KR101511169B1 - Amine-based compound and organic light emitting diode comprising the same - Google Patents

Abstract

An amine compound and an organic light emitting device containing the same are disclosed.

Description

Amine-based compounds and organic light-emitting devices containing the same

A compound for an organic light emitting device, and an organic light emitting device.

The organic light emitting diode is a self light emitting type device having a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed characteristics, and multi-coloring.

A typical organic light emitting device may have a structure in which an anode is formed on a substrate, and a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially formed on the anode. Here, the hole transporting layer, the light emitting layer, and the electron transporting layer are organic thin films made of organic compounds.

The driving principle of the organic light emitting device having the above-described 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 via the hole transporting layer, and electrons injected from the cathode move to the light emitting layer via the electron transporting layer. The carriers such as holes and electrons recombine in the light emitting layer region to generate an exiton. This exciton changes from the excited state to the ground state and light is generated.

An amine compound having a novel structure and an organic light emitting device containing the same are provided.

According to one aspect, there is provided an amine-based compound represented by the following Formula 1:

≪ Formula 1 >

In Formula 1,

Ar ₁ and Ar ₂ are, independently of each other, a substituted or unsubstituted C ₆ -C ₆₀ aryl group or a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group;

X ₁ is a substituted or unsubstituted C ₆ -C ₆₀ arylene group or a substituted or unsubstituted C ₂ -C ₆₀ heteroarylene group;

m is an integer from 1 to 5;

At least one substituent of the substituted C ₆ -C ₆₀ aryl group, the substituted C ₂ -C ₆₀ heteroaryl group, the substituted C ₆ -C ₆₀ arylene group and the substituted C ₂ -C ₆₀ heteroarylene group may be substituted with at least one substituent selected from the group consisting of deuterium ; -F; -Cl; -Br; -I; -CN; A hydroxyl group; -NO ₂ ; An amino group; An amidino group; Hydrazine; Hydrazone; A carboxyl group or a salt thereof; Sulfonic acid group or its salt; Phosphoric acid or its salts; Tree (C ₆ -C ₆₀ aryl) silyl group; A C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₂ -C ₆₀ alkenyl group and a C ₂ -C ₆₀ alkynyl group; Wherein R _{1 is selected} from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, amidino, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₂ -C ₆₀ alkenyl group and a C ₂ -C ₆₀ alkynyl group; A C ₃ -C ₆₀ cycloalkyl group, a C ₃ -C ₆₀ cycloalkenyl group, a C ₆ -C ₆₀ aryl group, a C ₂ -C ₆₀ heteroaryl group, a C ₆ -C ₆₀ aralkyl group, a C ₆ -C ₆₀ aryloxy group And a C ₆ -C ₆₀ arylthio group; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, salts, C ₁ -C ₆₀ alkyl group, substituted with at least one C ₁ -C ₆₀ alkyl group F, C ₁ -C ₆₀ alkoxy group, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₆ - C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group substituted by one or more of C ₃ -C ₆₀ cycloalkyl, C ₃ -C ₆₀ cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₂ -C ₆₀ hetero aryl group, C ₆ -C ₆₀ aralkyl, C ₆ -C ₆₀ aryloxy and C ₆ -C ₆₀ aryl come Im; Be one of them,

At least one of Ar < _{1 >} and Ar < ₂ >-CN; -NO ₂ ; A C ₁ -C ₆₀ alkyl group substituted by at least one -F; A C ₂ -C ₆₀ heteroaryl group; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, salts, C ₁ -C ₆₀ alkyl group, substituted with at least one C ₁ -C ₆₀ alkyl group F, C ₁ -C ₆₀ alkoxy group, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₆ - C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group, at least one substituted C ₂ -C ₆₀ heteroaryl group of; a C ₆ -C ₆₀ substituted with at least one electron receptor (electron withdrawing group) selected from the group consisting of Lt; / RTI >

According to another aspect, there is provided a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer contains at least one amine compound.

The organic light emitting device including the amine compound may have low driving voltage, high luminance, high efficiency, and long life.

1 is a schematic view showing the structure of an organic light emitting device according to an embodiment.

The amine compound is represented by the following formula (1): < EMI ID =

≪ Formula 1 >

Wherein Ar ₁ and Ar ₂ are 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 a C ₆ -C ₆₀ aryl group or a substituted or unsubstituted C ₂ -C ₆₀ hetero arylene group.

At least one substituent of the substituted C ₆ -C ₆₀ aryl group, the substituted C ₂ -C ₆₀ heteroaryl group, the substituted C ₆ -C ₆₀ arylene group and the substituted C ₂ -C ₆₀ heteroarylene group may be substituted with at least one substituent selected from the group consisting of deuterium ; -F; -Cl; -Br; -I; -CN; A hydroxyl group; -NO ₂ ; An amino group; An amidino group; Hydrazine; Hydrazone; A carboxyl group or a salt thereof; Sulfonic acid group or its salt; Phosphoric acid or its salts; Tree (C ₆ -C ₆₀ aryl) silyl group; A C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₂ -C ₆₀ alkenyl group and a C ₂ -C ₆₀ alkynyl group; Wherein R _{1 is selected} from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, amidino, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₂ -C ₆₀ alkenyl group and a C ₂ -C ₆₀ alkynyl group; A C ₃ -C ₆₀ cycloalkyl group, a C ₃ -C ₆₀ cycloalkenyl group, a C ₆ -C ₆₀ aryl group, a C ₂ -C ₆₀ heteroaryl group, a C ₆ -C ₆₀ aralkyl group, a C ₆ -C ₆₀ aryloxy group And a C ₆ -C ₆₀ arylthio group; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, salts, C ₁ -C ₆₀ alkyl group, substituted with at least one C ₁ -C ₆₀ alkyl group F, C ₁ -C ₆₀ alkoxy group, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₆ - C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group substituted by one or more of C ₃ -C ₆₀ cycloalkyl, C ₃ -C ₆₀ cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₂ -C ₆₀ hetero aryl group, C ₆ -C ₆₀ aralkyl, C ₆ -C ₆₀ aryloxy and C ₆ -C ₆₀ aryl come Im; ≪ / RTI >

In Formula 1, at least one of Ar ₁ and Ar ₂ represents -F; -CN; -NO ₂ ; A C ₁ -C ₆₀ alkyl group substituted by at least one -F; A C ₂ -C ₆₀ heteroaryl group; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, salts, C ₁ -C ₆₀ alkyl group, substituted with at least one C ₁ -C ₆₀ alkyl group F, C ₁ -C ₆₀ alkoxy group, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₆ - C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group, at least one substituted C ₂ -C ₆₀ heteroaryl group of; a C ₆ -C ₆₀ substituted with at least one electron receptor (electron withdrawing group) selected from the group consisting of Lt; / RTI >

For example, the at least one electron acceptor may be -F; -CN; -NO ₂ ; A C ₁ -C ₂₀ alkyl group substituted by at least one -F; A C ₂ -C ₂₀ heteroaryl group containing N as a ring-forming atom; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, salts, C ₁ -C ₂₀ alkyl group, at least one F a C ₁ -C ₂₀ alkyl group substituted by a, C ₁ -C ₂₀ alkoxy group, C ₆ -C ₂₀ aryl group and C ₂ -C ₂₀ heteroaryl group, one or more of And a C ₂ -C ₂₀ heteroaryl group, which is substituted by a ring-forming atom and contains N, may be selected from the group consisting of:

According to one embodiment, the at least one electron acceptor of Formula 1 is selected from the group consisting of -F; -CN; A C ₁ -C ₂₀ alkyl group substituted by at least one -F; Pyrrolyl, pyrazolyl, imidazolyl, imidazolinyl, imidazopyridinyl, imidazopyrimidinyl, pyridinyl, imidazopyrimidinyl, imidazopyrimidinyl, , Pyrazinyl, pyrimidinyl, benzoimidazoly, indolyl, purinyl, quinolinyl, isoquinolinyl, phthalazinyl (such as pyridyl, pyrimidinyl, The present invention relates to a method for preparing a compound of formula (I), wherein the compound is selected from the group consisting of phthalazinyl, indolizinyl, quinazolinyl, cinnolinyl, indazolyl, carbazolyl, phenazinyl, phenanthridinyl, Triazinyl, pyridazinyl, triazolyl, and tetrazolyl; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, Pyridyl, imidazolyl, imidazolidinyl, imidazopyrimidinyl, imidazopyrimidinyl, pyridinyl, pyrazinyl, pyrimidyl, pyrimidinyl, pyrimidinyl, pyrimidinyl, pyrimidinyl, Wherein R is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, benzoimidazolyl, indolyl, purinyl, quinolinyl, isoquinolinyl, phthalazinyl, indolizinyl, quinazolinyl, cinnolinyl, indazolyl, , Triazinyl, pyridazinyl, triazolyl, and tetrazolyl.

Specifically, in Formula 1, the at least one electron acceptor may be selected from the group consisting of -F; -CN; A C ₁ -C ₂₀ alkyl group substituted by at least one -F; Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl and benzoimidazolyl groups; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzoimidazolyl, and carbazolyl groups substituted with at least one of a nitrogen, a triazinyl, and a carbazolyl group; , But is not limited thereto.

According to another embodiment, at least one of the electron acceptors of Formula 1 is -F; -CN; -CH ₂ F; -CHF _2; -CF _3; And the following chemical formulas (2) (1) to (14):

Z ₁₁ to Z ₁₈ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, -CN, a hydroxyl group, -NO ₂ , an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkyl group substituted with at least one of F, C ₁ - A C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, a pyridinyl group, a triazinyl group or a carbazolyl group.

For example, in the above formulas (2) to (14), Z ₁₁ to Z ₁₈ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, -CN, -NO _2, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a methoxy group, an ethoxy group, Pro A phenoxy group, a phenoxy group, a phenoxy group, a phenoxy group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, a pyridinyl group, a triazinyl group or a carbazolyl group.

At least one of Ar ₁ and Ar ₂ in Formula 1 may be a C ₆ -C ₆₀ aryl group substituted with two or more electron acceptors.

For example, at least one of Ar ₁ and Ar ₂ may be a substituted or unsubstituted phenyl group, substituted biphenyl group, substituted naphthyl group, substituted anthryl group, substituted phenanthrenyl group, substituted pyrene Wherein the electron acceptor is selected from the group consisting of pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzoimidazolyl and carbazolyl groups; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, phthalazinyl, triazinyl, benzoimidazolyl, and pyridinyl substituted with at least one of halogen, A carbazolyl group; and a carbazolyl group.

At least one of Ar ₁ and Ar ₂ in the amine compound of Formula 1 is a C ₆ -C ₆₀ aryl group substituted by at least one electron withdrawing group as described above, Can be represented by the formula (1) or (2):

&Lt; Chemical Formula 1 (1) > < Chemical Formula 1 (2)

In the formula (1), Ar ₂ is a substituted or unsubstituted C ₆ -C ₂₀ aryl group or a substituted or unsubstituted C ₂ -C ₂₀ heteroaryl group, and Ar ₂ in the formula (1) Bar); In Formulas (1) and (2), A ring and B ring are substituted C ₆ -C ₂₀ aryl groups; R ₁ and R ₂ are, independently of one another, -F; -CN; -NO ₂ ; A C ₁ -C ₆₀ alkyl group substituted by at least one -F; A C ₂ -C ₆₀ heteroaryl group; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, salts, C ₁ -C ₆₀ alkyl group, substituted with at least one C ₁ -C ₆₀ alkyl group F, C ₁ -C ₆₀ alkoxy group, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₆ - C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl groups substituted with at least one of C ₂ -C ₆₀ heteroaryl group; e receptor (electron withdrawing group) selected from the group consisting of a; p and q are, independently of each other, an integer of 1 to 9;

For details of the electron acceptor in the above formulas (1) and (2), see above.

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

Alternatively, the amine compound may be represented by the formula 1 (2), and at least one of p R ₁ and q R ₂ in Formula 1 (2) may be -CN.

According to one embodiment, the amine compound is represented by the formula (1), and the ring A in the formula (1) is a substituted phenyl group, a substituted biphenyl group, a substituted naphthyl group, A substituted phenanthrenyl group, a substituted pyrenyl group, or a substituted fluorenyl group, but is not limited thereto.

According to another embodiment, the amine compound is represented by the formula (2), and the A ring and the B ring in the formula (1) are independently selected from the group consisting of a substituted phenyl group, a substituted biphenyl group, A substituted naphthyl group, a substituted anthryl group, a substituted phenanthrenyl group, a substituted pyrenyl group or a substituted fluorenyl group.

According to another embodiment, the amine compound is represented by the formula (1), wherein the ring A is a substituted phenyl group, a substituted biphenyl group, a substituted naphthyl group, a substituted anthryl group, a substituted phenan A thienyl group, a substituted pyrenyl group or a substituted fluorenyl group, and R ₁ is pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, Carbazolyl group; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, phthalazinyl, triazinyl, benzoimidazolyl, and pyridinyl substituted with at least one of halogen, Carbazolyl group; and p is 2, 3 or 4 (e.g., p is 2).

According to another embodiment, the amine compound is represented by the above formula (2), and the A ring and the B ring are, independently of each other, a substituted phenyl group, a substituted biphenyl group, a substituted naphthyl group, R ₁ and R ₂ are, independently of each other, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, substituted pyrazinyl, substituted pyrazinyl, , Quinazolinyl, triazinyl, benzimidazolyl, and carbazolyl groups; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, phthalazinyl, triazinyl, benzoimidazolyl, and pyridinyl substituted with at least one of halogen, And p and q independently of one another are 2, 3 or 4 (for example, p and q are 2), or an amine compound.

In Formula 1, at least one of Ar ₁ and Ar ₂ may be a phenyl group, a biphenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pentaerythrityl group, or a pentaerythrityl group substituted with at least one electron withdrawing group as described above Lt; / RTI &gt; or a fluorenyl group.

In the above formula (1), Ar ₁ and Ar ₂ independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pentalenyl group, a substituted or unsubstituted Indenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted azulenyl, substituted or unsubstituted heptalenyl, substituted or unsubstituted indacenyl group (substituted or unsubstituted indanyl group, indacenyl, substituted or unsubstituted acenaphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenalenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted phenanthrenyl, Substituted or unsubstituted anthryl groups, substituted or unsubstituted fluoranthenyl groups, substituted or unsubstituted triphenylenyl groups, substituted or unsubstituted pyrenyl groups, , A substituted or unsubstituted chlorenyl group ( substituted naphthacenyl, substituted or unsubstituted picenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted pentaphenyl, substituted or unsubstituted naphthacenyl, substituted or unsubstituted naphthacenyl, substituted or unsubstituted naphthacenyl, Substituted or unsubstituted hexacenyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, A substituted or unsubstituted imidazopyridinyl group, a substituted or unsubstituted imidazopyrimidinyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted imidazopyrimidinyl group, A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted pyrazinyl group, Purinyl, Or an unsubstituted quinolinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted indolizinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted naphthyridinyl group, A substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted cinnolinyl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted quinazolinyl group, A substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted pyranyl group, a substituted or unsubstituted chromenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted thienyl group, A substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted isothiazolyl group, ), Substitution Substituted or unsubstituted benzoimidazolyl, substituted or unsubstituted isoxazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzofuranyl, Substituted or unsubstituted triazinyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted tetrazolyl or substituted or unsubstituted thiazolyl, Substituted or unsubstituted phenanthrolinyl, wherein at least one of Ar ₁ and Ar ₂ is a phenyl group substituted with at least one electron acceptor as described above, a biphenyl group, a naphthyl group, an anthryl group, a phenanthrene group, A pyrenyl group, or a fluorenyl group.

For example, Ar ₁ and Ar ₂ in the above formula (1) independently of one another are a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthrenyl group , A substituted or unsubstituted anthryl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted pyridinyl group, Substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted thiazinyl, substituted or unsubstituted dibenzothiophenyl group, An unsubstituted dibenzofuranyl group or a substituted or unsubstituted phenanthrolinyl group; At least one of Ar &lt; _{1 &gt;} and Ar &lt; ₂ &gt;-CN; A C ₁ -C ₂₀ alkyl group substituted by at least one -F; Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl and carbazolyl groups; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzoimidazolyl, and carbazolyl groups substituted with at least one of a nitrogen, a triazinyl, and a carbazolyl group; A biphenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group or a fluorenyl group substituted with at least one electron acceptor selected from the group consisting of

In Formula 1, Ar ₁ and Ar ₂ may be connected to each other through a single bond.

