KR101612154B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device including the organic electroluminescent device. The present invention relates to a novel organic compound and an organic electroluminescent device including the organic electroluminescent device with improved characteristics such as luminous efficiency, driving voltage, Device can be provided.

Description

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

The present invention relates to a novel organic compound that can be used as a material of an organic electroluminescent device, and an organic electroluminescent device including the same and having improved luminous efficiency, driving voltage, and life span of the device.

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

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

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

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

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

However, existing materials have an advantage in terms of luminescence properties, but their thermal stability is not very good due to their low glass transition temperature, so that they are not satisfactory in terms of lifetime in OLED devices. Therefore, development of materials with higher performance is required.

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

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

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

In Formula 1,

R ₂ and R ₃ , R ₃ and R ₄ or one of R ₄ and R ₅ is bonded to the following formula (2) to form a condensed ring,

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

X ₁ and X ₂ are the same or different and are each independently selected from O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and Si (Ar ₄₎ is selected from (Ar ₅₎ , At least one of X ₁ and X ₂ is N (Ar ₁ )

R ₁ to R ₉ and Ra are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ aryl An amino group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, is selected from the group consisting of a arylsilyl of C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ of which form a condensed ring by combining tile adjacent In addition,

n is an integer from 0 to 4,

Ar ₁ to Ar ₅ are the same or different and each independently represents 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 ₄₀ aryl group , A heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group , A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine is selected from the pingi, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ of the group consisting of aryl silyl,

In the above R ₁ to R _9, Ra and Ar ₁ to Ar ₅ , 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 ₄₀ aryl group , A heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group , A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine The pinning group, C ₆ -C ₄₀ arylphosphine oxide group and C ₆ -C ₄₀ arylsilyl group are each independently selected from the group consisting of deuterium, halogen, cyano group, C ₁ -C ₄₀ alkyl group, C ₂ -C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, C ₆ ~ C _40, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a 3 to 40 nuclear atoms of a heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, a alkyl boronic of C ₁ ~ C _40, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of the C ₄₀ group And an arylsilyl group having from ₆ to ₄₀ carbon atoms. Here, when a plurality of substituents are present, a plurality of substituents may be the same or different.

Also, the present invention is an organic electroluminescent device comprising a cathode, 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 a compound of the above formula And an organic electroluminescent device.

At least one of the one or more organic layers may be selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection 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 compound represented by the general formula (1) of the present invention is excellent in thermal stability and phosphorescence properties and can be used as a material for an organic material layer of an organic electroluminescent device. In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host material, it is possible to produce an organic electroluminescent device having excellent light emitting performance, low driving voltage, high efficiency, and long life time as compared with conventional host materials, And a full color display panel in which the lifetime is greatly improved can also be manufactured.

Hereinafter, the present invention will be described in detail.

<Novel compound>

The novel compound according to the present invention has a structure in which an indole moiety is fused to the terminal of an imidazoindole moiety to form a basic skeleton and various substituents are bonded to the basic skeleton. Is displayed.

The compound represented by Formula 1 has a broad band gap due to an indole moiety bonded to the terminal of an imidazoindole moiety and also has a large number of molecules due to various aromatic ring substituents. bipolar) characteristics, and the bonding strength between holes and electrons can be increased. Therefore, it is possible to improve the phosphorescence characteristic of the organic EL device and improve the hole injecting ability, transporting ability, or light emitting efficiency.

Further, since the aromatic ring substituent introduced into the indole moiety significantly increases the molecular weight of the compound, the glass transition temperature can be improved, and thus, the conventional CBP (4,4-dicarbazolylbiphenyl) It can have higher thermal stability.

In addition, the indole moiety bonded to the end of the indole indole moiety is fused with the indole moiety to improve the thermal stability of the compound and to inhibit the crystallization of the organic layer. Therefore, the organic EL device including the compound of Formula 1 according to the present invention can greatly improve durability and lifetime characteristics.

Specifically, when the compound represented by the formula (1) of the present invention is used as a blue, green and / or red phosphorescent host material as a material for a positive hole injection / transport layer of an organic EL device, the efficiency and life Excellent effect can be exhibited. Therefore, the compound represented by the general formula (1) of the present invention can greatly contribute to improvement of the performance and lifetime of the organic EL device, and the lifetime of the organic EL device can be maximized in the full color organic light emitting panel.

The compound represented by the formula (1) of the present invention in which a condensed ring is formed in combination with the formula (2) may be further represented by a compound represented by any one of the following formulas (3) to (8). The compounds represented by the formulas (3) to (8) are preferable in consideration of the characteristics of the organic EL device.

In the above Formulas 3 to 8,

X ₁ , X _2, R ₁ to R ₉ , Ra, Ar ₁ to Ar ₅ and n are as defined above.

More specifically, X ₁ and X ₂ are each independently selected from O, S, Se, N (Ar ₁ ), C (Ar ₂ ) (Ar ₃ ) and Si (Ar ₄ ) (Ar ₅ ) ₁ and X &lt; ₂ &gt; is N (Ar &_lt; ₁ &gt;). Preferably, both X ₁ and X ₂ are N (Ar ₁ ). When X ₁ and X ₂ are N (Ar ₁ ), each Ar ₁ is the same or different.

Ar ₁ to Ar ₅ are the same or different and each independently represents 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 ₄₀ An 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 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ an aryl phosphine group, and is selected from the group consisting of C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl group in the silyl.

When considering the characteristics of the organic EL device, the above Ar ₁ to Ar ₅ may be the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₄₀ aryl group or a substituted or unsubstituted nuclear atom More preferably 5 to 40 heteroaryl groups.

Further, R ₁ to R ₉ , Ra in which at least one of R ₂ and R ₃ , R ₃ and R ₄ , and / or R ₄ and R ₅ are excluded is a substituent which does not form a condensed ring with the formula (2) be the same or different and are each independently hydrogen, deuterium, halogen, cyano, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₆ ~ C ₄₀ the aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ arylamine group of C _40, C ₃ ~ C ₄₀ A cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ aralkyl group, An arylphosphine group of C ₆ to C ₄₀ , an arylphosphine oxide group of C ₆ to C ₄₀ , and an arylsilyl group of C ₆ to C ₄₀ , which may be bonded to adjacent groups to form a condensed ring.

In the present invention, R ₁ to R ₉ and Ra each independently represent hydrogen, deuterium (D), a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl having 5 to 40 nucleus And a substituted or unsubstituted C ₆ to C ₄₀ arylamine group.

