KR101597334B1 - Fused hetero cyclic compound and organic light emitting device using the same - Google Patents

Abstract

The present invention relates to a novel condensed heterocyclic compound and an organic light emitting device comprising the same.

Description

FIELD OF THE INVENTION [0001] The present invention relates to a condensed heterocyclic compound and an organic light emitting device using the condensed heterocyclic compound.

The present invention relates to a novel condensed heterocyclic compound and an organic light emitting device comprising the same.

An electroluminescent device is one type of self-luminous display device, and has advantages of wide viewing angle, excellent contrast, and high response speed.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes couple to each other in the organic thin film and form a pair. The organic thin film may be composed of a single layer or a multilayer, if necessary.

The material of the organic thin film may have a light emitting function as required. For example, as the organic thin film material, a compound capable of forming a light emitting layer by itself may be used, or a compound capable of serving as a host or a dopant of a host-dopant light emitting layer may be used. In addition, as the material of the organic thin film, a compound capable of performing a role such as hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection may be used.

In order to improve the performance, life or efficiency of an organic light emitting device, development of materials for organic thin films is continuously required.

The present invention provides a novel condensed heterocyclic compound and an organic light emitting device comprising the same.

The present invention provides compounds of formula 1:

In Formula 1,

R ₁ to R ₄ and Ar are the same or different and each independently represents hydrogen, halogen, C ₁ to C ₆₀ linear or branched substituted or unsubstituted alkyl, C ₂ to C ₆₀ linear or branched Substituted or unsubstituted alkenyl, C ₂ to C ₆₀ linear or branched substituted or unsubstituted alkynyl, C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl, C ₂ to C ₆₀ C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, and C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl ≪ / RTI >

n and m are each independently an integer of 0 to 4;

Also, the present invention provides an organic light emitting device comprising a cathode, a cathode, and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers includes the compound of the above formula .

The compound according to the present invention can be used as an organic material layer material of an organic light emitting device. The compound can act as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, and the like in an organic light emitting device. In particular, the compound can be used as a light emitting layer material of an organic light emitting device. Specifically, the compound can be used as a host material for a phosphorescent light-emitting layer. In addition, the compound can be used as a hole transporting layer material of an organic light emitting device.

FIGS. 1 to 3 illustrate a stacking order of electrodes and organic layers of an organic light emitting diode according to embodiments of the present invention.
Figs. 4 and 5 show E _ox values derived from the CV measurement of Compound 105. Fig.
Figure 6 shows a UV measurement graph of Compound 105.
7 shows a PL measurement graph of Compound 105 at 254 nm.
8 is a graph showing the LTPL measurement of Compound 105 at 381 nm.

Hereinafter, the present invention will be described in detail.

The compound according to the present invention can be represented by the above formula (1). The compound according to the present invention can be used as an organic material layer material of the organic light emitting device according to the structural and physical properties of the core structure.

In the above formula (1), the halogen includes F, Cl, Br and I.

In the above formula (1), alkyl includes a straight chain or a branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents. The carbon number of the alkyl may be 1 to 60, specifically 1 to 40, more specifically 1 to 20.

In the above formula (1), alkenyl includes straight chain or branched chain having 2 to 60 carbon atoms and may be further substituted by other substituents. The carbon number of the alkenyl may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.

In the general formula (1), alkynyl includes a straight chain or a branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents. The carbon number of the alkynyl may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.

In Formula 1, the cycloalkyl includes monocyclic or polycyclic rings having 3 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic ring means a group in which cycloalkyl is directly connected to another ring group or condensed. Here, the other ring group may be a cycloalkyl group, but may be other ring groups such as heterocycloalkyl, aryl, heteroaryl, and the like. The carbon number of the cycloalkyl may be 3 to 60, specifically 3 to 40, more particularly 5 to 20.

In the above formula (1), heterocycloalkyl includes S, O or N as a heteroatom and includes monocyclic or polycyclic rings having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic ring means a group in which heterocycloalkyl is directly connected to another ring group or condensed. Here, the other ring group may be heterocycloalkyl, but may be other ring groups such as cycloalkyl, aryl, heteroaryl, and the like. The heterocycloalkyl may have from 2 to 60 carbon atoms, specifically from 2 to 40, more specifically from 3 to 20 carbon atoms.

In Formula 1, aryl includes monocyclic or polycyclic rings having 6 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic ring means a group in which aryl is directly connected to another ring group or condensed. Here, the other ring group may be aryl, but may be other ring groups such as cycloalkyl, heterocycloalkyl, heteroaryl and the like. The carbon number of the aryl may be 6 to 60, specifically 6 to 40, more specifically 6 to 20. Specific examples of aryl include phenyl, biphenyl, naphthyl, anthryl, klycenyl, phenanthrenyl, triphenylenyl, pyrenyl, tetracenyl, pentacenyl, fluorenyl, and condensed rings thereof. But is not limited thereto.

In the above formula (1), heteroaryl includes S, O or N as a heteroatom and includes monocyclic or polycyclic rings having 2 to 60 carbon atoms, and may be further substituted by other substituents. Herein, the term "polycyclic" means a heteroaryl group directly bonded to another ring group or condensed therewith. Here, the other ring group may be heteroaryl, but may be other ring groups such as cycloalkyl, heterocycloalkyl, aryl, and the like. The heteroaryl may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, more particularly 3 to 20 carbon atoms. Specific examples of heteroaryl include pyrrolyl, furanyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl, oxadiazolyl, thiadiazolyl, Thiazolyl, tetrazolyl, pyridyl, pyrimidyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxinyl, triazinyl, tetrazinyl, quinolyl, isoquinolyl, There are condensed rings of these groups such as alkyl, alkenyl, alkynyl, isoquinazolinyl, acridinyl, phenanthridyl, imidazopyridyl, diazanaphthalenyl, triazinene, dibenzothiophene, But is not limited thereto.

As used herein, the term "substituted or unsubstituted" refers to halogen, cyano, C ₁ to C ₆₀ linear or branched alkyl, C ₂ to C ₆₀ linear or branched alkenyl, C ₂ to C ₆₀ Straight or branched chain alkynyl, C ₁ to C ₆₀ straight or branched chain haloalkyl, C ₂ to C ₆₀ straight or branched chain haloalkenyl, C ₂ to C ₆₀ linear or branched haloalkyl C ₂ to C ₆₀ straight or branched chain alkoxy, C ₂ to C ₆₀ straight or branched chain alkenyloxy, C ₂ to C ₆₀ straight or branched chain alkynyloxy, C ₃ to C ₆₀ A C ₂ to C ₆₀ monocyclic or polycyclic heterocycloalkyl, a C ₆ to C ₆₀ monocyclic or polycyclic aryl, a C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl, a C ₆ to C ₆₀ monocyclic or polycyclic cycloalkyl, a monocyclic or polycyclic C ₆₀ aryloxy, and C ₂ to C ₆₀ monocyclic or polycyclic heterocyclic of aryloxy Means a substituted or unsubstituted by one or more substituents selected from the group consisting. The additional substituents may be further substituted.

According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (2) to (4).

