KR20150103968A - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to an organic compound and an organic electroluminescent device comprising the same. The organic compounds in the present invention can enhance light emission efficiency, a driving voltage, and a life span of an organic electroluminescent device by being used in an organic layer, preferably a light emitting layer, of the organic electroluminescent 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 and an organic electroluminescent device including the same.

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. The material contained in the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material, or the like depending on its function.

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

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

Currently, anthracene derivatives are known as fluorescent dopant / host materials used in the light emitting layer. As phosphorescent dopant materials used for the light emitting layer, metal complex compounds including Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like are known. As phosphorescent host materials, 4,4-dicarbazolybiphenyl (CBP) is known.

However, since the conventional materials have low glass transition temperature and thermal stability is poor, the lifetime of the organic electroluminescent device is not satisfactory and the improvement of the luminescent characteristics is still required.

Korea public patent 2011-0066763

In order to solve the above problems, it is an object of the present invention to provide an organic compound having a high glass transition temperature, an excellent thermal stability, and an ability to improve the bonding force between holes and electrons.

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

In order to accomplish the above object, the present invention provides a compound represented by the following general formula (1).

[Chemical Formula 1]

In Formula 1,

Y ₁ to Y ₁₂ are each independently C (R ₁ ) or N, wherein Y ₁ and Y ₂ , Y ₂ and Y ₃ , Y ₃ and Y ₄ , Y ₅ and Y ₆ , Y ₆ and Y ₇ , Y ₇ and Y ₈ , Y ₉ and Y ₁₀ , Y ₁₀ and Y _11, and Y ₁₁ and Y ₁₂ are both C (R ₁ ), and are bonded to each other to form a condensed ring represented by the following formula (2)

(2)

In the formula (2), the dotted line is a moiety bonded to the formula (1)

In the above Formulas 1 and 2,

X ₁ and X ₂ are each independently selected from the group consisting of N (Ar ₁ ), O, S, C (Ar ₂ ) (Ar ₃ ) and Si (Ar ₄ ) (Ar ₅ ) N (Ar &_lt; ₁ >),

Y ₁₃ to Y ₁₆ are each independently C (R ₂ ) or N,

Ar ₁ to Ar _{5 each} independently represent a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms A C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic group having 3 to 40 nuclear atoms alkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine of C ₆₀ A pentacene group, a pin oxide group, and an arylsilyl group of C ₆ to C ₆₀ ,

A plurality of R which does not form a condensed ring ₁ and R ₂ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C _A C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkenyl group, C ₆ -C ₆₀ aryloxy groups, C ₁ -C ₄₀ alkylsilyl groups, C ₆ -C ₆₀ arylsilyl groups, C ₁ -C ₄₀ alkylboron groups, C ₆ -C ₆₀ the arylboronic group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ or the, form a condensed ring by combining adjacent tile In addition,

The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group and arylsilyl group of Ar ₁ to Ar _5, R ₁ and R ₂ , An alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group and an arylamine group are each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkoxy group, group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 hetero cycloalkyl, heteroaryl of C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 aryl group, C ₁ ~ C ₄₀ alkyloxy A C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, C ₆ ~ C ₆₀ aryl phosphine group of, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C to 1 or more substituents selected from the ₆₀ group consisting of aryl amines may be unsubstituted or substituted The. When Ar ₁ to Ar ₅ , R ₁ and R ₂ are substituted with a plurality of substituents, the plurality of substituents may be the same or different from each other.

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising a cathode, a cathode, 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 a compound represented by the above formula And an organic electroluminescent device.

In the present invention, alkyl means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl.

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

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

In the present invention, aryl means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

In the present invention, heteroaryl means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. It is also possible to include a form in which two or more rings are pendant or condensed with each other, and further, a condensed form with an aryl group may be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, aryloxy is a monovalent substituent represented by RO-, and R represents aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

In the present invention, alkyloxy is a monovalent substituent group represented by R'O-, wherein R 'represents alkyl having 1 to 40 carbon atoms, and includes a linear, branched or cyclic structure can do. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy and pentoxy.

In the present invention, arylamine refers to an amine substituted with aryl having 6 to 60 carbon atoms.

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

In the present invention, heterocycloalkyl means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon atom, preferably 1 to 3 carbons, of the ring is N, O, S or Se Lt; / RTI > Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

In the present invention, alkylsilyl is silyl substituted with alkyl having 1 to 40 carbon atoms, and arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms.

In the present invention, the condensed rings refer to condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.

When the compound represented by the general formula (1) of the present invention is used for an organic material layer (preferably, a light emitting material of a light emitting layer) of an organic electroluminescent device, efficiency (luminous efficiency and messaging efficiency), lifetime, Voltage and the like can be improved. Accordingly, the present invention can improve the performance and lifetime of a full-color organic electroluminescent panel.

Hereinafter, the present invention will be described.

1. Organic compounds

The organic compound of the present invention is a tribenzoazepin structure having an aromatic ring or a heteroaromatic ring condensed to form a basic skeleton as shown below. The aromatic ring or heteroaromatic ring condensed in the above-mentioned tribenzoazepin structure is not particularly limited, and examples thereof include indene, indole, benzothiophene, benzofuran, and benzoylol.

The host included in the phosphorescent light emitting layer in the organic material layer included in the organic electroluminescent device must have a triplet energy gap higher than that of the dopant. That is, in order to effectively provide phosphorescence from the dopant, the energy of the lowest excitation state of the host should be higher than the energy of the lowest emission state of the dopant. The compound represented by the formula (1) of the present invention has a specific substituent group introduced into the dibenzoazepine structure having a broad singlet energy level and a high triplet energy level, and exhibits a higher energy level than a dopant when applied as a host of a light emitting layer .

In addition, the compound represented by Formula 1 of the present invention having a high triplet energy of 2.3 eV or more prevents the excitons produced in the light emitting layer from diffusing into the adjacent electron transporting layer or hole transporting layer, thereby increasing the number of excitons contributing to light emission The luminous efficiency can be improved.

In addition, the compound represented by the general formula (1) of the present invention can have a wide bandgap by controlling the HOMO and LUMO energy levels according to the substituent to be introduced, and can have a high carrier transporting property. In addition, when an electron donor (EWG) having a large electron absorbing property and / or a large electron donating group (EDG) having an electron donating property are combined, the entire molecule can have a bipolar characteristic, thereby enhancing the bonding strength between the hole and the electron.

Meanwhile, the compound represented by the formula (1) of the present invention has various substituents, especially an aryl group and / or a heteroaryl group, introduced into the basic skeleton and the molecular weight of the compound is significantly increased to improve the glass transition temperature, For example, CBP). ≪ / RTI > The compound represented by the formula (1) is also effective for inhibiting crystallization of the organic material layer.

Accordingly, when the compound represented by Formula 1 of the present invention is applied to an organic material layer of an organic electroluminescent device, the performance and lifetime characteristics of the organic electroluminescent device can be greatly improved. Further, the lifetime of the organic electroluminescent device can be maximized by maximizing the performance of the full-color organic electroluminescent panel.

In these compounds represented by the general formula (I) of the present invention, X ₁ and X ₂ are independently _{N (Ar 1), O,} S, C (Ar 2) (Ar 3) and _{Si (Ar 4) (Ar 5} ) , respectively are selected from the group, given the characteristics of the organic EL device, preferably a N (Ar _1), O or S, and more preferably all of the N (Ar ₁₎ made of a. Y ₁ to Y ₁₂ are each independently C (R ₁ ) or N, and in consideration of the characteristics of the organic electroluminescent device, it is preferable that _one or all of N is C (R ₁ ). Y ₁₃ to Y ₁₆ are each independently C (R ₂ ) or N, and in consideration of the characteristics of the organic electroluminescent device, it is preferable that one or all of N is C (R ₂ ).

The compound represented by formula (1) of the present invention may be any one of compounds represented by the following formulas (3) to (11).

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

X ₁ , X ₂ , R _1, and R ₂ are the same as defined in Formula 1, wherein a plurality of R _{1 s} are the same or different from each other, and a plurality of R _{2 s} are the same as or different from each other .

The compound represented by the formula (1) of the present invention may be further compounded by any one of the compounds represented by the following formulas (12) to (20).