In the above R ₁ to R _9, Ra and Ar ₁ to Ar ₅ , an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocyclo An alkyl group, an alkylsilyl group, an alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group and an arylsilyl group are each independently selected from the group consisting of deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ A C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyl oxy group, C ₆ ~ C ₄₀ aryl amine group, a C ₃ ~ C ₄₀ cycloalkyl group, the nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, an alkyl of C ₁ ~ C ₄₀ boron group, C ₆ ~ C ₄₀ aryl group of boron, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl group selected from the group consisting of a silyl It may be substituted with at least one member. When there are a plurality of substituents, the plurality of substituents may be the same as or different from each other.

In the compound of formula (I) according to the present invention, R ₁ to R ₁₁ and Ra and Ar ₁ to Ar ₅ are each independently preferably selected from the group consisting of hydrogen or the substituents represented by the following S1 to S204, Do not.

More preferably, R ₁ to R ₁₁ and Ra and Ar ₁ to Ar ₅ each independently may be selected from hydrogen or the following substituent group.

The compounds of the present invention described above can be further exemplified by the following exemplified structures. However, the compounds represented by formula (1) of the present invention are not limited by the following examples.

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

The "alkenyl" in the present invention is 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 vinyl, allyl allyl, isopropenyl, 2-butenyl, and the like.

"Alkynyl" in the present invention 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.

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 phenyl, naphthyl, phenanthryl, anthryl and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 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. In addition, it is understood that a form in which two or more rings are pendant or condensed with each other may be included, and further includes a condensed form with an aryl group. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, 2-furanyl, N-imidazolyl, 2- isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like.

In the present invention, "aryloxy" means a monovalent substituent represented by RO-, and R represents aryl having 5 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.

The term "alkyloxy" in the present invention means a monovalent substituent group represented by R'O-, wherein R 'represents 1 to 40 alkyl, and may have a linear, branched or cyclic structure . Examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

"Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

"Cycloalkyl" in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

"Heterocycloalkyl" in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon, preferably 1 to 3 carbons, of the ring is replaced by N, O, S or Se. &Lt; / RTI &gt; Examples of such heterocycloalkyl include morpholine, piperazine and the like.

"Alkylsilyl" in the present invention means a silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 40 carbon atoms.

In the present invention, the term "condensed rings" means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.

The compounds of formula (1) of the present invention can be synthesized in various ways with reference to the following Synthesis Examples. 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 of the present invention includes an anode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, A compound represented by the formula (1), preferably a compound represented by the formula (3) to (8). At this time, the compound of formula (1) may be used alone or in combination of two or more.

The one or more organic layers may be at least one of a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer, and at least one of the organic layers may include a compound represented by Formula 1. [ At this time, it is preferable that the organic material layer including the compound of Formula 1 is a light emitting layer.

Specifically, the light emitting layer of the organic electroluminescent device of the present invention may include a host material, which may include the compound of Formula 1 as a host material. When the compound of Formula 1 is included in the light emitting layer material of the organic electroluminescent device, preferably blue, green, and red phosphorescent host materials, the bonding strength between holes and electrons in the light emitting layer increases, Efficiency (luminous efficiency and power efficiency), lifetime, luminance, driving voltage, and the like can be improved.

The structure of the organic electroluminescent device according to the present invention is not particularly limited and may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially laminated. 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 . Specifically, the compound represented by the general formula (1) of the present invention can be used as a phosphorescent host material in the light emitting layer. On the other hand, an electron injection layer may be further stacked on the electron transport layer.

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

The organic electroluminescent device according to the present invention may be formed by using materials and methods known in the art, except that at least one of the organic material layers (for example, the light emitting layer) An organic material layer and an electrode.

The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

The substrate usable in the present invention is not particularly limited, and a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet can be used.

Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.

The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or an alloy thereof; And multi-layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

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 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 IIC-1

<Step 1> Synthesis of 5- (3-bromo-2-nitrophenyl) -1,2-diphenyl-1H-imidazole

11.85 g (39.6 mmol) of 5-bromo-1,2-diphenyl-1H-imidazole and 11.68 g (47.5 mmol) of 3-bromo-2-nitrophenylboronic acid, 4.75 g (118.8 mmol) ml / 100 ml of THF / H ₂ O were added and stirred. At 40 ℃ into the Pd (PPh _{3) 4} of 2.29 g (5 mol%) was stirred for 2 h at 80 ℃. 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, 11.15 g (26.5 mmol, yield: 67%) of 5- (3-bromo-2-nitrophenyl) -1,2- diphenyl-1H- imidazole .

^{1 H-NMR: δ 7.43 (} m, 2H), 7.55 (m, 6H), 7.64 (s, 1H), 7.86 (m, 3H), 8.24 (d, 2H)

<Step 2> Synthesis of 5-bromo-1,2-diphenyl-1,4-dihydroimidazo [4,5-b] indole

9.12 g (21.7 mmol) of 5- (3-bromo-2-nitrophenyl) -1,2-diphenyl-1H-imidazole, 14.2 g (54.2 mmol) of triphenylphosphine and 100 ml of 1,2- dichlorobenzene were placed under a nitrogen stream, Lt; / RTI &gt; 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 5.75 g of the target compound 5-bromo-1,2-diphenyl-1,4-dihydroimidazo [4,5-b] indole, , yield: 68%).

¹ H-NMR:? 7.22 (t, 1 H), 7.43 (m, 3H), 7.54 (m, 6H), 8.04 (d,

<Step 3> Synthesis of 5-bromo-1,2,4-triphenyl-1,4-dihydroimidazo [4,5-b] indole

5.5 g (14.2 mmol) of indole 5-bromo-1,2-diphenyl-1,4-dihydroimidazo [4,5-b] indole, iodobenzene (5.79 g, 28.4 mmol) and Cu powder (0.1 g, ), K ₂ CO ₃ (1.96 g, 14.2 mmol), Na ₂ SO ₄ (2.02 g, 14.2 mmol) and nitrobenzene (100 ml) were mixed and stirred at 210 ° C for 12 hours.

After completion of the reaction, the nitrobenzene was removed. The organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removal of the solvent from the organic layer from which water had been removed, the residue was purified by column chromatography to obtain 4.88 g (10.5 mmol, yield: 74%) of 5-bromo-1,2,4-triphenyl-1,4-dihydroimidazo [ %).

