KR101634849B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device including the same. The organic electroluminescent device includes the organic compound in at least one organic layer, preferably a light emitting layer, thereby improving the luminous efficiency, driving voltage, and life span of the device.

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 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.

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. 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 are the same or different and each 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 - aryl of C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted nuclear atoms of 5 to 40 heteroaryl group, a substituted or unsubstituted in the ring C ₆ ~ C ₄₀ of the oxy 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 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 of the arylboronic group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, aryl phosphine oxide substituted or unsubstituted C ₆ ~ C ₄₀ group and A substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group;

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;

Here, 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 A halogen atom, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkoxy group, an aryloxy 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, an aryl boronic of C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ values in the aryl phosphine oxide group, and a C ₆ ~ 1 or more substituents selected from aryl silyl group consisting of C ₄₀ May be, they can only when the substituent in the plurality, 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 organic layer containing the compound is a light emitting layer, and the compound can be used as a host material.

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 compounds according to the present invention can be prepared by reacting a 5-membered heterocyclic moiety (such as indene, benzothiophene, benzofuran, benzoyl silane ) Are condensed to form a basic skeleton, and various substituents are bonded to this basic skeleton, which is characterized by being represented by the above formula (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 may have a wide band gap due to the condensed structure of a 5-membered heterocyclic moiety in which an indole moiety or benzene is condensed at the terminal of an 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. The energy level can be controlled according to the above-mentioned substituents, so that it has a wide band gap (sky blue to red), and thus is applicable not only to the light emitting layer but also to a hole transport layer, a hole injection layer, an electron transport layer, .

In addition, since the compound of Formula 1 is significantly increased in molecular weight due to various aromatic ring substituents introduced therein, the glass transition temperature can be improved, and thus it can have higher thermal stability than conventional CBP . In addition, the condensation of the indole moiety or the 5-membered heterocyclic moiety condensed with benzene at the end of the indazole moiety can not only improve the thermal stability of the compound, It is also effective in inhibiting the crystallization of the organic layer included. 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, 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 alkyl group of boron, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group of boron, a substituted or unsubstituted C ₆ ~ C _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 adjacent groups to form a condensed May form a ring,

Preferably, R ₁ to R ₅ are the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl having 5 to 40 nucleus And a substituted or unsubstituted C ₆ to C ₄₀ arylamine group.

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 group and an aryl silyl group each independently selected from deuterium, halogen, a cyano group, an alkenyl group of C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ 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 An 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, a C ₆ to 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 over ₄₀ per selected from the group consisting of aryl silyl group of the substituted species of Itdoe may be substituted with, 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 fused with 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 >

Wherein Ar ₁ to Ar ₆ are the same or different from each other and each 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 ~ C ₄₀ of the alkynyl group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl group, a substituted or unsubstituted nuclear atoms of 5 to 40 heteroaryl group, a substituted or unsubstituted C ₆ ~ aryloxy of C ₄₀ A substituted or unsubstituted C ₁ to C ₄₀ alkyl 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 aryl group, 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 alkylsulfonyl group, C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted aryl phosphine oxide of a C ₆ ~ C ₄₀ ring And it is selected from the group consisting of aryl silyl substituted or unsubstituted C ₆ ~ C _40.

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 group and an aryl silyl group each independently selected from deuterium, halogen, a cyano group, an alkenyl group of C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ 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 An 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, a C ₆ to 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 over ₄₀ per selected from the group consisting of aryl silyl group of the substituted species of Group, provided that when there are a plurality of substituents, they may be the same as or different from each other.

Preferably, Ar ₁ to Ar ₆ are the same or different from each other, and each independently represents a substituted or unsubstituted C ₆ to C ₄₀ aryl group and a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms Lt; / RTI >

The aryl and heteroaryl groups 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 to C ₄₀ alkynyl , 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 , C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, and a C ₆ ~ C over ₄₀ per selected from the group consisting of aryl silyl species of substituents , Provided that when the substituents are plural, they may be the same or different.

R ₆ to R ₉ 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 alkyl 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 C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted C ₆ ~ selected from the group consisting of C ₄₀ or aryl silyl, or adjacent groups that combine to form a condensed ring.

Preferably, R ₆ to R ₉ are the same or different and 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 it may be selected from the group consisting of a substituted or unsubstituted C ₆ ~ C ₄₀ aryl amine.