In formulas (2) to (4), R ₁ to R ₄ and Ar are the same or different and each independently represents hydrogen, halogen, C ₁ to C ₆₀ linear or branched substituted or unsubstituted alkyl, C ₂ to C ₆₀ straight chain or branched substituted or unsubstituted alkenyl ring-chain, C ₂ to C a substituted or unsubstituted ₆₀ straight or branched chain unsubstituted alkynyl, C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl Alkyl, a C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl, a C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, and a C ₂ to C ₆₀ monocyclic or polycyclic Or unsubstituted heteroaryl.

According to one embodiment of the present invention, in the general formulas (1) to (4), R ₁ and R ₂ are the same as each other.

According to one embodiment of the present invention, R ₁ and R ₂ in the general formulas (1) to (4) are different from each other.

According to one embodiment of the present invention, in the general formulas (1) to (4), R ₁ and R ₂ and Ar are the same.

According to one embodiment of the present invention, in the general formulas (1) to (4), Ar is different from R ₁ or R ₂ . Here, R ₁ and R ₂ are the same or different.

According to one embodiment of the present invention, R ₁ , R ₂ and Ar in the general formulas (1) to (4) are different from each other.

According to one embodiment of the present invention, R ₁ and R ₂ are each independently selected from the group consisting of hydrogen, halogen, C ₁ to C ₆₀ linear or branched substituted or unsubstituted alkyl, C ₂ to C ₆₀ linear or branched C ₂ to C ₆₀ straight or branched chain substituted or unsubstituted alkynyl, C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl, C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, and C ₂ to monocyclic of C ₆₀ or polycyclic substituted or unsubstituted heteroaryl ≪ / RTI >

According to one embodiment of the present invention, R ₁ and R ₂ are hydrogen, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, and C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted Heteroaryl, < / RTI >

According to one embodiment of the present invention, R ₁ and R ₂ are the same as each other, and are C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, and C ₂ to C ₆₀ monocyclic or polycyclic Gt; heteroaryl < / RTI > Specifically, R ₁ and R ₂ are an aryl group such as phenyl, biphenyl, naphthyl, anthryl, klycenyl, phenanthrenyl, triphenylenyl, pyrenyl, tetracenyl, pentacenyl, fluorenyl, , Furanyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl, oxadiazolyl, thiadiazolyl, thiazolyl, tetrazolyl, Wherein the aryl group is selected from the group consisting of pyridyl, pyrimidyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxinyl, triazinyl, tetrazinyl, quinolyl, isoquinolyl, quinazolinyl, isoquinazolinyl, Which may be further substituted, such as, for example, phenyl, naphthyl, naphthyl, naphthyl, naphthyl, naphthyl, naphthyl, naphthyl, phenanthridinyl, imidazolopyridyl, diazanaphthalenyl, triazinene, dibenzothiophene, carbazolyl or phenazinyl. More specifically, R ₁ and R ₂ are selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthrenyl, Substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted phenanthridyl, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted carbazolyl.

According to one embodiment of the present invention, R ₁ and R ₂ are different from each other.

In one specific example, R ₁ and R ₂ are different from each other and each represents a C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, and a C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted Heteroaryl, < / RTI > Specifically, R ₁ and R ₂ may be the same or different groups and may be the same or different from each other, such as phenyl, biphenyl, naphthyl, anthryl, klycenyl, phenanthrenyl, triphenylenyl, pyrenyl, tetracenyl, pentacenyl, An aryl group or a heteroaryl group which may have a substituent selected from the group consisting of pyrrolyl, furanyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl, oxadiazolyl, thiadiazolyl, , Tetrazolyl, pyridyl, pyrimidyl, paranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxinyl, triazinyl, tetrazinyl, quinolyl, isoquinolyl, quinazolinyl, iso Which may be heteroaryl, such as quinazolinyl, acridinyl, phenanthridyl, imidazopyridyl, diazanaphthalenyl, triazinene, dibenzothiophene, carbazolyl, phenazinyl, . More specifically, R ₁ and R ₂ , which are different from each other, are selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, Substituted or unsubstituted pyrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted phenanthridyl, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted carbazolyl , Which may be further substituted.

As another specific example, R ₁ and R ₂ are mutually different groups, one of which is hydrogen and the other is a C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, and C ₂ to C ₆₀ monocyclic or polycyclic substituted or non-substituted is selected from the group consisting of unsubstituted heteroaryl. Specifically, R ₁ and R ₂ Is hydrogen and the other is an aryl group such as phenyl, biphenyl, naphthyl, anthryl, klycenyl, phenanthrenyl, triphenylenyl, pyrenyl, tetracenyl, pentacenyl, fluorenyl, or pyrrolyl , Furanyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl, oxadiazolyl, thiadiazolyl, thiazolyl, tetrazolyl, Wherein the aryl group is selected from the group consisting of pyridyl, pyrimidyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxinyl, triazinyl, tetrazinyl, quinolyl, isoquinolyl, quinazolinyl, isoquinazolinyl, Which may be further substituted, such as, for example, phenyl, naphthyl, naphthyl, naphthyl, naphthyl, naphthyl, naphthyl, naphthyl, phenanthridinyl, imidazolopyridyl, diazanaphthalenyl, triazinene, dibenzothiophene, carbazolyl or phenazinyl. More specifically, R ₁ and R ₂ One of which is hydrogen and the other is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthrenyl, substituted Or a substituted or unsubstituted pyrrolidinyl, a substituted or unsubstituted phenanthridyl, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted carbazolyl group, .

According to one embodiment of the present invention, R ₁ is hydrogen.

When the exemplified R ₁ and R ₂ are not hydrogen, they may additionally be substituted by halogen, cyano, C ₁ to C ₆₀ linear or branched alkyl, C ₂ to C ₆₀ linear or branched alkenyl, C C ₂ to C ₆₀ linear or branched alkynyl, C ₁ to C ₆₀ linear or branched haloalkyl, C ₂ to C ₆₀ linear or branched haloalkenyl, C ₂ to C ₆₀ linear or branched branched haloalkynyl, alkynyloxy of C ₁ to C ₆₀ linear or branched alkoxy, C ₂ to alkenyl group of a straight-chain or branched-chain C ₆₀ aryloxy, C ₂ to straight- or branched-chain C _60, C ₃ to C ₆₀ monocyclic or polycyclic cycloalkyl, C ₂ to C ₆₀ monocyclic or polycyclic heterocycloalkyl, C ₆ to C ₆₀ monocyclic or polycyclic aryl, C ₂ to C ₆₀ monocyclic or polycyclic hetero Aryl, C ₂ to C ₆₀ monocyclic or polycyclic heterocycloalkyl, C ₆ to C ₆₀ monocyclic or polycyclic Aryloxy, and C ₂ to C ₆₀ monocyclic or polycyclic heteroaryloxy. As a specific example, R ₁ and R ₂ exemplified above may be substituted by _one or more substituents selected from the group consisting of halogen, C ₁ to C ₆₀ linear or branched alkyl, C ₁ to C ₆₀ linear or branched haloalkyl, C ₆ to C ₆₀ monocyclic or Aryl, or a C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl. As more specific examples, R ₁ and R ₂ exemplified above are F, C ₁ to C ₆ linear or branched alkyl, C ₆ to C ₆₀ monocyclic or polycyclic aryl, or C ₂ to C ₆₀ monocyclic or Lt; / RTI > heteroaryl. As a more specific example, R ₁ and R ₂ exemplified above may be substituted with F or methyl.

