KR101551895B1 - Polycyclic compound including pyrazole and organic light emitting device using the same - Google Patents

Abstract

The present invention relates to a pyrazole-containing polycyclic ring compound and an organic light-emitting device comprising the same.

Description

FIELD OF THE INVENTION [0001] The present invention relates to a pyrazole-containing polycyclic ring compound and an organic light emitting device using the same. BACKGROUND ART [0002] Polycyclic compound-

The present invention relates to a novel pyrazole-containing polycyclic ring 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, which then extinguishes and emits light. 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 needed. 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 pyrazole-containing polycyclic compound and an organic light-emitting device comprising the same.

The present invention provides compounds of formula 1:

[Chemical Formula 1]

In Formula 1,

R ₁ to R ₈ are the same or different and each independently 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 ₁ to C ₆₀ linear or branched, substituted or unsubstituted alkoxy; C ₆ to C ₆₀ straight or branched chain substituted or unsubstituted aryloxy; C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl; A C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; A substituted or unsubstituted C ₁₀ to C ₆₀ spiro group; C ₁ to C ₂₀ substituted or unsubstituted alkylamines; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted arylamine; And a monocyclic or polycyclic substituted or unsubstituted heteroarylamine of C ₂ to C ₆₀ , or at least two adjacent substituents of R ₁ to R ₈ are bonded to each other to form an aromatic hydrocarbon ring or a heterocycle .

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 described in this specification can be used as an organic 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 usefully used as a material for electron injection and / or transport layer of an organic light emitting device. In addition, the above compound can be used as a light emitting material. For example, the compound can be used as a phosphorescent host material.

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.
Figures 4 and 5 show the E _ox values derived from CV measurements of compound 38.
Figures 6 and 7 show the E _ox values derived from CV measurements of compound 66.
Figures 8 and 9 show the E _ox values derived from CV measurements of compound 76.
10 shows a UV measurement graph of compound 38. Fig.
11 shows a PL measurement graph of Compound 38 at 320 nm.
Figure 12 shows a UV measurement graph of compound 66.
13 shows a PL measurement graph of Compound 66 at 260 nm.
14 shows a UV measurement graph of Compound 76. Fig.
15 shows a PL measurement graph of Compound 76 at 303 nm.

Hereinafter, the present invention will be described in detail.

The compounds described in this specification can be represented by the above formula (1). Specifically, the compound of Formula 1 may be used as an organic material layer material of an organic light emitting diode according to the structural features of the core structure and the substituent.

In particular, the compound of Formula 1 has a HOMO / LUMO value suitable for electron injection or transport of an organic light emitting device, has excellent electron transporting ability by N-N bond, and is excellent in thermal stability.

Further, the compound of Formula 1 is suitable for use as a light emitting layer material, particularly, a phosphorescent host material of a light emitting layer. Where the T1 value can be derived from the low temperature PL nmax value. In the present specification, the T1 value is obtained by the equipment HITACHI-F7000, temperature -196 DEG C (77K), diluent 2-methyltetrahydrofuran, formula [T1 (eV) = 1240 / PL shortest peak wavelength . For example, a compound having a bipolar structure may be used as the host material of the light emitting layer of the organic light emitting device. When the condensed ring group of the N-containing ring and the S-containing ring is substituted in the core of the above formula (1), the condensed ring group includes both a donor and an acceptor. EML), it is possible to form an exciton. The band gap is affected when the heteroatoms N and S in the condensed ring group are in the same direction as those in the same direction. When N and S are in the same direction, the conjugation length of the π-electron is shortened. If N and S are in different directions, the conjugation length of the π-electron becomes longer and affects the T1 value.

As used herein, "substituted or unsubstituted" means a straight or branched chain alkyl of C ₁ to C ₆₀ ; C ₂ to C ₆₀ straight or branched chain alkenyl; C ₂ to C ₆₀ linear or branched alkynyl; C ₃ to C ₆₀ monocyclic or polycyclic cycloalkyl; A 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 heteroaryl; A C ₁₀ to C ₆₀ spiro group; C ₁ to C ₂₀ alkylamines; A C ₆ to C ₆₀ monocyclic or polycyclic arylamine; And monocyclic or polycyclic heteroarylamines of C ₂ to C _60. The term " substituted or unsubstituted " The additional substituents may be further substituted.

In the present specification, alkyl includes straight or 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 present specification, alkenyl includes straight 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 present specification, 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 the present specification, 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 present specification, heterocycloalkyl includes S, O, N or Si 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 the present specification, 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 25. Specific examples of aryl include phenyl, biphenyl, triphenyl, naphthyl, anthryl, klycenyl, phenanthrenyl, perylenyl, fluoranthenyl, triphenylenyl, phenalenyl, pyrenyl, tetracenyl, pentacenyl, Fluorenyl, indenyl, acenaphthylenyl, and condensed rings thereof, but are not limited thereto.

As used herein, heteroaryl includes S, O, N or Si as a heteroatom and includes monocyclic or polycyclic rings having 2 to 60 carbon atoms, which 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, more specifically 3 to 25 carbon atoms. Specific examples of heteroaryl include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furanyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, Thiadiazolyl, thiazolyl, tetrazolyl, pyrazinyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxinyl, triazinyl, tetrazinyl, quinolyl, isoquinolyl, Quinazolinyl, isoquinazolinyl, acridinyl, phenanthridinyl, imidazopyridinyl, diazanaphthalenyl, triazainene, indolyl, indolizinyl, benzothiazolyl, benzoxazolyl, But are not limited to, benzoimidazolyl, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazolyl, benzocarbazolyl, phenazinyl, and condensed rings thereof.

In the present specification, the spiro group is a group including a spiro structure and may have from 15 to 60 carbon atoms. For example, a spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro-bonded to a fluorene group. Specifically, the spiro group includes groups of the following structural formulas.

In this specification, the description of the above-mentioned aryl and heteroaryl, respectively, except that arylene and heteroarylene are divalent, can be applied.

In this specification, the description of the above-mentioned aryl and heteroaryl, respectively, except that the aromatic hydrocarbon and the aromatic heterocycle form a condensed ring, can be applied.

According to one embodiment of the present invention, at least one of R ₁ to R ₄ is a C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; Or a substituted or unsubstituted C ₁₀ to C ₆₀ spiro group, and the others are 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 ₁ to C ₆₀ linear or branched, substituted or unsubstituted alkoxy; C ₆ to C ₆₀ straight or branched chain substituted or unsubstituted aryloxy; C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl; A C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; A substituted or unsubstituted C ₁₀ to C ₆₀ spiro group; C ₁ to C ₂₀ substituted or unsubstituted alkylamines; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted arylamine; And a monocyclic or polycyclic substituted or unsubstituted heteroarylamine of C ₂ to C ₆₀ , or at least two adjacent substituents of R ₁ to R ₄ may be bonded to each other to form an aromatic hydrocarbon ring or a heterocycle .

According to one embodiment of the present invention, at least one of R ₁ to R ₄ is a C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; Or a substituted or unsubstituted C ₁₀ to C ₆₀ spiro group.

According to one embodiment of the present invention, one of R ₁ to R ₄ is a C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; Or a substituted or unsubstituted C ₁₀ to C ₆₀ spiro group.

According to one embodiment of the present invention, at least one of R ₁ to R ₄ is a C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; Or a substituted or unsubstituted C ₁₀ to C ₆₀ spiro group, and the rest of R ₁ to R ₄ is hydrogen or combined with an adjacent substituent to form an aromatic hydrocarbon ring or a heterocyclic ring.

According to one embodiment of the present invention, at least one of R ₁ to R ₄ 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, and the rest of R ₁ to R ₄ is hydrogen or combined with an adjacent substituent to form an aromatic hydrocarbon ring or a heterocyclic ring.

According to one embodiment of the present invention, 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.

According to one embodiment of the present invention, 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, and R ₁ , R ₃ and R ₄ are hydrogen.

According to one embodiment of the present invention, 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, R ₁ is hydrogen, and R ₃ and R ₄ are bonded to each other to form a substituted or unsubstituted benzene ring.

According to one embodiment of the present invention, R ₂ is selected from substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted thiazinyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenan Trityl, substituted or unsubstituted naphthyl, or substituted or unsubstituted phenyl group.

According to one embodiment of the present invention, R ₂ is selected from substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted thiazinyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenan Naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted phenyl groups. At least one of which may further be substituted with at least one of phenyl, naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl, quinolyl and isoquinolyl.

For example, R ₂ is further selected from the group consisting of phenyl, naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, pyridyl substituted phenyl, pyrimidyl substituted phenyl, Phenyl substituted anthryl, phenyl substituted phenanthryl, naphthyl substituted anthryl, naphthyl substituted anthryl, phenyl substituted naphthyl, substituted naphthyl substituted anthryl, substituted naphthyl substituted anthryl, Naphthyl substituted pyridyl, anthryl substituted pyridyl or phenanthryl substituted pyridyl, phenyl substituted pyrimidyl, naphthyl substituted pyrimidyl, anthryl substituted pyrimidyl, phenanthryl substituted pyrimidyl, phenanthryl substituted pyridyl, , Phenyl-substituted triazinyl, naphthyl-substituted triazinyl, anthryl-substituted triazinyl, or phenanthryl-substituted triazinyl, and the like.

According to one embodiment of the present invention, R ₄ 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.

According to one embodiment of the present invention, R ₄ 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, and R ₁ to R ₃ are hydrogen.

According to one embodiment of the present invention, R ₄ 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, R ₃ is hydrogen, and R ₁ and R ₂ are bonded to each other to form a substituted or unsubstituted benzene ring.

According to one embodiment of the present invention, R ₄ is selected from substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted thiazinyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenan Trityl, substituted or unsubstituted naphthyl, or substituted or unsubstituted phenyl group.

According to one embodiment of the present invention, R ₄ is selected from substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted thiazinyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenan Naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted phenyl groups. At least one of which may further be substituted with at least one of phenyl, naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl, quinolyl and isoquinolyl.