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 group and an aryl silyl group each independently selected from deuterium, halogen, a cyano group, an alkenyl group of C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ 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 An 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, a C ₆ to 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 over ₄₀ per selected from the group consisting of aryl silyl group of the substituted species of Can be optionally substituted, may be just when the plurality of substituents, the same or different from each other in.

In the compounds of formula (1) according to the 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 shown below, but are not limited thereto.

In the compound of Formula 1, Ar ₁ to Ar ₆ may be the same or different from each other, and each independently selected from the group consisting of Substituents A 1 to A 66, but is not limited thereto.

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 , Ar _1, 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 a compound represented by the above-mentioned formula (1), preferably a compound represented by any one of the above formulas (3) to (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 formula (1), preferably the compound represented by any one of the above formulas (3) to (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> Synthesis of 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -2H-indazole

(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.

After the reaction was completed, the organic layer was extracted with ethyl acetate, the water was removed with MgSO ₄ and the organic layer was purified by column chromatography (Hexane: EA = 10: 1 (v / v) 4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -2H-indazole (22.49 g, yield: 72%).

^{1 H-NMR: δ 1.24 (} s, 12H), 7.45 (s, 1H), 7.55 (2, 1H), 7.63 (d, 1H), 7.75 (d, 1H), 13.81 (s, 1H)

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

1-bromo-2-nitrobenzene (15.23 g, 75.41 mmol) and 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl) -2H-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 organic layer was extracted with methylene chloride, and then MgSO ₄ was added thereto, followed by filtration. The solvent was removed from the obtained organic layer and then the organic layer was purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain 5- (2-nitrophenyl) -2H-indazole (13.64 g, ).

^{1 H-NMR: δ 7.50 (} m, 2H), 7.80 (m, 6H), 13.81 (s, 1H)

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

(2-nitrophenyl) -2H-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, the organic layer was purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain 5- (2-nitrophenyl) -2-phenyl- g, yield: 71%).

¹ H-NMR: 8 7.46 (t, IH), 7.60 (m, 6H), 7.91 (t, IH), 8.05 (m, 3H), 8.39

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

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

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

Compound ^IC-1 1 H-NMR of: δ 7.29 (t, 1H) , 7.55 (m, 8H), 8.12 (d, 1H), 8.32 (d, 1H), 8.55 (s, 1H), 10.09 (s, 1H)

Compound IC-2 ¹ H-NMR of: δ 7.29 (t, 1H) , 7.56 (m, 8H), 7.85 (s, 1H), 8.12 (d, 1H), 8.52 (s, 1H), 10.21 (s, 1H)

[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) -2H-indazole

6-bromo-2H-indazole (25.22 g, 0.128 mol) was used instead of 5-bromo-2H-indazole used in Step 1 of Preparation Example 1 (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -2H-1-indolecarboxamide was carried out by following the procedure of <Step 1> of Preparation Example 1, indazole.

¹ H-NMR:? 1.25 (s, 12H), 7.45 (s, IH), 7.56 (m, 2H), 7.75

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

Step 1 of Preparation Example 2 was used instead of 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -2H-indazole used in <Step 2> (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -2H-indazole (22.09 g, 90.49 mmol) (2-nitrophenyl) -2H-indazole was obtained by following the procedure of <Step 2> of Preparation Example 1, except that

¹ H-NMR:? 7.19 (d, IH), 7.60 (m, 3H), 8.00 (m, 4H)

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

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

^{1 H-NMR: δ 7.58 (} m, 7H), 7.95 (m, 5H), 8.53 (s, 1H)

&Lt; Step 4 > IC -3 and IC Synthesis of -4

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

Compound IC-3 ¹ H-NMR of: δ 7.27 (m, 2H) , 7.56 (m, 7H), 7.92 (d, 1H), 8.13 (d, 1H), 8.54 (s, 1H), 10.19 (s, 1H)

Compound IC-4 ¹ H-NMR of: δ 7.29 (t, 1H) , 7.59 (m, 8H), 7.85 (s, 1H), 8.11 (d, 1H), 8.54 (s, 1H), 10.22 (s, 1H)

[Preparation Example 3] Synthesis of Compound IC-5

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

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

^{1 H NMR: δ 1.26 (s} , 12H), 7.45 (t, 1H), 7.55 (s, 1H), 7.63 (d, 1H), 7.75 (d, 1H), 13.54 (s, 1H)

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

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

¹ H NMR:? 7.55 (m, 3H), 7.71 (m, 2H), 7.95

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

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

^{1 H NMR: δ 7.57 (m} , 8H), 7.90 (t, 1H), 8.01 (m, 2H), 8.29 (d, 1H), 8.55 (s, 1H)

<Step 4> Synthesis of Compound IC-5

(2-nitrophenyl) -2-phenyl-2H-indazole obtained in Step 3 of Preparation Example 3 was used instead of 5- (2-nitrophenyl) 2H-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 7.29 (t} , 1H), 7.58 (m, 7H), 8.09 (m, 2H), 8.35 (d, 1H), 8.56 (s, 1H), 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) -2H-indazole

Except that 7-bromo-2H-indazole (25.22 g, 0.128 mol) was used instead of 5-bromo-2H-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) -2H-indazole.