According to one embodiment, the amine-based compound may be represented by any one of the following formulas (A) to (1J):

&Lt; Formula 1A >

&Lt; Formula 1C > < Formula 1D >

&Lt; Formula 1E > < EMI ID =

&Lt; Formula 1G > <

&Lt; Formula 1I > < EMI ID =

In the above formulas 1A to 1I, Ar ₂ is described above.

Formula 1A and 1B of R ₁₁ to R ₁₅ of the at least one, the formula 1C and 1D of the R ₁₁ to R _17, at least one, formula 1E and 1J of R ₁₁ to R ₁₈ and at least one formula 1F to 1I of R ₁₁ to one of the At least one of R &lt; ₁₉ &gt; is -F; -CN; -NO ₂ ; A C ₁ -C ₆₀ alkyl group substituted by at least one -F; A C ₂ -C ₆₀ heteroaryl group; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, salts, C ₁ -C ₆₀ alkyl group, substituted with at least one C ₁ -C ₆₀ alkyl group F, C ₁ -C ₆₀ alkoxy group, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₆ - It may be an electron receptor (electron withdrawing group) selected from the group consisting of; C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group, at least one of the groups substituted C ₂ -C ₆₀ heteroaryl group.

For example, at least one of R ₁₁ to R ₁₅ in the above formulas (IA) and (IB), at least one of R ₁₁ to R ₁₇ in the formulas (1C) and (1D), at least one of R ₁₁ to R ₁₈ in the formulas At least one of R &lt; ₁₁ &gt; to R &lt; ₁₉ &gt; -CN; A C ₁ -C ₂₀ alkyl group substituted by at least one -F; Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl and carbazolyl groups; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, phthalazinyl, triazinyl, benzoimidazolyl, and pyridinyl substituted with at least one of halogen, Carbazolyl group; and the like, but is not limited thereto.

According to another embodiment, Ar &lt; ₂ &gt; -CN; A C ₁ -C ₂₀ alkyl group substituted by at least one -F; Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl and carbazolyl groups; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, phthalazinyl, triazinyl, benzoimidazolyl, and pyridinyl substituted with at least one of halogen, A naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, or a fluorenyl group substituted with at least one electron acceptor selected from the group consisting of a carbazolyl group and a carbazolyl group.

According to one embodiment, the amine-based compound may be represented by the following general formula (1A-1) or 1A- (2)

&Lt; Formula 1A- (1) > < Formula 1A- (2) >

Wherein R ₁₂ , R ₁₄ , R ₂₂ and R ₂₄ independently of one another are pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, Quinazolinyl, triazinyl, benzimidazolyl, and carbazolyl groups; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, phthalazinyl, triazinyl, benzoimidazolyl, and pyridinyl substituted with at least one of halogen, A carbazolyl group; an electron acceptor selected from the group consisting of Ar ₂ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pie Or a substituted or unsubstituted fluorenyl group.

For example, in the above formulas (1A) and (1A), R ₁₂ , R ₁₄ , R ₂₂ and R ₂₄ independently represent -F; -CN; -CH ₂ F; -CHF _2; -CF _3; And (2) (2) to (14) above.

According to another embodiment, R ₁₂ , R ₁₄ , R ₂₂ and R ₂₄ in the general formulas (1A-1) and (1A-2) It can be one.

According to another embodiment, R ₁₂ , R ₁₄ , R ₂₂ and R ₂₄ in the above formulas (1A-1) and 1A-2 (2) independently of one another may be the formula (2) It is not.

In the above formula (1A), Ar ₂ may be a phenyl group, a biphenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group or a fluorenyl group, but is not limited thereto.

In Formula 1, X ₁ represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted pentalenylene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted naphthyl group Naphthylene, substituted or unsubstituted azulenylene, substituted or unsubstituted heptalenylene, substituted or unsubstituted indacenylene, substituted or unsubstituted acenaphthyl A substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted anthryl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted anthryl group, Anthrylene, a substituted or unsubstituted fluoranthenylene, a substituted or unsubstituted triphenylenylene, a substituted or unsubstituted pyrenylene, a substituted or unsubstituted chrysenyl A substituted or unsubstituted naphthacenylene, a substituted or unsubstituted picenylene, a substituted or unsubstituted perylenylene, a substituted or unsubstituted pentaphenylene group, a substituted or unsubstituted naphthacenylene group, a substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted pyrazolylene group, imidazolylene, a substituted or unsubstituted imidazolinylene group, a substituted or unsubstituted imidazopyridinylene group, a substituted or unsubstituted imidazopyrimidinylene group, a substituted or unsubstituted imidazopyrimidinylene group, A substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted indolylene group, a substituted or unsubstituted indolylene group, Substituted or unsubstituted quinolinylene, substituted or unsubstituted phthalazinylene, substituted or unsubstituted indolizinylene, substituted or unsubstituted indolizinylene, A substituted or unsubstituted naphthyridinylene group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted cinnolinylene group, a substituted or unsubstituted indazolylene group, a substituted or unsubstituted indazolylene group, Substituted or unsubstituted carbazolylene, substituted or unsubstituted phenazinylene, substituted or unsubstituted phenanthridinylene, substituted or unsubstituted pyranylene, substituted or unsubstituted pyrazole, , A substituted or unsubstituted chromenylene, a substituted or unsubstituted furanylene group, a substituted or unsubstituted benzofuranylene group, a substituted or unsubstituted thiophenylene group, a substituted or unsubstituted thiophenylene group, Or an unsubstituted benzothiophenylene group, a substituted or unsubstituted isothiazolylene group, a substituted or unsubstituted benzoimidazolylene group, a substituted or unsubstituted isoxazolylene group, ), A substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzopuranylene group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted oxadiazolyl group, A substituted or unsubstituted pyridazinylene group, a substituted or unsubstituted thiazolylene group or a substituted or unsubstituted tetrazolylene group, which is an oxadiazolylene group. When X ₁ of the formula (1) are to have at least one substituent, the substituent refers to the above-mentioned bar.

According to one embodiment, in Formula 1, X ₁ represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted naphthylene group, Or an unsubstituted phenanthrenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted triphenylenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted thienylene group, A substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyrimidinylene group, A substituted or unsubstituted quinolinylene group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzothiophenylene group (dibenzothiophenylene group), a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted quinazolinylene group, ne, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted triazinylene, substituted or unsubstituted pyridazinylene, substituted or unsubstituted thiazolylene group, substituted or unsubstituted thiazolylene group, substituted or unsubstituted thiophenylene group, An unsubstituted tetrazolylene group, but is not limited thereto.

Specifically, in Formula 1, X ₁ may be represented by any one of Formulas 5 (1) to 5 (16)

In formulas (5) to (16), Z ₁ to Z ₈ independently represent hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; -CN; A hydroxyl group; -NO ₂ ; An amino group; An amidino group; Hydrazine; Hydrazone; A carboxyl group or a salt thereof; Sulfonic acid group or its salt; Phosphoric acid or its salts; A C ₁ -C ₂₀ alkyl group; A C ₁ -C ₂₀ alkoxy group; Wherein R _{1 is selected} from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, amidino, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₂₀ alkyl group substituted with at least one of C ₁ -C ₂₀ alkoxy groups and a C ₁ -C ₂₀ alkoxy group; A C ₆ -C ₂₀ aryl group; A C ₂ -C ₂₀ heteroaryl group; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, salts, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, C ₆ -C ₂₀ aryl group and C ₂ -C ₂₀ heteroaryl group, a C ₆ -C ₂₀ aryl substituted with one or more of the group and a C ₂ - A C ₂₀ heteroaryl group; &Lt; / RTI &gt;

Here, * is a binding site with anthracene in Chemical Formula 1, and * 'may be a binding site with N in Chemical Formula 1.

For example, in formulas (5) (5) to (16), Z ₁ to Z ₈ independently represent hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; -CN; A hydroxyl group; -NO ₂ ; An amino group; An amidino group; Hydrazine; Hydrazone; A carboxyl group or a salt thereof; Sulfonic acid group or its salt; Phosphoric acid or its salts; A methyl group, an ethyl group, a propyl group, a butyl group and a pentyl group; A methoxy group, an ethoxy group, a propoxy group, a butoxy group and a pentoxy group; Wherein R _{1 is selected} from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, amidino, hydrazine, hydrazone, carboxyl group or salt thereof, A methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group and a pentoxy group; A phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group and a fluorenyl group; A pyridinyl group, a pyrimidinyl group, a tridinyl group, a quinolyl group and a carbazolyl group; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A phenyl group substituted with at least one of a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group , A trizinyl group, a quinolyl group and a carbazolyl group; But is not limited thereto.

In the above formula (1), m may be an integer of 1 to 5, for example, 1, 2 or 3, but is not limited thereto.

The amine compound represented by Formula 1 may be, for example, one of the following compounds 1 to 109, but is not limited thereto.

At least one of Ar ₁ and Ar ₂ of the amine-based compound represented by the formula _{(1), "-F;-CN; -NO 2} ; - at least one -F a C ₁ -C ₆₀ alkyl group substituted with a; C ₂ - A C ₆₀ heteroaryl group and a group selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, a hydroxyl group, -NO ₂ , an amino group, an amidino group, a hydrazine, a hydrazone, 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 ₂ -C ₆₀ aryl group, a phosphoric acid or its salt, a C ₁ -C ₆₀ alkyl group, C ₆₀ heteroaryl groups substituted one or more C ₂ -C ₆₀ heteroaryl group of; because at least one of the electronic receiver (electron withdrawing group) selected from the group substituted by C ₆ -C ₆₀ aryl group consisting of ", as a The displayed moiety (see Formula 1 ') may have the property of attracting electrons:

&Lt; Formula (1) &gt;

As a result, the amine compound represented by the general formula (1) can have excellent electron transporting properties because it has a moiety represented by A having an electron attracting property in addition to naphthyl-anthracene core having an electron number. Further, when the electronic receiver is a substituted or unsubstituted C ₂ -C ₆₀ hetero aryl group ring, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group E receptor and not directly (direct) connected to N of formula (I) , And C ₆ -C ₆₀ aryl group is interposed therebetween, the organic light emitting device employing the amine compound represented by Formula 1 may have excellent efficiency characteristics. On the other hand, when the electron acceptor is CN, the organic light emitting device employing the amine compound may have excellent lifetime characteristics.

Without wishing to be bound by any particular theory, it is believed that i) an amine compound containing a naphthyl-anthracene core without an electron acceptor as described above, or ii) an amine compound containing a naphthyl-anthracene core containing pyridine directly linked to N, Highst Occupied Molecular Orbital) The electron density can mostly be concentrated on the anthracene side. However, the HOMO electron density of the amine compound represented by Formula 1 may be dispersed to the amine side, and the LUMO (Lowest Unoccupied Molecular Orbital) electron density of the amine compound represented by Formula 1 is relatively fixed to the anthracene side So that the dipole property of the amine compound molecule represented by the formula (1) becomes large. Accordingly, the electron transporting property of the amine compound represented by Formula 1 can be improved.

Accordingly, the organic light emitting device employing the amine compound represented by Formula 1 can have low driving voltage, high efficiency, high brightness, and long life.

The amine compound having the formula (1) can be synthesized using a known organic synthesis method. The method of synthesizing the amine compound can be easily recognized by those skilled in the art with reference to the following embodiments.

At least one of the amine compounds of Formula 1 may be used between a pair of electrodes of the organic light emitting device. For example, at least one of the above-mentioned amine-based compounds can be used in a light emitting layer and / or between a cathode and a light emitting layer (for example, an electron transporting layer, an electron injecting layer or a functional layer having both electron transporting performance and electron injecting performance) .

Therefore, the organic layer includes a first electrode, a second electrode opposite to the first electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer contains an amine compound represented by the formula (1) There is provided an organic light emitting device comprising at least one organic light emitting device.

In the present specification, the phrase "(the organic layer) contains one or more amine-based compounds" means that one or more amine compounds belonging to the general formula (1) Or more of the amine-based compound ".

For example, the organic layer may contain only the compound 1 as the amine compound. At this time, the compound 1 may exist in the light emitting layer or the electron transport layer of the organic light emitting device. Alternatively, the organic layer may include the compound 1 and the compound 3 as the amine compound. In this case, the compound 1 and the compound 3 are present in the same layer (for example, both the compound 1 and the compound 3 may be present in the electron transporting layer) or exist in different layers (for example, The compound 3 may be present in the light-emitting layer and the compound 3 may be present in the hole-transporting layer).

The organic layer includes a hole injection layer, a hole transport layer, a functional layer (hereinafter referred to as an "H-functional layer") having both a hole injection function and a hole transport function, a buffer layer, an electron blocking layer, (Hereinafter referred to as an "E-functional layer") having both a blocking layer, an electron transporting layer, an electron injecting layer, and an electron transporting function and an electron injecting function.

In the present specification, the term "organic layer" refers to a single layer and / or a plurality of layers interposed between the first and second electrodes of the organic light emitting device.

The organic layer includes a light emitting layer, and the light emitting layer may include at least one of the amine compounds.

The amine compound contained in the light emitting layer may serve as a host. When the amine compound in the light emitting layer serves as a host, the light emitting layer may further include a fluorescent dopant. In this case, the fluorescent dopant may be a blue fluorescent dopant. Meanwhile, the amine compound included in the light emitting layer may serve as a dopant. When the amine compound in the light emitting layer serves as a dopant, the amine compound may be a blue fluorescent dopant.

Meanwhile, the organic layer may include an electron transporting layer, and the electron transporting layer may include at least one of the amine-based compounds.

1 schematically shows a cross-sectional view of an organic light emitting device 10 according to an embodiment of the present invention. Hereinafter, a structure and a manufacturing method of an organic light emitting diode according to an embodiment of the present invention will be described with reference to FIG.

As the substrate 11, a substrate used in a conventional organic light emitting device can be used, and a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness can be used.

The first electrode 13 may be formed by providing a first electrode material on the substrate using a deposition method, a sputtering method, or the like. When the first electrode 13 is an anode, the first electrode material may be selected from materials having a high work function to facilitate hole injection. The first electrode 13 may be a reflective electrode or a transmissive electrode. As the material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity can be used. Alternatively, when magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium- The one electrode 13 may be formed as a reflective electrode.

The first electrode 13 may have a single layer or two or more multi-layer structures. For example, the first electrode 13 may have a three-layer structure of ITO / Ag / ITO, but the present invention is not limited thereto.

An organic layer 15 is formed 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 (HIL) may be formed on the first electrode 13 by various methods such as a vacuum deposition method, a spin coating method, a casting method, and an LB method.

When the hole injection layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the desired hole injection layer, and the like. For example, About 500 ° C, a vacuum of about 10 ^-8 to about 10 ^-3 torr, and a deposition rate of about 0.01 to about 100 Å / sec.

When the hole injection layer is formed by the spin coating method, the coating conditions vary depending on the compound used as the material of the hole injection layer, the structure and the thermal properties of the desired hole injection layer, and the coating is performed at a coating rate of about 2000 rpm to about 5000 rpm The rate of heat treatment for removing the solvent after coating may be selected from the range of about 80 ° C to 200 ° C, but is not limited thereto.

As the hole injecting material, a known hole injecting material can be used. As the known hole injecting material, for example, N, N'-diphenyl-N, N'-bis- [4- (phenyl- N'-diphenyl-N'-bis- [4- (phenyl-m-tolyl-amino) -phenyl] -biphenyl- (4,4'-diamine: DNTPD), copper phthalocyanine and the like, m-MTDATA [4,4 ', 4 "-tris (3-methylphenylphenylamino) triphenylamine], NPB N, N'-diphenylbenzidine), TDATA, 2-TNATA, Pani / DBSA (Polyaniline / Dodecylbenzenesulfonic acid: N, N'- / Dodecylbenzenesulfonic acid), PEDOT / PSS (poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate) / CSA (polyaniline / camphor sulfonic acid) or PANI / PSS (polyaniline) / poly (4-styrenesulfonate): polyaniline) / poly But it can be used, but are not limited to:

The thickness of the hole injection layer may be from about 100 A to about 10,000 A, for example, from about 100 A to about 1000 A. When the thickness of the hole injection layer satisfies the above-described range, satisfactory hole injection characteristics can be obtained without a substantial increase in driving voltage.