For example, R < ₄ > is further selected from the group consisting of phenyl, naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, Phenyl substituted anthryl, phenyl substituted phenanthryl, naphthyl substituted anthryl, naphthyl substituted anthryl, phenyl substituted naphthyl, substituted naphthyl substituted anthryl, substituted naphthyl substituted anthryl, Naphthyl substituted pyridyl, anthryl substituted pyridyl or phenanthryl substituted pyridyl, phenyl substituted pyrimidyl, naphthyl substituted pyrimidyl, anthryl substituted pyrimidyl, phenanthryl substituted pyrimidyl, phenanthryl substituted pyridyl, , Phenyl-substituted triazinyl, naphthyl-substituted triazinyl, anthryl-substituted triazinyl, or phenanthryl-substituted triazinyl, and the like.

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

According to one embodiment of the present invention, R ₁ 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, and R ₂ to R ₄ are hydrogen.

According to one embodiment of the present invention, R ₁ 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, R ₂ is hydrogen, and R ₃ and R ₄ are bonded to each other to form a substituted or unsubstituted benzene ring.

According to one embodiment of the present invention, R ₁ is selected from substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted thiazinyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenan Trityl, substituted or unsubstituted naphthyl, or substituted or unsubstituted phenyl group.

According to one embodiment of the present invention, R ₁ is selected from substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted thiazinyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenan Naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted phenyl groups. At least one of which may further be substituted with at least one of phenyl, naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl, quinolyl and isoquinolyl.

For example, R < ₁ > is further selected from the group consisting of phenyl, naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, Phenyl substituted anthryl, phenyl substituted phenanthryl, naphthyl substituted anthryl, naphthyl substituted anthryl, phenyl substituted naphthyl, substituted naphthyl substituted anthryl, substituted naphthyl substituted anthryl, Naphthyl substituted pyridyl, anthryl substituted pyridyl or phenanthryl substituted pyridyl, phenyl substituted pyrimidyl, naphthyl substituted pyrimidyl, anthryl substituted pyrimidyl, phenanthryl substituted pyrimidyl, phenanthryl substituted pyridyl, , Phenyl-substituted triazinyl, naphthyl-substituted triazinyl, anthryl-substituted triazinyl, or phenanthryl-substituted triazinyl, and the like.

According to one embodiment of the present invention, R ₁ and R ₂ are bonded to each other to form a substituted or unsubstituted benzene ring.

According to one embodiment of the present invention, R ₂ and R ₃ are bonded to each other to form a substituted or unsubstituted benzene ring.

According to one embodiment of the present invention, R ₃ and R ₄ are bonded to each other to form a substituted or unsubstituted benzene ring.

According to one embodiment of the present invention, R ₅ to R ₈ are the same or different from each other, and each independently 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 ₁ to C ₆₀ linear or branched, substituted or unsubstituted alkoxy; C ₆ to C ₆₀ straight or branched chain substituted or unsubstituted aryloxy; C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl; A C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; A substituted or unsubstituted C ₁₀ to C ₆₀ spiro group; C ₁ to C ₂₀ substituted or unsubstituted alkylamines; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted arylamine; And C ₂ to C ₆₀ mono- or polycyclic substituted or unsubstituted heteroaryl amines.

According to one embodiment of the present invention, R ₅ to R ₈ are the same or different from each other, and each independently hydrogen; 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; A C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroaryl; And a substituted or unsubstituted C ₁₀ to C ₆₀ spiro group.

According to one embodiment of the present invention, R ₅ to R ₈ are the same or different from each other, and each independently hydrogen; C ₁ to C ₆₀ linear or branched, substituted or unsubstituted alkyl; And C ₆ to C ₆₀ mono- or polycyclic substituted or unsubstituted aryl.

According to one embodiment of the present invention, R ₅ to R ₈ are hydrogen.

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

(2)

(3)

[Chemical Formula 4]

In the above formulas, R ₁ to R ₈ are as defined in formula (1)

R is as defined for R ₁ to R ₈ , u is an integer of 1 to 4,

When u is 2 or more, Rs are the same or different from each other.

According to one embodiment of the present invention, the formula (1) may be represented by one of the following formulas (5) to (8).

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

In the above formulas, R ₅ to R ₈ are as defined in formula (1)

R is as defined for R ₁ to R ₄ ,

n is an integer of 1 to 3, v is an integer of 1 to 5, and when n or v is 2 or more, Rs are the same or different from each other,

L is a C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted arylene; Or a C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroarylene, p and x are each an integer of 0 to 3, and when p or x is 2 or more, L is the same or different from each other,

Ar 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, q and y are each an integer of 0 to 3, and when q or y is 2 or more, Ar is the same or different from each other.

According to one embodiment of the present invention, in Formulas 5 to 8, L represents a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted triazine group, a substituted or unsubstituted anthracene group , A substituted or unsubstituted phenanthrene group, a substituted or unsubstituted naphthalene group, or a substituted or unsubstituted phenylene group.

According to one embodiment of the present invention, in formulas 5 to 8, L is a pyridine group, a pyrimidine group, a triazine group, an anthracene group, a phenanthrene group, a naphthalene group, or a phenylene group.

According to one embodiment of the present invention, in formulas (5) to (8), L is a pyridine group, a pyrimidine group, a triazine group, an anthracene group or a phenylene group.

According to one embodiment of the present invention, in formulas (5) to (8), p and x are 0 or 1, respectively.

According to one embodiment of the present invention, in formulas 5 to 8, Ar is substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted thiazinyl, substituted or unsubstituted anthryl, Substituted or unsubstituted phenanthryl, substituted or unsubstituted naphthyl, or substituted or unsubstituted phenyl group.

According to one embodiment of the present invention, in formulas 5 to 8, Ar is substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted thiazinyl, substituted or unsubstituted anthryl, Substituted or unsubstituted phenanthryl, substituted or unsubstituted naphthyl, or substituted or unsubstituted phenyl group, which may be substituted by phenyl, naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl, Naphthyl, biphenyl, anthryl, phenanthryl, pyridyl, pyrimidyl, triazinyl, quinolyl, isoquinolyl, and further substituted with at least one of .

According to one embodiment of the present invention, in formulas (5) to (8), q and y are each 1 or 2.

According to one embodiment of the present invention, in formulas (5) to (8), q and y are each 1.

According to one embodiment of the present invention, in formulas (5) to (8), R is hydrogen.

According to one embodiment of the present invention, the formula (1) may be represented by one of the following formulas (9) to (13).

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

In the above formulas, R ₅ to R ₈ are as defined in formula (1)

X ₁ to X ₃ are the same or different and each independently N or CY ₆ , at least one of X ₁ to X ₃ is N,

R, and Y ₁ to Y ₆ are the same as or different from each other, and each independently is the same as defined for R ₁ to R ₄ , and at least two adjacent substituents of R, or at least two adjacent ones of Y ₁ to Y ₆ And n is an integer of 1 to 3. When n is 2 or more, Rs are the same or different from each other, r is an integer of 1 to 5, If there is more than r is 2, Y ₃ is and the same as or different from each other, s is an integer from 1 to 7, not less than s 2 and Y ₄ are the same or different from each other, t is an integer from 1 to 9, t is 2 or more Y < ₅ > are the same or different from each other,

L is a C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted arylene; Or a C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroarylene, p is an integer of 0 to 3, and when p is 2 or more, L is the same or different,

Z 1 and Z 2 are C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aromatic hydrocarbon rings; Or a C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aromatic heterocycle.

는 하기와 같이 표시될 수 있다.According to one embodiment of the present invention,

Can be expressed as follows.

In the above formulas, Y ₁₁ to Y ₁₃ have the same definitions as Y ₆ .

According to one embodiment of the present invention, Y ₁₁ to Y ₁₃ are each a C ₆ to C ₆₀ monocyclic or polycyclic aryl or a C ₆ to C ₆₀ monocyclic or polycyclic heteroaryl substituted or unsubstituted C ₆ to C ₆₀ monocyclic or polycyclic aryl group; Or a C ₆ to C ₆₀ monocyclic or polycyclic aryl or a C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl.

는 하기 구조를 포함한다.According to one embodiment of the present invention,

Includes the following structure.

In the above structural formulas, T ₁ to T ₉ are each CRR ', NR, S or O,

R and R 'are the same or different and each is hydrogen; C ₁ to C ₆₀ linear or branched, 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, T ₁ , T ₂ , T ₄ , T ₇ , T ₈ and T ₉ are each independently CRR ', NR, S or O, and T ₃ , T ₅ and T ₆ are Independently S or O.

According to one embodiment of the present invention, when at least one of T ₁ to T ₉ is CRR ', R and R' are the same or different and are each independently C ₁ to C ₆ alkyl; Or C ₆ to C ₂₀ aryl.

According to one embodiment of the present invention, when at least one of T ₁ to T ₉ is CRR ', R and R' are the same or different and each independently methyl or phenyl.

According to one embodiment of the present invention, when at least one of T ₁ to T ₉ is NR, R is C ₆ to C ₂₀ aryl.

According to one embodiment of the present invention, when at least one of T ₁ to T ₉ is NR, R is phenyl.

According to one embodiment of the present invention, in the above formulas (9) to (13), p is an integer of 0 to 2, and L is phenylene.

According to one embodiment of the present invention, the compound of Formula 1 may be selected from the following compounds.

The above-mentioned compounds can be produced on the basis of the preparation examples described later. Exemplary examples are described below in the preparation examples, but substituents can be added or removed as needed, and the position of the substituent can be changed. In addition, based on techniques known in the art, starting materials, reactants, reaction conditions, and the like can be changed. The type or position of the substituent at the remaining positions may be changed as required by those skilled in the art using techniques known in the art.

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, an electron transport layer 304, and an electron injection layer 305. 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 diode. 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, a light emitting material, an electron transporting material, and an electron injecting material in an organic light emitting device. The organic compound layer containing the compound of Formula 1 may be a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, or an electron injection layer. In particular, the compound of Formula 1 may be used as an electron injecting and / or transporting layer material of an organic light emitting device.

According to one embodiment, the organic material layer comprising the compound of Formula 1 is an electron transport layer.

