substituent described above in conjunction with the C ₁ -C ₆₀ alkyl group.

Examples of substituted or unsubstituted C ₆ -C ₆₀ aryl groups are phenyl, C ₁ -C ₁₀ alkylphenyl group (for example, ethylphenyl group), C ₁ -C ₁₀ alkyl Alkylbiphenyl group (eg, ethylbiphenyl group), halophenyl group (for example, o-, m- or p-fluorophenyl group) and dichloro Phenyl (dichlorophenyl group), dicyanophenyl (dicyanophenyl group), trifluoromethoxyphenyl (trifluoromethoxyphenyl group), o-, m- or p-tolyl group (tolyl group), o-, m- or p -Cumenyl group, 2,4,6-mesityl group, phenoxyphenyl group, (α,α-dimethylbenzene) phenyl ((α, α-dimethylbenzene)phenyl group), (N,N'-dimethyl)aminophenyl group ((N,N'-dimethyl)aminophenyl group), (N,N'-diphenyl)aminophenyl group ((N ,N'-diphenyl)aminophenyl group), Cyclopentadienyl, Indenyl, Naphthyl, Halonaphthyl group (for example, fluoronaphthyl group), C ₁ -C ₁₀ alkylnaphthalene Alkylnaphthyl group (for example, methylnaphthyl group), C ₁ -C ₁₀ alkoxynaphthyl group (for example, methoxynaphthyl group), anthracenyl, azulene Group, diheptatrienyl group, acenaphthylenyl group, acenaphthylenyl group, phenalenyl group, stilbene group, anthraquinolyl group, methylanthryl group, phenanthryl, tandem Benzene, pyrenyl, quinyl, ethyl-chrysenyl group, picenyl group, perylenyl group, chloroperylenyl group, pentaphenyl group , Fused pentaphenyl, tetraphenylenyl group, hexaphenyl group, hexaphenyl group, rubicenyl group, coronenyl group, trinaphthylenyl group , Heptaphenyl group (heptaphenyl group), heptatrienyl (heptalenyl group), pyranthrene (pyranthrenyl group) and zedoyl (ovalenyl group). Examples of substituted C ₆ -C ₆₀ aryl groups can be inferred based on the above-mentioned unsubstituted C ₆ -C ₆₀ aryl groups and substituted C ₁ -C ₆₀ alkyl groups. The substituted or unsubstituted C ₆ -C ₆₀ aryl group can be inferred based on 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 extended heteroaryl group is a divalent group having at least one aromatic ring including 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 can be fused to each other through a single bond. At least one hydrogen atom in the heteroaryl group and the heteroaryl group may be substituted by the substituent group described above in combination with the C ₁ -C ₆₀ alkyl group.

Examples of unsubstituted C ₂ -C ₆₀ heteroaryl groups are pyrazolyl, imidazolyl, oxazolyl, thiazolyl, triazolyl, tetrazolyl, oxadiazolyl, pyridyl, pyrazinyl, pyrimidine , Triazinyl, carbazolyl, indolyl, quinolinyl, isoquinolinyl, benzimidazolyl, imidazolidinyl, imidazolylpyrimidinyl, dibenzothienyl, dibenzofuranyl and morpholine 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 refers to -SA ₃ (wherein A ₃ is the above substituted or unsubstituted C ₆ -C ₆₀ aryl group).

Hereinafter, this embodiment will be described in detail by referring to the following synthesis examples and other examples. However, these examples are for illustrative purposes only and are not intended to limit the scope of this embodiment.

Examples 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 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, and then extracted three times with 50 mL of water and 50 mL of ether. The organic layer was collected and dried using magnesium sulfate to evaporate the solvent. The residue was separated and purified by silica gel column chromatography to obtain 7.33g (80% yield) 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) di Palladium[(tris(dibenzylidine acetone)dipalladium(0))]), 0.04g (0.4mmol) of tri-tert-butylphosphine (P(t-Bu) ₃ )) and 1.44g (15.0mmol) ) Of 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 ether. The organic layer was collected and dried using magnesium sulfate to evaporate the solvent. The residue was separated and purified by silica gel column chromatography to obtain 4.80 g (yield 78%) of Compound 1. This compound was verified using mass spectrometry/fast atom impact method (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

Except that Intermediate 4-3 was used instead of Intermediate 4-1, 4.98 g of Compound 3 was prepared in the same manner as the preparation method of Compound 1 of Synthesis Example 1 (80% yield). 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

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

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

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),7.65-7.52(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

Except that Intermediate 4-5 was used instead of Intermediate 4-1, 4.77 g of Compound 5 was prepared in the same manner as the preparation method of Compound 1 of Synthesis Example 1 (a yield of 70%). MS/FAB and ¹ H NMR were used to verify compound 5.