According to one embodiment of the present invention, R ₁ is hydrogen, phenyl substituted with halogen, naphthyl, anthryl, phenanthrenyl, fluorenyl substituted or unsubstituted with methyl group, pyridyl, , A dibenzothiophene group or a carbazolyl group.

According to one embodiment of the present invention, R ₂ is hydrogen, phenyl substituted with halogen, naphthyl, anthryl, phenanthrenyl, substituted or unsubstituted fluorenyl with methyl group, pyridyl, , A dibenzothiophene group or a carbazolyl group.

In one embodiment of the present invention, when R ₁ or R ₂ is a carbazolyl, N of the carbazolyl may be bonded to the core structure.

According to one embodiment of the present invention, in the general formulas 1 to 4, Ar is the same or different from R ₁ or R ₂ and is selected from the group consisting of hydrogen, halogen, C ₁ to C ₆₀ linear or branched substituted or unsubstituted alkyl , C ₂ to C ₆₀ linear or branched substituted or unsubstituted alkenyl, C ₂ to C ₆₀ linear or branched substituted or unsubstituted alkynyl, C ₃ to C ₆₀ mono- or poly-substituted Or unsubstituted cycloalkyl, C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl, C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, and C ₂ to C ₆₀ Monocyclic or polycyclic substituted or unsubstituted heteroaryl.

According to one embodiment of the present invention, Ar is selected from the group consisting of C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, and C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl Is selected. Specifically, Ar is an aryl group such as phenyl, biphenyl, terphenyl, naphthyl, anthryl, klycenyl, phenanthrenyl, triphenylenyl, pyrenyl, tetracenyl, pentacenyl, fluorenyl; Or pyrrolyl, furanyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl, oxadiazolyl, thiadiazolyl, Wherein the substituent is selected from the group consisting of pyridyl, pyrimidyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxinyl, triazinyl, tetrazinyl, quinolyl, isoquinolyl, quinazolinyl, isoquinazolyl Which may be further substituted, such as, for example, phenyl, naphthyl, naphthyl, naphthyl, naphthyl, naphthyl, have. More specifically, Ar may be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted Phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted thiazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted Substituted or unsubstituted phenanthridinyl, substituted or unsubstituted phenanthridinyl, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted carbazolyl.

According to one embodiment of the present invention, Ar is phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthrenyl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, Which may be further substituted with phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthrenyl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, or phenazinyl, May be substituted with phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthrenyl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, or phenazinyl.

According to one embodiment of the present invention, Ar is phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, phenazinyl, diphenyltriazinyl or diphenyltriazinylphenyl.

According to one embodiment of the present invention, in the general formulas (1) to (4), R ₃ and R ₄ are the same or different and each independently represents a C ₁ to C ₆₀ straight or branched chain substituted or unsubstituted alkyl; Or a C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl.

According to one embodiment of the present invention, in formulas (1) to (4), R ₃ and R ₄ are the same or different and each independently represents a C ₁ to C ₂₀ straight or branched chain substituted or unsubstituted alkyl; Or a C ₆ to C ₂₀ monocyclic or polycyclic substituted or unsubstituted aryl.

According to one embodiment of the present invention, in the general formulas (1) to (4), R ₃ and R ₄ are the same or different and each independently represents a C ₁ to C ₁₂ straight or branched chain substituted or unsubstituted alkyl; Or a C ₆ to C ₁₂ monocyclic or polycyclic substituted or unsubstituted aryl.

According to one embodiment of the present invention, in the general formulas (1) to (4), R ₃ and R ₄ are the same or different and each independently methyl or phenyl.

Specific examples of the compounds of the formulas (1) to (4) are shown below, but the present invention is not limited thereto.

The compounds of the above formulas (1) to (4) can be produced on the basis of the following production example.

For example, the compound of Formula 2 may be prepared according to the following reaction scheme. Each step in the scheme can utilize reaction conditions and materials known in the art. In Reaction Scheme 1 below, if necessary, reactants and reaction conditions can be substituted with those known in the art.

[Reaction Scheme 1]

In the above Reaction Scheme 1, R ₁ to R ₄ and Ar are the same as defined in Formula 2 above.

As another example, the compound of Formula 3 may be prepared according to the following reaction scheme. Each step in the scheme can utilize reaction conditions and materials known in the art. In the following Reaction Scheme 2, reactants and reaction conditions may be substituted, if necessary, with those known in the art.

[Reaction Scheme 2]

In the above Reaction Scheme 2, R ₂ to R ₄ and Ar are the same as defined in Formula 3 above.

As another example, the compound of Formula 4 may be prepared according to the following reaction scheme. Each step in the scheme can utilize reaction conditions and materials known in the art. In Reaction Scheme 3 below, reactants and reaction conditions may be substituted, if necessary, with those known in the art.

[Reaction Scheme 3]

In the above Reaction Scheme 3, R ₁ , R ₃ , R ₄ and Ar are the same as defined in Formula 4 above.

Another embodiment of the present invention provides an organic light emitting device comprising the compound of Formula 1 described above. Specifically, the organic light emitting device according to the present invention includes a cathode, a cathode, and at least one organic layer provided between the anode and the cathode, and at least one of the organic layers includes a compound represented by the formula (1).

FIGS. 1 to 3 illustrate the stacking process of the electrodes and organic layers of the organic light emitting diode according to the embodiments of the present invention. However, the scope of the present invention is not intended to be limited by these drawings, and the structure of the organic light emitting device known in the art can be applied to the present invention.

1, an organic light emitting device in which an anode 200, an organic layer 300, and a cathode 400 are sequentially stacked on a substrate 100 is shown. However, the present invention is not limited to such a structure, and an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented as shown in FIG.

FIG. 3 illustrates the case where the organic material layer is a multilayer. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, a hole blocking layer 304, an electron transport layer 305 and an electron injection layer 306. However, the scope of the present invention is not limited by such a laminated structure, and other layers other than the light emitting layer may be omitted as necessary, and other necessary functional layers may be added.

The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer contains the compound of Formula 1.

The compound of formula (I) may constitute one or more layers of the organic material layer of the organic light emitting device. However, if necessary, the organic material layer may be formed by mixing with other materials.

The compound of Formula 1 may be used as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material in an organic light emitting device. The compound of Formula 1 may be used as a material of a light emitting layer of an organic light emitting device. Specifically, the compound of Formula 1 may be used as a single luminescent material in the luminescent layer, or as a host material or a dopant material in the luminescent layer. In addition, the compound can be used as a hole transporting layer material of an organic light emitting device.

In the organic light emitting device according to the present invention, materials other than the compound of Formula 1 are exemplified below, but they are for illustrative purposes only and are not intended to limit the scope of the present invention. Materials known in the art Can be replaced.

As the cathode material, materials having a relatively large work function can be used, and a transparent conductive oxide, a metal, or a conductive polymer can be used.

As the cathode material, materials having relatively low work functions can be used, and metals, metal oxides, conductive polymers, and the like can be used.

As the hole injecting material, a known hole injecting material may be used. For example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or a compound described in Advanced Material, 6, p. 677 (1994) PANDOT / PSS (Polyaniline / Dodecylbenzenesulfonic acid), which is a soluble conductive polymer such as TCA, m-MTDATA, m-MTDAPB, 4-ethylenedioxythiophene / poly (4-styrenesulfonate) / poly (4-styrene sulfonate) / Pani / CSA (polyaniline / camphor sulfonic acid) PANI / PSS (polyaniline) / poly (4-styrene-sulfonate): polyaniline) / poly (4-styrenesulfonate)).

