WO2014081131A1 - Organic compound, and organic electro-luminescence device comprising same - Google Patents

Abstract

The present invention relates to an organic compound, which can be used as a material for an organic electro-luminescence device, and to an organic electro-luminescence device comprising same. More particularly, the present invention relates to an organic compound having excellent thermal stability and light-emitting ability, and to an organic electro-luminescence device having improved luminescence efficiency, driving voltage, life span, and so forth by including the organic compound as a material of an organic layer.

Description

Organic compound and organic electroluminescent device comprising the same

The present invention relates to an organic compound that can be used as a material for an organic electroluminescent device and an organic electroluminescent device comprising the same, and more specifically, to include an organic compound having excellent thermal stability and luminescence ability and the organic compound as a material of an organic material layer. The present invention relates to an organic EL device having improved luminous efficiency, driving voltage, and lifetime.

Based on Bernanose's observation of organic thin-film luminescence in the 1950s, the study of organic electroluminescent (EL) devices (hereinafter referred to simply as 'organic EL devices') led to blue electroluminescence using anthracene single crystals in 1965. In 1987, Tang proposed an organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer. Since then, in order to make a high efficiency, long life organic EL device, it has evolved to introduce each characteristic organic material layer in the device, leading to the development of specialized materials used therein.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. In this case, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.

The light emitting material may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to realize a better natural color according to the light emitting color. In addition, in order to increase luminous efficiency through an increase in color purity and energy transfer, a host / dopant system may be used as a light emitting material.

The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times compared to the fluorescence, research on phosphorescent host materials as well as phosphorescent dopants has been conducted.

Hole injection layer, hole transport layer to date. NPB, BCP, Alq ₃ and the like are widely known as the hole blocking layer and the electron transport layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials. In particular, phosphorescent materials having great advantages in terms of efficiency improvement among the light emitting materials include metal complex compounds including Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) _2, and the like. Green and red dopant materials are used, and CBP is a phosphorescent host material.

However, the conventional luminescent materials are good in terms of luminescence properties, but due to low glass transition temperature and very poor thermal stability, they are not satisfactory in terms of lifespan in organic EL devices. Therefore, there is a demand for development of a light emitting material having excellent performance.

It is an object of the present invention to provide a novel organic compound which is excellent in thermal stability due to a high glass transition temperature and can improve the binding force between holes and electrons.

In addition, an object of the present invention is to provide an organic electroluminescent device having improved driving voltage, luminous efficiency and the like by including the novel organic compound.

The present invention provides a compound represented by Formula 1:

Formula 1

In Chemical Formula 1,

R ₁ to R ₅ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C ₁ -C ₄₀ alkyl group, a substituted or unsubstituted C ₂ -C ₄₀ alkenyl group , Substituted or unsubstituted C ₂ -C ₄₀ alkynyl group, substituted or unsubstituted C ₆ -C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ Alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, substituted or unsubstituted C ₃ ~ C ₄₀ A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, Substituted or unsubstituted C _{6 Through} C ₄₀ Aryl boron group, Substituted or unsubstituted C _{6 Through} C ₄₀ Aryl phosphine group, Substituted or unsubstituted C _{6 Through} C ₄₀ Is selected from the group consisting of an aryl phosphine oxide group and a substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group, or may be combined with adjacent groups to form a condensed ring,

However, R ₁ and R ₂ may be condensed together to form a condensed ring represented by one of Formulas 2 to 4, or one of R ₃ to R ₅ may be condensed with an adjacent group to form a condensed ring represented by Formula 5 below. Forming,

Formula 2

Formula 3

Formula 4

Formula 5

R ₆ to R ₁₁ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group , Substituted or unsubstituted C ₂ -C ₄₀ alkynyl group, substituted or unsubstituted C ₆ -C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ Alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, substituted or unsubstituted C ₃ ~ C ₄₀ A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, Substituted or unsubstituted C _{6 Through} C ₄₀ Aryl boron group, Substituted or unsubstituted C _{6 Through} C ₄₀ Aryl phosphine group, Substituted or unsubstituted C _{6 Through} C ₄₀ Is selected from the group consisting of an aryl phosphine oxide group and a substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group, or may be combined with adjacent groups to form a condensed ring,

Ar ₁ is a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, substituted or unsubstituted C ₁ to C ₄₀ Alkyloxy group, substituted or unsubstituted C ₆ to C ₄₀ arylamine group, substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted Or an unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ to C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ to C ₄₀ arylphosphine group, substituted or unsubstituted C ₆ to C ₄₀ arylphosphine oxide group and substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group Selected from the military,

n is an integer from 0 to 4, and if n is an integer from 1 to 4, at least one Ra is each independently deuterium, halogen, cyano, substituted or unsubstituted C ₁ -C ₄₀ alkyl group, substituted or unsubstituted C Alkenyl group of ₂ to C ₄₀ , substituted or unsubstituted alkynyl group of C ₂ to C ₄₀ , substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl of 5 to 40 nuclear atoms Groups, substituted or unsubstituted C ₆ -C ₄₀ aryloxy group, substituted or unsubstituted C ₁ -C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ -C ₄₀ arylamine group, substituted or unsubstituted A substituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl boron group, and an aryl phosphonium substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ of pingi, substituted Combines groups selected from the group consisting of aryl silyl unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted C ₆ ~ C ₄₀ is, or adjacent to form a condensed ring;

X is a single bond or is selected from the group consisting of C (R ₂₁ ) (R ₂₂ ), N (R ₂₃ ), O, and S;

R ₂₁ to R ₂₃ are each independently hydrogen, deuterium, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, or a substituted or unsubstituted nuclear atom 5 to 5 40 heteroaryl group and substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, arylalkyl group, cycloalkyl group, heterocycloalkyl group, alkyl of R ₁ to R _11, Ra and Ar ₁ A silyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, an aryl phosphine oxide group and an aryl silyl group; and one or more substituents respectively introduced to the alkyl, aryl, heteroaryl and arylamine groups of R ₂₁ to R ₂₃ . Are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atom 5 To 40 heteroaryl group, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₄₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom number 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ alkyl group of boron, C ₆ ~ C ₄₀ aryl group of boron, C ₆ ~ C ₄₀ aryl group Is selected from the spin group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group of the group consisting of, wherein if the plurality of substituents, the same or different from each other.

In addition, the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer comprises the compound. Provided is an organic electroluminescent device.

Since the compound represented by Formula 1 of the present invention is excellent in thermal stability and phosphorescence properties, it may be applied to the light emitting layer of the organic EL device.

Therefore, when the compound represented by Chemical Formula 1 of the present invention is used as a phosphorescent host material, an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency and long life compared to the conventional host material can be manufactured, and further, performance In addition, a full color display panel with a greatly improved lifespan can be manufactured.

Hereinafter, the present invention will be described in detail.

The novel compound according to the present invention is a structure in which an indole moiety is fused to a terminal of a pyrroloacridine moiety to form a basic skeleton, and various substituents are bonded to the basic skeleton. It is characterized by represented by the formula (1). The compound represented by the formula (1) has a higher molecular weight than the conventional organic EL device material [for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')], and has a wide energy band gap, The bonding force of the electrons can be increased. Therefore, when the compound of Formula 1 is used in an organic EL device, the driving voltage, efficiency (light emitting efficiency, power efficiency), lifetime, and luminance of the device may be improved.

The compound represented by Chemical Formula 1 may have a wide bandgap in which an indole moiety having a large electron donor is bonded to a terminal of a pyrroloacridine moiety. In addition, the compound has a bipolar characteristic of the entire molecule due to the various aromatic ring substituents in which the electron withdrawal group (EWG) having high electron absorption is bonded to the basic skeleton, and thus the bonding force between the holes and the electrons is improved. It can increase. Therefore, when the compound is applied to the organic EL device, since it can exhibit excellent properties as a host material of the light emitting layer compared to the conventional CBP, the phosphorescence property of the device is improved, and at the same time, the hole injection capacity and / or transport capacity, luminous efficiency, Driving voltage, lifespan characteristics and the like can be improved. In addition, the energy level may be adjusted according to the substituents to have a wide band gap (sky blue to red), and thus may be applied to not only the light emitting layer but also a hole transport layer, a hole injection layer, and the like.

On the other hand, in the phosphorescent layer of the organic EL device, the host material should have a triplet energy gap of the host higher than the dopant. That is, in order to effectively provide phosphorescence from the dopant, the lowest excited state of the host must be higher in energy than the lowest emitted state of the dopant. The compound represented by Formula 1 of the present invention has an indole moiety as a central skeleton and has triplet energy suitable for phosphorescence emission.

In addition, the molecular weight of the compound is significantly increased due to the various aromatic ring substituents introduced into the indole moiety, so that the glass transition temperature can be improved, thereby having higher thermal stability than the conventional CBP. Can be. In addition, by infusing an indole moiety bound to the terminal of the pyrroloacridine moiety, not only the thermal stability of the compound may be improved, but also the compound of Formula 1 It is also effective in suppressing crystallization of the organic layer. Therefore, the device including the compound of formula 1 according to the present invention can greatly improve the durability and life characteristics.

In addition, when the compound of Chemical Formula 1 according to the present invention is adopted as a hole injection / transport layer material of an organic EL device, a phosphorescent host material of blue, green and / or red color, the compound having the excellent efficiency and lifespan may be superior to the conventional CBP. Can be. Therefore, the compound according to the present invention can greatly contribute to improving the performance and lifespan of the organic EL device, and in particular, the device life improvement has a great effect on maximizing the performance in the full color organic light emitting panel.

