KR101561332B1 - New organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

(상기 화학식 1에서, R₁ 내지 R₅ 및 Ar₁ 은 각각 상세한 설명에서 정의한 바와 같음).The present invention relates to a compound represented by the following general formula (1) and an organic electroluminescent device comprising the same, wherein the compound represented by the following general formula (1) is contained in at least one organic layer, preferably a light emitting layer, Life and the like can be improved:
[Chemical Formula 1]

(Wherein R ₁ to R ₅ and Ar ₁ are each as defined in the detailed description).

Description

TECHNICAL FIELD [0001] The present invention relates to a novel organic compound and an organic electroluminescent device including the organic compound. [0002]

The present invention relates to a novel organic compound that can be used as a material for an organic electroluminescence device and an organic electroluminescence device including the same.

Studies on organic electroluminescent (EL) devices (hereinafter, simply referred to as 'organic EL devices') by blue electroluminescence using anthracene single crystals in 1965 have been carried out with reference to the observation of organic thin film luminosity 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. Since the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as much as that of the fluorescent material, studies on phosphorescent host materials as well as phosphorescent dopants have been conducted.

Until now, NPB, BCP, and Alq ₃ have been widely known as a hole injecting layer, a hole transporting layer, a hole blocking layer, and an electron transporting layer. Anthracene derivatives as a light emitting material have been reported as fluorescent dopant / host materials. Particularly, phosphorescent materials which have a great advantage in terms of efficiency improvement of light emitting materials include Firpic, Ir (ppy) ₃ , (acac) Ir (btp) as a blue, green, ₂ or the like is used. Up to now, 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.

However, existing materials have an advantage in terms of light emission characteristics, but their thermal stability is lowered due to their low glass transition temperature, so that they are not satisfactory in terms of lifetime in OLED devices. Therefore, development of materials with higher 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,

Provided that at least one of R ₁ and R _2, R ₂ and R ₃ , R ₃ and R ₄ is bonded to each other to form a condensed ring represented by the following formula (2)

In Formula 2,

The dotted line means a moiety in which at least one of R ₁ and R _2, R ₂ and R ₃ , R ₃ and R ₄ in Formula 1 is bonded to form a condensation;

X ₁ is selected from the group consisting of O, S, Se, N (Ar ₂ ), C (Ar ₃ ) (Ar ₄ ) and Si (Ar ₅ ) (Ar ₆ );

Ar ₁ to Ar ₆ each independently represent 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 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 ~ C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl amine group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus atoms from 3 to 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 ₆ to C ₄₀ arylboron group, A substituted or unsubstituted C ₆ to C ₄₀ arylphosphine group, a substituted or unsubstituted C ₆ to C ₄₀ arylphosphine oxide group, and a substituted or unsubstituted C ₆ to C ₄₀ ≪ / RTI >

R ₆ to R ₉ 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;

The R ₁ to R ₉ , And the alkyl group of Ar ₁ to Ar _6, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, alkylsilyl group, an alkyl boron group, an aryl Halogen, cyano, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl 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, C ₆ ~ C _40, alkyloxy group of C ₁ ~ C ₄₀ of, C _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 arylamine group, a C ₃ to C ₄₀ cycloalkyl group, to ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and the group consisting of C ₆ ~ C ₄₀ aryl group in the silyl Emitter is selected, and wherein when the substituent is a plurality, may be identical to 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 an indazole moiety to form a basic skeleton and various substituents are bonded to the basic skeleton. . 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 may have a wide band gap due to an indole moiety bonded to the terminal of the indazole moiety. In addition, since the compound has bipolar characteristics as a whole due to various aromatic ring substituents bonded to the basic skeleton, the compound can increase the binding force between holes and electrons. Therefore, when the 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 above-mentioned substituents and thus has a wide band gap (sky blue ~ 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.

In addition, due to various aromatic ring substituents introduced in many of the indole moieties, the molecular weight of the compound is significantly increased, so that the glass transition temperature can be improved, Lt; / RTI > Also, the indole moiety bonded to the end of the indazole moiety is condensed. Not only the thermal stability of the compound can be improved, but also the effect of inhibiting the crystallization of the organic layer containing the compound of the formula (1). 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 ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted selected from the group consisting arylsilyl of unsubstituted C ₆ ~ C ₄₀ of or, or adjacent groups combine to To form a condensed ring,

Preferably, R ₁ to R ₅ are hydrogen, deuterium, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, and a substituted or unsubstituted C _And an arylamine group having ₆ to ₄₀ carbon atoms.

In this case, the alkyl group of the R ₁ to R _5, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine 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 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 consisting of Doedoe selected from, in the case where the substituent a plurality, may be identical to or different from each other.

Provided that at least one of R ₁ and R _2, R ₂ and R ₃ , R ₃ and R ₄ is bonded to each other to form a condensed ring represented by the general formula (2). For example, when R ₁ and R ₂ are bonded to each other to form a condensed ring represented by Formula 2, a compound represented by Formula 3 or 4 is formed.

In the formula (2), the dotted line indicates a site where condensation is performed with at least one of R ₁ , R _2, R ₂ , R ₃ , R _3, and R ₄ in Chemical Formula 1.

