KR20140114490A - An electroluminescen compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic light-emitting compound represented by chemical formula 1. An organic electroluminescent device comprising the organic light-emitting compound in the present invention has excellent power efficiency, light-emitting efficiency, and long life cycle because the present invention can be operated by a lower driving-voltage in comparison to a device comprising conventional phosphorescent host materials. [Chemical formula 1].

Description

[0001] The present invention relates to an organic electroluminescent compound and an electroluminescent device comprising the same,

The present invention relates to an organic light emitting compound and an organic electroluminescent device including the same.

In recent years, organic light emitting devices capable of being driven by a low voltage in a self-emission type are superior in viewing angle and contrast ratio compared to a liquid crystal display, which is a mainstream of a flat panel display device, require no backlight and are lightweight and thin, And has been attracting attention as a next generation display device.

An organic electroluminescent device is a device that injects electric charge into an organic light emitting layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode) to form an electron and a hole.

The organic electroluminescent device can be formed on a transparent substrate that can be made of plastic and can be driven at a voltage as low as 10 V or less as compared with a plasma display panel or an inorganic electroluminescent display and has a relatively low power consumption , And has an advantage of excellent color. In addition, organic electroluminescent devices are capable of displaying three colors of green, blue, and red, and thus are attracting much attention as next-generation rich color display devices.

The most important factor determining the luminous efficiency in an organic electroluminescent device is a light emitting material. However, the development of a phosphorescent material on a light-emitting mechanism is one of the ways that the luminous efficiency can be improved more theoretically. Accordingly, a variety of phosphorescent materials have been developed to date, In particular, CBP is the most widely known phosphorescent host material so far, and an organic electroluminescent device using a BALq derivative as a host is known.

However, an organic electroluminescent device using a phosphorescent material has a significantly higher current efficiency than a device using a fluorescent material. However, when a material such as BAlq or CBP is used as a host of a phosphorescent material, There is no significant advantage in terms of power efficiency due to a high voltage and satisfactory level of life of the device can not be achieved, and development of a more stable and high-performance host material is required.

SUMMARY OF THE INVENTION Accordingly, it is an object of the present invention to provide an organic luminescent compound having a luminescent efficiency higher than that of a conventional material, and at the same time having improved power efficiency and longevity.

The present invention also provides an organic electroluminescent device with high efficiency and long life by employing the organic electroluminescent compound as a light emitting material.

In order to solve the above problems, the present invention provides an organic luminescent compound represented by the following formula (1)

The organic electroluminescent device includes at least one organic electroluminescent compound.

[Chemical Formula 1]

Each substituent in the above formula (1) will be described later.

The organic electroluminescent device may include a first electrode, a second electrode, and at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes at least one organic electroluminescent compound .

The organic layer may include at least one selected from a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

In addition, the organic light emitting compound may be used as a host, and the organic layer may further include one or more dopant compounds.

The organic electroluminescent device may further include one or more organic electroluminescent layers emitting blue, red, or green light to emit white light.

The organic electroluminescent device employing the organic electroluminescent compound according to the present invention has a lower driving voltage than the conventional electroluminescent host material and has excellent power efficiency and luminous efficiency and long life.

1 is a conceptual diagram illustrating an organic electroluminescent device having a multilayer structure according to an embodiment of the present invention.

Hereinafter, the present invention will be described in more detail.

An aspect of the present invention relates to an organic luminescent compound represented by the following formula (1).

[Chemical Formula 1]

In the above formula (1), A ₁ to A ₈ are the same as or different from each other and each independently N or CR ₀ .

B is selected from the following formulas (B1) to (B19).

[Formula B1] [Formula B2]

[Formula B3] [Formula B4]

(B5)

[Formula B6]

(B7)

(B8)

(B9)

(B10)

[B11]

(B12)

(B13)

(B14)

[B15]

(B16)

[Chemical formula B17]

[Formula B18]

[Chemical formula B19]

In the above formulas (1) and (B1) to (B19), Z ₁ to Z ₄ are N or CR ₅ to CR ₈ .

R and R ₀ to R ₁₇ are the same or different and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, A substituted or unsubstituted C2 to C60 heteroaryl group, a substituted or unsubstituted C3 to C60 cycloalkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C1 to C60 alkoxy group, Or an unsubstituted aryloxy group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms. A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms.

Further, Cy is a substituted or unsubstituted cycloalkyl group having 3 to 8 carbon atoms.

