KR20140064612A - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a compound represented as the chemical formula 1 and an organic electroluminescent device comprising the same. Light emitting efficiency, a driving voltage, and a service life of a device can be improved by comprising the compound, represented by the chemical formula 1, in at least one organic layer and preferably in a light emitting layer. (For the chemical formula 1, R1 to R5, Ra, X and n are as defined in the detailed description.).

Description

TECHNICAL FIELD [0001] The present invention relates to an organic compound and an organic electroluminescent device including the organic compound.

The present invention relates to an organic compound which can be used as a material for an organic electroluminescence device and an organic electroluminescence device comprising the same. More specifically, the present invention relates to an organic compound which has excellent thermal stability and light- To an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and life span.

A study on organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices') led to blue electroluminescence using anthracene single crystals in 1965, starting from the observation of organic thin film emission of Bernanose in the 1950s In 1987, a layered organic EL device was proposed by Tang divided into a hole layer and a functional layer of a light emitting layer. Thereafter, in order to make a high efficiency and high number of organic EL devices, each organic EL device has been developed in a manner of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therefor.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic layer in the anode, and electrons are injected into the organic layer in the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material and the like depending on its function.

The luminescent material can be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials necessary for realizing better natural colors. Further, in order to increase the color purity and to increase the luminous efficiency through energy transfer, a host / dopant system can be used as a luminescent material.

The dopant material can 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 phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescent material, researches on phosphorescent host materials as well as phosphorescent dopants have been conducted.

Up to now, hole injecting layer, hole transporting layer. NPB, BCP, and Alq ₃ are widely known as the hole blocking layer and the electron transporting layer, and anthracene derivatives as a luminescent material have been reported as fluorescent dopant / host material. In particular, the phosphor has a great advantage in improving the efficiency aspects of the light-emitting material materials _{Firpic, Ir (ppy) 3,} (acac) Ir (btp) 2 Ir metal complex compound is blue (blue), which includes the same as the green ( green and red dopant materials, and CBP is a phosphorescent host material.

However, conventional luminescent materials are good in terms of luminescence characteristics, but have low thermal stability due to their low glass transition temperature, and thus are not satisfactory in terms of lifetime in organic EL devices. Therefore, development of a luminescent material having excellent performance is required.

Japanese Patent Application Laid-Open No. 2001-160489

An object of the present invention is to provide a novel organic compound capable of improving the bonding force between holes and electrons while having excellent thermal stability due to a high glass transition temperature.

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

The present invention provides a compound represented by the following formula (1): < EMI ID =

In Formula 1,

R ₁ to R ₅ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl, substituted or unsubstituted C ₂ to C ₄₀ alkenyl , A substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, a substituted or unsubstituted A C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₃ to C ₄₀ A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₁ to C ₄₀ alkylcarbonyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nucleus atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ ring An aryl phosphine oxide group and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group, or may be bonded to an adjacent group to form a condensed ring,

R ₁ and R ₂ are condensed with each other to form a condensed ring represented by one of the following formulas (2) to (4), or one of R ₃ to R ₅ is condensed with an adjacent condensed ring to form a condensed ring represented by the following formula Lt; / RTI &

R ₆ to R ₁₁ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted C ₂ to C ₄₀ alkenyl group , A substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, a substituted or unsubstituted A C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₃ to C ₄₀ A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₁ to C ₄₀ alkylcarbonyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nucleus atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ ring An aryl phosphine oxide group and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group, or may be bonded to an adjacent group to form a condensed ring,

Ar ₁ represents a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, a substituted or unsubstituted C _A substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, a substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ A substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a 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 arylboron group, a substituted or unsubstituted 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 aryl silyl group consisting of ≪ / RTI >

n is an integer of 0 to 4, provided that when n is an integer of 1 to 4, at least one Ra is independently selected from the group consisting of deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ of the alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted number of 5 to 40 heteroaryl unsubstituted nucleus atoms aryl A substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, hwandoen C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted 3 to 40 nuclear atoms of a heterocycloalkyl group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl silyl group, a substituted or non-substituted of unsubstituted C ₁ ~ 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 each independently represent hydrogen, deuterium, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted five to twenty- 40 heteroaryl groups and substituted or unsubstituted C ₆ -C ₄₀ arylamine groups;

Wherein R ₁ to R _11, the alkyl group of Ra and Ar _1, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an aryl group, a cycloalkyl group, a heterocycloalkyl group, an alkyl An aryl group, an aryl group, an aryl group, a silyl group, an alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group and an arylsilyl group, and R ₂₁ to R ₂₃ each independently represent an alkyl group, an aryl group, a heteroaryl group, Each independently represent a group selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₆ to C ₄₀ aryl, to 40 heteroaryl group, C ₆ ~ aryloxy C ₄₀ of, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a 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 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.

Further, the present invention is an organic electroluminescent device comprising a cathode, a cathode, and one or more organic layers sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes the compound An organic electroluminescent device is provided.

The compound represented by the general formula (1) of the present invention is excellent in thermal stability and phosphorescence properties and can be applied to a light emitting layer of an organic electroluminescent device.

Accordingly, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host material, it is possible to manufacture an organic electroluminescent device having excellent light emitting performance, low driving voltage, high efficiency and long life time as compared with the conventional host material, , And a full color display panel having a greatly improved lifetime can be manufactured.

Hereinafter, the present invention will be described in detail.

The novel compound according to the present invention has a structure in which an indole moiety is fused at the terminal of a pyrroloacridine moiety to form a basic skeleton and various substituents are bonded to the basic skeleton. (1). The compound represented by the formula (1) has a larger molecular weight than the conventional organic EL device materials (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as "CBP")] The bonding force of electrons can be increased. Accordingly, when the compound of Formula 1 is used in an organic EL device, the driving voltage, efficiency (luminous efficiency, power efficiency), lifetime and brightness of the device can be improved.