According to another embodiment, the compound of Formula 1 may be used as a light emitting material of an organic light emitting device. In one embodiment, the organic compound layer including the compound of Formula 1 may be a light emitting layer of an organic light emitting device.

The compound of Formula 1 may be used as a phosphorescent host material. In this case, the compound of formula (1) is used together with the luminescent dopant. As the luminescent dopant material, those known in the art can be used.

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 different two-terminal 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.

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.

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.

According to one embodiment of the present invention, a compound of formula (1) can be prepared by forming a core structure in the same manner as in the following Reaction Scheme 1 and introducing a substituent in the same manner as in Reaction Formula 2 or 3.

[Reaction Scheme 1]

When the compound a-1 and the compound b-1 are produced together as shown in Reaction Scheme 1, the compound can be isolated by a method known in the art, for example, column chromatography.

In Schemes 2 and 3, R has the same definition as R ₁ to R _{8 in} the above-mentioned formula (1).

In the above Reaction Schemes 1 to 3, only the substituent is introduced at the position of R ₂ or R ₄ , but substitution of the substituent at the remaining position may be carried out by a person skilled in the art using a technique known in the art. For example, the position of a substituent can be changed according to the substituted position of Br.

The procedure of Scheme 1 described above was carried out as follows.

compound 1-3 Manufacturing

6.9 ml (49.86 mmol) of triethylamine was added to a mixed solution of 8.05 g (49.37 mmol) of N-hydroxyphthalimide in 160 ml of acetone, and the mixture was stirred for 10 minutes. 10 g (49.37 mmol) of 1-chloro-2,4-dinitrobenzene was added to the reaction mixture, and the mixture was further stirred at room temperature for 2 hours. When the reaction was completed, it was poured into ice water and the solids formed were filtered. The filtered solid was washed with methanol and hexane and dried to obtain 15.05 g (93%) of the desired compound 1-3.

compound 1-2 Manufacturing

17.74 g (53.88 mmol) of 2- (2,4-dinitrophenoxy) isoindoline-1,3-dione was dissolved in 350 ml of dichloromethane, and then 7.6 ml of hydrazine monohydrate mmol) was added thereto, followed by stirring for 4 hours. When the reaction was completed, 1 N HCl was poured at 0 ° C again and stirred, and the resulting solid was filtered. The filtered solid was washed with MeCN, and the filtrate was extracted with MC. The organic layer was dried over MgSO ₄ to obtain 10.50 g (98%) of the desired compound 1-2.

compound 1-1 Manufacturing

9.2 ml (94.94 mmol) of 3-bromopyridine was added to a mixed solution of H ₂ O and THF (38 ml each), 28.36 g (142.41 mmol) of O- (2,4-dinitrophenyl) hydroxylamine . The reaction mixture was stirred at 40 ° C for 12 hours and then maintained at 0 ° C. Then, 475 ml of 2.5N NaOH and 36.20 g (189.88 mmol) of TsCl dissolved in 152 ml of THF were added thereto, followed by further stirring for 4 hours. When the reaction was completed, the reaction mixture was extracted with MC, and the organic layer was dried over MgSO ₄ to obtain 16 g (52%) of the desired compound 1-1.

compound a-1 And  b-1 Manufacturing

16 g (48.90 mmol) of 3- (3-bromopyridin-1-yum-1-yl) (tosyl) amide ((3-bromopyridin- ) After dissolving 14.2 ml (58.68 mmol) of phenyltrifluoromethane sulfonate in THF, 22.28 g (146.7 mmol) of cesium fluoride was slowly added while stirring, followed by stirring at 70 ° C for 24 hours. When the reaction was completed, the reaction mixture was extracted with EA, and the organic layer was dried with MgSO ₄ . EA / Hex development solvent, and 2.17 g (18%) of the target compound a-1 and 4.59 g (38%) of b-1 were obtained.

[Preparation Example 1] Preparation of Compound 6

compound 6 Manufacturing

(8.09 mmol) of 8-bromopyrido [1,2-b] indazole, 2,4-di ([ , 4.97 g (9.71 mmol) of 5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1,3,5-triazine (compound Ar ₁ ), tetrakis ) Palladium (0.94 g, 0.81 mmol) and potassium carbonate (3.35 g, 24.27 mmol) were stirred for 24 hours under reflux in toluene, H ₂ O and ethanol. When the reaction was completed, the reaction mixture was extracted with EA, and the organic layer was dried with MgSO ₄ . EA / Hex development solvent, and 2.45 g (55%) of the target compound 6 was obtained.

[ Manufacturing example  2 to Manufacturing example  11] compound One, compound 3, compound 8, compound 12, compound 13, compound 16, compound 18, compound 28 , Compound 35 And compound  38 Manufacturing

To a compound Ar ₁ repeated except for using the compound shown in Table 1, and is carried out in the same way as Preparation Example 1, Compound 1, Compound 3, Compound 8, Compound 12, Compound 13, Compound 16, Compound 18, Compound 28 , Compound 35 and Compound 38 were prepared.

[Preparation Example 12] Preparation of Compound 66

compound 66 Manufacturing

(9,10-di (naphthalen-2-yl) anthracen-2-yl) -4,4,5,6-tetrahydro- (19.91 mmol) of 5-tetramethyl-1,3,2-dioxaborolane, 1.92 g (1.66 mmol) of tetrakis (triphenylphosphine) palladium and 6.88 g (49.77 mmol) Toluene, H ₂ O, and ethanol. The mixture was stirred for 24 hours under reflux. When the reaction was completed, the reaction mixture was extracted with EA, and the organic layer was dried with MgSO ₄ . EA / Hex development solvent, and 5.9 g (60%) of the desired compound 66 was obtained.

[ Manufacturing example  13 - Manufacturing example  21] Compound 39 , Compound 41 , Compound 42 , Compound 44 , Compound 45 , Compound 47 , Compound 51 , Compound 54  And compound 76 Manufacturing

To to a compound Ar ₂ using the compounds of Table 2, carried out in the same manner as Preparative Example 12, Compound 39, Compound 41, Compound 42, Compound 44, Compound 45, Compound 47, Compound 51, Compound 54 and Compound 76 .

According to one embodiment of the present invention, the compound of formula (1) can be prepared according to the following reaction scheme (4).

 [Reaction Scheme 4]

In Scheme 4, R is as defined in R ₁ to R _{8 in} the above-mentioned formula (1). It is apparent to those skilled in the art that the substituent position can be changed according to the substituted position of Br.

compound 2-3 Manufacturing

3 ml (31.65 mmol) of 2-bromopyridine was added to a mixed solution of H ₂ O and THF (13 ml each), 9.45 g of O- (2,4-dinitrophenyl) hydroxylamine (Compound 1-2) mmol). The reaction mixture was stirred at 40 DEG C for 12 hours and then maintained at 0 DEG C. Then, 12.07 g (63.30 mmol) of TsCl dissolved in 158 mL of 2.5 N NaOH and 51 mL of THF was added, and the mixture was further stirred for 4 hours. When the reaction was completed, the reaction mixture was extracted with MC, and the organic layer was dried over MgSO ₄ to obtain 6.01 g (58%) of the target compound 2-3 .

compound a-2 Manufacturing

6 g (18.34 mmol) of 2- (2-bromopyridin-1-yum-1-yl) (tosyl) amide ) 10.9 ml (36.68 mmol) of phenyltrifluoromethanesulfonate was dissolved in THF, and 8.36 g (55.02 mmol) of cesium fluoride was slowly added while stirring, followed by stirring at 70 ° C for 24 hours. When the reaction was completed, the reaction mixture was extracted with EA, and the organic layer was dried with MgSO ₄ . EA / Hex development solvent, and 3.26 g (72%) of the target compound a-2 was obtained.

[Preparation Example 22] Preparation of Compound 78

compound 78 Manufacturing

(12.14 mmol) of 7-bromopyrido [1,2-b] indazole, 2,4-di (naphthalen-2-yl) -6- (4,4,5,5- 6.69 g (14.57 mmol) of tetrakis (triphenylphosphine) palladium, 1.40 g (1.21 mmol) of potassium carbonate, 5.03 g g (36.42 mmol) were stirred in toluene, H ₂ O, and ethanol mixed solution under reflux for 24 hours. When the reaction was completed, the reaction mixture was extracted with EA, and the organic layer was dried with MgSO ₄ . EA / Hex developing solvent, and 4.91 g (81%) of the aimed compound 78 was obtained.

[ Manufacturing example  23 - Manufacturing example  31] Compound 86 , Compound 87 , Compound 93 , Compound 99 , Compound 102 , Compound 104 , Compound 105 , Compound 110  And compound 114 Manufacturing

The compound 86, the compound 87, the compound 93, the compound 99, the compound 102, the compound 104, the compound 105, and the compound 110 were obtained in the same manner as in the preparation example 22, except that the compound shown in the following Table 3 was used as the compound Ar ₃ . And compound 114 were prepared.

According to one embodiment of the present invention, the compound of Chemical Formula 1 can be prepared according to the following Reaction Scheme 5.

[Reaction Scheme 5]

In Scheme 5, R is defined as R ₁ to R _{8 in} the above-mentioned formula (1). It is apparent to those skilled in the art that the position of a substituent can be changed depending on the substituted position of Br of the starting material or the position of the condensed ring.

compound 3-3 Manufacturing

2 ml (14.42 mmol) of 3-bromoquinoline was added to a mixed solution of H ₂ O and THF (6 ml), and 4.31 g of O- (2,4-dinitrophenyl) hydroxylamine (Compound 1-2) mmol). The reaction mixture was stirred at 40 ° C for 12 hours, maintained at 0 ° C, and then added with 72 ml of 2.5N NaOH and 5.50 g (28.84 mmol) of TsCl dissolved in 23 ml of THF, followed by further stirring for 4 hours. When the reaction was completed, the reaction mixture was extracted with MC, and the organic layer was dried over MgSO ₄ to obtain 2.01 g (37%) of the target compound 3-3 .

compound b-3 Manufacturing

(11.93 mmol) of 4- (3-bromoquinolin-1-ium-1-yl) (tosyl) amide ((3-bromoquinolin- Silyl) phenyltrifluoromethanesulfonate (5.8 g, 35.79 mmol) was dissolved in THF, followed by slow stirring. Then, cesium fluoride (5.44 g, 35.79 mmol) was added thereto and stirred at 70 ° C for 24 hours. When the reaction was completed, the reaction mixture was extracted with EA, and the organic layer was dried with MgSO ₄ . EA / Hex development solvent, and 3.01 g (85%) of the target compound b-3 was obtained.