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

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

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

¹ H NMR (CDCl ₃ , 400 MHz) 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

Except for using Intermediate 4-7 instead of Intermediate 4-1, 4.82 g of Compound 7 was prepared in the same manner as the preparation method of Compound 1 of Synthesis Example 1 (yield 71%). 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

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

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

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

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

¹ H NMR (CDCl ₃ , 400 MHz) δ (ppm) 7.84-7.82 (m, 2H), 7.80 (d, 1H), 773-7.70 (m, 2H), 7.67 (d, 1H), 7.65 (d, 1H ), 7.62-7.58 (m, 2H), 754-7.52 (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

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

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

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 (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

Except for using Intermediate 4-17 instead of Intermediate 4-1, 4.94 g of Compound 17 was prepared in the same manner as the preparation method of Compound 1 of Synthesis Example 1 (yield 73%). 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

Except for using Intermediate 4-18 instead of Intermediate 4-1, 5.81 g of Compound 18 was prepared in the same manner as the preparation method of Compound 1 of Synthesis Example 1 (a yield of 70%). 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

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

C ₄₂ H ₂₄ F ₅ N: calculated value 637.18, and actual measurement 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

Except that Intermediate 4-20 was used instead of Intermediate 4-1, 4.54 g of Compound 20 was prepared in the same manner as the preparation method of Compound 1 of Synthesis Example 1 (yield 76%). 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 , 400 MHz) 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

Except for using Intermediate 4-21 instead of Intermediate 4-1, 3.44 g of Compound 21 was prepared in the same manner as the preparation method of Compound 1 of Synthesis Example 1 (yield 59%). 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

Except for using Intermediate 4-22 instead of Intermediate 4-1, 4.03 g of Compound 22 was prepared in the same manner as the preparation method of Compound 1 of Synthesis Example 1 (56% yield). 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

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

C ₅₆ H ₃₆ N ₄ : calculated value 764.29, and actual measurement 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

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

C ₄₇ H ₃₂ N ₂ : calculated value 624.26, and actual measurement 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

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

C ₄₇ H ₃₂ N ₂ : calculated value 624.26, and actual measurement 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

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

C ₄₇ H ₃₂ N ₂ : calculated value 624.26, and actual measurement 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

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

C ₄₈ H ₃₁ N ₃ : calculated value 649.25, and actual measurement 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

Except for using Intermediate 4-30 instead of Intermediate 4-1, 4.99 g of Compound 30 was prepared in the same manner as the preparation method of Compound 1 of Synthesis Example 1 (yield 74%). Compound 30 was verified using MS/FAB and ¹ H NMR.

C ₅₁ H ₃₄ N ₂ : calculated value 674.27, and actual 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), 7.87-7.80 (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

Except that Intermediate 4-31 was used instead of Intermediate 4-1, 4.98 g of Compound 31 was prepared in the same manner as the preparation method of Compound 1 of Synthesis Example 1 (80% yield). 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

Except for using intermediate 4-32 instead of intermediate 4-1, 5.40 g of compound 32 was prepared in the same manner as the preparation method of compound 1 of Synthesis Example 1 (yield 73%). 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

Except for using Intermediate 4-35 instead of Intermediate 4-1, 5.05 g of Compound 35 was prepared in the same manner as the method for preparing Compound 1 of Synthesis Example 1 (yield 67%). Compound 35 was verified using MS/FAB and ¹ H NMR.

C ₅₈ H ₃₈ N ₂ O: calculated value 778.30, and actual measurement 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

Except for using Intermediate 4-36 instead of Intermediate 4-1, 5.80 g of Compound 36 was prepared in the same manner as the preparation method of Compound 1 of Synthesis Example 1 (a yield of 70%). 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 , 400 MHz) 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

Except that Intermediate 4-38 was used instead of Intermediate 4-1, 5.04 g of Compound 38 was prepared in the same manner as the preparation method of Compound 1 of Synthesis Example 1 (yield: 75%). 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 , 400 MHz) 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

Except for using intermediate 2-42 instead of intermediate 2-1, intermediate 3-42 was prepared in the same manner as the preparation method of intermediate 3-1 of Synthesis Example 1.

