KR101622809B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device including the same, wherein the compound of the present invention is introduced into a material for an organic electroluminescent device, preferably a host material of the luminescent layer, The overall characteristics such as voltage and lifetime can be improved.

Description

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

The present invention relates to a novel organic compound 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.

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

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

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

The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. Since the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as much as that of the fluorescent material, studies on phosphorescent host materials as well as phosphorescent dopants have been conducted.

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

However, since the conventional materials have low glass transition temperature and thermal stability deteriorates, they are not satisfactory in terms of lifetime in the OLED device, and improvements in the light emitting properties are needed. Therefore, development of materials with higher performance is required.

It is an object of the present invention to provide a novel organic compound which is excellent in thermal stability due to a high glass transition temperature and can improve the bonding strength between holes and electrons to improve luminescent properties.

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,

Wherein _one of Y ₁ and Y ₂ , Y ₂ and Y ₃ , and one of Y ₃ and Y ₄ is C (R ₁ ), and each C (R ₁ ) is a condensation product of R ₁ and R ₁ , Forming a ring,

Y ₁ to Y ₄ are independently N or C (R ₁ ), and the remainder not forming the condensed ring of the formula (2)

Wherein when R < _{1 >} is plural, they are the same or different from each other;

In Formula 2,

The dotted line means a moiety condensed in formula (1);

Wherein one of Y ₅ and Y ₆ , Y ₆ and Y _7, and Y ₇ and Y ₈ is both C (R ₂ ), and each of C (R ₂ ) and R ₂ is condensed with each other to form a condensed ring Lt; / RTI >

To from Y ₅ to Y ₈ rest does not form a condensed ring of the general formula (3) are each independently N or C (R _2),

When a plurality of R < ₂ > s are the same or different from each other;

In Formula 3,

The dotted line means a moiety condensed in formula (2);

Y ₉ to Y ₁₂ are each independently N or C (R ₃ )

Wherein when R < ₃ > is plural, they are the same or different from each other;

X _1, X ₄ and X ₅ is selected from the group consisting of each independently O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and _{Si (Ar 4) (Ar 5} ), In this case, X ₁ , X ₄ And X < ₅ > is N (Ar &_lt; ₁ >);

X ₂ and X ₃ are each independently N or C (R ₄ ), provided that when plural R ₄ are plural, they are the same as or different from each other;

R ₁ to R ₄ and Ar ₁ to Ar ₅ are the same or different and each independently represents hydrogen, deuterium (D), halogen, cyano group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkene A C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group , A C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group , C group ₆ to arylboronic of C _40, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ of the phosphine oxide group, and a C ₆ to C ₄₀ selected from an aryl silyl group the group consisting of or of, or adjacent groups of To form a condensed ring,

R ₁ to R ₄ and Ar ₁ to Ar ₅ of C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ of the phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl groups are each independently a heavy hydrogen (D), a halogen, a cyano group, an alkenyl group of C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C ₆ ~ C _40, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₄₀ of the arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a 3 to 40 nuclear atoms of a heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl yarn Group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl And when the substituent is plural, they may be the same or different from each other.

The organic electroluminescent device according to the present invention includes a cathode, an anode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers includes one or more organic compounds A light emitting device is provided.

At least one of the organic layers including the compound of Formula 1 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. Preferably, The compound represented by the formula (1) is a blue, green or red phosphorescent host material.

The compound represented by the formula (1) according to the present invention is excellent in thermal stability and phosphorescence property and can be used as an organic material layer material of an organic electroluminescent device.

In particular, when the compound represented by the general formula (1) is used as a phosphorescent host material in the light emitting layer, an organic electroluminescent device having excellent light emitting performance, low driving voltage, high efficiency, Further, a full color display panel having greatly improved performance and lifetime can 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 three inden moieties containing one or more heteroatoms such as N, O, S are sequentially fused to form a basic skeleton and various substituents are bonded to the basic skeleton Which is characterized by being represented by the above formula (1).

The compound represented by the general formula (1) includes a basic framework in which three inden moieties containing one or more hetero atoms such as N, O, S and the like are condensed to form a compound having a broad band gap (sky blue to red) You can have energy. In addition, since the compound contains a basic skeleton in which the three indene moieties are condensed, and the aromatic ring substituent is introduced into such a skeleton, the whole molecule can have a bipolar characteristic, The bonding force can be increased. Therefore, when the compound of Formula 1 is applied to the organic EL device, since the compound can exhibit superior characteristics as a host material of the light emitting layer compared to the conventional CBP, the phosphorescence characteristics of the device are improved and the hole injection ability and / Transporting ability, luminous efficiency, driving voltage, lifetime characteristics and the like can be improved. The compound has a wide band gap (sky blue to red) because the energy level can be controlled by the above-mentioned substituents, and thus it can be applied not only to a light emitting layer but also to a hole transporting layer, a hole injecting layer and the like.

In addition, since the compound of formula (1) has an aromatic ring substituent introduced into the basic skeleton, the molecular weight of the compound is significantly increased, so that the glass transition temperature can be improved. As a result, 4-dicarbazolybiphenyl). &Lt; / RTI &gt; In addition, when the compound of the present invention is contained in an organic material layer such as a light emitting layer, since the various aromatic ring substituents are effective in inhibiting the crystallization of the organic material layer, the durability and lifetime characteristics of the organic EL device containing the compound can be greatly improved .

In addition, the compound of the present invention can be used as a material of a hole injection / transport layer of an organic EL device, or as a blue, green and / or red phosphorescent host material (preferably a phosphorescent host material) It is possible to exert an excellent effect in terms of the efficiency (for example, current efficiency, luminous efficiency) and life span of the device compared to the conventional CBP. In addition, the compound may be used in various organic layers such as a light-emitting auxiliary layer according to the introduced substituent. Therefore, the compound according to the present invention can greatly contribute to the improvement of the performance and the life of the organic EL device, and in particular, the lifetime of the organic EL device is greatly improved in maximizing the performance of the full-color organic EL panel.

In the compounds of the formula (1), the Y ₁ and Y _2, Y ₂ and Y _3, and Y ₃ and Y ₄ either both C (R _1), provided each of the C (R ₁₎ is R ₁ each And condensed to form a condensed ring represented by the general formula (2). For example, Y ₁ to Y ₄ when in the Y ₁ and Y ₂ are both C (R _1), and each C (R ₁₎ is R ₁ are condensed with each other to form a condensed ring of the general formula (2), and thus The compound of the present invention is represented by the following formula (4) or (7).

The remaining of Y ₁ to Y ₄ which do not form the condensed ring of formula (2) may be independently N or C (R ₁ ), preferably all C (R ₁ ). Here, when a plurality of R &lt; ₁ &gt; s are the same or different from each other.

In Formula 2, Y ₅ and Y ₆ , Y ₆ and Y _7, and Y ₇ and Y ₈ are all C (R ₂ ), and each of C (R ₂ ) and R ₂ is condensed with each other, To form a condensed ring represented by the following formula.

The remaining of Y ₅ to Y ₈ not forming the condensed ring of formula (3) may be independently N or C (R ₂ ), preferably all C (R ₂ ). At this time, when a plurality of R &lt; ₂ &gt; are present, they are the same as or different from each other.

In Formula 3, Y ₉ to Y ₁₂ are each independently N or C (R ₃ ), preferably all C (R ₃ ). Here, when a plurality of R &lt; ₃ &gt; is plural, they are the same or different from each other.

Further, in the formula, X _1, X ₄ and X ₅ are, each independently, O, S, Se, N (Ar 1), C (Ar 2) (Ar 3) and _{Si (Ar 4) (Ar 5} ) , Wherein at least one of X ₁ , X ₄ and X ₅ is N (Ar ₁ ), preferably X ₄ And X &lt; ₅ &gt; may all be N (Ar &_lt; ₁ &gt;).

X ₂ and X ₃ are each independently N or C (R ₄ ), and when R ₄ is plural, they are the same or different.

R ₁ to R ₄ and Ar ₁ to Ar ₅ are the same or different and each independently represents hydrogen, deuterium (D), halogen, cyano group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atoms aryl of from 5 to 40 heteroaryl group, a C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ of alkyloxy An arylamine group of C ₆ to C ₄₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group of 3 to 40 nucleus atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkyl boron group, C group ₆ to arylboronic of C _40, C ₆ to C ₄₀ aryl phosphine group, C ₆ to C ₄₀ aryl phosphine oxide group, and a C ₆ to C ₄₀ aryl silyl group selected from the group consisting of, or in, or May be bonded to adjacent groups to form a condensed ring.

Preferably, R ₁ to R ₄ and Ar ₁ to Ar ₅ are the same or different and each independently represents hydrogen, deuterium (D), a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms And an arylamine group having from ₆ to ₄₀ carbon atoms.

For example, R ₁ to R ₄ and Ar ₁ to Ar ₅ may be the same or different and each independently hydrogen or deuterium (D), or may be selected from the group consisting of the following substituents S1 to S211, It is not.

In addition, R ₁ to R ₄ and Ar ₁ to Ar ₅ may be the same or different and each independently selected from substituents represented by the following formulas (D-1) to (D-15), but are not limited thereto.

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

L is a single bond or a group selected from the group consisting of a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms,

When there are a plurality of R &lt; _{11 &} gt ;, they are the same as or different from each other,

When there are a plurality of R &lt; ₂₁ &gt; s, they are the same or different from each other,

R ₁₁ and R ₂₁ are each other the same or different, each independently represent hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, an alkenyl group of C ₁ ~ 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 group of ₆₀ arylboronic, C ₁ ~ C ₆₀ of the phosphine group, C ₁ ~ C ₆₀ phosphine oxide group, and a C ₆ ~, or selected from the group consisting of an aryl amine of the C ₆₀ of, or the adjacent groups combine to form a condensed ring In addition,

n is an integer of 0 to 4;

The compound represented by the formula (1) according to the present invention can be represented by any one of the following formulas (4) to (9).

In the above formulas 4 to 9,

Y ₁ to Y ₈ , and X ₁ to X ₄ are each as defined in formula (1).

The compound of formula (1) may be represented by any of the following formulas (C-1) to (C-36).

In the above formulas C-1 to C-36,

X ₁ to X ₅ , and Y ₁ to Y ₁₂ are each as defined in formula (1).

The compound represented by the formula (1) according to the present invention is represented by any one of the following formulas (10) to (15).

In the above formulas 10 to 15,

X ₂ and X ₃ , Y ₁ to Y ₄ , and Ar ₁ to Ar ₅ are as defined in formula (1), respectively.

The compound of formula (I) according to the present invention may be represented by any one of the following formulas A-1 to A-24, but is not limited thereto. Among them, the compound of the present invention is preferably represented by any one of the following formulas (A-1) to (A-6) in consideration of the physical and chemical properties of the compound.

In the above Formulas A-1 to A-24,

R ₄ , Y ₁ to Y _4, and Ar ₁ to Ar ₅ are each as defined in formula (1).

Specific examples of the compound of formula (1) according to the present invention include, but are not limited to, the following compounds Inv-1 to Inv-750.

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, iso-amyl, .

The alkenyl in the present invention is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include vinyl, allyl, Isopropenyl, 2-butenyl, and the like.

Alkynyl in the present invention is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include ethynyl, 2- 2-propynyl, and the like.

The aryl in the present invention 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.

The 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, the ring may be pendant or condensed with each other, or may be condensed 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 is 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 alkyloxy in the present invention is a monovalent substituent group represented by R'O-, wherein R 'is an alkyl having 1 to 40 carbon atoms and includes 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.

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

The 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 of the ring, preferably 1 to 3 carbons, is N, O, S or Se. &Lt; / RTI &gt; Examples of such heterocycloalkyl include morpholine, piperazine and the like.

The alkylsilyl in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms, and arylsilyl means silyl substituted with aryl having 5 to 40 carbon atoms.

The condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

&Lt; Organic electroluminescent device &

The present invention provides an organic electroluminescent device comprising the above-described compound.

Specifically, the organic electroluminescent device according to the present invention includes 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 And compounds represented by the formulas of the present invention. At this time, the compounds 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 the compound of Formula 1 described above. Preferably, the organic layer containing the compound of the present invention may be a light emitting layer.

According to an embodiment of the present invention, the light emitting layer of the organic electroluminescent device may include a host material, and the host material may include the compound of the above formula (1). 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 the compound of the present invention, and preferably the light emitting layer may include the compound of Formula 1. At this time, the compound of Formula 1 may be used as a phosphorescent host material of the light emitting layer. An electron injection layer may be further stacked on the electron transport layer.

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

The organic electroluminescent device according to the present invention can be formed by using materials and methods known in the art, except that one or more of the organic layers (for example, the light emitting layer) And electrodes.

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

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

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

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

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 compound IC-1 and IC-2

<Step 1> Synthesis of N- (2,4-dibromophenyl) benzamide

Benzoyl chloride (140.05 g, 1.0 mol) and pyridine (157.62 mL, 1.99 mol) were slowly added dropwise at room temperature while stirring 2,4-dibromoaniline (250 g, 1.0 mol) and dichloromethane (1 L) in a stream of nitrogen.

After 2 hours, the reaction was terminated and the organic layer was extracted with dichloromethane. The organic layer was dried over MgSO ₄ and purified by column chromatography (Hexane: EA = 4: 1 (v / v) 4-dibromophenyl) benzamide (258.72 g, yield 73%).