[Manufacturing Example 32] Production of Compound 152

compound 152 Manufacturing

(10.10 mmol) of 6-bromovazolo [2,3-a] quinoline, 2- (4- (9,10-di (naphthalen- 7.67 g (12.12 mmol) of 5,5-tetramethyl-1,3,2-dioxaborolane (Ar ₄ ), 1.17 g (1.01 mmol) of tetrakis (triphenylphosphine) palladium, 4.19 g g (30.3 mmol) was stirred for 24 hours under reflux in toluene, H ₂ O, and ethanol. When the reaction was completed, the reaction mixture was extracted with EA, and the organic layer was dried with MgSO ₄ . EA / Hex developing solvent, and 6.21 g (85%) of the desired compound 152 was obtained.

[ Manufacturing example  33 - Manufacturing example  42] Compound 119 , Compound 123 , Compound 128 , Compound 134 , Compound 136 , Compound 139 , Compound 142 , Compound 144 , Compound 146  And compound 150 Manufacturing

Using the compounds of Table 4 as compound Ar ₄ and performs in the same manner as Preparative Example 32, Compound 119, Compound 123, Compound 128, Compound 134, Compound 136, Compound 139, Compound 142, Compound 144, Compound 146 And Compound 150 were prepared.

According to one embodiment of the present invention, the compound of formula (1) may be prepared according to the following reaction scheme (6).

 [Reaction Scheme 6]

In Scheme 6, R is the same as defined for R ₁ to R _{8 in} the above-mentioned formula (1). It is apparent to those skilled in the art that the position of a substituent can be changed depending on the substituted position of Br of the starting material or the position of the condensed ring.

compound 4-4 Manufacturing

(19.23 mmol) of 4-bromoisoquinoline was added to a mixed solution of H ₂ O and THF (8 ml each), 5.74 g (28.85 mmol) of O- (2,4-dinitrophenyl) hydroxylamine mmol). The reaction mixture was stirred at 40 ° C for 12 hours, maintained at 0 ° C, and 7.33 g (38.46 mmol) of TsCl dissolved in 96 ml of 2.5 N NaOH and 31 ml of THF was added thereto, followed by further stirring for 4 hours. When the reaction was completed, the reaction mixture was extracted with MC, and the organic layer was dried over MgSO ₄ to obtain 2.4 g (33%) of the target compound 4-4 .

compound a-4 Manufacturing

(5.30 mmol) of 2- (4-bromoisoquinolin-2-ium-2-yl) (tosyl) amide), 2- (trimethyl Silyl) phenyltrifluoromethanesulfonate (2.6 ml, 10.60 mmol) was dissolved in THF, followed by stirring slowly, 2.42 g (15.90 mmol) of cesium fluoride was added, and the mixture was stirred at 70 ° C for 24 hours. When the reaction was completed, the reaction mixture was extracted with EA, and the organic layer was dried with MgSO ₄ . EA / Hex developing solvent, and 1.21 g (77%) of the target compound a-4 was obtained.

[Preparation Example 43] Preparation of Compound 173

compound 173 Manufacturing

(4.04 mmol) of 5-bromomethazolo [3,2-a] isoquinoline, 2,2 '- (4- (4,4,5,5,5-tetramethyl-1,3,2-dioxa borol lane-2-yl) pyridine-2,6-diyl) di-quinoline _{(Ar 5) 2.23g (4.85m㏖)} , tetrakis (triphenylphosphine) palladium, 0.46g (0.40m㏖), potassium carbonate 1.68g (12.12 mmol) were stirred for 24 hours under reflux in toluene, H ₂ O, and ethanol mixed solution. When the reaction was completed, the reaction mixture was extracted with EA, and the organic layer was dried with MgSO ₄ . EA / Hex development solvent, and 1.73 g (78%) of the target compound 173 was obtained.

[ Manufacturing example  44 - Manufacturing example  53] Compound 161 , Compound 167 , Compound 171 , Compound 176 , Compound 179 , Compound 180 , Compound 183 , Compound 185 , Compound 188  And compound 190 Manufacturing

To a compound Ar ₅ using the compounds of Table 5, and carried out in the same manner as Preparative Example 43, Compound 161, Compound 167, Compound 171, Compound 176, Compound 179, Compound 180, Compound 183, Compound 185, Compound 188 And compound 190 were prepared.

According to one embodiment of the present invention, the compound of Chemical Formula 1 can be prepared according to the following Reaction Scheme 7.

 [Reaction Scheme 7]

In Scheme 7, R has the same definition as R ₁ to R _{8 in} the above-mentioned formula (1). It is obvious to a person skilled in the art that the kind and position of the substituent of the compound of the formula (1) can be changed depending on the substituent type and position of the starting material.

compound 7-3 Manufacturing

(37.83 mmol) of 2-bromobenzaldehyde, 8.22 g (45.40 mmol) of 1-bromo-4-ethynylbenzene, 7.6 ml (54.48 mmol) of triethylamine, 0.53 g (0.76 mmol) of dichloride and 0.29 g (1.51 mmol) of copper iodide were stirred in DMF solution at 100 占 폚 for 4 hours. When the reaction was completed, the reaction mixture was extracted with EA, and the organic layer was dried with MgSO ₄ . EA / Hex development solvent, and 7.23 g (67%) of the target compound 7-3 was obtained.

compound 7-2 Manufacturing

7 g (24.55 mmol) of 2 - ((4-bromophenyl) ethynyl) benzaldehyde and 5.03 g (27.01 mmol) of p-toluenesulfonyl hydrazide were dissolved in methanol and stirred at room temperature for 4 hours. When the reaction was completed, recrystallization from methanol gave 8.68 g (78%) of the desired compound 7-2 .

compound 7-1 Manufacturing

(17.65 mmol) of (E) -N'- (2 - ((4-bromophenyl) ethynyl) benzylidene) -4-methylbenzenesulfonohydrazide, 0.45 g of silver trifluoromethanesulfonate 1.77 mmol) was dissolved in MeCN, stirred at 80 ° C for 6 hours, and then cooled at room temperature. To the reaction mixture, 5.1 ml (21.18 mmol) of 2- (trimethylsilyl) phenyltrifluoromethanesulfonate and 8.04 g (52.95 mmol) of cesium fluoride were added and the mixture was further stirred at 80 占 폚 for 12 hours. When the reaction was completed, the reaction mixture was extracted with EA, and the organic layer was dried with MgSO ₄ . EA / Hex development solvent, and 4.68 g (71%) of the desired compound 7-1 was obtained.

[Manufacturing Example 54] Preparation of Compound 204

compound 204 Manufacturing

4,6-di (phenanthren-9-yl) -2- (4,4,5,6-tetrahydropyrimidin- 5-tetramethyl-1,3,2-dioxa borol lane-2-yl) pyrimidine _{(Ar 6) 7.18g (12.86m㏖)} , tetrakis (triphenylphosphine) palladium, 1.24g (1.07m㏖) , And 4.44 g (32.16 mmol) of potassium carbonate were stirred for 24 hours under reflux in toluene, H ₂ O, and ethanol. When the reaction was completed, the reaction mixture was extracted with EA, and the organic layer was dried with MgSO ₄ . EA / Hex development solvent, and 6.68 g (86%) of the target compound 204 was obtained.

[ Manufacturing example  55 - Manufacturing example  63] compound 194 , Compound 196 , Compound 198 , Compound 202 , Compound 206 , Compound 208 , Compound 213 , Compound 218  And compound 228 Manufacturing

To a compound Ar ₆ using the compounds of Table 6, carried out in the same manner as Preparative Example 54, Compound 194, Compound 196, Compound 198, Compound 202, Compound 206, Compound 208, Compound 213, Compound 218 and Compound 228 .

[ Manufacturing example  64] Preparation of Compound 231

compound 231-1 Manufacturing

(25.9 g, 108 mmol), 1-bromo-2-nitrobenzene (20 g, 99 mmol) was added to one neck rbf, , A mixture of Pd (PPh ₃ ) ₄ (5.7 g, 4.95 mmol), K ₂ CO ₃ (27.3 g, 198 mmol) and THF (250 mL) / H ₂ O (50 mL) Respectively. After the water layer was removed, the organic layer was dried over MgSO ₄ . Column chromatography, concentrated (SiO _2, hexane: dichloromethane = 2: 1), to give a yellow solid separated as a compound 231-1 (21 g, 61%) .

compound 231-2 Manufacturing

Under nitrogen, the compound 231-1 (20 g, 63.4 mmol), PPh ₃ (49.8 g, 190 mmol) and 1,2-dichlorobenzene (300 ml) was refluxed at 180 占 폚 for 18 hours. 1,2-chromatography after removal of the benzene to the distillation column Photography (SiO _2, hexane: dichloromethane = 3: 1) to separate a white solid compound 231-2 (6.6g, 36%), Compound 251-2 (7.5 g, 41%).

compound 231 Manufacturing

The compound 231-2 (4.8 g, 16.9 mmol), a-1 (4.1 g, 16.9 mmol), Cu (1 g, 16.9 mmol), 18-crown- 550 mg, 1.69 mmol), K ₂ CO ₃ (7 g, 50.7 mmol) and o- DCB (130 ml) was refluxed at 180 ° C. for 60 hours. The 1,2-dichlorobenzene was removed by distillation and then separated by column chromatography (SiO ₂ , hexane: dichloromethane = 2: 1) to obtain a white solid compound 231 (3.2 g, 42%).