In addition, Y is _{CR 18 R 19, NR 20,} O, S, SiR 21 R 22, GeR 23 R 24, PR 25, PR 26 (= O), C = O, BR 27.

X and X < _{1 >} are each independently a single bond or a single bond or a CR ₂₈ R ₂₉ , NR ₃₀ , O, S, SiR ₃₁ R ₃₂ , GeR ₃₃ R ₃₄ , PR ₃₅ , PR _{36 37} .

W ₁ to W ₄ are each independently CR ₃₈ to CR ₄₁ , and W ₁ to W ₄ Are adjacent to each other to combine with Q ₁ to Q ₃ to form a fused ring.

L ₁ and L ₂ each independently represents a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylene group having 2 to 60 carbon atoms Substituted or unsubstituted C2-C60 alkynylene groups, substituted or unsubstituted C3-C60 alkynylene groups, substituted or unsubstituted C2- Substituted or unsubstituted C2-C60 heterocycloalkylene group, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 arylene group and substituted Or a substituted or unsubstituted C2-C60 heteroarylene group in which at least one unsubstituted C3-C30 cycloalkyl is fused.

Of said R ₁₈ to R ₄₁ is the R ₀ to R as defined in _17, and m and m 'is an integer from 1 to 2, n and n' is an integer of 0 to 3, o is 0 to 3 And p is an integer of 1 to 3.

According to a preferred embodiment of the present invention, the above-mentioned formulas (B1) to (B19) may be any one selected from the following structural formula (1).

[Structural formula 1]

In the [formula _1], R 1 to _{R 17, X, X 1,} Y, Z 1 to _{Z 4, L 2, Cy,} m, m ', n', p and W ₁ to W ₄ have the Formula 1], and W ₁ to W ₄ Are bonded to Q ₁ to Q ₄ to form a fused ring.

는 하기 C1 내지 C8중에서 선택되는 어느 하나일 수 있다.In addition,

May be any one selected from the following C1 to C8.

C1 C2 C3 C4

C5 C6 C7 C8

In the above C1 to C8, - denotes a site bonded to a structural formula, and R 'is the same as the definition of R.

Wherein R and R ₀ to R ₄₁ , Cy, X, X ₁ , Y, Z ₁ to Z ₄ and W ₁ to W ₄ , L ₁ and L ₂ are independently selected from the group consisting of hydrogen, deuterium, cyano, An alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 2 to 40 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, an arylamino group having 1 to 30 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, Which may be further substituted with at least one substituent selected from the group consisting of a halogen atom, an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 6 to 40 carbon atoms, an aryloxy group having 6 to 40 carbon atoms, an alkylsilyl group having 1 to 30 carbon atoms, and an arylsilyl group having 6 to 40 carbon atoms, R ₀ to R ₄₁ , Cy, X, X ₁ , Y, Z ₁ to Z ₄ , W ₁ to W ₄ , L ₁ and L ₂ may combine with each other to form a saturated or unsaturated ring.

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic layer interposed between the first electrode and the second electrode, And at least one organic luminescent compound represented by the following formula (1).

The organic layer includes at least one selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and the organic light emitting compound according to the present invention is contained in the light emitting layer and used as a phosphorescent host compound.

In addition, the light emitting layer may further include at least one phosphorescent dopant compound in addition to the organic electroluminescent compound represented by Formula 1, and the phosphorescent dopant compound to be applied to the organic electroluminescent device according to the present invention is not particularly limited, , And at least one compound selected from compounds represented by the following formulas [A-1] to [J-1].

[General Formula A-1]

ML ₁ L ₂ L ₃

Wherein M is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, preferably Ir, Pt, Pd, Rh, Re , Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag.

L ₁ , L ₂ and L ₃ are the same or different from each other as ligands, and each independently selected from the following structural formula [D], but are not limited thereto.

In the following [structural formula D], " * " represents a site coordinated to the metal ion M. [

[Structural formula D]

In the above structural formula D,

A substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1- A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, A substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, an unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms and a substituted or unsubstituted arylsilyl Can be selected.

Each R is independently selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cyano group, a halogen group, May be further substituted with one or more substituents selected.

Further, the R may be connected to each adjacent substituent by alkylene or alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring.

The L may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring.

According to a preferred embodiment of the present invention, the dopant represented by the above-mentioned [formula A-1] may be any one selected from the following compounds.