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

[Chemical Formula 19]

[Chemical Formula 20]

In the general formulas (12) to (20), Ar ₁ R ₁ and R ₂ are the same as defined in the general formula (1), wherein a plurality of R _{1 s} are the same or different from each other and a plurality of R _{2 s} are the same as or different from each other.

In the compounds represented by the general formula (1) of the present invention, Ar ₁ to Ar ₅ are each independently a C ₆ to C ₆₀ aryl group, a heteroaryl group C having 5 to 60 nuclear atoms to be ₆ ~ C ₆₀ aryl group and a C ₆ ~ amine selected from the group consisting of aryl silyl C ₆₀ are preferred. In particular, Ar ₁ is C ₆ ~ C ₆₀ heteroaryl group of the aryl group or 5 to 60 nuclear atoms is more preferable.

In the compound represented by Formula 1 of the present invention, R ₁ and R ₂ are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₆ to C ₆₀ aryl, A heteroaryl group having 5 to 60 nuclear atoms and an arylamine group having ₆ to ₆₀ carbon atoms.

Specifically, it is preferable that at least one of Ar ₁ R ₁ and R ₂ is a substituent represented by the following formula (21).

[Chemical Formula 21]

In Formula 21,

L is are selected from the group consisting of a single bond, a C ₆ ~ C ₄₀ aryl group and a nuclear atoms of 5 to 40 hetero arylene group for, particularly preferably a single bond, phenylene or biphenylene.

Z ₁ to Z ₅ are each independently N or C (R ₁₇ ), and at least one of them includes N, specifically, it is preferable to include 1 to 3 N.

Wherein R ₁₇ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl , A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group A C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine A pin group, an arylphosphine oxide group having ₆ to ₆₀ carbon atoms, and an arylamine group having ₆ to ₆₀ carbon atoms, or may be bonded to an adjacent group to form a condensed ring.

Wherein L in the arylene group, heteroarylene group, wherein R ₁₇ an alkyl group, an alkenyl group, an alkynyl group, a siteul group, a heterocycloalkyl group, an aryl group, a heteroaryl group, alkyloxy group, aryloxy group, alkyl silyl group , aryl silyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group, each independently, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ alkynyl group of C _40, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group, the group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, C ₆ ~ C ₆₀ arylboronic group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ substituted 1 or more selected from the group consisting of an aryl amine of the C ₆₀ of the As may be unsubstituted or substituted.

The substituent represented by the formula (21) may be embodied by any one of substituents represented by the following formulas (A-1) to (A-15).

In the above formulas A-1 to A-15,

L And R ₁₇ are the same as defined in the above formula (21), wherein a plurality of R _{17 s} are the same as or different from each other,

R ₂₁ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, aryloxy nuclear atoms 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C _60, alkyloxy group of C ₁ ~ C ₄₀ , An arylamine group of C ₆ to C ₆₀ , a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of C ₆₀ or aryl silyl, by combining groups of adjacent, may form a condensed ring,

Alkyl group of the R _21, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, the arylphosphine oxide group and the arylamine group are each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, alkyl, nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 of the heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C of ₆ ~ C ₆₀ aryl oxy group, C ₁ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic in, aryl of C ₆ ~ C ₆₀ phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl amines may be unsubstituted or substituted by one substituent at least one selected from the group consisting of,

n is an integer of 0 to 4;

Specifically, in the compound represented by the general formula (1) of the present invention, Ar ₁ to Ar ₅ R ₁ and R ₂ are each independently selected from the group consisting of hydrogen or the substituents represented by the following S1 to S204.

The compound represented by the formula (1) of the present invention can be embodied by the following exemplified compounds, but the compound represented by the formula (1) of the present invention is not limited to the following compounds.

2. Organic electroluminescent device

The present invention relates to an organic electroluminescent device comprising at least an anode, a cathode, 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 a compound represented by Formula 1 An organic electroluminescent device is provided. At this time, the compounds may be used alone or in combination of two or more.

The one or more organic material layers may be at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. Here, the organic compound layer including the compound represented by Formula 1 is preferably a light emitting layer.

The light emitting layer of the organic electroluminescent device of the present invention may include a host material, wherein the host material may include a compound represented by the above formula (1). When the compound represented by Formula 1 is contained as a light emitting layer material of an organic electroluminescent device, preferably a blue, green, or red phosphorescent host material, 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 of the present invention is not particularly limited, but 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 laminated. An electron injection layer may be further stacked on the electron transport layer.

Further, the structure of the organic electroluminescent device of the present invention may be a structure in which an anode, one or more organic material layers and a cathode are sequentially laminated, and an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic material layer.

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

As the substrate included in the organic electroluminescent device of the present invention, 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 may be used.

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 a multilayer such as LiF / Al or LiO ₂ / Structural materials and the like can be used.

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

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 IAz-1

Synthesis of 7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-tribenzo [b, d, f] azepine

A solution of 7-chloro-9H-tribenzo [b, d, f] azepine (150 g, 540.0 mol), 4,4,4 ', 4,5,5,5,5- '-bi (1,3,2-dioxaborolane) ( 150 g, 594 mmol), Pd (dppf) Cl 2 (14 g, 16 mmol), KOAc (152 g, 1620.0 mmol) and 1,4-dioxane (2000 ml) were mixed and stirred at 130 ° C for 12 hours. After the reaction was completed, the organic layer was extracted with methylene chloride. The solvent was removed from the obtained organic layer and the residue was purified by column chromatography (Hexane: MC = 3: 2 (v / v)) to obtain 7- (4,4,5,5- -1,3,2-dioxaborolan-2-yl) -9H-tribenzo [b, d, f] azepine (149 g, yield 75%).

^{1 H-NMR: δ 1.24 (} s, 12H), 6.50 (s, 1H), 6.69 (m, 1H), 6.87 (m, 1H), 7.16-7.17 (m, 2H), 7.47-7.54 (m, 4H ), 7.85 (m, 2H)

<Step 2> Synthesis of 7- (2-nitrophenyl) -9H-tribenzo [b, d, f] azepine

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-tribenzo [b, d, f] azepine (148 g, 403 mmol) iodo-2-nitrobenzene (100 g, 403 mmol) and Pd (PPh ₃ ) ₄ (23 g, 20 mmol) were mixed and K ₂ CO ₃ (167 g, 1210 mmol), 1,4- ml) _and H ₂ O (400 ml) were added, and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate. The solvent was removed from the obtained organic layer and the residue was purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain 7- (2-nitrophenyl) -9H- d, f] azepine (99 g, yield: 68%).

^{1 H-NMR: δ 4.0 (} s, 1H), 6.61-6.69 (m, 2H), 6.87-6.95 (m, 2H), 7.16 (m, 1H), 7.47-7.67 (m, 5H), 7.85-7.90 (m, 3 H), 8.00-8. 05 (m, 2 H)

<Step 3> Synthesis of 7- (2-nitrophenyl) -9-phenyl-9H-tribenzo [b, d, f] azepine

Iodobenzene (55 g, 271 mmol), Cu (8.6 g, 135 mmol), K ₂ (dibenzylideneacetone) CO ₃ (112 g, 815 mmol) and nitrobenzene (990 ml) were mixed and stirred at 190 ° C for 12 hours. After completion of the reaction, nitrobenzene was removed and the residue was extracted with methylene chloride. The residue was purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain 7- (2-nitrophenyl) -9-phenyl-9H-tribenzo [ , d, f] azepine (86 g, yield: 72%).

^{1 H-NMR: δ 6.61-6.69 (} m, 4H), 6.81-6.95 (m, 3H), 7.16-7.20 (m, 3H), 7.47-7.67 (m, 5H), 7.85-7.90 (m, 3H) , 8.00-8. 05 (m, 2H)

<Step 4> Synthesis of IAz-1

Dibenzo [b, d, f] azepine (86 g, 195 mmol), PPh ₃ (128 g, 488 mmol) and 1,2-dichlorobenzene (880 ml) were mixed and stirred for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain IAz-1 (59 g, yield: 74%).