^{1 H-NMR: δ 7.53 (} d, 1H), 7.60 (d, 1H), 7.65 (dd, 2H), 7.72 (t, 1H), 7.98 (s, 1H), 8.04 (d, 2H), 9.16 ( s, 1 H)

<Step 2> Synthesis of 6-bromo-2-phenylbenzo [d] oxazole

(2,4-dibromophenyl) benzamide (258.72 g, 0.73 mol), K ₂ CO ₃ (201.04 g, 1.45 mol) and DMSO (5000 ml) obtained in Step 2 of Preparation Example 1 were mixed And the mixture was stirred at 140 ° C for 1.5 hours.

After the reaction was completed, the organic layer was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 9: 1 (v / v)) to obtain 6-bromo-2- phenylbenzo [ ] oxazole (161.48 g, yield 81%).

^{1 H-NMR: δ 7.42 (} t, 1H) 7.44 (s, 1H), 7.53 (m, 3H), 7.62 (d, 1H), 8.07 (d, 2H)

<Step 3> Synthesis of 2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole

6-bromo-2-phenylbenzo [d] oxazole (161.48 g, 0.589 mol), 4,4,4 ', 4', 5,5,5 ' Pd (dppf) Cl ₂ (24.05 g, 29.46 mmol), KOAc (173.44 g, 1.77 mol), and N, N-dimethylformamide (179.52 g, 0.707 mol) 1,4-Dioxane (3000 ml) were mixed and stirred at 130 ° C for 12 hours.

After the reaction was completed, the organic layer was extracted with ethyl acetate, the water was removed with MgSO ₄ , and the residue was purified by column chromatography (Hexane: EA = 7: 1 (v / v) 4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole (149.48 g, yield 79%).

^{1 H-NMR: δ 1.25 (} s, 12H) 7.42 (d, 1H), 7.45 (s, 1H), 7.52 (dd, 2H), 7.63 (d, 1H), 7.76 (s, 1H), 8.07 (d , 2H)

<Step 4> Synthesis of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole (obtained in Step 3 of Preparation Example 1, 149.48 g , 0.465 mol), 4-bromo -2-iodo-1-nitrobenzene (138.73 g, 0.423 mol), Pd (PPh 3) 4 (24.45 g, 21.15 mmol), K 2 CO 3 (175.43 g, 1.27 mol), THF / H ₂ O (2000 ml / 1000 ml) were mixed and stirred at 80 ° C for 12 hours.

After the reaction was completed, the organic layer was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 8: 1 (v / v)) to obtain 113.7 g of 6- (5-bromo-2- nitrophenyl) Yield: 68%).

^{1 H-NMR: δ 7.42 (} t, 1H) 7.49 (s, 1H), 7.55 (dd, 2H), 7.69 (d, 1H), 7.71 (s, 1H), 7.78 (d, 1H), 7.96 (d , &Lt; / RTI &gt; 1H), 8.07 (d, 2H), 8.24

Synthesis of 7-bromo-2-phenyl-10H-oxazolo [5,4-a] carbazole and 8-bromo-2-phenyl-5H-oxazolo [4,5-b]

2-phenylbenzo [d] oxazole (113.7 g, 0.29 mol), triphenylphosphine (188.65 g, 0.72 mol) obtained in Step 4 of Preparation Example 1, 1 , And 2-dichlorobenzene (1500 ml) were mixed and stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, and the organic layer was extracted with dichloromethane, followed by addition of MgSO ₄ and filtration. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 4: 1 (v / v)) to obtain the compound mid-1 (7-bromo-2-phenyl-10H-oxazolo [ carbazole) (47 g, yield 45%) and compound mid-2 (8-bromo-2-phenyl-5H-oxazolo [4,5- b] carbazole) (44.93 g, yield 43%).

¹ of the compound mid-1 H-NMR: δ 7.22 (d, 1H), 7.33 (t, 1H) 7.43 (d, 1H), 7.53 (dd, 2H), 7.55 (d, 1H), 8.07 (m, 3H ), 8.13 (d, IH), 10.2 (s, IH)

¹ H-NMR of compound mid-2: 7.41 (m, 3H), 7.51 (d, 3H), 7.57 (s,

<Step 6> Synthesis of 7-bromo-2,10-diphenyl-10H-oxazolo [5,4-a]

10-oxazolo [5,4-a] carbazole (47 g, 129.4 mmol), iodobenzene (39.6 g, 194.1 mmol) obtained in Step 5 of Preparation Example 1, Cu powder from (0.82 g, 12.94 mmol), K 2 CO 3 (17.88 g, 129.4 mmol), Na 2 SO 4 (18.38 g, 129.4 mmol), mixture of nitrobenzene (800 ml) and, 200 ℃ was stirred 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 . The solvent was removed from the organic layer from which water had been removed and then purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain 7-bromo- 2,10- carbazole (29.56 g, yield 52%).

^{1 H-NMR: δ 7.21 (} d, 1H), 7.42 (t, 1H) 7.46 (m, 2H), 7.52 (d, 4H), 7.57 (d, 3H), 8.05 (m, 3H), 8.11 (d , 1H)

<Step 7> Synthesis of 7- (2-nitrophenyl) -2,10-diphenyl-10H-oxazolo [5,4-a]

2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole e used in Step 4 of Preparation Example 1 (149.48 g, Bromo-2-iodo-1-nitrobenzene (138.73 g, 67.29 mmol) was obtained by using 7-bromo-2,10- diphenyl-10H-oxazolo [5,4- , 2-nitrophenyl) -2,10-dihydroxybenzoic acid was prepared by the same procedure as Step 4 of Preparation Example 1, except that 2-nitrophenylboronic acid (10.21 g, 61.17 mmol) -diphenyl-10H-oxazolo [5,4-a] carbazole (17.38 g, yield 59%).

^{1 H-NMR: δ 7.20 (} d, 1H), 7.43 (t, 1H) 7.47 (m, 2H), 7.51 (d, 4H), 7.58 (d, 3H), 7.68 (d, 1H), 7.89 (d , 2H), 8.04 (m, 4H), 8.14 (d, IH)

<Step 8> Synthesis of Compound IC-1 and IC-2

Obtained in Step 7 of Preparation Example 1 instead of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (113.7 g, 0.29 mol) used in <Step 5> Step 5 of Preparation Example 1 was repeated except that 2-nitrophenyl-2,10-diphenyl-10H-oxazolo [5,4-a] carbazole (17.38 g, 36.1 mmol) To obtain compound IC-1 (6.98 g, yield 43%) and compound IC-2 (7.63 g, yield 47%).

^One of the compounds IC-1 H-NMR: δ , 7.23 (d, 1H), 7.29 (d, 1H), 7.43 (m, 3H), 7.50 (m, 5H), 7.55 (s, 1H), 7.58 (d 2H), 7.63 (d, IH), 8.05 (d, 2H), 8.12

Compound ¹ H-NMR of the IC-2: δ 7.24 (d , 1H), 7.31 (d, 1H), 7.42 (m, 3H), 7.52 (m, 5H), 7.59 (d, 2H), 7.65 (d, 1H), 7.96 (d, 1H), 8.04 (d, 2H), 8.13 (d, 2H), 11.56

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

<Step 1> Synthesis of 8-bromo-2,5-diphenyl-5H-oxazolo [4,5-b] carbazole

Obtained in Step 5 of Preparation Example 1 was used instead of 7-bromo-2-phenyl-10H-oxazolo [5,4-a] carbazole (47 g, 129.4 mmol) used in Step 6 of Preparation Example 1, bromo-2-phenyl-5H-oxazolo [4,5-b] carbazole (44.93 g, 123.7 mmol) was used in place of 8-bromo -2,5-diphenyl-5H-oxazolo [4,5-b] carbazole (27.71 g, yield 51%).

^{1 H-NMR: δ 7.40 (} m, 3H), 7.45 (t, 1H), 7.50 (d, 2H), 7.52 (d, 3H), 7.57 (s, 1H), 7.62 (d, 2H), 8.04 ( m, 3 H), 11.51 (s, 1 H)

<Step 2> Synthesis of 8- (2-nitrophenyl) -2,5-diphenyl-5H-oxazolo [4,5-b]

The procedure of Step 1 of Preparation Example 2 was repeated except that 7-bromo-2,10-diphenyl-10H-oxazolo [5,4-a] carbazole (29.56 g, 67.29 mmol) Step 7 of Preparation Example 1 was repeated except that 8-bromo-2,5-diphenyl-5H-oxazolo [4,5-b] carbazole (27.71 g, 63.08 mmol) To obtain 8- (2-nitrophenyl) -2,5-diphenyl-5H-oxazolo [4,5-b] carbazole (16.84 g, yield 61%).

^{1 H-NMR: δ 7.42 (} m, 3H), 7.45 (t, 1H), 7.52 (d, 2H), 7.53 (d, 3H), 7.56 (s, 1H), 7.63 (d, 2H), 7.71 ( (d, IH), 7.90 (d, IH), 8.00 (d, IH), 8.07 (m, 4H), 11.52

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

Except that 8- (2-nitrophenyl) -2,5-dimethylpyridine was used instead of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (113.7 g, 0.29 mol) used in <Step 5> except that triphenylphosphine (22.93 g, 87.44 mmol) was used instead of triphenylphosphine (188.65 g, 0.72 mol) instead of diphenyl-5H-oxazolo [4,5- b] carbazole (16.84 g, 34.97 mmol) The compound IC-3 (7.86 g, yield 50%) and compound IC-4 (6.60 g, yield 42%) were obtained in the same manner as in <Step 5> of Preparation Example 1.

Compound IC-3 ¹ H-NMR of: δ 7.29 (d, 1H) , 7.40 (m, 2H), 7.45 (t, 1H), 7.50 (m, 5H), 7.55 (s, 1H), 7.58 (d, 2H), 7.64 (d, 3H), 8.05 (d, 2H), 8.12

Compound IC-4 ¹ H-NMR of: δ 7.28 (d, 1H) , 7.39 (m, 3H), 7.46 (t, 1H), 7.50 (m, 5H), 7.56 (s, 2H), 7.59 (d, 2H), 7.65 (d, 1H), 8.06 (d, 2H), 8.11

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

<Step 1> Synthesis of N- (2,5-dibromophenyl) benzamide

Except that 2,5-dibromoaniline (250 g, 1.0 mol) was used instead of 2,4-dibromoaniline (250 g, 1.0 mol) used in <Step 1> of Preparation Example 1, (2,51-dibromophenyl) benzamide (251.14 g, yield 71%) was obtained in the same manner as in step 1).

^{1 H-NMR: δ 7.23 (} d, 1H), 7.47 (d, 1H), 7.63 (d, 2H), 7.70 (t, 1H), 7.76 (s, 1H), 8.03 (d, 2H), 10.25 ( s, 1 H)

<Step 2> Synthesis of 5-bromo-2-phenylbenzo [d] oxazole

(2,5-dibromophenyl) benzamide obtained in Step 1 of Preparation Example 3 instead of N- (2,4-dibromophenyl) benzamide (258.72 g, 0.73 mol) used in Step 2 of Preparation Example 1 5-bromo-2-phenylbenzo [d] oxazole (155.12 g, yield 80%) was obtained in the same manner as in <Step 2> of Preparation Example 1, except that 251.14 g .

^{1 H-NMR: δ 7.42 (} m, 2H), 7.51 (d, 2H), 7.60 (d, 1H), 7.68 (d, 1H), 8.05 (d, 2H)

<Step 3> Synthesis of 2-phenyl-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole

Bromo-2-phenylbenzo [d] thiazole obtained in Step 2 of Preparation Example 3 was used instead of 6-bromo-2-phenylbenzo [d] oxazole (161.48 g, 0.589 mol) used in Step 3 of Preparation Example 1, 2-phenyl-5- (4,4,5,5-tetramethyl-1, 3-dihydroxyphenyl) propanoate was prepared by the same procedure as Step 3 of Preparation Example 1, except that oxazole (155.12 g, 0.566 mol) 3,2-dioxaborolan-2-yl) benzo [d] oxazole (136.32 g, yield 75%).

^{1 H-NMR: δ 1.24 (} s, 12H), 7.30 (s, 1H), 7.42 (t, 1H), 7.53 (d, 2H), 7.75 (d, 1H), 7.79 (d, 1H), 8.07 ( d, 2H)

<Step 4> Synthesis of 5- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole used in Step 4 of Preparation Example 1 (149.48 g, 0.465 (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole (obtained in Step 3 of Preparation Example 3 2-nitrophenyl) -2-phenylbenzo [d] oxazole (108.27 g, 0.434 mol) was used in the same manner as Step 4 of Preparation Example 1, Yield: 71%).