Next, a hole transport layer (HTL) may be formed on the hole injection layer by various methods such as a vacuum deposition method, a spin coating method, a casting method, and an LB method. In the case of forming the hole transporting layer by the vacuum deposition method and the spinning method, the deposition conditions and the coating conditions vary depending on the compound to be used, but they can generally be selected from substantially the same range of conditions as the formation of the hole injection layer.

As the hole transporting material, known hole transporting materials include, for example, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, and N, N'-bis (3-methylphenyl) Diphenyl- [1,1-biphenyl] -4,4'-diamine (TPD), 4,4 ', 4 "-tris (N-carbazolyl) triphenylamine (4,4' N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine (N, N'- '-diphenylbenzidine)), but the present invention is not limited thereto.

The thickness of the hole transporting layer may be from about 50 Å to about 2000 Å, for example, from about 100 Å to about 1500 Å. When the thickness of the hole transporting layer satisfies the above-described range, satisfactory hole transporting characteristics can be obtained without substantially increasing the driving voltage.

The H-functional layer may include at least one of the hole injection layer material and the hole transport layer material as described above, and the H-functional layer may have a thickness of about 500 Å to about 10,000 Å, For example, from about 100 angstroms to about 1000 angstroms. When the thickness of the H-functional layer satisfies the above-described range, satisfactory hole injection and aqueous characteristics can be obtained without substantial increase in driving voltage.

At least one of the hole injection layer, the hole transport layer, and the H-functional layer may include at least one of a compound represented by the following Chemical Formula 300 and a compound represented by the following Chemical Formula 350:

&Lt; Formula 300 >

&Lt; EMI ID =

Of the above formulas 300 and 350, Ar ₁₁ , Ar ₁₂ , Ar ₂₁ and Ar ₂₂ are, independently of each other, a substituted or unsubstituted C ₆ -C ₆₀ arylene group. For a description of Ar ₁₁ , Ar ₁₂ , Ar ₂₁ and Ar ₂₂ , refer to the detailed description of L ₁ above.

In Formula 300, e and f may be, independently of each other, an integer of 0 to 5, or 0, 1 or 2. For example, e may be 1 and f may be 0, but is not limited thereto.

In formulas 300 and 350, R ₅₁ to R ₅₈ , R ₆₁ to R ₆₉ and R ₇₁ and R ₇₂ independently represent hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, -NO ₂ , A substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₆₀ cycloalkyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, A substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, or a substituted or unsubstituted C ₆ -C ₆₀ arylthio group. For example, R ₅₁ to R ₅₈ , R ₆₁ to R _69, and R ₇₁ and R ₇₂ independently of each other represent hydrogen; heavy hydrogen; A halogen atom; A hydroxyl group; Cyano; -NO ₂ ; An amino group; An amidino group; Hydrazine; Hydrazone; A carboxyl group or a salt thereof; Sulfonic acid group or its salt; Phosphoric acid or its salts; C ₁ -C ₁₀ alkyl group (for example, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group and the like); A C ₁ -C ₁₀ alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, etc.); A C ₁ -C ₆ alkyl group substituted with at least one of a halogen atom, a hydroxyl group, a cyano group, -NO ₂ , an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group; A phenyl group; Naphthyl group; Anthryl group; A fluorenyl group; Pyrenyl; Heavy hydrogen, a halogen atom, a hydroxyl group, a cyano group, -NO _2, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group substituted with one or more of the phenyl group, a naphthyl group, an anthryl group, fluorenyl group and pi les group; But is not limited thereto.

In the general formula (300), R ₅₉ represents a phenyl group; Naphthyl group; Anthryl group; A biphenyl group; A pyridyl group; And heavy hydrogen, a halogen atom, a hydroxyl group, a cyano group, -NO _2, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, and a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group substituted by one or more of the phenyl group, a naphthyl group, an anthryl group, a biphenyl group and a pyridyl group; &Lt; / RTI &gt;

According to one embodiment, the compound represented by Formula 300 may be represented by Formula 300A, but is not limited thereto:

&Lt; Formula 300A >

Details of R ₅₁ , R ₆₀ , R ₆₁ and R ₅₉ in the above formula (300A) are described above.

For example, at least one of the hole injection layer, the hole transporting layer, and the H-functional layer may include at least one of the following compounds 301 to 320, but is not limited thereto:

At least one of the hole injecting layer, the hole transporting layer and the H-functional layer may be formed by a known hole injecting material, a known hole transporting material, and / or a material having both hole injecting and hole transporting functions, And the like. The charge-generating material may further include a charge-generating material.

The charge-producing material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of the p-dopant include tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracano-1,4-benzoquinone di Quinone derivatives such as phosphorus (F4-TCNQ); Metal oxides such as tungsten oxide and molybdenum oxide; And a cyano group-containing compound such as the following compound 200, but are not limited thereto.

&Lt; Compound 200 > < F4-TCNQ &

When the hole-injecting layer, the hole-transporting layer, or the H-functional layer further comprises the charge-generating material, the charge-producing material is homogeneously (uniformly) injected into the hole-injecting layer, the hole- ) Dispersed, or non-uniformly distributed.

A buffer layer may be interposed between at least one of the hole injection layer, the hole transport layer, and the H-functional layer and the light emitting layer. The buffer layer may serve to increase the efficiency by compensating the optical resonance distance according to the wavelength of the light emitted from the light emitting layer. The buffer layer may include a known hole injecting material, a hole transporting material. Alternatively, the buffer layer may include one of the materials included in the hole injection layer, the hole transport layer, and the H-functional layer formed under the buffer layer.

Then, a light emitting layer (EML) can be formed on the hole transport layer, the H-functional layer, or the buffer layer by a method such as a vacuum evaporation method, a spin coating method, a casting method, or an LB method. When a light emitting layer is formed by a vacuum deposition method and a spin coating method, the deposition conditions vary depending on the compound used, but generally, the conditions can be selected from substantially the same range as the formation of the hole injection layer.

The light emitting layer may contain one or more amine compounds.

The amine compound contained in the light emitting layer may serve as a dopant (for example, a blue fluorescent dopant). At this time, the light emitting layer may further include a host in addition to the amine compound.

As the host, it is possible to use Alq ₃ , CBP (4,4'-N, N'-dicarbazole-biphenyl), PVK (poly (n-vinylcarbazole) Anthracene (ADN), TCTA, TPBI (1,3,5-tris (N-phenylbenzimidazole-2-yl) (3-tert-butyl-9,10-di (naphth-2-yl) anthracene), E3, DSA (distyrylarylene), dmCBP (see the following formula), the following compounds 501 to 509 However, the present invention is not limited thereto.

PVK ADN

Alternatively, as the host, an anthracene-based compound represented by the following formula (400) can be used:

&Lt; Formula 400 >

In Formula 400, Ar ₁₁₁ and Ar ₁₁₂ are independently a substituted or unsubstituted C ₆ -C ₆₀ arylene group; Ar ₁₁₃ to Ar ₁₁₆ independently represent a substituted or unsubstituted C ₁ -C ₁₀ alkyl group or a substituted or unsubstituted C ₆ -C ₆₀ aryl group; g, h, i and j may be an integer of 0 to 4 independently of each other.

For example, in the general formula (60), Ar ₁₁₁ and Ar ₁₁₂ represent a phenylene group, a naphthylene group, a phenanthrenylene group, or a pyrenylene group; Or a phenylene group, a naphthylene group, a phenanthrenylene group, a fluorenyl group, or a pyrenylene group substituted with at least one of a phenyl group, a naphthyl group and an anthryl group, but is not limited thereto.

G, h, i and j in formula (60) may be independently 0, 1 or 2.

중 하나일 수 있으나, 이에 한정되는 것은 아니다.In Formula 400, Ar ₁₁₃ to Ar ₁₁₆ independently represent a C ₁ -C ₁₀ alkyl group substituted by at least one of a phenyl group, a naphthyl group, and an anthryl group; A phenyl group; Naphthyl group; Anthryl group; Pyrenyl; A phenanthrenyl group; A fluorenyl group; Heavy hydrogen, a halogen atom, a hydroxyl group, a cyano group, -NO _2, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₆₀ alkyl, C _A phenyl group substituted with at least one of a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a pyrenyl group, a phenanthrenyl group and a fluorenyl group , Naphthyl group, anthryl group, pyrenyl group, phenanthrenyl group and fluorenyl group; And

But is not limited thereto.

For example, the anthracene-based compound represented by Formula 400 may be one of the following compounds, but is not limited thereto:

Alternatively, as the host, an anthracene-based compound represented by the following formula (401) can be used:

&Lt; Formula 401 >

For details of Ar ₁₂₂ to Ar ₁₂₅ in the above formula (401), see the description of Ar ₁₁₃ in the above formula (400).

Ar ₁₂₆ and Ar ₁₂₇ in Formula 401 may be, independently of each other, a C ₁ -C ₁₀ alkyl group (for example, a methyl group, an ethyl group or a propyl group).

K and l in Formula 401 may be independently an integer of 0 to 4. For example, k and l may be 0, 1 or 2.

For example, the anthracene-based compound represented by Formula 401 may be one of the following compounds, but is not limited thereto:

Meanwhile, the amine compound contained in the light emitting layer may serve as a host. In this case, the light emitting layer may further include a dopant (for example, a blue dopant, a green dopant, or a red dopant) in addition to the amine compound.

For example, the following compounds may be used as the blue dopant, but the present invention is not limited thereto.

                                            DPAVBi

      TBPe

For example, the following compounds may be used as the red dopant, but the present invention is not limited thereto. Alternatively, DCM or DCJTB described later may be used as the red dopant.

For example, the following compounds may be used as the green dopant, but the present invention is not limited thereto. Or a green dopant, the following C545T can be used.

Meanwhile, the dopant that may be included in the light emitting layer may be a Pt-complex as described below, but is not limited thereto:

In addition, the dopant that may be included in the light emitting layer may be Os-complex as described below, but is not limited thereto:

When the light emitting layer includes a host and a dopant, the dopant may be selected from the range of about 0.01 to about 15 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

The thickness of the light emitting layer may be about 100 Å to about 1000 Å, for example, about 200 Å to about 600 Å. When the thickness of the light-emitting layer satisfies the above-described range, it is possible to exhibit excellent light-emitting characteristics without substantial increase in driving voltage.

Next, an electron transport layer (ETL) is formed on the light emitting layer by various methods such as a vacuum evaporation method, a spin coating method, and a casting method. When an electron transporting layer is formed by a vacuum deposition method and a spin coating method, the conditions vary depending on the compound used, but generally, the conditions can be selected from substantially the same range as the formation of the hole injection layer. As the electron transporting layer material, a known electron transporting material can be used as a material that stably transports electrons injected from an electron injection electrode (cathode). Examples of known electron transporting materials include quinoline derivatives, especially tris (8-quinolinolate) aluminum (Alq3), TAZ, Balq, beryllium bis (benzoquinolin-10- olate: Bebq ₂ ), ADN, compound 201, compound 202, and the like may be used, but the present invention is not limited thereto.

&Lt; Compound 201 > < Compound 202 >

           BCP

On the other hand, the electron transporting layer may include at least one of the amine compounds as described above.

When the amine compound represented by Formula 1 is employed as the electron transport layer material, the efficiency and / or the lifetime can be improved. The electron transport layer containing the amine compound represented by Formula 1 may further include a metal complex (for example, lithium quinolate) as described below.

The thickness of the electron transporting layer may be about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transporting layer satisfies the above-described range, satisfactory electron transporting characteristics can be obtained without substantially increasing the driving voltage.

Alternatively, the electron transporting layer may further include a metal-containing substance in addition to a known electron transporting organic compound.

The metal-containing compound may include a Li complex. Non-limiting examples of the Li complex include lithium quinolate (Liq) or the following compound 203 and the like:

<Compound 203>

Further, an electron injection layer (EIL), which is a material having a function of facilitating the injection of electrons from the cathode, may be laminated on the electron transporting layer, which is not particularly limited.

As the electron injection layer formation material, any material known as an electron injection layer formation material such as LiF, NaCl, CsF, Li ₂ O, BaO, or the like can be used. The deposition conditions of the electron injection layer may vary depending on the compound used, but may generally be selected from the same range of conditions as the formation of the hole injection layer.

The thickness of the electron injection layer may be from about 1 A to about 100 A, and from about 3 A to about 90 A. When the thickness of the electron injection layer satisfies the above-described range, satisfactory electron injection characteristics can be obtained without substantially increasing the driving voltage.

A second electrode 17 is provided on the organic layer 15. The second electrode may be a cathode, which is an electron injection electrode. The metal for forming the second electrode may be a metal, an alloy, an electrically conductive compound, or a mixture thereof having a low work function. Specific examples thereof include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium- So that a transparent electrode can be obtained. On the other hand, in order to obtain a front light emitting element, a transparent electrode using ITO or IZO can be formed, and various modifications are possible.

The organic light emitting device has been described above with reference to FIG. 1, but the present invention is not limited thereto.

When a phosphorescent dopant is used in the light emitting layer, in order to prevent the triplet exciton or the hole from diffusing into the electron transporting layer, a vacuum evaporation method, a spin coating method, a vacuum evaporation method, or a vacuum evaporation method may be used between the hole transporting layer and the light emitting layer, The hole blocking layer HBL can be formed by a method such as a casting method, an LB method, or the like. In the case of forming the hole blocking layer by the vacuum deposition method and the spin coating method, the conditions vary depending on the compound used, but they can be generally within the same range of conditions as the formation of the hole injection layer. Known hole blocking materials can also be used. Examples thereof include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and the like. For example, the following BCP can be used as a hole blocking layer material.

The thickness of the hole blocking layer may be about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer satisfies the above-described range, excellent hole blocking characteristics can be obtained without increasing the driving voltage substantially.

Specific examples of the unsubstituted C ₁ -C ₆₀ alkyl group (or C ₁ -C ₆₀ alkyl group) in the present specification include a C ₁ -C ₆₀ alkyl group such as methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isoamyl, To 60 carbon atoms, and the substituted C ₁ -C ₆₀ alkyl group is a group in which at least one hydrogen atom of the unsubstituted C ₁ -C ₆₀ alkyl group is deuterium; -F; -Cl; -Br; -I; -CN; A hydroxyl group; -NO ₂ ; An amino group; An amidino group; Hydrazine; Hydrazone; A carboxyl group or a salt thereof; Sulfonic acid group or its salt; Phosphoric acid or its salts; Tree (C ₆ -C ₆₀ aryl) silyl group; A C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₂ -C ₆₀ alkenyl group and a C ₂ -C ₆₀ alkynyl group; Wherein R _{1 is selected} from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, amidino, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₂ -C ₆₀ alkenyl group and a C ₂ -C ₆₀ alkynyl group; A C ₃ -C ₆₀ cycloalkyl group, a C ₃ -C ₆₀ cycloalkenyl group, a C ₆ -C ₆₀ aryl group, a C ₂ -C ₆₀ heteroaryl group, a C ₆ -C ₆₀ aralkyl group, a C ₆ -C ₆₀ aryloxy group And a C ₆ -C ₆₀ arylthio group; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, salts, C ₁ -C ₆₀ alkyl group, substituted with at least one C ₁ -C ₆₀ alkyl group F, C ₁ -C ₆₀ alkoxy group, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₆ - C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group substituted by one or more of C ₃ -C ₆₀ cycloalkyl, C ₃ -C ₆₀ cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₂ -C ₆₀ hetero aryl group, C ₆ -C ₆₀ aralkyl, C ₆ -C ₆₀ aryloxy and C ₆ -C ₆₀ aryl come Im; . &Lt; / RTI &gt;

In the present specification, an unsubstituted C ₁ -C ₆₀ alkoxy group (or a C ₁ -C ₆₀ alkoxy group) has a chemical formula of -OA (wherein A is an unsubstituted C ₁ -C ₆₀ alkyl group as described above) , And specific examples thereof include methoxy, ethoxy, isopropyloxy, and the like. At least one hydrogen atom in the alkoxy group may be substituted with the same substituent as the substituted C ₁ -C ₆₀ alkyl group .

In the present specification, the unsubstituted C ₂ -C ₆₀ alkenyl group (or C ₂ -C ₆₀ alkenyl group) includes one or more carbon double bonds at the middle or end of the unsubstituted C ₂ -C ₆₀ alkyl group it means. Examples include ethenyl, propenyl, butenyl, and the like. At least one hydrogen atom in the C ₂ -C ₆₀ alkenyl group may be substituted with the same substituent as in the case of the substituted C ₁ -C ₆₀ alkyl group described above.