The compound represented by Formula 1 has a structure in which a large indole moiety is bonded to an electron donor at the terminal of a pyrroloacridine moiety and can have a wide band gap. In addition, the above compound has various bipolar properties due to various aromatic ring substituents having an electron-withdrawing group (EWG) bonded to a basic skeleton and having a high electron absorbing property, . Therefore, when the above compound is applied to the organic EL device, the phosphorescent property of the device can be improved and the hole injecting ability and / or transporting ability, luminous efficiency, The driving voltage, the life characteristic, and the like can be improved. Further, the energy level can be controlled according to the substituent, so that it has a wide band gap (sky blue to red), and thus can be applied not only to a light emitting layer but also to a hole transporting layer and a hole injecting layer.

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

In addition, due to various aromatic ring substituents introduced in many indole moieties, the molecular weight of the compound is significantly increased, so that the glass transition temperature can be improved, and therefore, it has higher thermal stability than conventional CBP . In addition, the indole moiety bonded to the end of the pyrroloacridine moiety may be fused to improve the thermal stability of the compound. In addition, It is also effective in inhibiting the crystallization of the organic layer. Therefore, the device including the compound of Formula 1 according to the present invention can greatly improve durability and lifetime characteristics.

In addition, when the compound of Formula 1 according to the present invention is used as a positive hole injection / transport layer material, a blue, green and / or red phosphorescent host material of an organic EL device, it exerts an excellent effect in terms of efficiency and life . Therefore, the compound according to the present invention can greatly contribute to the improvement of the performance and lifetime of the organic EL device, and particularly the lifetime improvement of the device has a great effect for 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 or different and each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl group Or an unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted nucleus atom number of 5 A substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine A substituted or unsubstituted 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, hwandoen C ₁ ~ C ₄₀ alkyl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ Aryl phosphine of C ₄₀ pingi, substituted or non-substituted is selected from unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and the group consisting of aryl silyl substituted or unsubstituted C ₆ ~ C _40, or adjacent groups combine to A condensed ring can be formed.

In this case, the R ₁ to R ₅ group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an aryl group, a cycloalkyl group, a heterocycloalkyl group, alkyl silyl group, A halogen atom, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, _A C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ An alkyloxycarbonyl group, an alkyloxyl group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to 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, among R ₁ to R ₅ , R ₁ and R ₂ are fused with each other to form a fused ring represented by one of the formulas (2) to (4), or one of R ₃ to R ₅ is adjacent To form a condensed ring represented by the general formula (5). For example, in the case of R ₁ to R ₅ , when R ₃ is condensed with an adjacent group R ₄ to form a condensed ring represented by the formula (5), a compound represented by the following formula (6) or (8) is formed. Alternatively, when R ₁ and R ₂ in the above-mentioned R ₁ to R ₅ are condensed to form a condensed ring represented by one of the above formulas 2 to 4, a compound represented by one of the following formulas 10 to 15 is formed.

In the above formulas 2 to 5, the dotted line indicates a site where condensation is performed with the compound of formula (1).

R ₆ to R ₁₁ are the same or different from each other and each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted C ₂ to C ₄₀ alkene 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 can be a heteroaryl group of from 5 to 40, a substituted or unsubstituted nucleus of atoms of a C ₆ ~ C ₄₀ of the aryloxy group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, the substituted or unsubstituted C ₆ ~ C ₄₀ aryl amine group, a substituted or unsubstituted C ₃ ~ C _A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, , A substituted or unsubstituted C ₆ to C ₄₀ arylboron group, a substituted or unsubstituted C ₆ to C ₄₀ arylphosphine group, a substituted or unsubstituted C ₆ to select from the aryl phosphine oxide group, and the group consisting of aryl silyl substituted or unsubstituted C ₆ to C ₄₀ of the C ₄₀ is a bond, or adjacent groups which may form a condensed ring.

In this case, the R ₆ to R ₁₁ an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an aryl group, a cycloalkyl group, a heterocycloalkyl group, alkyl silyl group, A halogen atom, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, _A C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ An alkyloxycarbonyl group, an alkyloxyl group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to 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.

Wherein Ar ₁ is a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, a substituted or unsubstituted A C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, a substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ A substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nucleus 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 to C ₄₀ arylboron groups, 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 , an aryl boron group, an aryl phosphine group, aryl phosphine oxide groups and arylsilyl groups or a salt thereof introduced respectively are each independently a heavy hydrogen, a halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ alkenyl of C ₄₀ A C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group , A C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron 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.

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 with substituent Ra. Further, if the n is an integer from 1 to 4, as the hydrogen is substituted with a substituent Ra, one or more Ra are each independently selected from deuterium, halogen, cyano, substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or An unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, A substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group , A substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nucleus atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a C ₁ ~ C ₄₀ of the alkyl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ Ah A substituted or unsubstituted C ₆ to C ₄₀ arylphosphine oxide group, and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group, or may be bonded to an adjacent group to form a condensed ring .

In the above Ra, 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, aryl boron group, an aryl phosphine group, aryl phosphine oxide groups and arylsilyl groups or a salt thereof introduced respectively are each independently a heavy hydrogen, a halogen, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group , A C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ aryl amine group, a C ₃ ~ C ₄₀ cycloalkyl group, the nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ alkyl boronic 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.