^{1 H-NMR: δ 6.63-6.69 (} m, 3H), 6.81-6.87 (m, 2H), 7.16-7.29 (m, 4H), 7.47-7.63 (m, 7H), 7.80-7.85 (m, 2H) , 8.12 (m, 1 H), 11.70 (s, 1 H)

[Preparation Example 2] Synthesis of IAz-2

Synthesis of 6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-tribenzo [b, d, f] azepine

(150 g, 540.0 mol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2, (150 g, 594 mmol), Pd (dppf) Cl ₂ (14 g, 16 mmol), KOAc (152 g, 1620.0 mmol) and 1,4-dioxane 2000 ml) were mixed and stirred at 130 ° C for 12 hours. After the reaction was completed, the organic layer was extracted with methylene chloride. The solvent was removed from the obtained organic layer and purified by column chromatography (Hexane: MC = 3: 2 (v / v)) to obtain 6- (4,4,5,5-tetramethyl -1,3,2-dioxaborolan-2-yl) -9H-tribenzo [b, d, f] azepine (155 g, yield: 78%).

^{1 H-NMR: δ 1.24 (} s, 12H), 6.69 (m, 2H), 6.87 (m, 1H), 7.16-7.2 (m, 2H), 7.46-7.54 (m, 4H), 7.85 (m, 2H )

<Step 2> Synthesis of 6- (2-nitrophenyl) -9H-tribenzo [b, d, f] azepine

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-tribenzo [b, d, f] azepine (155 g, 419 mmol) iodo-2-nitrobenzene (104 g , 419 mmol) and _{Pd (PPh 3) 4 (24} g, 20 mmol) were mixed, and _{then, K 2 CO 3 (174 g} , 1259 mmol), 1,4-dioxane (1600 ml) _and H ₂ O (400 ml) were added thereto, and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the solvent was removed from the organic layer obtained by extraction with ethyl acetate and the residue was purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain 6- (2-nitrophenyl) -9H-tribenzo [ , d, f] azepine (107 g, yield: 70%).

^{1 H-NMR: δ 4.0 (} s, 1H), 6.69-6.75 (m, 2H), 6.87 (m, 1H), 7.16 (m, 1H), 7.47-7.54 (m, 5H), 7.67 (m, 1H ), 7.85-7.90 (m, 3H), 8.00-8.05 (m, 2H)

Step 3 Synthesis of 6- (2-nitrophenyl) -9-phenyl-9H-tribenzo [b, d, f] azepine

(107 g, 293 mmol), iodobenzene (59 g, 293 mmol), Cu (9.3 g, 146 mmol), K ₂ (dibenzylideneacetone) CO ₃ (121 g, 880 mmol) and nitrobenzene (990 ml) were mixed and stirred at 190 ° C for 12 hours. After completion of the reaction, nitrobenzene was removed and the residue was extracted with methylene chloride. The residue was purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain 6- (2-nitrophenyl) -9-phenyl-9H-tribenzo [ , d, f] azepine (95 g, yield: 74%).

^{1 H-NMR: δ 6.63-6.87 (} m, 6H), 7.45-7.54 (m, 5H), 7.67 (m, 1H), 7.85-7.90 (m, 3H), 8.00-8.05 (m, 2H)

<Step 4> Synthesis of IAz-2

9-phenyl-9H-tribenzo [b, d, f] azepine (95 g, 215 mmol), PPh ₃ (141 g, 539 mmol) and 1,2-dichlorobenzene ml) were mixed and stirred for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain IAz-2 (67 g, yield 76%).

^{1 H-NMR: δ 6.63-6.87 (} m, 6H), 7.16-7.29 (m, 4H), 7.47-7.63 (m, 5H), 7.85 (m, 2H), 7.99 (m, 1H), 8.12 (m , 1H)

[Preparation Example 3] Synthesis of IAz-3

Synthesis of 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-tribenzo [b, d, f] azepine

B, d, f] azepine (150 g, 540.0 mol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl- (150 g, 594 mmol), Pd (dppf) Cl ₂ (14 g, 16 mmol), KOAc (152 g, 1620.0 mmol) and 1,4-dioxane 2000 ml) were mixed and stirred at 130 ° C for 12 hours. After the reaction was completed, the organic layer was extracted with methylene chloride. The solvent was removed from the obtained organic layer and the residue was purified by column chromatography (Hexane: MC = 3: 2 (v / v)) to obtain 5- (4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-tribenzo [b, d, f] azepine (143 g, yield: 72%).

¹ H-NMR:? 1.24 (s, 12H), 6.69 (m, 2H), 6.87 (m, 1H), 7.16-7.17 (m, 3H), 7.47-7.54 )

<Step 2> Synthesis of 5- (2-nitrophenyl) -9H-tribenzo [b, d, f] azepine

B, d, f] azepine (143 g, 387 mmol), 1- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- iodo-2-nitrobenzene (96 g, 387 mmol) and Pd (PPh ₃ ) ₄ (22 g, 19 mmol) were mixed and then K ₂ CO ₃ (160 g, 1161 mmol), 1,4- ml) _and H ₂ O (400 ml) were added thereto, and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate. The solvent was removed from the obtained organic layer and the residue was purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain 5- (2-nitrophenyl) -9H- d, f] azepine (98 g, yield: 70%).

^{1 H-NMR: δ 4.0 (} s, 1H), 6.65-6.69 (m, 2H), 6.87 (m, 1H), 7.16-7.21 (m, 2H), 7.40-7.54 (m, 4H), 7.85-7.90 (m, 3 H), 8.00-8. 05 (m, 2 H)

<Step 3> Synthesis of 5- (2-nitrophenyl) -9-phenyl-9H-tribenzo [b, d, f] azepine

(98 g, 268 mmol), iodobenzene (55 g, 268 mmol), Cu (8.5 g, 134 mmol), K ₂ (dibenzylideneacetone) CO ₃ (111 g, 806 mmol) and nitrobenzene (990 ml) were mixed and stirred at 190 ° C for 12 hours. After completion of the reaction, nitrobenzene was removed and the residue was extracted with methylene chloride. The residue was purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to give 5- (2-nitrophenyl) -9-phenyl-9H-tribenzo [ , d, f] azepine (85 g, yield: 72%).

^{1 H-NMR: δ 6.63-6.69 (} m, 4H), 6.81-6.87 (m, 2H), 7.16-7.21 (m, 4H), 7.40-7.54 (m, 4H), 7.67 (m, 1H), 7.85 -7.90 (m, 3H), 8.00-8.05 (m, 2H)

<Step 4> Synthesis of IAz-3

Dibenzo [b, d, f] azepine (95 g, 215 mmol), PPh ₃ (141 g, 539 mmol) and 1,2-dichlorobenzene (900 ml) were mixed and stirred for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain IAz-3 (61 g, yield 70%).

^{1 H-NMR: δ 6.63-6.69 (} m, 3H), 6.81-6.87 (m, 3H), 7.16-7.34 (m, 5H), 7.47-7.63 (m, 5H), 7.85 (m, 2H), 8.12 (m, 1 H), 11.70 (s, 1 H)

[Preparation Example 4] Synthesis of IAz-4

Synthesis of 8- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-tribenzo [b, d, f] azepine

B, d, f] azepine (150 g, 540.0 mmol), 4,4,4 ', 4', 5,5,5 ' (150 g, 594 mmol), Pd (dppf) Cl ₂ (14 g, 16 mmol), KOAc (152 g, 1620.0 mmol) and 1,4-dioxane 2000 ml) were mixed and stirred at 130 ° C for 12 hours. After the reaction was completed, the organic layer was extracted with methylene chloride, the solvent was removed from the organic layer, and the residue was purified by column chromatography (Hexane: MC = 3: 2 (v / v)) to obtain 8- (4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-tribenzo [b, d, f] azepine (137 g, yield 69%).

^{1 H-NMR: δ 1.24 (} s, 12H), 6.69 (m, 1H), 6.87 (m, 2H), 7.16 (m, 1H), 7.46-7.54 (m, 4H), 7.85 (m, 2H)

<Step 2> Synthesis of 8- (2-nitrophenyl) -9H-tribenzo [b, d, f] azepine

B, d, f] azepine (137 g, 371 mmol), 1- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- iodo-2-nitrobenzene (92 g, 371 mmol) and Pd (PPh ₃ ) ₄ (21 g, 18 mmol) were mixed and K ₂ CO ₃ (153 g, 1113 mmol), 1,4- ml) _and H ₂ O (400 ml) were added thereto, and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the solvent was removed from the organic layer obtained by extraction with ethyl acetate, and the residue was purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain 8- (2-nitrophenyl) -9H-tribenzo [b , d, f] azepine (100 g, yield: 74%).