[ Manufacturing example  65] compound 236 Manufacturing

compound 236-1 Manufacturing

Under nitrogen, a solution of 2-bromo-9,9-dimethyl-9H-fluorene (15 g, 54.91 mmol), benzo [b] thiophen-2-yl tributylstannane (34.8, 82.3 mmol ), Pd (PPh ₃ ) ₄ and toluene (350 ml) was refluxed at 110 ° C for 12 hours. After concentration and silica gel filtration, the compound precipitated with CH ₂ Cl ₂ / MeOH was filtered at high temperature with EtOH to obtain an opaque white solid compound 236-1 (15.7 g, 87%).

compound 236-2 Manufacturing

Under nitrogen, a mixture of AcOH (260 ml) containing the compound 236-1 (15.7 g, 48 mmol) and HNO ₃ (6 ml, 143 mmol) was slowly added to a round neck rbf The mixture was heated to 60 占 폚 and stirred for 30 minutes. After cooling to room temperature, it was filtered and washed with distilled water (500 ml). The resulting material was dried in a vacuum oven at 50 < 0 > C for 12 hours to give a yellow solid compound 236-2 (16.1 g, 90%).

compound 236-3 Manufacturing

A mixture of the compound 236-2 (16.1 g, 43 mmol), PPh ₃ (33.8 g, 129 mmol) and 1,2-dichlorobenzene (250 ml) was heated to 200 ° C under nitrogen for 18 hours. 1,2-Dichlorobenzene was distilled off and the product was separated by column chromatography (SiO ₂ , hexane: dichloromethane = 2: 1) to obtain a light-colored solid compound 236-3 (3.0 g, 20%).

compound 236 Manufacturing

To a solution of the compound 263-3 (2 g, 5.85 mmol), a-1 (1.4 g, 5.85 mmol), Cu (374 mg, 5.85 mmol), 18-crown- , 0.58 mmol), K ₂ CO ₃ (1.6 g, 11.78 mmol) and o- DCB (25 ml) was refluxed at 180 ° C. for 60 hours. The 1,2-dichlorobenzene was removed by distillation, followed by separation by column chromatography (SiO ₂ , hexane: dichloromethane = 3: 1) to obtain solid compound 236 (1.45 g, 48%).

[ Manufacturing example  66] Compound 241 Manufacturing

compound 241-1 Manufacturing

9,9-dimethyl -9H- fluorene-2-Daily acid (25.95g, 109m㏖), 3- bromo-thiazol-naphthenic (10㎖, 72.5m㏖), Pd ( PPh 3) 4 (4.189g, A mixture of K ₂ CO ₃ (30.06 g, 217.5 mmol), toluene (200 ml), ethanol (40 ml) and H ₂ O (40 ml) was refluxed. After stirring at reflux temperature for 4 hours, the solvent was concentrated and extracted with MC. The solid was washed with methane and filtered. White solid compound 241-1 was obtained (30 g, 87%).

compound 241-2 Manufacturing

To a solution of the compound 241-1 (21.3 g, 65.3 mmol) in AcOH (1,260 ml) under nitrogen was added slowly a mixture of AcOH (12 ml) containing HNO ₃ (5.9 ml, 130 mmol) The mixture was heated to 60 DEG C and stirred for 30 minutes. The solution was cooled to room temperature, filtered, and washed with distilled water (400 ml). The resulting material was dried in a vacuum oven at 50 < 0 > C for 12 hours to give a bright yellow solid compound 241-2 (21.0 g, 95%).

compound 241-3 Manufacturing

A mixture of the above compound 241-2 (29.5 g, 79.4 mmol), PPh ₃ (54.8 g, 198.5 mmol) and 1,2-dichlorobenzene (450 ml) was added to a one neck rbf under nitrogen charging at 180 ° C for 4 hours Lt; / RTI > The 1,2-dichlorobenzene was removed by distillation, followed by separation by column chromatography (SiO ₂ , hexane: dichloromethane = 4: 1) to obtain yellow solid compound 241-3 (15 g, 55%).

compound 241 Manufacturing

The compound 241-3 (4 g, 11.7 mmol), a-1 (2.89 g, 11.7 mmol), Cu (748 mg, 11.7 mmol), 18-crown- , 1.17 mmol), K ₂ CO ₃ (3.2 g, 23.56 mmol) and o- DCB (50 ml) was refluxed at 180 ° C. for 60 hours. The 1,2-dichlorobenzene was removed by distillation, followed by column chromatography (SiO ₂ , hexane: dichloromethane = 3: 1) to obtain solid compound 241 (1.9 g, 32%).

[ Manufacturing example  67] Compound 247 Manufacturing

compound 247-1 Manufacturing

(27 g, 118.7 mmol), K ₂ CO ₃ (10 g, 107.9 mmol), dibenzo [b, d] thiophene-4-ylboronic acid , 10.8 mmol), H ₂ O (90 ml) and 1,4-dioxane (360 ml) was refluxed at 110 ° C for 12 hours. After concentration, the mixture was extracted with CH ₂ Cl ₂ (3 × 300 ml) and distilled water (150 ml), followed by silica gel filtration. After concentration, the mixture was stirred with MeOH (400 mL) for 1 hour, and then precipitated with CH ₂ Cl ₂ / MeOH and filtered to obtain a brown solid compound 247-1 (26.5 g, 77%).

compound 247-2 Manufacturing

To a solution of the compound 247-1 (26 g, 82.1 mmol) in AcOH (400 ml) under nitrogen was added slowly a solution of AcOH (400 ml) containing HNO ₃ (10 ml, 246.4 mmol) The mixture was heated to 60 DEG C and stirred for 30 minutes. After cooling to room temperature, it was filtered and washed with distilled water (800 ml). The resulting solid compound was dissolved in CH ₂ Cl ₂ (200 mL), the water layer was removed, and the organic layer was concentrated under reduced pressure. The concentrate was adsorbed and then separated by column chromatography (SiO ₂ , hexane: dichloromethane = 3: 1) to obtain yellow solid compound 247-2 (19.6 g, 66%).

compound 247-3 Manufacturing

The original neck rbf in a nitrogen charged the compound 247-2 (17.9g, 49.6m㏖), PPh 3 (38.7g, 148.4m㏖), 1,2- dichlorobenzene (500㎖) for reflux at 180 ℃ 12 sigan mixture Respectively. After removing 1,2-dichlorobenzene by distillation, it was filtered with a CH ₂ Cl ₂ / MeOH precipitate and then separated by column chromatography (SiO ₂ , hexane: dichloromethane = 2: 1) to obtain an opaque white solid compound 247- 3 (10 g, 61%).

compound 247 Manufacturing

(10 g, 30.35 mmol), a-1 (7.4 g, 30.35 mmol), Cu (1.9 mg, 30.35 mmol), 18-crown- 987 mg, 3.03 mmol), K ₂ CO ₃ (8.3 g, 60.7 mmol) and o- DCB (100 ml) was refluxed at 180 ° C. for 60 hours. After removing 1,2-dichlorobenzene by distillation, the product was separated by column chromatography (SiO ₂ , hexane: dichloromethane = 3: 1) to obtain a solid compound 247 (8.9 g, 59%).

[ Manufacturing example  68] Compound 250 Manufacturing

compound 250-1 Manufacturing

Sulfuric acid (1.4 ml, 0.1 eq) was added to a mixture of 1,2-dichlorohexanone (30.0 g, 1.0 eq), phenylhydrazine hydrochloride (77.37 g, 2.0 eq) and ethanol (1,000 ml) Followed by stirring at 60 ° C for 4 hours. The solution cooled to room temperature was filtered to give a tan solid compound 250-1 (69 g, 93%).

compound 250-2 Manufacturing

Trifluoroacetic acid (46.5 ml, 2.4 eq) was added to a mixture of acetic acid (700 ml) containing the compound 250-1 (68.9 g, 1.0 eq) and the mixture was stirred at 100 ° C for 15 hours. The solution cooled to room temperature was washed with acetic acid and hexane and filtered to obtain an ivory solid compound 250-2 (27.3 g, 42%).

compound 250-3 Manufacturing

(2.1 g, 1.0 eq), iodobenzene (2.5 g, 1.5 eq), Cu (0.312 g, 0.6 eq), 18-crown-6-ether , 0.2 eq), K ₂ CO ₃ (3.397 g, 3.0 eq) and 1,2-dichlorobenzene (20 ml) was stirred at reflux temperature for 16 hours. The solution cooled to room temperature was extracted with MC / H ₂ O, concentrated, and separated by column chromatography (SiO ₂ , hexane: ethyl acetate = 10: 1) to obtain a white solid compound 250-3 (1.76 g, 64%).

compound 250 Manufacturing

(1.7 g, 5.11 mmol), a-1 (1.2 g, 5.11 mmol), Cu (324 mg, 5.11 mmol), 18-crown- 166 mg, 0.51 mmol), K ₂ CO ₃ (1.4 g, 0.22 mmol) and o- DCB (10 ml) was refluxed at 180 ° C. for 60 hours. After removing 1,2-dichlorobenzene by distillation, the solid compound 250 was obtained (770 mg, 30%) by column chromatography (SiO ₂ , hexane: dichloromethane = 2: 1).

[ Manufacturing example  69] Compound 251 Manufacturing

251-1 (1g, 3.53 m㏖) wherein the compound in the original neck rbf, a-1 (872mg, 353m㏖), Pd (OAc) 2 (80mg, 0.353 m㏖), K 3 PO 4 (1.4g, 7.06m ), P (t-Bu) ₃ (1.5 ml, 1 mmol) and o- DCB (10 ml) was refluxed at 100 ° C for 24 hours. After MC extraction, drying with MgSO ₄ and column chromatography (SiO ₂ , hexane: dichloromethane = 2: 1), solid compound 251 was obtained (950 mg, 60%).