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

Each of R ₂₁ to R ₂₃ is 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, a substituted or unsubstituted 5 to 5 nuclear atoms To about 40 heteroaryl groups, and substituted or unsubstituted C ₆ to C ₄₀ arylamine groups. According to an embodiment of the present invention, when X is C (R ₂₁ ) (R ₂₂ ), R ₂₁ and R ₂₂ are each a hydrogen, a substituted or unsubstituted C ₁ -C ₄₀ alkyl group, or a substituted or unsubstituted It is preferably an aryl group of C ₆ to C ₄₀ , more preferably a methyl group or a phenyl group.

In this case, one or more substituents respectively introduced into the alkyl group, aryl group, heteroaryl group and arylamine group of R ₂₁ to R ₂₃ are each independently selected from the group consisting of deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C _A C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ An alkyloxycarbonyl group, an alkyloxyl group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to 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.

In the compound of formula (I) according to the present invention, preferably, R ₁ to R _11, Ra and Ar ₁ are each independently selected from the group consisting of hydrogen, or substituents S1 to S206, but are not limited thereto.

In the compound of Formula 1, it is preferable that Ar ₁ is selected from the group consisting of Substituents A 1 to A 64 shown below.

Examples of the compound represented by the formula (1) according to the present invention include, but are not limited to, the compounds represented by the following formulas (6) to (15).

In the above Chemical Formulas 6 to 15,

R ₁ to R ₁₁ , Ra, Ar _1, X and n are as defined in formula (1), respectively.

Specific examples of the compound represented by the formula (1) include compounds represented by the following formulas INV-1 to INV-20, but are not limited thereto:

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

R ₁ to R ₁₁ , Ra, Ar ₁ and n are each as defined in formula (1).

Representative examples of the compound represented by the formula (1) include, but are not limited to, the following compounds.

"Unsubstituted alkyl" used in the present invention is a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso -Amyl, hexyl, and the like.

The term "unsubstituted alkenyl" in the present invention is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include vinyl but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

In the present invention, "unsubstituted alkynyl" is a monovalent substituent group derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond, But are not limited to, ethynyl, 2-propynyl, and the like.

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 to each other in a pendant or fused form to each other. Examples of aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

In the present invention, "unsubstituted heteroaryl" means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. One or more carbons, preferably one to three carbons, of the ring are substituted with a heteroatom such as N, O, S or Se. It is interpreted that two or more rings may be attached to each other in a pendant 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, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. Includes rings and is also meant 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-, and 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" means a monovalent substituent group represented by R'O-, wherein R 'represents 1 to 40 alkyl, and may be linear, branched or cyclic (cyclic) structure. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

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 includes at least one carbon atom, preferably 1 to 3 carbons 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, the term "fused ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

The compounds of formula 1 of the present invention can be synthesized according to the general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995 ). Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

Meanwhile, the present invention provides an organic electroluminescent device comprising the compound represented by the above-mentioned formula (1), preferably the compound represented by the formula (6) to the compound represented by the formula (15).

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes The compound represented by the above formula (1), preferably the compound represented by the formula (6) to the compound represented by the formula (15). At this time, the compound of Formula 1 may be used singly or in combination of two or more.

The one or more organic layers may be at least one of a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer, and at least one organic layer may include a compound represented by Formula 1. Preferably, the organic compound layer containing the compound of Compound 1 may be an emissive layer.

According to an embodiment of the present invention, the light emitting layer of the organic electroluminescent device may include a host material, and the host material may include the compound of the above formula (1). Thus, when the compound of Formula 1 is incorporated into a light emitting layer material of an organic electroluminescent device, preferably a blue, green, or red phosphorescent host, the bonding strength between holes and electrons in the light emitting layer is increased. (Luminous efficiency and power efficiency), lifetime, luminance, driving voltage, and the like can be improved.

The structure of the organic electroluminescent device according to the present invention is not particularly limited and may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially stacked. At least one of the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include a compound represented by Formula 1, and preferably, the emitting layer includes a compound represented by Formula 1 . In particular, when the light emitting layer comprises 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 layers and an anode are sequentially laminated, and an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic layer.

The organic electroluminescent device according to the present invention may be formed by using materials and methods known in the art, except that at least one layer (for example, a light emitting layer) of the organic material layer includes the compound represented by Formula 1 Other organic material layers and electrodes.

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 a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet can be used.

Examples of the positive electrode 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), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as 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 multi-layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are illustrative of the present invention, and 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) and K ₂ CO ₃ (34.2 g, 0.248 mmol) ), 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 terminated, the nitrobenzene was removed, the organic layer was separated with methylene chloride, and then the water was removed using MgSO ₄ . Then, the solvent of the organic layer was removed, and the residue was 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

Methyl-2- (4-bromo-1H-indol-1-yl) benzoate (23.1 g, 70.0 mmol) obtained in Step 1 of Preparation Example 1 was dissolved in 250 ml of ether under a nitrogen stream, Methyl lithium (1.6 M in ether, 110 ml, 0.175 mol) was added thereto, followed by stirring for 1 hour and further stirring at room temperature for 4 hours. After the reaction was completed, 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) and stirred at room temperature for 6 hours. Then, an organic layer was separated using methylene chloride and water, water was removed from the organic layer using MgSO ₄ , and recrystallization with ethanol 3-bromo-6,6-dimethyl-6H-pyrrolo [3,2,1-de] acridine (13.5 g, 43.4 mmol, yield 62%).