^{1 H-NMR: δ 7.21 (} m, 2H), 7.44 (m, 3H), 7.54 (m, 10H), 8.25 (d, 2H), 8.63 (d, 1H)

<Step 4> Synthesis of 5- (2-nitrophenyl) -1,2,4-triphenyl-1,4-dihydroimidazo [4,5-b] indole

2-nitrophenylboronic acid and 1.26 g (31.5 mmol) of NaOH and 2.1 g (12.6 mmol) of 5-bromo-1,2-diphenyl-1H-imidazole and 100 ml / 50 ml Of THF / H ₂ O were added and stirred. At 40 ℃ 0.61 g (5 mol% ) into the Pd (PPh _{3) 4} was stirred for 2 h at 80 ℃. 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, 4.63 g (9.14 mmol) of the desired compound 5- (2-nitrophenyl) -1,2,4-triphenyl-1,4-dihydroimidazo [4,5- mmol, yield: 87%).

¹ H-NMR: 8 7.31 (t, 1 H), 7.44 (m, 3H), 7.56 (m, 10H), 7.67 d, 1 H)

<Step 5> Synthesis of IIC-1

Substituting 5- (2-nitrophenyl) -1,2,4-triphenyl-1,4-dihydroimidazo [4,5-b] pyridine instead of 5- (3-bromo- 3.30 g (6.95 mmol, yield: 76%) of the desired compound IIC-1 was obtained by carrying out the same procedure as <Step 2> of Preparation Example 1, except that indole 4.63 g (9.14 mmol)

^{1 H-NMR: δ 7.31 (} t, 1H), 7.45 (m, 3H), 7.54 (m, 12H), 7.64 (d, 1H), 8.12 (d, 1H), 8.28 (d, 2H), 8.48 ( d, 1 H), 11.21 (s, 1 H)

[Preparation Example 2] Synthesis of IIC-2 and IIC-3

<Step 1> Synthesis of 5- (4-bromo-2-nitrophenyl) -1,2-diphenyl-1H-imidazole

The procedure of Step 1 of Preparation Example 1 was repeated except that 11.68 g (47.5 mmol) of 4-bromo-2-nitrophenylboronic acid was used in place of 3-bromo-2-nitrophenylboronic acid to obtain 5- (4 -bromo-2-nitrophenyl) -1,2-diphenyl-1H-imidazole (27.5 mmol, yield: 69%).

^{1 H-NMR: δ 7.42 (} m, 2H), 7.55 (m, 6H), 7.65 (s, 1H), 7.99 (m, 2H), 8.28 (d, 2H), 8.62 (s, 1H)

<Step 2> Synthesis of 6-bromo-1,2-diphenyl-1,4-dihydroimidazo [4,5-b] indole

9.12 g (21.7 mmol) of 5- (4-bromo-2-nitrophenyl) -1,2-diphenyl-1H-imidazole was used instead of 5- (3-bromo-2-nitrophenyl) The procedure of Step 2 of Preparation Example 1 was repeated to obtain 5.90 g (15.2 mmol) of 6-bromo-1,2-diphenyl-1,4-dihydroimidazo [4,5- , yield: 70%).

¹ H-NMR:? 7.40 (m, 3H), 7.55 (m, 7H), 7.99

<Step 3> Synthesis of 6-bromo-1,2,4-triphenyl-1,4-dihydroimidazo [4,5-b] indole

5.5 g of 6-bromo-1,2-diphenyl-1,4-dihydroimidazo [4,5-b] indole was used instead of 5-bromo-1,2-diphenyl-1,4-dihydroimidazo [ 4-triphenyl-1,4-dihydroimidazo [4,5-b] pyridine was prepared by following the procedure of Step 3 of Preparation Example 1, 5.14 g (11.1 mmol, yield: 78%) of indole were obtained.

¹ H-NMR:? 7.19 (d, 1 H), 7.45 (m, 3H), 7.58 (m,

<Step 4> Synthesis of 6- (2-nitrophenyl) -1,2,4-triphenyl-1,4-dihydroimidazo [4,5-b] indole

Except that 4.88 g (10.5 mmol) of 6-bromo-1,2,4-triphenyl-1,4-dihydroimidazo [4,5-b] indole was used instead of 5-bromo-1,2-diphenyl- 4-dihydroimidazo [4,5-b] indole was obtained by carrying out the same procedure as in the step 4 of Preparation Example 1 to obtain 4.63 g of (6- (2-nitrophenyl) -1,2,4-triphenyl- 9.14 mmol, yield: 87%).

^{1 H-NMR: δ 7.42 (} m, 3H), 7.57 (m, 10H), 7.63 (m, 2H), 8.02 (. M 3H), 8.27 (d, 2H), 8.49 (s, 1H)

<Step 5> Synthesis of IIC-2 and IIC-3

Instead of 6- (2-nitrophenyl) -1,2,4-triphenyl-1,4-dihydroimidazo [4,5- The procedure of Step 5 of Preparation Example 1 was repeated except that 4.63 g (9.14 mmol) of dihydroimidazo [4,5-b] indole was used, yielding 1.56 g (3.29 mmol, yield: 36 %) And 1.43 g (3.02 mmol, yield: 33%) of IIC-3.

Of ^{IIC-2 1 H-NMR:} δ 7.30 (t, 1H), 7.43 (m, 3H), 7.55 (m, 11H), 7.63 (d, 1H), 7.89 (d, 1H), 8.12 (d, 1H ), 8.27 (d, 2H), 8.43 (d, IH), 10.22 (s, IH)

¹ of the IIC-3 H-NMR: δ 7.30 (t, 1H), 7.44 (m, 4H), 7.54 (m, 12H), 7.63 (d, 1H), 8.12 (d, 1H), 8.28 (d, 2H ), 10.21 (s, 1 H)

[Preparation Example 3] Synthesis of IIC-4 and IIC-5

<Step 1> Synthesis of 5- (5-bromo-2-nitrophenyl) -1,2-diphenyl-1H-imidazole

The procedure of Step 1 of Preparation Example 1 was repeated except that 11.68 g (47.5 mmol) of 5-bromo-2-nitrophenylboronic acid was used in place of 3-bromo-2-nitrophenylboronic acid to obtain 5- (5 -bromo-2-nitrophenyl) -1,2-diphenyl-1H-imidazole 11.3 g (26.9 mmol, yield: 68%).