As the hole transporting material, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, or the like may be used, and a low molecular weight or a high molecular weight material may be used.

Examples of the electron transporting material include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, Derivatives thereof, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, and the like may be used as well as low molecular weight materials and high molecular weight materials.

As the electron injecting material, for example, LiF is typically used in the art, but the present invention is not limited thereto.

As the light emitting material, red, green or blue light emitting materials may be used, and if necessary, two or more light emitting materials may be mixed and used. Further, a fluorescent material may be used as a light emitting material, but it may be used as a phosphorescent material. As the light emitting material, a material which emits light by coupling holes and electrons respectively injected from the anode and the cathode may be used. However, materials in which both the host material and the dopant material participate in light emission may also be used. As a specific example, the compound according to the present invention can be used as a phosphorescent host material. At this time, as the phosphorescent dopant material, a dopant material having a light emission characteristic of green series may be used.

When the compound according to the present invention is used as a phosphorescent host material, phosphorescent dopant materials used together can be those known in the art.

For example, phosphorescent dopant materials represented by LL'MX, LL'L "M, LMXX ', L ₂ MX and L ₃ M can be used, but the scope of the present invention is not limited by these examples.

Here, L, L ', L ", X and X' are two different left ligands and M is a metal forming an octahedral complex.

M may be iridium, platinum, osmium, and the like.

L is sp ² An anionic bidentate ligand that is coordinated to M by carbon and hetero atoms, and X can function to trap electrons or holes. Non-limiting examples of L include 2- (1-naphthyl) benzoxazole, (2-phenylbenzoxazole), (2-phenylbenzothiazole), (2-phenylbenzothiazole) -Benzoquinoline), (thienylpyridine), phenylpyridine, benzothienylpyridine, 3-methoxy-2-phenylpyridine, thienylpyridine, tolylpyridine and the like. Non-limiting examples of X include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, and the like.

More specific examples are shown below, but are not limited to these examples.

EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Examples. However, the present invention is not intended to limit the scope of the present invention.

[Preparation Example 1] Preparation of Compound 1

compound 1-1 Manufacturing

1-Bromo-2-iodobenzene (5.66 g, 20 mmol) was dissolved in THF (15 ml) and triethylamine (15 ml) under nitrogen. Ethynyltrimethylsilane (2.16 g, 20 mmol), PdCl ₂ (PPh ₃ ) ₂ (70 mg, 0.5 mol%) and CuI (38 mg, 1 mol%) were added and stirred at room temperature. After completion of the reaction, the reaction mixture was diluted with diethyl ether and washed with brine. The water was removed using Na ₂ SO ₄ , and then purified through silica gel. 5 g of the aimed compound was obtained (yield> 99%).

compound 1-2 Manufacturing

ZrCp ₂ Cl ₂ (3.21 g, 11 mmol) was added to the toluene solvent, and the mixture was cooled to 0 ° C. PhLi (11 ml, 22 mol, 2M diethyl ether solution) was added dropwise and stirred for 2 hours. Compound 1-1 was added dropwise at the same temperature, and the mixture was heated to 100 DEG C and stirred for 12 hours (proceeded to the next step without purification).

compound 1-3 Manufacturing

The compound 1-2 solution was cooled to 0 캜, iodine (10.16 g, 40 mmol) and CuCl (2.08 g, 21 mmol) were added thereto, followed by stirring for 12 hours. After the reaction was completed, a saturated aqueous solution of Na ₂ S ₂ O ₃ was made and the water was removed using Na ₂ SO ₄ . The residue was purified by silica gel (silica gel) to obtain 5.4 g of the desired compound 1-3 (yield:> 93%).

compound 1-4 Manufacturing

Compounds 1-3 were diluted with toluene under nitrogen conditions. After adding Pd (OAc) ₂ (5 mol%), Xanthphos (10 mol%), Cs ₂ CO ₃ ( ₂ mmol) and aniline (1.2 mmol) Respectively. When the reaction was complete, the reaction mixture was diluted with diethyl ether, washed with water and brine, and dehydrated with Na ₂ SO ₄ . The target compound 1-4 was obtained in a yield of 80% using a silica gel column.

compound 1-5 Manufacturing

Compounds 1-4 were diluted with toluene under nitrogen conditions. [PdCl (- allyl)] ₂ in (2.5 ㏖%) and _{P t -Bu 3 (10 ㏖%} ), LiOt-Bu (0.9 m㏖) and 120 ℃ was placed 4-nitro-benzaldehyde (0.3 m㏖) 10 Lt; / RTI > When the reaction was complete, the reaction mixture was diluted with diethyl ether, washed with water and brine, and dehydrated with Na ₂ SO ₄ . Silica gel column was carried out to obtain the desired compound 1-5 in a yield of 70%.

compound 1-6 Manufacturing

Compound 1-5 was diluted with CH ₂ Cl ₂ under nitrogen. NBS (2.5 mol) was added thereto, followed by stirring at room temperature for 24 hours. When the reaction was completed, the reaction mixture was filtered using CH ₂ Cl _2, and the organic solvent layer was dehydrated with Na ₂ SO ₄ . Silica gel column was carried out to obtain desired compound 1-6 in a yield of 60%.

compound One Manufacturing

Compounds 1-6 were diluted with DMF under nitrogen conditions. Pd (PPh ₃ ) ₄ (2.5 mol%), K ₂ CO ₃ ( ₃ mol) and phenyl boronic acid (1.2 mol) were charged and the mixture was heated and stirred at 120 ° C. for 10 hours. When the reaction was complete, the reaction mixture was diluted with diethyl ether, washed with water and brine, and dehydrated with Na ₂ SO ₄ . Silica gel column was carried out to obtain desired compound 1 in a yield of 70%.

[Preparation Example 2] Preparation of Compound 2

Compound 1 was prepared in the same manner except that 2-naphthaleneboronic acid was used instead of phenylboronic acid.

[Preparation Example 3] Preparation of Compound 10

In the same manner as in the preparation of Compound 1 except that p-fluorobenzylboronic acid was used instead of phenylboronic acid.

[Preparation Example 4] Preparation of Compound 11

(B-9H-carbazol-9-yl-boronic acid) was used instead of phenylboronic acid in the preparation of Compound 1.

[Preparation Example 5] Preparation of Compound 14

Except that 9,9-dimethylfluoren-2-ylboronic acid was used instead of phenylboronic acid in the preparation of Compound 1.