In the present specification, the unsubstituted C ₂ -C ₆₀ alkynyl group (or C ₂ -C ₆₀ alkynyl group) contains at least one carbon triple bond at the middle or end of a C ₂ -C ₆₀ alkyl group as defined above . Examples include ethynyl, propynyl, and the like. At least one hydrogen atom in the alkynyl group may be substituted with the same substituent as in the case of the substituted C ₁ -C ₆₀ alkyl group described above.

In the present specification, the unsubstituted C ₃ -C ₆₀ cycloalkyl group refers to a cyclic saturated hydrocarbon monovalent group having 3 to 60 carbon atoms, and specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and the like. . At least one hydrogen atom in the cycloalkyl group may be substituted with a substituent similar to that of the substituted C ₁ -C ₆₀ alkyl group described above.

In the present specification, an unsubstituted C ₃ -C ₆₀ cycloalkenyl group refers to a cyclic unsaturated hydrocarbon group having at least one carbon-carbon double bond but not an aromatic ring, and specific examples thereof include cyclopropenyl, cyclobutenyl cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, 1,3-cyclohexadienyl, 1,4-cyclohexadienyl, 2,4-cycloheptadienyl, 1,5- Dienyl group and the like. At least one hydrogen atom of the cycloalkenyl group may be substituted with the same substituent as the substituted C ₁ -C ₆₀ alkyl group described above.

In the specification unsubstituted C ₆ -C ₆₀ aryl group refers to a monovalent (monovalent) group having between one or more ring carbon atoms comprising from 6 to 60 carbocyclic aromatic system, and unsubstituted C ₆ - C ₆₀ arylene group means a divalent group having from 6 to 60 carbon atoms carbocyclic aromatic systems containing at least one aromatic ring. When the aryl group and the arylene group include two or more rings, the two or more rings may be fused to each other. At least one hydrogen atom of the aryl group and the arylene group may be substituted with the same substituent as the substituted C ₁ -C ₆₀ alkyl group described above.

Examples of the substituted or unsubstituted C ₆ -C ₆₀ aryl group include a phenyl group, a C ₁ -C ₁₀ alkylphenyl group (for example, an ethylphenyl group), a C ₁ -C ₁₀ alkyl biphenyl group (for example, ethyl biphenyl group O-, m-, and p-tolyl groups, o-, m- and p-fluorophenyl groups, dichlorophenyl groups), dicyanophenyl groups, trifluoromethoxyphenyl groups, (N, N'-dimethyl) aminophenyl group, (N, N'-diphenyl) aminophenyl group, pentaerythrityl group, p-cumene group, mesityl group, phenoxyphenyl group, group, an indenyl group, a naphthyl group, a halonaphthyl group (e.g., naphthyl fluoro), C ₁ -C ₁₀ alkyl naphthyl group (e.g., a methyl naphthyl group), C ₁ -C ₁₀ alkoxy-naphthyl group (e.g. For example, a methoxynaphthyl group), an anthracenyl group, an azenyl group, an heptalenyl group, an acenaphthylenyl group, a phenarenyl group, a fluorenyl group, an anthraquinolyl group, Nyl, pyrenyl , A chrysenyl group, an ethyl-chrysenyl group, a picenyl group, a perylenyl group, a chloroperylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenylenyl group, a hexaphenyl group, a hexacenyl group, , A trinaphthylenyl group, a heptaphenyl group, a heptacenyl group, a pyranthrenyl group, an obarenyl group and the like. Examples of the substituted C ₆ -C ₆₀ aryl group include unsubstituted C ₆ -C ₆₀ Can be easily recognized by referring to examples of aryl groups and substituents of the substituted C ₁ -C ₆₀ alkyl group. Examples of the substituted or unsubstituted C ₆ -C ₆₀ arylene group may be easily recognized with reference to the examples of the substituted or unsubstituted C ₆ -C ₆₀ aryl group.

The unsubstituted C ₂ -C ₆₀ heteroaryl groups herein have a system consisting of one or more aromatic rings containing one or more heteroatoms selected from N, O, P or S as ring-forming atoms and the remaining ring atoms C And wherein the unsubstituted C ₂ -C ₆₀ heteroarylene group has at least one aromatic ring containing at least one heteroatom selected from N, O, P or S and the remaining ring atoms being C 2 &lt; / RTI &gt; Herein, when the heteroaryl group and the heteroarylene group include two or more rings, two or more rings may be fused with each other. At least one hydrogen atom of the heteroaryl group and the heteroarylene group may be substituted with the same substituent as in the case of the above-mentioned C ₁ -C ₆₀ alkyl group.

Examples of the unsubstituted C ₂ -C ₆₀ heteroaryl group include a pyrazolyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a pyridinyl group, An imidazopyrimidinyl group, an imidazopyrimidinyl group, and the like can be given as examples of the pyrimidinyl group, the pyrimidinyl group, the pyrimidinyl group, the triazinyl group, the carbazolyl group, the indolyl group, the quinolinyl group, the isoquinolinyl group, Examples of the unsubstituted C ₂ -C ₆₀ hetero arylene groups may be easily recognized with reference to the examples of the substituted or unsubstituted C ₂ -C ₆₀ arylene group.

The substituted or unsubstituted C ₆ -C ₆₀ aryloxy group OA ?? ₂ the point (where, A ₂ is a C ₆ -C ₆₀ aryl group wherein the ring substituted or non-substituted), wherein the substituted or unsubstituted C ₆ - C ₆₀ aryl Im is coming ?? SA ₃ denotes (wherein, a ₃ is a C ₆ -C ₆₀ aryl group wherein the ring substituted or unsubstituted).

Hereinafter, the organic light emitting device according to one embodiment of the present invention will be described in more detail with reference to the following Synthesis Examples and Examples, but the present invention is not limited to the following Synthesis Examples and Examples.

[Example]

Synthesis Example 1: Synthesis of Compound 1

Compound 1 was synthesized according to Reaction Scheme 1-1 below.

<Reaction Scheme 1-1>

Synthesis of Intermediate 3-1

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

Synthesis of Compound 1

Intermediate 3-1 4.58g (10.0 mmol), Intermediate 4-1 2.85g (12.0 mmol), tris (dibenzylideneacetone) dipalladium (0) (Tris (dibenzylideneacetone) dipalladium (0): Pd 2 (dba) 3 0.18 g (0.2 mmol) of tri-tert-butylphosphine (P (t-Bu) ₃ ) 0.04 g (0.4 mmol) and NaO t Bu 1.44 g (15.0 mmol) was mixed with 50 ml of toluene and refluxed for 3 hours. The resulting mixture was cooled to room temperature and extracted three times with 40 mL of water and 40 mL of diethyl ether. The resulting organic layer was dried over magnesium sulfate and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography to obtain Compound 1 (4.80 g, 78% yield). Compound 1 was identified by MS-FAB and ¹ H NMR.

C ₄₆ H ₃₀ FN: calculated (calc.) 615.24, found (found) 615.22

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 2H), 7.09-7.06 (m, 1H), 6.98-6.94 (m, 2H), 6.85-6.83 (dd,

Synthesis Example 2: Synthesis of Compound 3

Compound 4 (4.98 g, 80% yield) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-3 was used instead of Intermediate 4-1. Compound 3 was identified by MS-FAB and ¹ H NMR.

C ₄₇ H ₃₀ N ₂ : calc. 622.24, found 622.23

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 (M, 3H), 7.41-7.38 (m, 2H), 7.37-7.27 (m, 2H), 7.65 (d, IH), 7.13-7.09 (m, 2H), 6.99-6.95 (m, IH), 6.88-6.85

Synthesis Example 3: Synthesis of Compound 4

Compound 4 (4.86 g, 75% yield) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-4 was used instead of Intermediate 4-1. Compound 4 was identified by MS-FAB and ¹ H NMR.

C ₄₉ H ₃₂ N ₂ : calc. 648.26, found 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 (M, 3H), 7.40-7.28 (m, 8H), 6.99-6.95 (m, 1H), 6.90-7.58 6.84 (m, 4 H), 6.74 - 6.70 (m, 2 H)

Synthesis Example 4: Synthesis of Compound 5

(4.77 g, 70% yield) was synthesized by using the same method as the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-5 was used instead of Intermediate 4-1. The compound 5 was identified by MS-FAB and ¹ H NMR.

C ₅₁ H ₃₆ FN: calc. 681.28, found 681.27

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 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, / RTI &gt; 6.70 (m, 2H), 1.66 (s, 6H)

Synthesis Example 5: Synthesis of Compound 6

Compound 6 (4.87 g, 66% yield) was synthesized using the same method as the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-6 was used instead of Intermediate 4-1. The compound 6 was identified by MS-FAB and ¹ H NMR.

C ₅₅ H ₃₅ N ₃ : calc. 737.28, found 737.29

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 8.07-8.05 (m, 1H), 7.86-7.83 (m, 2H), 7.81 (d, 1H), 7.73-7.69 (m, 2H), 7.68-7.64 (m, 2H), 7.52-7.58 (m, 2H), 7.50-7.44 (m, 6H), 7.42-7.28 , 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

Compound 7 (4.82 g, 71% yield) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-7 was used instead of Intermediate 4-1. Compound 7 was identified by MS-FAB and ¹ H NMR.

C ₄₉ H ₃₀ N ₂ S: calc. 678.21, found 678.22

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 (M, 2H), 7.61-7.58 (m, 2H), 7.54-7.51 (m, 1H), 7.47-7.41 (m, 2H), 7.39-7.27 , 7.13-7.10 (dd, IH), 7.04-7.01 (m, IH), 6.93-6.90 (m, 2H), 6.88-6.84

Synthesis Example 7: Synthesis of Compound 11

Compound 11 (4.17 g, 62% yield) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-11 was used instead of Intermediate 4-1. The compound 11 was confirmed by MS-FAB and ¹ H NMR.

C ₄₈ H ₂₉ F ₂ NO: calc. 673.22, found 673.21

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 2H), 7.37-7.29 (m, 5H), 7.16-7.13 (dd, 1H), 7.62-7.58 (m, 3H) 1H), 7.10-7.03 (m, 2H), 6.98-6.93 (m, 2H), 6.86-6.82

Synthesis Example 8: Synthesis of Compound 13

Compound 13 (4.52 g, 79% yield) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-13 was used instead of Intermediate 4-1. The compound 13 was confirmed by MS-FAB and ¹ H NMR.

C ₄₃ H ₂₈ N ₂ : calc. 572.23, found 572.23

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 7.84-7.82 (m, 2H), 7.80 (d, 1H), 7.73-7.70 (m, 2H), 7.67 (d, 1H), 7.65 (d, 1H ), 7.62-7.58 (m, 2H), 7.54-7.52 (m, 4H), 7.11-7. (m, 1 H), 6.97 - 6.95 (m, 1 H), 6.89 - 6.86 (m,

Synthesis Example 9: Synthesis of Compound 14

Compound 14 (4.29 g, yield 75%) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-14 was used instead of Intermediate 4-1. The compound 14 was identified by MS-FAB and ¹ H NMR.

C ₄₃ H ₂₈ N ₂ : calc. 572.23, found 572.24

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

Synthesis Example 10: Synthesis of Compound 17

Compound 17 (4.49 g, 73% yield) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-17 was used instead of Intermediate 4-1. Compound 17 was identified by MS-FAB and ¹ H NMR.

C ₄₃ H ₂₈ F ₃ N: calc. 615.22, found 615.23

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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, 1 H), 6.97 - 6.95 (m, 2 H), 6.86 - 6.83 (m,

Synthesis Example 11: Synthesis of Compound 18

Compound 18 (5.81 g, 70% yield) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-18 was used instead of Intermediate 4-1. Compound 18 was identified by MS-FAB and ¹ H NMR.

C ₆₁ H ₄₂ N ₂ Si: calc. 830.31, found 830.30

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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, IH), 7.06-7.02 (m, 2H), 6.96-6.94 (m, 2H), 6.80-6.76

Synthesis Example 12: Synthesis of Compound 19

Compound 19 (3.70 g, 58% yield) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-19 was used instead of Intermediate 4-1. The compound 19 was identified by MS-FAB and ¹ H NMR.

C ₄₂ H ₂₄ F ₅ N: calc. 637.18, found 637.19

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 2H), 7.12-7.09 (m, 1H), 7.02 (m, 1H), 7.50-7.54 -6.99 (m, 1H), 6.92-6.88 (m, 4H)

Synthesis Example 13: Synthesis of Compound 20

Compound 20 (4.54 g, yield 76%) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-1 was used instead of Intermediate 4-1. The compound 20 was identified by MS-FAB and ¹ H NMR.

C ₄₄ H ₂₇ N ₃ : calc. 597.22, found 597.23

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

Synthesis Example 14: Synthesis of Compound 21

Compound 21 (3.44 g, 59% yield) was synthesized using the same method as Synthesis Example 1, except that Intermediate 4-21 was used instead of Intermediate 4-1. Compound 21 was identified by MS-FAB and ¹ H NMR.

C ₄₂ H ₂₇ F ₂ N: calc. 583.21, found 583.22

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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, 1 H), 7.48-7.44 (m, 1H), 7.37-7.30 (m, 5H), 7.23-7.20 (m, 5 H), 7.04 - 7.00 (m, 2 H)

Synthesis Example 15: Synthesis of Compound 22

Compound 22 (4.03 g, yield 56%) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-22 was used instead of Intermediate 4-1. Compound 22 was identified by MS-FAB and ¹ H NMR.

C ₅₁ H ₃₃ FN ₄ : calc. 720.27, found 720.28

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 2H), 7.13-7.09 (m, 2H), 7.00 (m, 2H), 7.00-7. -6.98 (m, 1 H), 6.85 - 6.82 (m, 2 H)

Synthesis Example 16: Synthesis of Compound 23

Compound 23 (5.35 g, 70% yield) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-23 was used instead of Intermediate 4-1. The compound 23 was identified by MS-FAB and ¹ H NMR.

C ₅₆ H ₃₆ N ₄ : calc. 764.29, found 764.28

¹ H NMR (CDCl ₃ , 400 MHz) 隆 (ppm) 7.85-7.82 (m, 3H), 7.81-7.77 (m, 3H), 7.74-7.70 (M, 1H), 7.12-7.10 (m, 1H), 7.02-6.98 (m, 2H), 7.61-7.52 4H), &lt; / RTI &gt; 6.93-6.91 (m, 2H)

Synthesis Example 17: Synthesis of Compound 24

Compound 24 (4.74 g, yield 76%) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-24 was used instead of Intermediate 4-1. Compound 24 was identified by MS-FAB and ¹ H NMR.

C ₄₇ H ₃₂ N ₂ : calc. 624.26, found 624.25

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 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 1H), 7.02-6.98 (m, 3H), 6.90-6.86 (m, 2H)

Synthesis Example 18: Synthesis of Compound 25

Compound 25 (4.93 g, 79% yield) was synthesized using the same method as the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-25 was used instead of Intermediate 4-1. The compound 25 was identified by MS-FAB and ¹ H NMR.

C ₄₇ H ₃₂ N ₂ : calc. 624.26, found 624.25

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 , 7.15-7.10 (m, 4H), 6.98-6.91 (m, 3H), 6.87-6.85

Synthesis Example 19: Synthesis of Compound 26

Compound 26 (4.99 g, 80% yield) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-26 was used instead of Intermediate 4-1. Compound 26 was identified by MS-FAB and ¹ H NMR.

C ₄₇ H ₃₂ N ₂ : calc. 624.26, found 624.25

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 -7.04 (m, 1 H), 6.93 - 6.88 (m, 3 H), 6.84 - 6.80 (m,

Synthesis Example 20: Synthesis of Compound 27

Compound 27 (4.29 g, 66% yield) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-27 was used instead of Intermediate 4-1. Compound 27 was identified by MS-FAB and ¹ H NMR.

C ₄₈ H ₃₁ N ₃ : calc. 649.25, found 649.26

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 2H), 6.93-6.89 (m, 2H), 6.79-6.77 (m, 2H), 7.40-7.26

Synthesis Example 21: Synthesis of Compound 30

Compound 30 (4.99 g, 74% yield) was synthesized using the same method as the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4 -30 was used instead of Intermediate 4-1. The compound 30 was identified by MS-FAB and ¹ H NMR.

C ₅₁ H ₃₄ N ₂ : calc. 674.27, found 674.26

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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, IH), 7.65 (d, IH), 7.60-7.56 (m, 2H), 7.54-7.52 (m, 5H), 7.38-7.21 (m, 8H), 7.11-7.07 (m, 2H), 7.03-7.00 (m, 3H), 6.87-6.85

Synthesis Example 22: Synthesis of Compound 31

Compound 31 (4.98 g, 80% yield) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-1 was used instead of Intermediate 4-1. Compound 31 was identified by MS-FAB and ¹ H NMR.