^{1 H-NMR: δ 7.42 (} m, 2H), 7.53 (m, 6H), 7.65 (s, 1H), 7.76 (s, 1H), 7.99 (d, 1H), 8.24 (m, 3H)

<Step 2> Synthesis of 7-bromo-1,2-diphenyl-1,4-dihydroimidazo [4,5-b] indole

9.12 g (21.7 mmol) of 5- (5-bromo-2-nitrophenyl) -1,2-diphenyl-1H-imidazole was used instead of 5- (3-bromo-2-nitrophenyl) 6.15 g (15.9 mmol) of 7-bromo-1,2-diphenyl-1,4-dihydroimidazo [4,5-b] indole were obtained by carrying out the same processes as in <Step 2> of Preparation Example 1, , yield: 73%).

¹ H-NMR:? 7.42 (m, 3H), 7.55 (m, 7H), 7.99

<Step 3> Synthesis of 7-bromo-1,2,4-triphenyl-1,4-dihydroimidazo [4,5-b] indole

5.5 g of 7-bromo-1,2-diphenyl-1,4-dihydroimidazo [4,5-b] indole was used instead of 5-bromo-1,2-diphenyl-1,4-dihydroimidazo [ 4-triphenyl-1,4-dihydroimidazo [4,5-b] pyridine was prepared by following the procedure of Step 3 of Preparation Example 1, indole 4.94 g (10.7 mmol, yield: 75%).

^{1 H-NMR: δ 7.25 (} d, 1H), 7.44 (m, 3H), 7.54 (m, 10H), 7.79 (d, 2H), 8.27 (d, 2H)

<Step 4> Synthesis of 7- (2-nitrophenyl) -1,2,4-triphenyl-1,4-dihydroimidazo [4,5-b] indole

Except that 4.88 g (10.5 mmol) of 7-bromo-1,2,4-triphenyl-1,4-dihydroimidazo [4,5-b] indole was used instead of 5-bromo-1,2-diphenyl- 4-dihydroimidazo [4,5-b] indole was obtained by carrying out the same procedure as Step 4 of Preparation Example 1 with the exception of using 4.63 g of (2-nitrophenyl) -1,2,4-triphenyl- 9.14 mmol, yield: 87%).

^{1 H-NMR: δ 7.45 (} m, 3H), 7.54 (m, 10H), 7.72 (m, 2H), 7.99 (m, 4H), 8.18 (d, 1H), 8.27 (d, 2H)

<Step 5> Synthesis of IIC-4 and IIC-5

Instead of 7- (2-nitrophenyl) -1,2,4-triphenyl-1,4-dihydroimidazo [4,5- The procedure of Step 5 of Preparation Example 1 was repeated except that 4.63 g (9.14 mmol) of dihydroimidazo [4,5-b] indole was used, yielding 1.48 g (3.11 mmol, yield: 34 %) And 1.73 g (3.66 mmol, yield: 40%) of IIC-5.

¹ H-NMR of IIC-4: 8 7.30 (t, 1H), 7.43 (m, 4H), 7.53 (m, 12H), 7.63 (d, ), 10.21 (s, 1 H)

Of ^{IIC-5 1 H-NMR:} δ 7.29 (t, 1H), 7.44 (m, 3H), 7.55 (m, 11H), 7.63 (d, 1H), 7.96 (m, 2H), 8.12 (d, 1H ), 8.27 (d, 2H), 10.22 (s, 1 H)

[Preparation Example 4] Synthesis of IIC-6

<Step 1> Synthesis of 5- (2-bromo-6-nitrophenyl) -1,2-diphenyl-1H-imidazole

The same procedure as in <Step 1> of Preparation Example 1 was carried out except that 11.68 g (47.5 mmol) of 2-bromo-6-nitrophenylboronic acid was used in place of 3-bromo-2-nitrophenylboronic acid to obtain 5- (2 -bromo-6-nitrophenyl) -1,2-diphenyl-1H-imidazole 11.3 g (26.9 mmol, yield: 68%).

^{1 H-NMR: δ 7.42 (} m, 2H), 7.55 (m, 7H), 7.65 (s, 1H), 7.99 (m, 2H), 8.27 (d, 2H)

<Step 2> Synthesis of 8-bromo-1,2-diphenyl-1,4-dihydroimidazo [4,5-b] indole

9.12 g (21.7 mmol) of 5- (2-bromo-6-nitrophenyl) -1,2-diphenyl-1H-imidazole was used instead of 5- (3-bromo- Bromo-1,2-diphenyl-1,4-dihydroimidazo [4,5-b] indole was obtained in the same manner as in <Step 2> of Preparation Example 1, , yield: 70%).

^{1 H-NMR: δ 7.27 (} t, 1H), 7.33 (d, 1H), 7.42 (m, 2H), 7.56 (m, 7H), 8.27 (d, 2H), 11.32 (s, 1H)

<Step 3> Synthesis of 8-bromo-1,2,4-triphenyl-1,4-dihydroimidazo [ 4,5-b] indole

Instead of 5-bromo-1,2-diphenyl-1,4-dihydroimidazo [4,5-b] Bromo-1,2,4-triphenyl-1,4-dihydroimidazo [4,5-b] pyridine was prepared by following the procedure of Step 3 of Preparation Example 1, indole 4.94 g (10.7 mmol, yield: 75%).

^{1 H-NMR: δ 7.17 (} d, 1H), 7.23 (t, 1H), 7.44 (m, 3H), 7.54 (m, 10H), 7.88 (d, 1H), 8.27 (d, 2H)

<Step 4> Synthesis of 8- (2-nitrophenyl) -1,2,4-triphenyl-1,4-dihydroimidazo [4,5-b] indole

Except that 4.88 g (10.5 mmol) of 8-bromo-1,2,4-triphenyl-1,4-dihydroimidazo [4,5-b] indole was used instead of 5-bromo-1,2-diphenyl- (2-nitrophenyl) -1,2,4-triphenyl-1,4-dihydroimidazo [4,5-b] indole in the same manner as in Step 4 of Preparation Example 1 9.25 mmol, yield: 88%).

^{1 H-NMR: δ 7.38 (} t, 1H), 7.43 (m, 3H), 7.55 (m, 10H), 7.67 (t, 1H), 7.98 (m, 5H), 8.28 (d, 2H)

<Step 5> Synthesis of IIC-6

Instead of 8- (2-nitrophenyl) -1,2,4-triphenyl-1,4-dihydroimidazo [4,5- The procedure of Step 5 of Preparation Example 1 was repeated except that 4.63 g (9.14 mmol) of dihydroimidazo [4,5-b] indole was used to yield 2.95 g (6.22 mmol, yield: 68 %).

