KR20190099849A - Amine induced compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to an amine-based compound of chemical formula 1 and an organic light emitting device comprising the same. The amine-based compound according to an embodiment of the present specification can be used as a material of an organic material layer of the organic light emitting device, and by using the same, it is possible to improve efficiency, low driving voltage, and/or lifespan characteristics in the organic light emitting device.

Description

Amine compound and organic light emitting device including the same {AMINE INDUCED COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

The present specification relates to an amine compound and an organic light emitting device formed using the amine compound.

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. The organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.

There is a continuing need for the development of new materials for such organic light emitting devices.

US Patent Application Publication No. 2004-0251816

The present specification provides an amine compound and an organic light emitting device including the same.

The present specification provides an amine compound represented by Formula 1 below.

 [Formula 1]

In Chemical Formula 1

X is O, S, CRR ', or SO ₂ ,

Ar1 to Ar4 are the same as or different from each other, and each independently represent a substituted or substituted or unsubstituted alkyl group, a substituted or substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent substituents are bonded to each other to be substituted. Or an unsubstituted aliphatic ring, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heterocycle,

L1 and L2 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

R, R 'and R1 to R4 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted aryl group , Or a substituted or unsubstituted heteroaryl group, or combine with an adjacent group to form a substituted or unsubstituted aliphatic ring, or a substituted or unsubstituted aromatic ring,

a and b are each an integer of 0 to 3,

c and d are each an integer of 0 to 4,

n and m are each 0 or 1,

n + m≥1,

c + m ≦ 4,

d + n ≦ 4,

When a to d are plural, the substituents in the parentheses are the same or different from each other.

In addition, the present specification is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or two or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the amine compound. .

The amine compound according to the exemplary embodiment of the present specification may be used as a material of the organic material layer of the organic light emitting device, and by using the same, it is possible to improve efficiency, low driving voltage, and / or lifespan characteristics in the organic light emitting device.

1 illustrates an organic light emitting device according to an exemplary embodiment of the present specification.

Hereinafter, this specification is demonstrated in detail.

According to an exemplary embodiment of the present specification to provide an amine compound represented by the formula (1).

In the present specification, when a part "includes" a certain component, this means that it may further include other components, without excluding other components unless specifically stated otherwise.

In this specification, when a member is located "on" another member, this includes not only when a member is in contact with another member but also when another member exists between the two members.

Examples of substituents in the present specification are described below, but are not limited thereto.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.

As used herein, the term "substituted or unsubstituted" is deuterium; Nitrile group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents. For example, "a substituent to which two or more substituents are linked" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.

As used herein, the term "ring" refers to the combination of one or more atoms in a compound to form a ring. The ring atoms may be at least three or more.

In the present specification, the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. It is not.

In the present specification, specifically, the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. However, the present invention is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, penalenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto. no.

In the present specification, the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.

,

,

,

,

및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

,

,

And

And so on. However, the present invention is not limited thereto.

In the present specification, aliphatic ring groups may be exemplified by the cycloalkyl group and the aryl group.

In the present specification, the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. Although carbon number is not particularly limited, it is preferably 2 to 30 carbon atoms, the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Zolyl group, acridil group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, pe Nanthrolinyl group (phenanthroline), isooxazolyl group, thiadiazolyl group, phenothiazinyl group and dibenzofuranyl group and the like, but is not limited thereto.

In the present specification, examples of the cycloalkyl group and the aryl group may be applied to the heterocyclic group.

In the present specification, the arylene group is the same as the definition of an aryl group except that it is divalent.

In the present specification, the heteroarylene group is the same as the definition of the heteroaryl group, except that it is divalent.

According to an exemplary embodiment of the present specification, Formula 1 is represented by the following formula (2).

 [Formula 2]

In Formula 2, the definitions of X, R1, R2, Ar1 to Ar4, L1, L2, m, n, a, and b are as defined in Formula 1,

R5 and R6 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted A substituted heteroaryl group, or combine with an adjacent group to form a substituted or unsubstituted aliphatic ring, or a substituted or unsubstituted aromatic ring,

e and f are each an integer of 0 to 6,

e + m ≦ 6,

f + n ≦ 6,

When e and f are plural, the substituents in the parentheses are the same or different from each other.