[Preparation Example 6] Preparation of Compound 16

compound 16-1 Manufacturing

1-bromo-4-chloro-2-iodobenzene (6.3 g, 20 mmol) was dissolved in THF (20 ml) and triethylamine under nitrogen atmosphere. (20 ml). Ethynyltrimethylsilane (2.16 g, 20 mmol), PdCl ₂ (PPh ₃ ) ₂ (70 mg, 0.5 mol%) and CuI (38 mg, 1 mol%) were added and stirred at room temperature. After completion of the reaction, the reaction mixture was diluted with diethyl ether and washed with brine. The water was removed using Na ₂ SO ₄ , and then purified through silica gel. 5.5 g of the desired compound 16-1 was obtained (yield> 99%).

compound 16-2 Manufacturing

ZrCp ₂ Cl ₂ (3.21 g, 11 mmol) was added to the toluene solvent, and the mixture was cooled to 0 ° C. PhLi (11 ml, 22 mol, 2M diethyl ether solution) was added dropwise and stirred for 2 hours. Compound 16-1 was added dropwise at the same temperature, and the mixture was heated to 100 DEG C and stirred for 12 hours (proceeded to the next step without purification).

compound 16-3 Manufacturing

The solution of Compound 16-2 was cooled to 0 占 폚, iodine (10.16 g, 40 mmol) and CuCl (2.08 g, 21 mmol) were added thereto, followed by stirring for 12 hours. After the reaction was completed, a saturated aqueous solution of Na ₂ S ₂ O ₃ was made and the water was removed using Na ₂ SO ₄ . The residue was purified by silica gel (silica gel) to obtain 5.4 g of the target compound 16-3 (yield:> 93%).

compound 16-4 Manufacturing

Compound 16-3 was diluted with toluene under nitrogen conditions. After adding Pd (OAc) ₂ (5 mol%), Xanthphos (10 mol%), Cs ₂ CO ₃ ( ₂ mmol) and aniline (1.2 mmol) Respectively. When the reaction was complete, the reaction mixture was diluted with diethyl ether, washed with water and brine, and dehydrated with Na ₂ SO ₄ . The target compound 16-4 was obtained in a yield of 80% using a silica gel column.

compound 16-5 Manufacturing

Compound 16-4 was diluted with toluene under nitrogen conditions. [PdCl (- allyl)] ₂ in (2.5 ㏖%) and _{P t -Bu 3 (10 ㏖%} ), LiOt-Bu (0.9 m㏖) and 120 ℃ was placed 4-nitro-benzaldehyde (0.3 m㏖) 10 Lt; / RTI > When the reaction was complete, the reaction mixture was diluted with diethyl ether, washed with water and brine, and dehydrated with Na ₂ SO ₄ . Silica gel column was carried out to obtain desired compound 16-5 in a yield of 70%.

compound 16 Manufacturing

Compound 16-5 was diluted with THF / H2O under nitrogen conditions. Pd (PPh ₃ ) ₄ (2.5 mol%), K ₂ CO ₃ ( ₃ mol) and naphthyl boronic acid (1.2 mol) were charged and the mixture was heated and stirred at 120 ° C. for 10 hours. When the reaction was complete, the reaction mixture was diluted with diethyl ether, washed with water and brine, and dehydrated with Na ₂ SO ₄ . Silica gel column was carried out to obtain desired compound 16 in 70% yield.

[Preparation Example 7] Preparation of Compound 22

In the preparation of Compound 16-4 of Preparation Example 6, the same 9-aminoanthracene was used instead of aniline, and the same pyridine-3-ylboronic acid was used instead of naphthylboronic acid in the preparation of Compound 16 ≪ / RTI >

[Preparation Example 8] Preparation of Compound 27

The same procedure was followed except that naphthalen-2-amine was used instead of aniline in the preparation of the compound 1-4 of Preparation Example 1.

[Preparation Example 9] Preparation of Compound 41

In the preparation of Compound 16-4 of Preparation Example 6, phenazin-1-amine was used instead of aniline and phenylboronic acid was used in place of naphthylboronic acid in the preparation of Compound 16 Were prepared in the same manner.

[Preparation Example 10] Preparation of Compound 42

Was prepared by the same method except that naphthalen-2-amine was used in place of aniline in the preparation of compound 16-4 of Preparation Example 6.

[Preparation Example 11] Preparation of Compound 57

(Pyridin-2-amine) instead of aniline and phenanthrenylboronic acid instead of phenylboronic acid in the preparation of Compound 1 of Preparation Example 1 in the production of the compound 1-4 of Preparation Example 1, . ≪ / RTI >

[Preparation Example 12] Preparation of Compound 67

Except that pyridine-2-amine was used instead of aniline and phenylboronic acid was used in place of naphthylboronic acid in the preparation of compound 16 in the preparation of compound 16-4 of Preparation Example 6 Were prepared in the same manner.

[Preparation Example 13] Preparation of Compound 79

In the preparation of Compound 1 of Preparation Example 1, 4,6-diphenyl-1,3,5-triazin-2-amine (4,6-diphenyl- ) Were used as the starting materials.

[Preparation Example 14] Preparation of Compound 105

compound 105-1 Manufacturing

After Fig. 2-Bromo-Moai dissolved in benzene (9.2g, 32.5m㏖) in THF (50㎖), TMS- acetylene (4.8㎖, 1.05 _{equiv.), Pd (PPh 3) 2} Cl 2 (1.1g, 0.05 equiv) And CuI (0.3 g, 0.05 eq.). After stirring at room temperature for 10 minutes, triethylamine (10 ml, 2.0 equivalents) was slowly added dropwise and stirred at the same temperature for 1 hour. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and purified water and subjected to column purification to obtain Compound 105-1 in 97% yield.

compound 105-2 Manufacturing

ZrCp ₂ Cl ₂ (1.25 eq) was dissolved in toluene and cooled to 0 ° C. After phenyllithium (2.5 eq.) Was slowly added dropwise, the mixture was stirred at room temperature for 2 hours. Thereafter, Compound 105-1 (8 g, 31.6 mmol) was added and refluxed. After 5 hours, the mixture was cooled to room temperature, and CuCl (2.3 equivalents) and iodine (4.0 equivalents) were added thereto, followed by stirring at room temperature for 10 hours. After the reaction was completed, the reaction mixture was extracted with n-hexane and Na ₂ S ₂ O ₃ aqueous solution. The organic layer was dehydrated using Na ₂ SO ₃ and crystallized with n-hexane to obtain compound 105-2 in 60% yield.

compound 105-3 Manufacturing

Compound 105-2 (11g, 18.9m㏖) was dissolved in toluene (50㎖), 4- chloroaniline (1.3 eq), Pd (OAc) ₂ (0.05 eq.), Glass monohydrate (0.1 equiv), and Cs ₂ CO ₃ (2.0 eq.) Was added and refluxed. The mixture was refluxed for 12 hours, cooled to room temperature, extracted with diethyl ether and ammonium chloride, and then the organic layer was concentrated. Thereafter, column purification was conducted to obtain Compound 105-3 in 76% yield.

compound 105-4 Manufacturing

PdCl (allyl)] ₂ (0.06 eq.), P (t-Bu) ₃ (0.1 eq.), 4- nitrobenzene Aldehyde (0.9 eq.), And LiOt-Bu (3.0 eq.) Were charged and refluxed for 12 hours. Upon completion of the reaction, the reaction mixture was cooled to room temperature and immediately concentrated to a silica column to obtain Compound 105-4 in an 80% yield.

compound 105-5 Manufacturing

Compound 105-4 (4 g, 11.1 mmol) was dissolved in 1,4-dioxane and then Pd ₂ (dba) ₃ (0.1 eq.), Zanphor (0.03 eq.) And Pinacole diborane ), And KOAc (3.0 eq.) Were added and refluxed. After 2 hours, the reaction mixture was cooled to room temperature and extracted with ethyl acetate and purified water. The organic layer was purified by silica column to obtain Compound 105-5 in 85% yield.

compound 105 Manufacturing

Compound 105-5 (4 g, 8.86 mmol) was dissolved in THF (20 ml) and purified water (2 ml), 2-chloro-4,6-diphenyl-1,3,5-triazine (1.5 eq.), Pd (PPh _{3) 4} (0.05 eq), and K ₂ CO ₃ was added (3.0 eq.) was refluxed for 3 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and subjected to a first purification step through a silica column. The solid thus obtained was recrystallized using ethyl acetate to obtain Compound 105 in 90% yield.