^{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

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 and 2-nitrophenylboronic acid g, 9.67 mmol), NaOH (1.06 g, 26.37 mmol) and THF / H ₂ O (100 ml / 50 ml) were mixed and stirred. Then, at 40 ℃ into the _{Pd (PPh 3) 4 (0.51} g, 5 mol%) to the mixture, and the mixture was stirred at 80 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride and then filtered with MgSO ₄ . 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 : 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

(2-nitrophenyl) -6H-pyrrolo [3,2,1-de] acridine (2.56 g, 7.22 mmol) obtained in Step 3 of Preparation Example 1 and 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 the 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

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

Methyl-2- (5-bromo-1H-indol-1-yl) benzoate (23.1 g, prepared as described in Example 1) was used instead of methyl 2- 4-bromo-6,6-dimethyl-6H-pyrrolo [3,2,1-de] acridine was obtained by following the procedure of <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

Bromo-6,6-dimethyl-6H-pyrrolo [3,3-dimethyl-6H-pyrrolo [3,2,1-de] acridine used in Step 3 of Preparation Example 1 was used instead of 3-bromo- Dimethyl-4- (2-nitrophenyl) -2,3-dimethyl-quinolinecarboxylic acid dihydrochloride was prepared in the same manner as Step 3 of Preparation Example 1, except that 2,1-deacridine (2.75 g, -6H-pyrrolo [3,2,1-de] acridine.

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

<Step 4> Synthesis of compound IC-2 and compound IC-3

6,6-dimethyl-4- (2-nitrophenyl) -6H-pyrrolo [3,2,1-de] acridine used in Step 4 of Preparation Example 1 was used instead of 6,6- The same procedure as in <Step 4> of Preparation Example 1 was carried out except that nitrophenyl-6H-pyrrolo [3,2,1-de] acridine (5.12 g, 14.44 mmol) Compound IC-3 was obtained.

Compound ¹ H-NMR of the 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)

The compounds of the ^{IC-3 1 H-NMR:} 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, 1 H)

[Preparation Example 3] Synthesis of Compound IC-4

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

Except that 6-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- (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, yield) was used in the place of methyl 2- 5-bromo-6,6-dimethyl-6H-pyrrolo [3,2,1-de] acridine was obtained by following the procedure of <Step 2> of Preparation Example 1, .

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

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

Bromo-6,6-dimethyl-6H-pyrrolo [3,3-dimethyl-6H-pyrrolo [3,2,1-de] acridine used in Step 3 of Preparation Example 1 was used instead of 3-bromo- Dimethyl-5- (2-nitrophenyl) benzoic acid was prepared by following the procedure of <Step 3> of Preparation Example 1, except that 2,1-deacridine (2.75 g, 8.80 mmol) -6H-pyrrolo [3,2,1-de] acridine.

^{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-nitrophenyl) -6H-pyrrolo [3,2,1-de] acridine used in Step 4 of Preparation Example 1 was used instead of 6,6- 4 was prepared in the same manner as in <Step 4> of Preparation Example 1 except that the compound IC-4 was used instead of the compound IC-4, except that the compound IC-4 was replaced with nitrophenyl-6H-pyrrolo [ .

^{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

(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 / 500 ml) were mixed and then stirred. Then, at 40 ℃ into the _{Pd (PPh 3) 4 (5.1} g, 5 mol%) to the mixture in the following, 80 ℃ was stirred for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride and then filtered with MgSO ₄ . 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) was treated with Cu powder (0.45 g, 7.44 mmol), K ₂ CO ₃ g, 0.074 mmol), Na ₂ SO ₄ (10.6 g, 0.074 mmol) and nitrobenzene (300 ml), followed by stirring at 190 ° C for 12 hours. After the reaction was completed, the nitrobenzene was removed, the organic layer was separated with methylene chloride, and 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

Bromo-6,6-dimethyl-6H-pyrrolo [3,2,1-de] acridine used in Step 3 of Preparation Example 1 was used instead of 3-bromopyrrolo [3,2,1- (2-nitrophenyl) pyrrolo [3,2,1-jk] carbazole was obtained by following the procedure of <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

(2-nitrophenyl) pyrrolo [3,2-d] pyridine instead of 6,6-dimethyl-3- (2-nitrophenyl) 2,1-jk] carbazole (4.51 g, 14.44 mmol) was used in place of the compound of Preparation Example 1, to thereby obtain the compound IC-5.

^{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 that 5,7-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 1, Step 1] to obtain 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

Bromo-6,6-dimethyl-6H-pyrrolo [3,2,1-de] acridine used in Step 3 of Preparation Example 1 was used instead of 2-bromopyrrolo [3,2,1- (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, 3H), 7.62 (m, 3H), 7.83 (m, 2H), 8.03 (m, 2H), 8.11 (d, 1H)

&Lt; Step 3 > IC -6 and IC Synthesis of -7

(2-nitrophenyl) pyrrolo [3,2-d] pyridine instead of the 6,6-dimethyl-3- (2-nitrophenyl) Compound IC-6 and compound IC-7 were obtained by carrying out the same processes as in <Step 4> of Preparation Example 1 except that 2,1-jk] carbazole (4.51 g, 14.44 mmol) was used.

Compound IC-6 ¹ H-NMR of: 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)

Compound IC-7 ¹ H-NMR of: 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

Except that 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, Step 1] to obtain 1-bromopyrrolo [3,2,1-jk] carbazole.

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

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

3-bromo-6,6-dimethyl-6H-pyrrolo [3,2,1-de] acridine used in Step 3 of Preparation Example 1 was used instead of 1-bromopyrrolo [ (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), 7.50 (m, 1H), 7.72 (m, 4H), 8.01 (m, 4H)

<Step 3> Synthesis of Compound IC-8

(2-nitrophenyl) pyrrolo [3,2-d] pyridine instead of the 6,6-dimethyl-3- (2-nitrophenyl) 2,1-jk] carbazole (4.51 g, 14.44 mmol) was used in place of iodomethane, to give compound IC-8.

