KR101599597B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic compound and an organic electroluminescent device including the organic compound. Since the organic compound of the present invention is used in an organic compound layer of an organic electroluminescent device, preferably a light emitting layer, And the like 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 and an organic electroluminescent device including the same.

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

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

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

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

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

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

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

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

[Chemical Formula 1]

In Formula 1,

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,

And the remainder not forming the condensed ring of the formula (2) among Y ₁ to Y ₄ are each independently N or C (R ₁ ), wherein when R ₁ is plural, a plurality of R _{1 s} are the same as or different from each other,

(2)

In Formula 2,

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 >

And Y ₅ to the remaining non-condensed to form a ring are each independently N or C (R ₂₎ of the following formula (3) in a Y _8, wherein if R ₂ is a plurality, the plurality of R ₂ are the same or different from each other,

(3)

Y ₉ to Y ₁₂ are each independently N or C (R ₃ ), and when R ₃ is plural, a plurality of R _{3 s} may be the same or different,

In the above Formulas 1 to 3,

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 ₄ and X ₅ is C (Ar ₂ ) (Ar ₃ )

X ₂ and X ₃ are each independently N or C (R ₄ ), wherein when R ₄ is plural, a plurality of R _{4 s} are the same as or different from each other,

R ₁ to R ₄ and Ar ₁ to Ar ₅ are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, amino, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alk A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, an aryl boronic of C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ Group, a phosphine group of C ₁ to C ₄₀ , a phosphine oxide group of C ₁ to C ₄₀ , and an arylsilyl group of C ₆ to C ₄₀ , or may be bonded to adjacent groups to form a condensed ring,

R ₁ to R ₄ and Ar ₁ to Ar ₅ group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, alkyl silyl group, A halogen atom, a cyano group, an amino group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ ~ aryloxy C ₄₀ of, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ arylamine group of C _40, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ arylboronic group of C _40, C ₁ ~ C ₄₀ value of a phosphine group, C ₁ ~ C ₄₀ the phosphine oxide groups and one or more substituents selected from the group consisting of aryl silyl C ₆ ~ C ₄₀ of Or it may be unsubstituted. Here, when R ₁ to R ₄ and Ar ₁ to Ar ₅ are substituted with a plurality of substituents, the plurality of substituents may be the same or different from each other.

According to another aspect of the present invention, there is provided an organic electroluminescent device including a positive electrode, a negative electrode, and at least one organic material layer interposed between the positive electrode and the negative electrode, Lt; / RTI >

The compound represented by the general formula (1) of the present invention has excellent thermal stability and phosphorescence characteristics 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.

1. Organic compounds

The organic compound of the present invention is a structure in which three inden moieties containing one or more hetero atoms such as N, O, S, etc. are sequentially condensed to form a basic skeleton, and various substituents are bonded to the basic skeleton. 1.

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

In addition, the compound of the present invention having high triplet energy can prevent the excitons generated in the light emitting layer from diffusing into the adjacent electron transporting layer or hole transporting layer, thereby improving the luminous efficiency by increasing the number of excitons contributing to light emission.

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

Meanwhile, the compound of the present invention has various substituents, especially aryl groups and / or heteroaryl groups, introduced into the basic skeleton, and the molecular weight of the compound is significantly increased. As a result, the glass transition temperature is improved and a conventional organic layer material (for example, CBP ) ≪ / RTI > Further, the compound is also effective in inhibiting crystallization of the organic material layer.

Therefore, when the compound of the present invention is applied to an organic compound layer (specifically, a hole injection layer, a hole transport layer, a light emitting layer, a light emitting auxiliary layer, or the like) of an organic electroluminescent device, performance and lifetime characteristics of the organic electroluminescent device can be greatly improved. Further, the lifetime of the organic electroluminescent device can be maximized by maximizing the performance of the full-color organic electroluminescent panel.

Such compounds of the present invention may be embodied in any one of the compounds represented by the following general formulas (10) to (15).

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

In Formulas 10 to 15, X ₂ and X ₃ , Y ₁ to Y _4, and Ar ₁ to Ar ₅ are as defined above.

The compounds represented by the general formulas (10) to (15) can be further formulated into the compounds represented by the following general formulas (A-1) to (A-24) in consideration of the physical and chemical properties of the compounds.

In Formulas A-1 to A-24, Y ₁ to Y ₄ , Ar ₁ to Ar ₅ and R ₂ are as defined above.

Such a compound of the present invention may be any one of the compounds represented by the following formulas (4) to (9).

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

In Formulas 4 to 9, X ₁ to X ₄ and Y ₁ to Y ₈ are as defined above.

The compound of the present invention is preferably any one of the compounds represented by 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 above.

In the compound of the present invention, when X ₄ is C (Ar ₂ ) (Ar ₃ ), X ₅ is N (Ar ₁ ), X ₅ is C (Ar ₂ ) (Ar ₃ ), X ₄ is preferably N (Ar ₁ ). In the compound of the present invention, it is preferable that all of Y ₁ to Y ₄ are C (R ₁ ), all of Y ₅ to Y ₈ are C (R ₂ ), and all of Y ₉ to Y ₁₂ are C (R ₃ ) Do.

In R ₁ to R ₄ and Ar ₁ to Ar ₅ are each independently consisting of hydrogen, deuterium, an arylamine of C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, and a C ₆ ~ C ₄₀ of Lt; / RTI > Specifically, R ₁ to R ₄ and Ar ₁ to Ar ₅ may each independently be selected from the group consisting of hydrogen, deuterium, or substituents represented by the following S1 to S211.

Also, R ₁ to R ₄ and Ar ₁ to Ar ₅ may each independently be selected from the group consisting of substituents represented by the following formulas (D-1) to (D-15).