In the compound represented by Formula 1 according to the present invention, R ₁ to R ₅ are the same as or different from each other, each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, substituted Or an unsubstituted C ₂ -C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ -C ₄₀ aryl group, a substituted or unsubstituted nuclear atom 5 To 40 heteroaryl groups, substituted or unsubstituted C ₆ to C ₄₀ aryloxy groups, substituted or unsubstituted C ₁ to C ₄₀ alkyloxy groups, substituted or unsubstituted C ₆ to C ₄₀ arylamines Groups, substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, substituted or unsubstituted Substituted C ₁ to C ₄₀ alkylboron group, substituted or unsubstituted C ₆ to C ₄₀ arylboron group, substituted or unsubstituted C ₆ to C ₄₀ arylphosphine group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group and substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group selected from the group, or in combination with an adjacent group Condensed rings can be formed.

At this time, the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, arylalkyl group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group of the R ₁ to R ₅ , One or more substituents each introduced into an alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group and an arylsilyl group are each independently deuterium, halogen, cyano group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₄₀ aryl group, nuclear atom 5 to 40 heteroaryl group, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ Alkyloxy group, C ₆ -C ₄₀ arylamine group, C ₃ -C ₄₀ cycloalkyl group, nuclear atom 3-40 heterocycloalkyl group, C ₁ -C ₄₀ alkylsilyl group, C ₁ -C ₄₀ boron alkyl group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group Doedoe selected from the group consisting of, in the case where the substituent a plurality, may be identical to or different from each other.

However, R ₁ and R ₂ may be fused to each other in R ₁ to R ₅ to form a fused ring represented by one of Formulas 2 to 4, or one of R ₃ to R ₅ may be adjacent to each other. It should be combined with the group to form a condensed ring represented by the formula (5). For example, when R ₃ is condensed with an adjacent group R _{4 in} the R ₁ to R ₅ to form a condensed ring represented by Chemical Formula 5, a compound represented by the following Chemical Formula 6 or 8 is formed. Alternatively, when R ₁ and R ₂ are condensed in the R ₁ to R ₅ to form a condensed ring represented by one of Formulas 2 to 4, a compound represented by one of Formulas 10 to 15 is formed.

In Chemical Formulas 2 to 5, the dotted line refers to a site where condensation occurs with the compound of Chemical Formula 1.

R ₆ to R ₁₁ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C ₁ -C ₄₀ alkyl group, a substituted or unsubstituted C ₂ -C ₄₀ alkene Nyl group, substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ Alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl groups, substituted or unsubstituted heterocycloalkyl groups having 3 to 40 nuclear atoms, substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl groups, substituted or unsubstituted C ₁ to C ₄₀ alkylboron groups , Substituted or unsubstituted C ₆ ~ C ₄₀ arylboron group, substituted or unsubstituted C ₆ ~ C ₄₀ arylphosphine group, substituted or unsubstituted C It may be selected from the group consisting of ₆ ~ C ₄₀ aryl phosphine oxide group and substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group, or may be combined with adjacent groups to form a condensed ring.

At this time, the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, arylalkyl group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group of R ₆ to R ₁₁ , One or more substituents each introduced into an alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group and an arylsilyl group are each independently deuterium, halogen, cyano group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₄₀ aryl group, nuclear atom 5 to 40 heteroaryl group, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ Alkyloxy group, C ₆ -C ₄₀ arylamine group, C ₃ -C ₄₀ cycloalkyl group, nuclear atom 3-40 heterocycloalkyl group, C ₁ -C ₄₀ alkylsilyl group, C ₁ -C ₄₀ boron alkyl group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group It is selected from the group consisting. However, when there are a plurality of substituents, they may be the same or different from each other.

Ar ₁ is a substituted or unsubstituted C ₁ ~ C ₄₀ Alkyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ Alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ Alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ An alkyloxy group, a substituted or unsubstituted C ₆ -C ₄₀ arylamine group, a substituted or unsubstituted C ₃ -C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, Substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, substituted or unsubstituted C ₆ to C ₄₀ arylboron group, substituted or unsubstituted aryl silyl group of C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted C ₆ ~ C ₄₀ is Is selected from the group eojin, and preferably may be selected from substituted or unsubstituted aryl group of C ₆ ~ C ₄₀ ring, and a substituted or unsubstituted hetero group, the aryl ring of the number of nuclear atoms of 5 to 40.

In this case, an alkyl group, an alkenyl group, an alkynyl group, an aryl group of said Ar _1, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an aryl group, a cycloalkyl group, a heterocycloalkyl group, alkylsilyl group, an alkyl boronic group , At least one substituent introduced into each of the aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group is each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenes group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C ₆ ~ C _40, alkyloxy group of C ₁ ~ C ₄₀ of the , C ₆ -C ₄₀ arylamine group, C ₃ -C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group , C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl group made of the silyl It is selected from the group true. However, when there are a plurality of substituents, they may be the same or different from each other.

In the compound of Formula 1, n is an integer of 0 to 4. When n is 0, it means that hydrogen is not substituted by the substituent Ra. In addition, when n is an integer of 1 to 4, hydrogen is substituted with a substituent Ra, and at least one Ra is each independently deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or Unsubstituted C ₂ to C ₄₀ alkenyl group, substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted nuclear atom 5 to 5 40 heteroaryl groups, substituted or unsubstituted C ₆ -C ₄₀ aryloxy groups, substituted or unsubstituted C ₁ -C ₄₀ alkyloxy groups, substituted or unsubstituted C ₆ -C ₄₀ arylamine groups , Substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl boron group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, substituted or unsubstituted C ₆ ~ C ₄₀ A arylphosphine group, a substituted or unsubstituted C ₆ -C ₄₀ arylphosphine oxide group, and a substituted or unsubstituted C ₆ -C ₄₀ arylsilyl group, or a condensed ring in combination with an adjacent group Can be formed.

At this time, the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group of the Ra, arylalkyl group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, One or more substituents introduced into the arylborone group, the arylphosphine group, the arylphosphine oxide group and the arylsilyl group are each independently deuterium, halogen, cyano group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group , C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C ₆ ~ C _40, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₄₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl group in the silyl done It is selected from the group. However, when there are a plurality of substituents, they may be the same or different from each other.

X is a single bond directly connected or is selected from the group consisting of C (R ₂₁ ) (R ₂₂ ), N (R ₂₃ ), O and S, preferably a single bond, or C (R ₂₁ ) ( R ₂₂ ).

R ₂₁ to R ₂₃ are each independently hydrogen, deuterium, a substituted or unsubstituted C ₁ -C ₄₀ alkyl group, a substituted or unsubstituted C ₆ -C ₄₀ aryl group, a substituted or unsubstituted nuclear atom 5 To 40 heteroaryl groups, and a substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group. According to an example of the present invention, when X is C (R ₂₁ ) (R ₂₂ ), R ₂₁ and R ₂₂ are hydrogen, a substituted or unsubstituted C ₁ -C ₄₀ alkyl group, or a substituted or unsubstituted group. preferably C ₆ ~ C ₄₀ aryl group in it, and it is more preferred that the methyl group or a phenyl group.

At this time, one or more substituents introduced into each of the alkyl group, aryl group, heteroaryl group and arylamine group of R ₂₁ to R ₂₃ are each independently deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₄₀ aryl group, nuclear atom 5 to 40 heteroaryl group, C ₆ to C ₄₀ aryloxy group, C ₁ to C ₄₀ Alkyloxy group, C ₆ -C ₄₀ arylamine group, C ₃ -C ₄₀ cycloalkyl group, nuclear atom 3-40 heterocycloalkyl group, C ₁ -C ₄₀ alkylsilyl group, C ₁ -C ₄₀ alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ is selected from an aryl silyl group the group consisting of C ₄₀ . However, when there are a plurality of substituents, they may be the same or different from each other.

In the compound of Formula 1 according to the present invention, preferably R ₁ to R _11, Ra and Ar ₁ may be each independently selected from the group consisting of hydrogen or the following substituents S1 to S206, but is not limited thereto.

In the compound of Formula 1, Ar ₁ may be preferably selected from the group consisting of the following substituents A1 to A64.

Examples of the compound represented by Formula 1 according to the present invention include a compound represented by the following Formulas 6 to 15, but are not limited thereto.

Formula 6

Formula 7

Formula 8

Formula 9

Formula 10

Formula 11

Formula 12

Formula 13

Formula 14

Formula 15

In Chemical Formulas 6 to 15,

R ₁ to R ₁₁ , Ra, Ar _1, X and n are the same as defined in Chemical Formula 1.

Specific examples of the compound represented by Formula 1 include compounds represented by the following formulas INV-1 to INV-20, but are not limited thereto.

In Chemical Formulas INV-1 to INV-20,

R ₁ to R ₁₁ , Ra, Ar ₁ and n are the same as defined in Chemical Formula 1.

Representative examples of the compound represented by Formula 1 include the following compounds, but are not limited thereto.

As used herein, "unsubstituted alkyl" is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso -Amyl, hexyl and the like.

In the present invention, "unsubstituted alkenyl" is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon double bond, and examples thereof include vinyl. (vinyl), allyl, isopropenyl, 2-butenyl, and the like, but are not limited thereto.

In the present invention, "unsubstituted alkynyl" is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon triple bond, and examples thereof include eta. Ethynyl, 2-propynyl, and the like, but are not limited thereto.

In addition, in the present invention, "unsubstituted aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. Two or more rings may be attached in a simple or fused form with one another. Examples of aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

In addition, in the present invention, "unsubstituted heteroaryl" means a monovalent substituent derived from monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. It is understood that two or more rings may be attached in a simple or fused form to each other and further include a condensed form with an aryl group. Examples of heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl It is understood to include a ring and to include 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.

In the present invention, "unsubstituted aryloxy" is a monovalent substituent represented by RO-, wherein R is aryl having 5 to 60 carbon atoms. Examples of aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.