^{1 H-NMR: δ 4.0 (} s, 1H), 6.69 (m, 1H), 6.87-6.93 (m, 2H), 7.16 (m, 1H), 7.47-7.54 (m, 5H), 7.67 (m, 1H ), 7.85-7.90 (m, 3H), 8.00-8.05 (m, 2H)

Step 3 Synthesis of 8- (2-nitrophenyl) -9-phenyl-9H-tribenzo [b, d, f] azepine

(100 g, 274 mmol), iodobenzene (55 g, 274 mmol), Cu (8.7 g, 137 mmol), K ₂ (dibenzylideneacetone) CO ₃ (113 g, 823 mmol) and nitrobenzene (990 ml) were mixed and stirred at 190 ° C for 12 hours. After completion of the reaction, nitrobenzene was removed and the residue was extracted with methylene chloride. The residue was purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to give 8- (2-nitrophenyl) -9-phenyl-9H-tribenzo [ , d, f] azepine (91 g, yield: 76%).

¹ H-NMR:? 6.63-6.69 (m, 3H), 6.81-6.93 (m, 3H), 7.16-7.20 (m, 3H), 7.47-7.54 -7.90 (m, 3H), 8.00-8.05 (m, 2H)

<Step 4> Synthesis of IAz-4

Dibenzo [b, d, f] azepine (91 g, 206 mmol), PPh ₃ (135 g, 516 mmol) and 1,2-dichlorobenzene (880 ml) were mixed and stirred for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain IAz-4 (59 g, yield: 71%).

¹ H-NMR:? 6.63-6.69 (m, 3H), 6.81-6.87 (m, 2H), 7.05 (m, 1H), 7.16-7.29 (m, 4H), 7.47-7.63 -7.85 (m, 2 H), 8.12 (m, 1 H), 11.70 (s, 1 H)

[Preparation Example 5] Synthesis of IAz-5

<Step 1> Synthesis of 7- (4-nitropyridin-3-yl) -9H-tribenzo [b, d, f] azepine

B, d, f] azepine (143 g, 387 mmol), 3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- iodo-4-nitropyridine (96 g, 387 mmol) and Pd (PPh ₃ ) ₄ (22 g, 19 mmol) were mixed and then K ₂ CO ₃ (160 g, 1161 mmol), 1,4- ml) _and H ₂ O (400 ml) were added thereto, and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the solvent was removed from the organic layer obtained by extraction with ethyl acetate and the residue was purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain 7- (4-nitropyridin- -tribenzo [b, d, f] azepine (103 g, yield: 73%).

¹ H-NMR:? 4.0 (s, 1H), 6.61-6.69 (m, 2H), 6.87-6.95 (m, 2H), 7.16 (m, 3 H), 8.15 (m, 1 H), 9.50 (m, 1 H)

Synthesis of 7- (4-nitropyridin-3-yl) -9-phenyl-9H-tribenzo [b, d, f] azepine

(103 g, 281 mmol), iodobenzene (57 g, 281 mmol), Cu (8.9 g, 140 mmol) in a stream of nitrogen were added to a solution of 7- (4-nitropyridin-3-yl) -9H- ), K ₂ CO ₃ (116 g, 845 mmol) and nitrobenzene (990 ml) were mixed and stirred at 190 ° C for 12 hours. After completion of the reaction, nitrobenzene was removed, and the residue was extracted with methylene chloride and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain 7- (4-nitropyridin- -tribenzo [b, d, f] azepine (84 g, yield: 68%).

^{1 H-NMR: δ 6.61-6.69 (} m, 4H), 6.81-6.95 (m, 3H), 7.16-7.20 (m, 3H), 7.47-7.60 (m, 4H), 7.85-7.92 (m, 3H) , 8.15 (m, 1 H), 9.50 (m, 1 H)

<Step 3> Synthesis of IAz-5

(84 g, 190 mmol), PPh ₃ (124 g, 475 mmol), and 1,2 (4-nitropyridin-3-yl) -9-phenyl-9H-tribenzo [ -dichlorobenzene (880 ml) were mixed and stirred for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain IAz-5 (50 g, yield 65%).

^{1 H-NMR: δ 6.63-6.69 (} m, 3H), 6.81-6.87 (m, 2H), 7.16-7.20 (m, 3H), 7.47-7.54 (m, 6H), 7.85 (m, 2H), 8.43 (m, 1 H), 9.34 (m, 1 H), 11.70 (s, 1 H)

[Preparation Example 6] Synthesis of IAz-6 "

<Step 1> Synthesis of 7- (5-chloro-2-nitrophenyl) -9H-tribenzo [b, d, f] azepine

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-tribenzo [b, d, f] azepine (147 g, 398 mmol) chloro-2-iodo-1- nitrobenzene (112 g, 398 mmol) and _{Pd (PPh 3) 4 (23} g, 19 mmol) were mixed, and _{then, K 2 CO 3 (165 g} , 1194 mmol), 1,4 -dioxane (1600 ml) _and H ₂ O (400 ml) were placed, and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the solvent was removed from the organic layer obtained by extraction with ethyl acetate, and the residue was purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain 7- (5-chloro-2-nitrophenyl) -tribenzo [b, d, f] azepine (112 g, yield: 71%).

^{1 H-NMR: δ 4.0 (} s, 1H), 6.61-6.69 (m, 2H), 6.87-6.95 (m, 2H), 7.16 (m, 1H), 7.47-7.60 (m, 4H), 7.71 (m , &Lt; / RTI &gt; 1H) 7.85 (m, 2H), 8.26-8.27 (m, 2H)

Step 2 Synthesis of 7- (5-chloro-2-nitrophenyl) -9-phenyl-9H-tribenzo [b, d, f] azepine

(112 g, 280 mmol), iodobenzene (57 g, 280 mmol) and Cu (8.9 g, 140 mmol) in a stream of nitrogen were added to a solution of 7- (5-chloro-2- nitrophenyl) -9H- ), K ₂ CO ₃ (116 g, 842 mmol) and nitrobenzene (990 ml) were mixed and stirred at 190 ° C for 12 hours. After completion of the reaction, nitrobenzene was removed, and the residue was extracted with methylene chloride. The residue was purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain 7- (5-chloro-2-nitrophenyl) -tribenzo [b, d, f] azepine (92 g, yield 69%).

¹ H-NMR:? 6.61-6.69 (m, 4H), 6.81-6.95 (m, 3H), 7.16-7.20 (m, 3H), 7.47-7.60 (m, 2 H), 8.26 - 8.27 (m, 2 H)

<Step 3> Synthesis of IAz-6

(92 g, 193 mmol), PPh ₃ (127 g, 484 mmol), and 1,2 (2-chloro-2-nitrophenyl) -9- -dichlorobenzene (880 ml) were mixed and stirred for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain IAz-6 (58 g, yield 68%).