According to an exemplary embodiment of the present specification, Formula 1 is represented by the following formula (3).

 [Formula 3]

In Formula 3, the definitions of X, R1, R2, Ar1 to Ar4, L1, L2, a, and b are as defined in Formula 1,

R5 and R6 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted A substituted heteroaryl group, or combine with an adjacent group to form a substituted or unsubstituted aliphatic ring, or a substituted or unsubstituted aromatic ring,

e and f are each an integer of 0 to 6,

When e and f are plural, the substituents in the parentheses are the same or different from each other.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 4 to 7.

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Formulas 4 to 7, R1 to R6, Ar1 to Ar4, L1, L2, a, b, e and f are the same as defined in Formulas 1 to 3.

According to an exemplary embodiment of the present specification, the R, R 'and R1 to R6 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted Silyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, R and R 'are the same as or different from each other, each independently represent a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, R and R 'are the same as or different from each other, and each independently a linear substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, R and R 'are the same as or different from each other, and each independently a branched substituted or unsubstituted alkyl group having 3 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, the R and R 'are the same as or different from each other, and each independently a methyl group, ethyl group, propyl group, isopropyl group, butyl group, terbutyl group, isobutyl group, pentyl group, iso Pentyl group, hexyl group, isohexyl group, heptyl group, octyl group, nonyl group, or decyl group.

According to an exemplary embodiment of the present specification, R and R 'is a methyl group.

According to an exemplary embodiment of the present specification, the R1 to R6 is hydrogen.

According to an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently contain a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted N, O, or S It is a C3-C30 heteroaryl group.

According to an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted polycyclic polyamide having 10 to 30 carbon atoms. Monocyclic heteroaryl group having 3 to 30 carbon atoms containing an aryl group, substituted or unsubstituted N, O, or S, or polycyclic having 3 to 30 carbon atoms containing substituted or unsubstituted N, O, or S Heteroaryl group.

According to an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted Substituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted anthracene groups, substituted or unsubstituted phenanthrene groups, substituted or unsubstituted triphenylene groups, substituted or unsubstituted fluorene groups, substituted or unsubstituted Substituted spirobifluorene group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted carbazole group, substituted or unsubstituted benzocarbazole group, substituted or unsubstituted Benzonaphthofuran group or a substituted or unsubstituted benzonaphthothiophene group.

According to an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; A substituted or unsubstituted quarterphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracene group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted fluorene group; Substituted or unsubstituted spirobifluorene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted benzocarbazole group; Substituted or unsubstituted benzonaphthofuran group; Or a substituted or unsubstituted benzonaphthothiophene group,

The phenyl group; Biphenyl group; Terphenyl group; Quarter-phenyl group; Naphthyl group; Anthracene groups; Phenanthrene group; Triphenylene group; Fluorene group; Spirobifluorene group; Dibenzofuran group; Dibenzothiophene group; Carbazole groups; Benzocarbazole group; Benzonaphthofuran group; Or a benzonaphthothiophene group having 1 to 10 carbon atoms substituted or unsubstituted with a deuterium, a nitrile group, a halogen group or a halogen group, a cycloalkyl group having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms substituted or unsubstituted, respectively. C3-30 hetero containing a group, a silyl group substituted with an alkyl group having 1 to 10 carbon atoms, an alkyl group having 6 to 30 carbon atoms substituted or unsubstituted with an aryl group, and at least one of N, O, or S Substituted or unsubstituted with any one or more of the aryl groups.