In the present invention, "unsubstituted alkyloxy" is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl, and is linear, branched or cyclic. It is interpreted as including a (cyclic) structure. Examples of alkyloxy may include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

In addition, in the present invention, "unsubstituted arylamine" means an amine substituted with aryl having 6 to 60 carbon atoms.

In the present invention, "unsubstituted cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

In the present invention, "unsubstituted heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons Substituted with a hetero atom such as N, O or S. Non-limiting examples thereof include morpholine, piperazine and the like.

In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 40 carbon atoms.

In the present invention, "fused ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

Compounds of formula 1 of the present invention can be synthesized according to general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995) ) And so on). Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.

On the other hand, the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1), preferably a compound represented by the formula (6) to a compound represented by the formula (15).

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer The compound represented by Chemical Formula 1, preferably, the compound represented by Chemical Formula 6 to the compound represented by Chemical Formula 15 is included. In this case, the compound of Formula 1 may be used alone or in combination of two or more.

The at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, at least one of the organic material layer may include a compound represented by the formula (1). Preferably, the organic material layer including the compound of Compound 1 may be a light emitting layer.

According to one embodiment of the present invention, the light emitting layer of the organic electroluminescent device may include a host material, wherein the host material may include the compound of formula (1). As such, when the compound of Formula 1 is included as a light emitting layer material of the organic electroluminescent device, preferably a blue, green or red phosphorescent host, the binding force between holes and electrons in the light emitting layer is increased, so that the efficiency of the organic electroluminescent device (Luminescence efficiency and power efficiency), lifetime, brightness and driving voltage can be improved.

The structure of the organic EL device according to the present invention described above is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. In this case, at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably the light emitting layer comprises a compound represented by the formula (1) Can be. In particular, when the light emitting layer includes the compound of Formula 1, the compound may be used as a phosphorescent host. An electron injection layer may be further stacked on the electron transport layer.

In addition, the structure of the organic electroluminescent device according to the present invention may be a structure in which an anode, one or more organic material layers and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.

The organic electroluminescent device according to the present invention is formed by using materials and methods known in the art, except that at least one layer (eg, a light emitting layer) of the organic material layer is formed to include the compound represented by Chemical Formula 1. It may be prepared by forming another organic layer and an electrode.

The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

The substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.

In addition, examples of the anode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.

The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like.

Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following examples are merely to illustrate the invention, the present invention is not limited by the following examples.

Preparation Example 1 Synthesis of Compound IC-1

<Step 1> Synthesis of methyl 2- (4-bromo-1H-indol-1-yl) benzoate

4-bromo-1H-indole (24.3 g, 0.124 mol), methyl 2-iodobenzoate (97.5 g, 0.372 mmol), Cu powder (1.5 g, 24.8 mmol), K ₂ CO ₃ (34.2 g, 0.248 mmol) under nitrogen stream ), Na ₂ SO ₄ (35.3 g, 0.248 mmol) and nitrobenzene (1000 ml) were mixed and then stirred at 190 ° C. for 12 hours.

After the reaction was completed, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . Thereafter, the solvent of the organic layer was removed and purified by column chromatography to obtain methyl 2- (4-bromo-1H-indol-1-yl) benzoate (26.6 g, 80.6 mmol, yield: 65%).

¹ H-NMR: δ 3.83 (s, 3H), 6.52 (d, 1H), 7.23 (m, 2H), 7.31 (d, 1H), 7.53 (m, 2H), 7.76 (m, 3H)

Step 2 Synthesis of 3-bromo-6,6-dimethyl-6H-pyrrolo [3,2,1-de] acridine

Under nitrogen stream, methyl 2- (4-bromo-1H-indol-1-yl) benzoate (23.1 g, 70.0 mmol) obtained in <Step 1> of Preparation Example 1 was added to ether (250 ml), and the temperature was −. After maintaining at 78 ° C., Methyl lithium (1.6 M in ether, 110 ml, 0.175 mol) was added thereto, followed by stirring for 1 hour, followed by further stirring at room temperature for 4 hours. After the reaction was terminated, the organic layer was separated with methylene chloride, and then water was removed from the organic layer using MgSO ₄ . Thereafter, the solvent was removed from the organic layer, and then purified by column chromatography to obtain an intermediate compound.

Subsequently, the intermediate compound was added to phosphoric acid (150 ml), stirred at room temperature for 6 hours, the organic layer was separated using methylene chloride and water, and then water was removed from the organic layer using MgSO ₄ , and recrystallized from ethanol. 3-bromo-6,6-dimethyl-6H-pyrrolo [3,2,1-de] acridine (13.5 g, 43.4 mmol, yield: 62%) was obtained.

¹ H-NMR: δ 1.73 (s, 6H), 6.52 (d, 1H), 6.85 (d, 1H), 7.09 (d, 1H), 7.31 (m, 4H), 7.63 (d, 1H)

Step 3 Synthesis of 6,6-dimethyl-3- (2-nitrophenyl) -6H-pyrrolo [3,2,1-de] acridine

3-bromo-6,6-dimethyl-6H-pyrrolo [3,2,1-de] acridine (2.75 g, 8.80 mmol) obtained in <Step 2> of Preparation Example 1 under nitrogen stream, 2-nitrophenylboronic acid (1.61 g, 9.67 mmol), NaOH (1.06 g, 26.37 mmol) and THF / H ₂ O (100 ml / 50 ml) were mixed and stirred. Thereafter, Pd (PPh ₃ ) ₄ (0.51 g, 5 mol%) was added to the mixture at 40 ° C., and stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. The solvent was removed from the filtered organic layer, and then 6,6-dimethyl-3- (2-nitrophenyl) -6H-pyrrolo [3,2,1-de] acridine (2.56 g, 7.22 mmol, yield using column chromatography). : 82%).

¹ H-NMR: δ 1.73 (s, 6H), 6.52 (d, 1H), 7.01 (d, 1H), 7.33 (m, 4H), 7.60 (m, 2H), 7.99 (m, 4H)

Step 4 Synthesis of Compound IC-1

6,6-dimethyl-3- (2-nitrophenyl) -6H-pyrrolo [3,2,1-de] acridine (2.56 g, 7.22 mmol) obtained in <Step 3> of Preparation Example 1 under nitrogen stream, triphenylphosphine ( 4.73 g, 18.05 mmol) and 1,2-dichlorobenzene (30 ml) were added thereto, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed and the organic layer was extracted with dichloromethane. Water was removed from the extracted organic layer with MgSO ₄ , and compound IC-1 (1.79 g, 5.56 mmol, yield: 77%) was obtained by column chromatography.

¹ H-NMR: δ 1.73 (s, 6H), 6.52 (d, 1H), 7.33 (m, 5H), 7.60 (m, 3H), 8.00 (s, 1H), 8.11 (d, 1H), 9.94 ( s, 1 H)

Preparation Example 2 Synthesis of Compound IC-2 and Compound IC-3

<Step 1> Synthesis of methyl 2- (5-bromo-1H-indol-1-yl) benzoate

<Step 1> of Preparation Example 1, except that 5-bromo-1H-indole (24.3 g, 0.124 mol) was used instead of 4-bromo-1H-indole used in <Step 1> of Preparation Example 1 The same procedure was followed to obtain methyl 2- (5-bromo-1H-indol-1-yl) benzoate.

¹ H-NMR: δ 3.83 (s, 3H), 6.52 (d, 1H), 7.26 (m, 2H), 7.53 (m, 2H), 7.77 (m, 4H)

Step 2 Synthesis of 4-bromo-6,6-dimethyl-6H-pyrrolo [3,2,1-de] acridine

In place of methyl 2- (4-bromo-1H-indol-1-yl) benzoate used in <Step 2> of Preparation Example 1, methyl 2- (5-bromo-1H-indol-1-yl) benzoate (23.1 g, Except for using 70.0 mmol), 4-bromo-6,6-dimethyl-6H-pyrrolo [3,2,1-de] acridine was obtained in the same manner as in <Step 2> of Preparation Example 1. .

¹ H-NMR: δ 1.73 (s, 6H), 6.52 (d, 1H), 7.12 (s, 1H), 7.33 (m, 4H), 7.56 (m, 2H)

Step 3 Synthesis of 6,6-dimethyl-4- (2-nitrophenyl) -6H-pyrrolo [3,2,1-de] acridine

4-bromo-6,6-dimethyl-6H-pyrrolo [3 instead of 3-bromo-6,6-dimethyl-6H-pyrrolo [3,2,1-de] acridine used in <Step 3> of Preparation Example 1 Except for using 2,1-de] acridine (2.75 g, 8.80 mmol), the same procedure as in <Step 3> of Preparation Example 1 was carried out to give 6,6-dimethyl-4- (2-nitrophenyl) -6H-pyrrolo [3,2,1-de] acridine was obtained.

¹ H-NMR: δ 1.73 (s, 6H), 6.52 (d, 1H), 7.33 (m, 4H), 7.60 (m, 3H), 8.01 (m, 3H), 8.46 (s, 1H)

Step 4 Synthesis of Compound IC-2 and Compound IC-3

6,6-dimethyl-4- (2- instead of 6,6-dimethyl-3- (2-nitrophenyl) -6H-pyrrolo [3,2,1-de] acridine used in <Step 4> of Preparation Example 1 Except for using nitrophenyl) -6H-pyrrolo [3,2,1-de] acridine (5.12 g, 14.44 mmol), the compound IC-2 and the same procedure as in <Step 4> of Preparation Example 1 Compound IC-3 was obtained.