^{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 compound IC-9 and IC-10

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

3-bromo-8,8-dimethyl-8H-indolo [3,2,1-de] acridine (10.9 g, 30.0 mmol) was dissolved in THF (100 ml) under a nitrogen stream, and 28% aqueous ammonia 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 reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . 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 isolated by column chromatography .

^{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 Compound IC-9 and IC-10

8,8-dimethyl-8H-indolo [3,2,1-de] acridin-3-amine (5.97 g, 20.0 mmol) was dissolved in H ₂ O / dioxane (10 ml / 90 ml) 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), And the mixture was stirred at 180 DEG C for 20 hours. After completion of the reaction, the reaction mixture was poured into 5% aqueous HCl solution, extracted with methylene chloride, and then filtered with MgSO ₄ . After removing the solvent from the filtered organic layer, the compound IC-9 (1.74 g, 5.4 mmol, yield: 27%) and compound IC-10 (1.75 g, 5.4 mmol, yield 27%) were obtained by column chromatography.

Compound ¹ H-NMR of the 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, 1 H), 9.94 (s, 1 H)

Compound IC-10 ¹ H-NMR of: 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, 1 H), 9.94 (s, 1 H)

[Preparation Example 8] Synthesis of compound IC-11 and IC-12

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

Except that 5-bromo-2-nitrophenylboronic acid (2.38 g, 9.67 mmol) was used in place of 2-nitrophenylboronic acid used in Step 3 of Preparation Example 2, the same procedure as Step 3 of Preparation Example 2 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

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

Compound ¹ H-NMR of the 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)

Compound IC-12 ¹ H-NMR of: 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 compound IC-13 and IC-14

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

2-bromopyrrolo [3,2,1-jk] carbazole (2.38 g, 8.80 mmol) was used instead of 3-bromopyrrolo [3,2,1-jk] carbazole used in Step 2 of Preparation Example 4, bromo-2-nitrophenylboronic acid (2.38 g, 9.67 mmol) was used in place of 5-bromo-2-nitrophenylboronic acid in Step 2 of Preparation Example 4, nitrophenyl) pyrrolo [3,2,1-jk] carbazole.

^{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 Compound IC-13 and IC-14

5-bromo-2-nitrophenyl was used instead of 6,6-dimethyl-3- (2-nitrophenyl) -6H-pyrrolo [3,2,1-de] acridine used in <Step 4> Compound IC-13 and IC-14 were obtained by carrying out the same processes as in [Step 4] of Preparation Example 1 except that pyrrolo [3,2,1-jk] carbazole (5.65 g, 14.44 mmol) .

Compound IC-13 ¹ H-NMR of: 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)

Compound IC-14 ¹ H-NMR of: 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

2- (4-bromophenyl) triphenylene (10.18 g, 26.57 mmol), Cu powder (0.17 g, 2.66 mmol), K ₂ Was mixed with CO ₃ (3.66 g, 26.57 mmol), Na ₂ SO ₄ (3.78 g, 26.57 mmol) and nitrobenzene (100 ml), followed by stirring at 190 ° C for 12 hours.

After the reaction was completed, the nitrobenzene was removed, the organic layer was separated with methylene chloride, and 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 5.23 g (yield: 63%) of the compound C-1.

GC-Mass (calculated: 624.77 g / mol, measured: 624 g / mol)

[Synthesis Example 2] Synthesis of Compound C-2

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, , The compound C-2 (5.06 g, yield: 58%) was obtained.

GC-Mass (calculated: 656.84 g / mol, measured: 656 g / mol)

[Synthesis Example 3] Synthesis of Compound C-3

The procedure of Synthesis Example 1 was repeated 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%).

GC-Mass (calculated: 475.58 g / mol, measured: 475 g / mol)

[Synthesis Example 4] Synthesis of Compound C-4

2-chloro-4,6-diphenylpyrimidine (2.09 g, 7.85 mmol), NaH (2.11 g, 8.78 mmol) and DMF (1.89 g, 5.85 mmol) were added to a solution of compound IC- 80 ml), and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, water was added thereto, and the solid compound was filtered and purified by column chromatography to obtain Compound C-4 (2.42 g, yield: 75%).

GC-Mass (calculated: 522.67 g / mol, measured: 522 g / mol)

[Synthesis Example 5] Synthesis of Compound C-5

Except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.09 g, 7.85 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 4, 4, the compound C-5 (2.62 g, yield 81%) was obtained.

GC-Mass (calculated: 553.65 g / mol, measured: 553 g / mol)

[Synthesis Example 6] Synthesis of Compound C-6

The procedure of Synthesis Example 1 was repeated 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%).

GC-Mass (calculated: 565.70 g / mol, measured: 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) was used in place of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1 ), The procedure of Synthesis Example 1 was repeated to obtain Compound C-7 (6.02 g, yield: 63%).

GC-Mass (calculated: 718.85 g / mol, measured: 718 g / mol)

[Synthesis Example 8] Synthesis of Compound C-8

Except that 10- (4-bromophenyl) -9,9-dimethyl-9,10-dihydroacridine (9.64 g, 26.57 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1, Compound C-8 (6.12 g, yield: 77%) was obtained by carrying out the same procedure as in Example 1.

GC-Mass (theory: 605.77 g / mol, measurement: 605 g / mol)

[Synthesis Example 9] Synthesis of Compound C-9

The same procedure as in Synthesis Example 1 was repeated, except that (4-bromophenyl) triphenylsilane (11.0 g, 26.57 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1, 6.81 g, yield: 78%).

GC-Mass (calculated: 656.89 g / mol, measured: 656 g / mol)

[Synthesis Example 10] Synthesis of Compound C-10

Except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (10.28 g, 26.57 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1 , The same procedure as in Synthesis Example 1 was conducted to obtain Compound C-10 (7.03 g, yield: 84%).