According to an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; A substituted or unsubstituted quarterphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracene group; Substituted or unsubstituted phenanthrene group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted fluorene group; Substituted or unsubstituted spirobifluorene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted benzocarbazole group; Substituted or unsubstituted benzonaphthofuran group; Or a substituted or unsubstituted benzonaphthothiophene group,

The phenyl group; Biphenyl group; Terphenyl group; Quarter-phenyl group; Naphthyl group; Anthracene groups; Phenanthrene group; Triphenylene group; Fluorene group; Spirobifluorene group; Dibenzofuran group; Dibenzothiophene group; Carbazole groups; Benzocarbazole group; Benzonaphthofuran group; Or the benzonaphthothiophene group, respectively, deuterium, nitrile group, fluorene group, trimethylsilyl group, fluoro group, methyl group, ethyl group, terbutyl group, isopropyl group, cyclohexyl group, trifluoromethyl group and trifluoromethoxy group Or a phenyl group, anthracene group, naphthalene group, benzocarbazole group, carbazole group, dibenzofuran group, dibenzothiophene group, dimethylfluorene group, or diphenylfluorene group.

According to an exemplary embodiment of the present specification, groups Ar1 to Ar4 adjacent to each other combine with each other to form a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heterocycle.

According to an exemplary embodiment of the present specification, the groups adjacent to each other of Ar1 to Ar4 combine with each other to form a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heterocycle.

According to an exemplary embodiment of the present specification, the groups adjacent to each other of Ar1 to Ar4 are bonded to each other to form a heterocyclic ring substituted or unsubstituted with an aryl group.

According to an exemplary embodiment of the present specification, the adjacent groups of Ar1 to Ar4 are bonded to each other to form a heterocyclic ring substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 to Ar4 may be represented by the following substituents.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond, or a substituted or unsubstituted arylene group.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond or a monocyclic substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond, or a polycyclic substituted or unsubstituted arylene group having 10 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond, a phenylene group, a bivalent biphenyl group, a divalent terphenyl group, a divalent naphthyl group, a divalent dimethylfluorene group, Or a divalent phenanthrene group.

According to an exemplary embodiment of the present specification, L1 and L2 are direct bonds.

According to one embodiment of the present specification, -N (Ar1) (Ar2) and -N (Ar3) (Ar4) may be the same as or different from each other, and may be independently represented by the following substituents.

According to yet an embodiment of the present disclosure, the amine compound of Formula 1 may be represented by the following structural formula.

According to one embodiment of the present specification, the amine compound of Formula 1 may be prepared according to the following scheme, but is not limited thereto. In the following schemes, the type and number of substituents can synthesize various kinds of intermediates as those skilled in the art appropriately select known starting materials. Reaction type and reaction conditions may be used those known in the art.

Proper combination of the formulas described in the examples herein and the intermediates on the basis of common technical knowledge, it is possible to prepare all of the amine-based compounds of Formula 1 described herein.

The organic light emitting device according to the present invention comprises a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or two or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes an amine compound of Chemical Formula 1.

The organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that at least one organic material layer is formed using the above-described compound.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers. In addition, the organic material layer may include one or more layers of an electron transport layer, an electron injection layer, and a layer for simultaneously transporting and transporting electrons, and one or more of the layers may include the compound.

For example, the structure of the organic light emitting device of the present invention may have a structure as shown in FIG. 1, but is not limited thereto.

1 illustrates an organic light emitting device in which a first electrode 2, an organic material layer 3 including an amine compound represented by Chemical Formula 1, an emission layer 4, and a second electrode 5 are sequentially stacked on a substrate 1. The structure is illustrated.

1 illustrates an organic light emitting diode and is not limited thereto.

In an exemplary embodiment of the present invention, the organic material layer including the amine compound of Formula 1 includes an electron injection layer, an electron transport layer, an electron injection and transport layer, and a hole blocking layer, and the electron injection layer, the electron transport layer, the electron The injection and transport layer, and the hole blocking layer may include the amine compound of the formula (1).

In an exemplary embodiment of the present invention, the organic material layer including the amine compound of Formula 1 includes a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer, and the hole injection layer, hole transport layer, hole The injection and transport layer, and the electron blocking layer may include the amine compound of the formula (1).

In an exemplary embodiment of the present invention, the organic material layer including the amine compound of Formula 1 may include a light emitting layer, and may include the amine compound of Formula 1 in the light emitting layer.

In an exemplary embodiment of the present invention, the organic material layer including the amine compound of Formula 1 may include a light emitting layer, and may include the amine compound of Formula 1 in a dopant of the light emitting layer.