¹ H-NMR of compound IC-2: δ 1.73 (s, 6H), 6.52 (d, 1H), 7.33 (m, 6H), 7.58 (m, 3H), 8.12 (d, 1H), 9.94 (s, 1H)

¹ H-NMR of compound IC-3: δ 1.73 (s, 6H), 6.52 (d, 1H), 7.33 (m, 5H), 7.58 (m, 3H), 8.12 (d, 1H), 8.32 (s, 1H), 9.94 (s, 1H)

Preparation Example 3 Synthesis of Compound IC-4

<Step 1> Synthesis of methyl 2- (6-bromo-1H-indol-1-yl) benzoate

<Step 1> of Preparation Example 1, except that 6-bromo-1H-indole (24.3 g, 0.124 mol) instead of 4-bromo-1H-indole used in <Step 1> of Preparation Example 1 The same procedure was followed to obtain methyl 2- (6-bromo-1H-indol-1-yl) benzoate.

¹ H-NMR: δ 3.83 (s, 3H), 6.52 (d, 1H), 7.23 (m, 2H), 7.56 (m, 2H), 7.81 (m, 2H), 8.32 (s, 1H), 8.75 ( s, 1 H)

Step 2 Synthesis of 5-bromo-6,6-dimethyl-6H-pyrrolo [3,2,1-de] acridine

Methyl 2- (6-bromo-1H-indol-1-yl) benzoate (23.1 g, instead of methyl 2- (4-bromo-1H-indol-1-yl) benzoate used in <Step 2> of Preparation Example 1 Except for using 70.0 mmol), 5-bromo-6,6-dimethyl-6H-pyrrolo [3,2,1-de] acridine was obtained in the same manner as in <Step 2> of Preparation Example 1. .

¹ H-NMR: δ 1.73 (s, 6H), 6.52 (d, 1H), 7.10 (d, 1H), 7.33 (m, 4H), 7.60 (d, 1H), 8.13 (d, 1H)

Step 3 Synthesis of 6,6-dimethyl-5- (2-nitrophenyl) -6H-pyrrolo [3,2,1-de] acridine

5-bromo-6,6-dimethyl-6H-pyrrolo [3 instead of 3-bromo-6,6-dimethyl-6H-pyrrolo [3,2,1-de] acridine used in <Step 3> of Preparation Example 1 2,1-de] acridine (2.75 g, 8.80 mmol) was subjected to the same procedure as in <Step 3> of Preparation Example 1 to give 6,6-dimethyl-5- (2-nitrophenyl) -6H-pyrrolo [3,2,1-de] acridine was obtained.

¹ H-NMR: δ 1.73 (s, 6H), 6.52 (d, 1H), 7.33 (m, 4H), 7.60 (m, 2H), 8.00 (m, 4H), 8.29 (d, 1H)

Step 4 Synthesis of Compound IC-4

6,6-dimethyl-5- (2- instead of 6,6-dimethyl-3- (2-nitrophenyl) -6H-pyrrolo [3,2,1-de] acridine used in <Step 4> of Preparation Example 1 Compound IC-4 was prepared by the same procedure as in <Step 4> of Preparation Example 1, except that nitrophenyl) -6H-pyrrolo [3,2,1-de] acridine (2.56 g, 7.22 mmol) was used. Got it.

¹ H-NMR: δ 1.73 (s, 6H), 6.52 (d, 1H), 7.32 (m, 6H), 7.59 (m, 3H), 8.12 (d, 1H), 9.94 (s, 1H)

Preparation Example 4 Synthesis of Compound IC-5

Step 1 Synthesis of 3-bromopyrrolo [3,2,1-jk] carbazole

4,7-dibromo-1H-indole (24.2 g, 88.0 mmol), 2-bromophenylboronic acid (19.4 g, 96.7 mmol), NaOH (10.6 g, 263.7 mmol) and THF / H ₂ O (1000 ml /) under nitrogen stream 500 ml) were mixed and then stirred. Thereafter, Pd (PPh ₃ ) ₄ (5.1 g, 5 mol%) was added to the mixture at 40 ° C., followed by stirring at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent from the filtered organic layer, the intermediate compound 4-bromo-7- (2-bromophenyl) -1H-indole was obtained by column chromatography.

The intermediate compound 4-bromo-7- (2-bromophenyl) -1H-indole 4-bromo-1H-indole (13.0 g, 0.037 mol), Cu powder (0.45 g, 7.44 mmol), K ₂ CO ₃ (10.3 g, 0.074 mmol), Na ₂ SO ₄ (10.6 g, 0.074 mmol) and nitrobenzene (300 ml) were mixed, followed by stirring at 190 ° C. for 12 hours. After the reaction was completed, nitrobenzene was removed, the organic layer was separated with methylene chloride, and then water was removed from the organic layer using MgSO ₄ . The solvent was removed from the organic layer, and then purified by column chromatography to obtain 3-bromopyrrolo [3,2,1-jk] carbazole (8.32 g, 30.8 mmol, yield: 35%).

¹ H-NMR: δ 6.45 (d, 1H), 7.30 (m, 3H), 7.56 (m, 2H), 8.05 (m, 2H)

Step 2 Synthesis of 3- (2-nitrophenyl) pyrrolo [3,2,1-jk] carbazole

3-bromopyrrolo [3,2,1-jk] carbazole (2.38 instead of 3-bromo-6,6-dimethyl-6H-pyrrolo [3,2,1-de] acridine used in <Step 3> of Preparation Example 1 g, 8.80 mmol), except that 3-, 2-nitrophenyl) pyrrolo [3,2,1-jk] carbazole was obtained in the same manner as in <Step 3> of Preparation Example 1.

¹ H-NMR: δ 6.45 (d, 1H), 7.28 (m, 2H), 7.56 (m, 3H), 7.79 (d, 1H), 7.98 (m, 3H), 8.14 (m, 2H)

Step 3 Synthesis of Compound IC-5

3- (2-nitrophenyl) pyrrolo [3, instead of 6,6-dimethyl-3- (2-nitrophenyl) -6H-pyrrolo [3,2,1-de] acridine used in <Step 4> of Preparation Example 1 Except for using 2,1-jk] carbazole (4.51 g, 14.44 mmol), Compound IC-5 was obtained by the same procedure as <Step 4> of Preparation Example 1.

¹ H-NMR: δ 6.45 (d, 1H), 7.28 (m, 3H), 7.57 (m, 5H), 8.12 (m, 2H), 9.94 (s, 1H)

Preparation Example 5 Synthesis of Compounds IC-6 and IC-7

Step 1 Synthesis of 2-bromopyrrolo [3,2,1-jk] carbazole

Except for using 5,7-dibromo-1H-indole (24.2 g, 88.0 mmol) instead of 4,7-dibromo-1H-indole used in <step 1> of Preparation Example 1, < The procedure of step 1> was followed to yield 2-bromopyrrolo [3,2,1-jk] carbazole.

¹ H-NMR: δ 6.45 (d, 1H), 7.28 (m, 2H), 7.59 (m, 3H), 8.09 (m, 2H)

<Step 2> Synthesis of 2- (2-nitrophenyl) pyrrolo [3,2,1-jk] carbazole

Instead of 3-bromo-6,6-dimethyl-6H-pyrrolo [3,2,1-de] acridine used in <Step 3> of Preparation Example 1, 2-bromopyrrolo [3,2,1-jk] carbazole (2.38 g, 8.80 mmol) was used in the same manner as in <Step 3> of Preparation Example 1 to obtain 2- (2-nitrophenyl) pyrrolo [3,2,1-jk] carbazole.

¹ H-NMR: δ 6.45 (d, 1H), 7.28 (m, 3H), 7.62 (m, 3H), 7.83 (m, 2H), 8.03 (m, 2H), 8.11 (d, 1H)

Step 3 Synthesis of Compounds IC-6 and IC-7

2- (2-nitrophenyl) pyrrolo [3, instead of 6,6-dimethyl-3- (2-nitrophenyl) -6H-pyrrolo [3,2,1-de] acridine used in <Step 4> of Preparation Example 1 Except for using 2,1-jk] carbazole (4.51 g, 14.44 mmol), the same procedure as in <Step 4> of Preparation Example 1 was carried out to obtain Compound IC-6 and Compound IC-7.

¹ H-NMR of compound IC-6: δ 6.45 (d, 1H), 7.09 (s, 1H), 7.28 (m, 3H), 7.59 (m, 4H), 8.12 (m, 2H), 9.94 (s, 1H)

¹ H-NMR of compound IC-7: δ 6.45 (d, 1H), 7.28 (m, 3H), 7.58 (m, 5H), 8.12 (m, 2H), 9.94 (s, 1H)

Preparation Example 6 Synthesis of Compound IC-8

Step 1 Synthesis of 1-bromopyrrolo [3,2,1-jk] carbazole

6,7-dibromo-1H-indole (24.2 g, 88.0 mmol) was used instead of 4,7-dibromo-1H-indole used in <Step 1> of Preparation Example 4, and < 1-bromopyrrolo [3,2,1-jk] carbazole was obtained in the same manner as in step 1>.

¹ H-NMR: δ 6.45 (d, 1H), 7.30 (m, 3H), 7.56 (m, 3H), 8.11 (d, 1H)

Step 2 Synthesis of 1- (2-nitrophenyl) pyrrolo [3,2,1-jk] carbazole

1-bromopyrrolo [3,2,1-jk] carbazole (2.38 instead of 3-bromo-6,6-dimethyl-6H-pyrrolo [3,2,1-de] acridine used in <Step 3> of Preparation Example 1 g, 8.80 mmol) was used in the same manner as in <Step 3> of Preparation Example 1 to obtain 1- (2-nitrophenyl) pyrrolo [3,2,1-jk] carbazole.