^{1 H-NMR: δ 7.42 (} t, 1H), 7.52 (d, 2H), 7.72 (s, 1H), 7.79 (d, 1H), 7.85 (d, 1H), 7.98 (d, 1H), 8.04 ( d, 2H), 8.09 (s, IH), 8.21 (d, IH)

Step 5 Synthesis of 8-bromo-2-phenyl-5H-oxazolo [5,4-b] carbazole and 7-bromo-2-phenyl-10H-oxazolo [4,5-

Obtained in Step 4 of Preparation Example 3 instead of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (113.7 g, 0.29 mol) used in Step 5 of Preparation Example 1, Step 5 of Preparation Example 1 was repeated except that 5-bromo-2-nitrophenyl-2-phenylbenzo [d] oxazole (108.27 g, 0.274 mol) Bromo-2-phenyl-10H-oxazolo [4, 5] benzoic acid (43.78 g, 44% 5-a] carbazole (41.79 g, yield 42%).

Compound mid-3 ¹ of H-NMR: δ 7.40 (m , 2H), 7.43 (d, 1H), 7.51 (d, 3H), 7.54 (s, 1H), 8.04 (m, 3H), 11.64 (s, 1H)

Compound mid-4 ¹ H-NMR of: δ 7.00 (d, 1H) , 7.42 (m, 2H), 7.52 (d, 3H), 8.05 (m, 3H), 8.12 (d, 1H), 11.68 (s, 1H)

<Step 6> Synthesis of 8-bromo-2,5-diphenyl-5H-oxazolo [5,4-b] carbazole

Obtained in Step 6 of Preparation Example 3 instead of 7-bromo-2-phenyl-10H-oxazolo [5,4-a] carbazole (47 g, 0.129 mmol) used in Step 6 of Preparation Example 1, bromo-2-phenyl-5H-oxazolo [5,4-b] carbazole (43.78 g, 0.121 mmol) was used in place of 8-bromo -2,5-diphenyl-5H-oxazolo [5,4-b] carbazole (28.06 g, yield 53%).

^{1 H-NMR: δ 7.441 (} m, 2H), 7.43 (d, 1H), 7.46 (t, 1H), 7.50 (m, 5H), 7.54 (s, 1H), 7.59 (d, 2H), 8.06 ( m, 3H)

Step 7 Synthesis of 8- (2-nitrophenyl) -2,5-diphenyl-5H-oxazolo [5,4-b] carbazole

2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole e used in Step 4 of Preparation Example 1 (149.48 g, Bromo-2,5-diphenyl-5H-oxazolo [5,4-b] carbazole (28.06 g, 63.87 mmol) instead of 4-bromo-2-iodo-1-nitrobenzene , 2-nitrophenylboronic acid (9.69 g, 58.07 mmol) was used instead of 2-nitrophenylboronic acid (0.423 mol) in the same manner as in <Step 4> -diphenyl-5H-oxazolo [5,4-b] carbazole (17.33 g, yield 62%).

^{1 H-NMR: δ 7.41 (} m, 2H), 7.43 (d, 1H), 7.46 (t, 1H), 7.50 (m, 5H), 7.54 (s, 1H), 7.59 (d, 2H), 7.67 ( (d, IH), 7.77 (s, IH), 7.90 (d, IH), 8.05

<Step 8> Synthesis of compounds IC-5 and IC-6

Obtained in Step 7 of Preparation Example 3 instead of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (113.7 g, 0.29 mol) used in Step 5 of Preparation Example 1, Step 5 of Preparation Example 1 was repeated except that 2-nitrophenyl-2,5-diphenyl-5H-oxazolo [5,4-b] carbazole (17.33 g, 35.99 mmol) To obtain compound IC-5 (6.79 g, yield 42%) and compound IC-6 (6.63 g, yield 41%).

Compound IC-5 ¹ H-NMR of: δ 7.29 (d, 1H) , 7.40 (s, 2H), 7.43 (t, 2H), 7.51 (d, 5H), 7.55 (s, 2H), 7.58 (d, 2H), 7.64 (d, IH), 8.05 (d, 2H), 8.12

Compound IC-6 ¹ H-NMR of: δ 7.30 (d, 1H) , 7.41 (s, 1H), 7.44 (t, 2H), 7.50 (d, 5H), 7.56 (s, 1H), 7.59 (d, 2H), 7.65 (d, 3H), 8.04 (d, 2H), 8.11

[Preparation Example 4] Synthesis of compound IC-7 and IC-8

<Step 1> Synthesis of 7-bromo-2,10-diphenyl-10H-oxazolo [4,5-a] carbazole

Obtained in Step 5 of Preparation Example 3 instead of 7-bromo-2-phenyl-10H-oxazolo [5,4-a] carbazole (47 g, 129.4 mmol) used in Step 6 of Preparation Example 1, bromo-2-phenyl-10H-oxazolo [4,5-a] carbazole (41.79 g, 115.06 mmol) was used in place of 7-bromo -2,10-diphenyl-10H-oxazolo [4,5-a] carbazole (25.79 g, yield 51%).

^{1 H-NMR: δ 7.02 (} d, 1H), 7.41 (m, 2H), 7.46 (t, 1H), 7.51 (d, 2H), 7.53 (d, 3H), 7.59 (d, 2H), 8.06 ( m, 3 H), 8.13 (d, 1 H)

<Step 2> Synthesis of 7- (2-nitrophenyl) -2,10-diphenyl-10H-oxazolo [4,5-a] carbazole

Step 1 of Preparation Example 4 was repeated except that 7-bromo-2,10-diphenyl-10H-oxazolo [5,4-a] carbazole (29.56 g, 67.29 mmol) used in <Step 7> Step 7 of Preparation Example 1 was repeated except that 7-bromo-2,10-diphenyl-10H-oxazolo [4,5-a] carbazole (25.79 g, 58.71 mmol) To obtain 7- (2-nitrophenyl) -2,10-diphenyl-10H-oxazolo [4,5-a] carbazole (15.16 g, yield 59%).

^{1 H-NMR: δ 7.00 (} d, 1H), 7.41 (t, 1H), 7.45 (t, 1H), 7.50 (d, 4H), 7.58 (d, 2H), 7.67 (d, 1H), 7.77 ( (d, 1H), 7.90 (d, 1H), 8.00 (d, 2H), 8.05

<Step 3> Synthesis of compounds IC-7 and IC-8

Obtained in Step 2 of Preparation Example 4 instead of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (113.7 g, 0.29 mol) used in <Step 5> Step 5 of Preparation Example 1 was repeated except that 2-nitrophenyl-2,10-diphenyl-10H-oxazolo [4,5-a] carbazole (15.16 g, 31.49 mmol) To obtain compound IC-7 (6.09 g, yield 43%) and compound IC-8 (5.52 g, yield 39%).

Compound IC-7 ¹ H-NMR of: δ 7.01 (d, 1H) , 7.42 (t, 1H), 7.45 (t, 1H), 7.51 (d, 4H), 7.57 (d, 2H), 7.68 (d, 1H), 7.91 (d, 1H), 8.01 (d, 2H), 8.06 (d, 3H), 8.11

Compound IC-8 ¹ H-NMR of: δ 7.00 (d, 1H) , 7.41 (m, 2H), 7.45 (t, 1H), 7.50 (d, 4H), 7.54 (s, 1H), 7.58 (d, 2H), 7.67 (d, IH), 7.90 (d, IH), 8.00 (d, IH), 8.05

[Preparation Example 5] Synthesis of compound IC-9 and IC-10

<Step 1> Synthesis of N- (2,6-dibromophenyl) benzamide

Except that 2,6-dibromoaniline (250 g, 1.0 mol) was used instead of 2,4-dibromoaniline (250 g, 1.0 mol) used in <Step 1> of Preparation Example 1, (2,6-dibromophenyl) benzamide (254.68 g, yield 72%) was obtained by carrying out the same procedure as in the step 1].

^{1 H-NMR: δ 6.69 (} t, 1H), 7.63 (d, 2H), 7.70 (t, 1H), 7.74 (d, 2H), 8.03 (d, 2H), 10.25 (s, 1H)

<Step 2> Synthesis of 4-bromo-2-phenylbenzo [d] oxazole

(2,6-dibromophenyl) benzamide obtained in Step 1 of Preparation Example 5 instead of N- (2,4-dibromophenyl) benzamide (258.72 g, 0.73 mol) used in Step 2 of Preparation Example 1 4-bromo-2-phenylbenzo [d] oxazole (155.34 g, yield 79%) was obtained by following the procedure of <Step 2> of Preparation Example 1, except that 254.68 g .

^{1 H-NMR: δ 7.34 (} t, 1H), 7.41 (t, 1H), 7.51 (d, 2H), 7.60 (d, 1H), 7.73 (d, 1H), 8.05 (d, 2H)

<Step 3> Synthesis of 2-phenyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole

Bromo-2-phenylbenzo [d] thiazole obtained in Step 2 of Preparation Example 5 was used instead of 6-bromo-2-phenylbenzo [d] oxazole (161.48 g, 0.589 mol) used in Step 3 of Preparation Example 1, 2-phenyl-4- (4,4,5,5-tetramethyl-1, 3-dihydroxyphenyl) propanoate was prepared by following the procedure of Step 3 of Preparation Example 1, except that oxazole (155.34 g, 0.567 mol) 3,2-dioxaborolan-2-yl) benzo [d] oxazole (140.15 g, yield 77%).

^{1 H-NMR: δ 1.23 (} s, 12H), 7.41 (t, 1H), 7.45 (t, 1H), 7.51 (d, 2H), 7.75 (d, 1H), 7.79 (d, 1H), 8.05 ( d, 2H)

<Step 4> Synthesis of 4- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole

2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazo le used in Step 4 of Preparation Example 1 (149.48 g, (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole (140.15 g) obtained in Step 3 of Preparation Example 5 was used instead of 2-phenyl- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (105.04 g, 0.436 mol) was obtained in the same manner as in <Step 4> of Preparation Example 1, , Yield: 67%).

^{1 H-NMR: δ 7.42 (} t, 1H), 7.52 (d, 3H), 7.72 (s, 1H), 7.75 (d, 1H), 7.98 (d, 1H), 8.06 (d, 2H), 8.21 ( d, 1 H)

Step 5 Synthesis of 9-bromo-2-phenyl-6H-oxazolo [5,4-c] carbazole

Obtained in Step 4 of Preparation Example 5 was used instead of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (113.7 g, 0.29 mol) used in Step 5 of Preparation Example 1, Step 5 of Preparation Example 1 was repeated except that 5-bromo-2-nitrophenyl-2-phenylbenzo [d] oxazole (105.04 g, 0.266 mol) -2-phenyl-6H-oxazolo [5,4-c] carbazole (44.41 g, yield 46%).

¹ H-NMR: 8 7.08 (d, 1 H), 7.41 (m, 2 H), 7.51 (d, 3H), 7.63

<Step 6> Synthesis of 9-bromo-2,6-diphenyl-6H-oxazolo [5,4-c]

The 9-bromo-2-phenyl-10H-oxazolo [5,4-a] carbazole (47 g, 0.129 mmol) used in Step 6 of Preparation Example 1 was used instead of 7-bromo- bromo-2-phenyl-6H-oxazolo [5,4-c] carbazole (44.41 g, 0.122 mmol) was used in place of 9-bromo -2,6-diphenyl-6H-oxazolo [5,4-c] carbazole (29.01 g, yield 54%).

^{1 H-NMR: δ 7.08 (} d, 1H), 7.25 (d, 1H), 7.41 (t, 1H), 7.45 (t, 1H), 7.50 (d, 4H), 7.58 (d, 2H), 7.63 ( (d, IH), 7.72 (s, IH), 7.83 (d,

<Step 7> Synthesis of 9- (2-nitrophenyl) -2,6-diphenyl-6H-oxazolo [5,4-c] carbazole

2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole e used in Step 4 of Preparation Example 1 (149.48 g, Bromo-2,6-diphenyl-6H-oxazolo [5,4-c] carbazole (29.01 g, 66.04 mmol) obtained in Step 8 of Preparation Example 5 was used instead of 4-bromo- Step 4 of Preparation Example 1 was repeated except that 2-nitrophenylboronic acid (10.02 g, 60.03 mmol) was used instead of 2-iodo-1-nitrobenzene (138.73 g, 0.423 mol) - (2-nitrophenyl) -2,6-diphenyl-6H-oxazolo [5,4-c] carbazole (15.32 g, yield 53%).

^{1 H-NMR: δ 7.07 (} d, 1H), 7.40 (t, 1H), 7.46 (t, 1H), 7.51 (d, 4H), 7.58 (d, 2H), 7.66 (d, 2H), 7.77 ( (d, 1H), 7.82 (d, 1H), 7.90 (d,

<Step 8> Synthesis of compounds IC-9 and IC-10

The procedure of Example 5 was repeated except that 9- (4-chlorophenyl) -2-phenylbenzo [d] oxazole was used instead of 6- (5-bromo- Step 5 of Preparation Example 1 was repeated except that 2-nitrophenyl 2,6-diphenyl-6H-oxazolo [5,4-c] carbazole (15.32 g, 31.82 mmol) To obtain compound IC-9 (6.01 g, yield 42%) and compound IC-10 (5.72 g, yield 40%).