In one embodiment of the present invention, the amine compound of Formula 1 The organic material layer may include a light emitting layer and may include the amine compound of Formula 1 as a blue dopant of the light emitting layer.

In an exemplary embodiment of the present invention, the organic material layer including the amine compound of Formula 1 may include a light emitting layer, and may include the amine compound of Formula 1 as a green dopant of the light emitting layer.

In an exemplary embodiment of the present invention, the organic material layer including the amine compound of Formula 1 may include a light emitting layer, and may include the amine compound of Formula 1 as a red dopant of the light emitting layer.

According to an exemplary embodiment of the present specification, the light emitting layer includes a compound of formula A as a host.

[Formula A]

In Chemical Formula A,

이고,X ₁₁ and X ₁₂ are the same as or different from each other, and each independently a substituted or unsubstituted 1-naphthyl group, a substituted or unsubstituted 2-naphthyl group, a substituted or unsubstituted 1-anthryl group, a substituted or unsubstituted group 2-anthryl group, substituted or unsubstituted 1-phenanthryl group, substituted or unsubstituted 2-phenanthryl group, substituted or unsubstituted 3-phenanthryl group, substituted or unsubstituted 4-phenanthryl group, Substituted or unsubstituted 9-phenanthryl group, substituted or unsubstituted 1-naphthasenyl group, substituted or unsubstituted 2-naphthacenyl group, substituted or unsubstituted 9-naphthacenyl group, substituted or unsubstituted 1 -Pyrenyl group, substituted or unsubstituted 2-pyrenyl group, substituted or unsubstituted 4-pyrenyl group, substituted or unsubstituted 3-methyl-2-naphthyl group, substituted or unsubstituted 4-methyl-1-naph Til group or the following structural formula

ego,

Y ₁₁ and Y ₁₂ are the same as or different from each other, and each independently a nitrile group, a halogen group, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 nuclear atoms, Or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

x and y are each an integer of 0-4.

In one embodiment of the present specification, X ₁₁ and X ₁₂ are the same as or different from each other, and are each independently a substituted or unsubstituted 1-naphthyl group, or a substituted or unsubstituted 2-naphthyl group.

In another exemplary embodiment, X ₁₁ and X ₁₂ are the same as or different from each other, and are each independently a 1-naphthyl group or a 2-naphthyl group.

In one embodiment of the present specification, x and y are each an integer of 0 to 2.

In one embodiment of the present specification, X ₁₁ and X ₁₂ are the same as or different from each other, and are each independently a 1-naphthyl group or a 2-naphthyl group, and x and y are each an organic electronic device.

In an exemplary embodiment of the present invention, the dopant and the host are included in the light emitting layer including the amine compound of Formula 1 in a mass ratio of 0.001: 0.999 to 0.3: 0.7.

In an exemplary embodiment of the present invention, the dopant and the host are included in the light emitting layer including the amine compound of Formula 1 in a mass ratio of 0.001: 0.999 to 0.25: 0.75.

In an exemplary embodiment of the present invention, the dopant and the host are included in the light emitting layer including the amine compound of Formula 1 in a mass ratio of 0.001: 0.999 to 0.05: 0.95.

In an exemplary embodiment of the present invention, the dopant and the host are included in the light emitting layer including the amine compound of Formula 1 in a mass ratio of 0.02: 0.98 to 0.25: 0.75.

In an exemplary embodiment of the present invention, the dopant and the host are included in the light emitting layer including the amine compound of Formula 1 in a mass ratio of 0.01: 0.99 to 0.1: 0.9.

For example, the organic light emitting device according to the present invention uses a metal vapor deposition (PVD) method such as sputtering or e-beam evaporation, and has a metal oxide or a metal oxide or an alloy thereof on a substrate. To form an anode and to form an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an organic material layer comprising an amine compound of the formula (1), and then used as a cathode thereon It can be prepared by depositing. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

As the anode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO: Al or SnO ₂ : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methyl compound), poly [3,4- (ethylene-1,2-dioxy) compound] (PEDT), polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic compounds, anthraquinones and polyaniline and poly-compounds of conductive polymers, and the like, but are not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic containing compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocyclic compounds include amine compounds, dibenzofuran derivatives, and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer is formed using the amine compound.

