KR101556819B1 - Organic compounds and organic electro luminescence device using the same - Google Patents

Abstract

The present invention relates to a compound represented by the following general formula (1) and an organic electroluminescent device including 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 significantly improved.

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 which can be used as a material for an organic electroluminescent device, and an organic electroluminescent device including the same, which improves the luminous efficiency, driving voltage and lifetime of the device.

The study of organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices') led to blue electroluminescence using anthracene single crystals in 1965 based on observations of organic thin films from 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 anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. The material used as the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.

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

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

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. In particular, the phosphor has a great advantage in improving the efficiency aspects of the light-emitting material materials _{Firpic, Ir (ppy) 3,} (acac) Ir (btp) 2 Ir metal complex compound is blue (blue), which includes the same as the green ( green and red dopant materials, and CBP is a phosphorescent host material.

However, existing materials have advantages in terms of light emitting properties, but they are not satisfactory in terms of lifetime in OLED devices because of low glass transition temperature and poor thermal stability. Therefore, development of materials with higher performance is required.

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, luminescent efficiency and the like.

The present invention provides a compound represented by the following formula (1).

In Formula 1,

R ₆ and R ₇ or R ₇ and R _8, at least one of which is to form the formula (2) with a condensed ring,

In Formula 2,

X is O, S, Se, N ( Ar 2), C (Ar 3) (Ar 4), Si (Ar 5) (Ar 6), P selected from the group consisting of (Ar ₇₎ and B (Ar ₈₎ And,

R ₁ to R ₁₂ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, nitro, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ A substituted or unsubstituted C ₂ to C ₄₀ alkynyl 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 ₂ to C ₄₀ alkynyl group, An unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ ~ C ₆₀ of the aryloxy group, a substituted or unsubstituted C ₃ ~ C ₄₀ alkyl silyl group, a substituted or arylsilyl unsubstituted C ₆ ~ C ₆₀ group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkyl boron group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl group of boron, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl phosphine oxide group is selected from the pin, and the group consisting of a substituted or unsubstituted C ₆ ~ C ₆₀ aryl amine, these are combined tile adjacent may form a condensed ring,

Ar ₁ to Ar ₈ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, nitro, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ to C ₄₀ A substituted or unsubstituted C ₂ to C ₄₀ alkynyl 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 ₂ to C ₄₀ alkynyl group, An unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ ~ C ₆₀ of the aryloxy group, a substituted or unsubstituted C ₃ ~ C ₄₀ alkyl silyl group, a substituted or arylsilyl unsubstituted C ₆ ~ C ₆₀ group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkyl A boron group, a substituted or unsubstituted C ₆ to C ₆₀ arylboron group, a substituted or unsubstituted C ₆ to C ₆₀ arylphosphine group, a substituted or unsubstituted aryl group, Substituted C ₆ to C ₆₀ aryl phosphine oxide groups, and substituted or unsubstituted C ₆ to C ₆₀ arylamine groups,

In R ₁ to R ₁₂ and Ar ₁ to Ar ₈ , the substituent described in the term "substituted or unsubstituted", for example, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, , alkyloxy, aryloxy of time, an alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group, an arylamine group, each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, A C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, C ₆ ~ C ₄₀ aryl silyl group, C ₂ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide Group, and C ₆ With one or more substituents selected from the group consisting of arylamine ~ C ₆₀ can be replaced. When a plurality of substituents are introduced at this time, these substituents may be the same as or different from each other.

The present invention also provides an organic electroluminescent device comprising at least one organic material layer interposed between (i) an anode, (ii) a cathode, and (iii) an anode and a cathode, wherein at least one of the one or more organic layers One is an organic electroluminescent device comprising a compound represented by the general formula (1).

At least one of the one or more organic layers may be selected from the group consisting of a hole injecting layer, a hole transporting layer, and a light emitting layer, and is preferably a light emitting layer. At this time, the compound represented by Formula 1 is a blue, green or red phosphorescent host material.

The novel compounds represented by the formula (1) of the present invention are excellent in thermal stability and phosphorescence properties and thus 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.

<Novel compound>

The present invention has a higher molecular weight than a conventional organic EL device material (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')), and has a wide energy bandgap while enhancing the bonding force between holes and electrons The compound represented by the above formula (1).

According to the present invention, the novel compound represented by Formula 1 has indole fused to a carbazole basic skeleton, and its energy level is controlled by various substituents. Thus, a broad band gap (sky blue ~ red). When such a compound is used in an organic EL device, the phosphorescent property of the device can be improved and the hole injecting ability and / or transporting ability, efficiency (luminous efficiency, power efficiency), driving voltage, lifetime characteristics, . Therefore, the present invention can be applied not only to a light emitting layer but also to a hole transporting layer, a hole injecting layer, etc. due to the introduction of various substituents. Particularly, since the compound has a wide band gap and can increase the bonding force between holes and electrons due to the structural specificity that the indole group is fused to the carbazole basic skeleton, the compound exhibits excellent characteristics as a host material of the light emitting layer compared to CBP .

In addition, since the molecular weight of the compound is significantly increased due to various aromatic ring substituents introduced into the carbazole basic skeleton in which the indole group is fused, the glass transition temperature is improved and the thermal stability Lt; / RTI &gt;

In addition, the novel compound of the present invention is improved in the thermal stability of the compound by fusing cyclohexyl inside the carbazole ring, and is also effective in stability and inhibition of crystallization of the organic film containing the compound. Therefore, the organic EL device comprising the compound of 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, a blue, green, and / or red phosphorescent host material of an organic EL device, have. Therefore, the compound according to the present invention can greatly contribute to improvement of the performance and lifetime of the organic EL device, and in particular, the lifetime improvement of such a device has a great effect on maximizing the performance in the full-color organic light emitting panel.

In the compound represented by the general formula (1) according to the present invention, the substituent forming the condensation ring with the general formula (2), for example, R ₆ and R ₇ and / or R ₁ to R ₁₂ excluding R ₇ and R ₈ are the same Substituted or unsubstituted C ₁ to C ₄₀ alkyl, substituted or unsubstituted C ₂ to C ₄₀ alkenyl, substituted or unsubstituted C &lt; RTI ID = 0.0 &gt; of ₂ ~ C ₄₀ alkynyl group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus atom to C40 heterocycloalkyl group, a substituted or unsubstituted C ₆ ~ C ₆₀ of the aryl A substituted or unsubstituted C ₁ -C ₄₀ alkyloxy group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, the unsubstituted C ₃ ~ C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl silyl group, a substituted addition Unsubstituted C ₂ ~ C ₄₀ alkyl boron group, a substituted or unsubstituted C with ₆ ~ C ₆₀ aryl boron group, an aryl phosphonic a substituted or unsubstituted C ₆ ~ C ₆₀ ring pingi of, substituted or unsubstituted C ₆ of ~ C ₆₀ aryl phosphine oxide group is selected from the pin, and the group consisting of a substituted or unsubstituted C ₆ ~ C ₆₀ aryl amine, these are combined tile adjacent to form a condensed ring.