^{1 H-NMR: δ 7.28 (} t, 1H), 7.43 (m, 3H), 7.56 (m, 11H), 7.63 (m, 1H), 7.94 (d, 1H), 8.12 (d, 1H), 8.28 ( d, 2 H), 11.21 (s, 1 H)

[Preparation Example 5] Synthesis of IIC-7 and IIC-8

<Step 1> Synthesis of 7- (2-nitrophenyl) -1,2-diphenyl-1,4-dihydroimidazo [4,5-b] indole

Except that 4.08 g (10.5 mmol) of 7-bromo-1,2-diphenyl-1,4-dihydroimidazo [4,5-b] indole was used instead of 5-bromo-1,2-diphenyl- , 4.11 g (9.56 mmol, yield) of 7- (2-nitrophenyl) -1,2-diphenyl-1,4-dihydroimidazo [4,5- b] indole were obtained in the same manner as in <Step 4> : 91%).

^{1 H-NMR: δ 7.43 (} m, 2H), 7.55 (m, 6H), 7.68 (m, 3H), 7.89 (m, 2H), 8.02 (m, 2H), 8.27 (d, 2H)

Step 2: Synthesis of 4- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl-7- (2-nitrophenyl) -1,2-diphenyl-1,4-dihydroimidazo Synthesis of [4,5-b] indole

A solution of 6.11 g (14.2 mmol) of 7- (2-nitrophenyl) -1,2-diphenyl-1,4-dihydroimidazo [4,5- b] indole, 2- (3-bromophenyl) (1.0 g, 1.42 mmol), K ₂ CO ₃ (1.96 g, 14.2 mmol), Na ₂ SO ₄ (2.02 g, 14.2 mmol) nitrobenzene (100 ml) were mixed and stirred at 210 캜 for 12 hours.

After completion of the reaction, the nitrobenzene was removed. The organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removal of the solvent from the organic layer from which the water had been removed, the residue was purified by column chromatography to obtain 4- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl- -1,2-diphenyl-1,4-dihydroimidazo [4,5-b] indole were obtained in a yield of 69%.

^{1 H-NMR: δ 7.43 (} m, 5H), 7.56 (m, 11H), 7.68 (m, 2H), 7.89 (d, 1H), 8.01 (m, 4H), 8.27 (m, 8H)

<Step 3> Synthesis of IIC-7 and IIC-8

Instead of 4- (3- (4,6-diphenyl-1,3,5-triazin-1-yl) -1,2,4-triphenyl-1,4- dihydroimidazo [4,5- 2-yl) phenyl) -7- (2-nitrophenyl) -1,2-diphenyl-1,4-dihydroimidazo [4,5- b] indole. 2.39 g (3.38 mmol, yield: 37%) of IIC-7 and 2.58 g (3.66 mmol, yield: 40%) of IIC-8 were obtained in the same manner as in step 1 of Example 1.

¹ H-NMR of the IIC-7: δ 7.29 (t , 1H), 7.44 (m, 6H), 7.53 (m, 13H), 7.63 (d, 1H), 8.09 (m, 2H), 8.27 (m, 7H ), 11.22 (s, 1 H)

Of ^{IIC-8 1 H-NMR:} δ 7.29 (t, 1H), 7.45 (m, 5H), 7.52 (m, 12H), 7.63 (d, 1H), 7.99 (m, 3H), 8.12 (d, 1H ), 8.28 (m, 7 H), 11.22 (s, 1 H)

[Synthesis Example 1] Synthesis of Inv-1

(3 g, 6.32 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (2.61 g, 7.59 mmol), Pd (OAc) ₂ g, 5 mol%), NaO (t-bu) (1.52 g, 15.80 mmol), P (t-bu) 3 (0.13 g, 0.63 mmol) and a mixture of Toluene (100 ml) and for 12 hours at 110 ℃ Lt; / RTI &gt;

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 2: 1 (v / v)) to obtain Inv-1 (3.36 g, yield 68%) .

GC-Mass (theory: 781.30 g / mol, measured: 781 g / mol)

[Synthesis Example 2] Synthesis of Inv-2

(3 g, 6.32 mmol), 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (4.40 g, 9.48 mmol), Cu powder 0.02 g, 0.63 mmol), K ₂ CO ₃ (0.87 g, 6.32 mmol), Na ₂ SO ₄ (0.90 g, 6.32 mmol) and nitrobenzene (100 ml) were mixed and stirred at 200 ° C for 24 hours.

After completion of the reaction, the nitrobenzene was removed. The organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent was removed from the organic layer from which water had been removed and then purified by column chromatography (Hexane: MC = 1: 1 (v / v)) to obtain Inv-2 (2.82 g, yield 52%).

GC-Mass (calculated: 857.33 g / mol, measured: 857 g / mol)

[Synthesis Example 3] Synthesis of Inv-3

3, 5-triazine (3.19 g, 7.59 mmol), Pd (OAc) ₂ (3 g, 6.32 mmol) (0.07 g, 5 mol%) , NaO (t-bu) (1.52 g, 15.80 mmol), P (t-bu) 3 (0.13 g, 0.63 mmol) and Toluene (100 ml) using the above synthesis example 1 The target compound Inv-3 (3.80 g, yield 70%) was obtained.

GC-Mass (calculated: 857.33 g / mol, measured: 857 g / mol)

[Synthesis Example 4] Synthesis of Inv-4

Pd (OAc) ₂ (0.07 g, 5 mol%), NaO (t-Butylpyridine) (2.59 g, 7.59 mmol) bu) (1.52 g, 15.80 mmol ), P (t-bu) 3 (0.13 g, 0.63 mmol) and Toluene (100 ml), the above synthesis example 1, the same way the desired compound Inv-4 (3.20 g as and using , Yield 65%).

GC-Mass (calculated: 779.30 g / mol, measured: 779 g / mol)

[Synthesis Example 5] Synthesis of Inv-5

3-iodo-9-phenyl-9H-carbazole (3.50 g, 9.48 mmol), Cu powder (0.04 g, 0.63 mmol), K ₂ CO ₃ (0.87 g, 6.32 mmol) _{), Na 2 SO 4 (0.90} g, using 6.32 mmol), nitrobenzene (100 ml ), to obtain the desired compound of Inv-5 (2.17 g, yield 48%) in the same manner as in synthesis example 2.