GC-Mass (calculated: 629.75 g / mol, measured: 629 g / mol)

[Synthesis Example 11] Synthesis of Compound C-11

(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 (6.94 g, yield: 74%) was obtained by carrying out the same processes as in Synthesis Example 1, except that the compound C-11 (12.30 g, 26.57 mmol) was used.

GC-Mass (calculated: 705.85 g / mol, measured: 705 g / mol)

[Synthesis Example 12] Synthesis of Compound C-12

(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 (6.47 g, yield: 69%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that the compound C-12 (12.30 g, 26.57 mmol) was used.

GC-Mass (calculated: 705.85 g / mol, measured: 705 g / mol)

[Synthesis Example 13] Synthesis of Compound C-13

(7-bromo-9,9-dimethyl-9H-fluoren-2-yl) -4,6-diphenyl-1,3,5-triazine was used in place of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1 (6.14 g, yield: 62%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that the compound (13.36 g, 26.57 mmol) was used.

GC-Mass (calculated: 745.91 g / mol, measured: 745 g / mol)

[Synthesis Example 14] Synthesis of Compound C-14

Instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1, N - ([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) - [ -amine (12.30 g, 26.57 mmol), the compound C-14 (8.39 g, yield: 88%) was obtained.

GC-Mass (717.90 g / mol, measured: 717 g / mol)

[Synthesis Example 15] Synthesis of Compound C-15

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

GC-Mass (calculated: 757.96 g / mol, measured: 757 g / mol)

[Synthesis Example 16] Synthesis of Compound C-16

([1,1'-biphenyl] -4-yl) -2-bromo-9,9-dimethyl-7-phenyl-9,10- Compound C-16 (5.74 g, yield: 57%) was obtained in the same manner as in Synthesis Example 1, except that dihydroacridine (13.68 g, 26.57 mmol) was used.

GC-Mass (calculated: 757.96 g / mol, measured: 757 g / mol)

[Synthesis Example 17] Synthesis of Compound C-17

The procedure of Synthesis Example 10 was repeated except that the compound IC-2 (4.28 g, 13.29 mmol) synthesized in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 10 to obtain the compound C-17 5.02 g, yield: 60%).

GC-Mass (calculated: 629.75 g / mol, measured: 629 g / mol)

[Synthesis Example 18] Synthesis of Compound C-18

The same procedure as in Synthesis Example 11 was carried out except that the compound IC-2 (4.28 g, 13.29 mmol) synthesized in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 11 to obtain the compound C-18 7.88 g, yield: 84%).

GC-Mass (calculated: 705.85 g / mol, measured: 705 g / mol)

[Synthesis Example 19] Synthesis of Compound C-19

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

GC-Mass (calculated: 705.85 g / mol, measured: 705 g / mol)

[Synthesis Example 20] Synthesis of Compound C-20

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

GC-Mass (calculated: 629.75 g / mol, measured: 629 g / mol)

[Synthesis Example 21] Synthesis of Compound C-21

The procedure of Synthesis Example 11 was repeated except that the compound IC-3 (4.28 g, 13.29 mmol) synthesized in Preparation Example 2 was used instead of the compound IC-1 used in Synthesis Example 11 to obtain the compound C-21 6.56 g, yield: 70%).

GC-Mass (calculated: 705.85 g / mol, measured: 705 g / mol)

[Synthesis Example 22] Synthesis of Compound C-22

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

GC-Mass (calculated: 705.85 g / mol, measured: 705 g / mol)

[Synthesis Example 23] Synthesis of Compound C-23

The procedure of Synthesis Example 10 was repeated except that the compound IC-4 (4.28 g, 13.29 mmol) synthesized in Preparation Example 3 was used instead of the compound IC-1 used in Synthesis Example 10 to obtain the compound C-23 7.28 g, yield: 87%).

GC-Mass (calculated: 629.75 g / mol, measured: 629 g / mol)

[Synthesis Example 24] Synthesis of Compound C-24

The same procedure as in Synthesis Example 11 was conducted, except that the compound IC-4 (4.28 g, 13.29 mmol) used in Preparation Example 3 was used instead of the compound IC-1 used in Synthesis Example 11 to obtain the compound C-24 6.75 g, yield: 72%).

GC-Mass (calculated: 705.85 g / mol, measured: 705 g / mol)

[Synthesis Example 25] Synthesis of Compound C-25

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

GC-Mass (calculated: 705.85 g / mol, measured: 705 g / mol)

[Synthesis Example 26] Synthesis of Compound C-26

The procedure of Synthesis Example 10 was repeated except that the compound IC-5 (4.28 g, 13.29 mmol) synthesized in Preparation Example 4 was used instead of the compound IC-1 used in Synthesis Example 10 to obtain the compound C-26 5.07 g, yield: 65%).

GC-Mass (calculated: 587.67 g / mol, measured: 587 g / mol)

[Synthesis Example 27] Synthesis of Compound C-27

The procedure of Synthesis Example 11 was repeated except that the compound IC-5 (4.28 g, 13.29 mmol) synthesized in Preparation Example 4 was used instead of the compound IC-1 used in Synthesis Example 11 to obtain the compound C-27 5.82 g, yield: 66%).

GC-Mass (calculated: 663.77 g / mol, measured: 663 g / mol)

[Synthesis Example 28] Synthesis of Compound C-28

The procedure of Synthesis Example 12 was repeated except that the compound IC-5 (4.28 g, 13.29 mmol) synthesized in Preparation Example 4 was used instead of the compound IC-1 used in Synthesis Example 12 to obtain the compound C-28 6.35 g, yield: 72%).