Here, R ₁ to R ₁₂ , excluding R ₆ and R ₇ and / or R ₇ and R ₈ , represent hydrogen, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted five to twenty- Lt; RTI ID = 0.0 &gt; of-60 &lt; / RTI &gt;

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

In general formula [2] according to the present invention, X is O, S, Se, N ( Ar 2), C (Ar 3) (Ar 4), Si (Ar 5) (Ar 6), P (Ar 7) and B ( Ar ₈ ), preferably O, S, N (Ar ₂ ), C (Ar ₃ ) (Ar ₄ ), and more preferably N (Ar ₂ ).

In the general formula (2), Ar ₁ to Ar ₈ are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, nitro, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ of the alkynyl group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus of atoms of 3 to 40 hetero A substituted or unsubstituted C ₁ to C ₆₀ alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, An unsubstituted C ₆ to C ₆₀ aryloxy group, a substituted or unsubstituted C ₃ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₆ to C ₆₀ arylsilyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkyl boron group, an aryl phosphonic a substituted or unsubstituted C ₆ ~ C ₆₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₆₀ of pingi, A substituted or unsubstituted C ₆ to C ₆₀ arylphosphine oxide group, and a substituted or unsubstituted C ₆ to C ₆₀ arylamine group.

In this case, considering the wide band gap and thermal stability, Ar ₁ is preferably a substituted or unsubstituted C ₆ to C ₆₀ aryl group, or a substituted or unsubstituted heteroaryl group having 5 to 60 nucleus atoms. Ar ₂ to Ar _{8 each} represent a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms desirable.

In the compounds represented by formula (1) of the present invention, X is N (Ar ₂ ), Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C ₆ to C ₄₀ aryl group, and a substituted or unsubstituted nucleus And a heteroaryl group having 5 to 40 atoms. The C ₆ -C ₄₀ aryl group and the heteroaryl group having 5 to 40 nuclear atoms are each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alk 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 ₆ to C ₄₀ arylsilyl group , C of ₂ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ of the An arylamine group, and the like. When a plurality of substituents are introduced, these substituents may be the same as or different from each other.

R ₁ to R ₁₂ and Ar ₁ to Ar _{8, which} are substituents of the compound of formula (1) according to the present invention, are each independently selected from hydrogen or the following substituent (functional group), for example, from S1 to S192, More preferably, R ₁ to R ₁₂ , Ar ₁ and Ar ₂ are selected from hydrogen or the following substituent group (S1 to S192). However, it is not limited thereto. However, in the above-defined R ₁ to R ₁₂ , the substituent forming the condensation ring with the formula (2), for example, R ₆ and R ₇ and / or R ₇ and R ₈ are excluded.

The compound represented by the formula (1) of the present invention may be further represented by a compound represented by the following formula (3) to (6).

In the above Chemical Formulas 3 to 6,

X, R ₁ to R ₁₂ , and Ar ₁ to Ar ₈ are each the same as defined in formula (1).

Specific examples of the compounds represented by the formulas (3) to (6) include compounds represented by the following formulas.

In the illustrated formulas, Ar ₁ to Ar ₈ and R ₁ to R ₁₂ are each the same as defined in formula (1).

In the above formula, when X is N (Ar ₂ ), Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted C ₆ -C ₄₀ aryl group, and a substituted or unsubstituted A heteroaryl group having 5 to 40 nuclear atoms,

R ₁ to R ₁₂ are the same as or different from each other, and are each independently selected from the group consisting of hydrogen or a substituent group composed of S 1 to S 192, more preferably selected from the group consisting of hydrogen and the substituents exemplified below.

When X is C (Ar ₃ ) (Ar ₄ ), Si (Ar ₅ ) (Ar ₆ ), P (Ar ₇ ) or B (Ar ₈ ), Ar ₃ to Ar ₈ are the same or the same It is preferably independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group and a substituted or unsubstituted C ₆ to C ₆₀ aryl group, more preferably a methyl group or a phenyl group. Here, R ₁ to R ₁₂ are the same as or different from each other, and are each independently selected from the group consisting of hydrogen or a substituent group composed of S 1 to S 192, and more preferably hydrogen or a substituent group exemplified below.

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 condensed form. 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. Two or more rings may be attached in a pendant or condensed 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 &gt; 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.

"Condensation ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

The compounds of general formula (I) of the present invention can be synthesized according to the general synthetic method (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.

&Lt; Organic electroluminescent device &

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising the compound represented by Formula 1 according to the present invention.

Specifically, the organic electroluminescent device according to the present invention includes at least one anode, an anode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers Includes any one or more of the compounds represented by the above-mentioned general formula (1), preferably the compounds represented by the general formulas (3) to (6). At this time, the compounds represented by the formulas (3) to (6) may be used singly or in combination of two or more.

Here, 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 may preferably be a hole injecting / transporting layer, a light emitting layer or an electron transporting layer, Emitting 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 compound represented by Formula 1 may be included in an organic light emitting device as a blue, green, and / or red phosphorescent host, a fluorescent host, or a dopant material.

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 . At this time, the compound of the present invention can be used as a phosphorescent host of the 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 is known in the art except that the one or more organic layers (for example, a light emitting layer, a hole transporting layer and / or an electron transporting layer) include a compound represented by Formula 1 Can be produced by forming other organic material layers and electrodes using the materials and methods.

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.

Non-limiting examples of usable cathode materials include metals such as vanadium, chromium, copper, zinc, 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.

Non-limiting examples of usable cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; And multi-layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

The hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer are not particularly limited, and conventional materials known in the art can be used.

Hereinafter, the present invention will be described in detail with reference to Preparation Examples and Synthesis Examples. However, the following Preparative Examples and Synthesis Examples are merely illustrative of the present invention, and the present invention is not limited by the following Preparation Examples and Synthesis Examples.

[Preparation Example 1] Synthesis of IC-1 and IC-2

<Step 1> Synthesis of 4-bromo-6-phenyl-2,6-dihydro-1H-benzo [def] carbazole

(3.38 g, 12.40 mmol), 1-bromobenzene (2.14 g, 37.18 mmol), Cu powder (0.15 g, 2.48 mmol), K ₂ CO ₃ (3.42 g, 24.79 mmol), Na ₂ SO ₄ (3.53 g, 24.79 mmol) and nitrobenzene (100 ml) were mixed and 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 water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the target compound, 4-bromo-6-phenyl-2,6-dihydro-1H-benzo [def] carbazole (3.06 g, 8.80 mmol, yield 71%).