[Formula B-1]

In the above general formula B-1,

M ^A1 represents the same metal ion as defined in the above-mentioned [formula A-1], and Y ^A11 , Y ^A14 , Y ^A15 and Y ^A18 Each independently represent a carbon atom or a nitrogen atom, Y ^A12, Y ^A13, Y ^A16 and Y ^A17 each independently represents a substituted or unsubstituted carbon atoms, a substituted or unsubstituted nitrogen atom, an oxygen atom, a sulfur atom, the L ^A11 , L ^A12 , L ^A13 and L ^A14 each represent a linking group as defined above, and Q ^A11 and Q ^A12 represent a partial structure containing an atom bonding to M ^A1 .

Exemplary structures of the compound represented by the above-mentioned general formula B-1 are shown below, but the present invention is not limited thereto.

[Formula C-1]

In the above general formula (C-1)

M ^B1 is the represents the same metal ion as defined from the following formula ^{A-1], Y B11,} Y B14, Y B15 and Y ^B18 represents a carbon atom or a nitrogen atom, each independently, Y ^B12, Y ^B13, Y ^B16 and ^YB17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom or a sulfur atom, L ^B11 , L ^B12 , L ^B13 and L ^B14 represent a linking group, Q ^B11 , Q ^B12 represents a partial structure containing an atom bonding to M ^B1 .

Exemplary structures of the compound represented by the above-mentioned general formula C-1 are shown below, but the present invention is not limited thereto.

[Formula D-1]

In the above general formula (D-1)

M ^C1 represents a metal ion the same as defined in formula A-1, R ^C11 and R ^C12 each independently represent a hydrogen atom, a substituent which is connected to each other to form a 5-membered ring, R ^C13 and R ^C14 each independently represent a hydrogen atom, a substituent which is mutually connected to each other to form a 5-membered ring, or a substituent which does not have any bond to each other; G ^C11 and G ^C12 each independently represent a nitrogen atom, a substituted or non- L ^C11 and L ^C12 represent a linking group, and Q ^C11 and Q ^C12 represent a partial structure containing an atom bonding to M ^C1 .

Exemplary structures of the compound represented by the above-mentioned general formula (D-1) are shown below, but the present invention is not limited thereto.

[Formula E-1]

In the above general formula E-1,

M ^D1 represents the same metal ion as defined in formula (A-1), G ^D11 and G ^D12 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom, and J ^D11 , J ^D12 , J ^D13 , J ^D14 each independently represents an atomic group necessary for forming a five-membered ring, and L ^D11 and L ^D12 represent a linking group.

Exemplary structures of the compound represented by the above-mentioned [formula E-1] are shown below, but the present invention is not limited thereto.

[Formula F-1]

In the above general formula F-1,

M ^E1 is above represents the same metal ion as defined from the following formula ^{A-1], J E11,} J E12 represents a group of atoms necessary haneundedo form a 5-membered ring, each ^{independently, G E11, G E12, G} E13 and G ^E14 each independently represents a nitrogen atom, a substituted or unsubstituted carbon atom, and Y ^E11 , Y ^E12 , Y ^E13 and Y ^E14 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom.

Exemplary structures of the compound represented by the above-mentioned general formula F-1 are shown below, but the present invention is not limited thereto.

[Formula G-1]

In the above general formula G-1,

M ^F1 represents the same metal ion as defined in the above-mentioned [formula A-1]

L ^F11 , L ^F12 and L ^F13 represent a linking group, R ^F11 , R ^F12 , R ^F13 and R ^F14 represent substituents, R ^F11 and R ^F12 , R ^F12 And R ^F13 , R ^F13 and R ^F14 may be connected to form a ring, wherein the ring formed by R ^F1 and R ^F12 , R ^F13 and R ^F14 is a 5-membered ring. And Q ^F11 and Q ^F12 represent a partial structure containing an atom bonding to M ^F1 .

Exemplary structures of the compound represented by the above-mentioned general formula G-1 are shown below, but the present invention is not limited thereto.

[Formula H-1] [Formula H-2] [Formula H-3]

In the above general formula H-1,

R ¹¹ and R ¹² are alkyl, aryl or heteroaryl groups.

Q11 and q12 may be an integer of 0 to 4, preferably 0 to 2. The substituent may be a fused ring together with the adjacent substituents.

When q11 and q12 are 2 to 4, a plurality of R11 and R12 are the same or different.

L ¹ is a ligand which binds to platinum and is preferably a ligand capable of forming an ortho metal platinum complex, a nitrogen-containing heterocyclic ligand, a diketone ligand or a halogen ligand, more preferably an ortho metal ) Ligand forming a platinum complex, a bipyridyl ligand, or a phenanthroline ligand.

n ¹ is an integer of 0 to 3, preferably 0, m ¹ is 1 or 2, and preferably 2.