C ₄₇ H ₃₀ N ₂ : calc. 622.24, found 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 (m, 4H), 7.40-7.22 (m, 8H), 7.13 (m, 2H) 2H), 7.05-7.03 (m, 1H), 6.96-6.93 (dd, 1H), 6.88-6.84

Synthesis Example 23: Synthesis of Compound 32

Compound 32 (5.40 g, 73% yield) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-32 was used instead of Intermediate 4-1. The above compound 32 was identified by MS-FAB and ¹ H NMR.

C ₅₆ H ₄₀ N ₂ : calc. 740.32, found 740.31

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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, 2H), 7.47-7.43 (m, 2H), 7.76-7.69 (m, (m, 2H), 7.39-7.26 (m, 8H), 7.15-7.10 (m, 2H), 7.06-7.04 -6.81 (m, 2H), 1.67 (s, 6H)

Synthesis Example 24: Synthesis of Compound 35

Compound 35 (5.05 g, 67% yield) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-35 was used instead of Intermediate 4-1. The above compound 35 was confirmed by MS-FAB and ¹ H NMR.

C ₅₈ H ₃₈ N ₂ O: calc. 778.30, found 778.29

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 2H), 7.05 (d, IH), 6.87 (d, IH), 6.79 (m, 2H), 7.48-7.40 -6.74 (m, 2 H), 1.64 (s, 6 H)

Synthesis Example 25: Synthesis of Compound 36

Compound 36 (5.80 g, 70% yield) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4 -36 was used instead of Intermediate 4-1. The above compound 36 was confirmed by MS-FAB and ¹ H NMR.

C ₆₃ H ₄₄ N ₂ : calc. 828.35, found 828.34

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

Synthesis Example 26: Synthesis of Compound 38

Compound 38 (5.04 g, 75% yield) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate 4-38 was used instead of Intermediate 4-1. Compound 38 was identified by MS-FAB and ¹ H NMR.

C ₅₁ H ₃₂ N ₂ : calc. 672.26, found 672.25

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

Synthesis Example 27: Synthesis of Compound 42

Synthesis of intermediate 3-42

Intermediate 3-42 was synthesized in the same manner as in the synthesis of Intermediate 3-1 in Synthesis Example 1 except that Intermediate 2-42 was used instead of Intermediate 2-1.

Synthesis of Compound 42

Compound 42 (4.54 g, 0.42 mmol) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that intermediates 3-42 and 4-27 were used instead of Intermediates 3-1 and 4-1, respectively. 65% yield). The above compound 42 was confirmed by MS-FAB and ¹ H NMR.

C ₅₂ H ₃₃ N ₃ : calc. 699.27, found 699.28

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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, 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, 1 H), 6.82 - 6.79 (m, 2 H), 6.77 - 6.73 (m,

Synthesis Example 28: Synthesis of Compound 43

Compound 43 (5.24 g, 71% yield) was synthesized in the same manner as in the synthesis of Compound 42 of Synthesis Example 27, except that Intermediate 4-43 was used instead of Intermediate 4-27. The above compound 43 was confirmed by MS-FAB and ¹ H NMR.

C ₅₆ H ₃₈ N ₂ : calc. 738.30, found 738.31

¹ H NMR (CDCl ₃ , 400 MHz)? (Ppm) 8.10-8.08 (m, 1H), 7.90-7.87 (m, 1H), 7.85-7.82 (m, 2H), 7.80 (m, 4H), 7.46-7.42 (m, 1H), 7.39-7.27 (m, 8H), 7.57-7.57 2H), 6.83-6.81 (dd, IH), 6.79 (d, IH), 1.66 (s, 6H), 7.16-7.10 (m, 3H), 6.97-6.93

Synthesis Example 29: Synthesis of Compound 45

Synthesis of intermediate 3-45

Intermediate 3-45 was synthesized in the same manner as in the synthesis of Intermediate 3-1 of Synthesis Example 1 except that Intermediate 2-45 was used instead of Intermediate 2-1.

Synthesis of Compound 45

Compound 45 (5.38 g, yield: 43%) was obtained by using the same method as the synthesis of Compound 1 of Synthesis Example 1, except that intermediates 3-45 and 4-31 were used instead of Intermediates 3-1 and 4- 80% yield) was synthesized. Compound 45 was identified by MS-FAB and ¹ H NMR.

C ₅₁ H ₃₂ N ₂ : calc. 672.26, found 672.27

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 2H), 7.10-7.06 (m, IH), 7.36-7.28 (m, 2H) , 6.97-6.92 (m, 1 H), 6.86-6.85 (dd, 1 H), 6.80-6.77 (m,

Synthesis Example 30: Synthesis of Compound 48

Compound 48 (5.50 g, yield 76%) was synthesized in the same manner as in the synthesis of Compound 45 of Synthesis Example 29, except that Intermediate 4-48 was used instead of Intermediate 4-31. The above compound 48 was confirmed by MS-FAB and ¹ H NMR.

C ₅₅ H ₃₆ N ₂ : calc. 724.29, found 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 2H), 7.11-7.07 (m, 2H), 7.21-7.17 (m, 3H), 7.55-7.40 (m, 7H), 7.36-7.32 1H), 6.99-6.94 (m, 1H), 6.87-6.85 (dd, 1H), 6.82-6.79

Synthesis Example 31: Synthesis of Compound 51

Synthesis of intermediate 3-51

Intermediate 3-51 was synthesized in the same manner as in the synthesis of intermediate 3-1 in Synthesis Example 1 except that Intermediate 2-51 was used in place of Intermediate 2-1.

Synthesis of Compound 51

Compound 51 (4.29 g, yield: 52%) was obtained in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that intermediates 3-51 and 4-4 were used instead of Intermediates 3-1 and 4- 66% yield). The above compound 51 was confirmed by MS-FAB and ¹ H NMR.

C ₄₈ H ₃₁ N ₃ : calc. 649.25, found 649.26

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 , 7.36-7.34 (m, 1H), 7.32 (m, 1H), 7.74-7.69 (m, 2H), 7.65-7.61 2H), 7.14-7.10 (m, 2H), 6.99-6.94 (m, 2H), 6.83-6.79

Synthesis Example 32: Synthesis of Compound 54

Compound 54 (4.23 g, 65% yield) was synthesized using the same method as the synthesis of compound 51 of Preparation Example 31, except that Intermediate 4-27 was used instead of Intermediate 4-4. The above compound 54 was confirmed by MS-FAB and ¹ H NMR.

C ₄₇ H ₃₀ N ₄ : calc. 650.25, found 650.24

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

Intermediate 3-57 was synthesized in the same manner as in the synthesis of Intermediate 3-1 in Synthesis Example 1 except that Intermediate 2-57 was used instead of Intermediate 2-1.

Synthesis of Compound 57

Compound 57 (4.97 g, 0.15 mmol) was synthesized by the same method as the synthesis of Compound 1 of Synthesis Example 1, except that intermediates 3-57 and 4-32 were used instead of Intermediates 3-1 and 4-1, respectively. 67% yield). Compound 57 was identified by MS-FAB and ¹ H NMR.

C ₅₅ H ₃₉ N ₃ : calc. 741.31, found 741.32

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 8.77 (dd, 1H), 8.52 (d, 1H), 8.23-8.20 (m, 1H), 7.93-7.90 (m, 1H), 7.89 (d, 1H ), 7.87 (d, 1H), 7.85-7.82 (m, 1H), 7.78-7.75 (m, 1H), 7.72-7.68 (m, 2H), 7.53-7.44 (m, 6H), 7.42-7.23 (S, 6H), 7.17-7.09 (m, 2H), 6.99-6.95 (m,

Synthesis Example 34: Synthesis of Compound 58

Synthesis of intermediate 3-58

Intermediate 3-58 was synthesized in the same manner as in the synthesis of Intermediate 3-1 in Synthesis Example 1 except that Intermediate 2-58 was used instead of Intermediate 2-1.

Synthesis of Compound 58

Compound 58 (5.67 g, yield: 58%) was obtained by using the same method as the synthesis of Compound 1 of Synthesis Example 1, except that intermediates 3-58 and 4-25 were used instead of Intermediates 3-1 and 4-1, respectively. 81% yield). The above compound 58 was identified by MS-FAB and ¹ H NMR.

C ₅₃ H ₃₆ N ₂ : calc. 700.29, found 700.30

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 , 6.96-6.92 (m, 2H), 6.86-6.83 (m, IH), 6.80-6.79 (m, 2H)

Synthesis Example 35: Synthesis of Compound 59

Compound 59 (5.46 g, 78% yield) was synthesized in the same manner as in the synthesis of Compound 58 of Preparation Example 34, except that Intermediate 4-24 was used instead of Intermediate 4-25. The above compound 59 was confirmed by MS-FAB and ¹ H NMR.

C ₅₃ H ₃₆ N ₂ : calc. 700.29, found 700.29

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 2H), 7.09-7.07 (m, 1H), 7.01-6.97 (m, 3H), 7.37-7.26 2H), 6.98 - 6.93 (m, 3H), 6.84 - 6.81 (m, 2H)

Synthesis Example 36: Synthesis of Compound 60

Compound 60 (5.08 g, 70% yield) was synthesized in the same manner as in the synthesis of Compound 58 of Preparation Example 34, except that Intermediate 4-27 was used instead of Intermediate 4-25. Compound 60 was identified by MS-FAB and ¹ H NMR.

C ₅₄ H ₃₅ N ₃ : calc. 725.28, found 725.27

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 (M, 4H), 7.68-7.65 (m, 2H), 7.55-7.52 (m, 1H), 7.48-7.43 (m, 4H), 7.39-7.24 1H), 7.03-6.99 (m, 2H), 6.93-6.89 (m, 2H), 6.82-6.80

Synthesis Example 37: Synthesis of Compound 61

Compound 61 (6.04 g, 74% yield) was synthesized in the same manner as in the synthesis of Compound 58 of Preparation Example 34, except that Intermediate 4-32 was used in place of Intermediate 4-25. The above compound 61 was confirmed by MS-FAB and ¹ H NMR.

C ₆₂ H ₄₄ N ₂ : calc. 816.35, found 816.34

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 8.69-8.67 (dd, 1H), 8.41-8.38 (m, 1H), 7.91-7.88 (m, 1H), 7.83-7.76 (m, 6H), 7.74 2H), 7.47-7.44 (m, 4H), 7.37-7.25 (m, 8H), 7.15-7.09 (m, 2H), 7.56-7. 2H), 6.99-6.94 (m, 1H), 6.90-6.86 (m, 3H), 6.83-6.79

Synthesis Example 38: Synthesis of Compound 62

Compound 62 (5.93 g, 79% yield) was synthesized in the same manner as in the synthesis of Compound 58 of Preparation Example 34, except that Intermediate 4-30 was used instead of Intermediate 4-25. The above compound 62 was identified by MS-FAB and ¹ H NMR.

C ₅₇ H ₃₈ N ₂ : calc. 750.30, found 750.29

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 (M, 2H), 7.06-7.02 (m, 2H), 7.38-7.28 (m, 5H) , 6.95-6.93 (dd, 1 H), 6.88-6.85 (m, 2 H)

Synthesis Example 39: Synthesis of Compound 63

Compound 63 (5.85 g, 78% yield) was synthesized in the same manner as in the synthesis of Compound 58 of Preparation Example 34, except that Intermediate 4-63 was used instead of Intermediate 4-25. The above compound 63 was confirmed by MS-FAB and ¹ H NMR.

C ₅₇ H ₃₈ N ₂ : calc. 750.30, found 750.31

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 2H), 7.56-7.52 (m, 5H), 7.49-7.39 (m, 6H), 7.37-7.29 , 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

Compound 64 (5.40 g, 72% yield) was synthesized in the same manner as in the synthesis of Compound 58 of Synthesis Example 34, except that Intermediate 4-48 was used instead of Intermediate 4-25. The above compound 64 was confirmed by MS-FAB and ¹ H NMR.

C ₅₇ H ₃₈ N ₂ : calc. 750.30, found 750.31

¹ H NMR (CDCl ₃ , 400 MHz)? (Ppm) 8.48-8.45 (m, 1H), 8.16-8.14 (dd, 1H), 7.87-7.82 (m, 3H), 7.81-7.68 7H), 7.09-7.07 (m, 1H), 7.01-6.99 (m, 1H), 7.48-7.40 (m, 2H), 6.95-6. 94 (dd, 1H), 6.87-6.83 (m, 2H)

Synthesis Example 41: Synthesis of Compound 66

Compound 66 (5.38 g, 77% yield) was synthesized in the same manner as in the synthesis of Compound 58 of Synthesis Example 34, except that Intermediate 4-31 was used instead of Intermediate 4-25. The above compound 66 was confirmed by MS-FAB and ¹ H NMR.

C ₅₃ H ₃₄ N ₂ : calc. 698.27, found 698.28

_{^{1 H NMR (CDCl 3, 400MHz}} ) δ (ppm) 8.06-8.04 (dd, 1H), 7.88-7.85 (m, 1H), 7.84-7.79 (m, 4H), 7.78-7.76 (m, 1H), 7.74 (M, 2H), 7.56-7.52 (m, 1H), 7.48-7.29 (m, 13H), 7.22 , 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

Compound 67 (5.36 g, 74% yield) was synthesized in the same manner as in the synthesis of Compound 58 of Synthesis Example 34, except that Intermediate 4-67 was used instead of Intermediate 4-25. The above compound 67 was confirmed by MS-FAB and ¹ H NMR.

C ₅₅ H ₃₆ N ₂ : calc. 724.29, found 724.30

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 2H), 6.94-6.90 (m, 2H), 7.06-7.01 (m, 2H)

Synthesis Example 43: Synthesis of Compound 68

Compound 68 (5.45 g, 78% yield) was synthesized in the same manner as in the synthesis of Compound 58 of Preparation Example 34, except that Intermediate 4-68 was used instead of Intermediate 4-25. The above compound 68 was confirmed by MS-FAB and ¹ H NMR.

C ₅₃ H ₃₄ N ₂ : calc. 698.27, found 698.28

¹ H NMR (CDCl ₃ , 400 MHz)? (Ppm) 7.86-7.83 (m, 2H), 7.82-7.79 (m, 2H), 7.78-7.76 2H), 7.47-7.43 (m, 3H), 7.41-7.28 (m, 8H), 7.18-7.16 (m, 2H), 7.57-7.54 1H), 7.06-7.05 (dd, 1H), 6.92-6.88 (m, 2H), 6.85-6.82

Synthesis Example 44: Synthesis of Compound 70

Compound 70 (3.56 g, 53% yield) was synthesized using the same method as the synthesis of Compound 58 of Preparation Example 34, except that Intermediate 4-70 was used instead of Intermediate 4-25. The compound 70 was identified by MS-FAB and ¹ H NMR.

C ₅₀ H ₂₉ N ₃ : calc. 671.24, found 671.23

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

Synthesis Example 45: Synthesis of Compound 73

Compound 73 (4.97 g, 65% yield) was synthesized in the same manner as in the synthesis of Compound 58 of Preparation Example 34, except that Intermediate 4-43 was used instead of Intermediate 4-25. The above compound 73 was confirmed by MS-FAB and ¹ H NMR.

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

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 (M, 2H), 7.06-7.52 (m, 2H), 7.47-7.44 (m, 3H), 7.39-7.27 (M, 2H), 6.77 (d, IH), 6.65 (s,

Synthesis Example 46: Synthesis of Compound 76

Compound 76 (6.06 g, 78% yield) was synthesized in the same manner as in the synthesis of Compound 58 of Preparation Example 34, except that Intermediate 4-76 was used instead of Intermediate 4-25. The above compound 76 was confirmed by MS-FAB and ¹ H NMR.

C ₅₉ H ₄₀ N ₂ : calc. 776.32, found 776.32

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

Synthesis Example 47: Synthesis of Compound 77

Compound 77 (5.22 g, 72% yield) was synthesized in the same manner as in the synthesis of Compound 58 of Preparation Example 34, except that Intermediate 4-77 was used instead of Intermediate 4-25. The above compound 77 was confirmed by MS-FAB and ¹ H NMR.