^{1 H-NMR: δ 2.83 (} m, 4H), 7.03 (m, 2H), 7.31 (m, 2H), 7.53 (m, 4H), 7.76 (d, 1H)

<Step 2> Synthesis of 4- (2-nitrophenyl) -6-phenyl-2,6-dihydro-1H-benzo [

2-nitrophenylboronic acid, 1.06 g (26.37 mmol) of 4-bromo-6-phenyl-2,6-dihydro-1H- Of NaOH and 100 ml / 50 ml of THF / H ₂ O were added and stirred. 0.51 g (5 mol%) of Pd (PPh ₃ ) ₄ was added at 40 ° C, 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 the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, the desired compound, 4- (2-nitrophenyl) -6-phenyl-2,6-dihydro-1H-benzo [def] carbazole (2.82 g, 7.22 mmol, yield 82%).

^{1 H-NMR: δ 2.84 (} m, 4H), 7.01 (d, 1H), 7.33 (t, 1H), 7.59 (m, 7H), 7.99 (m, 3H)

<Step 3> Synthesis of IC-1 and IC-2

A mixture of 2.82 g (7.22 mmol) of 4- (2-nitrophenyl) -6-phenyl-2,6-dihydro-1H-benzo [def] carbazole, 4.73 g (18.05 mmol) of triphenylphosphine and 30 ml of 1,2-dichlorobenzene And the mixture was stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed and extracted with dichloromethane. The extracted organic layer was washed with MgSO ₄ and purified by column chromatography to obtain IC-1 (0.99 g, 2.75 mmol, yield 38%) and IC-2 (0.97 g, 2.74 mmol, yield 37% Respectively.

^IC-1 1 H-NMR of: δ 2.83 (m, 4H) , 7.00 (d, 1H), 7.30 (m, 2H), 7.54 (m, 8H), 7.76 (d, 1H), 8.12 (d, 1H ), 10.01 (s, 1 H)

¹ of IC-2 H-NMR: δ 2.84 (m, 4H), 7.00 (d, 1H), 7.28 (m, 3H), 7.56 (m, 7H), 7.77 (d, 1H), 8.12 (d, 1H ), 10.21 (s, 1 H)

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

Synthesis of 6- (biphenyl-4-yl) -4-bromo-2,6-dihydro-1H-benzo [def] carbazole

(Biphenyl-4-yl) -4-bromo (4-bromo-4-methoxyphenyl) propanoate was obtained by following the same procedure as <Step 1> of Preparation Example 1 except that 4-bromobiphenyl (8.67 g, 37.18 mmol) -2,6-dihydro-1H-benzo [def] carbazole.

^{1 H-NMR: δ 2.84 (} m, 4H), 7.01 (m, 2H), 7.31 (m, 2H), 7.64 (m, 7H), 7.79 (m, 3H)

Synthesis of 6- (biphenyl-4-yl) -4- (2-nitrophenyl) -2,6-dihydro-1H-benzo [def] carbazole

(Biphenyl-4-yl) -4-bromo-2,6-dihydro-1H-benzo [f] carbazole instead of 4-bromo-6-phenyl-2,6- dihydro- 4-yl) -4- (2-nitrophenyl) -2,6-dihydroxybenzoic acid was prepared by following the procedure of Step 2 of Preparation Example 1, -dihydro-1H-benzo [def] carbazole.

^{1 H-NMR: δ 2.85 (} m, 4H), 7.01 (d, 1H), 7.28 (t, 1H), 7.51 (m, 6H), 7.69 (m, 7H), 7.98 (m, 3H)

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

6- (biphenyl-4-yl) -4- (2-nitrophenyl) -2,6-dihydro-1H-benzo [ The procedure of Step 3 of Preparation Example 1 was repeated to obtain the desired compounds IC-3 and IC-4, respectively, except that 1H-benzo [def] carbazole (3.27 g, 7.22 mmol) was used.

IC-3 ¹ H-NMR of: δ 2.83 (m, 4H) , 6.91 (d, 1H), 7.28 (m, 2H), 7.49 (m, 7H), 7.66 (m, 6H), 8.11 (d, 1H ), 10.07 (s, 1 H)

IC-4 ¹ H-NMR of: δ 2.83 (m, 4H) , 6.90 (d, 1H), 7.29 (m, 3H), 7.52 (m, 6H), 7.67 (m, 6H), 8.11 (d, 1H ), 10.22 (s, 1 H)

[Preparation Example 3] Synthesis of IC-5 and IC-6

Synthesis of 6- (biphenyl-3-yl) -4-bromo-2,6-dihydro-1H-benzo [def] carbazole

(Biphenyl-3-yl) -4-bromo (4-bromo-2-methylpyridin-2-ylamine) was obtained by following the same procedure as in <Step 1> of Preparation Example 1 except that 3-bromobiphenyl (8.67 g, 37.18 mmol) -2,6-dihydro-1H-benzo [def] carbazole.

^{1 H-NMR: δ 2.84 (} m, 4H), 6.97 (m, 2H), 7.28 (m, 2H), 7.48 (m, 8H), 7.76 (d, 1H), 8.01 (s, 1H)

Synthesis of 6- (biphenyl-3-yl) -4- (2-nitrophenyl) -2,6-dihydro-1H-benzo [def] carbazole

(Biphenyl-3-yl) -4-bromo-2,6-dihydro-1H-benzo [f] carbazole instead of 4-bromo-6-phenyl-2,6- dihydro- 3-yl) -4- (2-nitrophenyl) -2,6-dihydroquinolinecarboxamide was prepared by following the procedure of Step 2 of Preparation Example 1, -dihydro-1H-benzo [def] carbazole.

^{1 H-NMR: δ 2.83 (} m, 4H), 6.95 (d, 1H), 7.28 (t, 1H), 7.51 (m, 10H), 7.73 (m, 2H), 8.02 (m, 3H)

<Step 3> Synthesis of IC-5 and IC-6

6- (biphenyl-3-yl) -4- (2-nitrophenyl) -2,6-dihydro-1H- benzo [ The procedure of Step 3 of Preparation Example 1 was repeated to obtain the desired compounds IC-5 and IC-6, respectively, except that 1H-benzo [def] carbazole (3.3 g, 7.22 mmol) was used.

The ^{IC-5 1 H-NMR:} δ 2.83 (m, 4H), 6.87 (d, 1H), 7.28 (m, 2H), 7.50 (m, 11H), 7.78 (d, 1H), 8.05 (m, 2H ), 10.01 (s, 1 H)

IC-6 ¹ H-NMR of: δ 2.83 (m, 4H) , 6.87 (d, 1H), 7.27 (m, 3H), 7.51 (m, 10H), 7.78 (d, 1H), 8.04 (m, 2H ), 10.12 (s, 1 H)

[Preparation Example 4] Synthesis of IC-7

Synthesis of tert-butyl 4-bromo-1H-benzo [def] carbazole-6 (2H) -carboxylate

4-Dimethylaminopyridine (7.35 g, 60.1 mmol) was added to a solution of 4-bromo-2,6-dihydro-1H-benzo [ 300 ml, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, water was poured, the organic layer was separated with methylene chloride, and then water was removed using MgSO ₄ . Tert-butyl 4-bromo-1H-benzo [def] carbazole-6 (2H) -carboxylate (20.55 g, 55.2 mmol, yield 92%) was obtained by purifying the target compound by removing the solvent of the organic layer.