¹ H-NMR: δ 6.45 (d, 1H), 7.28 (m, 2H), 7.50 (m, 1H), 7.72 (m, 4H), 8.01 (m, 4H)

Step 3 Synthesis of Compound IC-8

1- (2-nitrophenyl) pyrrolo [3, instead of 6,6-dimethyl-3- (2-nitrophenyl) -6H-pyrrolo [3,2,1-de] acridine used in <Step 4> of Preparation Example 1 Except for using 2,1-jk] carbazole (4.51 g, 14.44 mmol), Compound IC-8 was obtained by the same procedure as <Step 4> of Preparation Example 1.

¹ H-NMR: δ 6.45 (d, 1H), 7.08 (s, 1H), 7.28 (m, 3H), 7.56 (m, 4H), 8.12 (m, 2H), 9.94 (s, 1H)

Preparation Example 7 Synthesis of Compounds IC-9 and IC-10

Step 1 Synthesis of 8,8-dimethyl-8H-indolo [3,2,1-de] acridin-3-amine

Under nitrogen stream, 3-bromo-8,8-dimethyl-8H-indolo [3,2,1-de] acridine (10.9 g, 30.0 mmol) was dissolved in THF (100 ml), followed by 28% aqueous ammonia (10.2). ml, 150 mmol) and Cu power (0.10 g, 5 mol%) were added thereto, followed by stirring at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer, 8,8-dimethyl-8H-indolo [3,2,1-de] acridin-3-amine (7.25 g, 24.3 mmol, yield: 81%) was purified using column chromatography. Got it.

¹ H-NMR: δ 1.73 (s, 6H), 6.24 (s, 2H), 6.78 (d, 1H), 7.32 (m, 6H), 7.65 (m, 2H), 7.94 (d, 1H) -2

Step 2 Synthesis of Compounds IC-9 and IC-10

Dissolve 8,8-dimethyl-8H-indolo [3,2,1-de] acridin-3-amine (5.97 g, 20.0 mmol) in H ₂ O / dioxane (10 ml / 90 ml) under a stream of nitrogen, put triethanolammonium chloride (0.372 g, 2 mmol ), RuCln-H 2 O (0.052 g, 0.2 mmol), PPh 3 (0.158 g, 0.6 mmol), and _{SnCl 2- 2H 2 O (0.452 g} , 2 mmol), Stir at 180 ° C. for 20 hours. After completion of the reaction, the reaction was poured into 5% aqueous HCl solution, extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent from the filtered organic layer using column chromatography to give the compound IC-9 (1.74 g, 5.4 mmol, yield: 27%) and compound IC-10 (1.75 g, 5.4 mmol, yield: 27%).

¹ H-NMR of compound IC-9: δ 1.73 (s, 6H), 6.43 (d, 1H), 6.95 (d, 1H), 7.17 (m, 1H), 7.32 (m, 6H), 7.56 (s, 1H), 8.37 (d, 1H), 9.94 (s, 1H)

¹ H-NMR of compound IC-10: δ 1.73 (s, 6H), 6.43 (d, 1H), 6.95 (d, 1H), 7.17 (m, 1H), 7.35 (m, 6H), 7.63 (d, 1H), 8.37 (d, 1H), 9.94 (s, 1H)

Preparation Example 8 Synthesis of Compounds IC-11 and IC-12

Step 1 Synthesis of 4- (5-bromo-2-nitrophenyl) -6,6-dimethyl-6H-pyrrolo [3,2,1-de] acridine

The same process as in <Step 3> of Preparation Example 2, except that 5-bromo-2-nitrophenylboronic acid (2.38 g, 9.67 mmol) was used instead of 2-nitrophenylboronic acid used in <Step 3> of Preparation Example 2. Was carried out to obtain 4- (5-bromo-2-nitrophenyl) -6,6-dimethyl-6H-pyrrolo [3,2,1-de] acridine.

¹ H-NMR: δ 1.71 (s, 6H), 6.54 (d, 1H), 7.34 (m, 4H), 7.60 (m, 2H), 7.74 (s, 1H), 7.98 (d, 1H), 8.24 ( m, 2H)

Step 2 Synthesis of Compounds IC-11 and IC-12

4- (5-bromo-2-nitrophenyl) instead of 6,6-dimethyl-3- (2-nitrophenyl) -6H-pyrrolo [3,2,1-de] acridine used in <Step 4> of Preparation Example 1 Except for using -6,6-dimethyl-6H-pyrrolo [3,2,1-de] acridine (6.26 g, 14.44 mmol), the compound was carried out in the same manner as in <Step 4> of Preparation Example 1 IC-11 and IC-12 were obtained.

¹ H-NMR of compound IC-11: δ 1.73 (s, 6H), 6.52 (d, 1H), 7.32 (m, 6H), 7.59 (m, 2H), 8.05 (s, 1H), 10.19 (s, 1H)

¹ H-NMR of compound IC-12: δ 1.74 (s, 6H), 6.53 (d, 1H), 7.33 (m, 7H), 8.05 (s, 1H), 8.31 (s, 1H), 10.16 (s, 1H)

Preparation Example 9 Synthesis of Compounds IC-13 and IC-14

Synthesis of 2- (5-bromo-2-nitrophenyl) pyrrolo [3,2,1-jk] carbazole

Instead of 3-bromopyrrolo [3,2,1-jk] carbazole used in <Step 2> of Preparation Example 4, 2-bromopyrrolo [3,2,1-jk] carbazole (2.38 g, 8.80 mmol) was used. Except for using 5-bromo-2-nitrophenylboronic acid (2.38 g, 9.67 mmol) instead of -nitrophenylboronic acid, 2- (5-bromo-2- was carried out in the same manner as in <Step 2> of Preparation Example 4 nitrophenyl) pyrrolo [3,2,1-jk] carbazole was obtained.

¹ H-NMR: δ 6.44 (d, 1H), 7.31 (m, 3H), 7.54 (m, 2H), 7.72 (m, 2H), 7.98 (d, 1H), 8.21 (m, 2H)

Step 2 Synthesis of Compounds IC-13 and IC-14

2- (5-bromo-2-nitrophenyl) instead of 6,6-dimethyl-3- (2-nitrophenyl) -6H-pyrrolo [3,2,1-de] acridine used in <Step 4> of Preparation Example 1 Except for using pyrrolo [3,2,1-jk] carbazole (5.65 g, 14.44 mmol), the compound IC-13 and IC-14 were obtained by the same procedure as the <Step 4> of Preparation Example 1 .

¹ H-NMR of compound IC-13: δ 6.43 (d, 1H), 7.08 (s, 1H), 7.29 (m, 2H), 7.49 (m, 4H), 8.06 (m, 2H), 10.21 (s, 1H)

¹ H-NMR of compound IC-14: δ 6.44 (d, 1H), 7.27 (m, 2H), 7.50 (m, 5H), 8.08 (m, 2H), 10.20 (s, 1H)

Synthesis Example 1 Synthesis of Compound C-1

Compound IC-1 (4.28 g, 13.29 mmol), synthesized in Preparation Example 1 under nitrogen stream, 2- (4-bromophenyl) triphenylene (10.18 g, 26.57 mmol), Cu powder (0.17 g, 2.66 mmol), K ₂ CO ₃ (3.66 g, 26.57 mmol), Na ₂ SO ₄ (3.78 g, 26.57 mmol) and nitrobenzene (100 ml) were mixed and then stirred at 190 ° C. for 12 hours.

After the reaction was completed, nitrobenzene was removed and the organic layer was separated with methylene chloride, and then water was removed from the organic layer using MgSO ₄ . Then, the solvent was removed from the organic layer, and then purified by column chromatography to give the compound C-1 (5.23 g, yield: 63%).

GC-Mass (Theoretical value: 624.77 g / mol, Measured value: 624 g / mol)

Synthesis Example 2 Synthesis of Compound C-2

Synthesis Example 1 except that 4- (4-bromophenyl) -6-phenyldibenzo [b, d] thiophene (11.02 g, 26.57 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1. Compound C-2 (5.06 g, yield: 58%) was obtained by the same process as the same procedure.

GC-Mass (Theoretical value: 656.84 g / mol, Measured value: 656 g / mol)

Synthesis Example 3 Synthesis of Compound C-3

Compound C-3 was prepared by the same procedure as in Synthesis Example 1, except that 2-bromo-6-phenylpyridine (6.19 g, 26.57 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1. (4.42 g, yield: 70%) was obtained.

GC-Mass (Theoretical value: 475.58 g / mol, Measured value: 475 g / mol)

Synthesis Example 4 Synthesis of Compound C-4

Compound IC-1 (1.89 g, 5.85 mmol) synthesized in Preparation Example 1 under nitrogen stream was prepared using 2-chloro-4,6-diphenylpyrimidine (2.09 g, 7.85 mmol), NaH (2.11 g, 8.78 mmol), and DMF ( 80 ml) and then stirred at room temperature for 3 hours. After the reaction was terminated, water was added, the solid compound was filtered and purified by column chromatography to give the compound C-4 (2.42 g, yield: 75%).

GC-Mass (Theoretical value: 522.67 g / mol, Measured value: 522 g / mol)

Synthesis Example 5 Synthesis of Compound C-5

Except for using 2-chloro-4,6-diphenyl-1,3,5-triazine (2.09 g, 7.85 mmol) instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 4, Compound C-5 (2.62 g, yield 81%) was obtained in the same manner as the procedure of 4.

GC-Mass (Theoretical value: 553.65 g / mol, Measured value: 553 g / mol)

Synthesis Example 6 Synthesis of Compound C-6

Compound C was carried out in the same manner as in Synthesis Example 1, except that 4-bromo-N, N-diphenylaniline (8.61 g, 26.57 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1. -6 (4.51 g, yield: 60%) was obtained.