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. At this time, the anode is formed by depositing a metal or conductive metal oxide or an alloy thereof on the substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. And an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The present specification also provides a method of manufacturing an organic light emitting device formed using the amine compound.

Specifically, in one embodiment of the present specification, preparing a substrate; Forming a cathode or anode on the substrate; Forming at least one organic layer on the cathode or anode; And forming an anode or a cathode on the organic material layer, wherein at least one layer of the organic material layer is formed using the amine compound.

Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted. At least one arylvinyl group is substituted with the arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transporting material, a material capable of injecting electrons from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.

The electron injection layer is a layer that injects electrons from an electrode, has an ability to transport electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.

The hole blocking layer is a layer for preventing the cathode from reaching the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.

The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double side emission type according to a material used.

The preparation method of the amine compound of Formula 1 and the preparation of the organic light emitting device using the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

<Manufacture example 1>

Compound Synthesis of the Following Compound 1

                               [Compound 1]

Compound A (3.50 g, 5.97 mmol), 6- (ter-butyl) -N- (o-tolyl) dibenzo [b, d] furan-4-amine (4.13 g, 12.54) in a 500 ml round bottom flask in nitrogen atmosphere mmol) was completely dissolved in 160 ml of xylene, followed by addition of sodium terbutoxide (1.49 g, 15.53 mmol), followed by bis (tri-ter-butylphosphine) palladium (0) (0.06 g, 0.12 mmol). Heat stirring for hours. The mixture was cooled to room temperature, filtered to remove the base, and then concentrated under reduced pressure with xylene, followed by tetrahydrofuran: hexane = 1:25 to prepare Compound 1 (2.63 g, purity: 99.99%, yield: 41%). .

MS [M + H] ⁺ = 1085

<Manufacture example 2>

Compound Synthesis of the Following Compound 2

                              [Compound 2]

In a 500 ml round bottom flask in nitrogen atmosphere, Compound A (3.50 g, 5.97 mmol), 6-cyclohexyl-N- (o-tolyl) dibenzo [b, d] furan-4-amine (4.45 g, 12.54 mmol) were added. After completely dissolved in 220 ml of xylene, sodium terbutoxide (1.49 g, 15.53 mmol) was added, bis (tri-ter-butylphosphine) palladium (0) (0.06 g, 0.12 mmol) was added and heated for 4 hours. Stirred. The mixture was cooled to room temperature, filtered to remove the base, and then concentrated under reduced pressure with xylene, followed by tetrahydrofuran: hexane = 1:25 to prepare Compound 2 (1.98 g, purity: 99.99%, yield: 29%). .

MS [M + H] ⁺ = 1137

<Manufacture example 3>

Compound Synthesis of the Following Compound 3

                                        [Compound 3]

Dissolve Compound B (3.50 g, 5.82 mmol) and 4-fluoro-N- (4- (trimethylsilyl) phenyl) aniline (3.17 g, 12.23 mmol) in 150 ml of xylene in a 500 ml round-bottom flask in a nitrogen atmosphere. Sodium terbutoxide (1.46 g, 15.14 mmol) was added, bis (tri-ter-butylphosphine) palladium (0) (0.06 g, 0.12 mmol) was added and the mixture was heated and stirred for 4 hours. The mixture was cooled to room temperature, filtered to remove the base, and then concentrated under reduced pressure with xylene, followed by tetrahydrofuran: hexane = 1:25 to prepare compound 3 (2.82 g, purity: 99.99%, yield: 50%). .

MS [M + H] ⁺ = 961

<Manufacture example 4>

Compound Synthesis of Compound 4

                          [Compound 4]

Compound C (3.50 g, 5.52 mmol), 6- (ter-butyl) -N- (o-tolyl) dibenzo [b, d] furan-4-amine (3.81 g, 11.59 in a 500 ml round bottom flask in nitrogen atmosphere mmol) was completely dissolved in 170 ml of xylene, followed by addition of sodium terbutoxide (1.38 g, 14.35 mmol), bis (tri-ter-butylphosphine) palladium (0) (0.06 g, 0.11 mmol), and 5 Heat stirring for hours. The mixture was cooled to room temperature, filtered to remove the base, and then concentrated under reduced pressure with xylene, followed by tetrahydrofuran: hexane = 1:30 to prepare Compound 4 (3.15 g, purity: 99.99%, yield: 50%). .