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

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

R ₁₁ and R ₂₁ are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, amino, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ arylboron groups, C ₁ ~ C ₆₀ 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, the combined adjacent groups may form a condensed ring, n is from 0 to Lt; / RTI >

Wherein a plurality of R < ₁₁ > are the same as or different from each other, and a plurality of R < ₂₁ >

Specific examples of the compounds of the present invention described above include the following compounds Inv-1 to Inv-745, but the compounds of the present invention are not limited thereto.

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 60 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. Also, two or more rings 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 6 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. ≪ / RTI > 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 6 to 60 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.

2. Organic electroluminescent device

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

Specifically, the organic electroluminescent device of the present invention includes an anode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, ≪ / RTI > At this time, the compounds may be used alone or in combination of two or more.

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

Specifically, the organic electroluminescent device of the present invention may include a light emitting layer including a host, wherein the compound includes the compound as the host. As described above, when the compound is incorporated into a light emitting layer material of an organic electroluminescent device, preferably a phosphorescent host material of blue, green, and red, bonding power between holes and electrons in the light emitting layer increases, Efficiency and power efficiency), lifetime, luminance and driving voltage, etc., can be improved.

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

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

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 used in the fabrication of the organic electroluminescent device of the present invention is not particularly limited, but silicon wafer, quartz, glass plate, metal plate, plastic film and the like can be used.

The anode material is also not particularly limited, but may be a metal such as vanadium, chromium, copper, zinc, or gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black may be used.

The negative electrode material is not particularly limited, and 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.

Materials contained in the hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer are not particularly limited as long as they are known in the art.

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 IC-1

<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 under a nitrogen stream. After two hours completion of the reaction, extracted with dichloromethane, and then remove the water with MgSO ₄ and purified by column chromatography (Hexane: EA = 4: 1 (v / v)) N- (2,4- to give 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) were mixed under a nitrogen stream and stirred at 140 ° C for 1.5 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO _4, and the residue was purified by column chromatography (Hexane: EA = 9: 1 (v / v)) to obtain 6-bromo-2-phenylbenzo [ 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

(161.48 g, 0.589 mol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi Dioxaborolane (179.52 g, 0.707 mol), Pd (dppf) Cl ₂ (24.05 g, 29.46 mmol), KOAc (173.44 g, 1.77 mol) and 1,4- And the mixture was stirred at 130 DEG C for 12 hours. After the reaction was completed, the reaction mixture 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)) to obtain 2-phenyl- , 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

2-yl) benzo [d] oxazole (149.48 g, 0.465 mol), 4-bromo-2 (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- -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 DEG C for 12 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. 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

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

(113.7 g, 0.29 mol), triphenylphosphine (188.65 g, 0.72 mol) and 1,2-dichlorobenzene (1500 ml) were charged in a nitrogen stream under nitrogen atmosphere. Followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, and the mixture 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 7-bromo-2-phenyl-10H-oxazolo [ Yield: 45%).

^{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 , &Lt; / RTI &gt; 1H), 10.2 (s, 1H)

<Step 6> Synthesis of 7- (2-isopropylphenyl) -2-phenyl-10H-oxazolo [5,4-a]

In a nitrogen atmosphere 7-bromo-2-phenyl- 10H-oxazolo [5,4-a] carbazole (47 g, 0.129 mol), 2-isopropylphenylboronic acid (25.47 g, 0.155 mol), Pd (PPh 3) 4 (8.97 g, 7.76 mmol), K ₂ CO ₃ (64.38 g, 0.466 mol) and THF / H ₂ O (300 ml / 150 ml) were mixed and stirred at 80 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane: EA = 5: 1 (v / v)) to obtain 7- (2-isopropylphenyl) -2-phenyl-10H-oxazolo [ (30.21 g, yield 58%).

^{1 H-NMR: δ 1.21 (} s, 6H), 2.88 (s, 1H), 7.23 (d, 1H), 7.33 (d, 2H), 7.36 (d, 1H), 7.41 (t, 1H), 7.51 ( (d, 2H), 7.69 (d, 1H), 7.71 (d, 1H), 7.77 , 1H)

<Step 7> Synthesis of IC-1

7- (2-isopropylphenyl) -2- phenyl-10H-oxazolo under nitrogen gas stream, [5,4-a] carbazole (30 g, 74.54 mmol) and _{RhCl (PPh 3) 3 (0.34} g, 0.5 mol%) of 1 , 4-dioxane (300 ml), and the mixture was stirred at 135 ° C for 3 hours. After completion of the reaction, the solvent was removed and the residue was purified by column chromatography (Hexane: EA = 5: 1 (v: v)) to obtain IC-1 (12.84 g, yield 43%).

^{1 H NMR: δ 1.72 (s} , 6H), 7.24 (d, 2H), 7.33 (s, 1H), 7.41 (t, 1H), 7.44 (d, 1H), 7.50 (d, 2H), 7.61 (d , 8.09 (d, IH), 8.12 (d, IH), 10.49 (s, IH)

[Preparation Example 2] Synthesis of IC-4

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

Bromo-2-phenyl-5H-oxazolo [4,5-b] carbazole (44.93 g, yield 43%) was obtained by following the procedure of <Step 5> of Preparation Example 1 above.

¹ H-NMR:? 7.41 (m, 3H), 7.51 (d, 3H), 7.57 (s,

<Step 2> Synthesis of 8- (2-isopropylphenyl) -2-phenyl-5H-oxazolo [4,5-b] carbazole

Bromo-2-phenyl-5H-oxazolo [4,5-b] carbazole (40 g, 0.11 mol) was used instead of 7-bromo-2-phenyl-10H-oxazolo [5,4- 2-isopropylphenyl) -2-phenyl-5H-oxazolo [4,4-d] pyrimidine was obtained by following the procedure of Step 6 of Preparation Example 1, 5-b] carbazole (26.6 g, yield 60%).