GC-Mass (calculated: 715.27 g / mol, measured: 715 g / mol)

[Synthesis Example 6] Synthesis of Inv-6

(0.90 g, 0.63 mmol), K ₂ CO ₃ (0.87 g, 6.32 mmol), Na ₂ SO ₄ (0.90 g, 0.63 mmol), Iodobenzene (1.93 g, 6.32 mmol) and nitrobenzene (100 ml), Inv-6 (1.88 g, yield 54%) was obtained in the same manner as in Synthesis Example 2. [

GC-Mass (calculated: 550.22 g / mol, measured: 550 g / mol)

[Synthesis Example 7] Synthesis of Inv-7

Cu powder (0.04 g, 0.63 mmol), K ₂ CO ₃ (0.87 g, 6.32 mmol), IIC-2 (3 g, 6.32 mmol), 6-bromo-2,3'-bipyridine (2.23 g, 9.48 mmol) , Na ₂ SO ₄ using a (0.90 g, 6.32 mmol), nitrobenzene (100 ml), to obtain the desired compound of Inv-7 (1.95 g, yield: 49%) in the same manner as in synthesis example 2.

GC-Mass (calculated: 628.24 g / mol, measured: 628 g / mol)

[Synthesis Example 8] Synthesis of Inv-8

(0.07 g, 0.63 mmol), K ₂ CO ₃ (0.87 g, 6.32 mmol), Na ₂ SO ₄ (0.90 g, 0.63 mmol), IIC-2 (3 g, 6.32 mmol), 2-bromoquinoline g, 6.32 mmol) and nitrobenzene (100 ml), the target compound Inv-8 (1.71 g, yield 45%) was obtained in the same manner as in Synthesis Example 2. [

GC-Mass (theory: 601.23 g / mol, measurement: 601 g / mol)

[Synthesis Example 9] Synthesis of Inv-9

Cu powder (0.04 g, 0.63 mmol), K ₂ CO ₃ (0.87 g, 6.32 mmol), IIC-2 (3 g, 6.32 mmol), 4-bromo- N, N diphenylaniline (3.07 g, 9.48 mmol) Na ₂ SO ₄ using a (0.90 g, 6.32 mmol), nitrobenzene (100 ml), was obtained in Inv-9 (2.09 g, yield 46%) of the target compound in the same manner as in synthesis example 2.

GC-Mass (calculated: 717.29 g / mol, measured: 717 g / mol)

[Synthesis Example 10] Synthesis of Inv-10

Cu powder (0.04 g, 0.63 mmol), K ₂ CO ₃ (0.87 g, 6.32 mmol), 2-bromo-4,6-diphenylpyridine (2.94 g, 9.48 mmol), IIC- Na ₂ SO ₄ using a (0.90 g, 6.32 mmol), nitrobenzene (100 ml), to obtain the desired compound of Inv-10 (2.14 g, yield 48%) in the same manner as in synthesis example 2.

GC-Mass (calculated: 703.27 g / mol, measured: 703 g / mol)

[Synthesis Example 11] Synthesis of Inv-11

Pd (OAc) ₂ (0.07 g, 5 mol%), NaO (t-Bu) (1.52 mmol) was added to a solution of 2-chloro-4,6-diphenylpyrimidine (2.02 g, 7.59 mmol) 11 (2.63 g, yield 59%) was obtained in the same manner as in Synthesis Example 1, except that P (t-bu) ₃ (0.13 g, 0.63 mmol) and Toluene ).

GC-Mass (calculated: 704.27 g / mol, measured: 704 g / mol)

[Synthesis Example 12] Synthesis of Inv-12

Cu powder (0.04 g, 0.63 mmol), K ₂ CO ₃ (0.87 g, 6.32 mmol), Na (3-bromophenyl) pyridine (2.22 g, 9.48 mmol), IIC- Inv-12 (1.79 g, yield 45%) was obtained in the same manner as in Synthesis Example 2, using _2- SO ₄ (0.90 g, 6.32 mmol) and nitrobenzene (100 ml).

GC-Mass (calculated: 627.24 g / mol, measured: 627 g / mol)

[Synthesis Example 13] Synthesis of Inv-13

0.23 g (9.48 mmol) of NaH under nitrogen was added to 50 ml of DMF and stirred. 3 g (6.32 mmol) of IIC-3 dissolved in 50 ml of DMF was slowly added thereto, followed by stirring for about 1 hour. Then 2.54 g (9.48 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine dissolved in 100 ml of DMF was added slowly and stirred for 12 hours. After completion of the reaction, the mixture was filtered through silica, washed with water and methanol, and then the solvent was removed to obtain the target compound Inv-13 (3.26 g, yield 73%).

GC-Mass (calculated: 705.26 g / mol, measured: 705 g / mol)

[Synthesis Example 14] Synthesis of Inv-14

IIC-3 (3 g, 6.32 mmol), 3-bromobiphenyl (2.21 g, 9.48 mmol), Cu powder (0.04 g, 0.63 mmol), K 2 CO 3 (0.87 g, 6.32 mmol), Na 2 SO 4 (0.90 g, 6.32 mmol) and nitrobenzene (100 ml) were used to obtain Inv-14 (1.62 g, yield 41%) in the same manner as in Synthesis Example 2. [

GC-Mass (calculated: 626.25 g / mol, measured: 626 g / mol)

[Synthesis Example 15] Synthesis of Inv-15

(0.87 g, 6.32 mmol), Cu powder (0.04 g, 0.63 mmol), I ₂ CO ₃ (3 g, 6.32 mmol), 5-bromo-2,2'-bipyridine (2.23 g, 9.48 mmol) , Na ₂ SO ₄ using a (0.90 g, 6.32 mmol), nitrobenzene (100 ml), to obtain the desired compound of Inv-15 (1.71 g, 43% yield) in the same manner as in synthesis example 2.

GC-Mass (calculated: 628.24 g / mol, measured: 628 g / mol)

[Synthesis Example 16] Synthesis of Inv-16

Pd (OAc) ₂ (0.07 g, 5 mol%), NaO (t-Bu) (1.52 mmol), IIC-4 (3 g, 6.32 mmol), 4-chloro-2,6-diphenylpyrimidine g, 15.80 mmol), P ( t-bu) 3 (0.13 g, 0.63 mmol) and Toluene (100 ml) and the synthesis example 1, the same manner as the desired compound Inv-16 (2.72 g and using, yield: 61% ).