MS [M + H] ⁺ = 1133

Production Example 5

Compound Synthesis of Compound 5

                                  [Compound 5]

Compound D (3.50 g, 5.72 mmol), 6- (ter-butyl) -N- (2-fluorophenyl) dibenzo [b, d] furan-4-amine (4.00 g) in a 500 ml round bottom flask under nitrogen atmosphere , 12.01 mmol) dissolved completely in 140 ml of xylene, followed by addition of sodium terbutoxide (1.43 g, 14.87 mmol) and bis (tri-ter-butylphosphine) palladium (0) (0.06 g, 0.12 mmol). It was then stirred for 3 hours by heating. The mixture was cooled to room temperature, filtered to remove the base, and then concentrated under reduced pressure with xylene, followed by tetrahydrofuran: hexane = 1:30 to prepare compound 5 (2.96 g, purity: 99.98%, yield: 46%). .

MS [M + H] ⁺ = 1119

<Manufacture example 6>

Compound Synthesis of the Following Compound 6

                                  [Compound 6]

Compound A (3.50 g, 5.97 mmol) and bis (4- (ter-butyl) phenyl) amine (3.52 g, 12.54 mmol) were completely dissolved in 160 ml of xylene in a 500 ml round bottom flask in a nitrogen atmosphere, followed by sodium terbutoxide ( 1.49 g, 15.53 mmol) was added, bis (tri-ter-butylphosphine) palladium (0) (0.06 g, 0.12 mmol) was added thereto, and the mixture was heated and stirred for 5 hours. The mixture was cooled to room temperature, filtered to remove the base, and then concentrated under reduced pressure with xylene, followed by tetrahydrofuran: hexane = 1:25 to prepare compound 6 (3.28 g, purity: 99.99%, yield: 56%). .

MS [M + H] ⁺ = 989

<Manufacture example 7>

Compound Synthesis of the Following Compound 7

                                  [Compound 7]

Compound B (3.50 g, 5.81 mmol), N- (4- (ter-butyl) phenyl) -9,9-dimethyl-9H-fluoren-2-amine (4.16 g, 12.21) in a 500 ml round bottom flask in a nitrogen atmosphere mmol) was completely dissolved in 160 ml of xylene, followed by addition of sodium terbutoxide (1.45 g, 15.12 mmol), followed by bis (tri-ter-butylphosphine) palladium (0) (0.06 g, 0.12 mmol). Heat stirring for hours. The mixture was cooled to room temperature, filtered to remove the base, and then concentrated under reduced pressure with xylene, followed by tetrahydrofuran: hexane = 1:25 to prepare compound 7 (2.55 g, purity: 99.99%, yield: 40%). .

MS [M + H] ⁺ = 1125

<Manufacture example 8>

Compound Synthesis of the Following Compound 8

                                  [Compound 8]

Compound C (3.50 g, 5.52 mmol), N- (4- (ter-butyl) phenyl) dibenzo [b, d] thiophen-4-amine (3.84 g, 11.59 mmol) in a 500 ml round bottom flask in a nitrogen atmosphere Completely dissolved in 170 ml of xylene, followed by addition of sodium terbutoxide (1.38 g, 14.35 mmol), and bis (tri-ter-butylphosphine) palladium (0) (0.06 g, 0.11 mmol) for 8 hours. It stirred by heating. The mixture was cooled to room temperature, filtered to remove the base, and then concentrated under reduced pressure with xylene, followed by tetrahydrofuran: hexane = 1:30 to prepare Compound 8 (3.26 g, purity: 99.99%, yield: 52%). .

MS [M + H] ⁺ = 1137

Example 1-1

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. was used as a detergent, and distilled water was filtered secondly as a filter (filtration) of Millerpore Co., Ltd. product. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.