Wherein X ₁ is O, S, Se, N ( Ar 2), C (Ar 3) (Ar 4) and Si (Ar ₅₎ is selected from the group consisting of (Ar _6), preferably N (Ar ₂₎ Lt; / RTI >

Each of Ar ₁ to Ar ₆ independently 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 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 C ₁ ~ C ₄₀ of the alkyloxy group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl amine group, a substituted or unsubstituted number of C ₃ to a cycloalkyl group, a substituted or unsubstituted of C ₄₀ unsubstituted nucleus atoms of 3 to 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 ₆ to C ₄₀ arylboron group , 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 of To C ₄₀ arylsilyl groups.

In this case, the alkyl group of said Ar ₁ to Ar _6, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine 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 silyl group consisting of , Provided that when a plurality of said substituents are plural, they may be the same as or different from each other.

Preferably, each of Ar ₁ to Ar ₆ is independently 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 nucleus atoms.

In this case, one or more substituents respectively introduced into the aryl group and the heteroaryl group of Ar ₁ to Ar ₆ are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, 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 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, and a C ₆ ~ C ₄₀ group consisting arylsilyl of , Provided that when the substituents are plural, they may be the same or different.

R ₆ to R ₉ 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, and preferably each independently represents hydrogen, deuterium , A substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, and a substituted or unsubstituted C ₆ to C ₄₀ arylamine group .

In this case, the alkyl group of the R ₆ to R _9, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine 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 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 consisting of Is selected from, but may be a case where the substituent is plural, the same or different from each other.

In the compound of formula (I) according to the present invention, preferably, R ₁ to R ₉ , and Ar ₁ to Ar ₆ are each independently selected from the group consisting of hydrogen, or substituents S1 to S206, no. Provided that at least one of R ₁ and R _{2 ,} R ₂ and R ₃ , R ₃ and R ₄ is bonded to each other to form a condensed ring represented by the general formula (2).

In the compound of Formula 1, Ar ₁ to Ar ₆ may be more preferably selected from the group consisting of Substituents A 1 to A 65 shown below.

Examples of the compound represented by the formula (1) according to the present invention include compounds represented by the following formulas (3) to (8), but are not limited thereto.

In the above Chemical Formulas 3 to 8,

R ₁ to R ₉ , and X ₁ are as defined in Formula 1, respectively.

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

As used herein, "unsubstituted alkyl" is a monovalent substituent derived from a straight 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.

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

"Unsubstituted alkynyl" is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include ethynyl, , 2-propynyl, and the like, but are not limited thereto.

"Unsubstituted aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, either alone or in combination with at least two rings. 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.

"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.

"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.

"Unsubstituted alkyloxy" means a monovalent substituent group represented by R'O-, wherein R 'represents an alkyl having 1 to 40 carbon atoms, and may have a linear, branched or 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.

"Unsubstituted arylamine" means an amine substituted with aryl having 6 to 60 carbon atoms.

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

"Unsubstituted heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one of the carbons, preferably one to three carbons, is replaced by N, O, or S Lt; / RTI > Non-limiting examples thereof include morpholine, piperazine, and the like.

"Alkylsilyl" is silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 40 carbon atoms.

"Fused ring" means a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused 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 (3) to the compound represented by the formula (8).

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 (3) to the compound represented by the formula (8). At this time, the compounds 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, the compound of the present invention can be used as a phosphorescent host of a light emitting layer. 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 and IC-2

≪ Step 1 > 5- (4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2- yl ) -1H- indazole  synthesis

(25.22 g, 0.128 mol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3 Dioxaborolane (48.58 g, 0.191 mol), Pd (dppf) Cl ₂ (5.2 g, 5 mol), KOAc (37.55 g, 0.383 mol) and 1,4- And the mixture was stirred at 130 DEG C for 12 hours.

Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) 5- (4,4,5,5- to give tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole (22.49 g, yield: 72%).

^{1 H-NMR: δ 1.24 (} s, 12H), 7.60 (d, 1H), 8.15 (m, 2H), 8.34 (d, 1H), 12.34 (s, 1H)

<Step 2> Synthesis of 5- (2- nitrophenyl ) -1H- indazole Synthesis of

1-bromo-2-nitrobenzene (15.23 g, 75.41 mmol) and 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl) -1H-indazole ( 22.09 g, 90.49 mmol), NaOH (9.05 g, 226.24 mmol) and _{THF / H 2 O (400 ml} / 200 ml) , and then, Pd (PPh ₃ at 40 ℃ mixing) ₄ (4.36 g, 5 mol%) was added thereto, and the mixture was stirred at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and then MgSO ₄ was added thereto. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain 5- (2-nitrophenyl) -1H-indazole (13.64 g, yield 63%).

¹ H-NMR: 8 7.64 (m, 2H), 7.90 (m, IH), 8.05 (m, 3H), 8.21

<Step 3> Synthesis of 5- (2-nitrophenyl) -1-phenyl-1H-indazole

(2-nitrophenyl) -1H-indazole (11.04 g, 46.17 mmol), iodobenzene (14.13 g, 69.26 mmol) and Cu powder (0.29 g, 4.62 mmol) obtained in Step 2 of Preparation Example 1 ), K ₂ CO ₃ (6.38 g, 46.17 mmol), Na ₂ SO ₄ (6.56 g, 46.17 mmol) and nitrobenzene (200 ml) were mixed and stirred at 190 ° C for 12 hours.

After completion of the reaction, nitrobenzene was removed, and the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent from the organic layer from which water had been removed, the residue was purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain 5- (2-nitrophenyl) -1- : 71%).