^{1 H-NMR: δ 1.19 (} s, 6H), 2.88 (s, 1H), 7.33 (d, 2H), 7.36 (d, 1H), 7.41 (m, 2H), 7.50 (d, 2H), 7.54 ( 1H), 7.70 (d, 2H), 7.86 (d, 1H), 8.05 (d, 2H), 10.52

<Step 3> Synthesis of IC-4

2-isopropylphenyl) -2-phenyl-5H-oxazolo [4,5-b] carbazole (prepared from 25 g , 62.11 mmol), and the procedure of Step 7 of Preparation Example 1 was followed except that RhCl (PPh ₃ ) ₃ (0.29 g, 0.5 mol%) was used to obtain 9.95 g , Yield: 40%).

^{1 H-NMR: δ 1.73 (} s, 6H), 7.24 (d, 1H), 7.33 (s, 1H), 7.40 (s, 1H), 7.42 (m, 2H), 7.50 (d, 2H), 7.55 ( 1H), 7.60 (d, 1H), 7.68 (s, 1H), 8.08

[Preparation Example 3] Synthesis of IC-7

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

Except that 2,5-dibromoaniline (250 g, 1.0 mol) was used in place of 2,4-dibromoaniline to obtain N- (2,5-dibromophenyl) benzamide (251.14 g, yield 71%).

^{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

Step 2 of Preparation Example 1 was repeated except that N- (2,5-dibromophenyl) benzamide (251.14 g, 0.71 mol) was used in place of N- (2,4-dibromophenyl) 5-bromo-2-phenylbenzo [d] oxazole (155.12 g, yield 80%).

^{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

Step 3 of Preparation Example 1 was repeated except that 5-bromo-2-phenylbenzo [d] oxazole (155.12 g, 0.566 mol) was used instead of 6-bromo-2- phenylbenzo [ To obtain 2-phenyl-5- (4,4,5,5-tetramethyl-1,3,2-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

2-phenyl-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [ Step 4 of Preparation Example 1 was carried out except that tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole (136.32 g, 0.434 mol) (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (108.27 g, 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 7-bromo-2-phenyl-10H-oxazolo [4,5-a] carbazole

(108.27 g, 0.273 mol) instead of 5- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole 10-oxazolo [4,5-a] carbazole (41.79 g, yield 42%) was obtained by following the procedure of <Step 5> of Preparation Example 1,

¹ H-NMR:? 7.00 (d, 1 H), 7.42 (m, 2H), 7.52 (d, 3H), 8.05

<Step 6> Synthesis of 7- (2-isopropylphenyl) -2-phenyl-10H-oxazolo [4,5-a]

10-oxazolo [4,5-a] carbazole (40 g, 0.11 mol) instead of 7-bromo-2-phenyl-10H-oxazolo [5,4- 2-isopropylphenylboronic acid (21.67 g, 0.132 mol) was used instead of 4- (2-isopropylphenyl) -2-phenyl-10H-oxazolo [4 , 5-a] carbazole (24.38 g, yield 55%).

^{1 H-NMR: δ 1.22 (} s, 6H), 2.86 (s, 1H), 7.33 (d, 2H), 7.36 (d, 1H), 7.41 (t, 1H), 7.51 (d, 2H), 7.68 ( (d, IH), 7.00 (d, 2H), 7.77 (s, IH), 7.87

<Step 7> Synthesis of IC-7

10H-oxazolo [4,5-a] carbazole (prepared according to the procedure described for the synthesis of 7- (2-isopropylphenyl) -2-phenyl-10H-oxazolo [5,4- , IC-7 (10.2 g, yield) was obtained in the same manner as in <Step 7> of Preparation Example 1 except that RhCl (PPh ₃ ) ₃ (0.29 g, 0.5 mol% 41%).

^{1 H-NMR: δ 1.70 (} s, 6H), 7.00 (d, 1H), 7.24 (d, 1H), 7.41 (t, 1H), 7.44 (d, 1H), 7.51 (d, 3H), 7.61 ( (d, IH), 7.79 (d, IH), 8.05 (d, 2H), 8.09

[Preparation Example 4] Synthesis of IC-13

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

Except that 4-bromo-1-iodo-2-nitrobenzene (138.73 g, 0.423 mol) was used in place of 4-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 7-bromo-2-phenyl-5H-oxazolo [4,5-b] carbazole

(110.36 g, 0.279 mol) instead of 6- (4-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole 5-oxazolo [4,5-b] carbazole (43.61 g, yield 43%) was obtained by following the procedure of <Step 5> of Preparation Example 1,

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

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

(40 g, 0.11 mol) was used instead of 7-bromo-2-phenyl-10H-oxazolo [5,4- 2-isopropylphenylboronic acid (21.67 g, 0.132 mol) was used in place of 4- (2-isopropylphenyl) -2-phenyl-5H-oxazolo [ 5-b] carbazole (25.27 g, yield 57%).

¹ H-NMR:? 1.20 (s, 6H), 2.88 (s, 1H), 7.33 (d, 2H), 7.36 (d, 2H), 7.54 (s, IH), 7.62 (s, IH), 7.71 (d, IH), 7.79 , 1H)

<Step 4> Synthesis of IC-13

Phenyl-5H-oxazolo [4,5-b] carbazole (prepared according to the procedure described for the synthesis of 7- (2-isopropylphenyl) -2-phenyl-10H-oxazolo [5,4- , IC-13 (9.45 g, 0.5 mmol) was obtained by carrying out the same procedure as <Step 7> of Preparation Example 1 except that RhCl (PPh ₃ ) ₃ (0.29 g, 0.5 mol% Yield: 38%).