The compound of the following compound HI1 and the following compound HI2 was thermally vacuum deposited to a thickness of 100 kPa so that the ratio of 98: 2 (molar ratio) was formed on the ITO transparent electrode as the anode thus prepared, thereby forming a hole injection layer. Compound (1150.) Represented by the following formula HT1 was vacuum deposited on the hole injection layer to form a hole transport layer. Subsequently, an electron blocking layer was formed by vacuum depositing a compound of EB1 on the hole transport layer with a film thickness of 50 GPa. Subsequently, the light emitting layer was formed by vacuum depositing the compound represented by the following formula BH and the compound 1 synthesized in Preparation Example 1 in a weight ratio of 50: 1 on the electronic blocking layer at a thickness of 200 kPa. A hole blocking layer was formed by vacuum depositing a compound represented by the following formula HB1 with a film thickness of 50 kPa on the light emitting layer. Subsequently, the compound represented by the following formula ET1 and the compound represented by the following formula LiQ were vacuum-deposited at a weight ratio of 1: 1 on the hole blocking layer to form an electron injection and transport layer having a thickness of 30 kPa. Lithium fluoride (LiF) and aluminum were deposited on the electron injection and transport layer sequentially to a thickness of 12 Å and 1,000 Å to form a cathode.

Was the deposition rate of the organic material in the above process, maintaining the range of 0.4 to 0.7Å / sec, the lithium fluoride of the cathode was 0.3Å / sec, aluminum was deposited at a rate of 2Å / sec, the degree of vacuum during the deposition to 2ⅹ10 ^-7 The organic light emitting device was manufactured by maintaining ⁵ × 10 ⁻⁶ torr.

Example 1-2 to Example 1-8

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except for using the compound shown in Table 1 below instead of the compound of Preparation Example 1.

Comparative Examples 1-1 to 1-3

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except for using the compound shown in Table 1 below instead of the compound of Preparation Example 1. The compounds of BD1 to BD3 used in the following Table 1 are as follows.

Example  One

When the current was applied to the organic light emitting diodes manufactured in Examples and Comparative Examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T95 means the time it takes for the luminance to decrease to 95% from the initial luminance (1600 nit).

compound
(Light Emitting Layer Dopant) Voltage
(V @ 10mA
/ cm ² ) efficiency
(cd / A @ 10mA
/ cm ² ) Color coordinates
(x, y) T95
(hr) Example 1-1 Preparation Example 1 4.16 6.25 (0.140, 0.045) 270 Example 1-2 Preparation Example 2 4.13 6.23 (0.141, 0.045) 265 Example 1-3 Preparation Example 3 4.28 6.44 (0.143, 0.046) 270 Example 1-4 Preparation Example 4 4.29 6.25 (0.142, 0.045) 295 Example 1-5 Preparation Example 5 4.27 6.19 (0.140, 0.047) 290 Example 1-6 Preparation Example 6 4.16 6.28 (0.142, 0.045) 270 Example 1-7 Preparation Example 7 4.21 6.44 (0.140, 0.046) 260 Example 1-8 Preparation Example 8 4.32 6.17 (0.141, 0.047) 295 Comparative Example 1-1 BD1 4.73 5.78 (0.142, 0.047) 220 Comparative Example 1-2 BD2 5.06 5.52 (0.143, 0.048) 150 Comparative Example 1-3 BD3 4.66 5.87 (0.143, 0.048) 185

As shown in Table 1, the organic light emitting device using the compound of the present invention as the dopant of the blue light emitting layer exhibited excellent characteristics in terms of efficiency, driving voltage and especially stability of the organic light emitting device.

As shown in Table 1, the compounds according to the present invention and organic electroluminescent device due diligence examples 1-1 to 1-8 using the same, the compounds according to the present invention is a silyl group, a fluorine group, a heteroaryl group, an aryl group, etc. Various color coordinates were shown, and low voltage, high efficiency, and long life were shown in the organic EL device.

The compound having the core of Intermediate A exhibits the lowest voltage characteristic, and the compound having the core of Intermediate B exhibits high efficiency. Compounds having the cores of intermediates C and D showed the best long life characteristics.

Comparative Example 1-1 is a pyrene-based dopant material which is widely used in the past, and is inferior in properties to the compound of the present invention.