^{1 H-NMR: δ 6.63-6.69 (} m, 3H), 6.81-6.87 (m, 2H), 7.09-7.29 (m, 4H), 7.47-7.57 (m, 6H), 7.85 (m, 2H), 11.70 (s, 1 H)

<Step 4> Synthesis of IAz-6 '

(58 g, 130 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane ) (150 g, 594 mmol) , Pd (dppf) Cl 2 (36 g, 144 mmol), KOAc (36 g, 392.0 mmol) and a mixture of 1,4-dioxane (500 ml) for 12 hours and at 130 ℃ Lt; / RTI &gt; After completion of the reaction, the solvent was removed from the organic layer obtained by extraction with methylene chloride, and the residue was purified by column chromatography (Hexane: MC = 3: 2 (v / v)) to obtain IAz-6 '(51 g, yield: 73% &Lt; / RTI &gt;

¹ H-NMR:? 1.24 (s, 12H), 6.63-6.69 (m, 3H), 6.81-6.87 (m, 3H), 7.10-7.20 (m, 4H), 7.47-7.54 (m, 2 H), 11.70 (s, 1 H)

<Step 5> Synthesis of IAz-6

(51 g, 95 mmol), 2-bromo-4,6-diphenylbenzene (29 g, 95 mmol) and Pd (PPh ₃ ) ₄ (5.5 g, 4.7 mmol) were mixed in a nitrogen stream, K ₂ CO ₃ (40 g, 286 mmol), 1,4-dioxane (800 ml) _and H ₂ O (200 ml) were placed and stirred at 110 ° C for 12 hours. After completion of the reaction, the solvent was removed from the organic layer obtained by extraction with ethyl acetate, and the residue was purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain IAz-6 "(44 g, yield: 74% &Lt; / RTI &gt;

^{1 H-NMR: δ 6.63-6.69 (} m, 3H), 6.81-6.87 (m, 2H), 7.16-7.20 (m, 3H), 7.41-7.54 (m, 15H), 7.66-7.69 (m, 3H) , 7.85-7.87 (m, 3H), 11.70 (s, 1 H)

[Synthesis Example 1] Synthesis of Compound 1-1

(2.5 g, 6.1 mmol), 2-bromo-4,6-diphenylpyrimidine (2.3 g, 7.3 mmol), CuI (0.1 g, 0.61 mmol), 1,10-phenanthroline mmol), Cs ₂ CO ₃ (3.9 g, 12 mmol) and nitrobenzene (30 ml) were mixed and stirred at 210 ° C for 3 hours. After completion of the reaction, the solid salt was filtered and then purified by column chromatography to obtain Compound 1-1 (2.7 g, yield 70%).

Mass (theory: 638.25, measurement: 638 g / mol)

[Synthesis Example 2] Synthesis of Compound 1-2

The same procedure as in Synthesis Example 1 was carried out except that 4-bromo-2,6-diphenylpyrimidine (2.3 g, 7.3 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine to obtain Compound 1-2 (2.8 g, Yield: 72%).

Mass (theory: 638.25, measurement: 638 g / mol)

[Synthesis Example 3] Synthesis of Compound 1-3

The same procedure as in Synthesis Example 1 was carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine (1.9 g, 7.3 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine Compound 1-3 (2.9 g, yield 73%) was obtained.

Mass (theory: 639.24, found: 639 g / mol)

[Synthesis Example 4] Synthesis of Compound 1-4

Except that 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2.9 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine Was carried out to obtain Compound 1-4 (3.0 g, yield 69%).

Mass (theory: 715.27, found: 715 g / mol)

[Synthesis Example 5] Synthesis of Compound 1-5

(3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2.9 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine Was performed to obtain Compound 1-5 (2.9 g, yield 67%).

Mass (theory: 715.27, found: 715 g / mol)

[Synthesis Example 6] Synthesis of Compound 1-6

The same procedure as in Synthesis Example 1 was carried out except that 2- (3-bromophenyl) dibenzo [b, d] thiophene (2.5 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine, 6 (2.7 g, yield 65%).

Mass (theory: 666.21, found: 666 g / mol)

[Synthesis Example 7] Synthesis of Compound 1-7

The same procedure as in Synthesis Example 1 was carried out except that 2-bromodibenzo [b, d] furan (1.8 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine to obtain Compound 1-7 Yield: 72%).

Mass (theory: 574.20, measurement: 574 g / mol)

[Synthesis Example 8] Synthesis of Compound 1-8

The procedure of Synthesis Example 1 was repeated except that 2- (4-bromophenyl) triphenylene (2.8 g, 7.3 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine to obtain Compound 1-8 68%).

Mass (theory: 710.27, measurement: 710 g / mol)

[Synthesis Example 9] Synthesis of Compound 1-9

The procedure of Synthesis Example 1 was repeated except that 2-chloro-4-phenylquinazoline (1.8 g, 7.3 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine to obtain Compound 1-9 (2.8 g, yield 75 %).

Mass (theory: 612.23, measurement: 612 g / mol)

[Synthesis Example 10] Synthesis of Compound 1-10

The same procedure as in Synthesis Example 1 was performed except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.7 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine To obtain Compound 1-10 (3.3 g, yield 72%).

Mass (theory: 738.28, found: 738 g / mol)

[Synthesis Example 11] Synthesis of Compound 1-11

(2.5 g, 6.1 mmol), 2-bromo-4,6-diphenylpyrimidine (2.3 g, 7.3 mmol), CuI (0.1 g, 0.61 mmol), 1,10-phenanthroline mmol), Cs ₂ CO ₃ (3.9 g, 12 mmol) and nitrobenzene (30 ml) were mixed and stirred at 210 ° C for 3 hours. After completion of the reaction, the solid salt was filtered and then purified by column chromatography to obtain Compound 1-11 (2.8 g, yield 72%).

Mass (theory: 638.25, measurement: 638 g / mol)

[Synthesis Example 12] Synthesis of Compound 1-12

The compound 1-12 (2.8 g, 7.3 mmol) was treated in the same manner as in Synthesis Example 11, except that 4-bromo-2,6-diphenylpyrimidine (2.3 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine. Yield: 71%).

Mass (theory: 638.25, measurement: 638 g / mol)

[Synthesis Example 13] Synthesis of Compound 1-13

The procedure was the same as that of Synthesis Example 11 except that 2-chloro-4,6-diphenyl-1,3,5-triazine (1.9 g, 7.3 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine Compound 1-13 (2.9 g, yield 74%) was obtained.

Mass (theory: 639.24, found: 639 g / mol)

[Synthesis Example 14] Synthesis of Compound 1-14

Except that 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2.8 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine Was performed to obtain Compound 1-14 (3.2 g, yield 74%).

Mass (theory: 715.27, found: 715 g / mol)

[Synthesis Example 15] Synthesis of Compound 1-15

Except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2.9 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine Was performed to obtain Compound 1-15 (3.0 g, yield 69%).

Mass (theory: 715.27, found: 715 g / mol)

[Synthesis Example 16] Synthesis of Compound 1-16

The same procedure as in Synthesis Example 11 was carried out except that 2- (3-bromophenyl) dibenzo [b, d] thiophene (2.5 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine, 16 (2.6 g, yield 65%).

Mass (theory: 666.21, found: 666 g / mol)

[Synthesis Example 17] Synthesis of Compound 1-17

The same procedure as in Synthesis Example 11 was carried out except that 2-bromodibenzo [b, d] furan (1.8 g, 7.3 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine to obtain Compound 1-17 Yield: 71%).

Mass (theory: 590.18, measurement: 590 g / mol)

[Synthesis Example 18] Synthesis of Compound 1-18

The same procedure as in Synthesis Example 11 was carried out except that 2- (4-bromophenyl) triphenylene (2.8 g, 7.3 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine to obtain Compound 1-18 73%).

Mass (theory: 710.27, measurement: 710 g / mol)

[Synthesis Example 19] Synthesis of Compound 1-19

The procedure of Synthesis Example 11 was repeated except that 2-chloro-4-phenylquinazoline (1.8 g, 7.3 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine to obtain Compound 1-19 %).

Mass (theory: 612.23, measurement: 612 g / mol)

[Synthesis Example 20] Synthesis of Compound 1-20

The same procedure as in Synthesis Example 11 was performed except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.7 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine To obtain Compound 1-20 (3.4 g, yield 75%).

Mass (theory: 738.28, found: 738 g / mol)

[Synthesis Example 21] Synthesis of Compound 2-1

(2.5 g, 6.1 mmol), 2-bromo-4,6-diphenylpyrimidine (2.3 g, 7.3 mmol), CuI (0.1 g, 0.61 mmol), 1,10-phenanthroline mmol), Cs ₂ CO ₃ (3.9 g, 12 mmol) and nitrobenzene (30 ml) were mixed and stirred at 210 ° C for 3 hours. After completion of the reaction, the solid salt was filtered and then purified by column chromatography to obtain Compound 2-1 (2.9 g, yield 76%).