Compound IC-9 ¹ H-NMR of: δ 7.07 (d, 1H) , 7.29 (d, 1H), 7.40 (m, 2H), 7.46 (t, 1H), 7.50 (d, 5H), 7.55 (s, 1H), 7.58 (d, 2H), 7.64 (d, 2H), 8.06 (d, 2H), 8.12

Compound IC-10 ¹ H-NMR of: δ 7.06 (d, 1H) , 7.29 (d, 1H), 7.41 (t, 1H), 7.47 (t, 1H), 7.50 (m, 6H), 7.59 (d, 2H), 7.82 (d, 1H), 7.95 (d, 2H), 8.06

[Preparation Example 6] Synthesis of compound IC-11 and IC-12

<Step 1> Synthesis of 6- (4-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole used in Step 4 of Preparation Example 1 (149.48 g, 0.465 2-yl) benzo [d] oxazole (149.48 g, 0.465 mol) instead of 2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- except that 4-bromo-1-iodo-2-nitrobenzene (138.73 g, 0.423 mol) was used in place of bromo-2-iodo-1-nitrobenzene (138.73 g, 0.423 mol) 4-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (110.36 g, yield 66%).

^{1 H-NMR: δ 7.40 (} t, 1H), 7.48 (s, 1H), 7.51 (d, 2H), 7.68 (d, 1H), 7.79 (d, 1H), 7.94 (d, 1H), 8.05 ( d, 3H), 8.63 (d, IH)

<Step 2> Synthesis of 8-bromo-2-phenyl-10H-oxazolo [5,4-a]

Obtained in Step 1 of Preparation Example 6 instead of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (113.7 g, 0.29 mol) used in <Step 5> The same procedure as in <Step 5> of Preparation Example 1 was carried out except that 4-bromo-2-nitrophenyl-2-phenylbenzo [d] oxazole (110.36 g, 0.279 mol) -2-phenyl-10H-oxazolo [5,4-a] carbazole (48.68 g, yield 48%).

^{1 H-NMR: δ 7.23 (} d, 1H), 7.34 (d, 1H), 7.42 (t, 1H), 7.50 (d, 2H), 7.57 (s, 1H), 8.01 (d, 1H), 8.04 ( d, 2H), 8.12 (d, 1 H), 11.67 (s, 1 H)

<Step 3> Synthesis of 8-bromo-2,10-diphenyl-10H-oxazolo [5,4-a]

Obtained in Step 2 of Preparation Example 6 instead of 7-bromo-2-phenyl-10H-oxazolo [5,4-a] carbazole (47 g, 0.129 mmol) used in Step 6 of Preparation Example 1, bromo-2-phenyl-10H-oxazolo [5,4-a] carbazole (48.68 g, 0.134 mmol) was used in place of 8-bromo -2,10-diphenyl-10H-oxazolo [5,4-a] carbazole (32.38 g, yield 55%).

^{1 H-NMR: δ 7.17 (} d, 1H), 7.23 (d, 1H), 7.41 (t, 1H), 7.45 (t, 1H), 7.50 (d, 4H), 7.58 (d, 2H), 8.04 ( (d, IH), 8.12 (d, IH), 8.32

<Step 4> Synthesis of 8- (2-nitrophenyl) -2,10-diphenyl-10H-oxazolo [5,4-a]

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole used in Step 4 of Preparation Example 1 (149.48 g, 0.465 bromo-2,10-diphenyl-10H-oxazolo [5,4-a] carbazole (32.38 g, 73.71 mmol) obtained in Step 3 of Preparation Example 6 was used instead of 4-bromo- Step 4 of Preparation Example 1 was repeated except that 2-nitrophenylboronic acid (14.76 g, 88.45 mmol) was used instead of -iodo-1-nitrobenzene (138.73 g, 0.423 mol) (2-nitrophenyl) -2,10-diphenyl-10H-oxazolo [5,4-a] carbazole (19.16 g, yield 54%).

^{1 H-NMR: δ 7.23 (} d, 1H), 7.41 (t, 1H), 7.45 (t, 1H), 7.50 (d, 4H), 7.58 (d, 2H), 7.62 (s, 1H), 7.66 ( (d, IH), 8.12 (d, IH), 8.49 (d, IH)

<Step 5> Synthesis of Compound IC-11 and IC-12

Obtained in Step 4 of Preparation Example 6 instead of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (113.7 g, 0.29 mol) used in Step 5 of Preparation Example 1, Step 5 of Preparation Example 1 was repeated except that 2-nitrophenyl-2,10-diphenyl-10H-oxazolo [5,4-a] carbazole (19.16 g, 39.79 mmol) To obtain compound IC-11 (7.33 g, yield 41%) and compound IC-12 (7.15 g, yield 40%).

Compound ¹ H-NMR of the IC-11: δ 7.23 (d , 1H), 7.28 (d, 1H), 7.40 (t, 1H), 7.44 (t, 1H), 7.49 (d, 5H), 7.58 (d, 2H), 7.63 (d, IH), 7.88 (d, IH), 8.04 (d, 2H), 8.11

Compound IC-12 ¹ H-NMR of: δ 7.23 (d, 1H) , 7.28 (d, 1H), 7.41 (m, 2H), 7.45 (t, 1H), 7.50 (d, 5H), 7.55 (s, 1H), 7.58 (d, 2H), 7.63 (d, IH), 7.98 (d, IH), 8.05

[Preparation Example 7] Synthesis of compound IC-13 and IC-14

<Step 1> Synthesis of 7-bromo-2-phenyl-5H-oxazolo [4,5-b] carbazole

Bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (113.7 g, 0.29 mol) used in Step 5 of Preparation Example 1 was used instead of 6- (5-bromo- Bromo-2-phenyl-5H-oxazolo [4] was obtained by following the procedure of Step 5 of Preparation Example 1, except that 2-phenylbenzo [d] oxazole (110.36 g, 0.279 mol) , 5-b] carbazole (43.61 g, yield 43%).

¹ H-NMR:? 7.34 (d, 1 H), 7.40 (m, 2H), 7.50 (d, 2H), 7.55 d, 2H)

<Step 2> Synthesis of 7-bromo-2,5-diphenyl-5H-oxazolo [4,5-b] carbazole

Obtained in Step 1 of Preparation Example 7 instead of 7-bromo-2-phenyl-10H-oxazolo [5,4-a] carbazole (47 g, 0.129 mmol) used in Step 6 of Preparation Example 1, bromo-2-phenyl-5H-oxazolo [4,5-b] carbazole (43.61 g, 0.120 mmol) was used in place of 7-bromo -2,5-diphenyl-5H-oxazolo [4,5-b] carbazole (26.90 g, yield 51%).

^{1 H-NMR: δ 7.17 (} d, 1H), 7.41 (m, 2H), 7.46 (t, 1H), 7.49 (d, 4H), 7.55 (s, 1H), 7.59 (d, 2H), 8.04 ( d, 2 H), 8.32 (d, 1 H), 8.75 (s, 1 H)

<Step 3> Synthesis of 7- (2-nitrophenyl) -2,5-diphenyl-5H-oxazolo [4,5-b]

2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole e used in Step 4 of Preparation Example 1 (149.48 g, Bromo-2,5-diphenyl-5H-oxazolo [4,5-b] carbazole (26.9 g, 61.23 mmol) instead of 4-bromo-2-iodo-1-nitrobenzene , 2-nitrophenylboronic acid (12.27 g, 73.48 mmol) was used instead of 2-nitrophenylboronic acid (0.423 mol) -diphenyl-5H-oxazolo [4,5-b] carbazole (15.33 g, yield 52%).

^{1 H-NMR: δ 7.40 (} m, 2H), 7.46 (t, 1H), 7.50 (d, 2H), 7.52 (d, 2H), 7.55 (s, 1H), 7.58 (d, 2H), 7.62 ( (d, 1H), 7.67 (d, IH), 7.90 (d, IH), 8.00

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

Obtained in Step 3 of Preparation Example 7 was used instead of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (113.7 g, 0.29 mol) used in <Step 4> Step 5 of Preparation Example 1 was repeated except that 2-nitrophenyl-2,5-diphenyl-5H-oxazolo [4,5-b] carbazole (15.33 g, 31.84 mmol) To obtain compound IC-13 (6.15 g, yield 43%) and compound IC-14 (6.01 g, yield 42%).

Compound IC-13 ¹ H-NMR of: δ 7.29 (d, 1H) , 7.41 (m, 3H), 7.45 (t, 1H), 7.50 (d, 3H), 7.53 (d, 2H), 7.56 (s, 2H), 7.58 (d, 2H), 7.64 (d, IH), 8.03

Compound IC-14 ¹ H-NMR of: δ 7.28 (d, 1H) , 7.39 (m, 2H), 7.46 (t, 1H), 7.49 (d, 3H), 7.52 (d, 2H), 7.55 (s, 1H), 7.58 (d, 3H), 7.63 (d, IH), 8.04 (d, 2H), 8.12

[Preparation Example 8] Synthesis of compound IC-15 and IC-16

<Step 1> Synthesis of 5- (4-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole used in Step 4 of Preparation Example 1 (149.48 g, 0.465 benzo [d] oxazole (120 g, 0.374 mol) instead of 2-phenyl-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- except that 4-bromo-1-iodo-2-nitrobenzene (111.37 g, 0.340 mol) was used in place of bromo-2-iodo-1-nitrobenzene (138.73 g, 0.423 mol) 4-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (93.96 g, yield 70%).

^{1 H-NMR: δ 7.40 (} t 1H), 7.50 (d, 2H), 7.79 (d, 1H), 7.85 (d, 1H), 7.94 (d, 1H), 8.04 (d, 3H), 8.09 (s , &Lt; / RTI &gt; 1H), 8.62 (s, 1H)

<Step 2> Synthesis of 7-bromo-2-phenyl-5H-oxazolo [5,4-b] carbazole

Obtained in Step 1 of Preparation Example 8 instead of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (113.7 g, 0.29 mol) used in Step 5 of Preparation Example 1, Bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (93.96 g, 0.238 mol) was used in place of 7-bromo -2-phenyl-5H-oxazolo [5,4-b] carbazole (44.04 g, yield 51%).

^{1 H-NMR: δ 7.34 (} d, 1H), 7.40 (m, 2H), 7.50 (d, 2H), 7.56 (s, 2H), 8.01 (d, 1H), 8.05 (d, 2H), 11.66 ( s, H)

<Step 3> Synthesis of 7-bromo-2,5-diphenyl-5H-oxazolo [5,4-b]

Obtained in Step 2 of Preparation Example 8 instead of 7-bromo-2-phenyl-10H-oxazolo [5,4-a] carbazole (47 g, 0.129 mmol) used in Step 6 of Preparation Example 1, bromo-2-phenyl-5H-oxazolo [5,4-b] carbazole (44.04 g, 0.121 mmol) was used in place of 7-bromo -2,5-diphenyl-5H-oxazolo [5,4-b] carbazole (30.36 g, yield 57%).

^{1 H-NMR: δ 7.34 (} d, 1H), 7.40 (m, 2H), 7.45 (t, 1H), 7.50 (d, 4H), 7.55 (s, 1H), 7.58 (m, 3H), 8.01 ( d, 1 H), 8.04 (d, 2 H), 8.04

<Step 4> Synthesis of 7- (2-nitrophenyl) -2,5-diphenyl-5H-oxazolo [5,4-b]

2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole e used in Step 4 of Preparation Example 1 (149.48 g, Bromo-2,5-diphenyl-5H-oxazolo [5,4-b] carbazole (30.36 g, 69.11 mmol) obtained in Step 3 of Preparation Example 8 was used instead of 4-bromo- Step 4 of Preparation Example 1 was repeated except that 2-nitrophenylboronic acid (13.84 g, 82.93 mmol) was used instead of 2-iodo-1-nitrobenzene (138.73 g, 0.423 mol) - (2-nitrophenyl) -2,5-diphenyl-5H-oxazolo [5,4-b] carbazole (18.30 g, yield 55%).

^{1 H-NMR: δ 7.39 (} m, 2H), 7.45 (t, 1H), 7.50 (d, 4H), 7.54 (s, 1H), 7.57 (d, 2H), 7.62 (s, 1H), 7.67 ( (d, IH), 7.79 (d, IH), 7.90 (d, IH), 8.00

<Step 5> Synthesis of compound IC-15 and IC-16

Obtained in Step 4 of Preparation Example 8 instead of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (113.7 g, 0.29 mol) used in Step 5 of Preparation Example 1, Step 5 of Preparation Example 1 was repeated except that 2-nitrophenyl-2,5-diphenyl-5H-oxazolo [5,4-b] carbazole (18.30 g, 38.01 mmol) To obtain compound IC-15 (6.49 g, yield 38%) and compound IC-16 (5.98 g, yield 35%).

Compound IC-15 ¹ H-NMR of: δ 7.29 (d, 1H) , 7.39 (m, 2H), 7.44 (t, 1H), 7.49 (d, 5H), 7.54 (s, 1H), 7.58 (d, 1H), 7.62 (d, 1H), 8.07 (d, 2H), 8.11 (d, 2H), 11.68

Compound IC-16 ¹ H-NMR of: δ 7.28 (d, 1H) , 7.40 (m, 3H), 7.46 (t, 1H), 7.51 (d, 5H), 7.55 (m, 2H), 7.59 (d, 2H), 7.64 (d, IH), 8.07 (d, 3H), 11.67 (s, IH)

[Preparation Example 9] Synthesis of compound IC-17 and IC-18

<Step 1> Synthesis of 8-bromo-2-phenyl-10H-oxazolo [4,5-a]

Bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (113.7 g, 0.29 mol) used in Step 5 of Preparation Example 1 was used instead of 6- (5-bromo- Bromo-2-phenyl-10H-oxazolo [4, 5-d] pyrimidine was prepared by following the procedure of Step 5 of Preparation Example 1, except that 2-phenylbenzo [d] oxazole , 5-a] carbazole (38.60 g, yield 42%).