^{1 H-NMR: δ 7.48 (} t, 1H), 7.62 (m, 6H), 7.90 (m, 1H), 8.05 (m, 3H), 8.37 (m, 2H)

<Step 4> Synthesis of Compound IC-1 and IC-2

Phenyl-1H-indazole (5.01 g, 15.91 mmol), triphenylphosphine (10.43 g, 39.77 mmol) obtained in Step 3 of Preparation Example 1 and 1,2- dichlorobenzene (50 ml) were mixed and stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed and extracted with dichloromethane. The obtained organic layer was washed with MgSO ₄ and purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain a compound IC-1 (2.39 g, yield: 53% .

Compound ^IC-1 1 of H-NMR: δ 7.29 (t , 1H), 7.45 (m, 3H), 7.60 (m, 5H), 8.12 (d, 1H), 8.33 (d, 2H), 10.09 (s, 1H)

Compound IC-2 ¹ H-NMR of: δ 7.29 (t, 1H) , 7.47 (m, 2H), 7.60 (m, 6H), 7.85 (s, 1H), 8.12 (d, 1H), 8.37 (s, 1H), 10.21 (s, 1 H)

[Preparation Example 2] Synthesis of compound IC-3 and IC-4

<Step 1> Synthesis of 6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole

Step 1 of Preparation Example 1 was repeated except that 6-bromo-1H-indazole (25.22 g, 0.128 mol) was used instead of 5-bromo-1H-indazole used in Step 1 of Preparation Example 1, To obtain 6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole.

¹ H-NMR:? 1.25 (s, 12H), 7.48 (d, IH), 7.89 (m, 2H), 8.21

<Step 2> Synthesis of 6- (2-nitrophenyl) -1H-indazole

Step 1 of Preparation Example 2 was used instead of 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole used in Step 2 of Preparation Example 1, Except that the 6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole (22.09 g, 90.49 mmol) (2-nitrophenyl) -1H-indazole was obtained in the same manner as in < Step 2 >.

^{1 H-NMR: δ 7.49 (} d, 1H), 7.67 (t, 1H), 7.85 (s, 1H), 7.94 (m, 2H), 8.03 (m, 2H), 8.20 (s, 1H), 12.2 ( s, 1 H)

<Step 3> Synthesis of 6- (2-nitrophenyl) -1-phenyl-1H-indazole

(2-nitrophenyl) -1H-indazole (11.04 g, 46.17 mmol) obtained in Step 2 of Preparation Example 2 was used in place of 5- (2-nitrophenyl) -1H-indazole used in Step 1 of Preparation Example 1 (2-nitrophenyl) -1-phenyl-1H-indole was obtained by following the procedure of <Step 3> of Preparation Example 1,

^{1 H-NMR: δ 7.47 (} m, 2H), 7.62 (m, 5H), 7.83 (s, 1H), 7.95 (m, 2H), 8.02 (m, 2H), 8.39 (s, 1H)

<Step 4> Synthesis of Compound IC-3 and IC-4

(2-nitrophenyl) -1-phenyl-1H-indazole obtained in Step 3 of Preparation Example 2 was used instead of 5- (2-nitrophenyl) Compound IC-3 and IC-4 were obtained by following the procedure of <Step 4> of Preparation Example 1, except that 1H-indazole (5.01 g, 15.91 mmol) was used.

Compound IC-3 ¹ H-NMR of: δ 7.27 (m, 2H) , 7.45 (t, 1H), 7.54 (m, 6H), 7.95 (d, 1H), 8.12 (d, 1H), 8.37 (s, 1H), 10.53 (s, 1 H)

Compound IC-4 ¹ H-NMR of: δ 7.29 (t, 1H) , 7.45 (t, 1H), 7.50 (m, 1H), 7.58 (m, 6H), 7.88 (s, 1H), 8.11 (d, 1H), 8.33 (s, 1 H), 10.64 (s, 1 H)

[Preparation Example 3] Synthesis of Compound IC-5

<Step 1> Synthesis of 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole

Step 1 of Preparation Example 1 was repeated except that 4-bromo-1H-indazole (25.22 g, 0.128 mol) was used instead of 5-bromo-1H-indazole used in Step 1 of Preparation Example 1, 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole was obtained.

¹ H NMR:? 1.26 (s, 12H), 7.43 (d, IH), 7.66

<Step 2> Synthesis of 4- (2-nitrophenyl) -1H-indazole

Step 1 of Preparation Example 3 was used instead of 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole used in <Step 2> Except that 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole (22.09 g, 90.49 mmol) The same procedure as in <Step 2> was conducted to obtain 4- (2-nitrophenyl) -1H-indazole.

^{1 H NMR: δ 7.49 (d} , 1H), 7.68 (m, 2H), 7.90 (t, 1H), 8.01 (m, 2H), 8.24 (m, 2H), 12.39 (s, 1H)

<Step 3> Synthesis of 4- (2-nitrophenyl) -1-phenyl-1H-indazole

(2-nitrophenyl) -1H-indazole (11.04 g, 46.17 g) obtained in Step 2 of Preparation Example 3 was used in place of 5- (2-nitrophenyl) -1H-indazole used in Step 3 of Preparation Example 1 (2-nitrophenyl) -1-phenyl-1H-indazole was obtained by following the procedure of <Step 3> of Preparation Example 1,

^{1 H NMR: δ 7.47 (m} , 2H), 7.64 (m, 6H), 7.90 (t, 1H), 8.00 (m, 2H), 8.31 (m, 2H)

&Lt; Step 4 > IC Synthesis of -5

(2-nitrophenyl) -1-phenyl-1H-indazole obtained in Step 3 of Preparation Example 3 was used instead of 5- (2-nitrophenyl) 1H-indazole (5.01 g, 15.91 mmol) was used in the same manner as in <Step 4> of Preparation Example 1 to obtain a compound IC-5.