Mass (theory: 638.25, measurement: 638 g / mol)

[Synthesis Example 22] Synthesis of Compound 2-2

2-2 (2.8 g, 7.3 mmol) was obtained by following the same procedure as in Synthesis Example 21, except that 4-bromo-2,6-diphenylpyrimidine (2.3 g, 7.3 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine. Yield: 72%).

Mass (theory: 638.25, measurement: 638 g / mol)

[Synthesis Example 23] Synthesis of Compound 2-3

The same procedure as in Synthesis Example 21 was carried out except that 2-chloro-4,6-diphenyl-1,3,5-triazine (1.9 g, 7.3 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine Compound 2-3 (2.8 g, yield 72%) was obtained.

Mass (theory: 639.24, found: 639 g / mol)

[Synthesis Example 24] Synthesis of Compound 2-4

Except that 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2.8 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine Was performed to obtain Compound 2-4 (3.0 g, yield 69%).

Mass (theory: 715.27, found: 715 g / mol)

[Synthesis Example 25] Synthesis of Compound 2-5

Except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2.9 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine To obtain Compound 2-5 (2.8 g, yield 66%).

Mass (theory: 715.27, found: 715 g / mol)

[Synthesis Example 26] Synthesis of Compound 2-6

The procedure of Synthetic Example 21 was repeated except that 2- (3-bromophenyl) dibenzo [b, d] thiophene (2.5 g, 7.3 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine to obtain 2- 6 (2.6 g, yield 66%).

Mass (theory: 666.21, found: 666 g / mol)

[Synthesis Example 27] Synthesis of Compound 2-7

The same procedure as in Synthesis Example 21 was carried out except that 2-bromodibenzo [b, d] furan (1.8 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine, Yield: 70%).

Mass (theory: 574.20, measurement: 574 g / mol)

[Synthesis Example 28] Synthesis of Compound 2-8

The same procedure as in Synthesis Example 21 was repeated but using 2- (4-bromophenyl) triphenylene (2.8 g, 7.3 mmol) instead of 2-bromo-4,6-diphenylpyrimidine to obtain Compound 2-8 74%).

Mass (theory: 710.27, measurement: 710 g / mol)

[Synthesis Example 29] Synthesis of Compound 2-9

(2.6 g, yield 72%) was obtained by following the same procedure as in Synthesis Example 21, except that 2-chloro-4-phenylquinazoline (1.8 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine. %).

Mass (theory: 612.23, measurement: 612 g / mol)

[Synthesis Example 30] Synthesis of Compound 2-10

The same procedure as in Synthesis Example 21 was carried out except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.7 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine To obtain Compound 2-10 (3.1 g, yield 70%).

Mass (theory: 738.28, found: 738 g / mol)

[Synthesis Example 31] Synthesis of Compound 3-1

(2.5 g, 6.1 mmol), 2-bromo-4,6-diphenylpyrimidine (2.3 g, 7.3 mmol), CuI (0.1 g, 0.61 mmol), 1,10-phenanthroline mmol), Cs ₂ CO ₃ (3.9 g, 12 mmol) and nitrobenzene (30 ml) were mixed and stirred at 210 ° C for 3 hours. After completion of the reaction, the solid salt was filtered and then purified by column chromatography to obtain Compound 3-1 (2.8 g, yield 72%).

Mass (theory: 638.25, measurement: 638 g / mol)

[Synthesis Example 32] Synthesis of Compound 3-2

The same procedure as in Synthesis Example 31 was repeated but using 4-bromo-2,6-diphenylpyrimidine (2.3 g, 7.3 mmol) instead of 2-bromo-4,6-diphenylpyrimidine to obtain Compound 3-2 Yield: 70%).

Mass (theory: 638.25, measurement: 638 g / mol)

[Synthesis Example 33] Synthesis of Compound 3-3

The same procedure was followed as in Synthesis 31 except that 2-chloro-4,6-diphenyl-1,3,5-triazine (1.9 g, 7.3 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine Compound 3-3 (2.6 g, yield 67%) was obtained.

Mass (theory: 639.24, found: 639 g / mol)

[Synthesis Example 34] Synthesis of Compound 3-4

Except that 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2.9 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine Was performed to obtain Compound 3-4 (3.0 g, yield 69%).

Mass (theory: 715.27, found: 715 g / mol)

[Synthesis Example 35] Synthesis of Compound 3-5

Except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2.9 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine To obtain Compound 3-5 (2.6 g, yield 66%).

Mass (theory: 715.27, found: 715 g / mol)

[Synthesis Example 36] Synthesis of Compound 3-6

The procedure of Synthesis Example 31 was repeated except for using 2- (3-bromophenyl) dibenzo [b, d] thiophene (2.4 g, 7.3 mmol) instead of 2-bromo-4,6-diphenylpyrimidine to obtain 3- 6 (2.9 g, yield 71%).

Mass (theory: 666.21, found: 666 g / mol)

[Synthesis Example 37] Synthesis of Compound 3-7

The same procedure as in Synthesis Example 31 was repeated but using 2-bromodibenzo [b, d] furan (1.8 g, 7.3 mmol) instead of 2-bromo-4,6-diphenylpyrimidine to obtain 3- Yield: 73%).

Mass (theory: 574.20, measurement: 574 g / mol)

[Synthesis Example 38] Synthesis of Compound 3-8

The same procedure as in Synthesis Example 31 was repeated, except that 2- (4-bromophenyl) triphenylene (2.8 g, 7.3 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine to obtain 3-8 74%).

Mass (theory: 710.27, measurement: 710 g / mol)

[Synthesis Example 39] Synthesis of Compound 3-9

(2.7 g, yield 74%) was obtained by following the same procedure as in Synthesis 31 except that 2-chloro-4-phenylquinazoline (1.8 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine. %).

Mass (theory: 612.23, measurement: 612 g / mol)

[Synthesis Example 40] Synthesis of Compound 3-10

The same procedure as in Synthesis Example 31 was carried out except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.7 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine To obtain Compound 3-10 (3.0 g, yield 68%).

Mass (theory: 738.28, found: 738 g / mol)

[Synthesis Example 41] Synthesis of Compound 4-1

(2.5 g, 6.1 mmol), 2-bromo-4,6-diphenylpyrimidine (2.2 g, 7.3 mmol), CuI (0.1 g, 0.61 mmol), 1,10-phenanthroline mmol), Cs ₂ CO ₃ (3.9 g, 12 mmol) and nitrobenzene (30 ml) were mixed and stirred at 210 ° C for 3 hours. After completion of the reaction, the solid salt was filtered and then purified by column chromatography to obtain Compound 4-1 (2.6 g, yield 68%).

Mass (theory: 639.24, found: 639 g / mol)

[Synthesis Example 42] Synthesis of Compound 4-2

Compound 4-2 (2.8 g, 7.3 mmol) was obtained by following the same procedure as Synthesis Example 41, except that 4-bromo-2,6-diphenylpyrimidine (2.3 g, 7.3 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine. Yield: 72%).

Mass (theory: 639.24, found: 639 g / mol)

[Synthesis Example 43] Synthesis of Compound 4-3

The procedure of Synthesis Example 41 was repeated except that 2-chloro-4,6-diphenyl-1,3,5-triazine (1.9 g, 7.3 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine Compound 4-3 (2.7 g, yield 69%) was obtained.

Mass (theory: 640.24, measured: 640 g / mol)

[Synthesis Example 44] Synthesis of Compound 4-4

Was prepared in the same manner as in Synthesis Example 41, except that 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2.8 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine. Was performed to obtain compound 4-4 (2.9 g, yield 68%).

Mass (theory: 716.27, measurement: 716 g / mol)

[Synthesis Example 45] Synthesis of Compound 4-5

Except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2.9 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine Was performed to obtain Compound 4-5 (3.0 g, yield 70%).

Mass (theory: 716.27, measurement: 716 g / mol)

[Synthesis Example 46] Synthesis of Compound 4-6

The same procedure as in Synthesis Example 41 was carried out except that 2- (3-bromophenyl) dibenzo [b, d] thiophene (2.5 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine, 6 (2.6 g, yield 65%).