GC-Mass (Theoretical value: 565.70 g / mol, Measured value: 565 g / mol)

Synthesis Example 7 Synthesis of Compound C-7

3-bromo-9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazole (12.65 g, 26.57 mmol instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1 Except for using), the same procedure as in Synthesis Example 1 was carried out to obtain compound C-7 (6.02 g, yield: 63%).

GC-Mass (Theoretical value: 718.85 g / mol, Measured value: 718 g / mol)

Synthesis Example 8 Synthesis of Compound C-8

Synthesis except for using 10- (4-bromophenyl) -9,9-dimethyl-9,10-dihydroacridine (9.64 g, 26.57 mmol) instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1 Compound C-8 (6.12 g, yield: 77%) was obtained in the same manner as in Example 1.

GC-Mass (Theoretical value: 605.77 g / mol, Measured value: 605 g / mol)

Synthesis Example 9 Synthesis of Compound C-9

Except for using (4-bromophenyl) triphenylsilane (11.0 g, 26.57 mmol) instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1, the compound C-9 ( 6.81 g, yield: 78%).

GC-Mass (Theoretical value: 656.89 g / mol, Measured value: 656 g / mol)

Synthesis Example 10 Synthesis of Compound C-10

Except for using 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (10.28 g, 26.57 mmol) instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1 , Compound C-10 (7.03 g, yield: 84%) was obtained in the same manner as in Synthesis example 1.

GC-Mass (Theoretical value: 629.75 g / mol, Measured value: 629 g / mol)

Synthesis Example 11 Synthesis of Compound C-11

2- (4'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1 Except for using (12.30 g, 26.57 mmol), the same procedure as in Synthesis Example 1 was performed to obtain compound C-11 (6.94 g, yield: 74%).

GC-Mass (Theoretical value: 705.85 g / mol, Measured value: 705 g / mol)

Synthesis Example 12 Synthesis of Compound C-12

2- (3'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1 Except for using (12.30 g, 26.57 mmol), the same procedure as in Synthesis Example 1 was performed to obtain compound C-12 (6.47 g, yield: 69%).

GC-Mass (Theoretical value: 705.85 g / mol, Measured value: 705 g / mol)

Synthesis Example 13 Synthesis of Compound C-13

2- (7-bromo-9,9-dimethyl-9H-fluoren-2-yl) -4,6-diphenyl-1,3,5-triazine instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1 Compound C-13 (6.14 g, yield: 62%) was obtained in the same manner as the Synthesis Example 1 except for using (13.36 g, 26.57 mmol).

GC-Mass (Theoretical value: 745.91 g / mol, Measured value: 745 g / mol)

Synthesis Example 14 Synthesis of Compound C-14

N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1,1'-biphenyl] -4 instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1 Except for using -amine (12.30 g, 26.57 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain compound C-14 (8.39 g, yield: 88%).

GC-Mass (Theoretical value: 717.90 g / mol, Measured value: 717 g / mol)

Synthesis Example 15 Synthesis of Compound C-15

N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H-fluoren- instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1 Except that 2-amine (13.68 g, 26.57 mmol) was used, the same procedure as in Synthesis Example 1 was carried out to obtain Compound C-15 (6.55 g, yield: 65%).

GC-Mass (Theoretical value: 757.96 g / mol, Measured value: 757 g / mol)

Synthesis Example 16 Synthesis of Compound C-16

10-([1,1'-biphenyl] -4-yl) -2-bromo-9,9-dimethyl-7-phenyl-9,10- instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1 Except for using dihydroacridine (13.68 g, 26.57 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain compound C-16 (5.74 g, yield: 57%).

GC-Mass (Theoretical value: 757.96 g / mol, Measured value: 757 g / mol)

Synthesis Example 17 Synthesis of Compound C-17

Compound C-17 was prepared by the same procedure as in Synthesis Example 10, except that Compound IC-2 (4.28 g, 13.29 mmol) synthesized in Preparation Example 2 was used instead of Compound IC-1 used in Synthesis Example 10. 5.02 g, yield: 60%).

GC-Mass (Theoretical value: 629.75 g / mol, Measured value: 629 g / mol)

Synthesis Example 18 Synthesis of Compound C-18

Compound C-18 was prepared by the same procedure as in Synthesis Example 11, except that Compound IC-2 (4.28 g, 13.29 mmol) synthesized in Preparation Example 2 was used instead of Compound IC-1 used in Synthesis Example 11. 7.88 g, yield: 84%).

GC-Mass (Theoretical value: 705.85 g / mol, Measured value: 705 g / mol)

Synthesis Example 19 Synthesis of Compound C-19

Compound C-19 was prepared by the same procedure as in Synthesis Example 12, except that Compound IC-2 (4.28 g, 13.29 mmol) synthesized in Preparation Example 2 was used instead of Compound IC-1 used in Synthesis Example 12. 7.69 g, yield: 82%) was obtained.

GC-Mass (Theoretical value: 705.85 g / mol, Measured value: 705 g / mol)

Synthesis Example 20 Synthesis of Compound C-20

A compound C-20 was prepared by the same procedure as in Synthesis Example 10, except that Compound IC-3 (4.28 g, 13.29 mmol) synthesized in Preparation Example 2 was used instead of Compound IC-1 used in Synthesis Example 10. 7.45 g, yield: 89%).

GC-Mass (Theoretical value: 629.75 g / mol, Measured value: 629 g / mol)

Synthesis Example 21 Synthesis of Compound C-21

Compound C-21 was prepared by the same procedure as in Synthesis Example 11, except that Compound IC-3 (4.28 g, 13.29 mmol) synthesized in Preparation Example 2 was used instead of Compound IC-1 used in Synthesis Example 11. 6.56 g, yield: 70%).

GC-Mass (Theoretical value: 705.85 g / mol, Measured value: 705 g / mol)

Synthesis Example 22 Synthesis of Compound C-22

Compound C-22 was prepared by the same procedure as in Synthesis Example 12, except that Compound IC-3 (4.28 g, 13.29 mmol) synthesized in Preparation Example 2 was used instead of Compound IC-1 used in Synthesis Example 12. 7.32 g, yield: 78%).

GC-Mass (Theoretical value: 705.85 g / mol, Measured value: 705 g / mol)

Synthesis Example 23 Synthesis of Compound C-23

Compound C-23 was prepared in the same manner as in Synthesis Example 10, except that Compound IC-4 (4.28 g, 13.29 mmol) synthesized in Preparation Example 3 was used instead of Compound IC-1 used in Synthesis Example 10. 7.28 g, yield: 87%).

GC-Mass (Theoretical value: 629.75 g / mol, Measured value: 629 g / mol)

Synthesis Example 24 Synthesis of Compound C-24

Compound C-24 was carried out in the same manner as in Synthesis Example 11, except that Compound IC-4 (4.28 g, 13.29 mmol) used in Preparation Example 3 was used instead of Compound IC-1 used in Synthesis Example 11. 6.75 g, yield: 72%).

GC-Mass (Theoretical value: 705.85 g / mol, Measured value: 705 g / mol)

Synthesis Example 25 Synthesis of Compound C-25

A compound C-25 was prepared by the same procedure as in Synthesis Example 12, except that Compound IC-4 (4.28 g, 13.29 mmol) used in Preparation Example 3 was used instead of Compound IC-1 used in Synthesis Example 12. 6.19 g, yield: 66%).

GC-Mass (Theoretical value: 705.85 g / mol, Measured value: 705 g / mol)

Synthesis Example 26 Synthesis of Compound C-26

Compound C-26 was prepared by the same procedure as in Synthesis Example 10, except that Compound IC-5 (4.28 g, 13.29 mmol) synthesized in Preparation Example 4 was used instead of Compound IC-1 used in Synthesis Example 10. 5.07 g, yield: 65%).

GC-Mass (Theoretical value: 587.67 g / mol, Measured value: 587 g / mol)

Synthesis Example 27 Synthesis of Compound C-27

Compound C-27 was prepared by the same procedure as in Synthesis Example 11, except that Compound IC-5 (4.28 g, 13.29 mmol) synthesized in Preparation Example 4 was used instead of Compound IC-1 used in Synthesis Example 11. 5.82 g, yield: 66%).

GC-Mass (Theoretical value: 663.77 g / mol, Measured value: 663 g / mol)

Synthesis Example 28 Synthesis of Compound C-28

Compound C-28 was prepared by the same procedure as in Synthesis Example 12, except that Compound IC-5 (4.28 g, 13.29 mmol) synthesized in Preparation Example 4 was used instead of Compound IC-1 used in Synthesis Example 12. 6.35 g, yield: 72%).

GC-Mass (Theoretical value: 663.77 g / mol, Measured value: 663 g / mol)

Synthesis Example 29 Synthesis of Compound C-29

Compound C-29 was prepared by the same procedure as in Synthesis Example 10, except that Compound IC-6 (4.28 g, 13.29 mmol) synthesized in Preparation Example 5 was used instead of Compound IC-1 used in Synthesis Example 10. 4.45 g, yield: 57%).

GC-Mass (Theoretical value: 587.67 g / mol, Measured value: 587 g / mol)

Synthesis Example 30 Synthesis of Compound C-30

Compound C-30 was prepared by the same procedure as in Synthesis Example 11, except that Compound IC-6 (4.28 g, 13.29 mmol) synthesized in Preparation Example 5 was used instead of Compound IC-1 used in Synthesis Example 11. 4.32 g, yield: 49%) was obtained.

GC-Mass (Theoretical value: 663.77 g / mol, Measured value: 663 g / mol)

Synthesis Example 31 Synthesis of Compound C-31

A compound C-31 was prepared in the same manner as in Synthesis Example 12, except that Compound IC-6 (4.28 g, 13.29 mmol) synthesized in Preparation Example 5 was used instead of Compound IC-1 used in Synthesis Example 12. 5.55 g, yield: 63%).