[ Manufacturing example  70] Compound 256 Manufacturing

compound 256-1 Manufacturing

(20 g, 94.33 mmol), 1-bromo-2-nitrobenzene (19 g, 94.33 mmol), K ₂ CO ₃ (26 g, 188 mmol), H ₂ O (45 ml) and 1,4-dioxane (300 ml) was refluxed at 110 ° C for 12 hours. After concentration, CH ₂ Cl ₂ (3 x 200 ml) and distilled water (120 ml), followed by silica gel filtration. Column chromatography, concentrated (SiO _2, hexane: dichloromethane = 8: 1) to obtain a separated solid ivory compound 256-1 (18.2g, 67%).

compound 256-2 Manufacturing

A mixture of the above compound 256-1 (19 g, 65.6 mmol), PPh ₃ (51.6 g, 197 mmol) and 1,2-dichlorobenzene (400 ml) was heated to 180 캜 under nitrogen charging at reflux for 12 hours . After removing 1,2-dichlorobenzene by distillation, the precipitate was precipitated with CH ₂ Cl ₂ / MeOH, filtered and then separated by column chromatography (SiO ₂ , hexane: dichloromethane = 2: 1) to obtain white solid compound 256-2 (6.7 g, 39%).

compound 256 Manufacturing

(6.7g, 26mmol), S1 (6.4g, 26mmol), Cu (1.6g, 26mmol), 18-crown-6-ether (847mg, 2.6m ㏖), K ₂ CO ₃ (7.1 g, 52 mmol) and o- DCB (100 ml) was refluxed at 180 ° C. for 48 hours. The 1,2-dichlorobenzene was removed by distillation, followed by separation by column chromatography (SiO ₂ , hexane: dichloromethane = 3: 1) to obtain a white solid compound 256 (7.5 g, 68%).

[Preparation of compounds a-5 and b-5 ]

The original neck rbf a-1 or b-1 (3g, 12.1mmol) , (3- bromo-phenyl) boronic acid (2.4g, 12.1mmol), Pd ( PPh 3) 4 (1.39g, 1.21mmol), K ₂ CO ₃ (3.34 g, 24.2 mmol) and toluene (50 mL) / H ₂ O (10 mL) was heated at 70 ° C for 24 hours. After the water layer was removed, the organic layer was dried over MgSO ₄ . Column chromatography (SiO _2, hexane: dichloromethane = 3: 1) and then concentrated to remove to obtain a solid compound a-5 (2.8g, 71% ) or b-5 (2.7g, 68% ).

[ Manufacturing example  71] Compound 271 Manufacturing

Was synthesized in the same manner as in the preparation of Compound 236 except for using the compound a-5 instead of the compound a-1.

[ Manufacturing example  72] Compound 281 Manufacturing

Was synthesized in the same manner as the compound 231 except for using the above compound b-1 instead of the above-mentioned compound a-1.

[ Manufacturing example  73] Compound 316 Manufacturing

Was synthesized in the same manner as the compound 231 except for using the above compound b-5 instead of the above-mentioned compound a-1.

[ Manufacturing example  74] Compound 321 Manufacturing

Was synthesized in the same manner as the compound 236 except for using the compound b-5 instead of the compound a-1.

The compound was prepared in the same manner as in the above Synthesis Experimental Example, and the results of the confirmation of the synthesis are shown in Table 7.