¹ H NMR: 8 1.25 (s, 12H), 7.44 (t, IH), 7.56 (m, 2H), 7.75

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

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

^{1 H NMR: δ 7.53 (m} , 3H), 7.67 (t, 1H), 7.90 (m, 4H), 13.47 (s, 1H)

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

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

^{1 H NMR: δ 7.56 (m} , 8H), 7.89 (m, 2H), 8.02 (m, 2H), 8.55 (s, 1H)

<Step 4> Synthesis of Compound IC-6

(2-nitrophenyl) -2-phenyl-2H-indazole obtained in Step 3 of Preparation Example 4 was used instead of 5- (2-nitrophenyl) 2H-indazole (5.01 g, 15.91 mmol) was used to obtain compound IC-6.

¹ H NMR: 8 7.29 (s, IH), 7.58 (m, 7H), 7.92 (d, 2H), 8.14

[Preparation Example 5] Synthesis of compound IC-7

Step 1 Synthesis of 2- (4,6-diphenyl-1,3,5-triazin-2-yl) -5- (2-nitrophenyl) -2H-indazole

Except that 2-bromo-4,6-diphenyl-1,3,5-triazine (21.62 g, 69.26 mmol) was used instead of the iodobenzene used in <Step 3> of Preparation Example 1, (4,6-diphenyl-1,3,5-triazin-2-yl) -5- (2-nitrophenyl) -2H-indazole was obtained.

^{1 H-NMR: δ 7.45 (} m, 6H), 7.65 (m, 2H), 7.90 (t, 1H), 8.03 (m, 2H), 8.38 (m, 7H)

<Step 2> Synthesis of Compound IC-7

(4,6-diphenyl-1,3-dioxolan-2-yl) benzamide obtained in Step 1 of Preparation Example 5 was used instead of 5- (2-nitrophenyl) Step 4 of Preparation Example 1 was repeated except that 5-triazin-2-yl) -5- (2-nitrophenyl) -2H-indazole (7.48 g, 15.91 mmol) Compound IC-7 was obtained.

¹ H-NMR:? 7.29 (t, 1 H), 7.49 (m, 8H), 7.63 (d,

[Preparation Example 6] Synthesis of Compound IC-8

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

¹ H NMR:? 7.52 (m, 2H), 7.72 (m, 3H), 7.97

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

5-bromo-2-nitrophenyl) -2H-indazole (prepared in Step 1 of Preparation Example 6) was used instead of 5- (2-nitrophenyl) (5-bromo-2-nitrophenyl) -2-phenyl-2H-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 7.45 (t} , 1H), 7.60 (m, 5H), 7.72 (s, 1H), 7.98 (d, 1H), 8.07 (s, 1H), 8.19 (d, 1H), 8.38 (d , &Lt; / RTI &gt; 1H), 8.52 (s, 1H)

<Step 3> Synthesis of 7-bromo-2-phenyl-2,10-dihydropyrazolo [4,3-a]

(5-bromo-2-nitrophenyl) -2-phenyl-2H-indazole obtained in Step 2 of Preparation Example 6 was used instead of 5- (2-nitrophenyl) 2-phenyl-2H-indazole (6.27 g, 15.91 mmol) was used in place of 7-bromo-2-phenyl-2,10- dihydropyrazolo [ 4,3-a] carbazole.

^{1 H-NMR: δ 7.54 (} m, 8H), 8.03 (s, 1H), 8.33 (d, 1H), 8.53 (s, 1H), 10.55 (s, 1H)

<Step 4> Synthesis of Compound IC-8

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

^{1 H NMR: δ 7.25 (d} , 1H), 7.58 (m, 11H), 7.72 (s, 1H), 7.88 (d, 1H), 8.32 (d, 1H), 8.53 (s, 1H)

[ 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 . After removing the solvent of the organic layer, the organic layer 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)

[Synthesis 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)

[Synthesis 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)

[Synthesis Example 4] Synthesis of Compound C-4

The procedure of Synthesis Example 1 was repeated except that 2-chloro-4,6-diphenylpyrimidine (7.08 g, 26.57 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1, -4 (5.11 g, yield: 75%).