^{1 H NMR: δ 7.30 (t} , 1H), 7.52 (m, 7H), 8.08 (m, 2H), 8.35 (m, 2H), 10.21 (s, 1H)

[Preparation Example 4] Synthesis of Compound IC-6

<Step 1> Synthesis of 7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole

Step 1> of Preparation Example 1 was repeated except that 7-bromo-1H-indazole (25.22 g, 0.128 mol) was used instead of 5-bromo-1H-indazole used in Step 1 of Preparation Example 1 The same procedure was followed to obtain 7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole.

¹ H NMR: 8 1.25 (s, 12H), 7.44 (s, 1H), 7.62 (d,

<Step 2> Synthesis of 7- (2-nitrophenyl) -1H-indazole

Step 1 of Preparation Example 4 was used instead of 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole used in <Step 2> (22.09 g, 90.49 mmol) obtained in PREPARATION EXAMPLE 1 was used instead of 7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) The procedure of Step 2 was repeated to obtain 7- (2-nitrophenyl) -1H-indazole.

¹ H NMR:? 7.62 (m, 3H), 7.95 (m, 4H), 8.22

<Step 3> Synthesis of 7- (2-nitrophenyl) -1-phenyl-1H-indazole

(2-nitrophenyl) -1H-indazole (11.04 g, 46.17 g) obtained in Step 2 of Preparation Example 4 was used instead of 5- (2-nitrophenyl) -1H-indazole used in Step 3 of Preparation Example 1 (2-nitrophenyl) -1-phenyl-1H-indazole was obtained by following the procedure of <Step 3> of Preparation Example 1,

^{1 H NMR: δ 7.58 (m} , 8H), 7.89 (m, 2H), 8.02 (m, 2H), 8.39 (s, 1H)

<Step 4> Synthesis of Compound IC-6

(2-nitrophenyl) -1-phenyl-1H-indazole obtained in Step 3 of Preparation Example 4 was used instead of 5- (2-nitrophenyl) 1H-indazole (5.01 g, 15.91 mmol) was used in the same manner as in <Step 4> of Preparation Example 1 to obtain a compound IC-6.

¹ H NMR: 8 7.28 (s, IH), 7.55 (m, 7H), 7.92 (d, 2H), 8.14

[ Preparation Example  5] Compound IC Synthesis of -7

<Step 1> Synthesis of 5- (2-nitrophenyl) -1-o-tolyl-1H-indazole

Except that 1-bromo-2-methylbenzene (11.85 g, 69.26 mmol) was used in place of the iodobenzene used in Step 3 of Preparation Example 1, the procedure of Step 3 of Preparation Example 1 was repeated to obtain 5 - (2-nitrophenyl) -1-o-tolyl-1H-indazole.

^{1 H-NMR: δ 1.92 (} s, 3H), 7.33 (m, 3H), 7.49 (d, 1H), 7.65 (m, 2H), 7.90 (t, 1H), 8.04 (m, 2H), 8.07 ( s, 1 H), 8.39 (m, 2 H)

<Step 2> Synthesis of Compound IC-7

(2-nitrophenyl) -1-o-butanol obtained in Step 1 of Preparation Example 5 was used instead of 5- (2-nitrophenyl) -1- The compound IC-7 was obtained by following the procedure of <Step 4> of Preparation Example 1, except that tolyl-1H-indazole (5.24 g, 15.91 mmol) was used.

^{1 H-NMR: δ 1.93 (} s, 3H), 7.35 (m, 5H), 7.49 (m, 2H), 7.63 (d, 1H), 8.11 (d, 1H), 8.35 (m, 2H), 10.11 ( s, 1 H)

[Preparation Example 6] Synthesis of Compound IC-8

<Step 1> Synthesis of 5- (5-bromo-2-nitrophenyl) -1H-indazole

Except that 2,4-dibromo-1-nitrobenzene (21.18 g, 75.41 mmol) was used instead of 1-bromo-2-nitrobenzene used in <Step 2> in Preparation Example 1, (5-bromo-2-nitrophenyl) -1H-indazole was obtained.

^{1 H NMR: δ 7.63 (d} , 1H), 7.73 (s, 1H), 7.99 (d, 1H), 8.06 (s, 1H), 8.21 (m, 2H), 8.37 (d, 1H), 12.13 (s , 1H)

<Step 2> Synthesis of 5- (5-bromo-2-nitrophenyl) -1-phenyl-1H-indazole

5-bromo-2-nitrophenyl) -1H-indazole (prepared in Step 1 of Preparation Example 6) was used instead of 5- (2-nitrophenyl) (5-bromo-2-nitrophenyl) -1-phenyl-1H-indazole was obtained in the same manner as in <Step 3> of Preparation Example 1, except that 14.69 g (46.17 mmol)

^{1 H NMR: δ 7.44 (t} , 1H), 7.60 (m, 5H), 7.72 (s, 1H), 7.97 (d, 1H), 8.07 (s, 1H), 8.19 (d, 1H), 8.38 (m , 2H)

<Step 3> Synthesis of 7-bromo-3-phenyl-3,10-dihydropyrrolo [3,2-a]

(5-bromo-2-nitrophenyl) -1-phenyl-1H-indazole obtained in Step 2 of Preparation Example 6 was used instead of 5- (2-nitrophenyl) Bromo-3-phenyl-3,10-dihydropyrrolo [2,3-d] pyrimidin-2-one was obtained by following the procedure of <Step 4> of Preparation Example 1, 3,2-a] carbazole.