It is preferable that n ¹ and m ¹ are such that the metal complex represented by the above-mentioned [formula H-1] is a neutral complex.

R ²¹ , R ²² , n ² , m ² , q ²² and L ² are the same as R ¹¹ , R ¹² , n ¹ , m ¹ , q ¹² and L ^{1 in the} general formula H-2 , q ²¹ is an integer of 0 to 2, and 0 is preferable.

Wherein R ³¹ , n ³ , m ³ and L ³ are the same as R ¹¹ , n ¹ , m ¹ and L ¹ , q ³¹ is an integer of 0 to 8, 0 to 2 is preferable, and 0 is more preferable.

Examples of the specific compounds of the above-mentioned general formulas H-1 to H-3 are shown below, but the present invention is not limited thereto.

[Formula I-1]

In the above general formula I-1,

Ring A, ring B, ring C and ring D represents a nitrogen-containing heterocyclic ring which may have a substituent, and the remaining two rings may be substituted with an aryl ring or a hetero ring which may have a substituent And may form a condensed ring with ring A and ring B, ring A and ring C and / or ring B and ring D, respectively.

X ¹ , X ² , X ³ and X ⁴ represent a nitrogen atom in which two of them coordinate to a platinum atom, and the remaining two represent a carbon atom or a nitrogen atom.

Q ¹ , Q ² and Q ³ each independently represent a divalent atom (or a bond), but Q ¹ , Q ² and Q ³ do not simultaneously represent a bond.

^{Two of} Z ¹ , Z ² , Z ³ and Z ⁴ represent coordinate bond, and the remaining two represent a covalent bond, an oxygen atom or a sulfur atom.

Examples of the specific compounds of the above-mentioned general formula I-1 include, but are not limited to, the following.

[Formula J-1]

In the above general formula J-1,

M represents the same metal ion as defined in the above-mentioned [formula A-1], Ar1 represents a substituted or unsubstituted cyclic structure, and two azomethine bonds (-C = N- ), The nitrogen atom (N) binds to the M, respectively, and forms a three-dimensional ligand which is bonded at the 3-position to the M as a whole.

Further, in Ar 1, C represents a carbon atom constituting a ring structure represented by Ar 1. R 1 and R 2 may be the same or different and each represents a substituted or unsubstituted alkyl group or aryl group, and L represents a one-dimensional ligand.

In the above general formula J-1, it is preferable that M is Pt. The above-mentioned Ar1 is preferably selected from a 5-membered ring, a 6-membered ring and condensed ring group thereof.

Examples of the specific compounds of the above-mentioned general formula J-1 include, but are not limited to, the following.

In addition, the organic light emitting layer according to the present invention may further include various dopant compounds in addition to the dopant compounds.

The organic electroluminescent device according to the present invention may further include at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron blocking layer, a hole blocking layer, an electron transporting layer and an electron injecting layer in addition to the light emitting layer. May be used for the hole injecting layer, the hole transporting layer, the electron injecting layer, and the electron transporting layer in addition to the light emitting layer.

As a specific example, a hole transport layer (HTL) may be further stacked, and an electron transport layer (ETL) may be further stacked between the cathode and the organic emission layer. An electron donor molecule having a low ionization potential is used as the material of the hole transport layer. A diamine, triamine or tetraamine derivative having a basic skeleton of triphenylamine is used as the material of the hole transport layer. It is widely used.

In the present invention, the material for the hole transport layer is not particularly limited as long as it is commonly used in the art. For example, N, N'-bis (3-methylphenyl) -N, N'- 1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine (? -NPD).

A hole injection layer (HIL) may be additionally formed on the lower portion of the hole transport layer. The material for the hole injection layer is not particularly limited as long as it is commonly used in the art. For example, (4,4 ', 4 "-tri (N-carbazolyl) triphenylamine), m-MTDATA (4,4', 4" -tris- (3-methylphenylphenylamino) triphenylamine).

In addition, the electron transport layer used in the organic electroluminescent device according to the present invention can transport electrons supplied from the cathode smoothly to the organic luminescent layer and inhibit the movement of holes which are not bonded in the organic luminescent layer, .

The material of the electron transport layer is not particularly limited as long as it is commonly used in the art. For example, oxadiazole derivative PBD, BMD, BND or Alq ₃ can be used.