The compound was prepared in the same manner as in the above Synthesis Experimental Example, and the results of confirmation of the synthesis are shown in Table 1.

Compound No. Found calculated One (1H, d), 7.86 (1H, d), 7.82-7.75 (3H, m), 7.58-7.41 477.67 477.19 2 (1H, d), 8.26 (1H, dd), 8.00-7.88 (7H, m), 7.82-7.73 (5H, m), 7.59-7.45 577.79 577.22 8 (1H, dd), 7.68 (2H, dd), 8.50 (2H, dd), 8.39 (1H, s), 8.33 M), 7.00 (2 H, dd), 066 (6 H, s) 555.74 555.21 10 (1H, m), 8.27 (1H, dd), 7.88 (1H, d), 7.82-7.75 (3H, m), 7.58-7.50 (4H, m), 7.49-7.39 0.66 (6 H, s) 513.65 513.17 11 (2H, dd), 7.94 (1H, dd), 7.71 (2H, s), 7.63-7.45 (1H, m), 7.33-7.24 s) 655.86 655.24 14 M), 7.85-7.75 (5H, m), 7.63-7.55 (6H, m), 7.54-7.38 (5H, m), 8.27 (1H, dd) 7.30-7.28 (3H, m), 1.72 (12H, s), 0.66 (6H, s) 709.99 709.32 15 (2H, m), 7.52-7.50 (4H, m), 7.45-7.40 (5H, m), 7.30-7.88 7.30 (1 H, d), 0.66 (6 H, s) 501.69 501.19 16 M), 7.59-7.58 (5H, m), 7.56-7.45 (5H, m), 7.75-7.88 (2H, m), 8.17 (1H, dd), 8.05-7.95 ), 7.30 (1 H, d), 0.66 (6 H, s) 451.63 451.18 19 (7H, m), 7.58-7.42 (7H, m), 7.30 (1H, d), 8.99 1H, s), 0.66 (6H, s) 501.69 501.19 22 (1H, d), 7.90-7.88 (5H, m), 7.75-7.71 (2H, m), 8.32 (1H, d) m), 7.57 (1H, dd), 7.44-7.42 (6H, m), 7.30 502.68 502.19 25 (2H, m), 7.98 (1H, m), 7.88-7.41 (2H, m), 8.80-8.17 7.51-7.42 (6 H, m), 7.30 (1 H, d), 0.66 (6 H, s) 507.72 507.15 27 (2H, m), 7.81-7.82 (2H, m), 7.75 (1H, dd) 7.36 (6 H, m), 7.30 (1 H, d), 0.66 (6 H, s) 527.73 527.21 29 (2H, dd), 8.27 (1H, dd), 8.08-8.00 (7H, m), 7.88 (1H, d), 7.83 (1H, d), 7.82-7.75 m), 7.61-7.55 (8H, m), 7.36 (1H, dd), 7.30 627.85 627.24 32 D), 8.93 (1H, d), 8.34 (1H, m), 7.81-7.71 (6H, m), 7.59 (2H, dd), 7.36 727.96 727.27 33 (2H, d), 8.27 (2H, td), 8.21 (1H, d), 8.12 (1H, d), 8.04-8.00 (5H, m), 7.92-7.82 (4H, m), 7.81-7.75 (1H, m), 7.59 (2H, d), 7.49-7.42 729.94 729.26 34 D), 8.23 (1H, dd), 8.00-7.95 (3H, m), 7.83 (1H, d) , 7.80 (1H, d), 7.59-7.51 (4H, m), 7.36-7.26 529.71 529.20 35 (2H, d), 8.42 (2H, d), 8.27 (1H, d), 8.00-7.95 (3H, m), 7.88 (1H, s), 7.83-7.82 m), 7.77-7.75 (2H, m), 7.59-7.57 (4H, m), 7.36 529.71 529.20 36 D), 7.77-7.75 (2H, m), 7.60-7.55 (4H, m), 7.39-7. 7.30 (9H, m), 0.66 (6H, s) 563.71 563.19 41 (2H, d), 7.41-7.41 (3H, m), 7.30-7.28 (2H, 2H, m), 0.66 (6H, s) 503.67 503.18 42 (1H, m), 8.17 (1H, m), 8.00-7.92 (6H, m), 7.88-7.83 (2H, m), 7.75-7.71 (3H, m), 7.59-7.58 7.36 (1H, d), 7.30 (1H, d), 0.66 (6H, s) 501.69 501.19 43 M), 7.61-7.88 (2H, m), 7.78-7.71 (3H, m), 7.61-7.88 M), 7.42 (2H, m), 7.30 (1H, d), 0.66 (6H, s) 502.68 502.19 44 (2H, d), 8.93 (2H, dd), 8.17-8.12 (2H, m), 8.10-8.00 (3H, m), 7.93-7.82 (7H, m), 7.75-7.71 7.42 (2H, m), 7.36 (1H.d), 7.30 (1H.d), 0.66 (6H, s) 551.75 551.21 47 Dd), 8.17 (1H, dd), 8.05-7.95 (3H, m), 7.83 (IH, t), 7.71 (IH, dd), 8.36 , 7.59 (2H, dd), 7.51 (1H, dd), 7.42 (2H, dd), 7.36-7.26 452.62 452.17 48 Dd), 7.91 (1H, d), 8.02 (1H, dd) , 7.88 (2H, dd), 7.75-7.71 (2H, m), 7.60-7.57 (2H, m), 7.42 453.61 453.17 49 (2H, m), 7.63 (1H, td), 7.49 (1H, dd), 7.92-7.88 6H, m), 7.35-7.25 (3H, m), 0.66 (6H, s) 470.61 470.16 51 (1H, d), 7.75-7.71 (2H, m), 7.85-7.17 (2H, m) 7.59-7.52 (4H, m), 7.50-7.36 (4H, m), 7.30 (1H, d), 0.66 557.78 557.16 53 (1H, d), 8.41 (1H, dd), 8.27 (1H, dd), 8.10-8.00 (1H, m), 7.90-7.88 7.45 (10H, m), 7.41-7.40 (3H, m), 7.30 (1H, d), 0.66 (6H, s) 478.66 478.19 54 (1H, dd), 7.77-7.73 (4H, m), 7.59-7.88 (4H, m) 7.58 (6H, m), 7.40 (1H, td), 7.30 (1H, d), 0.66 578.78 578.22 57 (8H, m), 7.58 (2H, dd), 7.93 (2H, d) , 7.50 (2H, d), 7.45 (1H, d), 7.30 (1H, d) 677.25 677.91 62 (2H, m), 7.40-7.88 (2H, m), 8.41 (1H, dd), 8.27 (1H, dd), 8.05-7.95 7.39 (5H, m), 7.35-7.25 (5H, m), 0.66 (6H, s) 514.64 514.17 64 (2H, m), 7.82-7.75 (3H, m), 8.45-8.41 (5H, m), 8.27 (1, dd), 8.20 D), 0.66 (6H, s), 7.50-7.50 (6H, m), 7.40 690.95 690.16 67 (1H, d), 8.17 (1H, dd), 8.05-7.95 (1H, m), 7.90-7.88 (2H, m), 7.75-7.71 (3H, m), 7.59-7.58 7.42-7.40 (3 H, m), 7.30 (1 H, d), 0.66 (6 H, s) 402.56 402.16 68 M), 8.41 (1H, dd), 8.17 (1H, dd), 8.01-8.00 (3H, m), 7.92-7.90 (3H, m), 7.75-7.71 (3H, m), 7.59-7.58 7.42-7.40 (3 H, m), 7.30 (1 H, d), 0.66 (6 H, s) 452.62 452.17 74 (2H, m), 8.19-8.10 (1 H, m), 8.05-7.95 (1 H, m), 7.90-7.88 (2 H, m), 8.42-8.41 (2H, m), 7.57 (1H, dd), 7.42-7.40 (3H, m), 7.30 403.55 403.15 76 Dd), 8.01 (1H, dd), 8.01-7.90 (3H, m), 7.71 (1H, dd) , 7.58-7.50 (3H, m), 7.42-7.24 (7H, m), 0.66 (6H, s) 491.66 491.18 79 (2H, m), 7.30 (1H, d), 7.66-7.75 (2H, m) 6H, s) 632.83 632.24 80 (8H, m), 7.55-7.37 (10H, m), 0.66 (2H, dd), 8.27 (1H, dd) 3H, s) 639.86 639.24 84 (1H, d), 8.18-8.04 (4H, m), 7.88-7.77 (8H, m), 7.71 (4H, m), 7.58-7.37 (11H, m), 0.66 (3H, s) 739.97 739.27 86 (2H, d), 7.00 (2H, d), 7.80-7.37 (1H, dd), 0.66 (3 H, s) 541.72 541.20 89 (8H, m), 7.52-7.45 (8H, m), 7.37-7.25 (2H, d) 9H, m), 0.66 (3H, s) 717.93 717.26 93 (1H, dd), 7.80 (1H, dd), 7.80 (1H, dd) s) 463.64 463.18 100 (1H, s), 7.71 (1H, dd), 7.58 (1H, d) -7.50 (7H, m), 7.45-7.37 (7H, m), 0.66 (3H, s) 464.63 464.17 105 (2H, d), 7.87-7.6 (7H, m), 7.52 (1H, d) , 7.46 (1H, t), 7.35-7.28 (2H, m), 7.18 (1H, t)
0.46 (6H, s) 556.73 556.21