¹ H-NMR:? 7.52 (m, 8H), 8.03 (s, IH), 8.33 (m, 2H), 10.55

<Step 4> Synthesis of Compound IC-8

Bromo-3-phenyl-3,10-dihydropyrrolo [3, 4-d] pyrimidine obtained in Step 3 of Preparation Example 6 was used instead of 5- (2-nitrophenyl) 2-a] carbazole (3.98 g, 11 mmol) was used in place of the compound obtained in Step 3 of Preparation Example 1, compound IC-8 was obtained.

^{1 H NMR: δ 7.25 (d} , 1H), 7.54 (m, 11H), 7.72 (s, 1H), 7.88 (d, 1H), 8.34 (m, 2H)

[Preparation Example 7] Synthesis of compound IC-9

<Step 1> Synthesis of 6- (5-bromo-2-nitrophenyl) -1H-indazole

2,4-dibromo-1-nitrobenzene (21.18 g, 75.41 mmol) was used instead of 1-bromo-2-nitrobenzene used in Step 2 of Preparation Example 1 and 5- (4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole (22.09 g, (5-bromo-2-nitrophenyl) -1H-indazole was obtained by following the procedure of <Step 2> of Preparation Example 1,

¹ H NMR: 8 7.49 (s, IH), 7.71 (s, IH), 7.80

<Step 2> Synthesis of 6- (5-bromo-2-nitrophenyl) -1-phenyl-1H-indazole

(5-bromo-2-nitrophenyl) -1H-indazole (prepared in Step 1 of Preparation Example 7) was used instead of 5- (2-nitrophenyl) 6-bromo-2-nitrophenyl) -1-phenyl-1H-indazole was obtained in the same manner as in <Step 3> of Preparation Example 1, except that 14.69 g (46.17 mmol)

¹ H NMR: 8 7.47 (m, 2H), 7.61 (m, 4H), 7.70 (s, , 1H)

<Step 3> Synthesis of 7-bromo-1-phenyl-1,10-dihydropyrazolo [3,4-a]

(5-bromo-2-nitrophenyl) -1-phenyl-1H-indazole obtained in Step 2 of Preparation Example 7 was used instead of 5- (2-nitrophenyl) 1-phenyl-1H-indazole (6.27 g, 15.91 mmol) was used in place of 7-bromo-1-phenyl- 3,4-a] carbazole.

¹ H-NMR:? 7.27 (s, 1H), 7.52 (m, 7H), 7.93 (d,

<Step 4> Synthesis of compound IC-9

Bromo-1-phenyl-1,10-dihydropyrazolo [3,3-b] pyridine obtained in Step 3 of Preparation Example 7 was used instead of 5- (2-nitrophenyl) 4-a] carbazole (3.98 g, 11 mmol) was used in place of the compound obtained in Step 3 of Preparation Example 1.

¹ H NMR:? 7.26 (m, 2H), 7.58 (m, IH), 7.74 (s, IH), 7.86

[ Synthetic example  1] Synthesis of Compound C-1

(3.76 g, 13.29 mmol), 2- (4-bromophenyl) triphenylene (10.18 g, 26.57 mmol), Cu powder (0.17 g, 2.66 mmol) synthesized in Preparation Example 1, 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, the nitrobenzene was removed, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain Compound C-1 (5.37 g, yield 69%).

GC-Mass (calculated: 585.69 g / mol, measured: 585 g / mol)

[ Synthetic example  2] Synthesis of Compound C-2

Except that 4- (4-bromophenyl) -6-phenyldibenzo [b, d] thiophene (11.03 g, 26.57 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1, The compound C-2 (4.92 g, yield: 60%) was obtained.

GC-Mass (calculated: 617.76 g / mol, measured: 617 g / mol)

[ Synthetic example  3] Synthesis of Compound C-3

The procedure of Synthesis Example 1 was repeated except that 2-bromo-6-phenylpyridine (6.22 g, 26.57 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1, (4.12 g, yield: 71%).

GC-Mass (calculated: 436.51 g / mol, measured: 436 g / mol)

[ Synthetic example  4] Synthesis of Compound C-4

(1.66 g, 5.85 mmol), 2-chloro-4,6-diphenylpyrimidine (2.09 g, 7.85 mmol), NaH (2.11 g, 8.78 mmol) synthesized in Preparation Example 1 and DMF ml) were mixed, followed by stirring at room temperature for 3 hours. After the reaction was completed, water was added thereto, and the solid product was filtered, and then purified by column chromatography to obtain Compound C-4 (2.25 g, yield: 75%).

GC-Mass (theory: 513.59 g / mol, measured: 513 g / mol)

[ Synthetic example  5] Synthesis of Compound C-5

Except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2.10 g, 7.85 mmol) was used instead of 2-chloro-4,6-diphenylpyrimidine used in Synthesis Example 4 4, the compound C-5 (2.07 g, yield: 69%) was obtained.

GC-Mass (theory: 514.58 g / mol, measured: 514 g / mol)

[ Synthetic 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 (4.34 g, yield: 62%).

GC-Mass (calculated: 526.63 g / mol, measured: 526 g / mol)

[ Synthetic example  7] Synthesis of Compound C-7

3-bromo-9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazole (12.68 g, 26.57 mmol) was used in place of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1 ), The same procedure as in Synthesis Example 1 was conducted to obtain Compound C-7 (5.24 g, yield: 58%).