^{1 H-NMR: δ 7.00 (} d, 1H), 7.34 (d, 1H), 7.40 (t, 1H), 7.50 (d, 2H), 7.57 (s, 1H), 8.01 (d, 1H), 8.06 ( d, 2 H), 8.11 (d, 1 H), 11.69 (s, 1 H)

<Step 2> Synthesis of 8-bromo-2,10-diphenyl-10H-oxazolo [4,5-a] carbazole

Obtained in Step 1 of Preparation Example 9 instead of 7-bromo-2-phenyl-10H-oxazolo [5,4-a] carbazole (47 g, 0.129 mmol) used in Step 6 of Preparation Example 1, bromo-2-phenyl-10H-oxazolo [4,5-a] carbazole (38.60 g, 0.106 mmol) was used in place of 8-bromo -2,10-diphenyl-10H-oxazolo [4,5-a] carbazole (23.34 g, yield 50%).

^{1 H-NMR: δ 7.00 (} d, 1H), 7.17 (d, 1H), 7.40 (t, 1H), 7.46 (t, 1H), 7.50 (d, 4H), 7.58 (d, 2H), 8.04 ( (d, 2H), 8.13 (d, 1H), 8.32 (d,

<Step 3> Synthesis of 8- (2-nitrophenyl) -2,10-diphenyl-10H-oxazolo [4,5-a]

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole used in Step 4 of Preparation Example 1 (149.48 g, 0.465 bromo-2,10-diphenyl-10H-oxazolo [4,5-a] carbazole (23.34 g, 53.13 mmol) obtained in Step 2 of Preparation Example 9 was used instead of 4-bromo- Step 4 of Preparation Example 1 was repeated except that 2-nitrophenylboronic acid (10.64 g, 63.76 mmol) was used in place of -iodo-1-nitrobenzene (138.73 g, 0.423 mol) (2-nitrophenyl) -2,10-diphenyl-10H-oxazolo [4,5-a] carbazole (14.07 g, yield 55%).

^{1 H-NMR: δ 7.01 (} d, 1H), 7.39 (t, 1H), 7.44 (t, 1H), 7.49 (d, 4H), 7.57 (d, 2H), 7.62 (s, 1H), 7.66 ( (d, IH), 7.90 (d, IH), 8.00 (d, IH), 8.06 (d,

<Step 4> Synthesis of Compound IC-17 and IC-18

Obtained in Step 3 of Preparation Example 9 instead of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (113.7 g, 0.29 mol) used in Step 5 of Preparation Example 1, Step 5 of Preparation Example 1 was repeated except that 2-nitrophenyl-2,10-diphenyl-10H-oxazolo [4,5-a] carbazole (14.07 g, 29.22 mmol) To obtain compound IC-17 (5.78 g, yield 44%) and compound IC-18 (5.12 g, yield 39%).

Compound IC-17 ¹ H-NMR of: δ 7.00 (d, 1H) , 7.29 (d, 1H), 7.40 (m, 2H), 7.44 (t, 1H), 7.49 (d, 5H), 7.56 (d, 1H), 7.62 (d, 1H), 8.06 (d, 2H), 8.10 (d, 2H), 11.67

Compound ¹ H-NMR of the IC-18: δ 7.00 (d , 1H), 7.29 (d, 1H), 7.38 (t, 1H), 7.44 (t, 1H), 7.51 (d, 5H), 7.57 (d, 3H), 7.62 (d, IH), 8.05 (d, 2H), 8.11

[Preparation Example 10] Synthesis of compound IC-19 and IC-20

<Step 1> Synthesis of 4- (4-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole used in Step 4 of Preparation Example 1 (149.48 g, 0.465 d] oxazole (100 g, 0.311 mol) instead of 2-phenyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- except that 4-bromo-1-iodo-2-nitrobenzene (92.81 g, 0.283 mol) was used in place of bromo-2-iodo-1-nitrobenzene (138.73 g, 0.423 mol) (4-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (80.54 g, yield 72%) was obtained.

^{1 H-NMR: δ 7.40 (} t, 1H), 7.50 (m, 3H), 7.75 (d, 1H), 7.79 (d, 1H), 7.94 (d, 1H), 8.05 (d, 3H), 8.63 ( s, 1 H)

<Step 2> Synthesis of 8-bromo-2-phenyl-6H-oxazolo [5,4-c]

Obtained in Step 1 of Preparation Example 10 instead of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (113.7 g, 0.29 mol) used in Step 5 of Preparation Example 1, Step 5 of Preparation Example 1 was repeated except that 4-bromo-2-nitrophenyl-2-phenylbenzo [d] oxazole (80.54 g, 0.204 mol) -2-phenyl-6H-oxazolo [5,4-c] carbazole (42.19 g, yield 57%).

^{1 H-NMR: δ 7.08 (} d, 1H), 7.34 (d, 1H), 7.40 (t, 1H), 7.50 (d, 2H), 7.57 (s, 1H), 7.63 (d, 1H), 8.01 ( d, 1 H), 8.04 (d, 2H), 11.66 (s, 1 H)

<Step 3> Synthesis of 8-bromo-2,6-diphenyl-6H-oxazolo [5,4-c]

Obtained in Step 2 of Preparation Example 10 instead of 7-bromo-2-phenyl-10H-oxazolo [5,4-a] carbazole (47 g, 0.129 mmol) used in Step 6 of Preparation Example 1, 6-bromo-2-phenyl-6H-oxazolo [5,4-c] carbazole (42.19 g, 0.116 mmol) -2,6-diphenyl-6H-oxazolo [5,4-c] carbazole (26.02 g, yield 51%).

^{1 H-NMR: δ 7.08 (} d, 1H), 7.17 (d, 1H), 7.40 (t, 1H), 7.44 (d, 1H), 7.50 (d, 4H), 7.57 (d, 2H), 7.62 ( (d, IH), 8.04 (d, 2H), 8.33 (d, IH), 8.77

Step 4 Synthesis of 8- (2-nitrophenyl) -2,6-diphenyl-6H-oxazolo [5,4-c] carbazole

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole used in Step 4 of Preparation Example 1 (149.48 g, 0.465 bromo-2,6-diphenyl-6H-oxazolo [5,4-c] carbazole (26.02 g, 59.23 mmol) obtained in Step 3 of Preparation Example 10 was used instead of 4-bromo- Step 4 of Preparation Example 1 was repeated except that 2-nitrophenylboronic acid (11.86 g, 71.08 mmol) was used instead of -iodo-1-nitrobenzene (138.73 g, 0.423 mol) (2-nitrophenyl) -2,6-diphenyl-6H-oxazolo [5,4-c] carbazole (17.11 g, yield 60%).

^{1 H-NMR: δ 7.08 (} d, 1H), 7.41 (t, 1H), 7.45 (t, 1H), 7.51 (d, 4H), 7.57 (d, 2H), 7.63 (m, 2H), 7.69 ( (d, IH), 7.90 (d, IH), 8.00 (d, IH), 8.05

<Step 5> Synthesis of Compound IC-19 and IC-20

Obtained in Step 4 of Preparation Example 10 instead of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (113.7 g, 0.29 mol) used in Step 5 of Preparation Example 1, Step 5 of Preparation Example 1 was repeated except that 2-nitrophenyl 2,6-diphenyl-6H-oxazolo [5,4-c] carbazole (17.11 g, 35.54 mmol) To obtain compound IC-19 (7.35 g, yield 46%) and compound IC-20 (7.19 g, yield 45%).

Compound IC-19 ¹ H-NMR of: δ 7.07 (d, 1H) , 7.30 (d, 1H), 7.42 (t, 1H), 7.46 (t, 1H), 7.52 (d, 5H), 7.58 (d, 2H), 8.16 (d, 2H), 7.63 (d,

^One of the compounds IC-20 H-NMR: δ 7.09 (d, 1H), 7.28 (d, 1H), 7.40 (m, 2H), 7.45 (t, 1H), 7.51 (d, 5H), 7.56 (m, (S, 3H), 7.62 (d, 2H), 8.05 (d, 2H), 8.11

[Preparation Example 11] Synthesis of compound IC-21 and IC-22

<Step 1> Synthesis of N- (2,4-dibromophenyl) benzothioamide

N- (2,4-dibromophenyl) benzamide (200 g, 0.56 mol) was added to the reactor, and toluene (2500 ml) was added thereto and stirred. Lawesson's reagent (172.14 g, 0.39 mol) was added dropwise to the reactor and mixed, followed by stirring at 110 ° C for 4 hours.

After the reaction was completed, the organic layer was extracted with methylene chloride, the water was removed with MgSO ₄ , and the residue was purified by column chromatography (Hexane: EA = 7: 1 (v / v)) to give N- (2,4-dibromophenyl) benzothioamide (192.33 g, yield 92%).

^{1 H-NMR: δ 6.41 (} d, 1H), 7.29 (d, 1H), 7.44-7.45 (m, 3H), 7.75 (s, 1H), 7.98 (d, 2H), 8.59 (b, 1H)

<Step 2> Synthesis of 6-bromo-2-phenylbenzo [d] thiazole

Preparation Example 1 <Step 2> The N- (2,4-dibromophenyl) benzamide ( 258.72 g, 0.73 mol) in the use of N- (2,4-dibromophenyl) benzothioamide ( 192.32 g, 518.26 mmol) instead of 6-bromo-2-phenylbenzo [d] thiazole (106.78 g, yield 71%) was obtained in the same manner as in <Step 2> of Preparation Example 1,

^{1 H-NMR: δ 7.41 (} t, 1H) 7.51 (dd, 2H), 7.64 (d, 1H), 7.72 (d, 1H), 8.03 (d, 2H), 8.83 (s, 1H)

Synthesis of 2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] thiazole

Bromo-2-phenylbenzo [d] thiazole obtained in Step 2 of Preparation Example 11 was used instead of 6-bromo-2-phenylbenzo [d] oxazole (161.48 g, 0.589 mol) used in Step 3 of Preparation Example 1, thiazole (106.78 g, 0.367.98 mol) was used in place of 2-phenyl-6- (4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl) benzo [d] thiazole (93.07 g, yield 75%).

^{1 H-NMR: δ 1.24 (} s, 12H) 7.38 (d, 1H), 7.41 (t, 1H), 7.51 (dd, 2H), 7.75 (d, 1H), 7.95 (s, 1H), 8.03 (d , 2H)

<Step 4> Synthesis of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] thiazole

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole used in Step 4 of Preparation Example 1 (149.48 g, 0.465 instead of 2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] thiazole (obtained in Step 3 of Preparation Example 11 2-nitrophenyl) -2-phenylbenzo [d] thiazole (65 g, 0.276 mol) was used in the same manner as Step 4 of Preparation Example 1, Yield: 63%).

^{1 H-NMR: δ 7.41 (} t, 1H), 7.51 (dd, 2H), 7.72 (s, 1H), 7.77 (d, 1H), 7.81 (d, 1H), 7.98 (d, 1H), 8.03 ( d, 2 H), 8.21 (d, 1 H), 8.34 (s, 1 H)

Step 5 Synthesis of 7-bromo-2-phenyl-10H-thiazolo [5,4-a]

Obtained in Step 4 of Preparation Example 11 instead of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (113.7 g, 0.29 mol) used in Step 5 of Preparation Example 1, Step 5 of Preparation Example 1 was repeated except that 5-bromo-2-nitrophenyl-2-phenylbenzo [d] thiazole (65 g, 0.158 mol) -2-phenyl-10H-thiazolo [5,4-a] carbazole (25.18 g, yield 42%).

¹ H-NMR:? 7.41-7.42 (m, 2H), 7.51-7.55 (m, 4H), 7.75

Step 6 Synthesis of 7-bromo-2,10-diphenyl-10H-thiazolo [5,4-a] carbazole

Obtained in Step 5 of Preparation Example 11 instead of 7-bromo-2-phenyl-10H-oxazolo [5,4-a] carbazole (47 g, 0.129 mol) used in Step 6 of Preparation Example 1, bromo-2-phenyl-10H-thiazolo [5,4-a] carbazole (25.18 g, 66.39 mmol) was used in place of 7-bromo -2,10-diphenyl-10H-thiazolo [5,4-a] carbazole (14.18 g, yield 49%).

^{1 H-NMR: δ 7.25 (} d, 1H), 7.41 (t, 1H), 7.46 (t, 1H), 7.50 (d, 4H), 7.55 (d, 1H), 7.58 (d, 2H), 7.72 ( s), 7.75 (d, IH), 7.83 (d, IH), 8.03

<Step 7> Synthesis of 7- (2-nitrophenyl) -2,10-diphenyl-10H-thiazolo [5,4-a]

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole used in Step 4 of Preparation Example 1 (149.48 g, 0.465 bromo-2,10-diphenyl-10H-thiazolo [5,4-a] carbazole (14.81 g, 32.52 mmol) obtained in Step 6 of Preparation Example 11 was used instead of 4-bromo- Step 4 of Preparation Example 1 was repeated except that 2-nitrophenylboronic acid (6.51 g, 39.03 mmol) was used in place of -iodo-1-nitrobenzene (138.73 g, 0.423 mol) (2-nitrophenyl) -2,10-diphenyl-10H-thiazolo [5,4-a] carbazole (8.41 g, yield 52%).