^{1 H-NMR: δ 1.59 (} s, 9H), 2.85 (m, 4H), 7.03 (d, 1H), 7.27 (m, 3H), 7.51 (d, 1H)

<Step 2> Synthesis of tert-butyl 4- (2-nitrophenyl) -1H-benzo [def] carbazole-6 (2H) -carboxylate

(2-nitrophenyl) -lH-benzo [b] carbazole-6 (2H) -carboxylate (3.28 g, 9.2 mmol) instead of 4-bromo-6-phenyl-2,6- dihydro- (2-nitrophenyl) -lH-benzo [def] carbazole-6 (2H) was obtained in the same manner as Step 2 of Preparation Example 1, -carboxylate.

¹ H-NMR:? 1.59 (s, 9H), 2.85 (m, 4H), 7.28 (m, 2H), 7.51

<Step 3> Synthesis of IC-7-1 and IC-10-1

(2-nitrophenyl) -1H-benzo [f] carbazole-6 (2H) - (2-nitrophenyl) -6- carboxylate (2.99 g, 7.22 mmol) was used in place of the compound obtained in Preparation Example 1 to obtain the desired compounds IC-7-1 and IC-10-1.

¹ H-NMR of the IC-7-1: δ 1.60 (s , 9H), 2.84 (m, 4H), 7.29 (m, 3H), 7.50 (m, 3H), 7.61 (d, 1H), 8.03 (d , 1 H), 10.04 (s, 1 H)

The ^{IC-10-1 1 H-NMR:} δ 1.60 (s, 9H), 2.83 (m, 4H), 7.27 (m, 3H), 7.51 (m, 3H), 7.61 (d, 1H), 8.04 (d , &Lt; / RTI &gt; 1H), 10.13 (s, 1H)

<Step 3> Synthesis of IC-7

(2.14 g, 37.18 mmol), Cu powder (0.15 g, 2.48 mmol), K ₂ CO ₃ (3.42 g, 24.79 mmol), Na ₂ SO ₄ (3.53 g, 24.79 mmol) and nitrobenzene (100 ml) were mixed and 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 water was removed using MgSO ₄ . After removing the solvent of the organic layer, the organic compound was added to 2000 ml of toluene together with 500 g of Silica-gel, stirred at 110 ° C for 12 hours, and silica-gel was removed by filtration. (2.80 g, 7.81 mmol, yield 63%).

¹ H-NMR:? 2.84 (m, 4H), 7.33 (m, 4H), 7.52 (m, 6H), 7.91 (d, s, 1 H)

[Preparation Example 5] Synthesis of IC-8

<Step 1> Synthesis of IC-8

IC-8 was obtained in the same manner as in <Step 3> of Preparation Example 4 except that 4-bromobiphenyl (8.67 g, 37.18 mmol) was used instead of 1-bromobenzene.

^{1 H-NMR: δ 2.85 (} m, 4H), 7.35 (m, 4H), 7.48 (m, 6H), 7.69 (m, 4H), 7.96 (m, 2H), 8.53 (d, 1H), 10.04 ( s, 1 H)

[Preparation Example 6] Synthesis of IC-9

<Step 1> Synthesis of IC-9

IC-9 was obtained in the same manner as in <Step 3> of Preparation Example 4 except that 3-bromobiphenyl (8.67 g, 37.18 mmol) was used instead of 1-bromobenzene.

^{1 H-NMR: δ 2.85 (} m, 4H), 7.33 (m, 4H), 7.42 (m, 5H), 7.67 (m, 5H), 7.92 (m, 2H), 8.53 (d, 1H), 10.04 ( s, 1 H)

[Preparation Example 7] Synthesis of IC-10

<Step 1> IC Synthesis of -10

IC-10 was obtained in the same manner as in <Step 3> of Preparation Example 4 except that IC-10-1 (4.74 g, 12.40 mmol) was used instead of IC-7-1.

¹ H-NMR:? 2.83 (m, 4H), 7.31 (m, 4H), 7.51 (m, 8H), 7.92

[Preparation Example 8] Synthesis of IC-11

<Step 1> Synthesis of IC-11

IC-11 was obtained in the same manner as in <Step 1> of Preparation Example 5 except that IC-10-1 (4.74 g, 12.40 mmol) was used instead of IC-7-1.

¹ H-NMR:? 2.84 (m, 4H), 7.32 (m, 4H), 7.51 (m, 7H)

[Preparation Example 9] Synthesis of IC-12

<Step 1> IC Synthesis of -12

IC-12 was obtained in the same manner as in <Step 1> of Preparation Example 6 except that IC-10-1 (4.74 g, 12.40 mmol) was used instead of IC-7-1.

¹ H-NMR:? 2.84 (m, 4H), 7.35 (m, 4H), 7.54 (m, 6H), 7.79

[Preparation Example 10] Synthesis of IC-13 and IC-14

Synthesis of 4,8-dibromo-6-phenyl-2,6-dihydro-1H-benzo [def] carbazole

Except that 4,8-dibromo-2,6-dihydro-1H-benzo [def] carbazole (4.35 g, 12.40 mmol) was used instead of 4-bromo-2,6-dihydro-1H- 4-dibromo-6-phenyl-2,6-dihydro-1H-benzo [def] carbazole was obtained in the same manner as in <Step 1> of Preparation Example 1 above.

^{1 H-NMR: δ 2.84 (} m, 4H), 7.03 (s, 2H), 7.39 (s, 2H), 7.49 (m, 5H)

<Step 2> Synthesis of 4-bromo-6,8-diphenyl-2,6-dihydro-1H-benzo [def] carbazole

4-bromo-6-phenyl-2,6-dihydro-1H-benzo [def] carbazole (3.76 g, 8.80 mmol) instead of 4-bromo- Step 2 of Preparation Example 1 was repeated except that phenylboronic acid (3.22 g, 26.37 mmol) was used in place of 2-nitrophenylboronic acid to give 4-bromo-6,8 -diphenyl-2,6-dihydro-1H-benzo [def] carbazole.

^{1 H-NMR: δ 2.84 (} m, 4H), 7.08 (m, 2H), 7.39 (m, 4H), 7.53 (m, 8H)

<Step 3> 4- (2-nitrophenyl) -6,8-diphenyl-2,6-dihydro-1H-benzo [def] carbazole Synthesis of

4-bromo-6,8-diphenyl-2,6-dihydro-1H-benzo [def] carbazole (3.73 g, 8.80 mmol) instead of 4-bromo-6-phenyl-2,6- dihydro- 2-nitrophenyl) -6,8-diphenyl-2,6-dihydro-1H-benzo [def ] carbazole.