GC-Mass (calculated: 679.77 g / mol, measured: 679 g / mol)

[Synthesis Example 8] Synthesis of Compound C-8

Except that 10- (4-bromophenyl) -9,9-dimethyl-9,10-dihydroacridine (9.67 g, 26.57 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1, Compound C-8 (5.72 g, yield: 76%) was obtained by carrying out the same procedure as in Example 1.

GC-Mass (calculated: 566.69 g / mol, measured: 566 g / mol)

[ Synthetic example  9] Synthesis of Compound C-9

The same procedure as in Synthesis Example 1 was repeated, except that (4-bromophenyl) triphenylsilane (11.04 g, 26.57 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1, 4.68 g, yield: 57%).

GC-Mass (theory: 617.81 g / mol, measured: 617 g / mol)

[ Synthetic example  10] Synthesis of Compound C-10

Except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (10.32 g, 26.57 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1 , Compound C-10 (6.28 g, yield: 80%) was obtained by carrying out the same processes as in Synthesis Example 1.

GC-Mass (calculated: 590.67 g / mol, measured: 590 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 (7.44 g, yield: 84%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that the compound C-11 (12.34 g, 26.57 mmol) was used.

GC-Mass (calculated: 666.77 g / mol, measured: 666 g / mol)

[ Synthetic 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 (7.26 g, yield: 82%) was obtained by following the same procedure as in Synthesis Example 1, except that the compound C-12 (12.34 g, 26.57 mmol) was used.

GC-Mass (calculated: 666.77 g / mol, measured: 666 g / mol)

[ Synthetic 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 (5.73 g, yield: 61%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that the compound C-13 (13.40 g, 26.57 mmol) was used.

GC-Mass (calculated: 706.83 g / mol, measured: 706 g / mol)

[ Synthetic 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 (12.66 g, 26.57 mmol), the same procedure as in Synthesis Example 1 was conducted to obtain Compound C-14 (6.31 g, yield: 70%).

GC-Mass (theory: 678.82 g / mol, measured: 678 g / mol)

[Synthesis Example 15] Synthesis of Compound C-15

Substituting N - ([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H-fluoren- 2 -amine (13.72 g , 26.57 mmol), the same procedure as in Synthesis Example 1 was conducted to obtain Compound C-15 (6.21 g, yield: 65%).

GC-Mass (calculated: 718.88 g / mol, measured: 718 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 (5.25 g, yield: 55%) was obtained in the same manner as in Synthesis Example 1, except that dihydroacridine (13.72 g, 26.57 mmol) was used.

GC-Mass (calculated: 718.88 g / mol, measured: 718 g / mol)

[ Synthetic example  17] Synthesis of Compound C-17

The procedure of Synthesis Example 10 was repeated except that the compound IC-2 (3.76 g, 13.29 mmol) synthesized in Preparation Example 1 was used instead of the compound IC-1 used in Synthesis Example 10 to obtain the compound C-17 5.65 g, yield: 72%).

GC-Mass (calculated: 590.67 g / mol, measured: 590 g / mol)

[ Synthetic example  18] Synthesis of Compound C-18

Compound C-18 (6.73 g, 13.29 mmol) was obtained by following the same procedure as in Synthesis Example 11, except that IC-2 (3.76 g, 13.29 mmol) synthesized in Preparation Example 1 was used instead of Compound IC- g, yield: 76%).

GC-Mass (calculated: 666.77 g / mol, measured: 666 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 (3.76 g, 13.29 mmol) synthesized in Preparation Example 1 was used instead of the compound IC-1 used in Synthesis Example 12 to obtain the compound C-19 7.26 g, yield: 82%).

GC-Mass (calculated: 666.77 g / mol, measured: 666 g / mol)

[ Synthetic example  20] Synthesis of Compound C-20

The procedure of Synthesis Example 10 was repeated except that the compound IC-3 (3.76 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 6.75 g, yield: 86%).

GC-Mass (calculated: 590.67 g / mol, measured: 590 g / mol)

[ Synthetic example  21] Synthesis of Compound C-21

The same procedure as in Synthesis Example 11 was conducted, except that the compound IC-3 (3.76 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 6.38 g, yield: 72%).

GC-Mass (calculated: 666.77 g / mol, measured: 666 g / mol)

[ Synthetic example  22] Synthesis of Compound C-22

The same procedure as in Synthesis Example 12 was conducted, except that the compound IC-3 (3.76 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 6.91 g, yield: 78%).

GC-Mass (calculated: 666.77 g / mol, measured: 666 g / mol)

[ Synthetic example  23] Synthesis of Compound C-23

The same procedure as in Synthesis Example 10 was carried out except that the compound IC-4 (3.76 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-23 4.63 g, yield: 59%).

GC-Mass (calculated: 590.67 g / mol, measured: 590 g / mol)

[ Synthetic example  24] Synthesis of Compound C-24

The same procedure as in Synthesis Example 11 was carried out except that the compound IC-4 (3.76 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-24 5.58 g, yield: 63%).

GC-Mass (calculated: 666.77 g / mol, measured: 666 g / mol)

[ Synthetic example  25] Synthesis of Compound C-25

The procedure of Synthesis Example 12 was repeated except that the compound IC-4 (3.76 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-25 6.29 g, yield: 71%).