C ₅₄ H ₃₅ N ₃ : calc. 725.28, found 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 (m, 3H), 7.39-7.28 (m, 7H), 7.11-7.09 (m, 1 H), 7.02 (M, 2H), 6.93-6.89 (m, 2H), 6.81-6.77 (m, 2H)

Synthesis Example 48: Synthesis of Compound 78

Compound 78 (5.63 g, 75% yield) was synthesized in the same manner as in the synthesis of Compound 58 of Preparation Example 34, except that Intermediate 4-78 was used instead of Intermediate 4-25. The above compound 78 was confirmed by MS-FAB and ¹ H NMR.

C ₅₇ H ₃₈ N ₂ : calc. 750.30, found 750.29

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 2H), 7.74-7.68 (m, 4H), 7.66-7.63 (m, 3H), 7.58-7.52 (m, 4H), 7.48-7.44 (M, 2H), 6.84-6.81 (m, 2H), 7.34-7.25 (m, 8H), 7.16-7.15

Synthesis Example 49: Synthesis of Compound 79

Compound 79 (5.00 g, yield 69%) was synthesized in the same manner as in the synthesis of Compound 58 of Preparation Example 34, except that Intermediate 4-79 was used instead of Intermediate 4-25. The above compound 79 was confirmed by MS-FAB and ¹ H NMR.

C ₅₄ H ₃₅ N ₃ : calc. 725.28, found 725.27

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 (M, 2H), 6.92-6.88 (m, 2H), 7.39-7.24 (m, 2H), 6.81 - 6.78 (m, 2H)

Synthesis Example 50: Synthesis of Compound 82

Synthesis of intermediate 3-82

Intermediate 3-82 was synthesized in the same manner as in the synthesis of Intermediate 3-1 of Synthesis Example 1 except that Intermediate 2-82 was used instead of Intermediate 2-1.

Synthesis of Compound 82

Compound 82 (5.20 g, 0.20 mmol) was synthesized by the same method as in the synthesis of Compound 1 of Synthesis Example 1, except that intermediates 3-82 and 4-25 were used instead of Intermediates 3-1 and 4-1, respectively. 67% yield). The above compound 82 was confirmed by MS-FAB and ¹ H NMR.

C ₅₉ H ₄₀ N ₂ : calc. 776.32, found 776.33

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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, 1H), 7.56-7.53 (m, 1H), 7.49-7.44 (m, 4H), 7.38-7.24 , 6.96-6.92 (m, 2H), 6.87-6.83 (m, IH), 6.81-6.78 (m, 2H)

Synthesis Example 51: Synthesis of Compound 83

Compound 83 (5.58 g, 68% yield) was synthesized using the same method as the synthesis of compound 82 of Preparation Example 50, except that Intermediate 4-48 was used instead of Intermediate 4-25. The compound 83 was identified by MS-FAB and ¹ H NMR.

C ₆₃ H ₄₂ N ₂ : calc. 826.33, found 826.32

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 7H), 7.16-7.14 (m, 1H), 7.05-7.00 (m, 2H), 7.56-7.54 (dd, 1H), 7.49-7.40 (m, 6H), 7.38-7.22 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

Intermediate 3-84 was synthesized in the same manner as in the synthesis of Intermediate 3-1 of Synthesis Example 1 except that Intermediate 2-84 was used instead of Intermediate 2-1.

Synthesis of Compound 84

Compound 84 (4.90 g, 0.42 mmol) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that intermediates 3-84 and 4-30 were used instead of Intermediates 3-1 and 4-1, respectively. 62% yield). Compound 84 was identified by MS-FAB and ¹ H NMR.

C ₆₀ H ₄₂ N ₂ : calc. 790.33, found 790.32

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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, 2H), 6.82 (d, 1H), 7.40-7.25 (m, 8H), 7.13-7.11 1H), 1.62 (s, 6H)

Synthesis Example 53: Synthesis of Compound 85

Compound 84 (4.90 g, 64% yield) was synthesized in the same manner as in the synthesis of Compound 84 of Preparation Example 52, except that Intermediate 4-27 was used instead of Intermediate 4-30. The above compound 85 was identified by MS-FAB and ¹ H NMR.

C ₅₇ H ₃₉ N ₃ : calc. 765.31, found 765.30

¹ H NMR (CDCl ₃ , 400 MHz)? (Ppm) 8.68 (d, 1H), 8.38-8.35 (m, 1H), 7.95-7.92 (m, 2H), 7.90-7.88 (m, 2H), 7.41-7.33 (m, 2H), 7.63-7.60 (m, 2H) 2H), 6.80 (d, 1H), 7.32-7.25 (m, 4H), 7.12-7.09 1H), 1.61 (s, 6H)

Synthesis Example 54: Synthesis of Compound 86

Compound 86 (4.73 g, 64% yield) was synthesized in the same manner as in the synthesis of compound 84 of Preparation Example 52, except that Intermediate 4-31 was used in place of Intermediate 4-30. The above compound 86 was identified by MS-FAB and ¹ H NMR.

C ₅₆ H ₃₈ N ₂ : calc. 738.30, found 738.31

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 (M, 2H), 7.62-7.59 (m, 2H), 7.54-7.51 (m, 1H), 7.49-7.41 (m, 5H), 7.40-7.34 (S, 3H), 7.14-7.12 (m, IH), 7.01-6.99 (m, IH), 6.93-6.87

Synthesis Example 55: Synthesis of Compound 89

Synthesis of intermediate 3-89

Intermediate 3-89 was synthesized in the same manner as in the synthesis of Intermediate 3-1 in Synthesis Example 1 except that Intermediate 2-89 was used instead of Intermediate 2-1.

Synthesis of Compound 89

The same procedure as in the synthesis of the compound 1 of the above Synthesis Example 1 was carried out except that the intermediates 3-89 and 4-4 were used instead of the Intermediates 3-1 and 4-1, respectively, to obtain Compound 89 (5.61 g, 75% yield) was synthesized. The above compound 89 was identified by MS-FAB and ¹ H NMR.

C ₅₇ H ₃₆ N ₂ : calc. 748.29, found 748.30

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 2H), 7.59-7.55 (m, 3H), 7.54-7.48 (m, 1H), 7.72-7.67 2H), 7.02-6.98 (m, 2H), 6.90-7.27 (m, 3H), 7.47-7.43 6.86 (m, 2 H)

Synthesis Example 56: Synthesis of Compound 92

Synthesis of intermediate 3-92

Intermediate 3-92 was synthesized in the same manner as in the synthesis of Intermediate 3-1 in Synthesis Example 1 except that Intermediate 2-92 was used instead of Intermediate 2-1.

Synthesis of Compound 92

The same procedure as in the synthesis of Compound 1 of Synthesis Example 1 was carried out except that Intermediates 3-92 and 4-27 were used instead of Intermediates 3-1 and 4-1, respectively, to obtain Compound 92 (4.61 g, 61% yield). Compound 92 was identified by MS-FAB and ¹ H NMR.

C ₅₄ H ₃₃ N ₃ S: calc. 755.24, found 755.25

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

Synthesis Example 57: Synthesis of Compound 95

Synthesis of intermediate 3-95

Intermediate 3-95 was synthesized in the same manner as in the synthesis of Intermediate 3-1 in Synthesis Example 1 except that Intermediate 2-95 was used instead of Intermediate 2-1.

Synthesis of Compound 95

Compound 94 was prepared in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that intermediates 3-95 and 4-30 were used instead of Intermediates 3-1 and 4- 62% yield). The compound 95 was identified by MS-FAB and ¹ H NMR.

C ₅₇ H ₃₆ N ₂ O: calc. 764.28, found 764.29

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 (M, 2H), 7.94-7.91 (m, 1H), 7.87-7.85 (m, 1H), 7.84-7.77 2H), 6.98-6.96 (m, 1H), 6.94-7.40 (m, 5H), 7.48-7.41 6.92 (dd, 1 H), 6.88 - 6.85 (m, 2 H)

Synthesis Example 58: Synthesis of Compound 97

Synthesis of intermediate 3-97

Intermediate 3-97 was synthesized in the same manner as in the synthesis of intermediate 3-1 in Synthesis Example 1 except that Intermediate 2-97 was used instead of Intermediate 2-1.

Synthesis of Compound 97

Compound 97 was prepared in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that intermediates 3-97 and 4-4 were used instead of Intermediates 3-1 and 4-1, respectively, to obtain Compound 97 (4.96 g, 61% yield). The above compound 97 was confirmed by MS-FAB and ¹ H NMR.

C ₆₁ H ₃₉ N ₃ : calc. 813.31, found 813.32

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 2H), 7.60-7.58 (m, 1H), 7.54-7.47 (m, 7H), 7.46-7.41 (m, 4H), 7.40-7.36 1H), 7.06-7.00 (m, 2H), 6.86-6.80 (m, 3H), 7.34-7.28 (m, 4H), 7.24-7.22

Synthesis Example 59: Synthesis of Compound 98

Compound 98 (4.65 g, 59% yield) was synthesized in the same manner as in the synthesis of Compound 97 of Preparation Example 58, except that Intermediate 4-31 was used instead of Intermediate 4-4. The above compound 98 was confirmed by MS-FAB and ¹ H NMR.

C ₅₉ H ₃₇ N ₃ : calc. 787.30, found 787.29

_{^{1 H NMR (CDCl 3, 400MHz}} ) 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 (M, 1H), 7.76-7.74 (m, 1H), 7.73-7.68 (m, 4H), 7.61-7.58 7H), 7.42-7.35 (m, 6H), 7.34-7.23 (m, 6H), 7.13-7.10 (m, 1H), 7.04-7.03 (dd, 6.84 (m, 2H)

Synthesis Example 60: Synthesis of Compound 99

Synthesis of intermediate 3-99

Intermediate 3-98 was synthesized in the same manner as in the synthesis of Intermediate 3-1 in Synthesis Example 1 except that Intermediate 2-98 was used instead of Intermediate 2-1.

Synthesis of Compound 99

Compound 99 (5.03 g, yield: 83%) was obtained by using the same method as the synthesis of Compound 1 of Synthesis Example 1, except that intermediates 3-98 and 4-30 were used instead of Intermediates 3-1 and 4- 55% yield). The above compound 99 was confirmed by MS-FAB and ¹ H NMR.

C ₆₉ H ₄₅ N ₃ : calc. 915.36, found 915.35

¹ H NMR (CDCl ₃ , 400 MHz)? (Ppm) 8.90 (s, IH), 8.60-8.58 (dd, IH), 8.45 (s, IH), 8.13-8.11 (dd, IH), 7.94-7.91 1H), 7.87-7.75 (m, 5H), 7.72-7.58 (m, 7H), 7.54-7.21 (m, -6.84 (m, 2 H)

Synthesis Example 61: Synthesis of Compound 103

Compound 103 (5.71 g, yield 76%) was synthesized in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that Intermediate B37 was used instead of Intermediate 4-1. The above compound 103 was confirmed by MS-FAB and ¹ H NMR.

C ₅₆ H ₃₇ N ₃ : calc. 751.30, found 751.28

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

Synthesis Example 62: Synthesis of Compound 104

Compound 104 (5.23 g, yield 72%) was synthesized using the same method as the synthesis of compound 1 of Synthesis Example 1, except that Intermediate B38 was used instead of Intermediate 4-1. Compound 104 was identified by MS-FAB and ¹ H NMR.

C ₅₃ H ₃₄ N ₄ : calc. 726.28, found 726.27

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

Synthesis Example 63: Synthesis of Compound 107

Synthesis of intermediate 3-107

Intermediate 3-107 was synthesized in the same manner as in the synthesis of Intermediate 3-1 in Synthesis Example 1 except that Intermediate 2-58 was used instead of Intermediate 2-1.

Synthesis of Compound 107

(6.21 g, 75%) was obtained in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, except that intermediates 3-107 and B37 were used instead of Intermediates 3-1 and 4-1, respectively. Was synthesized. The above compound 107 was confirmed by MS-FAB and ¹ H NMR.

C ₆₂ H ₄₁ N ₃ : calc. 827.33, found 827.31

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

Intermediate

Example 1

As an anode, a 15 Ω / cm ² (1200 Å) ITO glass substrate was cut into a size of 50 mm × 50 mm × 0.7 mm and ultrasonically cleaned with isopropyl alcohol and purified water for 5 minutes each, then irradiated with ultraviolet rays for 30 minutes and exposed to ozone And the glass substrate was placed in a vacuum deposition apparatus.

2-TNATA was deposited on the ITO layer to form a hole injection layer having a thickness of 600 A, and 4,4'-bis [N- (1-naphthyl) -N-phenylamino] Phenyl (NPB) was deposited thereon to form a 300 Å thick hole transporting layer.

Then, 9,10-di-naphthalen-2-yl-anthracene (AND) and 4,4'-bis [2- (4- (N, N-diphenylamino) Phenyl (DPAVBi) was co-deposited at a weight ratio of 98: 2 to form a 300Å thick light emitting layer.

Thereafter, Compound 1 was deposited on the light emitting layer to form an electron transport layer having a thickness of 300 A, LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 A, and Al was deposited on the electron injection layer To form a second electrode (cathode) having a thickness of 3000 ANGSTROM.

<DPAVBi>

Example 2

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 4 was used instead of Compound 1 in forming an electron transport layer.

Example 3

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 14 was used instead of Compound 1 in forming the electron transport layer.

Example 4

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 23 was used instead of Compound 1 in forming the electron transport layer.

Example 5

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 25 was used instead of Compound 1 in forming the electron transport layer.

Example 6

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 27 was used instead of Compound 1 in forming the electron transport layer.

Example 7

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 31 was used instead of Compound 1 in forming the electron transport layer.

Example 8

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 32 was used instead of Compound 1 in forming the electron transport layer.

Example 9

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 42 was used instead of Compound 1 in forming the electron transport layer.

Example 10

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 48 was used instead of Compound 1 in forming the electron transport layer.

Example 11

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 58 was used instead of Compound 1 in forming the electron transport layer.

Example 12

An organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 60 was used instead of Compound 1 in forming the electron transport layer.

Example 13

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 62 was used instead of Compound 1 in forming the electron transport layer.

Example 14

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 66 was used instead of Compound 1 in forming the electron transport layer.

Example 15

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 70 was used instead of Compound 1 in forming the electron transport layer.

Example 16

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 77 was used instead of Compound 1 in forming the electron transport layer.

Example 17

An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound 82 was used instead of the compound 1 in forming the electron transport layer.

Example 18

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 86 was used instead of Compound 1 in forming the electron transport layer.

Example 19

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 97 was used instead of Compound 1 in forming the electron transport layer.

Example 20

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 25 was used instead of DPAVBi in forming the light emitting layer and Alq ₃ was used in place of Compound 25 in forming the electron transport layer.

Example 21

An organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 86 was used in place of DPAVBi in forming the light emitting layer and Alq ₃ was used in place of Compound 25 in forming the electron transport layer.

Example 22

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 103 was used instead of Compound 1 in forming the electron transport layer.

Example 23

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 104 was used instead of Compound 1 in forming the electron transport layer.

Example 24

An organic luminescent device was fabricated in the same manner as in Example 1, except that Compound 107 was used instead of Compound 1 in forming the electron transport layer.

Comparative Example  One

An organic light emitting device was fabricated in the same manner as in Example 1, except that Alq ₃ was used instead of Compound 1 in forming the electron transport layer.

Comparative Example  2

Compound A was synthesized according to Scheme A below:

<Reaction Scheme A>

Synthesis of intermediate 3-A

Intermediate 3-A was synthesized in the same manner as in the synthesis of intermediate 3-1 in Synthesis Example 1 except that Intermediate 1-A was used instead of Intermediate 1.

Synthesis of Compound A

Except that 4.24 g (10 mmol) of Intermediate 3-A and 2.23 g (12.0 mmol) of 4-A were used in place of Intermediates 3-1 and 4-1, respectively Compound A (3.23 g, 63% yield) was synthesized using the same method as described in Example &lt; RTI ID = 0.0 &gt;

Fabrication of organic light emitting device

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound A was used instead of Compound 1 in forming the electron transport layer.

Comparative Example  3

Compound B was synthesized according to Scheme B below:

<Reaction Scheme B>

Synthesis of Compound B

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

Fabrication of organic light emitting device

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound B was used instead of Compound 1 in forming the electron transport layer.

Comparative Example  4

Compound C was synthesized according to Scheme C below:

<Reaction formula C>

Synthesis of Compound C

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

Fabrication of organic light emitting device

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound C was used instead of Compound 1 in forming the electron transport layer.