GC-Mass (Theoretical value: 663.77 g / mol, Measured value: 663 g / mol)

Synthesis Example 32 Synthesis of Compound C-32

Compound C-32 was prepared by the same procedure as in Synthesis Example 10, except that Compound IC-7 (4.28 g, 13.29 mmol) synthesized in Preparation Example 5 was used instead of Compound IC-1 used in Synthesis Example 10. 6.01 g, yield: 77%).

GC-Mass (Theoretical value: 587.67 g / mol, Measured value: 587 g / mol)

Synthesis Example 33 Synthesis of Compound C-33

Compound C-33 was prepared by the same procedure as in Synthesis Example 11, except that Compound IC-7 (4.28 g, 13.29 mmol) synthesized in Preparation Example 5 was used instead of Compound IC-1 used in Synthesis Example 11. 7.67 g, yield: 87%).

GC-Mass (Theoretical value: 663.77 g / mol, Measured value: 663 g / mol)

Synthesis Example 34 Synthesis of Compound C-34

A compound C-34 was prepared in the same manner as in Synthesis Example 12, except that Compound IC-7 (4.28 g, 13.29 mmol) synthesized in Preparation Example 5 was used instead of Compound IC-1 used in Synthesis Example 12. 6.53 g, yield: 74%).

GC-Mass (Theoretical value: 663.77 g / mol, Measured value: 663 g / mol)

Synthesis Example 35 Synthesis of Compound C-35

Compound C-35 was prepared in the same manner as in Synthesis Example 10, except that Compound IC-8 (4.28 g, 13.29 mmol) synthesized in Preparation Example 6 was used instead of Compound IC-1 used in Synthesis Example 10. 6.71 g, yield: 86%).

GC-Mass (Theoretical value: 587.67 g / mol, Measured value: 587 g / mol)

Synthesis Example 36 Synthesis of Compound C-36

Compound C-36 was prepared by the same procedure as in Synthesis Example 11, except that Compound IC-8 (4.28 g, 13.29 mmol) synthesized in Preparation Example 6 was used instead of Compound IC-1 used in Synthesis Example 11. 5.64 g, yield: 64%).

GC-Mass (Theoretical value: 663.77 g / mol, Measured value: 663 g / mol)

Synthesis Example 37 Synthesis of Compound C-37

Compound C-37 was prepared by the same procedure as in Synthesis Example 12, except that Compound IC-8 (4.28 g, 13.29 mmol) synthesized in Preparation Example 6 was used instead of Compound IC-1 used in Synthesis Example 12. 6.88 g, yield: 78%).

GC-Mass (Theoretical value: 663.77 g / mol, Measured value: 663 g / mol)

Synthesis Example 38 Synthesis of Compound C-38

Compound C-38 was prepared by the same procedure as in Synthesis Example 10, except that Compound IC-9 (4.28 g, 13.29 mmol) synthesized in Preparation Example 7 was used instead of Compound IC-1 used in Synthesis Example 10. 6.44 g, yield: 77%).

GC-Mass (Theoretical value: 629.75 g / mol, Measured value: 629 g / mol)

Synthesis Example 39 Synthesis of Compound C-39

Compound C-39 was prepared by the same procedure as in Synthesis Example 11, except that Compound IC-9 (4.28 g, 13.29 mmol) synthesized in Preparation Example 7 was used instead of Compound IC-1 used in Synthesis Example 11. 5.63 g, yield: 60%).

GC-Mass (Theoretical value: 705.85 g / mol, Measured value: 705 g / mol)

Synthesis Example 40 Synthesis of Compound C-40

A compound C-40 was prepared by the same procedure as in Synthesis Example 12, except that Compound IC-9 (4.28 g, 13.29 mmol) synthesized in Preparation Example 7 was used instead of Compound IC-1 used in Synthesis Example 12. 4.97 g, yield: 53%) was obtained.

GC-Mass (Theoretical value: 705.85 g / mol, Measured value: 705 g / mol)

Synthesis Example 41 Synthesis of Compound C-41

A compound C-41 was prepared in the same manner as in Synthesis Example 10, except that Compound IC-10 (4.28 g, 13.29 mmol) synthesized in Preparation Example 7 was used instead of Compound IC-1 used in Synthesis Example 10. 6.27 g, yield: 75%).

GC-Mass (Theoretical value: 629.75 g / mol, Measured value: 629 g / mol)

Synthesis Example 42 Synthesis of Compound C-42

Compound C-42 was prepared by the same procedure as in Synthesis Example 11, except that Compound IC-10 (4.28 g, 13.29 mmol) synthesized in Preparation Example 7 was used instead of Compound IC-1 used in Synthesis Example 11. 6.75 g, yield: 72%).

GC-Mass (Theoretical value: 705.85 g / mol, Measured value: 705 g / mol)

Synthesis Example 43 Synthesis of Compound C-43

Compound C-43 was prepared by the same procedure as in Synthesis Example 12, except that Compound IC-10 (4.28 g, 13.29 mmol) synthesized in Preparation Example 7 was used instead of Compound IC-1 used in Synthesis Example 12. 5.90 g, yield: 63%).

GC-Mass (Theoretical value: 705.85 g / mol, Measured value: 705 g / mol)

Synthesis Example 44 Synthesis of Compound C-44

Compound IC-11 (3.49 g, 7.31 mmol), 2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan, synthesized in Preparation Example 8 under nitrogen stream -2-yl) phenyl) -1,3,5-triazine (3.81 g, 8.77 mmol), NaOH (0.87 g, 21.93 mmol), Pd (PPh ₃ ) ₄ (0.25 g, 0.21 mmol) and 1,4- dioxane, H 2 O (30 ml, 8 ml) was mixed and then stirred at 100 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with ethyl acetate, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer to give a compound C-44 (2.37 g, yield: 46%) by column chromatography.

GC-Mass (Theoretical value: 705.85 g / mol, Measured value: 705 g / mol)

Synthesis Example 45 Synthesis of Compound C-45

2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine used in Synthesis Example 44 N-([1,1'-biphenyl] -4-yl) -N- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)-[ Compound C-45 (2.26 g, yield: 39%) was obtained in the same manner as Synthesis Example 44 except for using 1,1'-biphenyl] -4-amine (4.58 g, 8.77 mmol). .

GC-Mass (Theoretical value: 793.99 g / mol, Measured value: 793 g / mol)

Synthesis Example 46 Synthesis of Compound C-46

2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine used in Synthesis Example 44 Instead N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-N- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- Except for using yl) phenyl) -9H-fluoren-2-amine (4.94 g, 8.77 mmol), the compound C-46 (2.19 g, yield: 36%) was obtained by the same procedure as in Synthesis Example 44. Got it.

GC-Mass (Theoretical value: 834.06 g / mol, Measured value: 833 g / mol)

Synthesis Example 47 Synthesis of Compound C-47

2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine used in Synthesis Example 44 Instead of 10-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-2-phenyl-7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2 Compound C-47 (3.17 g, yield: 52%) was obtained in the same manner as Synthesis Example 44 except for using -yl) -9,10-dihydroacridine (4.94 g, 8.77 mmol).

GC-Mass (Theoretical value: 834.06 g / mol, Measured value: 833 g / mol)

Synthesis Example 48 Synthesis of Compound C-48

Compound C-48 was prepared by the same procedure as in Synthesis Example 44, except that Compound IC-12 (3.49 g, 7.31 mmol) synthesized in Preparation Example 8 was used instead of Compound IC-11 used in Synthesis Example 44. 2.83 g, yield: 55%).

GC-Mass (Theoretical value: 705.85 g / mol, Measured value: 705 g / mol)

Synthesis Example 49 Synthesis of Compound C-49

A compound C-49 was prepared in the same manner as in Synthesis Example 45, except that Compound IC-12 (3.49 g, 7.31 mmol) synthesized in Preparation Example 8 was used instead of Compound IC-11 used in Synthesis Example 45. 2.38 g, yield: 41%).

GC-Mass (Theoretical value: 793.99 g / mol, Measured value: 793 g / mol)

Synthesis Example 50 Synthesis of Compound C-50

A compound C-50 was prepared in the same manner as in Synthesis Example 46, except that Compound IC-12 (3.49 g, 7.31 mmol) synthesized in Preparation Example 8 was used instead of Compound IC-11 used in Synthesis Example 46. 2.44 g, yield: 40%).

GC-Mass (Theoretical value: 834.06 g / mol, Measured value: 833 g / mol)

Synthesis Example 51 Synthesis of Compound C-51

Compound C-51 was prepared by the same procedure as in Synthesis Example 47, except that Compound IC-12 (3.49 g, 7.31 mmol) synthesized in Preparation Example 8 was used instead of Compound IC-11 used in Synthesis Example 47. 2.01 g, yield: 33%).

GC-Mass (Theoretical value: 834.06 g / mol, Measured value: 833 g / mol)

Example 1 Manufacture of Green Organic EL Device

After compound C-1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, a green organic EL device was manufactured as follows.

A glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.

On the prepared ITO transparent electrode, using Compound C-1 of Synthesis Example 1 as a host material, m-MTDATA (60 nm) / TCTA (80 nm) / Compound C-1 + 10% Ir (ppy) ₃ An organic EL device was fabricated by stacking (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in this order.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , CBP and BCP used are as follows.

[Examples 2 to 51]-Fabrication of Organic EL Device

Except for using the compounds C-2 to C-51 synthesized in Synthesis Examples 2 to 51 instead of the compound C-1 used as a host material in the formation of the emission layer in Example 1, the same as in Example 1 To an organic EL device.

Comparative Example 1 Fabrication of Green Organic EL Device

A green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound C-1 used as a host material in forming the emission layer in Example 1. The structure of CBP used is as follows.