GC-Mass (calculated: 666.77 g / mol, measured: 666 g / mol)

[ Synthetic example  26] Synthesis of Compound C-26

The same procedure as in Synthesis Example 10 was conducted, except that the compound IC-5 (3.76 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-26 6.83 g, yield: 87%).

GC-Mass (calculated: 590.67 g / mol, measured: 590 g / mol)

[ Synthetic example  27] Synthesis of Compound C-27

The same procedure as in Synthesis Example 11 was carried out except that the compound IC-5 (3.76 g, 13.29 mmol) synthesized in Preparation Example 3 was used instead of the compound IC-1 used in Synthesis Example 11 to obtain the compound C-27 6.55 g, yield: 74%).

GC-Mass (calculated: 666.77 g / mol, measured: 666 g / mol)

[ Synthetic example  28] Synthesis of Compound C-28

The procedure of Synthesis Example 12 was repeated except that the compound IC-5 (3.76 g, 13.29 mmol) synthesized in Preparation Example 3 was used instead of the compound IC-1 used in Synthesis Example 12 to obtain the compound C-28 6.64 g, yield: 75%).

GC-Mass (calculated: 666.77 g / mol, measured: 666 g / mol)

[ Synthetic example  29] Synthesis of Compound C-29

The procedure of Synthesis Example 10 was repeated except that the compound IC-6 (3.76 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-29 4.55 g, yield: 58%).

GC-Mass (calculated: 590.67 g / mol, measured: 590 g / mol)

[Synthesis Example 30] Synthesis of Compound C-30

The same procedure as in Synthesis Example 11 was conducted, except that the compound IC-6 (3.76 g, 13.29 mmol) synthesized in Preparation Example 4 was used instead of the compound IC-1 used in Synthesis Example 11 to obtain Compound C-30 4.34 g, yield: 49%).

GC-Mass (calculated: 666.77 g / mol, measured: 666 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 (3.76 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-31 6.11 g, yield: 69%).

GC-Mass (calculated: 666.77 g / mol, measured: 666 g / mol)

[ Synthetic example  32] Synthesis of Compound C-32

The procedure of Synthesis Example 10 was repeated except that the compound IC-7 (3.95 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 6.43 g, yield: 80%).

GC-Mass (theory: 604.70 g / mol, measurement: 604 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 (3.95 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 5.97 g, yield: 66%).

GC-Mass (theory: 680.80 g / mol, measurement: 680 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 (3.95 g, 13.29 mmol) used in Preparation Example 5 was used instead of the compound IC-1 used in Synthesis Example 12 to obtain Compound C-34 6.51 g, yield: 72%).

GC-Mass (theory: 680.80 g / mol, measurement: 680 g / mol)

[Synthesis Example 35] Synthesis of Compound C-35

The compound IC-8 (3.20 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 of the filtered organic layer, Compound C-35 (2.38 g, yield: 49%) was obtained by column chromatography.

GC-Mass (calculated: 666.77 g / mol, measured: 666 g / mol)

[Synthesis Example 36] Synthesis of Compound C-36

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- (2.15 g, yield: 39%) was obtained by following the same procedure as in Synthesis Example 35, except that 1,1'-biphenyl] -4-amine (4.59 g, 8.77 mmol) .

GC-Mass (calculated: 754.92 g / mol, measured: 754 g / mol)

[Synthesis Example 37] Synthesis of Compound C-37

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- (2.38 g, yield: 41%) was obtained by carrying out the same processes as in Synthesis Example 35, except that the compound C-37 was used instead of the compound C-37 (4.94 g, 8.77 mmol) .

GC-Mass (calculated: 794.98 g / mol, measured: 794 g / mol)

[Synthesis Example 38] Synthesis of Compound C-38

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- (2.67 g, yield: 46%) was obtained in the same manner as in Synthesis Example 35, except that the compound C-38 was used in place of the compound C-38.

GC-Mass (calculated: 794.98 g / mol, measured: 794 g / mol)

[Synthesis Example 39] Synthesis of Compound C-39

The same procedure as in Synthesis Example 35 was conducted, except that the compound IC-9 (3.20 g, 7.31 mmol) synthesized in Preparation Example 7 was used instead of the compound IC-8 used in Synthesis Example 35 to obtain the compound C-39 1.95 g, yield: 40%).

GC-Mass (calculated: 666.77 g / mol, measured: 666 g / mol)

[Synthesis Example 40] Synthesis of Compound C-40

The same procedure as in Synthesis Example 36 was conducted, except that the compound IC-9 (3.20 g, 7.31 mmol) synthesized in Preparation Example 7 was used instead of the compound IC-8 used in Synthesis Example 36 to obtain the compound C-40 1.76 g, yield: 32%).

GC-Mass (calculated: 754.92 g / mol, measured: 754 g / mol)

[Synthesis Example 41] Synthesis of Compound C-41

(C-41) was obtained in the same manner as in Synthesis Example 37, except that the compound IC-9 (3.20 g, 7.31 mmol) synthesized in Preparation Example 7 was used instead of the compound IC- 1.45 g, yield: 25%).

GC-Mass (calculated: 794.98 g / mol, measured: 794 g / mol)

[Synthesis Example 42] Synthesis of Compound C-42

The same procedure as in Synthesis Example 38 was conducted, except that the compound IC-9 (3.20 g, 7.31 mmol) synthesized in Preparation Example 7 was used instead of the compound IC-8 used in Synthesis Example 38 to obtain the compound C-42 2.15 g, yield: 37%).