Comparative Example 5

Compound D was synthesized according to Scheme D below:

<Reaction formula D>

Synthesis of Compound D

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

Fabrication of organic light emitting device

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound D was used instead of Compound 1 in forming the electron transport layer.

Evaluation example 1

Luminance, luminous color, efficiency (@ current density 50 mA / cm ² ) and half life (@ 100 mA / cm ² ) of the organic luminescent devices of Examples 1 to 20 and Comparative Examples 1 to 5 were measured with a PR650 Spectroscan Source Measurement Unit. (Manufactured by PhotoResearch). The results are shown in Table 1 below.

The light-
Host Emitting layer dopant Electronic
Transport layer Driving
Voltage
(V) Luminance
(cd / m ² ) efficiency
(cd / A) Luminous color antipathy
life span
(hr) Example 1 ADN DPVABi Compound 1 5.36 3,335 6.67 blue 492 Example 2 ADN DPVABi Compound 4 5.32 3,390 6.78 blue 596 Example 3 ADN DPVABi Compound 14 5.29 3,380 6.76 blue 542 Example 4 ADN DPVABi Compound 23 5.24 3,470 6.94 blue 589 Example 5 ADN DPVABi Compound 25 5.26 3,465 6.93 blue 536 Example 6 ADN DPVABi Compound 27 5.21 3,505 7.01 blue 564 Example 7 ADN DPVABi Compound 31 5.26 3.280 6.56 blue 632 Example 8 ADN DPVABi Compound 32 5.30 3,440 6.88 blue 559 Example 9 ADN DPVABi Compound 42 5.23 3,565 7.13 blue 658 Example 10 ADN DPVABi Compound 48 5.31 3,435 6.87 blue 524 Example 11 ADN DPVABi Compound 58 5.26 3,580 7.16 blue 532 Example 12 ADN DPVABi Compound 60 5.24 3,515 7.03 blue 582 Example 13 ADN DPVABi Compound 62 5.31 3,605 7.21 blue 529 Example 14 ADN DPVABi Compound 66 5.27 3,345 6.69 blue 608 Example 15 ADN DPVABi Compound 70 5.16 3,015 6.03 blue 583 Example 16 ADN DPVABi Compound 77 5.21 3,560 7.12 blue 637 Example 17 ADN DPVABi Compound 82 5.32 3,460 6.92 blue 543 Example 18 ADN DPVABi Compound 86 5.43 3,445 6.89 blue 469 Example 19 ADN DPVABi Compound 97 5.62 3,070 6.14 blue 486 Example 20 ADN Compound 25 Alq ₃ 6.86 2,190 4.38 blue 216 Example 21 ADN Compound 86 Alq ₃ 6.97 2,260 4.52 blue 238 Example 22 ADN DPVABi Compound 103 5.35 3,640 7.82 blue 659 Example 23 ADN DPVABi Compound 104 5.12 3,445 6.89 blue 618 Example 24 ADN DPVABi Compound 107 5.63 3,590 7.18 blue 689 Comparative Example 1 ADN DPVABi Alq ₃ 7.35 2,065 4.13 blue 145 Comparative Example 2 ADN DPVABi Compound A 5.71 2,865 5.73 blue 311 Comparative Example 3 ADN DPVABi Compound B 5.75 2,730 5.46 blue 320 Comparative Example 4 ADN DPVABi Compound C 5.73 2,845 5.69 blue 297 Comparative Example 5 ADN DPVABi Compound D 5.73 2,830 5.66 blue 213

From Table 1, it can be confirmed that the organic light emitting devices of Examples 1 to 19 have excellent driving voltage, luminance, efficiency, and lifetime characteristics as compared with the organic light emitting devices of Comparative Examples 1 to 5. Further, it can be confirmed that the organic light emitting devices of Examples 20 and 21 had better driving voltage and lifetime characteristics than the organic light emitting device of Comparative Example 1. [

Claims (40)

An amine compound represented by the following formula (1):
&Lt; Formula 1 >

In Formula 1,
Ar ₁ and Ar ₂ are independently selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pentalenyl group, a substituted or unsubstituted indenyl group, Or unsubstituted naphthyl, substituted or unsubstituted azulenyl, substituted or unsubstituted heptalenyl, substituted or unsubstituted indacenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted azulenyl, Acenaphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenalenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthryl Anthryl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted chrysinyl Chrysenyl, substituted or unsubstituted Naphthacenyl, substituted or unsubstituted picenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted pentaphenyl, substituted or unsubstituted hexacenyl group hexacenyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted imidazolinyl (imidazolinyl) A substituted or unsubstituted imidazopyridinyl group, a substituted or unsubstituted imidazopyrimidinyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrazinyl group a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted purinyl group, The unsubstituted quinolinyl group (q substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted quinazolinyl group (substituted or unsubstituted naphthyridinyl group), substituted or unsubstituted naphthyridinyl group (substituted or unsubstituted naphthyridinyl group) quinazolinyl, substituted or unsubstituted cinnolinyl, substituted or unsubstituted indazolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenazinylene, , A substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted pyranyl group, a substituted or unsubstituted chromenyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted naphthyl group, A substituted or unsubstituted thiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted benzoquinone group, a substituted or unsubstituted thiophenyl group, Imidazole Benzoimidazolyl, substituted or unsubstituted isoxazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted triazinyl Triazinyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazolyl, substituted or unsubstituted tetrazolyl, or substituted or unsubstituted phenanthroline A substituted or unsubstituted C ₆ -C ₆₀ aryl group or a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, which is phenonthrolinyl;
Ar &lt; _{1 &gt;} and Ar &lt; ₂ &gt; may optionally be connected to each other through a single bond;
X ₁ represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted naphthylene group, Or an unsubstituted or substituted anthrylene group, a substituted or unsubstituted triphenylenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted chrysenylene group, A substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted pyrazinylene group, A substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranylene group (dib a substituted or unsubstituted thiazolyl group or a substituted or unsubstituted tetrazolylene group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, _A C ₆ -C ₆₀ arylene group or a substituted or unsubstituted C ₂ -C ₆₀ heteroarylene group;
m is an integer from 1 to 3;
Substituents of the substituted C ₆ -C ₆₀ aryl group, the substituted C ₂ -C ₆₀ heteroaryl group, the substituted C ₆ -C ₆₀ arylene group and the substituted C ₂ -C ₆₀ heteroarylene group are deuterium; -F; -Cl; -Br; -I; -CN; A hydroxyl group; -NO ₂ ; An amino group; An amidino group; Hydrazine; Hydrazone; A carboxyl group or a salt thereof; Sulfonic acid group or its salt; Phosphoric acid or its salts; Tree (C ₆ -C ₆₀ aryl) silyl group; A C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₂ -C ₆₀ alkenyl group and a C ₂ -C ₆₀ alkynyl group; Wherein R _{1 is selected} from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, amidino, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₂ -C ₆₀ alkenyl group and a C ₂ -C ₆₀ alkynyl group; A C ₃ -C ₆₀ cycloalkyl group, a C ₃ -C ₆₀ cycloalkenyl group, a C ₆ -C ₆₀ aryl group, a C ₂ -C ₆₀ heteroaryl group, a C ₆ -C ₆₀ aralkyl group, a C ₆ -C ₆₀ aryloxy group And a C ₆ -C ₆₀ arylthio group; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, salts, C ₁ -C ₆₀ alkyl group, substituted with at least one C ₁ -C ₆₀ alkyl group F, C ₁ -C ₆₀ alkoxy group, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₆ - C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group substituted by one or more of C ₃ -C ₆₀ cycloalkyl, C ₃ -C ₆₀ cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₂ -C ₆₀ hetero aryl group, C ₆ -C ₆₀ aralkyl, C ₆ -C ₆₀ aryloxy and C ₆ -C ₆₀ aryl come Im; &Lt; / RTI &gt;
At least one of Ar &lt; _{1 &gt;} and Ar &lt; ₂ &gt;-CN; -NO ₂ ; A C ₁ -C ₆₀ alkyl group substituted by at least one -F; A C ₂ -C ₆₀ heteroaryl group; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, salts, C ₁ -C ₆₀ alkyl group, substituted with at least one C ₁ -C ₆₀ alkyl group F, C ₁ -C ₆₀ alkoxy group, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₆ - C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group, at least one substituted C ₂ -C ₆₀ heteroaryl group of; a C ₆ -C ₆₀ substituted with at least one electron receptor (electron withdrawing group) selected from the group consisting of Lt; / RTI &gt; The method according to claim 1,
Wherein the at least one electron acceptor is -F; -CN; -NO ₂ ; A C ₁ -C ₂₀ alkyl group substituted by at least one -F; A C ₂ -C ₂₀ heteroaryl group containing N as a ring-forming atom; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, salts, C ₁ -C ₂₀ alkyl group, at least one F a C ₁ -C ₂₀ alkyl group substituted by a, C ₁ -C ₂₀ alkoxy group, C ₆ -C ₂₀ aryl group and C ₂ -C ₂₀ heteroaryl group, one or more of And a C ₂ -C ₂₀ heteroaryl group substituted with a nitrogen atom and containing N as a ring-forming atom. The method according to claim 1,
Wherein the at least one electron acceptor is selected from the group consisting of -F; -CN; A C ₁ -C ₂₀ alkyl group substituted by at least one -F; Pyrrolyl, pyrazolyl, imidazolyl, imidazolinyl, imidazopyridinyl, imidazopyrimidinyl, pyridinyl, imidazopyrimidinyl, imidazopyrimidinyl, , Pyrazinyl, pyrimidinyl, benzoimidazoly, indolyl, purinyl, quinolinyl, isoquinolinyl, phthalazinyl (such as pyridyl, pyrimidinyl, The present invention relates to a method for preparing a compound of formula (I), wherein the compound is selected from the group consisting of phthalazinyl, indolizinyl, quinazolinyl, cinnolinyl, indazolyl, carbazolyl, phenazinyl, phenanthridinyl, Triazinyl, pyridazinyl, triazolyl, and tetrazolyl; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, Pyridyl, imidazolyl, imidazolidinyl, imidazopyrimidinyl, imidazopyrimidinyl, pyridinyl, pyrazinyl, pyrimidyl, pyrimidinyl, pyrimidinyl, pyrimidinyl, pyrimidinyl, Wherein R is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, benzoimidazolyl, indolyl, purinyl, quinolinyl, isoquinolinyl, phthalazinyl, indolizinyl, quinazolinyl, cinnolinyl, indazolyl, , Triazinyl, pyridazinyl, triazolyl, and tetrazolyl. The method according to claim 1,
Wherein the at least one electron acceptor is selected from the group consisting of -F; -CN; A C ₁ -C ₂₀ alkyl group substituted by at least one -F; Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl and benzoimidazolyl groups; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzoimidazolyl, and carbazolyl groups substituted with at least one of a nitrogen, a triazinyl, and a carbazolyl group; &Lt; / RTI &gt; The method according to claim 1,
Wherein the at least one electron acceptor is selected from the group consisting of -F; -CN; -CH ₂ F; -CHF _2; -CF _3; And an amine compound selected from the group consisting of the following formulas (2) (1) to (14):

Among the above-mentioned chemical formulas (2) to (14)
Z ₁₁ to Z ₁₈ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, -CN, a hydroxyl group, -NO ₂ , an amino group, an amidino group, a hydrazine, a hydrazone, A salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, , A phenanthrenyl group, a pyrenyl group, a pyridinyl group, a triazinyl group or a carbazolyl group. The method according to claim 1,
Wherein at least one of Ar ₁ and Ar ₂ is a C ₆ -C ₆₀ aryl group substituted with at least two electron acceptors. The method according to claim 1,
Wherein at least one of Ar ₁ and Ar ₂ is a phenyl group substituted with at least two electron acceptors, a substituted biphenyl group, a substituted naphthyl group, a substituted anthryl group, a substituted phenanthrenyl group, a substituted pyrenyl group, Fluorenyl group,
Wherein the electron acceptor is selected from the group consisting of pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl and carbazolyl; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, phthalazinyl, triazinyl, benzoimidazolyl, and pyridinyl substituted with at least one of halogen, Carbazolyl group; and an amine-based compound. The method according to claim 1,
An amine compound represented by the following formula (1) or (2):
&Lt; Chemical Formula 1 (1) >< Chemical Formula 1 (2)

In the above formula (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;
Among the above-mentioned formulas (1) and (2)
Ring A and ring B are substituted C ₆ -C ₂₀ aryl groups;
R ₁ and R ₂ are, independently of one another, -F; -CN; -NO ₂ ; A C ₁ -C ₆₀ alkyl group substituted by at least one -F; A C ₂ -C ₆₀ heteroaryl group; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, salts, C ₁ -C ₆₀ alkyl group, substituted with at least one C ₁ -C ₆₀ alkyl group F, C ₁ -C ₆₀ alkoxy group, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₆ - C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl groups substituted with at least one of C ₂ -C ₆₀ heteroaryl group; e receptor (electron withdrawing group) selected from the group consisting of a;
p and q are, independently of each other, an integer of 1 to 9; 9. The method of claim 8,
Formula 1 is represented by (1), at least one of a p number of R ₁ in the formula (1) (1) is a -CN, amine-based compound. 9. The method of claim 8,
Wherein at least one of R ₁ and q R ₂ of p in the formula (1) (2) is -CN. 9. The method of claim 8,
Wherein the ring A is a substituted phenyl group, a substituted biphenyl group, a substituted naphthyl group, a substituted anthryl group, a substituted phenanthrenyl group, a substituted pyrenyl group, or a substituted fluorenyl group An amine compound. 9. The method of claim 8,
Wherein the ring A and the ring B are independently selected from the group consisting of a substituted phenyl group, a substituted biphenyl group, a substituted naphthyl group, a substituted anthryl group, a substituted phenanthrenyl group, a substituted pie Lt; RTI ID = 0.0 &gt; fluorenyl &lt; / RTI &gt; group. 9. The method of claim 8,
Wherein the ring A is a substituted phenyl group, a substituted biphenyl group, a substituted naphthyl group, a substituted anthryl group, a substituted phenanthrenyl group, a substituted pyrenyl group, or a substituted fluorenyl group R ₁ is pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl and carbazolyl groups; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, phthalazinyl, triazinyl, benzoimidazolyl, and pyridinyl substituted with at least one of halogen, Carbazolyl group, and p is 2, 3 or 4. 5. The amine compound according to claim 1, wherein R &lt; 1 &gt; 9. The method of claim 8,
Wherein the ring A and the ring B are independently selected from the group consisting of a substituted phenyl group, a substituted biphenyl group, a substituted naphthyl group, a substituted anthryl group, a substituted phenanthrenyl group, a substituted pie R ₁ and R ₂ independently of one another are pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzoimidazolyl, And carbazolyl groups; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, phthalazinyl, triazinyl, benzoimidazolyl and pyridinyl substituted with at least one of halogen, Carbazolyl group; and p and q are independently of each other 2, 3 or 4. 2. The amine compound according to claim 1, 5. The method of claim 4,
At least one of Ar ₁ and Ar ₂ is a phenyl group, a biphenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, or a fluorenyl group substituted with the at least one electron withdrawing group, Amine compound. 6. The method of claim 5,
At least one of Ar ₁ and Ar ₂ is a phenyl group, a biphenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, or a fluorenyl group substituted with the at least one electron withdrawing group, Amine compound. The method according to claim 1,
Wherein at least one of Ar ₁ and Ar ₂ is a phenyl group, biphenyl group, anthryl group, anthryl group, phenanthrenyl group, pyrenyl group or fluorenyl group substituted with the above-mentioned at least one electron acceptor. The method according to claim 1,
Ar ₁ and Ar ₂ are, independently of each other, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthrenyl group, Substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrazinyl, Substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted quinolinyl groups, Or a substituted or unsubstituted phenanthrolinyl group;
Wherein at least one of Ar &lt; _{1 &gt;} and Ar &lt; ₂ &-CN; A C ₁ -C ₂₀ alkyl group substituted by at least one -F; Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl and carbazolyl groups; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzoimidazolyl, and carbazolyl groups substituted with at least one of a nitrogen, a triazinyl, and a carbazolyl group; Wherein the phenyl group, the naphthyl group, the anthryl group, the phenanthrenyl group, the pyrenyl group, or the fluorenyl group substituted with at least one electron acceptor selected from the group consisting of a halogen atom, The method according to claim 1,
Wherein Ar &lt; _{1 &gt;} and Ar &lt; ₂ &gt; are connected to each other by a single bond. The method according to claim 1,
An amine compound represented by any one of the following formulas (1A) to (1J):
&Lt; Formula 1A >