^{1 H-NMR: δ 1.72 (} s, 6H), 7.24 (d, 1H), 7.40 (m, 2H), 7.44 (d, 1H), 7.51 (d, 2H), 7.54 (s, 2H), 7.61 ( 1H), 8.05 (d, 2H), 8.09 (d, 1H), 8.12

[Preparation Example 5] Synthesis of IC-15

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

2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] oxazole and 4-bromo-2-iodo- (120 g, 0.374 mol) and 4-bromo-1-iodo-2-nitrobenzene were added to a solution of 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- (4-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole (93.96 g, 0.340 mol) was used in the same manner as in <Step 4> of Preparation Example 1, 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

(93.96 g, 0.238 mol) was used instead of 5- (4-bromo-2-nitrophenyl) -2-phenylbenzo [d] oxazole Bromo-2-phenyl-5H-oxazolo [5,4-b] carbazole (44.04 g, yield 51%) was obtained in the same manner as in <Step 5> of Preparation Example 1,

^{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- (2-isopropylphenyl) -2-phenyl-5H-oxazolo [5,4-b]

(40 g, 0.11 mol) was used instead of 7-bromo-2-phenyl-10H-oxazolo [5,4- 2-isopropylphenylboronic acid (21.67 g, 0.132 mol) was used instead of 4- (2-isopropylphenyl) boronic acid 4-b] carbazole (27.04 g, yield 61%).

^{1 H-NMR: δ 1.20 (} s, 6H), 2.88 (s, 1H), 7.33 (d, 2H), 7.36 (d, 1H), 7.40 (m, 2H), 7.51 (d, 2H), 7.55 ( 2H), 8.18 (d, 1H), 10.50 (s, 1H), 7.62 (d,

<Step 4> Synthesis of IC-15

Phenyl-5H-oxazolo [5,4-b] carbazole (prepared according to the procedure described for the synthesis of 7- (2-isopropylphenyl) -2-phenyl-10H-oxazolo [5,4- , IC-15 (9.2 g, 0.5 mmol) was used in the same manner as in <Step 7> of Preparation Example 1 except that RhCl (PPh ₃ ) ₃ (0.29 g, 0.5 mol% Yield: 37%).

^{1 H-NMR: δ 1.70 (} s, 6H), 7.24 (d, 1H), 7.41 (m, 2H), 7.44 (d, 1H), 7.50 (d, 2H), 7.55 (s, 1H), 7.60 ( (d, IH), 7.71 (d, IH), 8.00 (d, IH), 8.05

[Preparation Example 6] Synthesis of IC-21

<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. Then, Lawesson ' s reagent (172.14 g, 0.39 mol) was added dropwise and stirred at 110 DEG C for 4 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride, then the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 7: 1 (v / v)) to obtain 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

Step 2 of Preparation Example 1 was repeated except that N- (2,4-dibromophenyl) benzothioamide (192.32 g, 518.26 mmol) was used in place of N- (2,4-dibromophenyl) 6-bromo-2-phenylbenzo [d] thiazole (106.78 g, yield 71%).

^{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

Step 3 of Preparation Example 1 was repeated except that 6-bromo-2-phenylbenzo [d] thiazole (106.78 g, 0.367.98 mol) was used instead of 6-bromo-2- phenylbenzo [ 2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] thiazole (93.07 g, yield 75%) was obtained.

^{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

2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [ Step 4 of Preparation Example 1 was carried out except that tetramethyl-1,3,2-dioxaborolan-2-yl) benzo [d] thiazole (93.07 g, 0.276 mol) (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] thiazole (65 g, 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]

(65 g, 0.158 mol) instead of 6- (5-bromo-2-nitrophenyl) -2-phenylbenzo [d] 10-thiazolo [5,4-a] carbazole (25.18 g, yield 42%) was obtained by following the procedure of <Step 5> of Preparation Example 1,

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

<Step 6> Synthesis of 7- (2-isopropylphenyl) -2-phenyl-10H-thiazolo [5,4-a]

10-thiazolo [5,4-a] carbazole (25 g, 65.92 mmol) was used instead of 7-bromo-2-phenyl-10H-oxazolo [5,4- 2-isopropylphenylboronic acid (12.97 g, 79.02 mmol) was used in place of 4- (2-isopropylphenyl) -2-phenyl-10H-thiazolo [5 , 4-a] carbazole (16.28 g, yield 59%).

^{1 H-NMR: δ 1.20 (} s, 6H), 2.88 (s, 1H), 7.33 (d, 2H), 7.36 (d, 1H), 7.40 (t, 1H), 7.50 (d, 2H), 7.55 ( (d, IH), 7.70 (d, 2H), 7.75 (d, IH), 7.77

<Step 7> Synthesis of IC-21

10-thiazolo [5,4-a] -carbazole (prepared in Example 1) in place of 7- (2-isopropylphenyl) -2-phenyl-10H-oxazolo [5,4- , 5.35 g, 35.84 mmol) was used in the same manner as in <Step 7> of Preparation Example 1 except that RhCl (PPh ₃ ) ₃ (0.29 g, 0.5 mol% , Yield: 39%).

^{1 H-NMR: δ 1.71 (} s, 6H), 7.24 (d, 1H), 7.33 (s, 1H), 7.40 (t, 1H), 7.43 (d, 1H), 7.51 (d, 2H), 7.55 ( 1H), 7.61 (d, IH), 7.69 (s, IH), 7.75 (d, IH), 8.02

[Preparation Example 7] Synthesis of IC-23

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

Bromo-2-phenyl-5H-thiazolo [4,5-b] carbazole (20.75 g, yield 45%) was obtained by following the procedure of <Step 5> of Preparation Example 6 above.