GC-Mass (calculated: 794.98 g / mol, measured: 794 g / mol)

[Example 1] Production of 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 fabricated according to the following procedure.

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

(60 nm) / TCTA (80 nm) / Compound C-1 + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) on the ITO transparent electrode prepared above. ) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic EL device.

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

[Examples 2 to 42] - Preparation of organic EL device

The procedure of Example 1 was repeated, except that the compounds C-2 to C-42 synthesized in 4251 in Synthesis Example 2 were used instead of the compound C-1 used as the host material in the formation of the light emitting layer in Example 1 Thereby preparing an organic EL device.

[Comparative Example 1] Production of organic EL device

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

[Evaluation example]

The organic EL devices manufactured in Examples 1 to 42 and Comparative Example 1 were measured for driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2, and the results are shown in Table 1 below.

Sample Host The driving voltage (V) EL peak (nm) Current efficiency (cd / A) Example 1 Compound C-1 6.73 518 41.8 Example 2 Compound C-2 6.73 518 41.5 Example 3 Compound C-3 6.74 517 41.3 Example 4 Compound C-4 6.64 516 43.5 Example 5 Compound C-5 6.65 516 41.7 Example 6 Compound C-6 6.66 516 42.1 Example 7 Compound C-7 6.66 516 38.8 Example 8 Compound C-8 6.9 517 40.3 Example 9 Compound C-9 6.91 517 40.2 Example 10 Compound C-10 6.75 516 39.1 Example 11 Compound C-11 6.68 515 39.2 Example 12 Compound C-12 6.69 517 39.3 Example 13 Compound C-13 6.69 516 39.4 Example 14 Compound C-14 6.71 515 41.2 Example 15 Compound C-15 6.73 515 41.2 Example 16 Compound C-16 6.75 516 41.1 Example 17 Compound C-17 6.75 517 41 Example 18 Compound C-18 6.81 516 40.6 Example 19 Compound C-19 6.83 518 40.7 Example 20 Compound C-20 6.84 517 40.8 Example 21 Compound C-21 6.85 516 40.9 Example 22 Compound C-22 6.86 518 40.9 Example 23 Compound C-23 6.87 516 41.1 Example 24 Compound C-24 6.87 516 41.2 Example 25 Compound C-25 6.88 517 41.2 Example 26 Compound C-26 6.89 515 41.3 Example 27 Compound C-27 6.89 517 41.3 Example 28 Compound C-28 6.91 516 41.8 Example 29 Compound C-29 6.91 518 42 Example 30 Compound C-30 6.7 518 42.2 Example 31 Compound C-31 6.65 516 42.6 Example 32 Compound C-32 6.66 516 42.8 Example 33 Compound C-33 6.64 516 41.3 Example 34 Compound C-34 6.88 516 39.8 Example 35 Compound C-35 6.72 516 40.5 Example 36 Compound C-36 6.62 518 38.8 Example 37 Compound C-37 6.63 518 40.6 Example 38 Compound C-38 6.65 518 41.3 Example 39 Compound C-39 6.61 516 41.6 Example 40 Compound C-40 6.73 517 40.4 Example 41 Compound C-41 6.68 517 40.9 Example 42 Compound C-42 6.62 517 41.2 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, the green organic EL devices of Examples 1 to 42, in which the compounds C-1 to C-4 according to the present invention were used as the host material of the light emitting layer, It was confirmed that the organic EL device exhibited better current efficiency and better driving voltage than the 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 (7)

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 from each other and each independently selected from the group consisting of hydrogen, deuterium, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₄₀ aryl group, and a heteroaryl group having 5 to 40 nuclear atoms And,
Provided that at least one of R ₁ and R _2, R ₂ and R ₃ , R ₃ and R ₄ is bonded to each other to form a condensed ring represented by the following formula (2)
(2)

In the formula (2)
X ₁ is selected from the group consisting of O, S, Se, N (Ar ₂ ), C (Ar ₃ ) (Ar ₄ ) and Si (Ar ₅ ) (Ar ₆ );
Each of Ar ₁ to Ar ₆ is independently selected from the group consisting of a C ₆ to C ₄₀ aryl group and a heteroaryl group having 5 to 40 nuclear atoms;
R ₆ to R ₉ are the same or different and each independently selected from the group consisting of hydrogen, deuterium, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₄₀ aryl group, and a heteroaryl group having 5 to 40 nuclear atoms ;
The alkyl, aryl and heteroaryl groups of R ₁ to R ₉ and the aryl and heteroaryl groups of Ar ₁ to Ar ₆ are each independently a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₄₀ aryl group, nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ substituted with C ₄₀ arylamine group, and a C ₆ ~ C ₄₀ aryl silyl group with one or more substituents selected from the group consisting of or is unsubstituted, wherein the substituent is a plurality They may be the same or different from each other). The compound according to claim 1, which is selected from the group consisting of the following formulas (3) to (8):
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

(In the above Chemical Formulas 3 to 8,
R ₁ to R ₉ , Ar ₁ and X ₁ are as defined in claim 1, respectively. The compound according to claim 1, wherein X ₁ is N (Ar ₂ )
Wherein Ar &lt; ₂ &gt; is as defined in claim 1. delete The compound according to claim 1, wherein Ar ₁ to Ar ₆ are each independently selected from the group consisting of Substituents A 1 to A 65:

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 compound layers comprises a compound according to any one of claims 1 to 3 and 5. The organic electroluminescent device according to claim 6, wherein at least one organic compound layer containing the compound is a light emitting layer.