^{1 H-NMR: δ 7.40 (} t, 1H), 7.46 (t, 1H), 7.51 (d, 4H), 7.55 (d, 1H), 7.59 (d, 2H), 7.67 (d, 1H), 7.75 ( (d, IH), 7.77 (s, IH), 7.90 (d, IH), 8.00

<Step 8> Synthesis of Compound IC-21 and IC-22

Obtained in Step 7 of Preparation Example 11 instead of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (113.7 g, 0.29 mol) used in <Step 5> Step 5 of Preparation Example 1 was repeated except that 2-nitrophenyl-2,10-diphenyl-10H-thiazolo [5,4-a] carbazole (8.41 g, 16.9 mmol) To obtain compound IC-21 (3.23 g, yield 41%) and compound IC-22 (3.15 g, yield 40%).

Compound IC-21 ¹ H-NMR of: δ 7.29 (d, 1H) , 7.41 (m, 2H), 7.45 (t, 1H), 7.50 (d, 5H), 7.55 (m, 2H), 7.60 (d, 2H), 7.64 (d, IH), 7.76 (d, IH), 8.04

^One of the compounds IC-22 H-NMR: δ 7.28 (d, 1H), 7.40 (t, 1H), 7.46 (t, 1H), 7.50 (d, 5H), 7.56 (d, 1H), 7.57 (d, 2H), 7.75 (d, 1H), 7.95 (d, 2H), 7.64 (d,

[Preparation Example 12] Synthesis of compounds IC-23 and IC-24

<Step 1> Synthesis of 8-bromo-2-phenyl-5H-thiazolo [4,5-b] carbazole

Bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (113.7 g, 0.29 mol) used in Step 5 of Preparation Example 1 was used instead of 6- (5-bromo- Bromo-2-phenyl-5H-thiazolo [4, 5] thiazole was obtained by following the procedure of Step 5 of Preparation Example 1, except that 2-phenylbenzo [d] thiazole , 5-b] carbazole (20.75 g, yield 45%).

^{1 H-NMR: δ 7.41 (} m, 2H), 7.52 (d, 3H), 8.01 (d, 2H), 8.05 (s, 1H), 8.12 (s, 1H), 8.23 (s, 1H), 11.68 ( s, 1 H)

<Step 2> Synthesis of 8-bromo-2,5-diphenyl-5H-thiazolo [4,5-b] carbazole

Obtained in Step 1 of Preparation Example 12 instead of 7-bromo-2-phenyl-10H-oxazolo [5,4-a] carbazole (47 g, 0.129 mol) used in Step 6 of Preparation Example 1, bromo-2-phenyl-5H-thiazolo [4,5-b] carbazole (20.75 g, 54.71 mmol) was used in place of 8-bromo -2,5-diphenyl-5H-thiazolo [4,5-b] carbazole (12.95 g, yield 52%).

^{1 H-NMR: δ 7.23 (} d, 1H), 7.42 (t, 1H), 7.47 (t, 1H), 7.51 (d, 4H), 7.58 (d, 2H), 7.71 (s, 1H), 7.82 ( (d, IH), 8.02 (d, 2H), 8.13 (s, IH), 8.24

<Step 3> Synthesis of 8- (2-nitrophenyl) -2,5-diphenyl-5H-thiazolo [4,5-b] carbazole

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole used in Step 4 of Preparation Example 1 (149.48 g, 0.465 bromo-2,5-diphenyl-5H-thiazolo [4,5-b] carbazole (12.95 g, 28.44 mmol) obtained in Step 2 of Preparation Example 12 was used instead of 4-bromo- Step 4 of Preparation Example 1 was repeated except that 2-nitrophenylboronic acid (5.7 g, 34.13 mmol) was used instead of -iodo-1-nitrobenzene (138.73 g, 0.423 mol) (2-nitrophenyl) -2,5-diphenyl-5H-thiazolo [4,5-b] carbazole (7.22 g, yield 51%).

^{1 H-NMR: δ 7.42 (} t, 1H), 7.47 (t, 1H), 7.51 (d, 4H), 7.58 (d, 2H), 7.67 (d, 1H), 7.77 (s, 1H), 7.91 ( (d, IH), 8.01 (d, 4H), 8.05 (d, IH), 8.13

<Step 4> Synthesis of compounds IC-23 and IC-24

Obtained in Step 3 of Preparation Example 12 instead of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (113.7 g, 0.29 mol) used in Step 5 of Preparation Example 1, Step 5 of Preparation Example 1 was repeated except that 2-nitrophenyl-2,5-diphenyl-5H-thiazolo [4,5-b] carbazole (7.22 g, 14.51 mmol) To obtain compound IC-23 (2.84 g, yield 42%) and compound IC-24 (2.7 g, yield 40%).

Compound IC-23 ¹ H-NMR of: δ 7.27 (d, 1H) , 7.39 (s, 1H), 7.42 (t, 1H), 7.47 (t, 1H), 7.51 (d, 5H), 7.54 (s, 1H), 7.54 (d, 2H), 7.63 (s, 1H), 8.01 (d, 2H), 8.13

The compounds of the ^{IC-24 1 H-NMR:} δ 7.41 (t, 1H), 7.48 (t, 1H), 7.51 (d, 5H), 7.58 (d, 2H), 7.62 (d, 1H), 7.68 (d, 1H), 7.29 (d, 1H), 8.02 (d, 3H), 8.12 (m, 2H), 8.23

[Synthesis Example 1] Synthesis of Compound Inv-3

(3 g, 6.67 mmol), 2- (3-chlorophenyl) triphenylene (2.71 g, 8.01 mmol) and Pd (OAc) ₂ (0.07 g, 5 mol%) synthesized in Preparation Example 1, (1.92 g, 20.02 mmol), P (t-bu) ₃ (0.14 g, 0.67 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C for 12 hours.

After the reaction was completed, the organic layer was extracted with ethyl acetate, the organic layer was dried over MgSO ₄ and purified by column chromatography (Hexane: EA = 5: 1 (v / v) 3.46 g, yield 69%).

GC-Mass (calculated: 751.26 g / mol, measured: 751 g / mol)

[Synthesis Example 2] Synthesis of compound Inv-11

Except that 1-chloro-4-phenylisoquinoline (1.92 g, 8.01 mmol) was used in place of 2- (3-chlorophenyl) triphenylene (2.71 g, 8.01 mmol) used in Synthesis Example 1 (3.18 g, yield 73%) of the compound Inv-11.

GC-Mass (calculated: 652.23 g / mol, measured: 652 g / mol)

[Synthesis Example 3] Synthesis of compound Inv-23

Except that 4-chloro-2-phenylpyrimidine (1.53 g, 8.01 mmol) was used instead of 2- (3-chlorophenyl) triphenylene (2.71 g, 8.01 mmol) used in Synthesis Example 1 Was performed to obtain the compound Inv-23 (2.90 g, yield 72%).

GC-Mass (theory: 603.21 g / mol, measured: 603 g / mol)

[Synthesis Example 4] Synthesis of Compound Inv-28

4-bromobiphenyl-3-carbonitrile (2.58 g, 10.01 mmol), Cu powder (0.04 g, 0.67 mmol), K ₂ CO ₃ (0.92 g, 6.67 mmol), Na ₂ SO ₄ (0.95 g, 6.67 mmol) and nitrobenzene (100 ml) were mixed and stirred at 200 ° C for 24 hours.

After termination of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed from the organic layer using MgSO ₄ . The solvent was removed from the organic layer from which water had been removed, and then purified by column chromatography (Hexane: EA = 5: 1 (v / v)) to obtain Compound Inv-28 (2.17 g, yield 52%).

GC-Mass (calculated: 626.21 g / mol, measured: 626 g / mol)

[Synthesis Example 5] Synthesis of Compound Inv-39

The compound IC-1 (3 g, 6.67 mmol) synthesized in Preparation Example 1 under nitrogen was dissolved in 100 ml of DMF. NaH (0.40 g, 16.69 mmol) was added thereto and stirred for 1 hour. 2-chloro-4,6-diphenyl-1,3,5-triazine (3.57 g, 13.35 mmol) dissolved in DMF (100 ml) was slowly added thereto. After stirring for 3 hours, the reaction was terminated, the mixture was filtered through silica, washed with water and methanol, and then the solvent was removed. The solvent-removed solid product was purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain Compound Inv-39 (2.00 g, yield 44%).

GC-Mass (calculated: 680.23 g / mol, measured: 680 g / mol)

[Synthesis Example 6] Synthesis of Compound Inv-54

Except that the compound IC-2 (3 g, 6.67 mmol) synthesized in Preparation Example 1 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4, and 2.58 g of 4'-bromobiphenyl-3-carbonitrile The same procedure as in Synthesis Example 4 was carried out except that 3-bromo-9-phenyl-9H-carbazole (3.23 g, 10.01 mmol) was used in place of the compound (Inv-54, 50%).

GC-Mass (calculated: 690.79 g / mol, measured: 690 g / mol)

[Synthesis Example 7] Synthesis of Compound Inv-66

2- (3-chlorophenyl) triphenylene (2.71 g, 6.67 mmol) was used instead of the compound IC-2 (3 g, 6.67 mmol) synthesized in Preparation Example 1 in place of the compound IC- , Inv-66 (2.51 g, yield 65%) was obtained by following the same procedure as in Synthesis Example 1, except that 2-chloroquinazoline (1.32 g, 8.01 mmol)

GC-Mass (calculated: 577.19 g / mol, measured: 577 g / mol)

[Synthesis Example 8] Synthesis of Compound Inv-79

Except that the compound IC-2 (3 g, 6.67 mmol) synthesized in Preparation Example 1 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4, and 2.58 g of 4'-bromobiphenyl-3-carbonitrile Inv-79 (2.01 g, yield 48%) was obtained by following the same procedure as in Synthesis Example 4, except that 4'-bromobiphenyl-4-carbonitrile (2.58 g, 10.01 mmol) .

GC-Mass (calculated: 626.21 g / mol, measured: 626 g / mol)

[Synthesis Example 9] Synthesis of Compound Inv-81

Instead of 2- (3-chlorophenyl) triphenylene (2.71 g, 8.01 mmol) was used instead of compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 1 instead of IC- Inv-81 (2.74 g, yield 68%) was obtained by following the same procedure as in Synthesis Example 1, except that chloro-3,3'-bipyridine (1.53 g, 8.01 mmol) was used.

GC-Mass (theory: 603.21 g / mol, measured: 603 g / mol)

[Synthesis Example 10] Synthesis of Compound Inv-113

Except that the compound IC-3 (3 g, 6.67 mmol) synthesized in Preparation Example 2 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4 and 2.58 g of 4'-bromobiphenyl-3-carbonitrile , Inv-113 (2.05 g, yield 51%) was obtained by following the same procedure as in Synthesis Example 4, except that 6-bromo-2,3'-bipyridine (2.35 g, 10.01 mmol) %).

GC-Mass (theory: 603.21 g / mol, measured: 603 g / mol)

[Synthesis Example 11] Synthesis of Compound Inv-125

Except that the compound IC-3 (3 g, 6.67 mmol) synthesized in Preparation Example 2 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4 and 2.58 g of 4'-bromobiphenyl-3-carbonitrile , Inv-125 (2.54 g, yield 55%) was obtained by following the same procedure as in Synthesis Example 4, except that 3-bromo-N, N-diphenylaniline (3.25 g, 10.01 mmol) ).

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

[Synthesis Example 12] Synthesis of compound Inv-145

2- (3-chlorophenyl) triphenylene (2.71 g, 6.67 mmol) was used instead of the compound IC-4 (3 g, 6.67 mmol) synthesized in Preparation Example 2 in place of the compound IC- , Inv-145 (2.78 g, yield 69%) was obtained by following the same procedure as in Synthesis Example 1, except that 4-chloro-2-phenylpyrimidine (1.53 g, 8.01 mmol) .

GC-Mass (theory: 603.21 g / mol, measured: 603 g / mol)

[Synthesis Example 13] Synthesis of Compound Inv-152

2- (3-chlorophenyl) triphenylene (2.71 g, 6.67 mmol) was used instead of the compound IC-4 (3 g, 6.67 mmol) synthesized in Preparation Example 2 in place of the compound IC- (3.27 g, yield 72%) was obtained by following the same procedure as in Synthesis Example 1, except that 2-chloro-4,6-diphenylpyrimidine (2.14 g, 8.01 mmol) ).

GC-Mass (calculated: 679.24 g / mol, measured: 679 g / mol)

[Synthesis Example 14] Synthesis of compound Inv-173

Except that the compound IC-5 (3 g, 6.67 mmol) synthesized in Preparation Example 3 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthetic Example 4 and 4'-bromobiphenyl-3-carbonitrile , Inv-173 (1.97 g, yield 49%) was obtained by following the same procedure as in Synthesis Example 4, except that 6-bromo-2,3'-bipyridine (2.35 g, 10.01 mmol) %).