Meanwhile, an electron injection layer (EIL) may be further formed on the electron transport layer to facilitate injection of electrons from the cathode to ultimately improve power efficiency. The electron injection layer material As long as it is commonly used in the art, it can be used without any particular limitation. For example, materials such as LiF, NaCl, CsF, Li ₂ O, and BaO can be used.

The organic electroluminescent device according to the present invention can be used for a display device, a display device, an element for a single color or a white light, and the like.

1 is a cross-sectional view showing the structure of an organic electroluminescent device of the present invention. The organic electroluminescent device according to the present invention includes an anode 20, a hole transport layer 40, an organic emission layer 50, an electron transport layer 60 and a cathode 80, The electron injecting layer 70 may be further formed. In addition, one or two intermediate layers may be further formed, or a hole blocking layer or an electron blocking layer may be further formed.

The organic electroluminescent device of the present invention and its manufacturing method will be described with reference to FIG. First, an anode electrode material is coated on the substrate 10 to form an anode 20. Here, as the substrate 10, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity are used.

A hole injection layer 30 is formed on the anode 20 by vacuum thermal deposition or spin coating. Subsequently, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating on the hole transport layer 30 above the hole injection layer 30.

A hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method to form a thin film on the organic light emitting layer 50 can do. In the case where holes are injected into the cathode through the organic light-emitting layer, the lifetime and the efficiency of the device are reduced, and thus the hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level . In this case, the hole blocking material to be used is not particularly limited, but it is required to have an ionization potential higher than that of the light emitting compound while having electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

After the electron transport layer 60 is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode forming metal is deposited on the electron injection layer 70 in a vacuum heat- And the cathode 80 is formed by vapor deposition to complete the organic EL device. Here, as the metal for forming the cathode, lithium, magnesium, aluminum, aluminum-lithium, calcium, magnesium-magnesium, Mg-Ag), and a transmissive cathode using ITO or IZO can be used to obtain a top light-emitting device.

According to another embodiment of the present invention, at least one layer selected from the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer and the electron injecting layer is formed by a single molecular deposition method or a solution process And the organic electroluminescent device according to the present invention can be used for a display device, a display device, and a monochromatic or white illumination device.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims. It will be clear to those who have knowledge.

[Synthesis Example 1] Synthesis of Compound 1

Synthesis of [Reaction Scheme 1-1] [Intermediate 1-a]

[Intermediate 1-a]

9-Nitrophenanthrene (62.5 g, 280 mmol), methyl cyanoacetate (83.3 g, 840 mmol), potassium cyanide (20.1 g, 308 mmol) and potassium hydroxide (31.5 g, 560 mmol) were added and stirred. Then, 630 mL of dimethylformamide was added thereto, followed by stirring at 60 ° C overnight. After concentration under reduced pressure at room temperature, 300 mL of a 10% sodium hydroxide aqueous solution was added, and the mixture was refluxed for about 1 hour. Extracted with ethyl acetate and then separated by column chromatography. Recrystallization from toluene and heptane gave 33 g (yield 54%) of [intermediate 1-a].

[Synthesis of Reaction Scheme 1-2] [Intermediate 1-b]

[Intermediate 1-b]

[Intermediate 1-a] (32.5 g, 149 mmol) obtained in the above Reaction Scheme 1-1 was placed in 300 mL of tetrahydrofuran and stirred. 87.4 mL (297 mmol) of phenylmagnesium bromide (3.0 M in Et ₂ O) was added dropwise and refluxed at 0 ° C for about 1 hour. Ethyl chloroformate (19.4 g, 179 mmol) was added dropwise and refluxed for about 1 hour. The aqueous ammonium chloride solution was added until it became slightly acidic and washed with water and heptane to give 40.3 g (yield 84%) of [intermediate 1-b].

Synthesis of [Scheme 1-3] [Intermediate 1-c]

[Intermediate 1-c]

[Intermediate 1-b] (35.4 g, 110 mmol) obtained in the above Reaction Scheme 1-2 was placed in about 80 mL of phosphorus oxychloride and refluxed overnight. After cooling to -20 ° C, approximately 400 mL of distilled water was slowly added. Washed with water, methanol, and heptane, and recrystallized from toluene and heptane to obtain 20 g (yield: 56%) of Intermediate 1-c.