compound
number ¹ H NMR Found Calculated One (M, 8H), 7.19 (d, IH), 7.62 (d, IH) 399.45 399.15 3 2H), 7.62-7.41 (m, 7H), 7.19 (d, 2H), 8.44 (d, 1H) 501.54 501.17 6 (M, 12H), 7.25-7.19 (m, 2H), 7.62 (d, 1H) 5H) 551.64 551.21 8 2H), 8.02 (d, 2H), 7.92-7.85 (m, 5H), 7.66-7.48 (m, m, 7H), 7.25-7.19 (m, 5H) 653.73 653.23 12 2H), 7.62-7.41 (m, 5H), 7.62 (d, 2H) 7H), 7.19 (d, 1 H) 500.55 500.17 13 2H), 7.63-7.48 (m, 7H), 7.19 (d, 2H), 8.83 (d, 2H), 8.61-8.59 d, 1 H) 500.55 500.17 16 1H), 7.80-7.48 (m, 2H), 7.75-7.85 (m, 5H) 7.19 (d, 1 H) 552.63 552.21 18 2H), 7.62-7.60 (m, 3H), 8.81 (d, 2H) 7.50-7.48 (m, 2H), 7.35 (d, 2H), 7.19 (d, 1H) 652.74 652.24 28 (D, 2H), 7.62-7.58 (m, 8H), 7.50-7.39 (m, 2H) m, 4 H), 7.19 (d, 1 H) 596.72 596.23 35 2H), 7.99-7.88 (m, 9H), 7.62 (t, 1H), 7.50-7.48 (m, 2H), 8.81-8.75 m, 2H), 7.25-7. 19 (m, 5H) 627.73 627.24 38 2H), 7.78-7.54 (m, 16H), 7.34-7.82 (m, 2H) 7.32 (m, 2 H) 672.83 672.26 39 1H), 6.68 (t, IH), 7.51-7.41 (m, 7H), 7.19 (d, 399.45 399.15 41 1H), 7.41 (d, 2H), 7.19 (d, 2H), 7.48 (t, d, 1 H), 6.68 (t, 1 H) 501.54 501.17 42 2H), 7.92-7.48 (m, 6H), 7.19 (d, 2H), 8.35-8.32 (m, 4H) 1H), 6.68 (t, 1 H) 501.54 501.17 44 (M, 2H), 7.92-7.85 (m, 5H), 7.62 (t, 1H), 7.52-7.48 (m, 11H), 7.25-7.19 551.64 551.21 45 2H), 7.99-7.85 (m, 9H), 7.62 (t, 1H), 7.48 (t, 1H), 7.25-7.19 t, 1 H) 553.61 553.20 47 2H), 7.65 (t, 2H), 7.65 (d, 2H), 7.65-7.30 (m, 2H), 7.45 (t, 1H), 7.31-7.29 (m, 3H), 6.81 (t, 653.75 653.23 51 (M, 3H), 8.32 (d, 1H), 8.21 (d, 2H), 7.92-7.87 (m, 3H), 7.45 (t, IH), 7.31 (d, IH), 6.81 (t, 500.57 500.17 54 (M, 5H), 8.49 (d, 1H), 8.32-8.30 (m, 5H), 8.00 1H), 7.46 (t, IH), 7.31 (d, IH), 6.81 (t, 552.64 552.21 66 2H), 7.98-7.94 (m, 3H), 7.93-7.91 (m, 2H), 8.02 (d, 2H), 7.18-7.12 (m, 2H), 6.98 (m, 1H), 7.83-7.75 (m, 5H), 7.66-7.63 t, 1 H) 596.73 596.23 76 2H), 7.90 (d, 1H), 7.82-7.67 (m, 8H), 8.78 (d, 1H), 8.14-8.10 (m, 3H), 8.08-8.05 (M, 2H), 6.94 (m, 2H), 7.22-7.17 (m, 672.83 672.26 78 2H), 8.02 (d, 2H), 8.09 (d, 2H), 8.49 (d, 2H), 8.32 (d, 1H), 8.18-8.16 1H), 7.65-7.54 (m, 6H), 7.45 (t, 499.58 499.18 86 (M, 8H), 7.16 (t, 1H), 6.96 (d, 1H), 7.63-7.92 1H) 398.47 398.15 87 8.46 (s, 1H), 8.32 (d, 1H), 8.08-8.06 (d, IH), 7.45 (t, IH), 7.16 (t, 498.59 498.18 93 (D, 2H), 8.55 (d, 2H), 8.37 (s, 1H), 8.32-8.30 (m, 5H), 8.05 (d, 2H), 7.96-7.92 (m, 3H), 7.54-7.45 (m, 4H), 7.25 (d, 652.76 652.24 99 2H), 8.84 (d, 2H), 8.44-8.43 (m, 4H), 8.32 (d, 1H), 8.17 (d, 2H), 7.92-7.90 (m, 3H), 7.70-7.62 1H), 7.16 (t, 1H), 6.96 (d, 1H) 597.72 597.22 102 2H), 7.96-7.92 (m, 3H), 8.87 (d, 2H), 8.69 (d, 2H) , 7.65-7.64 (m, 3H), 7.54-7.45 (m, 4H), 7.25 651.77 651.24 104 2H), 7.92 (d, 1H), 7.65 (d, 2H), 7.65 (d, 2H), 7.04 (d, 1H), 6.78 (d, 1H), 7.48 (d, , 6.69 (t, 1 H) 596.73 596.23 105 2H), 7.65 (d, 2H), 7.65 (t, 1H), 7.55-7.45 (m, 7H), 7.04 (d, 1 H), 6.78 (d, 1 H), 6.69 (t, 473.58 473.19 110 (D, 1H), 7.65 (d, 2H), 7.65 (d, 2H) 1H), 6.69 (d, IH), 6.69 (d, IH) 625.77 625.25 114 2H), 8.09-8.06 (m, 4H), 7.99 (d, 2H), 8.39 (d, 2H), 7.92 (d, 1H), 7.85 (d, 2H), 7.65-7.60 (m, 6H) (m, 2H), 7.04 (d, IH), 6.78 (d, IH), 6.69 672.83 672.26 119 2H), 8.14 (d, 2H), 8.11-8.05 (m, 4H), 7.92-7.90 (m, 3H), 7.84 t, 1 H), 7.70-7.62 (m, 10 H), 7.45 (t, 1 H) 649.76 649.23 123 (M, 2H), 8.11-8.06 (m, 4H), 7.96-7.92 (m, 7H), 7.85-7.84 (m, 3H), 7.69-7.65 2H), 7.54 (t, 2H), 7.45 (t, IH), 7.29 (d, 2H) 703.81 703.25 128 2H), 8.17 (d, 2H), 8.11-8.05 (m, 4H), 7.92-7.90 (m, (m, 3H), 7.84 (t, 1H), 7.70-7.62 (m, 10H), 7.45 648.77 648.23 134 2H), 7.92 (d, 1H), 7.84 (m, 2H), 8.85 (s, 2H), 8.37-8.32 t, 1 H), 7.69-7.59 (m, 6 H), 7.45 (t, 1 H) 547.66 547.20 136 2H), 8.92 (d, 2H), 8.50 (d, 2H), 8.34-8.32 (m, 2H), 8.21-8.20 2H), 7.45 (m, 2H), 7.62 (m, 2H) 549.64 549.20 139 (D, 1H), 7.92 (d, 1H), 7.85-8.69 (m, 8H), 8.34-8.32 7.84 (m, 5 H), 7.69-7.65 (m, 2 H), 7.45 (t, 1 H) 601.71 601.23 142 2H), 7.96 (d, IH), 8.33-8.32 (m, 2H), 8.23-8. 20 (m, 2H), 7.45 (t, 1H), 7.38 (d, 2H), 7.85 (d, , 7.29-7.27 (m, 2H) 646.79 646.24 144 2H), 8.37 (d, 2H), 8.32 (d, 1H), 8.20 (s, 3H), 8.14 (d, 1H), 8.09-8.00 , 7.85 (t, 1 H), 7.71 (t, 1 H), 7.65-7.59 (m, 623.76 623.24 146 8.14 (d, 1H), 8.09 (d, 2H), 8.50 (d, 2H), 8.32 , 7.92-7.85 (m, 4H), 7.71-7.65 (m, 2H), 7.62 (t, 2H), 7.45 625.73 625.23 150 2H), 8.69 (d, 2H), 8.69 (d, 4H), 8.55 (d, 2H), 8.32 (d, , 7.96-7.92 (m, 3H), 7.85 (t, IH), 7.71 (d, IH), 7.65-7.64 (m, 3H), 7.49-7.45 777.93 777.29 152 (M, 5H), 7.99 (d, 1H), 8.39 (d, 2H), 7.92 (d, IH), 7.85 (t, IH), 7.71 (d, IH), 7.65-7.60 , ≪ / RTI > 2H), 7.27-7.25 (m, 6H) 722.89 722.27 161 (D, 2H), 7.99-7.92 (m, 8H), 7.85-7.83 (m, 3H), 7.68-7.92 2H), 7.45 (t, 1H), 7.29 (d, 2H) 703.81 703.25 167 (M, 5H), 7.75 (d, 1H), 7.92 (d, 1H) 4H), 7.68-7.61 (m, 3H), 7.49-7.41 (m, 7H) 600.73 600.23 171 (D, 1H), 7.83 (d, 1H), 7.68-7.61 (m, 5H) 3H), < / RTI > 7.55-7.45 (m, 7H) 447.54 447.17 173 (M, 3H), 7.68-7.96 (m, 5H), 7.92 (d, 7.61 (m, 3 H), 7.53 (t, 2 H), 7.45 (t, 1 H) 549.64 549.20 176 2H), 7.99 (d, 1H), 7.92 (d, 1H), 7.85-7.83 (m, 5H) , 7.75 (d, 4H), 7.68-7.61 (m, 3H), 7.49-7.41 (m, 7H) 599.74 599.24 179 2H), 7.99 (d, 1H), 7.94-7.92 (m, 1H), 8.79 (d, 2H), 7.45 (t, 1H), 7.29 (d, 2H), 7.85-7.83 (m, 3H) 701.83 701.26 180 2H), 8.09-7.92 (m, 9H), 7.81 (d, 1H), 7.65-7.60 (m, 6H), 8.44-8.32 (m, 2H), 7.48-7.45 (m, 2H), 7.38 (d, 2H), 7.29-7.27 (m, 2H) 646.79 646.24 183 2H), 7.53-7.45 (m, 4H), 7.63-7.30 (m, 3H), 8.41-8.32 (m, 6H), 8.04-7.92 ), 7.25 (s, 4H) 625.73 625.23 185 2H), 8.44 (s, 2H), 8.34-8. 32 (m, 2H), 8.20-8.17 (m, 4H), 8.04 (d, 1H), 7.92-7.90 (m, 3H), 7.81 (d, 1H), 7.70-7.61 (m, 10H), 7.48-7.45 723.88 723.27 188 2H), 8.85 (d, 2H), 8.69 (d, 4H), 8.55 (d, 2H), 8.34-8.32 (m, 3H), 7.81 (d, 1H), 7.65-7.61 (m, 4H), 7.49-7.45 777.93 777.29 190 (M, 2H), 8.09-8.04 (m, 5H), 7.99 (d, 2H), 7.92 (m, 2H), 7.38 (d, 2H), 7.27-7.25 (m, 2H), 7.48-7.45 6H) 722.89 722.27 194 (D, 2H), 8.50 (d, 2H), 8.41 (d, 2H), 8.32 -7.87 (m, 5 H), 7.70-7.62 (m, 7 H), 7.45 (t, 1 H) 627.71 627.22 196 7H), 7.75 (d, 2H), 7.70-7.62 (m, 5H), 7.49-7.41 (m, m, 7H), 7.25 (d, 4H) 677.81 677.26 198 2H), 8.55 (d, 2H), 8.32 (d, 1H), 8.05 (d, 3H), 7.96-7.92 (m, 9H), 7.70-7.62 7H), 7.49-7. 45 (m, 3H), 7.25 (d, 4H) 779.91 779.28 202 8H), 7.83 (t, 2H), 7.70-7.62 (m, 7H), 7.53 (m, 2H) t, 2 H), 7.45 (t, 1 H) 626.72 626.22 204 1H), 8.17 (d, 2H), 8.07-8. 05 (m, 3H), 8.08 (d, 2H), 8.84 (d, 2H) , 7.96-7.90 (m, 5H), 7.70-7.62 (m, 13H), 7.45 (t, 724.87 724.26 206 (M, 5H), 8.05-7.92 (m, 8H), 7.85 (d, 4H), 7.70-7.62 7.45 (t, 1 H) 678.80 678.25 208 (M, 5H), 7.85 (t, 2H), 7.85-7.92 (m, 5H), 8.32-8.30 2H), 7.45 (t, 1H), 7.29 (d, 2H), 7.70-7.62 778.92 778.28 213 2H), 8.84 (d, 2H), 8.69 (d, 2H), 8.44 (s, 2H), 8.32 , 7.92-7.85 (m, 5H), 7.70-7.62 (m, 13H), 7.45 (t, 723.88 723.27 218 (M, 2H), 8.09-8.05 (m, 5H), 7.99 (d, 2H), 8.39 2H), 7.92 (d, 1H), 7.85 (d, 2H), 7.70-7. 55 (m, 722.89 722.27 228 (M, 2H), 8.09-8.05 (m, 5H), 7.99 (d, 2H), 8.39 2H), 7.92 (d, 1H), 7.85 (d, 2H), 7.70-7.60 (m, (m, 6H) 798.99 798.30 231 (2H, t), 7.92 (1H, d), 7.63 ~ 7.61 (3H, t), 8.12 ~ 8.09 (2H, t), 7.92 (1H, d), 7.63-7.61 (3H, t), 7.54-7.4 (5H, m), 7.29-7.24 s) 449.55 449.19 236 (8H, m), 7.24 (1H, t), 7.0 (1H, s), 8.05 d), 1.72 (6 H, s) 505.63 505.16 241 (2H, m), 7.62-7.4 (8H, m), 8.04 (1H, d) m), 7.24 (1 H, t), 7.0 (1 H, d) 505.63 505.16 247 (2H, m), 8.4 (1H, s), 8.32 (1H, d), 8.05-7.92 (4H, m), 7.62-7.4 d) 495.09 495.62 250 (2H, d), 8.4 (1H, s), 8.32 (1H, m), 8.12 (1H, d), 7.94-7.92 (3H, m), 7.62-7.45 4H, m), 7.62-7.45 (9H, m), 7.33-7.25 (4H, m), 7.0 498.58 498.18 251 D), 7.62-7.61 (2H, m), 8.55 (1H, d), 8.4 (1H, s), 8.32 m), 7.48-7.4 (3H, m), 7.33-7.24 (3H, m) 449.55 449.19 256 (8H, m), 7.0 (1H, d), 8.42 (1H, 1H, d) 423.46 423.14 271 (1H, m), 7.24-7.19 (2H, m), 1.72 (1H, s), 8.85 6H, s) 581.73 581.19 281 (2H, t), 7.92 (1H, d), 7.63-7.61 (3H, t), 7.54-7.44 (1H, 4H, m), 7.29-7.24 (2H, m), 7.0 (1H, d), 6.6 449.55 449.19 316 (1H, s), 8.85 (1H, s), 8.35-8.32 (2H, t), 8.12 ~ 8.09 (2H, t), 7.92 (1H, m), 7.44 (4H, m), 7.29-7.19 (3H, m), 6.68 525.64 525.22 321 (2H, m), 6.68 (1H, t), 8.85 (1H, s), 8.35-8.32 (2H, t), 8.09-7.92 (5H, m), 7.62-7.44 1.72 (6H, s) 581.73 581.19

Test Example  One

The HOMO, LUMO and BAND GAP of Compound 38, Compound 66 and Compound 76 were measured by the following method using a CV measuring instrument (manufacturer: princeton appied research, model: Parstat 2273) Are shown in Tables 9 to 11 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 38) -E _ox (NPB)) (eV)
Band gap = 1240 / UV absorption limit (430 nm) (eV) E _ox homo Band gap Rumo NPB 0.72 eV Compound 38 1.10 eV -5.87 eV 2.88 eV -2.99eV

Homo = -5.5- (E _ox (Compound 66) -E _ox (NPB)) (eV)
Band gap = 1240 / UV absorption limit (430 nm) (eV) E _ox homo Band gap Rumo NPB 0.77 eV Compound 66 1.17 eV -5.90 eV 2.88 eV -3.02 eV

Homo = -5.5- (E _ox (Compound 76) -E _ox (NPB)) (eV)
Band gap = 1240 / UV absorption limit (428 nm) (eV) E _ox homo Band gap Rumo NPB 0.79 eV Compound 76 1.17 eV -5.88 eV 2.90 eV -2.98 eV

Figures 4 and 5 show the E _ox values derived from CV measurements of compound 38.

Figures 6 and 7 show the E _ox values derived from CV measurements of compound 66.

Figures 8 and 9 show the E _ox values derived from CV measurements of compound 76.

4 to 9, the y-axis represents current (unit: A) and the x-axis represents potential (unit: V).

On the other hand, Fig. 10 shows a UV measurement graph of Compound 38. Fig.

11 shows a PL measurement graph of Compound 38 at 320 nm.

Figure 12 shows a UV measurement graph of compound 66.

13 shows a PL measurement graph of Compound 66 at 260 nm.

14 shows a UV measurement graph of Compound 76. Fig.

15 shows a PL measurement graph of Compound 76 at 303 nm.