Experimental Example

For green organic EL devices prepared in Examples 1 to 51 and Comparative Example 1, driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below. .

Table 1

Sample	Host	Driving voltage (V)	Current efficiency (cd / A)
Example 1	Compound C-1	6.50	41.0
Example 2	Compound C-2	6.45	41.2
Example 3	Compound c-3	6.55	41.1
Example 4	Compound c-4	6.50	40.9
Example 5	Compound C-5	6.60	41.3
Example 6	Compound c-6	6.55	41.0
Example 7	Compound c-7	6.50	41.4
Example 8	Compound c-8	6.46	41.9
Example 9	Compound c-9	6.55	41.5
Example 10	Compound C-10	6.45	41.3
Example 11	Compound C-11	6.60	41.8
Example 12	Compound c-12	6.55	42.1
Example 13	Compound C-13	6.60	41.2
Example 14	Compound c-14	6.54	41.7
Example 15	Compound c-15	6.65	42.1
Example 16	Compound c-16	6.60	41.5
Example 17	Compound c-17	6.59	41.8
Example 18	Compound c-18	6.50	41.7
Example 19	Compound c-19	6.45	41.8
Example 20	Compound C-20	6.51	41.3
Example 21	Compound c-21	6.55	40.9
Example 22	Compound c-22	6.60	41.2
Example 23	Compound c-23	6.49	41.5
Example 24	Compound c-24	6.52	40.8
Example 25	Compound C-25	6.55	40.9
Example 26	Compound C-26	6.59	41.7
Example 27	Compound c-27	6.60	42.3
Example 28	Compound c-28	6.50	41.6
Example 29	Compound c-29	6.55	41.4
Example 30	Compound C-30	6.50	41.7
Example 31	Compound c-31	6.60	40.8
Example 32	Compound c-32	6.58	41.0
Example 33	Compound c-33	6.55	41.2
Example 34	Compound c-34	6.51	41.5
Example 35	Compound C-35	6.65	42.1
Example 36	Compound c-36	6.60	41.5
Example 37	Compound c-37	6.62	40.9
Example 38	Compound c-38	6.55	41.7
Example 39	Compound C-39	6.60	40.6
Example 40	Compound c-40	6.52	41.3
Example 41	Compound c-41	6.50	40.5
Example 42	Compound c-42	6.55	41.5
Example 43	Compound c-43	6.45	41.7
Example 44	Compound c-44	6.52	40.8
Example 45	Compound c-45	6.55	41.0
Example 46	Compound c-46	6.58	41.3
Example 47	Compound c-47	6.60	41.1
Example 48	Compound c-48	6.53	40.9
Example 49	Compound c-49	6.55	41.0
Example 50	Compound C-50	6.50	41.5
Example 51	Compound c-51	6.45	40.8
Comparative Example 1	CBP	6.93	38.2

As a result of the experiment, the green organic EL devices of Examples 1 to 51 using the compounds represented by the formula (1) according to the present invention (Compounds C-1 to C-51) as the host material of the light emitting layer were comparative examples using conventional CBP. It was confirmed that the green organic EL device of 1 exhibited better performance in terms of current efficiency and driving voltage.

Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications and changes can be made within the scope of the claims and the detailed description of the invention, which also fall within the scope of the invention. It is natural.

Claims (8)

1. Compound represented by the following formula (1):

   [Formula 1]

   

   (In Formula 1,

   R ₁ to R ₅ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C ₁ -C ₄₀ alkyl group, a substituted or unsubstituted C ₂ -C ₄₀ alkenyl group , Substituted or unsubstituted C ₂ -C ₄₀ alkynyl group, substituted or unsubstituted C ₆ -C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ Alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, substituted or unsubstituted C ₃ ~ C ₄₀ A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, Substituted or unsubstituted C _{6 Through} C ₄₀ Aryl boron group, Substituted or unsubstituted C _{6 Through} C ₄₀ Aryl phosphine group, Substituted or unsubstituted C _{6 Through} C ₄₀ Is selected from the group consisting of an aryl phosphine oxide group and a substituted or unsubstituted C ₆ ~ C ₄₀ arylsilyl group, or may be combined with adjacent groups to form a condensed ring,

   However, R ₁ and R ₂ may be condensed together to form a condensed ring represented by one of Formulas 2 to 4, or one of R ₃ to R ₅ may be condensed with an adjacent group to form a condensed ring represented by Formula 5 below. Form;

   [Formula 2]

   

   [Formula 3]

   

   [Formula 4]

   

   [Formula 5]

   

   R ₆ to R ₁₁ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group , Substituted or unsubstituted C ₂ -C ₄₀ alkynyl group, substituted or unsubstituted C ₆ -C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ ~ C ₄₀ aryloxy group, substituted or unsubstituted C ₁ ~ C ₄₀ Alkyloxy group, substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group, substituted or unsubstituted C ₃ ~ C ₄₀ A cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, Substituted or unsubstituted C _{6 Through} C ₄₀ Aryl boron group, Substituted or unsubstituted C _{6 Through} C ₄₀ Aryl phosphine group, Substituted or unsubstituted C _{6 Through} C ₄₀ An arylphosphine oxide group and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group, or may be combined with an adjacent group to form a condensed ring;

   Ar ₁ is a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, substituted or unsubstituted C ₁ to C ₄₀ Alkyloxy group, substituted or unsubstituted C ₆ to C ₄₀ arylamine group, substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, substituted Or an unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ to C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ to C ₄₀ arylphosphine group, substituted or unsubstituted C ₆ to C ₄₀ arylphosphine oxide group and substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group Selected from the group;

   n is an integer from 0 to 4, and if n is an integer from 1 to 4, at least one Ra is each independently deuterium, halogen, cyano, substituted or unsubstituted C ₁ -C ₄₀ alkyl group, substituted or unsubstituted C Alkenyl group of ₂ to C ₄₀ , substituted or unsubstituted alkynyl group of C ₂ to C ₄₀ , substituted or unsubstituted C ₆ to C ₄₀ aryl group, substituted or unsubstituted heteroaryl of 5 to 40 nuclear atoms Groups, substituted or unsubstituted C ₆ -C ₄₀ aryloxy group, substituted or unsubstituted C ₁ -C ₄₀ alkyloxy group, substituted or unsubstituted C ₆ -C ₄₀ arylamine group, substituted or unsubstituted A substituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl boron group, and an aryl phosphonium substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ of pingi, substituted Combines groups selected from the group consisting of aryl silyl unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted C ₆ ~ C ₄₀ is, or adjacent to form a condensed ring;

   X is a single bond or is selected from the group consisting of C (R ₂₁ ) (R ₂₂ ), N (R ₂₃ ), O and S;

   R ₂₁ to R ₂₃ are each independently hydrogen, deuterium, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, or a substituted or unsubstituted nuclear atom 5 to 5 40 heteroaryl group and substituted or unsubstituted C ₆ ~ C ₄₀ arylamine group;

   The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, arylalkyl group, cycloalkyl group, heterocycloalkyl group, alkyl of R ₁ to R _11, Ra and Ar ₁ One or more substituents introduced into the silyl group, the alkyl boron group, the aryl boron group, the arylphosphine group, the arylphosphine oxide group and the arylsilyl group, and the alkyl group, the aryl group, the heteroaryl group and the arylamine group of R ₂₁ to R ₂₃ , respectively Deuterium, halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, 5 to 5 nuclear atoms each independently 40 heteroaryl groups, C ₆ to C ₄₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₄₀ arylamine groups, C ₃ to C ₄₀ cycloalkyl groups, nuclear atoms 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ alkyl group of boron, C ₆ ~ C ₄₀ aryl group of boron, C ₆ ~ C ₄₀ aryl group Spin group, C ₆ ~ C ₄₀ aryl phosphine oxide is selected from the pin group and an aryl silyl group the group consisting of a C ₆ ~ C ₄₀ of, wherein if the plurality of substituents, may be the same or different from each other).
2. The compound of claim 1, wherein X is a single bond or C (R ₂₁ ) (R ₂₂ ).
3. The method of claim 1, wherein Ar ₁ is selected from the group consisting of a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms,

   In this case one or more substituents to be introduced, each aryl group, and heteroaryl of Ar ₁ are each independently a heavy hydrogen, a halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the Alkynyl group, C ₆ ~ C ₄₀ aryl group, C ₅ ~ C ₄₀ heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₄₀ aryl An amine group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ aryl is selected from boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group the group consisting of, but if the substituent multiple individual, equal to each other Or are characterized by being different.
4. The compound of claim 1, wherein Ar ₁ is selected from the group consisting of the following substituents A1 to A64:

   

   

   

   

   

   
5. The compound of claim 1 selected from the group consisting of compounds represented by the following Chemical Formulas 6 to 15:

   [Formula 6]

   

   [Formula 7]

   

   [Formula 8]

   

   [Formula 9]

   

   [Formula 10]

   

   [Formula 11]

   

   [Formula 12]

   

   [Formula 13]

   

   [Formula 14]

   

   [Formula 15]

   

   (In Chemical Formula 6 to Formula 15,

   R ₁ to R ₁₁ , Ra, Ar _1, X and n are each as defined in claim 1)
6. The compound of claim 1 selected from the group consisting of compounds represented by the following formulas INV-1 to INV-20:

   

   

   

   

   

   

   

   (In the above formulas INV-1 to INV-20,

   R ₁ to R ₁₁ , Ra, Ar ₁ and n are each as defined in claim 1).
7. In an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode,

   At least one of the one or more organic material layers comprises the compound according to any one of claims 1 to 6.
8. The organic electroluminescent device according to claim 7, wherein the organic material layer including the compound is a light emitting layer.