¹ H-NMR:? 2.89 (m, 4H), 7.41 (m, 4H), 7.53

<Step 4> Synthesis of IC-13 and IC-14

Substituting 4- (2-nitrophenyl) -6,8-diphenyl-2,6-dihydro-1H-benzo [b] for 4- (2-nitrophenyl) -6- def] carbazole (3.37 g, 7.22 mmol) was used in place of the compound [IC-13]. IC-13 and IC-14 were obtained in the same manner as in <Step 3> of Preparation Example 1 above.

¹ H-NMR:? 2.87 (m, 4H), 7.42 (m, 6H), 7.54

¹ H-NMR:? 2.87 (m, 4H), 7.43 (m, 5H), 7.57 (m, 9H)

[Preparation Example 11] Synthesis of IC-15

Synthesis of tert-butyl 4- (2- (chloromethyl) phenyl) -lH-benzo [def] carbazole-6 (2H) -carboxylate

Step 2 of Preparation Example 4 was repeated except that 2- (chloromethyl) phenylboronic acid (1.50 g, 8.80 mmol) was used instead of 2-nitrophenylboronic acid to obtain tert-butyl 4- (2- (chloromethyl) phenyl) -1H-benzo [def] carbazole-6 (2H) -carboxylate.

^{1 H-NMR: δ 1.59 (} s, 9H), 2.84 (m, 4H), 4.53 (s, 2H), 7.18 (m, 2H), 7.42 (m, 2H), 7.55 (m, 2H), 7.74 ( m, 3H)

Step 2: Preparation of tert-butyl 4,5-dihydrobenzo [def] indeno [2,1-a] carbazole-12 (11H) ] carbazole-6 (12H) -carboxylate

(2H) -carboxylate (8.36 g, 20.00 mmol) and Pd (OAc) ₂ (0.23 g, 1.00 mmol) in a nitrogen atmosphere. ), 2- (di-tert-butylphosphino) biphenyl ligand (JohnPhos, 0.60 g, 2.00 mmol), TEA (5.6 ml, 40.00 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C for 12 hours.

After the reaction was completed, the toluene was removed, the organic layer was separated with methylene chloride, and then the water was removed using MgSO ₄ . After removal of the organic layer solvent, the residue was purified by column chromatography to obtain tert-butyl 4,5-dihydrobenzo [def] indeno [2,1-a] carbazole-12 (11H) -carboxylate (2.06 g, 5.40 mmol, 27%) and tert-butyl 1,2-dihydrobenzo [def] indeno [1,2-b] carbazole-6 (12H) -carboxylate (2.21 g, 5.80 mmol, yield 29%).

¹ H-NMR:? 1.59 (s, 9H), 2.83 (m, 4H), 4.11 (m, 4H) 1H), 7.74 (m, 2H), 7.98 (m, 3H), 7.42

¹ H-NMR:? 1.59 (s, 9H), 2.83 (m, 4H), 4.11 (m, 4H) (s, 2H), 7.22 (m, 3H), 7.44 (m,

<Step 3> Synthesis of IC-15

(11H) -carboxylate (2.06 g, 5.40 mmol) was dissolved in 50 ml of THF at 0 ° C., and a solution of potassium tert-butyl 4,5-dihydrobenzo [ butoxide (1.81 g, 16.13 mmol) was added thereto, followed by stirring for 10 minutes. Iodomethane (2.29 g, 16.13 mmol) was added thereto, followed by stirring at room temperature for 12 hours.

After the reaction was completed, the THF was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the organic compound was added to 200 ml of toluene together with 150 g of silica gel, stirred at 110 ° C. for 12 hours, filtered to remove silica-gel, 1.02 g, 3.29 mmol, yield: 61%).

^{1 H-NMR: δ 1.57 (} s, 6H), 2.83 (m, 4H), 7.23 (m, 3H), 7.55 (m, 2H), 7.75 (m, 2H), 7.91 (d, 1H), 10.13 ( s, 1 H)

[Preparation Example 12] Synthesis of IC-16

<Step 1> Synthesis of IC-16

tert-butyl 4,5-dihydrobenzo [b] indeno [2,1-a] carbazole-12 (11H) (1.08 g, 3.51 mmol, yield 65%) was obtained by carrying out the same procedure as <Step 3> of Preparation Example 11, except that the compound (12H) -carboxylate (2.06 g, 5.40 mmol) .

^{1 H-NMR: δ 1.57 (} s, 6H), 2.83 (m, 4H), 7.24 (m, 3H), 7.51 (m, 2H), 7.72 (m, 2H), 7.93 (d, 1H), 10.08 ( s, 1 H)

[Synthesis Example 1] Synthesis of Inv-1

(1.07 g, 3.00 mmol), 2-bromo-6-phenylpyridine (0.84 g, 3.60 mmol), Cu powder (0.027 g, 0.40 mmol), K ₂ CO ₃ (0.55 g, 0.40 mmol), Na ₂ SO ₄ (0.57 g, 4.00 mmol) and nitrobenzene (100 ml) were mixed and 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 water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain the target compound Inv-1 (1.23 g, yield 80%).

GC-Mass (calculated: 511.61 g / mol, measured: 511 g / mol)

[Synthesis Example 2] Synthesis of Inv-2

Compound IC-1 (1.07 g, 3.00 mmol) prepared in Preparation Example 1 was dissolved in DMF (100 ml) under a nitrogen stream, and NaH (0.11 g, 4.50 mmol) was added thereto and stirred for 1 hour. 2-chloro-4,6-diphenyl-1,3,5-triazine (0.96 g, 3.60 mmol) dissolved in 100 ml of DMF was added slowly. After stirring for 3 hours, the reaction was terminated and the mixture was filtered through silica, washed with water and methanol, and then the solvent was removed. The solvent-removed solid was purified by column chromatography (Hexane: EA = 1: 1 (v / v)) to give the target compound Inv-2 (1.38 g, yield 78%).

GC-Mass (calculated: 589.23 g / mol, measured: 589 g / mol)

[Synthesis Example 3] Synthesis of Inv-3

Synthesis was conducted in the same manner as in Synthesis Example 1, except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine was used instead of 2-bromo-6- -3 (1.50 g, yield 75%).

GC-Mass (calculated: 665.26 g / mol, measured: 665 g / mol)

[Synthesis Example 4] Synthesis of Inv-4

(1.65 g, yield 78%) was obtained in the same manner as in Synthesis Example 1 except that 2- (4-bromophenyl) triphenylene was used in place of 2-bromo-6-phenylpyridine.