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

[Synthesis Example 5] Synthesis of Compound C-5

Except that 2-chloro-4,6-diphenyl-1,3,5-triazine (7.11 g, 26.57 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1, , The compound C-5 (4.71 g, yield: 69%) was obtained.

GC-Mass (theory: 514.58 g / mol, measured: 514 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 (4.34 g, yield: 62%).

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

[Synthesis Example 7] Synthesis of Compound C-7

3-bromo-9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazole (12.68 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)

[Synthesis 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)

[Synthesis 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)

[ Synthetic 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)

[Synthesis Example 12] Synthesis of Compound C-12

The procedure of Synthesis Example 1 was repeated except that 4- (4-bromophenyl) -2,6-diphenylpyrimidine (10.28 g, 26.57 mmol) was used instead of 2- (4-bromophenyl) triphenylene used in Synthesis Example 1 To obtain Compound C-12 (6.42 g, yield: 82%).

GC-Mass (calculated: 589.69 g / mol, measured: 589 g / mol)

[Synthesis Example 13] Synthesis of Compound C-13

The same procedure as in Synthesis Example 10 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 10 to obtain the compound C-13 5.65 g, yield: 72%).

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

[Synthesis Example 14] Synthesis of Compound C-14

The same procedure as in Synthesis Example 12 was carried out except that 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 Compound C-14 (5.95 g, yield: 76%).

GC-Mass (calculated: 589.69 g / mol, measured: 589 g / mol)

[Synthesis Example 15] Synthesis of Compound C-15

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 product-water IC-1 used in Synthesis Example 10 to obtain the compound C- 15 (6.75 g, yield: 86%).

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

[Synthesis Example 16] Synthesis of Compound C-16

The same procedure as in Synthesis Example 12 was carried out, except that 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 Compound C-16 (5.64 g, yield: 72%).

GC-Mass (calculated: 589.69 g / mol, measured: 589 g / mol)

[Synthesis Example 17] Synthesis of Compound C-17

The procedure of Synthesis Example 10 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 10 to obtain the compound C-17 4.63 g, yield: 59%).

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

[Synthesis Example 18] Synthesis of Compound C-18

The procedure of Synthesis Example 12 was repeated except that 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 Compound C-18 (4.93 g, yield: 63%).

GC-Mass (calculated: 589.69 g / mol, measured: 589 g / mol)

[Synthesis Example 19] Synthesis of Compound C-19

The procedure of Synthesis Example 10 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 10 to obtain Compound C-19 6.83 g, yield: 87%).

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

[Synthesis Example 20] Synthesis of Compound C-20

The same procedure as in Synthesis Example 12 was carried out except that 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 Compound C-20 (5.79 g, yield: 74%).

GC-Mass (calculated: 589.69 g / mol, measured: 589 g / mol)

[Synthesis Example 21] Synthesis of Compound C-21

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-21 4.55 g, yield: 58%).

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

[Synthesis Example 22] Synthesis of Compound C-22

The same procedure as in Synthesis Example 12 was conducted, except that 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 Compound C-22 g, yield: 49%).

GC-Mass (calculated: 589.69 g / mol, measured: 589 g / mol)

[Synthesis Example 23] Synthesis of Compound C-23

(3-bromophenyl) -4,6-diphenyl-1,3,4,5-triazine was synthesized by using the compound IC-7 (5.82 g, 13.29 mmol) synthesized in Preparation Example 7 instead of the compound IC- Compound C-23 (5.47 g, yield: 80%) was obtained in the same manner as in Synthesis Example 10, except that iodobenzene (5.42 g, 26.57 mmol) was used in place of 5-triazine.

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

[Synthesis Example 24] Synthesis of Compound C-24

Compound C-24 (5.18 g, 26.57 mmol) was obtained by following the same procedure as Synthesis Example 23, except that 4-bromo-1,1'-biphenyl (6.19 g, 26.57 mmol) was used in place of iodobenzene used in Synthesis Example 23, Yield: 66%).

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

[Synthesis Example 25] Synthesis of Compound C-25

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 H ₂ O (30 ml, 8 ml) were mixed, followed by stirring at 100 ° C for 12 hours. After termination of the reaction, the organic layer was extracted with ethyl acetate, and then filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, Compound C-25 (2.38 g, yield: 49%) was obtained by column chromatography.