Synthesis of [Reaction Scheme 1-4] [Intermediate 1-d]

[Intermediate 1-d]

(33.3 g, 122 mmol), 4-iodophenylboronic acid (36.2 g, 146 mmol), tetrakis (triphenylphosphine) palladium (7 g, 6 mmol) and potassium carbonate (33.7 g, 244 mol) were added to 150 mL of 1,4-dioxane, 150 mL of toluene and 60 mL of distilled water, and the mixture was refluxed overnight. The mixture was extracted with ethyl acetate and then recrystallized from dichloromethane and acetone to obtain 39.6 g (yield 82%) of [Intermediate 1-d].

[Reaction Scheme 1-5] Synthesis of [Intermediate 1-e]

[Intermediate 1-e]

[Intermediate 1-d] synthesized in the above Reaction Scheme 1-4 was used instead of 2-bromo-9,9-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4, [Intermediate 1-e] (yield: 78%) was obtained using 9H-carbazole-3-ylboronic acid instead of phenylboronic acid.

[Reaction Scheme 1-6] Synthesis of [Compound 1]

[Compound 1]

60% Sodium hydride (2.1 g, 52 mmol) and 50 mL of dimethylformamide were added thereto, followed by stirring for about 30 minutes. [Intermediate 1-e] (19.2 g, 44 mmol) obtained in [Scheme 1-5] and 100 mL of dimethylformamide were added dropwise thereto, followed by stirring for about 1 hour. [Intermediate 1-c] (17.9 g, 52.4 mmol) obtained in the above Scheme 1-3 and 100 mL of dimethylformamide were added thereto and stirred overnight. 600 mL of distilled water was added, and the resulting solid was filtered. And recrystallized with toluene to obtain 18.2 g (yield: 56%) of [Compound 1].

MS (MALDI-TOF): 739.30 m / z [M ⁺ ] &^lt;

[Synthesis Example 2] Synthesis of Compound 2

Synthesis of [Reaction Scheme 2-1] [Intermediate 2-a]

[Intermediate 2-a]

[Intermediate 2-a] was obtained in the same manner as in [Reaction Scheme 1-6] except that 6-bromo-1H-indole was used in place of [Intermediate 1-e] (Yield: 84%).

Synthesis of [Reaction Scheme 2-2] [Intermediate 2-b]

[Intermediate 2-b]

[Intermediate 2-a] synthesized in the above Reaction Scheme 2-1 was used instead of the 2-bromo-9,9-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4, [Intermediate 2-b] (yield: 80%) was obtained using 9H-carbazol-3-ylboronic acid instead of phenylboronic acid.

[Reaction 2-3] Synthesis of [Formula 2]

[Compound 2]

[Compound 2] (yield: 58%) was obtained in the same manner as in [Intermediate 2-b] synthesized in the above Reaction Scheme 2-2 instead of Intermediate 1-e used in Reaction Scheme 1-6.

MS (MALDI-TOF): 662.25 m / z [M ⁺ ] &^lt;

[Synthesis Example 3] Synthesis of Compound 3

Synthesis of [Reaction Scheme 3-1] [Intermediate 3-a]

[Intermediate 3-a]

[Intermediate 3-a] was prepared in the same manner as in [Reaction Formulas 1-2] to [Reaction Scheme 1-3], except that pentadecetheliophenylmagnesium bromide was used in place of the phenylmagnesium bromide used in [Reaction Scheme 1-2] Yield: 58%).

Synthesis of [Reaction Scheme 3-2] [Intermediate 3-b]

[Intermediate 3-b]

Bromobenzene (135.1 g, 0.48 mol), palladium acetate (1.3 g, 0.006 mol), aztophos (10 g, 0.02 mol) mol), cesium carbonate (217.5 g, 0.67 mol) and 2500 mL of toluene were charged and refluxed for 6 hours. Ethyl acetate and then separated by column chromatography to obtain 110 g of [intermediate 3-b] (yield 75%).

Synthesis of [Reaction Scheme 3-3] [Intermediate 3-c]

[Intermediate 3-c]

[Intermediate 3-b] (110 g, 0.36 mol) obtained in the above Reaction Scheme 3-2 was added to 1650 mL of diisopropylether and stirred. 419 mL of methylmagnesium bromide was slowly added dropwise, followed by stirring at 50 DEG C for 12 hours. The reaction mixture was extracted with ethyl acetate, and then recrystallized from dichloromethane and hexane to obtain 108 g of [intermediate 3-c] (yield 68%).