GC-Mass (calculated: 660.26 g / mol, measured: 660 g / mol)

[Synthesis Example 5] Synthesis of Inv-5

Inv-5 (1.37 g, yield 76%) was synthesized in the same manner as in Synthesis Example 1, except that 3-bromo-9-phenyl-9H-carbazole was used in place of 2-bromo- .

GC-Mass (calculated: 599.24 g / mol, measured: 599 g / mol)

[Synthesis Example 6] Synthesis of Inv-6

(1.22 g, yield 75%) as a target compound was obtained by the same method as in Synthesis Example 1, except that 4-bromodibenzo [b, d] thiophene was used in place of 2-bromo-6-phenylpyridine .

GC-Mass (calculated: 540.17 g / mol, measured: 540 g / mol)

[Synthesis Example 7] Synthesis of Inv-7

2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 2- (3-bromophenyl) -4,6-diphenylpyrimidine Inv-7 (1.53 g, yield 78%).

GC-Mass (theory: 664.28 g / mol, measurement: 664 g / mol)

[Synthesis Example 8] Synthesis of Inv-8

Except that IC-2 and 2-chloro-4,6-diphenylpyrimidine were used in place of IC-1 and 2-chloro-4,6-diphenyl-1,3,5- To obtain the target compound Inv-8 (1.25 g, yield 71%).

GC-Mass (calculated: 588.23 g / mol, measured: 588 g / mol)

[Synthesis Example 9] Synthesis of Inv-9

Synthesis Example 1 was repeated except that IC-2 and 2-bromo-4,6-diphenylpyridine were used in place of IC-1 and 2-bromo-6-phenylpyridine, g, yield: 80%).

GC-Mass (calculated: 587.24 g / mol, measured: 587 g / mol)

[Synthesis Example 10] Synthesis of Inv-10

Synthesis Example 3 was repeated except that IC-2 was used instead of IC-1 to obtain the target compound Inv-10 (1.50 g, yield 75%).

GC-Mass (calculated: 665.26 g / mol, measured: 665 g / mol)

[Synthesis Example 11] Synthesis of Inv-11

Except that IC-2 and 2- (3-bromo-5-methylphenyl) -4,6-diphenyl-1,3,5-triazine were used instead of IC-1 and 2-bromo-6-phenylpyridine, respectively. Was synthesized in the same manner as in Synthesis Example 1 to obtain Inv-11 (1.61 g, yield 79%) as a target compound.

GC-Mass (calculated: 679.27 g / mol, measured: 679 g / mol)

[Synthesis Example 12] Synthesis of Inv-12

Except that IC-2 and 2- (3-bromo-5- (trifluoromethyl) phenyl) -4,6-diphenyl-1,3,5-triazine were used instead of IC-1 and 2-bromo-6- Was synthesized in the same manner as in Synthesis Example 1 to obtain Inv-12 (1.58 g, yield 72%) as a target compound.

GC-Mass (733.25 g / mol, measured: 733 g / mol)

[Synthesis Example 13] Synthesis of Inv-13

Synthesis was conducted in the same manner as in Synthesis Example 1, except that IC-3 was used instead of IC-1 to obtain the target compound Inv-13 (1.32 g, yield 75%).

GC-Mass (calculated: 587.24 g / mol, measured: 587 g / mol)

[Synthesis Example 14] Synthesis of Inv-14

Synthesis Example 2 was repeated except that IC-3 was used instead of IC-1 to obtain Inv-14 (1.50 g, yield 75%) as a target compound.

GC-Mass (calculated: 665.26 g / mol, measured: 665 g / mol)

[Synthesis Example 15] Synthesis of Inv-15

Was synthesized in the same manner as in Synthesis Example 3, except that IC-3 was used in place of IC-1 to obtain the target compound Inv-15 (1.69 g, yield 76%).

GC-Mass (741.29 g / mol, measured: 741 g / mol)

[Synthesis Example 16] Synthesis of Inv-16

(1.57 g, yield 71%) was obtained by the same method as Synthesis Example 7, except that IC-3 was used instead of IC-1.

GC-Mass (calculated: 740.29 g / mol, measured: 740 g / mol)

[Synthesis Example 17] Synthesis of Inv-17

Synthesis Example 3 was repeated except that IC-4 was used instead of IC-1 to obtain the target compound Inv-17 (1.45 g, yield 75%).

GC-Mass (calculated: 643.27 g / mol, measured: 643 g / mol)

[Synthesis Example 18] Synthesis of Inv-18

Was synthesized in the same manner as in Synthesis Example 11, except that IC-4 was used in place of IC-2 to obtain the target compound Inv-18 (1.65 g, yield 73%).

GC-Mass (calculated: 755.30 g / mol, measured: 755 g / mol)

[Synthesis Example 19] Synthesis of Inv-19

Except that IC-4 and 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine were used in place of IC-1 and 2-bromo-6-phenylpyridine, respectively. (Inv-19, 1.84 g, yield 75%) was obtained by synthesizing the same method as Synthesis Example 1.

GC-Mass (theory: 817.32 g / mol, measured: 817 g / mol)

[Synthesis Example 20] Synthesis of Inv-20

(Inv-20) (1.37 g, yield 78%) was obtained in the same manner as in Synthesis Example 1, except that IC-5 was used instead of IC-1.

GC-Mass (calculated: 587.24 g / mol, measured: 587 g / mol)

[Synthesis Example 21] Synthesis of Inv-21

Was synthesized in the same manner as in Synthesis Example 2, except that IC-5 was used in place of IC-1 to obtain the target compound Inv-21 (1.50 g, yield 75%).

GC-Mass (calculated: 665.26 g / mol, measured: 665 g / mol)

[Synthesis Example 22] Synthesis of Inv-22

Synthesis Example 3 was repeated except that IC-5 was used instead of IC-1 to obtain Inv-22 (1.78 g, yield 80%) as a target compound.

GC-Mass (741.29 g / mol, measured: 741 g / mol)

[Synthesis Example 23] Synthesis of Inv-23

Was synthesized in the same manner as in Synthesis Example 7, except that IC-5 was used instead of IC-1 to obtain the target compound Inv-23 (1.64 g, yield 74%).

GC-Mass (calculated: 740.29 g / mol, measured: 740 g / mol)

[Synthesis Example 24] Synthesis of Inv-24

Synthesis Example 3 was repeated except that IC-6 was used in place of IC-1 to obtain the target compound Inv-24 (1.50 g, yield 78%).

GC-Mass (calculated: 643.27 g / mol, measured: 643 g / mol)

[Synthesis Example 25] Synthesis of Inv-25

Synthesis was carried out in the same manner as in Synthesis Example 11, except that IC-6 was used instead of IC-2 to obtain the object compound Inv-25 (1.65 g, yield 73%).