In Comparative Examples 1-2 and 1-3, unlike the compound of the present invention, the central core fluorene is not condensed, and thus the amount of electrons is relatively low and the stability is poor, resulting in poor life characteristics.

Therefore, the present compounds may be utilized as a light emitting material having various color coordinates that can be applied to industrial products using light.

Although the preferred embodiment of the present invention (the light emitting layer dopant) has been described above, the present invention is not limited thereto, and various modifications and changes can be made within the scope of the claims and the detailed description of the invention. It belongs to the scope of the invention.

As shown in Table 1, the compounds according to the present invention and organic electroluminescent devices using the same In Examples 1-1 to 1-8, the compounds according to the present invention may be formed by a silyl group, a fluorine group, a heteroaryl group, an aryl group, or the like. Various color coordinates were shown, and low voltage, high efficiency, and long life were shown in the organic EL device. Compound 1 having the core of Intermediate A exhibits the lowest voltage characteristics, and Compounds 2 to 4 having the core of Intermediate B exhibit long life characteristics. Therefore, the present compounds may be utilized as a light emitting material having various color coordinates that can be applied to industrial products using light.

1: substrate
2: first electrode
3: organic layer
4: light emitting layer
5: second electrode

Claims (8)

An amine compound represented by the following formula (1):
[Formula 1]

In Chemical Formula 1
X is O, S, CRR 'or SO ₂ ,
Ar1 to Ar4 are the same as or different from each other, and each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent substituents are bonded to each other to be substituted or unsubstituted. To form a substituted alicyclic ring, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heterocycle,
L1 and L2 are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
R, R 'and R1 to R4 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted aryl group , Or a substituted or unsubstituted heteroaryl group, or combine with an adjacent group to form a substituted or unsubstituted aliphatic ring, or a substituted or unsubstituted aromatic ring,
a and b are each an integer of 0 to 3,
c and d are each an integer of 0 to 4,
n and m are each 0 or 1,
n + m≥1,
c + m ≦ 4,
d + n ≦ 4,
When a to d are plural, the substituents in the parentheses are the same or different from each other. The amine compound of claim 1, wherein Formula 1 is represented by Formula 2:
[Formula 2]

In Formula 2, the definitions of X, R1, R2, Ar1 to Ar4, L1, L2, m, n, a, and b are as defined in Formula 1,
R5 and R6 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted A substituted heteroaryl group, or combine with an adjacent group to form a substituted or unsubstituted aliphatic ring, or a substituted or unsubstituted aromatic ring,
e and f are integers from 0 to 6,
e + m ≦ 6,
f + n ≦ 6,
When e and f are plural, the substituents in parentheses are the same or different from each other. The amine compound of claim 1, wherein Formula 1 is represented by Formula 3:
[Formula 3]

In Formula 3, the definitions of X, R1, R2, Ar1 to Ar4, L1, L2, a, and b are as defined in Formula 1,
R5 and R6 are the same as or different from each other, and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted A substituted heteroaryl group, or combine with an adjacent group to form a substituted or unsubstituted aliphatic ring, or a substituted or unsubstituted aromatic ring,
e and f are integers from 0 to 6,
When e and f are plural, the substituents in parentheses are the same or different from each other. The method of claim 1, wherein Ar1 to Ar4 are the same as or different from each other, each independently substituted or unsubstituted monocyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted polycyclic aryl group having 10 to 30 carbon atoms, substituted Or a C3-C30 monocyclic heteroaryl group containing unsubstituted N, O, or S, or a C3-C30 polycyclic heteroaryl group containing substituted or unsubstituted N, O, or S Phosphorus amine compound. The amine compound of claim 1, wherein L1 and L2 are the same as or different from each other, and each independently a direct bond or a substituted or unsubstituted arylene group having 10 to 30 carbon atoms. The amine compound of claim 1, wherein Formula 1 is any one selected from the following compounds:

A first electrode; A second electrode provided to face the first electrode; And one or two or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the amine compound of any one of claims 1 to 6. Phosphorescent organic light-emitting device. The organic light emitting device of claim 6, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the amine compound.

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