Synthesis of [Reaction Scheme 3-4] [Intermediate 3-d]

[Intermediate 3-d]

[Intermediate 3-c] (108 g, 0.36 mol) obtained in the above Reaction Scheme 3-3 and 400 mL of phosphoric acid were added and stirred for 6 hours. After the reaction was completed, excess distilled water was added thereto, stirred, filtered and separated by column chromatography to obtain 75 g (yield 75%) of [intermediate 3-d].

Synthesis of [Reaction Scheme 3-5] [Intermediate 3-e]

[Intermediate 3-e]

[Reaction Scheme 3-1] was repeated except that [Intermediate 3-d] synthesized in the above Reaction Scheme 3-4 was used instead of [Intermediate 1-d] used in the above Reaction Scheme 1-5, [Intermediate 3-e] (yield: 78%) was obtained in the same manner as in [Intermediate 3-a].

[Reaction Scheme 3-6] Synthesis of [Compound 3]

[Compound 3]

(91.9 g, 149 mmol), diphenylamine (21 g, 124 mmol), tris (dibenzylideneacetone) dipalladium (5.7 g, 6.2 mmol) obtained in the above Reaction Scheme 3-5 ), Triturated butylphosphine (3.8 g, 18.6 mmol) and sodium tertiary butoxide (23.8 g, 248 mmol) were added to 250 mL of toluene and stirred at 110 ° C for 9 hours. After cooling to room temperature, the mixture was extracted with dichloromethane and then separated by column chromatography to obtain 52.5 g (yield: 60%) of [Compound 3].

MS (MALDI-TOF): 705.39 m / z [M ⁺ ] &^lt;

[Synthesis Example 4] Synthesis of Compound 4

Synthesis of [Reaction Scheme 4-1] [Intermediate 4-a]

[Intermediate 4-a]

Instead of 2-bromo-9,9-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4 and using 5-indolylboronic acid instead of 4-iodophenylboronic acid [Intermediate 4-a] (yield: 85%) was obtained.

Synthesis of [Reaction Scheme 4-2] [Intermediate 4-b]

[Intermediate 4-b]

Bromo-9H-carbazole instead of 2-bromo-9,9-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4 and phenylboronic acid [Intermediate 4-b] (yield: 82%) was obtained in the same manner.

Synthesis of [Reaction Scheme 4-3] [Intermediate 4-c]

[Intermediate 4-c]

[Intermediate 4-b] (26.8 g, 0.11 mol) obtained in the above Reaction Scheme 4-2 was dissolved in 200 mL of dimethylformamide and stirred at 0 ° C. En-Bromosuccinimide (20.1 g, 0.11 mol) was dissolved in 100 mL of dimethylformamide and slowly added dropwise over 1 hour. The mixture was stirred at room temperature for 12 hours. Filtered through an excess of distilled water, washed with methanol, and recrystallized from toluene and methanol to obtain 31.5 g (yield: 89%) of Intermediate 4-c.

Synthesis of [Reaction Scheme 4-4] [Intermediate 4-d]

[Intermediate 4-d]

[Intermediate 4-a] synthesized in [Reaction Scheme 4-1] above was used instead of [Intermediate 1-e] used in [Reaction Scheme 1-6] [Intermediate 4-d] (yield: 77%) was obtained in the same manner as in [Intermediate 4-c].

[Reaction Scheme 4-5] Synthesis of [Compound 4]

[Compound 4]

[Compound 4] (yield 52%) was obtained in the same manner as in [Intermediate 4-d] synthesized in the above Reaction Scheme 4-4 instead of Intermediate 1-e used in Reaction Scheme 1-6.

MS (MALDI-TOF): 743.31 m / z [M ⁺ ] &^lt;

[Synthesis Example 5] Synthesis of Compound 5

Synthesis of [Reaction Scheme 5-1] [Intermediate 5-a]

[Intermediate 5-a]

[Intermediate 5-a] was obtained in the same manner as in [Scheme 1-2] to [Scheme 1-3] except that 4-biphenylmagnesium bromide was used in place of the phenylmagnesium bromide used in [Scheme 1-2] Yield: 43%).

Synthesis of [Reaction Scheme 5-2] [Intermediate 5-b]

[Intermediate 5-b]

[Intermediate 5-b] (yield: 80%) was obtained using 5-bromo-1H-indole instead of 2-bromo-9,9- ).

[Synthesis of Reaction Scheme 5-3] [Intermediate 5-c]

[Intermediate 5-c]

[Intermediate 5-b] synthesized in the above Reaction Scheme 5-2 was used instead of the 2-bromo-9,9-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4, [Intermediate 5-c] (yield 78%) was obtained using 1-naphthylboronic acid instead of phenylboronic acid.