GC-Mass (calculated: 755.30 g / mol, measured: 755 g / mol)

[Synthesis Example 26] Synthesis of Inv-26

Except that IC-6 and 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine were used instead of IC-1 and 2-bromo-6-phenylpyridine, respectively. Synthesis was conducted in the same manner as in Synthesis Example 1 to obtain Inv-26 (1.74 g, yield 71%) as a target compound.

GC-Mass (theory: 817.32 g / mol, measured: 817 g / mol)

[Synthesis Example 27] Synthesis of Inv-27

Except that IC-7 and 3-bromo-9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazole were used in place of IC-1 and 2-bromo-6- Was synthesized in the same manner as in Synthesis Example 1 to obtain Inv-27 (1.65 g, yield 73%) as a target compound.

GC-Mass (calculated: 754.28 g / mol, measured: 754 g / mol)

[Synthesis Example 28] Synthesis of Inv-28

Except that IC-7 and (4-bromophenyl) diphenylborane were used in place of IC-1 and 2-bromo-6-phenylpyridine, respectively, to obtain the target compound Inv-28 (1.43 g, Yield: 80%).

GC-Mass (theory: 598.26 g / mol, measured: 598 g / mol)

[Synthesis Example 29] Synthesis of Inv-29

29 (1.41 g, yield) was synthesized in the same manner as in Synthesis Example 1 except that IC-7 and (4-bromophenyl) diphenylphosphine were used in place of IC-1 and 2-bromo- Yield: 76%).

GC-Mass (theory: 618.22 g / mol, measured: 618 g / mol)

[Synthesis Example 30] Synthesis of Inv-30

Synthesis was carried out in the same manner as in Synthesis Example 2 except that IC-7 and (4-chlorophenyl) triphenylsilane were used instead of IC-1 and 2-chloro-4,6-diphenyl-1,3,5- The compound Inv-30 (1.56 g, yield 75%) was obtained.

GC-Mass (calculated: 692.26 g / mol, measured: 692 g / mol)

[Synthesis Example 31] Synthesis of Inv-31

Was synthesized in the same manner as in Synthesis Example 3, except that IC-7 was used instead of IC-1 to obtain the target compound Inv-31 (1.50 g, yield 75%).

GC-Mass (calculated: 665.26 g / mol, measured: 665 g / mol)

[Synthesis Example 32] Synthesis of Inv-32

Synthesis Example 3 was repeated except that IC-10 was used instead of IC-1 to obtain the target compound Inv-32 (1.51 g, yield 76%).

GC-Mass (calculated: 665.28 g / mol, measured: 665 g / mol)

[Synthesis Example 33] Synthesis of Inv-33

Except that IC-10 and 2- (3-bromo-5-methylphenyl) -4,6-diphenyl-1,3,5-triazine were used instead of IC-1 and 2-bromo-6-phenylpyridine, respectively. Was synthesized in the same manner as in Synthesis Example 1 to obtain Inv-33 (1.63 g, yield 80%) as a target compound.

GC-Mass (calculated: 679.27 g / mol, measured: 679 g / mol)

[Synthesis Example 34] Synthesis of Inv-34

Except that IC-10 and 2- (3-bromo-5- (trifluoromethyl) phenyl) -4,6-diphenyl-1,3,5-triazine were used instead of IC-1 and 2-bromo-6- Was synthesized in the same manner as in Synthesis Example 1 to obtain Inv-12 (1.65 g, yield 75%) as a target compound.

GC-Mass (733.25 g / mol, measured: 733 g / mol)

[Synthesis Example 35] Synthesis of Inv-35

Synthesis Example 3 was repeated except that IC-11 was used instead of IC-1 to obtain Inv-35 (1.78 g, yield 80%) as a target compound.

GC-Mass (741.29 g / mol, measured: 741 g / mol)

[Synthesis Example 36] Synthesis of Inv-36

(1.573 g, yield 78%) was obtained in the same manner as in Synthesis Example 7, except that IC-11 was used instead of IC-1.

GC-Mass (calculated: 740.29 g / mol, measured: 740 g / mol)

[Synthesis Example 37] Synthesis of Inv-37

Was synthesized in the same manner as in Synthesis Example 3, except that IC-8 was used instead of IC-1 to obtain the target compound Inv-37 (1.67 g, yield 75%).

GC-Mass (741.29 g / mol, measured: 741 g / mol)

[Synthesis Example 38] Synthesis of Inv-38

Except that IC-8 and 2- (3-bromo-5-methylphenyl) -4,6-diphenyl-1,3,5-triazine were used in place of IC-1 and 2-bromo-6-phenylpyridine, respectively. Synthesis Example 1 was repeated to obtain Inv-38 (1.61 g, yield 71%) as a target compound.

GC-Mass (calculated: 755.30 g / mol, measured: 755 g / mol)

[Synthesis Example 39] Synthesis of Inv-39

Except that IC-4 and 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine were used in place of IC-1 and 2-bromo-6-phenylpyridine, respectively. (Inv-39, 1.84 g, yield 75%) was obtained in the same manner as in Synthesis Example 1.

GC-Mass (theory: 817.32 g / mol, measured: 817 g / mol)

[Synthesis Example 40] Synthesis of Inv-40

Synthesis Example 3 was repeated except that IC-9 was used instead of IC-1 to obtain the target compound Inv-40 (1.67 g, yield 75%).

GC-Mass (741.29 g / mol, measured: 741 g / mol)

[Synthesis Example 41] Synthesis of Inv-41

Synthesis was conducted in the same manner as in Synthesis Example 7, except that IC-9 was used instead of IC-1 to obtain the target compound Inv-41 (1.64 g, yield 74%).

GC-Mass (calculated: 740.29 g / mol, measured: 740 g / mol)

[Synthesis Example 42] Synthesis of Inv-42

Synthesis Example 3 was repeated except that IC-12 was used in place of IC-1 to obtain the target compound Inv-42 (1.78 g, yield 80%).

GC-Mass (741.29 g / mol, measured: 741 g / mol)

[Synthesis Example 43] Synthesis of Inv-43

Synthesis was conducted in the same manner as in Synthesis Example 3, except that IC-13 was used in place of IC-1 to obtain the target compound Inv-43 (1.58 g, yield 71%).

GC-Mass (741.29 g / mol, measured: 741 g / mol)

[Synthesis Example 44] Synthesis of Inv-44

The procedure of Synthesis Example 3 was repeated except that IC-14 was used instead of IC-1 to obtain the target compound Inv-44 (1.76 g, yield 79%).

GC-Mass (741.29 g / mol, measured: 741 g / mol)

[Synthesis Example 45] Synthesis of Inv-45

Synthesis Example 3 was repeated except that IC-15 was used in place of IC-1 to obtain the target compound Inv-45 (1.48 g, yield 80%).

GC-Mass (theory: 616.26 g / mol, measured: 616 g / mol)

[Synthesis Example 46] Synthesis of Inv-46

Synthesis Example 3 was repeated except that IC-16 was used instead of IC-1 to obtain the target compound Inv-46 (1.42 g, yield 77%).