GC-Mass (theory: 603.21 g / mol, measured: 603 g / mol)

[Synthesis Example 15] Synthesis of compound Inv-179

(3 g, 6.67 mmol) was used instead of the compound IC-5 (3 g, 6.67 mmol) used in Synthesis Example 1, and 2- (3-chlorophenyl) triphenylene , Inv-179 (2.72 g, yield 65%) was obtained in the same manner as in Synthesis Example 1, except that 3'-chlorobiphenyl-4-carbonitrile (1.71 g, 8.01 mmol) .

GC-Mass (calculated: 626.21 g / mol, measured: 626 g / mol)

[Synthesis Example 16] Synthesis of Compound Inv-211

Except that the compound IC-6 (3 g, 6.67 mmol) synthesized in Preparation Example 3 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4 and 2.58 g of 4'-bromobiphenyl-3-carbonitrile , Inv-211 (2.40 g, yield 53%) was obtained by following the same procedure as in Synthesis Example 4, except that 2-bromo-4,6-diphenylpyridine (3.11 g, 10.01 mmol) ).

GC-Mass (theory: 678.24 g / mol, measured: 678 g / mol)

[Synthesis Example 17] Synthesis of Compound Inv-219

Except that the compound IC-6 (3 g, 6.67 mmol) synthesized in Preparation Example 3 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4 and 2.58 g of 4'-bromobiphenyl-3-carbonitrile , Inv-219 (1.98 g, yield 54%) was obtained by following the same procedure as in Synthesis Example 4, except that 3-bromobenzonitrile (1.82 g, 10.01 mmol)

GC-Mass (calculated: 550.18 g / mol, measured: 550 g / mol)

[Synthesis Example 18] Synthesis of Compound Inv-230

(3 g, 6.67 mmol) prepared in Preparation Example 4 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 1 and 2- (3-chlorophenyl) triphenylene , Inv-230 (3.16 g, yield 82%) was obtained in the same manner as in Synthesis Example 1, except that 2-chloroquinoline (1.31 g, 8.01 mmol)

GC-Mass (calculated: 576.20 g / mol, measured: 576 g / mol)

[Synthesis Example 19] Synthesis of compound Inv-236

2- (3-chlorophenyl) triphenylene (2.71 g, 6.67 mmol) prepared in Preparation Example 4 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 1, The same procedure as in Synthesis Example 1 was carried out except that 4-chloro-2- (pyridin-3-yl) pyrimidine (1.53 g, 8.01 mmol) , Yield: 69%).

GC-Mass (theory: 604.20 g / mol, measured: 604 g / mol)

[Synthesis Example 20] Synthesis of Compound Inv-274

2- (3-chlorophenyl) triphenylene (2.71 g, 6.67 mmol) was used instead of the compound IC-8 (3 g, 6.67 mmol) synthesized in Preparation Example 4 instead of the compound IC- , Inv-274 (3.31 g, yield 73%) was obtained by following the same procedure as in Synthesis Example 1, except that 4-chloro-2,6-diphenylpyrimidine (2.14 g, 8.01 mmol) ).

GC-Mass (calculated: 679.24 g / mol, measured: 679 g / mol)

[Synthesis Example 21] Synthesis of Compound Inv-280

Except that the compound IC-8 (3 g, 6.67 mmol) synthesized in Preparation Example 4 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4 and 2.58 g of 4'-bromobiphenyl-3-carbonitrile , Inv-280 (1.91 g, yield 52%) was obtained by following the same procedure as in Synthesis Example 4, except that 4-bromobenzonitrile (1.82 g, 10.01 mmol)

GC-Mass (calculated: 550.18 g / mol, measured: 550 g / mol)

[Synthesis Example 22] Synthesis of compound Inv-287

Except that the compound IC-9 (3 g, 6.67 mmol) synthesized in Preparation Example 5 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4, and 2.58 g of 4'-bromobiphenyl-3-carbonitrile The same procedure as in Synthesis Example 4 was carried out, except that 9- (4-bromophenyl) -9H-carbazole (3.23 g, 10.01 mmol) 56%).

GC-Mass (theory: 690.24 g / mol, measured: 690 g / mol)

[Synthesis Example 23] Synthesis of compound Inv-288

(3 g, 6.67 mmol) was used instead of the compound IC-9 (3 g, 6.67 mmol) used in Synthesis Example 1 and 2- (3-chlorophenyl) triphenylene , Inv-288 (2.88 g, yield 66%) was obtained by following the same procedure as in Synthesis Example 1, except that 1-chloro-4-phenylisoquinoline (1.92 g, 8.01 mmol) .

GC-Mass (calculated: 652.23 g / mol, measured: 652 g / mol)

[Synthesis Example 24] Synthesis of Compound Inv-322

Except that the compound IC-11 (3 g, 6.67 mmol) synthesized in Preparation Example 6 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4, and 2.58 g of 4'-bromobiphenyl-3-carbonitrile , Inv-322 (1.77 g, yield 44%) was obtained by following the same procedure as in Synthesis Example 4, except that 2-bromo-6-phenylpyridine (2.34 g, 10.01 mmol) .

GC-Mass (theory: 602.21 g / mol, measurement: 602 g / mol)

[Synthesis Example 25] Synthesis of compound Inv-338

(3 g, 6.67 mmol) prepared in Preparation Example 6 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 1 and 2- (3-chlorophenyl) triphenylene , 8.01 mmol) instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (2.75 g, 8.01 mmol) To obtain Compound Inv-338 (3.89 g, yield 77%).

GC-Mass (calculated: 756.26 g / mol, measured: 756 g / mol)

[Synthesis Example 26] Synthesis of compound Inv-353

Except that the compound IC-12 (3 g, 6.67 mmol) synthesized in Preparation Example 6 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4, and 2.58 g of 4'-bromobiphenyl-3-carbonitrile , Inv-353 (1.61 g, yield 40%) was obtained by following the same procedure as in Synthesis Example 4, except that 6-bromo-2,3'-bipyridine (2.35 g, 10.01 mmol) %).

GC-Mass (theory: 603.21 g / mol, measured: 603 g / mol)

[Synthesis Example 27] Synthesis of compound Inv-364

Except that the compound IC-12 (3 g, 6.67 mmol) synthesized in Preparation Example 6 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 1 and 2- (3-chlorophenyl) triphenylene , Inv-364 (3.40 g, yield 75%) was obtained by following the same procedure as in Synthesis Example 1, except that 4-chloro-2,6-diphenylpyrimidine (2.14 g, 8.01 mmol) ).

GC-Mass (calculated: 679.24 g / mol, measured: 679 g / mol)

[Synthesis Example 28] Synthesis of Compound Inv-388

Except that the compound IC-13 (3 g, 6.67 mmol) synthesized in Preparation Example 7 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4 and 2.58 g of 4'-bromobiphenyl-3-carbonitrile , Inv-388 (1.92 g, yield 46%) was obtained by following the same procedure as in Synthesis Example 4, except that 4'-bromobiphenyl-4-carbonitrile (2.58 g, 10.01 mmol) .

GC-Mass (calculated: 626.21 g / mol, measured: 626 g / mol)

[Synthesis Example 29] Synthesis of compound Inv-397

(3 g, 6.67 mmol) was used instead of the compound IC-13 (3 g, 6.67 mmol) used in Synthesis Example 1, and 2- (3-chlorophenyl) triphenylene , 8.01 mmol) instead of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (2.75 g, 8.01 mmol) To obtain Compound Inv-397 (3.84 g, yield 76%).

GC-Mass (calculated: 756.26 g / mol, measured: 756 g / mol)

[Synthesis Example 30] Synthesis of compound Inv-413

Except that the compound IC-14 (3 g, 6.67 mmol) synthesized in Preparation Example 7 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4 and 2.58 g of 4'-bromobiphenyl-3-carbonitrile , Inv. 413 (1.66 g, yield 41%) was obtained by following the same procedure as in Synthesis Example 4, except that 6-bromo-2,3'-bipyridine (2.35 g, 10.01 mmol) %).

GC-Mass (theory: 606.21 g / mol, measurement: 606 g / mol)

[Synthesis Example 31] Synthesis of Compound Inv-430

Except that the compound IC-14 (3 g, 6.67 mmol) synthesized in Preparation Example 7 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4 and 2.58 g of 4'-bromobiphenyl-3-carbonitrile , Inv-430 (1.76 g, yield 48%) was obtained by following the same procedure as in Synthesis Example 4, except that 4-bromobenzonitrile (1.82 g, 10.01 mmol) was used instead of 4-

GC-Mass (calculated: 550.18 g / mol, measured: 550 g / mol)

[Synthesis Example 32] Synthesis of Compound Inv-440

(3-chlorophenyl) triphenylene (2.71 g, 6.67 mmol) was used instead of the compound IC-15 (3 g, 6.67 mmol) synthesized in Preparation Example 8, instead of the compound IC- , Inv-440 (2.58 g, yield 67%) was obtained in the same manner as in Synthesis Example 1, except that 2-chloroquinoline (1.31 g, 8.01 mmol)

GC-Mass (calculated: 576.20 g / mol, measured: 576 g / mol)

[Synthesis Example 33] Synthesis of compound Inv-452

(3-chlorophenyl) triphenylene (2.71 g, 6.67 mmol) was used instead of the compound IC-15 (3 g, 6.67 mmol) synthesized in Preparation Example 8, instead of the compound IC- , Inv-452 (3.45 g, yield 76%) was obtained by following the same procedure as in Synthesis Example 1, except that 2-chloro-4,6-diphenylpyrimidine (2.14 g, 8.01 mmol) ).

GC-Mass (calculated: 679.24 g / mol, measured: 679 g / mol)

[Synthesis Example 34] Synthesis of compound Inv-462

Except that the compound IC-16 (3 g, 6.67 mmol) synthesized in Preparation Example 8 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4, and 2.58 g of 4'-bromobiphenyl- , Inv-462 (2.09 g, yield 52%) was obtained by following the same procedure as in Synthesis Example 4, except that 3-bromobiphenyl (2.33 g, 10.01 mmol)

GC-Mass (theory: 601.22 g / mol, measurement: 601 g / mol)

[Synthesis Example 35] Synthesis of compound Inv-487

2- (3-chlorophenyl) triphenylene (2.71 g, 6.67 mmol) was used instead of the compound IC-16 (3 g, 6.67 mmol) synthesized in Preparation Example 8 instead of the compound IC- , 8.01 mmol) instead of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (2.75 g, 8.01 mmol) To obtain Compound Inv-487 (3.74 g, yield 74%).

GC-Mass (calculated: 756.26 g / mol, measured: 756 g / mol)

[Synthesis Example 36] Synthesis of Compound Inv-510

(3 g, 6.67 mmol) synthesized in Preparation Example 9 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 1 and 2- (3-chlorophenyl) triphenylene (3.18 g, yield: 98%) was obtained by following the same procedure as in Synthesis Example 1, except that 2- (4-chlorophenyl) -4-phenylpyrimidine (2.14 g, 8.01 mmol) 70%).

GC-Mass (calculated: 679.24 g / mol, measured: 679 g / mol)

[Synthesis Example 37] Synthesis of compound Inv-529

Except that the compound IC-18 (3 g, 6.67 mmol) synthesized in Preparation Example 9 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4 and 2.58 g of 4'-bromobiphenyl-3-carbonitrile , 10.01 mmol) was used instead of 2- (4-bromophenyl) -1-phenyl-2,7a-dihydro-1H-benzo [d] imidazole (3.52 g, 10.01 mmol) The same procedure was followed to obtain compound Inv-529 (2.64 g, yield 55%).

GC-Mass (calculated: 719.27 g / mol, measured: 719 g / mol)

[Synthesis Example 38] Synthesis of compound Inv-563

Except that the compound IC-19 (3 g, 6.67 mmol) synthesized in Preparation Example 10 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4 and 2.58 g of 4'-bromobiphenyl-3-carbonitrile , Inv-563 (1.97 g, yield 49%) was obtained by following the same procedure as in Synthesis Example 4, except that 6-bromo-2,3'-bipyridine (2.35 g, 10.01 mmol) %).

GC-Mass (theory: 603.21 g / mol, measured: 603 g / mol)

[Synthesis Example 39] Synthesis of compound Inv-575

Except that the compound IC-19 (3 g, 6.67 mmol) synthesized in Preparation Example 10 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4 and 2.58 g of 4'-bromobiphenyl-3-carbonitrile , Inv-575 (2.31 g, yield 45%) was obtained by following the same procedure as in Synthesis Example 4, except that 3-bromo-N, N-diphenylaniline (3.25 g, 10.01 mmol) ).

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

[Synthesis Example 40] Synthesis of Compound Inv-598

Except that the compound IC-20 (3 g, 6.67 mmol) synthesized in Preparation Example 10 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4 and 2.58 g of 4'-bromobiphenyl-3-carbonitrile , Inv-598 (1.71 g, yield 41%) was obtained by following the same procedure as in Synthesis Example 4, except that 4'-bromobiphenyl-4-carbonitrile (2.58 g, 10.01 mmol) .

GC-Mass (calculated: 626.21 g / mol, measured: 626 g / mol)

[Synthesis Example 41] Synthesis of compound Inv-604

2- (3-chlorophenyl) triphenylene (2.71 g, 6.67 mmol) was used instead of the compound IC-20 (3 g, 6.67 mmol) synthesized in Preparation Example 10 instead of the compound IC- , Inv-604 (3.40 g, yield 75%) was obtained by following the same procedure as in Synthesis Example 1, except that 4-chloro-2,6-diphenylpyrimidine (2.14 g, 8.01 mmol) ).