Synthesis of Compound 42

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

C ₅₂ H ₃₃ N ₃ : calculated value 699.27, and actual measurement 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

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

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

¹ H NMR (CDCl ₃ , 400 MHz) 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

Except for using intermediate 2-45 instead of intermediate 2-1, intermediate 3-45 was prepared in the same manner as the preparation method of intermediate 3-1 of Synthesis Example 1.

Synthesis of Compound 45

Except for using Intermediate 3-45 and Intermediate 4-31 instead of Intermediate 3-1 and Intermediate 4-1, 5.38 g of compound was prepared in the same manner as the preparation method of Compound 1 of Synthesis Example 1 45 (80% yield). 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

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

C ₅₅ H ₃₆ N ₂ : calculated value 724.29, and 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

Except for using intermediate 2-51 instead of intermediate 2-1, intermediate 3-51 was prepared in the same manner as the preparation method of intermediate 3-1 of Synthesis Example 1.

Synthesis of Compound 51

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

C ₄₈ H ₃₁ N ₃ : calculated value 649.25, and actual measurement 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

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

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

¹ H NMR (CDCl ₃ , 400 MHz) 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

Except for using intermediate 2-57 instead of intermediate 2-1, intermediate 3-57 was prepared in the same manner as the preparation method of intermediate 3-1 of Synthesis Example 1.

Synthesis of Compound 57

Except for using Intermediate 3-57 and Intermediate 4-32 instead of Intermediate 3-1 and Intermediate 4-1, 4.97 g of compound was prepared in the same manner as the preparation method of Compound 1 of Synthesis Example 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 , 400 MHz) 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

Except for using intermediate 2-58 instead of intermediate 2-1, intermediate 3-58 was prepared in the same manner as the preparation method of intermediate 3-1 of Synthesis Example 1.

Synthesis of Compound 58

Except for using Intermediate 3-58 and Intermediate 4-25 instead of Intermediate 3-1 and Intermediate 4-1, 5.67 g of compound was prepared in the same manner as the preparation method of Compound 1 of Synthesis Example 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, and actual measurement 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

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

C ₅₃ H ₃₆ N ₂ : calculated value 700.29, and actual measurement 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

Except that Intermediate 4-27 was used instead of Intermediate 4-25, 5.08 g of Compound 60 was prepared in the same manner as in the preparation of Compound 58 of Synthesis Example 34 (yield 70%). 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

Except that Intermediate 4-32 was used instead of Intermediate 4-25, 6.04 g of Compound 61 was prepared in the same manner as the preparation method of Compound 58 of Synthesis Example 34 (yield 74%). 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 , 400 MHz) 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

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

C ₅₇ H ₃₈ N ₂ : calculated value 750.30, and actual measurement 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

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

C ₅₇ H ₃₈ N ₂ : calculated value 750.30, and actual measurement 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

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

C ₅₇ H ₃₈ N ₂ : calculated value 750.30, and actual measurement 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

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

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

¹ H NMR (CDCl ₃ , 400 MHz) 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

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

C ₅₅ H ₃₆ N ₂ : calculated value 724.29, and 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

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

C ₅₃ H ₃₄ N ₂ : calculated value 698.27, and actual measurement 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

Except for using Intermediate 4-70 instead of Intermediate 4-25, 3.56 g of Compound 70 was prepared in the same manner as in the preparation of Compound 58 of Synthesis Example 34 (yield 53%). 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 , 400 MHz) 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

Except that Intermediate 4-43 was used instead of Intermediate 4-25, 4.97 g of Compound 73 (65% yield) was prepared in the same manner as in the preparation of Compound 58 of Synthesis Example 34. 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

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

C ₅₉ H ₄₀ N ₂ : calculated value 776.32, and actual measurement 776.32

¹ H NMR (CDCl ₃ , 400 MHz) 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

Except that Intermediate 4-77 was used instead of Intermediate 4-25, 5.22 g of Compound 77 was prepared in the same manner as in the preparation of Compound 58 of Synthesis Example 34 (yield 72%). 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 ,400MHz)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

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

C ₅₇ H ₃₈ N ₂ : calculated value 750.30, and actual measurement 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

Except for using intermediate 4-79 instead of intermediate 4-25, 5.00 g of compound 79 was prepared in the same manner as the preparation method of compound 58 of Synthesis Example 34 (yield 69%). 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

Except for using intermediate 2-82 instead of intermediate 2-1, intermediate 3-82 was prepared in the same manner as the preparation method of intermediate 3-1 of Synthesis Example 1.