Mass (calc .: 667.21, found: 667 g / mol)

[Synthesis Example 47] Synthesis of Compound 4-7

The same procedure as in Synthesis Example 41 was repeated but using 2-bromodibenzo [b, d] furan (1.8 g, 7.3 mmol) instead of 2-bromo-4,6-diphenylpyrimidine to obtain Compound 4-7 Yield: 74%).

Mass (theory: 575.20, measurement: 575 g / mol)

[Synthesis Example 48] Synthesis of Compound 4-8

The same procedure as in Synthesis Example 41 was repeated but using 2- (4-bromophenyl) triphenylene (2.8 g, 7.3 mmol) instead of 2-bromo-4,6-diphenylpyrimidine to obtain 4- 71%).

Mass (theory: 711.27, measurement: 711 g / mol)

[Synthesis Example 49] Synthesis of Compound 4-9

The same procedure as in Synthesis Example 41 was repeated but using 2-chloro-4-phenylquinazoline (1.8 g, 7.3 mmol) instead of 2-bromo-4,6-diphenylpyrimidine to obtain Compound 4-9 (2.7 g, yield 73 %).

Mass (theory: 613.23, measured: 613 g / mol)

[Synthesis Example 50] Synthesis of Compound 4-10

The same procedure as in Synthesis Example 41 was carried out except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (2.7 g, 7.3 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine To obtain Compound 4-10 (3.2 g, yield 72%).

Mass (theory: 739.27, found: 739 g / mol)

[Synthesis Example 51] Synthesis of Compound 5-1

2-bromo-4,6-diphenylpyrimidine (1.4 g, 4.7 mmol), CuI (0.1 g, 0.39 mmol), 1,10-phenanthroline (0.1 g, 0.78 mmol), Cs ₂ CO ₃ (2.5 g, 7.8 mmol) and nitrobenzene (30 ml) were mixed and stirred for 3 hours at 210 ° C. After completion of the reaction, the solid salt was filtered and purified by column chromatography To obtain Compound 5-1 (2.4 g, yield 70%).

Mass (theory: 866.34, measurement: 866 g / mol)

[Synthesis Example 52] Synthesis of Compound 5-2

The same procedure as in Preparation Example 51 was repeated but using 4-bromo-2,6-diphenylpyrimidine (1.4 g, 4.7 mmol) instead of 2-bromo-4,6-diphenylpyrimidine to obtain Compound 5-2 Yield: 68%).

Mass (theory: 866.34, measurement: 866 g / mol)

[Synthesis Example 53] Synthesis of Compound 5-3

The same procedure as in Preparation Example 51 was performed except that 2-chloro-4,6-diphenyl-1,3,5-triazine (1.2 g, 4.7 mmol) was used instead of 2-bromo-4,6-diphenylpyrimidine Compound 5-3 (2.5 g, yield 74%) was obtained.

Mass (theory: 867.34, measurement: 867 g / mol)

[Synthesis Example 54] Synthesis of Compound 5-4

Except that 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (1.8 g, 4.7 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine To obtain Compound 5-4 (2.6 g, yield 71%).

Mass (theory: 943.37, measurement: 943 g / mol)

[Synthesis Example 55] Synthesis of Compound 5-5

The same procedure as in Preparation Example 51 was repeated, except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (1.8 g, 4.7 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine Was performed to obtain Compound 5-5 (2.5 g, yield 70%).

Mass (theory: 943.37, measurement: 943 g / mol)

[Synthesis Example 56] Synthesis of Compound 5-6

The same procedure as in Preparation Example 51 was repeated but using 2- (3-bromophenyl) dibenzo [b, d] thiophene (1.6 g, 4.7 mmol) instead of 2-bromo-4,6-diphenylpyrimidine, 6 (2.4 g, yield 67%).

Mass (theory: 894.31, measurement: 894 g / mol)

[Synthesis Example 57] Synthesis of Compound 5-7

The same procedure as in Preparation Example 51 was repeated but using 2-bromodibenzo [b, d] furan (1.2 g, 4.7 mmol) instead of 2-bromo-4,6-diphenylpyrimidine to obtain Compound 5-7 Yield: 69%).

Mass (theory: 802.30, measured: 802 g / mol)

[Synthesis Example 58] Synthesis of Compound 5-8

The same procedure as in Preparation Example 51 was repeated but using 2- (4-bromophenyl) triphenylene (1.8 g, 4.7 mmol) instead of 2-bromo-4,6-diphenylpyrimidine to obtain Compound 5-8 72%).

Mass (theory: 938.37, measured: 938 g / mol)

[Synthesis Example 59] Synthesis of Compound 5-9

The same procedure as in Synthesis Example 51 was repeated but using 2-chloro-4-phenylquinazoline (1.1 g, 4.7 mmol) instead of 2-bromo-4,6-diphenylpyrimidine to obtain the compound 5-9 (2.4 g, yield 74 840.33%).

Mass (theory: measured: 840 g / mol)

[Synthesis Example 60] Synthesis of Compound 5-10

The same procedure as in Synthesis Example 51 was carried out except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (1.7 g, 4.7 mmol) was used in place of 2-bromo-4,6-diphenylpyrimidine To obtain Compound 5-10 (2.8 g, yield 75%).

Mass (theory: 966.37, found: 966 g / mol)

[Examples 1 to 48] Preparation of green organic electroluminescent device

The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was ultrasonically washed with distilled water. After the distilled water was washed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, and methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

M-MTDATA (60 nm) / TCTA (80 nm) / 90% on the prepared ITO transparent substrate (electrode) + 10% Ir (ppy) ₃ (30 nm) / BCP ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in this order.

[Comparative Example 1] Production of green organic electroluminescent device

A green organic electroluminescent device was fabricated in the same manner as in Example 1, except that CBP was used instead of Compound 1-1 as a luminescent host material in forming the light emitting layer.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , CBP and BCP used in Examples 1 to 48 and Comparative Example 2 are as follows.

[Evaluation Example 1]

The driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2 were measured for the green organic electroluminescent devices manufactured in Examples 1 to 48 and Comparative Example 1, and the results are shown in Table 1 below.

Sample Host The driving voltage (V) Emission peak (nm) Current efficiency (cd / A) Example 1 1-1 6.50 517 42.0 Example 2 1-2 6.60 518 41.9 Example 3 1-3 6.60 517 40.9 Example 4 1-4 6.55 516 40.8 Example 5 1-5 6.50 518 41.2 Example 6 1-6 6.45 518 40.5 Example 7 1-7 6.60 517 41.9 Example 8 1-8 6.70 517 41.1 Example 9 1-11 6.55 518 42.1 Example 10 1-12 6.60 518 41.8 Example 11 1-13 6.50 518 41.0 Example 12 1-14 6.55 516 40.8 Example 13 1-15 6.50 518 41.1 Example 14 1-16 6.55 518 40.9 Example 15 1-17 6.60 517 41.9 Example 16 1-18 6.65 518 41.1 Example 17 2-1 6.50 517 42.2 Example 18 2-2 6.50 518 41.7 Example 19 2-3 6.60 517 41.9 Example 20 2-4 6.55 516 40.8 Example 21 2-5 6.55 518 41.4 Example 22 2-6 6.45 518 40.5 Example 23 2-7 6.60 517 41.8 Example 24 2-8 6.60 517 41.2 Example 25 3-1 6.50 517 42.1 Example 26 3-2 6.55 518 41.8 Example 27 3-3 6.60 517 40.6 Example 28 3-4 6.55 516 41.8 Example 29 3-5 6.50 517 41.3 Example 30 3-6 6.60 518 42.5 Example 31 3-7 6.65 517 41.9 Example 32 3-8 6.45 517 41.1 Example 33 4-1 6.50 518 42.1 Example 34 4-2 6.60 517 41.5 Example 35 4-3 6.65 517 40.5 Example 36 4-4 6.55 516 40.4 Example 37 4-5 6.50 518 41.2 Example 38 4-6 6.45 517 40.5 Example 39 4-7 6.60 517 41.6 Example 40 4-8 6.50 517 41.4 Example 41 5-1 6.55 517 42.0 Example 42 5-2 6.60 518 41.9 Example 43 5-3 6.65 517 41.7 Example 44 5-4 6.50 516 40.8 Example 45 5-5 6.50 518 41.6 Example 46 5-6 6.45 518 40.5 Example 47 5-7 6.65 517 41.8 Example 48 5-8 6.55 517 41.3 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, when the compound of the present invention was used for the light emitting layer of the green organic electroluminescent device (Examples 1 to 48), the conventional CBP was used for the light emitting layer of the green organic electroluminescent device (Comparative Example 1) It was confirmed that the efficiency and the driving voltage were excellent.