Test Example  1: Characterization of Compound 105

The HOMO, LUMO and BAND GAP of Compound 105 were measured by the following method using a CV measuring instrument (manufacturer: princeton appied research (model: Parstat 2273)) and the results are shown in Table 3 below .

1. Preparation of Electrolyte Solution, Standard Solution, and Test Solution

1) Electrolyte solution: 3.3 g of tetrabutylammonium tetrafluoroborate was precisely weighed into a 100 ml volumetric flask and methylene chloride was added to make 100 ml.

2) Standard solution: Approximately 1 mg of NPB was precisely weighed, placed in a 10-ml volumetric flask, and the electrolyte solution was added to make 10 ml and used as a standard solution.

3) Test solution: Approximately 1 mg of the compound was precisely weighed into a 10-mL volumetric flask, and the electrolyte solution was added to make 10 mL and used as the sample solution.

2. Analysis conditions

Parameter Value Reference electrode type
(Reference Electrode type) Ag. AgCl / NaCl (sat'd) Initial Potential (E0) 0.00 Volts Vertex Potential (E1) 1.5 to 2.5 Volts Final Potential (E2) 0.00 Volts Scan rate (Scan rate) 50-100 Volts

3. CV measurement method

1) 6 ml of standard solution was prepared using NPB and electrolyte solution.

2) A working electrode, a reference electrode, and an auxiliary electrode were provided.

3) Measurement was started after nitrogen bubbling for about 30 seconds.

4) After completion of the measurement, the sample was cleanly washed with MC and acetone, and a sample solution of the compound to be measured was prepared and measured as described above.

4. Calculations

Homo = -5.5- (E _ox (compound to be measured) - E _ox (NPB)) eV

Band gap (Homo-rumo) = 1240 / UV absorption edge

Homo = -5.5- (E _ox (Compound 105) -E _ox (NPB)) (eV)
Band gap = 1240 / UV absorption limit (426 nm) (eV) E _ox homo Band gap Rumo NPB 0.78 eV Compound 105 1.04eV -5.76 eV 2.91 eV -2.85 eV

Figs. 4 and 5 show E _ox values derived from the CV measurement of Compound 105. Fig.

4 and 5, the y-axis represents a current (unit: A) and the x-axis represents a potential (unit: V).

On the other hand, the T1 value of Compound 105 is shown in Table 4 below. The T1 value is derived from the low PL nmax value. Specifically, the T1 value was obtained by the equipment HITACHI-F7000, temperature -196 DEG C (77K), diluted solution 2-methyltetrahydrofuran, calculation formula [T1 (eV) = 1240 / PL shortest peak wavelength (nm)].

Compound 105 T1 2.36

On the other hand, FIG. 6 shows a UV measurement graph of Compound 105.

7 shows a PL measurement graph of Compound 105 at 254 nm.

8 is a graph showing the LTPL measurement of Compound 105 at 381 nm.

6 to 8 are intensity, and the x-axis is wavelength (unit: nm).

Example  One : OLED  Device fabrication

The transparent electrode ITO thin film obtained from the glass for OLED (manufactured by Samsung Corning) was subjected to ultrasonic cleaning using trichlorethylene, acetone, ethanol and distilled water sequentially, and then stored in isopropanol and used.

Next, an ITO substrate was placed on a substrate folder of a vacuum deposition equipment, and a cell in a vacuum deposition equipment was charged with 2-TNATA (4,4 ', 4 "-tris (N, N- (2- naphthyl) -phenylamino) amine).

Subsequently, the chamber was evacuated until the degree of vacuum reached 10 ^-6 torr, and then a current was applied to the cell to evaporate 2-TNATA, thereby depositing a 600 Å thick hole injection layer on the ITO substrate. NPB (N, N'-bis (? -Naphthyl) -N, N'-diphenyl-4,4'-diamine) was placed in another cell in a vacuum deposition apparatus, Lt; RTI ID = 0.0 > 300 A < / RTI >

After the hole injecting layer and the hole transporting layer were formed as described above, a phosphorescent green light emitting material having the following structure was deposited on the light emitting layer. The compound shown in Table 5, which is a green luminescent host material, was vacuum deposited on one cell in a vacuum deposition apparatus to a thickness of 350 Å, and a green light emitting dopant Ir (ppy) ₃ (Tris (2-phenylpyridine) iridium 10% vacuum deposition relative to the host material.

Then, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), which is a hole blocking layer material as described below, was deposited as a hole blocking layer to a thickness of 50 Å and Alq ₃ (8-hydroxy-quinolinato) aluminum was deposited to a thickness of 200 Å.