GC-Mass (calculated: 679.24 g / mol, measured: 679 g / mol)

[Synthesis Example 42] Synthesis of compound Inv-615

Except that the compound IC-21 (3 g, 6.44 mmol) synthesized in Preparation Example 11 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4, and 2.58 g of 4'-bromobiphenyl- , Inv-615 (1.73 g, 9.67 mmol) was obtained by following the same procedure as in Synthesis Example 4, except that 4-bromo-6-phenyldibenzo [b, d] thiophene , Yield: 37%).

GC-Mass (calculated: 723.18 g / mol, measured: 723 g / mol)

[Synthesis Example 43] Synthesis of compound Inv-633

Compound IC-21 (3 g, 6.44 mmol) synthesized in Preparation Example 11 under nitrogen was dissolved in DMF (100 ml), NaH (0.39 g, 16.11 mmol) was added thereto, and the mixture was stirred for 1 hour. 2-chloro-4,6-diphenyl-1,3,5-triazine (3.45 g, 12.89 mmol) dissolved in DMF (100 ml) was slowly added thereto. After stirring for 3 hours, the reaction was terminated, and the mixture was filtered with silica, washed with water and methanol, and then the solvent was removed. The solvent-removed solid product was purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to give compound Inv-633 (1.84 g, yield 41%).

GC-Mass (calculated: 696.82 g / mol, measured: 696 g / mol)

[Synthesis Example 44] Synthesis of compound Inv-646

Except that the compound IC-22 (3 g, 6.44 mmol) synthesized in Preparation Example 11 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4, and 2.58 g of 4'-bromobiphenyl- The same procedure as in Synthesis Example 4 was carried out except that 4- (3-bromophenyl) -6-phenyldibenzo [b, d] thiophene (4.01 g, 9.67 mmol) 646 (2.68 g, yield 52%).

GC-Mass (calculated: 799.21 g / mol, measured: 799 g / mol)

[Synthesis Example 45] Synthesis of compound Inv-660

(3-chlorophenyl) triphenylene (2.71 g, 6.44 mmol) was used instead of the compound IC-22 (3 g, 6.44 mmol) synthesized in Preparation Example 11, , Inv-660 (2.87 g, yield: 97%) was obtained by following the same procedure as in Synthesis Example 1, except for using 2- (4-chlorophenyl) -4-phenylpyrimidine (2.06 g, 7.73 mmol) 64%).

GC-Mass (calculated: 695.21 g / mol, measured: 695 g / mol)

[Synthesis Example 46] Synthesis of Compound Inv-681

Instead of the compound IC-23 (3 g, 6.44 mmol) synthesized in Preparation Example 12 instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 1, 2- (3-chlorophenyl) triphenylene , Inv-681 (2.52 g, yield 66%) was obtained by following the same procedure as in Synthesis Example 1, except that 2-chloroquinazoline (1.27 g, 7.73 mmol)

GC-Mass (calculated: 593.17 g / mol, measured: 593 g / mol)

[Synthesis Example 47] Synthesis of compound Inv-691

Except that the compound IC-23 (3 g, 6.44 mmol) synthesized in Preparation Example 12 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4 and 2.58 g of 4'-bromobiphenyl-3-carbonitrile , Inv-691 (2.46 g, yield 55%) was obtained by following the same procedure as in Synthesis Example 4, except that 4-bromo-2,6-diphenylpyridine (3.00 g, 10.01 mmol) ).

GC-Mass (calculated: 694.22 g / mol, measured: 694 g / mol)

[Synthesis Example 48] Synthesis of Compound Inv-713

Except that the compound IC-24 (3 g, 6.44 mmol) synthesized in Preparation Example 12 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4, and 2.58 g of 4'-bromobiphenyl- , Inv-713 (1.96 g, yield 49%) was obtained by following the same procedure as in Synthesis Example 4, except that 6-bromo-2,3'-bipyridine (2.27 g, 9.67 mmol) %).

GC-Mass (calculated: 619.18 g / mol, measured: 619 g / mol)

[Synthesis Example 49] Synthesis of Compound Inv-728

(3 g, 6.44 mmol) synthesized in Preparation Example 12 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 1 and 2- (3-chlorophenyl) triphenylene , 8.01 mmol) instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (2.66 g, 7.73 mmol) To obtain a compound Inv-728 (3.74 g, yield 75%).

GC-Mass (calculated: 772.24 g / mol, measured: 772 g / mol)

[Synthesis Example 50] Synthesis of compound Inv-742

Except that the compound IC-10 (3 g, 6.67 mmol) synthesized in Preparation Example 5 was used instead of the compound IC-1 (3 g, 6.67 mmol) used in Synthesis Example 4 and 2.58 g of 4'-bromobiphenyl-3-carbonitrile Inv-742 (2.17 g, yield 52%) was obtained by following the same procedure as in Synthesis Example 4, except that 3'-bromobiphenyl-4-carbonitrile (2.58 g, 10.01 mmol) .

GC-Mass (calculated: 626.21 g / mol, measured: 626 g / mol)

[Example 1] Production of green organic EL device

Compound Inv-3 synthesized in Synthesis Example 1 was 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, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum evaporator.

M-MTDATA (60 nm) / TCTA (80 nm) / Inv-3 + 10% Ir (ppy) ₃ (30 nm) / BCP (10 nm) / Alq ₃ nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic EL device.

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

[Example 2] - [Example 50] Production of green organic EL device

Inv-11 to Inv-742 synthesized in Synthesis Examples 2 to 50, respectively, were used instead of the compound Inv-3 used as a luminescent host material in the formation of the light emitting layer in Example 1, Thereby preparing a green organic EL device.

[Comparative Example 1] Fabrication of organic EL device

An organic EL device was fabricated in the same manner as in Example 1, except that CBP was used instead of the compound Inv-3 of Synthesis Example 1 used as a light emitting host material in the formation of the light emitting layer in Example 1. The structure of CBP used is as follows.

[Evaluation Example 1]

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

Sample Host The driving voltage (V) EL peak (nm) Current efficiency (cd / A) Example 1 Inv-3 6.71 516 40.2 Example 2 Inv-11 6.79 517 39.8 Example 3 Inv-23 6.75 515 41.5 Example 4 Inv-28 6.71 516 38.4 Example 5 Inv-39 6.76 516 41.1 Example 6 Inv-54 6.81 517 40.7 Example 7 Inv-66 6.76 516 40.5 Example 8 Inv-79 6.79 516 39.7 Example 9 Inv-81 6.83 517 39.1 Example 10 Inv-113 6.75 516 41.1 Example 11 Inv-125 6.76 516 41.1 Example 12 Inv-145 6.81 517 40.7 Example 13 Inv-152 6.81 517 39.2 Example 14 Inv-173 6.83 518 38.8 Example 15 Inv-179 6.83 517 39.1 Example 16 Inv-211 6.85 516 38.4 Example 17 Inv-219 6.77 515 40.1 Example 18 Inv-230 6.79 516 39.7 Example 19 Inv-236 6.83 517 39.1 Example 20 Inv-274 6.75 516 41.1 Example 21 Inv-280 6.76 516 41.1 Example 22 Inv-287 6.81 517 39.2 Example 23 Inv-288 6.83 518 38.8 Example 24 Inv-322 6.83 517 39.1 Example 25 Inv-338 6.71 516 40.2 Example 26 Inv-353 6.76 516 41.1 Example 27 Inv-364 6.81 517 40.7 Example 28 Inv-388 6.76 516 40.5 Example 29 Inv-397 6.79 516 39.7 Example 30 Inv-413 6.83 517 39.1 Example 31 Inv-430 6.79 517 39.8 Example 32 Inv-440 6.75 515 41.5 Example 33 Inv-452 6.71 516 38.4 Example 34 Inv-462 6.72 517 41.2 Example 35 Inv-487 6.88 519 38.5 Example 36 Inv-510 6.88 516 39.2 Example 37 Inv-529 6.79 516 39.7 Example 38 Inv-563 6.83 517 39.1 Example 39 Inv-575 6.81 517 39.2 Example 40 Inv-598 6.83 518 38.8 Example 41 Inv-604 6.83 517 39.1 Example 42 Inv-615 6.81 517 40.7 Example 43 Inv-633 6.76 516 40.5 Example 44 Inv-646 6.79 516 39.7 Example 45 Inv-660 6.83 517 39.1 Example 46 Inv-681 6.81 517 39.2 Example 47 Inv-691 6.83 518 38.8 Example 48 Inv-713 6.83 517 39.1 Example 49 Inv-728 6.81 517 39.2 Example 50 Inv-742 6.83 518 38.8 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, in the case of the green organic EL devices of Examples 1 to 50 using the compound according to the present invention as a light emitting layer, in comparison with the green organic EL device of Comparative Example 1 using conventional CBP, Which shows excellent performance.

Claims (10)

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

In Formula 1,
Wherein _one of Y ₁ and Y ₂ , Y ₂ and Y ₃ , and one of Y ₃ and Y ₄ is C (R ₁ ), and each C (R ₁ ) is a condensation product of R ₁ and R ₁ , Forming a ring,
Y ₁ to Y ₄ are independently N or C (R ₁ ), and the remainder not forming the condensed ring of the formula (2)
When plural R &lt; ₁ &gt; s are the same or different from each other;
(2)

In Formula 2,
The dotted line means a site condensed in the formula (1)
Wherein one of Y ₅ and Y ₆ , Y ₆ and Y _7, and Y ₇ and Y ₈ is both C (R ₂ ), and each of C (R ₂ ) and R ₂ is condensed with each other to form a condensed ring Lt; / RTI &gt;
To from Y ₅ to Y ₈ rest does not form a condensed ring of the general formula (3) are each independently N or C (R _2),
When R ₂ is plural, they are the same or different from each other;
(3)

In Formula 3,
The dotted line means a site condensed in the formula (2)
Y ₉ to Y ₁₂ are each independently N or C (R ₃ ), and when R ₃ is plural, they are the same or different from each other;
X _1, X ₄ and X ₅ is selected from the group consisting of each independently O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and _{Si (Ar 4) (Ar 5} ), Wherein at least one of X ₁ , X ₄ and X ₅ is N (Ar ₁ );
X ₂ and X ₃ are each independently N or C (R ₄ ), wherein when R ₄ is plural, they are the same or different from each other;
R ₁ to R ₄ and Ar ₁ to Ar ₅ are the same or different and each independently represents hydrogen, deuterium (D), halogen, cyano group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkene A C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group , A C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group , C ₆ ~ C ₄₀ aryl boron group, C ₁ ~ C ₄₀ phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~ is selected from the group consisting of C ₄₀ of arylsilyl of,
R ₁ to R ₄ and Ar ₁ to Ar ₅ of C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₄₀ aryl group, nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ of the phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl groups are each independently a heavy hydrogen (D), a halogen, a cyano group, an alkenyl group of C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C ₆ ~ C _40, alkyloxy group of C ₁ ~ C ₄₀ of, C ₆ ~ C ₄₀ of the arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a 3 to 40 nuclear atoms of a heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl yarn Group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl And when the substituent is plural, they may be the same or different from each other. The method according to claim 1,
Wherein said compound is represented by any one of the following formulas (4) to (9):
[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

In the above formulas 4 to 9,
X ₁ to X ₄ , And Y ₁ to Y ₈ are as defined in claim 1, respectively. The method according to claim 1,
Wherein the compound of Formula 1 is represented by any one of the following Formulas C-1 to C-36:

In the above formulas C-1 to C-36,
X ₁ to X ₅ , and Y ₁ to Y ₁₂ are as defined in claim 1, respectively. The method according to claim 1,
Wherein the compound of formula (1) is represented by any one of the following formulas (10) to (15):
[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

In the above formulas 10 to 15,
X ₂ and X ₃ , Y ₁ to Y ₄ , and Ar ₁ to Ar ₅ are as defined in claim 1, respectively. The method according to claim 1,
Wherein the compound of Formula 1 is represented by any one of the following Formulas A-1 to A-24:

In the above Formulas A-1 to A-24,
R ₄ , Y ₁ to Y _4, and Ar ₁ to Ar ₅ are as defined in claim 1, respectively. The method according to claim 1,
X ₄ and X ₅ are both N (Ar ₁ )
Wherein Ar &_lt; 1 &gt; is as defined in claim ₁ . The method according to claim 1,
Y ₁ to Y ₄ are both C (R ₁ )
Y ₅ to Y ₈ are both C (R ₂ )
Y ₉ to Y ₁₂ are all C (R ₃ )
Wherein R &_lt; ₁ &gt; to R &_lt; ₃ &_gt; are each as defined in claim 1. The method according to claim 1,
R ₁ to R ₄ and Ar ₁ to Ar ₅ are the same or different, each independently represent hydrogen, deuterium (D), C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, and C ₆ of the - the compound is characterized by being selected from the group consisting of C ₄₀ arylamines. 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 1 to 8. 10. The method of claim 9,
Wherein at least one of the one or more organic layers including the compound is a light emitting layer.