^{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- (2-isopropylphenyl) -2-phenyl-5H-thiazolo [4,5-b]

Bromo-2-phenyl-5H-thiazolo [4,5-b] carbazole (20 g, 52.73 mmol) was used instead of 7-bromo-2-phenyl-10H- thiazolo [5,4- 2-isopropylphenylboronic acid (10.38 g, 63.28 mmol) was used in place of 8- (2-isopropylphenyl) -2-phenyl-5H-thiazolo [4 , 5-b] carbazole (12.36 g, yield 56%).

^{1 H-NMR: δ 1.20 (} s, 6H), 2.87 (s, 1H), 7.33 (d, 2H), 7.36 (d, 1H), 7.41 (t, 1H), 7.50 (d, 2H), 7.69 ( (d, 2H), 7.77 (s, 1H), 7.88 (d, 1H), 8.03

<Step 3> Synthesis of IC-23

2-isopropylphenyl) -2-phenyl-5H-thiazolo [4,5-b] carbazole (prepared from 10 g , 23.89 mmol), IC-23 (3.48 g, yield 35%) was obtained in the same manner as in <Step 7> of Preparation Example 6 above.

^{1 H-NMR: δ 1.71 (} s, 6H), 7.24 (d, 1H), 7.33 (s, 1H), 7.40 (t, 1H), 7.42 (d, 1H), 7.49 (d, 2H), 7.60 ( 1H), 7.69 (s, 1H), 8.02 (d, 2H), 8.08 (d,

[Preparation Example 8] Synthesis of IC-31

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

2-phenyl-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzoate was used instead of 7-bromo-2- 2-iodo-1-isopropylbenzene (101.18 g, 0.311 mol) was used instead of 2-isopropylphenylboronic acid in the same manner as in Preparation Example 1, except that [d] oxazole (100 g, 0.311 mol) 5-bromo-2-isopropylphenyl) -2-phenylbenzo [d] oxazole (65.96 g, yield 54%) was obtained in the same manner as in <Step 6>.

¹ H-NMR:? 1.21 (s, 6H), 7.25 (d, IH), 7.38 (s, IH), 7.41 d, 2 H), 8.04 (d, 2H), 8.09 (s, 1 H)

<Step 2> Synthesis of 6-bromo-9,9-dimethyl-2-phenyl-9H-fluoreno [3,2-d] oxazole

(5-bromo-2-isopropylphenyl) -2-phenylbenzo [d] oxazole (65 g, 0.166 mol) in place of 7- (2-isopropylphenyl) -2-phenyl- use _{and, RhCl (PPh 3) 3 (} 0.77 g, 0.5 mol%) , except that the applying and performs the same procedure as in <step 7> the preparation example 1, 6-bromo-9,9-dimethyl- 2-phenyl-9H-fluoreno [3,2-d] oxazole (33.63 g, yield 52%).

^{1 H-NMR: δ 1.70 (} s, 6H), 7.40 (t, 1H), 7.42 (d, 1H), 7.45 (d, 1H), 7.54 (s, 1H), 7.84 (s, 1H), 7.50 ( d, 2H), 8.00 (s, 1 H), 8.05 (d, 2 H)

Step 3 Synthesis of 10,10-dimethyl-7- (2-nitrophenyl) -2-phenyl-10H-fluoreno [1,2-d] oxazole

9-dimethyl-2-phenyl-9H-fluoreno [3,2-d] oxazole (30 g, 76.87 mmol) instead of 7-bromo-2-phenyl-10H- dimethyl-2-isopropylphenylboronic acid was used in place of 2-nitrophenylboronic acid (15.4 g, 92.24 mmol) instead of 2-isopropylphenylboronic acid. 7- (2-nitrophenyl) -2-phenyl-10H-fluoreno [1,2-d] oxazole (14.29 g, yield 43%).

^{1 H-NMR: δ 1.71 (} s, 6H), 7.41 (t, 1H), 7.50 (d, 2H), 7.53 (d, 1H), 7.61 (d, 1H), 7.67 (d, 1H), 7.87 ( (d, IH), 7.90 (d, IH), 8.00 (d, 2H), 8.04

<Step 4> Synthesis of IC-31

Substituting 10,10-dimethyl-7- (2-nitrophenyl) -2-phenyl-10H-fluoreno [1,2-d] oxazole for 6- (5-bromo- IC-31 (3.61 g, yield 39%) was obtained in the same manner as in <Step 5> of Preparation Example 1 except that 10 g of the compound obtained in Step 1 of Example 1 was used and Triphenylphosphine (15.16 g, 57.81 mmol) ).

^{1 H-NMR: δ 1.71 (} s, 6H), 7.28 (d, 1H), 7.41 (t, 1H), 7.43 (d, 2H), 7.50 (d, 3H), 7.62 (d, 1H), 8.00 ( (d, IH), 8.04 (d, 2H), 8.09 (d,

[Preparation Example 9] Synthesis of IC-41

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

Step 1 of Preparation Example 8 was repeated except that 4-bromo-1-iodo-2-isopropylbenzene (101.18 g, 0.311 mol) was used in place of 4-bromo-2-iodo-1- To obtain 5- (4-bromo-2-isopropylphenyl) -2-phenylbenzo [d] oxazole (62.29 g, yield 51%).

¹ H-NMR:? 1.20 (s, 6H), 2.87 (s, IH), 7.40 (t, IH), 7.48 (d, (d, IH), 7.85 (d, IH), 8.04 (d, 2H), 8.08

<Step 2> Synthesis of 8-bromo-10,10-dimethyl-2-phenyl-10H-fluoreno [1,2-d] oxazole

Bromo-2-isopropylphenyl) -2-phenylbenzo [d] oxazole (60 g, 0.153 mol) was used instead of 5- (5-bromo- _{RhCl (PPh 3) 3 (0.71} g, 0.5 mol%) , and by performing the same procedure as in <step 2> of the preparation example 8, except that the application of 8-bromo-10,10-dimethyl- 2-phenyl- 10H-fluoreno [1,2-d] oxazole (29.84 g, yield 50%).