GC-Mass (calculated: 704.27 g / mol, measured: 704 g / mol)

[Synthesis Example 17] Synthesis of Inv-17

Cu powder (0.04 g, 0.63 mmol), K ₂ CO ₃ (0.87 g, 6.32 mmol), Na 2 (3-bromophenyl) naphthalene (2.69 g, 9.48 mmol) Inv-17 (1.71 g, yield 40%) was obtained in the same manner as in Synthesis Example 2, using ₂ SO ₄ (0.90 g, 6.32 mmol) and nitrobenzene (100 ml).

GC-Mass (calculated: 676.26 g / mol, measured: 676 g / mol)

[Synthesis Example 18] Synthesis of Inv-18

3-bromo-9- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -9H-carbazole (5.25 g, 9.48 The same procedure as in Synthesis Example 2 (2) was carried out using Cu powder (0.04 g, 0.63 mmol), K ₂ CO ₃ (0.87 g, 6.32 mmol), Na ₂ SO ₄ (0.90 g, 6.32 mmol) (2.16 g, yield 36%) of the desired compound, Inv-18, was obtained.

GC-Mass (946.35 g / mol, measured: 946 g / mol)

[Synthesis Example 19] Synthesis of Inv-19

IIC-5 (3 g, 6.32 mmol), 3-bromopyridine (1.50 g, 9.48 mmol), Cu powder (0.04 g, 0.63 mmol), K 2 CO 3 (0.87 g, 6.32 mmol), Na 2 SO 4 (0.90 g, 6.32 mmol) and nitrobenzene (100 ml), Inv-19 (1.81 g, yield 52%) was obtained in the same manner as in Synthesis Example 2. [

GC-Mass (calculated: 551.21 g / mol, measured: 551 g / mol)

[Synthesis Example 20] Synthesis of Inv-20

IIC-5 (3 g, 6.32 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (2.61 g, 7.59 mmol), Pd (OAc) 2 (0.07 g, 5 use mol%), NaO (t- bu) (1.52 g, 15.80 mmol), P (t-bu) 3 (0.13 g, 0.63 mmol) and Toluene (100 ml), in the same manner as in synthesis example 1 The target compound Inv-20 (3.31 g, yield 67%) was obtained.

GC-Mass (theory: 781.30 g / mol, measured: 781 g / mol)

[Synthesis Example 21] Synthesis of Inv-21

, Cu ₂ CO ₃ (0.87 g, 6.32 mmol), Na ₂ (0.02 g, 0.63 mmol), IIC-5 (3 g, 6.32 mmol), 2-bromo-6-phenylpyridine Inv-21 (2.02 g, yield 51%) was obtained in the same manner as in Synthesis Example 2, using SO ₄ (0.90 g, 6.32 mmol) and nitrobenzene (100 ml).

GC-Mass (calculated: 627.24 g / mol, measured: 627 g / mol)

[Synthesis Example 22] Synthesis of Inv-22

IIC-6 (3 g, 6.32 mmol), 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine (4.40 g, 9.48 mmol) The target compound Inv-1 was obtained in the same manner as in Synthesis Example 2, using 0.63 mmol of K ₂ CO ₃ (0.87 g, 6.32 mmol), Na ₂ SO ₄ (0.90 g, 6.32 mmol) and nitrobenzene (100 ml) 22 (2.50 g, yield 46%).

GC-Mass (calculated: 857.33 g / mol, measured: 857 g / mol)

[Synthesis Example 23] Synthesis of Inv-23

(0.04 g, 0.63 mmol), K ₂ CO ₃ (0.87 g, 6.32 mmol), Na ₂ SO ₄ (0.90 g, 0.63 mmol), IIC-6 (3 g, 6.32 mmol), 2-bromonaphthalene g, 6.32 mmol) and nitrobenzene (100 ml), Inv-23 (1.82 g, yield 48%) was obtained in the same manner as in Synthesis Example 2. [

GC-Mass (theory: 600.23 g / mol, measurement: 600 g / mol)

[Synthesis Example 24] Synthesis of Inv-24

(3 g, 6.32 mmol), 2,4-di (biphenyl-3-yl) -6- (3-chlorophenyl) -1,3,5-triazine (3.76 g, 7.59 mmol), Pd ) ₂ (0.07 g, 5 mol%), NaO (t-bu) (1.52 g, 15.80 mmol), P (t-bu) ₃ (0.13 g, 0.63 mmol) and Toluene The target compound Inv-24 (3.84 g, yield 65%) was obtained in the same manner as in Synthesis Example 1.

GC-Mass (calculated: 933.36 g / mol, measured: 933 g / mol)

[Synthesis Example 25] Synthesis of Inv-25

(0.30 g, 0.43 mmol), K ₂ CO ₃ (0.59 g, 4.25 mmol), Na ₂ SO ₄ (0.60 g, 0.43 mmol), Iodobenzene (1.30 g, 4.25 mmol) and nitrobenzene (100 ml), Inv-25 (1.43 g, yield 43%) was obtained in the same manner as in Synthesis Example 2. [

GC-Mass (theory: 781.30 g / mol, measured: 781 g / mol)

[Synthesis Example 26] Synthesis of Inv-26

2-bromo-4,6-diphenylpyridine (1.98 g, 6.38 mmol), Cu powder (0.03 g, 0.43 mmol), K ₂ CO ₃ (0.59 g, 4.25 mmol), IIC- Na ₂ SO was obtained _{4 (0.60 g, 4.25 mmol)} , nitrobenzene (100 ml), the objective compound Inv-26 in the same manner as in synthesis example 2, using (1.59 g, yield 40%).