10 to 15 are intensity, and the x-axis is wavelength (unit: nm).

Comparative Example  One: OLED  Device fabrication

First, a transparent electrode ITO thin film obtained from a glass for OLED (manufactured by Samsung Corning) was subjected to ultrasonic cleaning using trichlorethylene, acetone, ethanol, and distilled water sequentially, and washed with isopropyl alcohol before use.

Next, an ITO substrate was placed in a substrate folder of a vacuum deposition apparatus and evacuated until the degree of vacuum in the vacuum evaporation apparatus reached 10 ^-7 torr. Then, 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenyl amine (hereinafter referred to as 2-TNATA) was deposited by vapor phase deposition A 600 Å thick hole injection layer was deposited on the ITO substrate.

Then, another cell in a vacuum deposition apparatus was charged with the following N, N'-bis (α-naphthyl) -N, N'-diphenyl-4,4'- N, N'-diphenyl-4,4'-diamine: hereinafter referred to as NBP) was added to the hole injection layer, and a hole transport layer having a thickness of 250 Å was deposited on the hole injection layer by applying current to the cell.

After the hole injecting layer and the hole transporting layer were formed, a light emitting layer was deposited thereon as follows. A-ADN as a host was put into one cell in a vacuum deposition apparatus, and BD1 as a dopant was placed in another cell.

Then, the light emitting layer was deposited on the hole transport layer to a thickness of 200 ANGSTROM by heating the two cells together and depositing the dopant at a deposition rate ratio of 5 wt% (host: dopant = 95: 5). Subsequently, the following tris (8-hydroxyquinoline) aluminum (III) (hereinafter referred to as Alq ₃ ) was deposited as an electron transporting layer 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 1200 ANGSTROM 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.

Example  One: OLED  Device fabrication

OLEDs were prepared in the same manner as the comparative example except that the compound of Table 12 was used instead of tris (8-hydroxyquinoline) aluminum (III) (Alq ₃ ) as a comparative example as an electron transporting layer material.

Test Example  2: OLED Characterization of

The time until the driving voltage (V), the power efficiency (cd / A) and the driving lifetime of the OLED element manufactured as described above is 1,000 cd / m ² and the efficiency drops to 50% is shown in Table 12 Respectively.

Electron transport layer material Op.V Cd / A T ₅₀ (Hour) Alq ₃ (comparative example) 4.72 3.82 180 Compound 1 4.31 4.54 260 Compound 3 4.31 4.45 290 Compound 6 4.32 4.45 250 Compound 8 4.23 4.51 290 Compound 12 4.3 4.56 310 Compound 13 4.3 4.55 300 Compound 16 4.35 4.49 280 Compound 18 4.22 4.5 300 Compound 28 4.15 5.14 350 Compound 35 4.31 4.44 300 Compound 38 4.22 5.25 320 Compound 39 4.31 4.54 280 Compound 41 4.3 4.55 270 Compound 42 4.33 4.43 300 Compound 44 4.31 4.42 290 Compound 45 4.23 4.51 300 Compound 47 4.31 4.56 310 Compound 51 4.34 4.45 290 Compound 54 4.12 4.62 380 Compound 66 4.31 4.49 260 Compound 76 4.24 4.84 350 Compound 78 4.3 4.55 260 Compound 86 4.31 4.54 260 Compound 87 4.29 4.56 270 Compound 93 4.23 4.51 270 Compound 99 4.32 4.5 280 Compound 102 4.3 4.51 290 Compound 104 4.22 4.53 300 Compound 105 4.31 4.54 270 Compound 110 4.29 4.56 280 Compound 114 4.24 4.59 290 Compound 119 4.23 4.51 320 Compound 123 4.32 4.5 320 Compound 128 4.24 4.51 320 Compound 134 4.25 4.63 340 Compound 136 4.39 4.55 320 Compound 139 4.01 4.68 420 Compound 142 4.35 4.48 300 Compound 144 4.38 4.51 320 Compound 146 4.35 4.53 330 Compound 150 4.11 4.73 380 Compound 152 4.32 4.54 300 Compound 161 4.33 4.43 300 Compound 167 4.32 4.49 280 Compound 171 4.3 4.51 290 Compound 173 4.23 4.51 300 Compound 176 4.32 4.45 310 Compound 179 4.3 4.57 310 Compound 180 4.03 4.63 360 Compound 183 4.32 4.61 280 Compound 185 4.31 4.6 300 Compound 188 4.35 4.51 290 Compound 190 4.2 4.69 340 Compound 194 4.31 4.45 290 Compound 196 4.23 4.51 290 Compound 198 4.3 4.56 310 Compound 202 4.32 4.5 300 Compound 204 4.3 4.55 270 Compound 206 4.35 4.49 270 Compound 208 4.22 4.5 290 Compound 213 4.32 4.5 300 Compound 218 4.23 4.72 310 Compound 228 4.35 4.75 300

From the results of Table 12, it can be seen that, in the case of the organic light emitting device manufactured using the compound of the present invention as an electron transport layer material, the organic light emitting device using tris (8-hydroxyquinoline) aluminum (III) (Alq ₃ ) And excellent characteristics in contrast drive voltage, efficiency, and service life. Thus, it was confirmed that the pyrazole-containing polycyclic ring derivative represented by Formula 1 was useful as an electron transport layer material in the production of an organic light emitting device.

Comparative Example  2: 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 in the substrate folder of the vacuum deposition equipment, and 2-TNATA was placed in the cell in the vacuum deposition equipment.

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 was placed in another cell in a vacuum deposition apparatus, and a current was applied to the cell to evaporate it, thereby depositing a hole transport layer having a thickness of 300 Å on the hole injection layer.

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. (4,4'-bis (carbazol-9-yl) biphenyl) as a green luminescent host material was vacuum deposited on a cell in a vacuum deposition apparatus to a thickness of 350 Å and a green luminescent dopant Ir (ppy) ₃ Tris (2-phenylpyridine) iridium (III)) was vacuum deposited at 10% on 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 was deposited to a thickness of 200 Å Respectively. Thereafter, lithium fluoride was deposited to a thickness of 10 A 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  3: OLED  Device fabrication

The materials shown in Table 13 corresponding to the green light emitting layer in the above Comparative Example were used instead of CBP, and the remaining materials were used in the same manner as in Comparative Example 2 to fabricate the device.

Test Example  4: 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 and when the efficiency drops to 50% is shown in Table 13 below.

The host of the light- Op.V Cd / A T ₅₀ (Hour) Comparative Example 2 (CBP) 6.71 35.3 260 Compound 231 4.63 43.1 400 Compound 236 4.69 45.2 400 Compound 241 4.62 43.1 380 Compound 247 4.64 42.2 410 Compound 250 4.59 42.2 380 Compound 251 4.60 42.8 370 Compound 256 4.61 43.0 370 Compound 271 4.58 42.7 350 Compound 281 4.61 43.0 370 Compound 316 4.58 42.7 350 Compound 321 4.65 42.4 430

From the results of Table 13, it was confirmed that the organic light emitting device manufactured by using the compound of the present invention as a phosphorescent light emitting layer material had superior characteristics in driving voltage, efficiency and lifetime compared with the organic light emitting device using CBP in Comparative Example. Thus, it was confirmed that the pyrazole-containing polycyclic ring derivative represented by formula (I) of the present invention 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: electron transport layer
305: electron injection layer
400: cathode

Claims (17)

Compounds of formula 5:
[Chemical Formula 5]

In Formula 5,
R, and R ₅ to R ₈ are hydrogen,
n is an integer of 1 to 3,
L is C ₆ to C ₆₀ monocyclic or polycyclic arylene; Or a C ₂ to C ₆₀ monocyclic or polycyclic heteroarylene, p is an integer of 0 to 3, and when p is 2 or more, L is the same or different,
Ar is a C ₆ to C ₆₀ monocyclic or polycyclic aryl; Or a C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl, q is an integer of 1 to 3, and when q is 2 or more, Ar is the same or different from each other. delete delete delete delete delete delete delete The compound according to claim 1, wherein L is a pyridine group, a pyrimidine group, a triazine group, an anthracene group, a phenanthrene group, a naphthalene group, or a phenylene group. The compound according to claim 1, wherein Ar is pyridyl, pyrimidyl, triazinyl, anthryl, phenanthryl, naphthyl, or a phenyl group. The compound according to claim 1, wherein the compound of formula (5) is represented by any one of the following formulas (9) to (12):
[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

In the above formulas, R and R ₅ to R ₈ are as defined in formula (5)
X ₁ to X ₃ are the same or different and each independently N or CY ₆ , at least one of X ₁ to X ₃ is N,
Y ₁ to Y ₆ are the same or different from each other, and each independently hydrogen; C ₆ to C ₆₀ monocyclic or polycyclic aryl; Or a C ₂ to C ₆₀ monocyclic or polycyclic heteroaryl,
n is an integer from 1 to 3, r is an integer from 1 to 5, not less than r is 2 and Y ₃ are the same or different from one another, s is an integer from 1 to 7, Y ₄ are each not less than s 2 T is an integer of 1 to 9, and when t is 2 or more, Y < ₅ > are the same or different,
L is C ₆ to C ₆₀ monocyclic or polycyclic arylene; Or a C ₂ to C ₆₀ monocyclic or polycyclic heteroarylene, p is an integer of 0 to 3, and when p is 2 or more, L is the same or different from each other. The compound according to claim 1, wherein the compound of formula 5 is selected from the following formulas:

An organic electroluminescent device comprising a cathode, an anode, and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers comprises an organic electroluminescent material comprising a compound of the general formula (5) according to any one of claims 1 and 9 to 12 device. [14] The organic light emitting device according to claim 13, wherein the organic compound layer comprising the compound of Formula 5 is a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, or an electron injection layer. [14] The organic light emitting device according to claim 13, wherein the organic material layer including the compound of Formula 5 is an electron transport layer. [14] The organic light emitting device according to claim 13, wherein the organic material layer including the compound of Formula 5 is a light emitting layer. 14. The organic light emitting device according to claim 13, wherein the compound of Formula 5 is a phosphorescent host material.

Images