^{1 H-NMR: δ 1.70 (} s, 6H), 7.38 (d, 1H), 7.40 (t, 1H), 7.50 (d, 2H), 7.55 (d, 1H), 7.71 (s, 1H), 7.76 ( d, 1 H), 7.87 (d, 1 H), 8.04 (d, 2 H)

<Step 3> Synthesis of 10,10-dimethyl-8- (2-nitrophenyl) -2-phenyl-10H-fluoreno [1,2- d] oxazole

Bromo-10,10-dimethyl-2-phenyl-10H-fluoreno (6-bromo-9,9-dimethyl-2-phenyl-9H- Step 3 of Preparation Example 8 was repeated except that 2-nitrophenylboronic acid (12.83 g, 76.87 mmol) was used instead of [1,2-d] oxazole (25 g, 64.06 mmol) To obtain 10,10-dimethyl-8- (2-nitrophenyl) -2-phenyl-10H-fluoreno [1,2-d] oxazole (11.36 g, yield 41%).

^{1 H-NMR: δ 1.70 (} s, 6H), 7.41 (t, 1H), 7.51 (d, 2H), 7.57 (d, 1H), 7.63 (d, 1H), 7.67 (d, 1H), 7.77 ( (d, IH), 7.90 (d, IH), 7.93

<Step 4> Synthesis of IC-41

10-dimethyl-8- (2-nitrophenyl) -2-phenyl-10H-fluorene [ (3.15 g, yield: 34%) was obtained by carrying out the same processes as in <Step 4> of Preparation Example 8, except that 5-fluoreno [1,2-d] oxazole (10 g, 23.12 mmol) .

^{1 H-NMR: δ 1.71 (} s, 6H), 7.29 (d, 1H), 7.40 (t, 1H), 7.44 (d, 1H), 7.50 (d, 3H), 7.54 (s, 1H), 7.63 ( 1H), 8.04 (d, 2H), 8.08 (d, 1H), 8.12 (s, 2H), 10.52

[Preparation Example 10] Synthesis of IC-42

The same procedure as in <Step 4> of Preparation Example 9 was conducted to obtain IC-42 (3.43 g, yield 37%).

^{1 H-NMR: δ 1.71 (} s, 6H), 7.28 (d, 1H), 7.40 (t, 1H), 7.43 (d, 1H), 7.49 (d, 3H), 7.63 (d, 1H), 7.72 ( (d, 2H), 8.08 (d, IH), 8.11 (d, IH), 10.48

[Synthesis Example 1] Inv-13 synthesis

(4.40 g, 18.73 mmol), Cu powder (0.08 g, 1.25 mmol), K ₂ CO ₃ (1.73 g, 1.25 mmol), IC-1 (5 g, 12.49 mmol), 6-bromo- 12.49 mmol), Na ₂ SO ₄ (1.77 g, 12.49 mmol) and nitrobenzene (100 ml) were mixed and stirred at 200 ° C for 24 hours. After completion of the reaction, 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 the residue was purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to give Inv-13 (3.67 g, yield 53%) as a target compound.

GC-Mass (calculated: 554.21 g / mol, measured: 554 g / mol)

[Synthesis Example 2] Inv-24 synthesis

(5 g, 12.49 mmol), 4-chloro-2,6-diphenylpyrimidine (4.00 g, 14.98 mmol), Pd (OAc) ₂ (0.14 g, 5 mol%), NaO ) (3.60 g, 37.46 mmol), P (t-bu) ₃ (0.25 g, 1.25 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C for 12 hours. Extracted with ethyl acetate. After the reaction was terminated, and then remove the water with MgSO ₄ and purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to give the Inv-24 (5.67 g, yield 72 The desired compound as a %).

GC-Mass (theory: 630.24 g / mol, measured: 630 g / mol)

[Synthesis Example 3] Inv-26 synthesis

The procedure of Synthesis Example 2 was repeated except that 4- (4-chlorophenyl) -2,6-diphenylpyrimidine (5.14 g, 14.98 mmol) was used in place of 4-chloro-2,6-diphenylpyrimidine. Inv-26 (6 g, yield 68%).

GC-Mass (calculated: 706.27 g / mol, measured: 706 g / mol)

[Synthesis Example 4] Inv-27 synthesis

Except that 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (5.15 g, 14.98 mmol) was used in place of 4-chloro-2,6-diphenylpyrimidine. The same procedure was followed to obtain the target compound Inv-27 (6.1 g, yield 69%).

GC-Mass (707.27 g / mol, measured: 707 g / mol)

[Synthesis Example 5] Inv-86 synthesis

IC-4 (5 g, 12.49 mmol) was dissolved in DMF (100 ml) under nitrogen, NaH (0.75 g, 31.21 mmol) was added thereto, and the mixture was stirred for 1 hour. Then, 2-chloro-4,6-diphenyl-1,3,5-triazine (6.68 g, 24.97 mmol) dissolved in 100 ml of DMF was slowly added. After stirring for 3 hours, the reaction was terminated and the mixture was filtered through silica, washed with water and methanol, and then the solvent was removed. The solvent-removed solid was purified by column chromatography (Hexane: EA = 2: 1 (v / v)) to give the target compound Inv-86 (3.39 g, yield 43%).