Synthesis of Compound 82

Except for using intermediate 3-82 and intermediate 4-25 instead of intermediate 3-1 and intermediate 4-1, a compound of 5.20 g was prepared in the same manner as the preparation method of compound 1 of Synthesis Example 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 actual measurement 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

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

C ₆₃ H ₄₂ N ₂ : calculated value 826.33, and actual measurement 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

Except for using intermediate 2-84 instead of intermediate 2-1, intermediate 3-84 was prepared in the same manner as the preparation method of intermediate 3-1 of Synthesis Example 1.

Synthesis of Compound 84

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

C ₆₀ H ₄₂ N ₂ : calculated value 790.33, and actual measurement 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

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

C ₅₇ H ₃₉ N ₃ : calculated value 765.31, and actual measurement 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), 7.85-7.80 (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

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

C ₅₆ H ₃₈ N ₂ : calculated value 738.30, and actual measurement 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

Except for using intermediate 2-89 instead of intermediate 2-1, intermediate 3-89 was prepared in the same manner as the preparation method of intermediate 3-1 of Synthesis Example 1.

Synthesis of Compound 89

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

C ₅₇ H ₃₆ N ₂ : calculated value 748.29, and actual measurement 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

Except for using intermediate 2-92 instead of intermediate 2-1, intermediate 3-92 was prepared in the same manner as the preparation method of intermediate 3-1 of Synthesis Example 1.

Synthesis of Compound 92

Except that Intermediate 3-92 and Intermediate 4-27 were used instead of Intermediate 3-1 and Intermediate 4-1, 4.61 g of compound was prepared in the same manner as the preparation method of Compound 1 of Synthesis Example 1 92 (61% yield). 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 , 400 MHz) 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

Except for using intermediate 2-95 instead of intermediate 2-1, intermediate 3-95 was prepared in the same manner as the preparation method of intermediate 3-1 of Synthesis Example 1.

Synthesis of Compound 95

Except for using Intermediate 3-95 and Intermediate 4-30 instead of Intermediate 3-1 and Intermediate 4-1, a compound of 4.74 g was prepared in the same manner as the preparation method of Compound 1 of Synthesis Example 1 95 (62% yield). Compound 95 was verified using MS/FAB and ¹ H NMR.

C ₅₇ H ₃₆ N ₂ O: calculated value 764.28, and actual measurement 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

Except for using intermediate 2-97 instead of intermediate 2-1, intermediate 3-97 was prepared in the same manner as the preparation method of intermediate 3-1 of Synthesis Example 1.

Synthesis of Compound 97

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

C ₆₁ H ₃₉ N ₃ : calculated value 813.31, 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

Except that Intermediate 4-31 was used instead of Intermediate 4-4, 4.65 g of Compound 98 was prepared in the same manner as in the preparation of Compound 97 of Synthesis Example 58 (yield 59%). 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

Except for using intermediate 2-98 instead of intermediate 2-1, intermediate 3-99 was prepared in the same manner as the preparation method of intermediate 3-1 of Synthesis Example 1.

Synthesis of Compound 99

Except for using Intermediate 3-99 and Intermediate 4-30 instead of Intermediate 3-1 and Intermediate 4-1, 5.03 g of the compound was prepared in the same manner as the preparation method of Compound 1 of Synthesis Example 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

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

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

¹ H NMR (CDCl ₃ , 400 MHz) 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

Except that Intermediate B38 was used instead of Intermediate 4-1, 5.23 g of Compound 104 was prepared in the same manner as the preparation method of Compound 1 of Synthesis Example 1 (72% yield). 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 , 400 MHz) 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

Except that Intermediate 3-58 and Intermediate B37 were used instead of Intermediate 3-1 and Intermediate 4-1, 6.21 g of Compound 107 was prepared in the same manner as in the preparation of Compound 1 of Synthesis Example 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 , 400 MHz) 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)

Example 1

To manufacture the anode, the Corning 15Ω/cm ² (1200Å) ITO glass substrate was cut to a size of 50mm x 50mm x 0.7mm, followed by ultrasonic waves in isopropyl alcohol and pure water for 5 minutes, and ultraviolet irradiation for 30 minutes and Exposure to ozone. The resulting glass substrate was placed in a vacuum deposition diode.