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

[Synthesis Example 26] Synthesis of Compound C-26

2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine Except that 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (3.23 g, 8.77 mmol) The compound C-26 (1.71 g, yield: 39%) was obtained in the same manner as in Example 25.

GC-Mass (theory: 600.71 g / mol, measurement: 600 g / mol)

[ Example  1] Organic EL  Device fabrication

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 (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / 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 , CBP and BCP are as follows.

[Example 2] - [Example 26] - Preparation of green organic EL device

Except that the compounds C-2 to C-26 synthesized in Synthesis Examples 2 to 26 were used in place of the compound C-1 used as the light emitting host material in the formation of the light emitting layer in Example 1, Thereby preparing a green organic EL device.

[Comparative Example 1] Fabrication of organic EL device

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

[ Evaluation example  One]

The organic EL devices fabricated in Examples 1 to 26 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 C-1 6.89 515 40.5 Example 2 C-2 6.61 518 41.5 Example 3 C-3 6.68 515 41.3 Example 4 C-4 6.62 516 43.5 Example 5 C-5 6.87 518 41.7 Example 6 C-6 6.64 517 41.6 Example 7 C-7 6.91 518 38.8 Example 8 C-8 6.65 518 40.3 Example 9 C-9 6.91 517 40.2 Example 10 C-10 6.65 515 39.1 Example 11 C-11 6.91 517 39.2 Example 12 C-12 6.84 516 39.3 Example 13 C-13 6.66 516 39.4 Example 14 C-14 6.63 517 41.2 Example 15 C-15 6.68 517 41.2 Example 16 C-16 6.71 517 38.8 Example 17 C-17 6.69 517 41 Example 18 C-18 6.7 517 40.6 Example 19 C-19 6.71 517 40.7 Example 20 C-20 6.72 516 40.8 Example 21 C-21 6.89 516 39.8 Example 22 C-22 6.73 518 40.9 Example 23 C-23 6.73 516 38.4 Example 24 C-24 6.87 518 41.2 Example 25 C-25 6.75 516 41.2 Example 26 C-26 6.75 516 38.3 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, in the case of the green organic EL devices of Examples 1 to 26 using the compounds (C-1 to C-26) according to the present invention as a light emitting layer, the green organic EL of Comparative Example 1 using conventional CBP The device exhibits excellent performance in terms of efficiency and driving voltage as compared with the 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 each independently hydrogen,
Provided that at least one of R ₁ and R _2, R ₂ and R ₃ , R ₃ and R ₄ combine with each other to form a condensed heteroaromatic ring containing one N represented by the following formula 2;
(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 N (Ar ₂ );
Ar ₁ is selected from the group consisting of phenyl and a heteroaryl group having 6 nucleus atoms containing 1 to 3 N,
Ar ₂ is selected from the group consisting of a C ₆ to C ₁₂ aryl group and a heteroaryl group having 6 to 13 nuclear atoms containing 1 to 3 N,
R ₆ , R ₇ and R ₉ are each independently hydrogen,
R &lt; ₈ &gt; is selected from the group consisting of hydrogen, phenyl and heteroaryl groups having 13 nucleus atoms containing 1 to 3 N,
The heteroaryl group of Ar ₁ may be substituted with one or more substituents selected from the group consisting of C ₆ to C ₁₂ aryl groups, the aryl group and the heteroaryl group of Ar ₂ may be substituted with a C ₆ to C ₁₈ aryl group, A heteroaryl group having 6 to 16 nuclear atoms containing 1 to 3 S or N atoms, an arylamine group having ₁₂ carbon atoms, and an arylsilyl group having ₁₈ carbon atoms, The phenyl and heteroaryl groups of R ₈ may be substituted with one or more substituents selected from the group consisting of phenyl and heteroaryl groups having 6 nucleus atoms containing 1 to 3 N, provided that when the substituents are plural, Which may be the same or different. The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by any one 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. delete delete The method according to claim 1,
Wherein Ar ₁ and Ar ₂ are the same or different from each other and each independently represents a substituent group selected from the group consisting of the following substituents A1 to A3, A9, A16 to A18, A21, A22, A24 to A33, A35 to A37, A39 to A41, A46 to A48, A61 and A66. &Lt; RTI ID = 0.0 &gt;

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, 2, and 5. The method according to claim 6,
Wherein the organic compound layer containing the compound is a light emitting layer.