GC-Mass (calculated: 631.24 g / mol, measured: 631 g / mol)

[Synthesis Example 6] Synthesis of Inv-89

IC-4 (5 g, 12.49 mmol) and 4- (3-chlorophenyl) -2,6-dihydrothiophene were used in the place of IC-1 (5 g, 12.49 mmol) and 4-chloro-2,6- (6.1 g, yield 71%) was obtained by carrying out the same procedure as in Synthesis Example 2, except that -diphenylpyrimidine (5.15 g, 14.98 mmol) was used.

GC-Mass (calculated: 706.27 g / mol, measured: 706 g / mol)

[Synthesis Example 7] Synthesis of Inv-132

Inv-132 (5.91 g, yield 75%) was obtained in the same manner as in Synthesis Example 2 except that IC-7 (5 g, 12.49 mmol) was used instead of IC-1.

GC-Mass (theory: 630.24 g / mol, measured: 630 g / mol)

[Synthesis Example 8] Inv-133 synthesis

Except that IC-7 (5 g, 12.49 mmol) and 3-bromo-N, N-diphenylaniline (6.07 g, 18.73 mmol) were used in place of IC-1 and 6-bromo-2,3'- The procedure of Synthesis Example 1 was repeated to obtain Inv-133 (4.02 g, yield 50%) as a target compound.

GC-Mass (calculated: 643.26 g / mol, measured: 643 g / mol)

[Synthesis Example 9] Synthesis of Inv-218

Except that IC-13 (5 g, 12.49 mmol) and 4-chloro-2-phenylpyrimidine (5.15 g, 14.98 mmol) were used in place of IC-1 and 4-chloro-2,6-diphenylpyrimidine. , The target compound Inv-218 (4.43 g, yield 64%) was obtained.

GC-Mass (calculated: 554.21 g / mol, measured: 554 g / mol)

[Synthesis Example 10] Synthesis of Inv-219

The same procedure as in Synthesis Example 2 was carried out except that IC-13 (5 g, 12.49 mmol) and 2-chloroquinoline (2.45 g, 14.98 mmol) were used in place of IC-1 and 4-chloro-2,6-diphenylpyrimidine Inv-219 (4.28 g, yield 65%) was obtained as a target compound.

GC-Mass (theory: 527.20 g / mol, measured: 527 g / mol)

[Synthesis Example 11] Synthesis of Inv-250

Except that IC-15 (5 g, 12.49 mmol) and 4'-bromobiphenyl-4-carbonitrile (4.83 g, 18.73 mmol) were used in place of IC-1 and 6-bromo-2,3'-bipyridine The procedure of Example 1 was repeated to obtain Inv-250 (3.46 g, yield 48%) as a target compound.

GC-Mass (calculated: 577.22 g / mol, measured: 577 g / mol)

[Synthesis Example 12] Synthesis of Inv-255

IC-15 (5 g, 12.49 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (5.15 g, 14.98 mmol), the target compound Inv-255 (6.1 g, yield 69%) was obtained in the same manner as in Synthesis Example 2. [

GC-Mass (707.27 g / mol, measured: 707 g / mol)

[Synthesis Example 13] Synthesis of Inv-344

Except using IC-21 (5 g, 12.00 mmol) and 4- (4-chlorophenyl) -2,6-diphenylpyrimidine (4.95 g, 14.98 mmol) instead of IC-1 and 4-chloro-2,6-diphenylpyrimidine , The target compound Inv-344 (5.81 g, yield 67%) was obtained in the same manner as in Synthesis Example 2.

GC-Mass (calculated: 722.25 g / mol, measured: 722 g / mol)

[Synthesis Example 14] Synthesis of Inv-371

IC-23 (5 g, 12.00 mmol) was dissolved in DMF (100 ml) under nitrogen, to which NaH (0.72 g, 30.01 mmol) was added and the mixture was stirred for 1 hour. Then, 2-chloro-4,6-diphenyl-1,3,5-triazine (6.43 g, 24.01 mmol) dissolved in 100 ml of DMF was slowly added. After stirring for 3 hours, the reaction was terminated and the mixture was filtered through silica, washed with water and methanol, and then the solvent was removed. The solvent-removed solid was purified by column chromatography (Hexane: EA = 2: 1 (v / v)) to give the target compound Inv-371 (3.58 g, yield 46%).

GC-Mass (calculated: 647.21 g / mol, measured: 647 g / mol)

[Synthesis Example 15] Synthesis of Inv-487

The procedure of Synthesis Example 1 was repeated except that IC-31 (5 g, 12.49 mmol) was used instead of IC-12 to obtain the target compound Inv-487 (3.39 g, yield 49%).

GC-Mass (calculated: 554.21 g / mol, measured: 554 g / mol)

[Synthesis Example 16] Synthesis of Inv-492

Inv-492 (5.91 g, yield 75%) was obtained in the same manner as in Synthesis Example 2, except that IC-31 (5 g, 12.49 mmol) was used instead of IC-1.

GC-Mass (theory: 630.24 g / mol, measured: 630 g / mol)

[Synthesis Example 17] Synthesis of Inv-629

Except that IC-41 (5 g, 12.49 mmol) and 4- (4-chlorophenyl) -2,6-diphenylpyrimidine (5.14 g, 14.98 mmol) were used instead of IC-1 and 4-chloro-2,6- The procedure of Synthesis Example 2 was repeated to obtain Inv-629 (6.35 g, yield 72%) as a target compound.

GC-Mass (calculated: 706.27 g / mol, measured: 706 g / mol)

[Synthesis Example 18] Synthesis of Inv-630

IC-41 (5 g, 12.49 mmol) and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (5.15 g, 14.98 mmol), the target compound Inv-630 (6.19 g, yield 70%) was obtained.