&Lt; Formula 1C >< Formula 1D >

&Lt; Formula 1E >< EMI ID =

&Lt; Formula 1G &gt;&lt;

&Lt; Formula 1I >< EMI ID =

Among the above general formulas (1A) to (1J)
Ar ₂ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted pentanenyl group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted azulenyl group, a substituted or unsubstituted Substituted or unsubstituted phenanthrenyl groups, substituted or unsubstituted phenanthrenyl groups, substituted or unsubstituted phenanthrenyl groups, substituted or unsubstituted phenanthrenyl groups, substituted or unsubstituted phenanthrenyl groups, substituted or unsubstituted phenanthrenyl groups, A substituted or unsubstituted arylthio group, an unsubstituted anthryl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted creicenyl group, A naphthacenyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted pentaphenyl group, a substituted or unsubstituted hexadecenyl group, a substituted or unsubstituted pyrrolyl group, A substituted or unsubstituted imidazopyrimidinyl group, a substituted or unsubstituted imidazolidinyl group, a substituted or unsubstituted imidazolidinyl group, a substituted or unsubstituted imidazopyrimidinyl group, a substituted or unsubstituted imidazolidinyl group, a substituted or unsubstituted imidazolidinyl group, A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyridinyl group, Or a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted indolizinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, A substituted or unsubstituted indazolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenazylene group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted furanyl group, A substituted or unsubstituted thiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzothiophenyl group, A substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzothiopyranyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted tetrazolyl group or a substituted or unsubstituted phenanthrolinyl group,
The substituted phenyl group, the substituted pentenyl group, the substituted indenylene group, the substituted naphthyl group, the substituted azulenyl group, the substituted hepthalenyl, the substituted indanecyl group, the substituted acenaphthyl group, the substituted fluorenyl group , A substituted phenanthrenyl group, a substituted phenanthrenyl group, a substituted anthryl group, a substituted fluoranthenyl group, a substituted triphenylenyl group, a substituted pyrenyl group, a substituted chrysenyl group, a substituted naphthacenyl group , A substituted phenyl group, a substituted phenyl group, a substituted hexenyl group, a substituted pyrrolyl group, a substituted pyrazolyl group, a substituted imidazolyl group, a substituted imidazolyl group, a substituted imidazolyl group, Substituted imidazopyrimidinyl groups, substituted pyridinyl groups, substituted pyrazinyl groups, substituted pyrimidinyl groups, substituted benzimidazolyl groups, substituted indolyl groups, substituted pyridinyl groups, substituted pyridinyl groups, substituted imidazopyrimidinyl groups, A quinolinyl group, a substituted phthalazinyl group, A substituted naphthyridinyl group, a substituted quinazolinyl group, a substituted cinnolinyl group, a substituted indazolyl group, a substituted carbazolyl group, a substituted phenazinyl group, a substituted phenanthridinyl group, a substituted naphthyridinyl group, A substituted thiophenyl group, a substituted benzothiophenyl group, a substituted isothiazolyl group, a substituted benzimidazolyl group, a substituted benzothiophenyl group, a substituted benzothiophenyl group, a substituted benzothiopyranyl group, a substituted benzothiophene group, Substituted thiazolyl, substituted tetrazolyl, substituted tetrazolyl, substituted dibenzothiophenyl, substituted dibenzofuranyl, substituted triazinyl, substituted oxadiazolyl, substituted pyridazinyl, substituted triazolyl, substituted tetrazolyl, and substituted phenan The substituent of the trolinyl group and the above R ₁₁ to R ₁₉ independently from each other are hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; -CN; A hydroxyl group; -NO ₂ ; An amino group; An amidino group; Hydrazine; Hydrazone; A carboxyl group or a salt thereof; Sulfonic acid group or its salt; Phosphoric acid or its salts; Tree (C ₆ -C ₆₀ aryl) silyl group; A C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₂ -C ₆₀ alkenyl group and a C ₂ -C ₆₀ alkynyl group; Wherein R _{1 is selected} from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, amidino, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₂ -C ₆₀ alkenyl group and a C ₂ -C ₆₀ alkynyl group; A C ₃ -C ₆₀ cycloalkyl group, a C ₃ -C ₆₀ cycloalkenyl group, a C ₆ -C ₆₀ aryl group, a C ₂ -C ₆₀ heteroaryl group, a C ₆ -C ₆₀ aralkyl group, a C ₆ -C ₆₀ aryloxy group And a C ₆ -C ₆₀ arylthio group; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, salts, C ₁ -C ₆₀ alkyl group, substituted with at least one C ₁ -C ₆₀ alkyl group F, C ₁ -C ₆₀ alkoxy group, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₆ - C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group substituted by one or more of C ₃ -C ₆₀ cycloalkyl, C ₃ -C ₆₀ cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₂ -C ₆₀ hetero aryl group, C ₆ -C ₆₀ aralkyl, C ₆ -C ₆₀ aryloxy and C ₆ -C ₆₀ aryl come Sy; provided that,
Formula 1A and 1B of R ₁₁ to R ₁₅ of the at least one, the formula 1C and 1D of the R ₁₁ to R _17, at least one, formula 1E and 1J of R ₁₁ to R ₁₈ and at least one formula 1F to 1I of R ₁₁ to one of the At least one of R &lt; ₁₉ &gt; is -F; -CN; -NO ₂ ; A C ₁ -C ₆₀ alkyl group substituted by at least one -F; A C ₂ -C ₆₀ heteroaryl group; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, salts, C ₁ -C ₆₀ alkyl group, substituted with at least one C ₁ -C ₆₀ alkyl group F, C ₁ -C ₆₀ alkoxy group, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₆ - an electronic receiver (electron withdrawing group) selected from the group consisting of; C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group, at least one substituted C ₂ -C ₆₀ heteroaryl group, a group. 21. The method of claim 20,
Ar ₂ represents, independently of each other, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthryl group, A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, A substituted or unsubstituted quinolinyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted thiazinyl, or a substituted or unsubstituted phenanthrolinyl group;
Of Formula 1A and 1B R ₁₁ to R ₁₅ of the at least one, the formula 1C and 1D of the R ₁₁ to R ₁₇ at least one, and R ₁₁ of formula 1E and 1J to R ₁₈ and at least one of formula 1F to 1I of the R ₁₁ of the To R &lt; ₁₉ &gt; is -F; -CN; -NO ₂ ; A C ₁ -C ₂₀ alkyl group substituted by at least one -F; Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl and carbazolyl groups; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, phthalazinyl, triazinyl, benzoimidazolyl and pyridinyl substituted with at least one of halogen, Carbazolyl group; and an amine-based compound. 21. The method of claim 20,
Wherein Ar &lt; ₂ &gt; is -F; -CN; -NO ₂ ; A C ₁ -C ₂₀ alkyl group substituted by at least one -F; Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzimidazolyl and carbazolyl groups; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, phthalazinyl, triazinyl, benzoimidazolyl, and pyridinyl substituted with at least one of halogen, An anthryl group, a phenanthrenyl group, a pyrenyl group, or a fluorenyl group substituted with at least one electron acceptor selected from the group consisting of an alkyl group, an alkoxy group, an alkoxy group, an alkoxy group, The method according to claim 1,
An amine compound represented by the following formula (1A-1) or 1A- (2)
&Lt; Formula 1A- (1) >< Formula 1A- (2) >

Among the above-mentioned formulas (1A-1) and (1A-2)
R ₁₂ , R ₁₄ , R ₂₂ and R ₂₄ independently of one another are pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, triazinyl, benzoimidazolyl and carbazolyl ; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, Pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, phthalazinyl, triazinyl, benzoimidazolyl, and pyridinyl substituted with at least one of halogen, A carbazolyl group; an electron acceptor selected from the group consisting of
Ar ₂ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pie Or a substituted or unsubstituted fluorenyl group. 24. The method of claim 23,
R ₁₂ , R ₁₄ , R ₂₂ and R ₂₄ independently of one another are -F; -CN; -CH ₂ F; -CHF _2; -CF _3; And an amine compound selected from the group consisting of the following formulas (2) (1) to (14):

Among the above-mentioned chemical formulas (2) to (14)
Z ₁₁ to Z ₁₈ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, -CN, a hydroxyl group, -NO ₂ , an amino group, an amidino group, a hydrazine, a hydrazone, A salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkyl group substituted with at least one F, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, , A phenanthrenyl group, a pyrenyl group, a pyridinyl group, a triazinyl group or a carbazolyl group.
delete The method according to claim 1,
X ₁ represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenylene group, , A substituted or unsubstituted anthrylene group, a substituted or unsubstituted triphenylenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted chrysenylene group, A substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted quinolinylene group, Substituted or unsubstituted quinazolinylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted dibenzofuranyl Group (dibenzofuranylene), a substituted or unsubstituted triazinyl group (triazinylene), substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazole jolil group or a substituted or unsubstituted tetrazol-ylene group, the amine-based compound. The method according to claim 1,
Wherein X ₁ is an amine-based compound represented by any one of formula 5 (1) to 5 (16):

Of the above-mentioned chemical formulas (5) to (16)
Z ₁ to Z ₈ are, independently of each other,
Hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; -CN; A hydroxyl group; -NO ₂ ; An amino group; An amidino group; Hydrazine; Hydrazone; A carboxyl group or a salt thereof; Sulfonic acid group or its salt; Phosphoric acid or its salts; A C ₁ -C ₂₀ alkyl group; A C ₁ -C ₂₀ alkoxy group; Wherein R _{1 is selected} from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, amidino, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₂₀ alkyl group substituted with at least one of C ₁ -C ₂₀ alkoxy groups and a C ₁ -C ₂₀ alkoxy group; A C ₆ -C ₂₀ aryl group; A C ₂ -C ₂₀ heteroaryl group; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, salts, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, C ₆ -C ₂₀ aryl group and C ₂ -C ₂₀ heteroaryl group, a C ₆ -C ₂₀ aryl substituted with one or more of the group and a C ₂ - A C ₂₀ heteroaryl group; / RTI &gt;
* Is a binding site with an anthracene of formula (1)
* Is a binding site with N in formula (1). 28. The method of claim 27,
Z ₁ to Z ₈ independently represent hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; -CN; A hydroxyl group; -NO ₂ ; An amino group; An amidino group; Hydrazine; Hydrazone; A carboxyl group or a salt thereof; Sulfonic acid group or its salt; Phosphoric acid or its salts; A methyl group, an ethyl group, a propyl group, a butyl group and a pentyl group; A methoxy group, an ethoxy group, a propoxy group, a butoxy group and a pentoxy group; Wherein R _{1 is selected} from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, amidino, hydrazine, hydrazone, carboxyl group or salt thereof, A methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group and a pentoxy group; A phenyl group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group and a fluorenyl group; A pyridinyl group, a pyrimidinyl group, a tridinyl group, a quinolyl group and a carbazolyl group; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A phenyl group substituted with at least one of a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group, a naphthyl group, an anthryl group, a phenanthrenyl group, a pyrenyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group , A trizinyl group, a quinolyl group and a carbazolyl group; &Lt; / RTI &gt; delete The method according to claim 1,
An amine compound, which is one of the following compounds 1 to 109:

A first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises the amine compound of any one of claims 1 to 24, 26 to 28, and 30, An organic light-emitting device comprising at least one organic light-emitting device. 32. The method of claim 31,
The organic layer includes a functional layer, a buffer layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, an electron injecting layer, and an electron injecting and electron transporting function having a hole injecting layer, a hole transporting layer, And at least one of functional layers which are simultaneously provided. 33. The method of claim 32,
Wherein the organic layer contains an electron transporting layer, and the electron transporting layer contains the amine compound. 34. The method of claim 33,
Wherein the electron transporting layer further comprises a metal complex. 35. The method of claim 34,
Wherein the metal complex comprises lithium quinolate. 33. The method of claim 32,
Wherein the organic layer includes a light emitting layer, and the light emitting layer contains the amine compound. 37. The method of claim 36,
Wherein the amine compound contained in the light emitting layer serves as a host and the light emitting layer further comprises a blue fluorescent dopant. 37. The method of claim 36,
Wherein the light emitting layer further comprises at least one of an anthracene compound represented by the following Chemical Formula 400 and an anthracene compound represented by the following Chemical Formula 401, wherein the amine compound contained in the light emitting layer serves as a dopant,
&Lt; Formula 400 >

&Lt; Formula 401 >

Of the above formulas (400) and (401)
Ar ₁₁₁ and Ar ₁₁₂ are, independently of each other, a substituted or unsubstituted C ₆ -C ₆₀ arylene group;
Ar ₁₁₃ to Ar ₁₁₆ and Ar ₁₂₂ to Ar ₁₂₅ are, independently of each other, a substituted or unsubstituted C ₁ -C ₁₀ alkyl group or a substituted or unsubstituted C ₆ -C ₆₀ aryl group;
Ar ₁₂₆ and Ar ₁₂₇ are, independently of each other, a C ₁ -C ₁₀ alkyl group;
g, h, i, j, k and l are independently an integer of 0 to 4,
Substituents of the substituted C ₆ -C ₆₀ arylene group, the substituted C ₆ -C ₆₀ aryl group and the substituted C ₁ -C ₁₀ alkyl group are deuterium; -F; -Cl; -Br; -I; -CN; A hydroxyl group; -NO ₂ ; An amino group; An amidino group; Hydrazine; Hydrazone; A carboxyl group or a salt thereof; Sulfonic acid group or its salt; Phosphoric acid or its salts; Tree (C ₆ -C ₆₀ aryl) silyl group; A C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₂ -C ₆₀ alkenyl group and a C ₂ -C ₆₀ alkynyl group; Wherein R _{1 is selected} from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl, -NO ₂ , amino, amidino, hydrazine, hydrazone, carboxyl group or salt thereof, A C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₂ -C ₆₀ alkenyl group and a C ₂ -C ₆₀ alkynyl group; A C ₃ -C ₆₀ cycloalkyl group, a C ₃ -C ₆₀ cycloalkenyl group, a C ₆ -C ₆₀ aryl group, a C ₂ -C ₆₀ heteroaryl group, a C ₆ -C ₆₀ aralkyl group, a C ₆ -C ₆₀ aryloxy group And a C ₆ -C ₆₀ arylthio group; And a substituent selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CN, hydroxyl group, -NO ₂ , amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, salts, C ₁ -C ₆₀ alkyl group, substituted with at least one C ₁ -C ₆₀ alkyl group F, C ₁ -C ₆₀ alkoxy group, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₆ - C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group substituted by one or more of C ₃ -C ₆₀ cycloalkyl, C ₃ -C ₆₀ cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₂ -C ₆₀ hetero aryl group, C ₆ -C ₆₀ aralkyl, C ₆ -C ₆₀ aryloxy and C ₆ -C ₆₀ aryl come Im; . 39. The method of claim 38,
Wherein Ar _{&lt; 111 &gt;} and Ar _{&lt; 112} &
A phenylene group, a naphthylene group, a phenanthrenylene group or a pyrenylene group; or
A phenylene group, a naphthylene group, a phenanthrenylene group, a fluorenyl group, or a pyrenylene group substituted with at least one of a phenyl group, a naphthyl group and an anthryl group;
Ar ₁₁₃ to Ar ₁₁₆ and Ar ₁₂₂ to Ar ₁₂₅ , independently of each other,
A C ₁ -C ₁₀ alkyl group substituted by at least one of a phenyl group, a naphthyl group and an anthryl group;
A phenyl group, a naphthyl group, an anthryl group, a pyrenyl group, a phenanthrenyl group and a fluorenyl group; And
Heavy hydrogen, a halogen atom, a hydroxyl group, a cyano group, -NO _2, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₆₀ alkyl, C _A phenyl group substituted with at least one of a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl group, a pyrenyl group, a phenanthrenyl group and a fluorenyl group , Naphthyl group, anthryl group, pyrenyl group, phenanthrenyl group and fluorenyl group; And

/ RTI &gt;
Ar ₁₂₆ and Ar ₁₂₇ independently represent a methyl group, an ethyl group or a propyl group;
g, h, i, j, k and l are independently of each other 0, 1 or 2. 33. The method of claim 32,
Wherein the organic layer includes at least one of a hole injecting layer, a hole transporting layer, and a functional layer having both a hole injecting function and a hole transporting function, and the at least one hole injecting layer, the hole transporting layer, Wherein the functional layer having a p-type dopant comprises a p-dopant.

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