GC-Mass (theory: 616.26 g / mol, measured: 616 g / mol)

[Synthesis Example 47] Synthesis of Inv-47

Synthesis was conducted in the same manner as in Synthesis Example 1, except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine was used instead of 2-bromo-6- -47 (1.58 g, yield 71%).

GC-Mass (741.29 g / mol, measured: 741 g / mol)

[Synthesis Example 48] Synthesis of Inv-48

Synthesis was carried out in the same manner as in Synthesis Example 1, except that 2- (3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine was used instead of 2-bromo-6- To obtain Inv-48 (1.56 g, yield 70%) as a target compound.

GC-Mass (741.29 g / mol, measured: 741 g / mol)

[Synthesis Example 49] Synthesis of Inv-49

Synthesis was carried out in the same manner as in Synthesis Example 1, except that 2- (3'-bromobiphenyl-4-yl) -4,6-diphenyl-1,3,5-triazine was used in place of 2-bromo-6- To obtain the object compound Inv-49 (1.56 g, yield 70%).

GC-Mass (741.29 g / mol, measured: 741 g / mol)

[Synthesis Example 50] Synthesis of Inv-50

Was synthesized in the same manner as in Synthesis Example 1, except that N- (biphenyl-4-yl) -N- (4-bromophenyl) biphenyl-4-amine was used in place of 2-bromo- Inv-50 (1.69 g, yield 75%).

GC-Mass (calculated: 753.31 g / mol, measured: 753 g / mol)

[Example 1] Production of organic EL device

The compound Inv-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 produced as follows.

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

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

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

[Examples 2 to 50] Preparation of organic EL device

Except that the compounds (Inv-2 to Inv-50) synthesized in Synthesis Examples 2 to 50 were used in place of the compound Inv-1 used as a light emitting host material in the formation of the light emitting layer in Example 1, To prepare an organic EL device.

[Comparative Example 1] Fabrication of organic EL device

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

[Experimental Example]

The driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2 were measured for the green organic EL devices manufactured in Examples 1 to 50 and Comparative Example 1, respectively, and the results are shown in the following Table 1 .

Sample Host Driving voltage
(V) Current efficiency
(cd / A) Example 1 Inv-1 6.55 41.5 Example 2 Inv-2 6.49 41.0 Example 3 Inv-3 6.53 41.3 Example 4 Inv-4 6.55 40.9 Example 5 Inv-5 6.50 41.0 Example 6 Inv-6 6.52 41.2 Example 7 Inv-7 6.51 41.5 Example 8 Inv-8 6.44 40.8 Example 9 Inv-9 6.50 41.6 Example 10 Inv-10 6.45 41.3 Example 11 Inv-11 6.58 40.8 Example 12 Inv-12 6.60 41.0 Example 13 Inv-13 6.55 41.2 Example 14 Inv-14 6.50 41.7 Example 15 Inv-15 6.65 42.1 Example 16 Inv-16 6.60 41.5 Example 17 Inv-17 6.62 41.9 Example 18 Inv-18 6.50 41.7 Example 19 Inv-19 6.45 40.5 Example 20 Inv-20 6.52 41.5 Example 21 Inv-21 6.50 40.9 Example 22 Inv-22 6.60 41.5 Example 23 Inv-23 6.45 41.8 Example 24 Inv-24 6.52 40.8 Example 25 Inv-25 6.55 41.2 Example 26 Inv-26 6.58 41.5 Example 27 Inv-27 6.61 42.1 Example 28 Inv-28 6.50 41.6 Example 29 Inv-29 6.55 41.0 Example 30 Inv-30 6.50 41.3 Example 31 Inv-31 6.60 40.8 Example 32 Inv-32 6.55 41.5 Example 33 Inv-33 6.55 41.2 Example 34 Inv-34 6.50 41.7 Example 35 Inv-35 6.65 42.1 Example 36 Inv-36 6.60 41.3 Example 37 Inv-37 6.62 40.9 Example 38 Inv-38 6.50 41.2 Example 39 Inv-39 6.45 40.6 Example 40 Inv-40 6.52 41.0 Example 41 Inv-41 6.50 40.7 Example 42 Inv-42 6.60 41.1 Example 43 Inv-43 6.45 41.0 Example 44 Inv-44 6.52 40.5 Example 45 Inv-45 6.55 40.9 Example 46 Inv-46 6.50 42.0 Example 47 Inv-47 6.51 41.9 Example 48 Inv-48 6.50 41.8 Example 49 Inv-49 6.45 42.1 Example 50 Inv-50 6.45 41.5 Comparative Example 1 CBP 6.93 38.2

As a result of the experiment, the organic EL devices prepared in Examples 1 to 50, respectively using the compounds represented by the formula (1) (compounds Inv-1 to Inv-50) according to the present invention as the host material of the light emitting layer, It was confirmed that the organic EL device of Example 1 exhibited superior performance in current efficiency and driving voltage.

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

Claims (8)

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

In this formula,
R ₆ and R ₇ or R ₇ and R _8, at least one of which is to form the formula (2) with a condensed ring,
(2)

X is selected from the group consisting of N (Ar _2), and _{C (Ar 3) (Ar 4} ),
R ₁ to R ₁₂ are the same or different and each independently hydrogen or phenyl,
Ar ₁ and Ar ₂ are the same or different and each independently represents a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ arylsilyl group, a C ₆ to C _A C ₆ to C ₆₀ arylphosphine group, and a C ₆ to C ₆₀ arylamine group,
Ar ₃ and Ar ₄ are the same or different and are each independently a C ₁ -C ₄₀ alkyl or phenyl group,
The C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₄₀ aryl silyl group, C of of ₆ ~ C ₆₀ aryl phosphine group, and a C ₆ ~ group is an aryl amine of the C _60, each independently of halogen, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, and the number of nuclear atoms of 5 to 40 of the A heteroaryl group, and a heteroaryl group. The compound according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following formulas (3) to (6)
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In this formula,
X, R ₁ to R ₁₂ , and Ar ₁ to Ar ₄ are the same as defined in claim 1, respectively. The compound according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following compounds:

In this formula,
R ₁ to R ₁₂ and Ar ₁ to Ar ₄ are the same as defined in claim 1, respectively. delete delete The method according to claim 1,
Wherein X is N (Ar ₂ ), Ar ₁ to Ar ₂ are the same or different and are each independently selected from the following Substituent group:

A cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the one or more organic layers includes at least one organic layer selected from the group consisting of those described in any one of claims 1 to 3, Wherein the organic compound is a compound represented by the following formula (1). The organic electroluminescent device according to claim 7, wherein at least one organic compound layer containing the compound is selected from the group consisting of a hole injection layer, a hole transport layer and a light emitting layer.