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

Next, 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)) at a weight ratio of 98:2 Co-deposited on the hole transport layer to form a light-emitting layer with a thickness of about 300Å.

Next, Compound 1 is deposited on the light emitting layer to form an electron transport layer having a thickness of about 300Å, and then LiF is deposited on the electron transport layer to form an electron injection layer having a thickness of about 10Å. Then, Al is deposited on the electron injection layer to form a second electrode (cathode) having a thickness of about 3,000Å, thereby completing the manufacture 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 Compound 4 was used instead of Compound 1 to form the electron transport layer.

Example 3

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

Example 4

An organic light-emitting diode manufactured in the same manner as in Example 1 except that Compound 23 was used instead of Compound 1 to form the electron transport layer.

Example 5

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

Example 6

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

Example 7

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

Example 8

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

Example 9

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

Example 10

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

Example 11

An organic light-emitting diode manufactured in the same manner as in Example 1 except that Compound 58 was used instead of Compound 1 to form the electron transport layer.

Example 12

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

Example 13

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

Example 14

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

Example 15

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

Example 16

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

Example 17

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

Example 18

An organic light-emitting diode manufactured in the same manner as in Example 1 except that Compound 86 was used instead of Compound 1 to form the electron transport layer.

Example 19

An organic light-emitting diode manufactured in the same manner as in Example 1 except that Compound 97 was used instead of Compound 1 to form the electron transport layer.

Example 20

An organic light-emitting diode manufactured in the same manner as in Example 1 except that Compound 25 was used instead of DPAVBi to form the light-emitting layer, and Alq ₃ instead of Compound 1 was used to form the electron transport layer.

Example 21

An organic light-emitting diode manufactured in the same manner as in Example 1 except that Compound 86 was used instead of DPAVBi to form the light-emitting layer, and Alq ₃ instead of Compound 1 was used to form the electron transport layer.

Example 22

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

Example 23

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

Example 24

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

Comparative example 1

An organic light emitting diode manufactured in the same manner as in Example 1 except that Alq _{3 was used} instead of Compound 1 to form the electron transport layer.

Comparative example 2

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

Synthesis of Intermediate 3-A

Except for using intermediate 1-A instead of intermediate 1-1, intermediate 3-A was prepared in the same manner as the preparation method of intermediate 3-1 of Synthesis Example 1.

Synthesis of Compound A

Except for using 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, the The preparation method prepared 3.23 g of compound A in the same way (yield 63%).

Manufacture of organic light-emitting diodes

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

Comparative Example 3

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

Synthesis of Compound B

Except for using intermediate 4-B instead of intermediate 4-A, compound B was prepared in the same manner as the method for preparing compound A of Comparative Example 2.

Manufacture of organic light-emitting diodes

In addition to using Compound B instead of Compound 1 to form the electron transport layer, and Example 1 An organic light-emitting diode manufactured in the same manner.

Comparative Example 4

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

Synthesis of Compound C

Except for using intermediate 4-C instead of intermediate 4-A, compound C was prepared in the same manner as the method for preparing compound A of Comparative Example 2.

Manufacture of organic light-emitting diodes

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

Comparative example 5

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

Synthesis of Compound D

Except for using intermediate 4-D instead of intermediate 4-A, compound D was prepared in the same manner as the method for preparing compound A of Comparative Example 2.

Manufacture of organic light-emitting diodes

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

Evaluation Example 1

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

Referring to Table 1, it is found that the organic light-emitting diodes of Examples 1 to 19 and Examples 22 to 24 have lower driving voltage and higher brightness compared to the organic light-emitting diodes of Comparative Examples 1 to 5. , Higher efficiency and better service life characteristics. It is found that the organic light-emitting diodes of Examples 20 to 21 have a lower driving voltage and better lifespan than the organic light-emitting diodes of Comparative Example 1.

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

Although this embodiment has been specifically shown and described by reference to its exemplary embodiments, it will be understood by those skilled in the art that the various forms and details of the changes it has made have not deviated from the definition of the scope of the accompanying patent application The scope and spirit of this embodiment.