GC-Mass (calculated: 663.77 g / mol, measured: 663 g / mol)

[Synthesis Example 29] Synthesis of Compound C-29

The procedure of Synthesis Example 10 was repeated except that the compound IC-6 (4.28 g, 13.29 mmol) synthesized in Preparation Example 5 was used instead of the compound IC-1 used in Synthesis Example 10 to obtain the compound C-29 4.45 g, yield: 57%).

GC-Mass (calculated: 587.67 g / mol, measured: 587 g / mol)

[Synthesis Example 30] Synthesis of Compound C-30

The same procedure as in Synthesis Example 11 was carried out except that the compound IC-6 (4.28 g, 13.29 mmol) synthesized in Preparation Example 5 was used instead of the compound IC-1 used in Synthesis Example 11 to obtain the compound C-30 4.32 g, yield: 49%).

GC-Mass (calculated: 663.77 g / mol, measured: 663 g / mol)

[Synthesis Example 31] Synthesis of Compound C-31

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

GC-Mass (calculated: 663.77 g / mol, measured: 663 g / mol)

[ Synthetic example  32] Synthesis of Compound C-32

The procedure of Synthesis Example 10 was repeated except that the compound IC-7 (4.28 g, 13.29 mmol) synthesized in Preparation Example 5 was used instead of the compound IC-1 used in Synthesis Example 10 to obtain the compound C-32 6.01 g, yield: 77%).

GC-Mass (calculated: 587.67 g / mol, measured: 587 g / mol)

[Synthesis Example 33] Synthesis of Compound C-33

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

GC-Mass (calculated: 663.77 g / mol, measured: 663 g / mol)

[Synthesis Example 34] Synthesis of Compound C-34

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

GC-Mass (calculated: 663.77 g / mol, measured: 663 g / mol)

[Synthesis Example 35] Synthesis of Compound C-35

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

GC-Mass (calculated: 587.67 g / mol, measured: 587 g / mol)

[Synthesis Example 36] Synthesis of Compound C-36

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

GC-Mass (calculated: 663.77 g / mol, measured: 663 g / mol)

[Synthesis Example 37] Synthesis of Compound C-37

The procedure of Synthesis Example 12 was repeated except that the compound IC-8 (4.28 g, 13.29 mmol) synthesized in Preparation Example 6 was used instead of the compound IC-1 used in Synthesis Example 12 to obtain the compound C-37 6.88 g, yield: 78%).

GC-Mass (calculated: 663.77 g / mol, measured: 663 g / mol)

[Synthesis Example 38] Synthesis of Compound C-38

The procedure of Synthesis Example 10 was repeated except that the compound IC-9 (4.28 g, 13.29 mmol) synthesized in Preparation Example 7 was used instead of the compound IC-1 used in Synthesis Example 10 to obtain the compound C-38 6.44 g, yield: 77%).

GC-Mass (calculated: 629.75 g / mol, measured: 629 g / mol)

[Synthesis Example 39] Synthesis of Compound C-39

The procedure of Synthesis Example 11 was repeated except that the compound IC-9 (4.28 g, 13.29 mmol) synthesized in Preparation Example 7 was used instead of the compound IC-1 used in Synthesis Example 11 to obtain the compound C-39 5.63 g, yield: 60%).

GC-Mass (calculated: 705.85 g / mol, measured: 705 g / mol)

[Synthesis Example 40] Synthesis of Compound C-40

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

GC-Mass (calculated: 705.85 g / mol, measured: 705 g / mol)

[Synthesis Example 41] Synthesis of Compound C-41

The same procedure as in Synthesis Example 10 was carried out except that the compound IC-10 (4.28 g, 13.29 mmol) synthesized in Preparation Example 7 was used instead of the compound IC-1 used in Synthesis Example 10 to obtain the compound C-41 6.27 g, yield: 75%).

GC-Mass (calculated: 629.75 g / mol, measured: 629 g / mol)

[Synthesis Example 42] Synthesis of Compound C-42

The procedure of Synthesis Example 11 was repeated except that the compound IC-10 (4.28 g, 13.29 mmol) synthesized in Preparation Example 7 was used instead of the compound IC-1 used in Synthesis Example 11 to obtain the compound C-42 6.75 g, yield: 72%).

GC-Mass (calculated: 705.85 g / mol, measured: 705 g / mol)

[Synthesis Example 43] Synthesis of Compound C-43

The procedure of Synthesis Example 12 was repeated except that the compound IC-10 (4.28 g, 13.29 mmol) synthesized in Preparation Example 7 was used instead of the compound IC-1 used in Synthesis Example 12 to obtain the compound C-43 5.90 g, yield: 63%).

GC-Mass (calculated: 705.85 g / mol, measured: 705 g / mol)

[Synthesis Example 44] Synthesis of Compound C-44

The compound IC-11 (3.49 g, 7.31 mmol), 2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan -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 and H2O (30 ml, 8 ml) were mixed and stirred at 100 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and then filtered with MgSO ₄ . After removing the solvent from the filtered organic layer, the compound C-44 (2.37 g, yield: 46%) was obtained by column chromatography.

GC-Mass (calculated: 705.85 g / mol, measured: 705 g / mol)

[ Synthetic example  45] Synthesis of Compound C-45

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

GC-Mass (theory: 793.99 g / mol, measured: 793 g / mol)

[Synthesis Example 46] Synthesis of Compound C-46

Synthesis of 2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine Instead of N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-N- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- (2.19 g, yield: 36%) was obtained by carrying out the same processes as in Synthesis Example 44, except that the compound C-46 was used in place of the compound C-46 (4.94 g, 8.77 mmol) .