GC-Mass (707.27 g / mol, measured: 707 g / mol)

[Synthesis Example 19] Synthesis of Inv-636

Except that IC-42 (5 g, 12.49 mmol) and 2-bromo-6-phenylpyridine (4.38 g, 18.73 mmol) were used in place of IC-1 and 6-bromo-2,3'-bipyridine 1, the target compound Inv-636 (3.53 g, yield 51%) was obtained.

GC-Mass (calculated: 553.22 g / mol, measured: 553 g / mol)

[Synthesis Example 20] Synthesis of Inv-637

Inv-637 (2.91 g, yield 42%) was obtained in the same manner as in Synthesis Example 1, except that IC-42 (5 g, 12.49 mmol) was used instead of IC-1.

GC-Mass (calculated: 554.21 g / mol, measured: 554 g / mol)

[Examples 1 to 20] Preparation of green organic electroluminescent device

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

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

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

[Comparative Example 1] Production of green organic electroluminescent device

A device was prepared in the same manner as in Example 1, except that CBP was used instead of the Inv-13 compound of Synthesis Example 1 as a luminescent host material in the formation of the light emitting layer.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , CBP and BCP used in Examples 1 to 20 and Comparative Example 1 are as follows.

[Evaluation Example 1]

The driving voltage, current efficiency and emission peak at the current density of 10 mA / cm 2 were measured for each of the green organic electroluminescent devices prepared in Examples 1 to 20 and Comparative Example 1, 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-13 6.83 517 39.1 Example 2 Inv-24 6.81 517 40.7 Example 3 Inv-26 6.76 516 40.5 Example 4 Inv-27 6.79 516 39.7 Example 5 Inv-86 6.83 517 39.1 Example 6 Inv-89 6.81 517 39.2 Example 7 Inv-132 6.83 518 38.8 Example 8 Inv-133 6.83 517 39.1 Example 9 Inv-218 6.83 517 39.1 Example 10 Inv-219 6.81 517 40.7 Example 11 Inv-250 6.76 516 40.5 Example 12 Inv-255 6.79 516 39.7 Example 13 Inv-344 6.83 517 39.1 Example 14 Inv-371 6.79 517 39.8 Example 15 Inv-487 6.75 515 41.5 Example 16 Inv-492 6.71 516 38.4 Example 17 Inv-629 6.72 517 41.2 Example 18 Inv-630 6.88 519 38.5 Example 19 Inv-636 6.88 516 39.2 Example 20 Inv-637 6.81 517 40.7 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, when the compound of the present invention was used for the light emitting layer of the green organic electroluminescent device (Examples 1 to 20), the conventional CBP was used for the light emitting layer of the green organic electroluminescent device (Comparative Example 1) It was confirmed that the efficiency and the driving voltage were excellent.

Claims (9)

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,
And the remaining of Y ₁ to Y ₄ which do not form a condensed ring of formula (2) are each independently C (R ₁ ), wherein a plurality of R _{1 s} are the same as or different from each other,
(2)

In Formula 2,
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;
Y ₅ to Y ₈ are independently C (R ₂ ), wherein the plurality of R _{2 s} are the same as or different from each other,
(3)

In Formula 3,
Y ₉ to Y ₁₂ each independently represent C (R ₃ ), wherein a plurality of R _{3 s} may be the same as or different from each other,
In the above Formulas 1 to 3,
X &lt; ₁ &gt; is O or S,
X ₂ and X ₃ are each independently N or C (R ₄ ), wherein when R ₄ is plural, a plurality of R _{4 s} are the same as or different from each other,
X ₄ and X ₅ are each independently N (Ar ₁ ) or C (Ar ₂ ) (Ar ₃ ), wherein at least one of X ₄ and X ₅ is C (Ar ₂ ) (Ar ₃ )
R ₁ to R ₃ and Ar ₁ are each independently hydrogen, deuterium, halogen, cyano, amino, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₆ ~ C ₄₀ heteroaryl group, the aryl group, the number of nuclear atoms of 5 to ₄₀ C ₆ ~ C 40 aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C _A C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~ C ₄₀ aryl selected from the group consisting of silyl groups or as in the combined group and the adjacent may form a condensed ring,
R ₄ is selected from the group consisting of hydrogen, deuterium, C ₁ to C ₄₀ alkyl groups and C ₆ to C ₄₀ aryl groups,
Ar ₂ and Ar ₃ are each independently selected from the group consisting of hydrogen, deuterium, C ₁ to C ₄₀ alkyl groups and C ₆ to C ₄₀ aryl groups,
Wherein R ₁ to R ₃ and an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, alkylsilyl group, an alkyl boronic of Ar ₁ An aryl group, a phosphine group, a phosphine oxide group and an arylsilyl group, and the alkyl and aryl groups of R ₄ , Ar ₂ and Ar ₃ are each independently selected from the group consisting of deuterium, halogen, cyano, amino, C ₁ to C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, A C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, C group of ₁ to alkylboronic of C _40, C ₆ ~ C ₄₀ aryl boron group, C ₁ to C ₄₀ in the phosphine group, C ₁ to C ₄₀ phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group consisting of Substituted or unsubstituted by one or more substituent species selected from may be unsubstituted. The method according to claim 1,
Wherein the compound represented by the formula (1) 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. The method according to claim 1,
Wherein the compound represented by 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. delete The method according to claim 1,
When X ₄ is C (Ar ₂ ) (Ar ₃ ), X ₅ is N (Ar ₁ )
When X ₅ is C (Ar ₂ ) (Ar ₃ ), X ₄ is N (Ar ₁ ). delete The method according to claim 1,
Wherein R ₁ to R ₃ and Ar ₁ are each independently hydrogen, deuterium, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₄₀ . 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 3, 5 and 7. 9. The method of claim 8,
Wherein the organic compound layer containing the compound is a light emitting layer.