10‧‧‧ organic light emitting diode

11‧‧‧ substrate

13‧‧‧First electrode

15‧‧‧ Organic layer

17‧‧‧Second electrode

Claims (15)

An amine compound represented by the following chemical formula 1:

Wherein in Chemical Formula 1, Ar ₁ and Ar _{2 are} each independently substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or substituted or unsubstituted stilbene, and substituted benzene At least one substituent of the group, the substituted naphthyl group or the substituted fluorenyl group is methyl or phenyl; X ₁ is phenylene, naphthyl, carbazolyl, or dimethylstilbene; and m is An integer from 1 to 3; wherein at least one of Ar ₁ and Ar ₂ is substituted with at least one electron-withdrawing group; wherein the electron-withdrawing group is selected from -F; -CN; pyridyl; and substituted with phenyl Benzimidazolyl. An amine compound represented by the following chemical formula 1: Chemical formula 1

Wherein in Chemical Formula 1, Ar ₁ and Ar _{2 are} each independently phenylene substituted with -CN; X ₁ is phenylene; and m is an integer of 1 to 5. The amine compound as described in item 2 of the patent application scope, wherein the amine compound is the following compound 70:

The amine compound as described in item 2 of the patent application, wherein m is 1, 2 or 3. An amine compound, wherein the amine compound is one of the following compound 1 to compound 69, compound 71 to compound 73, and compound 75 to compound 109:

An organic light emitting diode includes 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 includes at least one An amine compound as described in any one of claims 1 to 5 in the patent application scope. The organic light emitting diode as described in item 6 of the patent application scope, wherein the organic layer includes a hole injection layer, a hole transmission layer, a functional layer having both hole injection and hole transmission capabilities, and a buffer At least one of a layer, an electron blocking layer, a light emitting layer, a hole blocking layer, 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 as described in item 7 of the patent application range, wherein the organic layer includes the electron transport layer, and the amine compound is included in the electron transport layer. The organic light emitting diode as described in item 8 of the patent application range, wherein the electron transport layer further includes a metal complex. The organic light-emitting diode as described in item 9 of the patent application scope, wherein the metal complex is 8-hydroxyquinoline lithium. The organic light-emitting diode as described in item 10 of the patent application range, wherein the organic layer includes the light-emitting layer, and the amine-based compound is included in the light-emitting layer. The organic light-emitting diode as described in item 11 of the patent application range, wherein the amine compound in the light-emitting layer is used as a matrix, and the light-emitting layer further includes a blue fluorescent dopant. The organic light-emitting diode as described in item 11 of the patent application range, wherein the amine compound in the light-emitting layer is used as a dopant, and the light-emitting layer further includes an allium compound represented by the following chemical formula 400 and the following chemical formula 401 represents at least one of allium compounds:

Among them, in Chemical Formula 400 and Chemical Formula 401, Ar ₁₁₁ and Ar _{112 are} each independently substituted or unsubstituted C ₆ -C ₆₀ arylene groups; Ar ₁₁₃ to Ar ₁₁₆ and Ar ₁₂₂ to Ar _{125 are} each independently Substituted or unsubstituted C ₁ -C ₁₀ alkyl or substituted or unsubstituted C ₆ -C ₆₀ aryl; Ar ₁₂₆ and Ar _{127 are} each independently C ₁ -C ₁₀ alkyl; and g, h , I, j, k and 1 are independently integers from 0 to 4. The organic light-emitting diode as described in item 13 of the patent application, wherein Ar ₁₁₁ and Ar _{112 are} each independently phenylene, naphthyl, phenanthrenyl or pyrenyl; or via phenyl, naphthyl and Phenylene, naphthyl, phenanthrenyl, fluorenyl or pyrenyl substituted with at least one of anthracenyl; Ar ₁₁₃ to Ar ₁₁₆ and Ar ₁₂₂ to Ar _{125 are} each independently phenyl, naphthyl C ₁ -C ₁₀ alkyl substituted with at least one of anthracenyl; phenyl; naphthyl; anthracenyl; pyrenyl; phenanthrenyl; fluorenyl; deuterium atom, halogen atom, hydroxyl group, cyano group, -NO ₂ , Amino, carboxamidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C _2- C ₆₀ alkynyl, C ₁ -C ₆₀ alkoxy, phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl and fluorenyl substituted phenyl, naphthyl, anthracenyl, pyrenyl, Fiki and Fuji; 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 as described in item 7 of the patent application range, wherein the organic layer includes at least one of the hole injection layer, the hole transmission layer, and the functional layer having both hole injection and hole transmission capabilities One, and at least one of the hole injection layer, the hole transmission layer, and the functional layer having both hole injection and hole transmission capabilities includes a p-doped material.

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