[Examples 49 to 60] Preparation of red organic electroluminescent device

The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a red organic electroluminescent device was manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was ultrasonically washed with distilled water. After the distilled water was washed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, and methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

M-MTDATA (60 nm) / TCTA (80 nm) / 90% on the prepared ITO transparent pin (electrode) + host compound + 10% (piq) ₂ Ir (acac) (30 nm) / BCP ) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in this order.

[Comparative Example 2]

A red organic electroluminescent device was fabricated in the same manner as in Example 49, except that CBP was used instead of Compound 1-9 as a luminescent host material in forming the light emitting layer.

The structures of m-MTDATA, TCTA, CBP and BCP used in Examples 49 to 60 and Comparative Example 2 are as described above, and the structure of (piq) ₂ Ir (acac) is as follows.

[Evaluation Example 2]

The driving voltage and current efficiency at the current density of 10 mA / cm 2 were measured for the red organic electroluminescent devices prepared in Examples 49 to 60 and Comparative Example 2, and the results are shown in Table 2 below.

Sample Host The driving voltage (V) Current efficiency (cd / A) Example 49 1-9 4.80 12.5 Example 50 1-10 4.50 12.1 Example 51 1-19 4.70 12.4 Example 52 1-20 4.60 12.7 Example 53 2-9 4.60 12.0 Example 54 2-10 4.55 11.8 Example 55 3-9 4.75 12.2 Example 56 3-10 4.60 11.5 Example 57 4-9 4.80 12.0 Example 58 4-10 4.60 11.7 Example 59 5-9 4.90 12.3 Example 60 5-10 4.60 12.1 Comparative Example 2 CBP 5.25 8.2

As shown in Table 2, when the compound of the present invention was used for the light-emitting layer of the red organic electroluminescent device (Examples 49 to 60), compared with the case where the conventional CBP was used for the light-emitting layer of the red organic electroluminescent device (Comparative Example 2) It was confirmed that the efficiency and the driving voltage were excellent.

Claims (10)

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

In Formula 1,
Y ₁ to Y ₁₂ are each independently C (R ₁ ) or N, wherein Y ₁ and Y ₂ , Y ₂ and Y ₃ , Y ₃ and Y ₄ , Y ₅ and Y ₆ , Y ₆ and Y ₇ , Y ₇ and Y ₈ , Y ₉ and Y ₁₀ , Y ₁₀ and Y _11, and Y ₁₁ and Y ₁₂ are both C (R ₁ ), and are bonded to each other to form a condensed ring represented by the following formula (2)
(2)

In Formula 2,
The dotted line is a moiety bonded to the above formula (1)
In the above Formulas 1 and 2,
X ₁ and X ₂ are each independently selected from the group consisting of N (Ar ₁ ), O, S, C (Ar ₂ ) (Ar ₃ ) and Si (Ar ₄ ) (Ar ₅ ) N (Ar &_lt; ₁ &gt;),
Y ₁₃ to Y ₁₆ are each independently C (R ₂ ) or N,
Ar ₁ to Ar _{5 each} independently represent a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms A C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic group having 3 to 40 nuclear atoms alkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine of C ₆₀ A pentacene group, a pin oxide group, and an arylsilyl group of C ₆ to C ₆₀ ,
R ₁ and R ₂ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₁ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, C ₆ ~ aryl boronic of C _60, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of C ₆₀ aryl amine, or a, combination adjacent groups may form a fused ring,
The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group and arylsilyl group of Ar ₁ to Ar ₅ , R ₁ and R ₂ , An alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group and an arylamine group are each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkoxy group, group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 hetero cycloalkyl, heteroaryl of C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 aryl group, C ₁ ~ C ₄₀ alkyloxy A C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, C ₆ ~ C ₆₀ aryl phosphine group of, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C to 1 or more substituents selected from the ₆₀ group consisting of aryl amines may be unsubstituted or substituted have. The method according to claim 1,
Wherein the compound represented by the formula (1) is selected from the group consisting of compounds represented by the following formulas (3) to (11).
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

In the above formulas 3 to 11,
X ₁ , X ₂ , R _1, and R ₂ are the same as defined in claim ₁ , wherein the plurality of R _{1 s} are the same or different from each other, and the plurality of R _{2 s} are the same as or different from each other. The method according to claim 1,
Wherein the compound represented by the formula (1) is selected from the group consisting of compounds represented by the following formulas (12) to (20).
[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

[Chemical Formula 19]

[Chemical Formula 20]

In the above Formulas 12 to 20,
Ar _1, R ₁ and R ₂ are as defined in claim ₁ , wherein a plurality of R _{1 s} are the same as or different from each other, and a plurality of R _{2 s} are the same as or different from each other; The method according to claim 1,
Wherein Ar ₁ to Ar ₅ are each independently C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, a C ₆ ~ C ₆₀ aryl amine groups and consisting of C ₆ ~ C ₆₀ aryl silyl group of &Lt; / RTI &gt; The method according to claim 1,
R ₁ and R ₂ are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₆ to C ₆₀ aryl, heteroaryl having 5 to 60 nuclear atoms, A C ₆ to C ₆₀ arylamine group. The method according to claim 1,
And at least one of Ar ₁ , R ₁ and R ₂ is a substituent represented by the following formula (21).
[Chemical Formula 21]

In Formula 21,
L is selected from the group consisting of a single bond, an arylene group having ₆ to ₄₀ carbon atoms, a heteroarylene group having 5 to 40 nuclear atoms,
Z ₁ to Z ₅ are each independently N or C (R ₁₇ ), wherein at least one is N,
R ₁₇ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, a nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C ₄₀ of the, aryloxy of C ₆ ~ C ₆₀ , A C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl group selected from the group consisting of an amine or of a, it is possible to bond the adjacent group to form a condensed ring,
The L-arylene group, heteroarylene group, wherein R ₁₇ an alkyl group, an alkenyl group, an alkynyl group, an alkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group with siteul of, an aryloxy group, an alkylsilyl group, aryl silyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group, each independently, an alkenyl group of C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C _A C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkenyl group, C ₆ -C ₆₀ aryloxy groups, C ₁ -C ₄₀ alkylsilyl groups, C ₆ -C ₆₀ arylsilyl groups, C ₁ -C ₄₀ alkylboron groups, C ₆ -C ₆₀ the arylboronic group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide of the group and a C ₆ ~ value to one or more of the substituents selected from the group consisting of C ₆₀ arylamine Or it may be unsubstituted. The method according to claim 6,
Wherein the substituent represented by the formula (21) is selected from the group consisting of substituents represented by the following formulas (A-1) to (A-15).

In the above formulas A-1 to A-15,
L And R ₁₇ is as defined in claim 6, at which time, a plurality of R ₁₇ are the same or different from each other,
R ₂₁ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, aryloxy nuclear atoms 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C _60, alkyloxy group of C ₁ ~ C ₄₀ , An arylamine group of C ₆ to C ₆₀ , a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of C ₆₀ or aryl silyl, by combining groups of adjacent, may form a condensed ring,
Alkyl group of the R _21, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, the arylphosphine oxide group and the arylamine group are each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, alkyl, nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 of the heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C of ₆ ~ C ₆₀ aryl oxy group, C ₁ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic in, aryl of C ₆ ~ C ₆₀ phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl amines may be unsubstituted or substituted by one substituent at least one selected from the group consisting of,
n is an integer of 0 to 4; 1. An organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode,
Wherein at least one of the one or more organic layers includes the compound according to any one of claims 1 to 7. 9. The method of claim 8,
Wherein the organic compound layer containing the compound is selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron injecting layer, and a light emitting layer. 10. The method of claim 9,
The organic compound layer containing the compound is a light emitting layer,
Wherein the compound is a phosphorescent host of the light emitting layer.