GC-Mass (calculated: 934.35 g / mol, measured: 934 g / mol)

[Synthesis Example 27] Synthesis of Inv-27

IIC-7 (3 g, 4.25 mmol), 2-bromobiphenyl (1.49 g, 6.38 mmol), Cu powder (0.03 g, 0.43 mmol), K 2 CO 3 (0.59 g, 4.25 mmol), Na 2 SO 4 (0.60 g, 4.25 mmol) and nitrobenzene (100 ml), Inv-27 (1.39 g, yield 38%) was obtained in the same manner as in Synthesis Example 2. [

GC-Mass (calculated: 857.33 g / mol, measured: 857 g / mol)

[Synthesis Example 28] Synthesis of Inv-28

IIC-8 (3 g, 4.25 mmol), 1-bromo-3,5-diphenyl benzene (1.97 g, 6.38 mmol), Cu powder (0.03 g, 0.43 mmol), K 2 CO 3 (0.59 g, 4.25 mmol) , Na ₂ SO using _{4 (0.60 g, 4.25 mmol)} , nitrobenzene (100 ml), to obtain the desired compound of Inv-28 (1.55 g, yield 39%) in the same manner as in synthesis example 2.

GC-Mass (calculated: 933.36 g / mol, measured: 933 g / mol)

[Synthesis Example 29] Synthesis of Inv-29

Dibenzo [b, d] thiophene (2.16 g, 6.38 mmol), Cu powder (0.03 g, 0.43 mmol), K ₂ CO ₃ (0.59 g, , 4.25 mmol), using _{Na 2 SO 4 (0.60 g,} 4.25 mmol), nitrobenzene (100 ml), obtaining in Inv-28 (1.52 g, yield 37%) of the desired compound in the same manner as in synthesis example 2 Respectively.

GC-Mass (calculated: 963.31 g / mol, measured: 963 g / mol)

[Synthesis Example 30] Synthesis of Inv-30

(0.09 g, 0.43 mmol), K ₂ CO ₃ (0.59 g, 4.25 mmol), Na ₂ SO ₄ (0.60 mmol), IIC-8 (3 g, 4.25 mmol), 4-bromobiphenyl g, 4.25 mmol) and nitrobenzene (100 ml), the target compound Inv-30 (1.53 g, yield 42%) was obtained in the same manner as in Synthesis Example 2. [

GC-Mass (calculated: 857.33 g / mol, measured: 857 g / mol)

[Synthesis Example 31] Synthesis of Inv-31

Pd (dba) ₃ (0.29 g, 5 mol%), K ₂ CO ₃ (2.62 g, 5 mmol), 2-chloro-4-phenylquinazoline (1.83 g, 7.59 mmol) , 18.97 mmol), BINAP (0.20 g, 5 mol%) and 1,4-dioxane (50 ml) were mixed and refluxed for 12 hours.

After the reaction was completed, the reaction mixture was extracted with methylene chloride, then the water was removed with MgSO ₄ and the residue was purified by column chromatography (Hexane: MC = 4: 1 (v / v)) to obtain Inv-31 (1.37 g, yield 32 %).

GC-Mass (calculated: 678.25 g / mol, measured: 678 g / mol)

[Examples 1 to 31] Fabrication of organic EL device

The compounds Inv-1 to Inv-31 synthesized in Synthesis Example 1-31 were subjected to high purity sublimation purification by a conventionally known method, and a green organic EL device was fabricated according to the following procedure.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or 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.

Each compound of m-MTDATA (60 nm) / TCTA (80 nm) / Inv-1 to Inv-31 + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in that order.

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

[Comparative Example 1] Fabrication of organic EL device

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

[Evaluation example]

The driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2 were measured for each of the organic EL devices manufactured in Example 1-31 and Comparative Example 1, and the results are shown in Table 1 below.

Sample Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 1 Inv-1 6.85 516 38.3 Example 2 Inv-2 6.72 515 39.4 Example 3 Inv-3 6.73 516 39.0 Example 4 Inv-4 6.77 518 39.3 Example 5 Inv-5 6.81 517 40.1 Example 6 Inv-6 6.82 516 41.0 Example 7 Inv-7 6.90 517 39.9 Example 8 Inv-8 6.73 516 39.1 Example 9 Inv-9 6.75 516 39.5 Example 10 Inv-10 6.78 517 39.2 Example 11 Inv-11 6.83 518 38.6 Example 12 Inv-12 6.91 518 39.7 Example 13 Inv-13 6.87 515 40.6 Example 14 Inv-14 6.81 516 39.9 Example 15 Inv-15 6.79 517 39.7 Example 16 Inv-16 6.83 517 38.6 Example 17 Inv-17 6.85 516 39.5 Example 18 Inv-18 6.71 517 40.5 Example 19 Inv-19 6.69 518 39.9 Example 20 Inv-20 6.72 517 38.5 Example 21 Inv-21 6.78 516 39.6 Example 22 Inv-22 6.85 518 39.3 Example 23 Inv-23 6.81 515 38.9 Example 24 Inv-24 6.88 516 39.0 Example 25 Inv-25 6.84 517 40.3 Example 26 Inv-26 6.78 516 39.7 Example 27 Inv-27 6.74 517 39.5 Example 28 Inv-28 6.77 518 38.8 Example 29 Inv-29 6.82 517 39.0 Example 30 Inv-30 6.76 517 39.1 Example 31 Inv-31 6.79 517 41.3 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, the green organic EL device of Example 1-31 in which the compound (Inv-1 to Inv-31) according to the present invention was used as a light emitting layer was the green organic EL of Comparative Example 1 using CBP It can be seen that the device exhibits excellent performance in terms of efficiency and driving voltage as compared with the device.

Claims (8)

delete A compound represented by any one of the following formulas (3) to (8):
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

In the above Formulas 3 to 8,
X ₁ and X ₂ are both N (Ar ₁ )
Wherein Ar ₁ is the same or different and is each independently a C ₆ to C ₄₀ aryl group or a heteroaryl group having 5 to 40 nuclear atoms,
R ₁ to R ₉ and Ra are the same or different and each independently represents hydrogen, deuterium, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₄₀ aryl group, and a heteroaryl group having 5 to 40 nuclear atoms &Lt; / RTI &gt;
n is an integer from 0 to 4,
In the above R ₁ to R _9, Ra and Ar _1, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₄₀ aryl group, nuclear atoms heteroaryl of 5 to 40 groups, each independently selected from deuterium, C ₁ ~ C of _A C ₆ to C ₄₀ aryl group, and a heteroaryl group having 5 to 40 nuclear atoms. delete delete delete The compound according to claim 2, wherein Ar ₁ is selected from the substituent groups represented by the following S1 to S204, R ₁ to R _9, and R _a are each independently selected from the group consisting of hydrogen, &Lt; / RTI &gt;

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 the compound according to any one of claims 2 to 6. The organic electroluminescent device according to claim 7, wherein at least one organic compound layer containing the compound is a light emitting layer.