GC-Mass (calculated: 834.06 g / mol, measured: 833 g / mol)

[Synthesis Example 47] Synthesis of Compound C-47

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

GC-Mass (calculated: 834.06 g / mol, measured: 833 g / mol)

[Synthesis Example 48] Synthesis of Compound C-48

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

GC-Mass (calculated: 705.85 g / mol, measured: 705 g / mol)

[Synthesis Example 49] Synthesis of Compound C-49

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

GC-Mass (theory: 793.99 g / mol, measured: 793 g / mol)

[Synthesis Example 50] Synthesis of Compound C-50

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

GC-Mass (calculated: 834.06 g / mol, measured: 833 g / mol)

[Synthesis Example 51] Synthesis of Compound C-51

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

GC-Mass (calculated: 834.06 g / mol, measured: 833 g / mol)

[Example 1] Production of green organic EL device

Compound C-1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was prepared as follows.

Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech), and then the substrate was cleaned using UV for 5 minutes The substrate was transferred to a vacuum evaporator.

M-MTDATA (60 nm) / TCTA (80 nm) / Compound C-1 + 10% Ir (ppy) ₃ (80 nm) was formed on the ITO transparent electrode prepared above using the compound C- (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm).

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

[Examples 2 to 51] - Preparation of organic EL device

Except that the compounds C-2 to C-51 synthesized in Synthesis Examples 2 to 51 were used instead of the compound C-1 used as a host material in the formation of the light emitting layer in Example 1, Thereby preparing an organic EL device.

[Comparative Example 1] Production of green organic EL device

A green organic EL device was fabricated in the same manner as in Example 1, except that CBP was used in place of the compound C-1 used as a host material in forming the light emitting layer in Example 1. The structure of CBP used is as follows.

[Experimental Example]

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

Sample Host The 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 (C-1 to C-51) represented by the formula (1) according to the present invention as the host material of the light emitting layer, 1 &lt; / RTI &gt; green organic EL device.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, It is natural.

Claims (8)

A compound represented by the following formula (1):
[Chemical Formula 1]

(In the formula 1,
R ₁ to R ₅ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl, substituted or unsubstituted C ₂ to C ₄₀ alkenyl , A substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, a substituted or unsubstituted A C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₃ to C ₄₀ A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₁ to C ₄₀ alkylcarbonyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nucleus atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ ring An aryl phosphine oxide group and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group, or may be bonded to an adjacent group to form a condensed ring,
R ₁ and R ₂ are condensed with each other to form a condensed ring represented by one of the following formulas (2) to (4), or one of R ₃ to R ₅ is condensed with an adjacent condensed ring to form a condensed ring represented by the following formula ;
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

R ₆ to R ₁₁ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted C ₂ to C ₄₀ alkenyl group , A substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, a substituted or unsubstituted A C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₃ to C ₄₀ A substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₁ to C ₄₀ alkylcarbonyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nucleus atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, substituted or unsubstituted C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ ring An arylphosphine oxide group and a substituted or unsubstituted C ₆ -C ₄₀ arylsilyl group, or may be bonded to an adjacent group to form a condensed ring;
Ar ₁ represents a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, a substituted or unsubstituted C _A substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, a substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ A substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a 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 arylboron group, a substituted or unsubstituted 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 aryl silyl group consisting of Selected from the group;
n is an integer of 0 to 4, provided that when n is an integer of 1 to 4, at least one Ra is independently selected from the group consisting of deuterium, halogen, cyano, substituted or unsubstituted C ₁ to C ₄₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ of the alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted number of 5 to 40 heteroaryl unsubstituted nucleus atoms aryl A substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ to C ₄₀ arylamine group, hwandoen C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted 3 to 40 nuclear atoms of a heterocycloalkyl group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl silyl group, a substituted or non-substituted of unsubstituted C ₁ ~ 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 each independently represent hydrogen, deuterium, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted five to twenty- 40 heteroaryl groups and substituted or unsubstituted C ₆ -C ₄₀ arylamine groups;
Wherein R ₁ to R _11, the alkyl group of Ra and Ar _1, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an aryl group, a cycloalkyl group, a heterocycloalkyl group, an alkyl silyl groups, alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an aryl silyl group, R ₂₁ to R ₂₃ represents an alkyl group, an aryl group, a heteroaryl group, and one or more substituents each of which introduces the aryl amine is each independently selected from 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 of the aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to the 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). The compound according to claim 1, wherein X is a single bond or C (R ₂₁ ) (R ₂₂ ). The compound according to claim 1, wherein Ar ₁ is selected from the group consisting of a substituted or unsubstituted C ₆ to C ₄₀ aryl group and a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms,
Wherein at least one of the substituents independently introduced into the aryl and heteroaryl groups of Ar ₁ is independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ aryl An amino group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, 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 &Lt; / RTI &gt; 3. The compound according to claim 1, wherein Ar &_lt; 1 &gt; is selected from the group consisting of Substituents A1 to A64:

The compound according to claim 1, which is selected from the group consisting of compounds represented by the following formulas (6) to (15):
[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

;
(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

(In the above Chemical Formulas 6 to 15,
R ₁ to R ₁₁ , Ra, Ar _1, X and n are each as defined in claim 1, A compound according to claim 1 selected from the group consisting of compounds represented by the following formulas INV-1 to INV-20:

(In the formulas (INV-1 to INV-20)
R ₁ to R ₁₁ , Ra, Ar ₁ and n are as defined in claim 1, respectively. 1. An organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound according to any one of claims 1 to 6. The organic electroluminescent device according to claim 7, wherein the organic compound layer containing the compound is a light emitting layer.