Thereafter, lithium fluoride (LiF) was deposited to a thickness of 10 Å as an electron injection layer. Then, an Al cathode was deposited to a thickness of 1000 Å to fabricate an OLED.

On the other hand, all the organic compounds required for OLED device fabrication were vacuum sublimated and refined under 10 ^-6 ~ 10 ^-8 torr for each material, and used for OLED fabrication.

Test Example  2: OLED Characterization of

The time from when the driving voltage Op.V and the power efficiency (cd / A) of the OLED device manufactured as described above is 1,000 cd / m ² until the efficiency drops to 50% is shown in Table 5 below.

Compound No. Op.V Cd / A T50 One 5.12 40.9 410 2 5.11 42.8 430 8 5.04 43.7 460 10 5.04 44.7 480 11 5.08 42.8 440 14 5.06 42.8 440 15 5.04 44.7 480 16 5.04 44.7 480 19 5.08 43.7 470 22 5.11 40.9 390 25 5.10 42.8 460 27 5.11 41.8 420 29 5.09 42.8 440 32 5.09 42.8 450 33 5.00 43.7 460 34 4.99 43.7 470 35 4.98 43.7 480 36 5.09 43.7 440 41 4.99 44.7 480 42 5.06 44.7 480 43 5.08 44.7 460 44 5.06 44.7 460 47 5.06 44.7 460 48 5.06 44.7 470 49 4.94 45.6 510 51 5.08 44.7 460 53 4.96 44.7 500 54 5.05 45.6 490 57 5.05 45.8 470 62 5.08 42.8 440 64 5.07 43.7 470 67 5.06 45.6 480 68 4.98 44.7 470 74 4.94 45.6 510 76 4.95 45.6 510 79 5.03 43.7 450 80 5.01 43.7 460 84 4.98 44.7 470 86 5.01 45.6 510 89 5.07 42.8 430 93 5.06 42.8 450 100 5.04 43.7 470 105 5.05 43.6 485 Comparative Example 1
CBP 6.71 36.1 370

From the results of Table 5, it was confirmed that the organic light emitting device manufactured using the compound of the present invention as a phosphorescent light emitting layer material had excellent characteristics in comparison with the organic light emitting device using CBP in the driving voltage, efficiency and lifetime. Accordingly, it has been confirmed that the compound represented by the formula (1) is useful as a material of a phosphorescent light emitting layer in the production of an organic light emitting device.

100: substrate
200: anode
300: organic layer
301: Hole injection layer
302: hole transport layer
303: light emitting layer
304: hole blocking layer
305: electron transport layer
306: electron injection layer
400: cathode

Claims (17)

A compound for a phosphorescent green light emitting layer of an organic light emitting device,
[Chemical Formula 1]

In Formula 1,
At least one of R ₁ and R ₂ is a C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; Or a C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl,
The remaining one of R ₁ and R ₂ is selected from the group consisting of hydrogen, a C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, and a C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl Selected,
R ₃ , R ₄ and Ar are the same or different and are each independently selected from the group consisting of hydrogen, halogen, C ₁ to C ₆₀ linear or branched substituted or unsubstituted alkyl, C ₂ to C ₆₀ linear or branched Substituted or unsubstituted alkenyl, C ₂ to C ₆₀ linear or branched substituted or unsubstituted alkynyl, C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl, C ₂ to C ₆₀ C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, and C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl ≪ / RTI >
n and m are each independently an integer of 0 to 4,
The term "substituted or unsubstituted" as used herein refers to a straight or branched C ₁ to C ₆₀ alkyl, C ₂ to C ₆₀ straight or branched chain alkenyl, C ₂ to C ₆₀ straight chain or branched C ₁ to C ₆₀ straight or branched chain haloalkyl, C ₂ to C ₆₀ linear or branched haloalkenyl, C ₂ to C ₆₀ linear or branched haloalkynyl, C ₁ to alkoxy linear or branched C _60, C ₂ to C ₆₀ straight chain or branched alkenyloxy, C ₂ to C ₆₀ linear or branched alkynyloxy, monocyclic the C ₃ to C ₆₀ or A C ₂ to C ₆₀ monocyclic or polycyclic heterocycloalkyl, a C ₆ to C ₆₀ monocyclic or polycyclic aryl, a C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl, a C ₆ to C ₆₀ monocyclic or polycyclic aryl a mono- oxy, and C ₂ to C ₆₀ or polycyclic consisting heteroaryloxy To 1 or more substituents selected from the means substituted or unsubstituted. The phosphorescent green light emitting layer compound of claim 1, wherein the compound represented by Formula 1 is represented by any one of Chemical Formulas 2 to 4:
(2)

(3)

[Chemical Formula 4]

In formulas (2) to (4), R ₁ to R ₄ and Ar are as defined in formula (1). The phosphorescent green light emitting layer compound of an organic electroluminescent device according to claim 1, wherein R ₁ and R ₂ are the same as each other. The phosphorescent green light emitting layer compound of an organic electroluminescent device according to claim 1, wherein R ₁ and R ₂ are different from each other. The phosphorescent green light emitting layer compound of an organic electroluminescent device according to claim 1, wherein R ₁ , R ₂ and Ar are the same as each other. The phosphorescent green light emitting layer compound of an organic electroluminescent device according to claim 1, wherein Ar is different from R ₁ or R ₂ . delete A compound according to claim 1, wherein R ₁ and R ₂ are the same or different and each independently represents a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthryl , Substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted phenanthridil, substituted or unsubstituted dibenzothiophene group, Lt; / RTI > is unsubstituted carbazolyl,
Wherein said " substituted or unsubstituted "is the same as defined in claim 1, for a phosphorescent green light emitting layer of an organic light emitting device. The compound according to claim 1, wherein R ₁ is hydrogen, R ₂ is C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, and C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl ≪ / RTI >
Wherein said " substituted or unsubstituted "is the same as defined in claim 1, for a phosphorescent green light emitting layer of an organic light emitting device. A compound according to claim 1, wherein R ₁ is hydrogen and R ₂ is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, Phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted phenanthridyl, substituted or unsubstituted dibenzothiophene groups, or substituted or unsubstituted carbazolyl groups ego,
Wherein said " substituted or unsubstituted "is the same as defined in claim 1, for a phosphorescent green light emitting layer of an organic light emitting device. The compound according to claim 1, wherein Ar is selected from the group consisting of C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl, and C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl,
Wherein said " substituted or unsubstituted "is the same as defined in claim 1, for a phosphorescent green light emitting layer of an organic light emitting device. Wherein Ar is phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthrenyl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl or phenazinyl, , Biphenyl, terphenyl, naphthyl, anthryl, phenanthrenyl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, or phenazinyl, Wherein the organic compound is one selected from the group consisting of phenyl, naphthyl, anthryl, phenanthrenyl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl or phenazinyl. delete The phosphorescent green light emitting layer compound of claim 1, wherein the compound of formula (1) is selected from the following structural formulas:

Wherein at least one of the organic layers includes an anode, a cathode, and at least one organic layer disposed between the anode and the cathode, wherein at least one of the organic layers is a phosphor of the organic light-emitting device according to any one of claims 1 to 6, 8 to 12, An organic light emitting device comprising a compound for a green light emitting layer. 16. The organic light emitting device according to claim 15, wherein the organic layer includes a light emitting layer containing the compound as a phosphorescent host. delete

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