Synthesis of [Reaction Scheme 5-4] [Intermediate 5-d]

[Intermediate 5-d]

[Intermediate 5-a] synthesized in the above Reaction Scheme 5-1 was used instead of 2-bromo-9,9-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4 to obtain Intermediate 5-d ] (Yield: 80%).

[Reaction Scheme 5-5] Synthesis of [Compound 5]

[Compound 5]

[Intermediate 5-c] synthesized in [Scheme 5-3] above was used in place of [Intermediate 1-e] used in [Reaction Scheme 1-6] [Compound 5] (yield: 53%) was obtained in the same manner as in [Intermediate 5-d] synthesized.

MS (MALDI-TOF): 775.30 m / z [M ⁺ ] &^lt;

[Synthesis Example 6] Synthesis of Compound 6

Synthesis of [Reaction Scheme 6-1] [Intermediate 6-a]

[Intermediate 6-a]

(72.1 g, 265 mmol) obtained in the above Reaction Scheme 2-1 was dissolved in 576 mL of tetrahydrofuran, and 1.6 M n-butyllithium (182 mL, 291 mmol) was added thereto while stirring at -78 ° C. The mixture was slowly added dropwise and stirred for about 1 hour while maintaining the temperature at -78 ° C. Trimethylborate (41.2 g, 397 mmol) was slowly added dropwise thereto, and then the mixture was stirred at room temperature for about 3 hours. 140 mL of a 1 M aqueous hydrochloric acid solution was added dropwise at room temperature, and the mixture was stirred for 30 minutes. Extraction with ethyl acetate and recrystallization from dichloromethane and hexane gave 47.7 g (yield 76%) of [intermediate 6-a].

Synthesis of [Reaction Scheme 6-2] [Intermediate 6-b]

[Intermediate 6-b]

6-bromo-1H-indole was used instead of 2-bromo-9,9-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4 and, instead of 4-iodophenylboronic acid, [Intermediate 6-b] (yield: 82%) was obtained using [Intermediate 6-a] synthesized in Example 1].

Synthesis of [Scheme 6-3] [Compound 6]

[Compound 6]

[Compound 6] (yield 62%) was obtained in the same manner as in [Intermediate 6-b] synthesized in the above Reaction Scheme 6-2 instead of Intermediate 1-e used in Reaction Scheme 1-6.

MS (MALDI-TOF): 612.23 m / z [M ⁺ ] &^lt;

[Synthesis Example 7] Synthesis of Compound 7

Synthesis of [Reaction Scheme 7-1] [Intermediate 7-a]

[Intermediate 7-a]

4-Bromoaniline (100 g, 0.58 mol) was slowly added to 600 mL of distilled water and 1000 mL of concentrated hydrochloric acid. Sodium nitrite (40 g, 0.58 mol) was dissolved in 400 mL of distilled water at 0 ° C and then slowly added dropwise. Tin (II) chloride (600 g, 2.9 mol) dissolved in 1200 mL of concentrated hydrochloric acid was added dropwise thereto, followed by stirring at room temperature for about 3 hours. And dried under reduced pressure to obtain 114 g (yield: 88%) of [intermediate 7-a].

Synthesis of [Reaction Scheme 7-2] [Intermediate 7-b]

[Intermediate 7-b]

[Intermediate 7-a] (68.5 g, 0.31 mol) and 2-butanone (22.1 g, 0.31 mol) obtained in the above Reaction Scheme 7-1 were added to 700 mL of ethanol and stirred at 65 ° C for 1 hour. The mixture was cooled to room temperature and washed with ethanol. And dried under reduced pressure to obtain 48 g (yield 70%) of [intermediate 7-b].

Synthesis of [Reaction Scheme 7-3] [Intermediate 7-c]

[Intermediate 7-c]

(25 g, 0.14 mol), 1,4-dibromobenzene (105 g, 0.43 mol), copper powder (14 g, 0.21 mol), potassium carbonate (60 g, 0.43 mol) and 18-crown-6 (3 g, 0.01 mol) were added to 500 mL of 1,2-dichlorobenzene and refluxed at 180 ° C for 12 hours. The mixture was extracted with ethyl acetate and then subjected to column chromatography to obtain 17 g of [intermediate 7-c] (yield: 36%).

Synthesis of [Reaction Scheme 7-4] [Intermediate 7-d]

[Intermediate 7-d]

[Intermediate 7-d] (yield 78%) was obtained using [Intermediate 7-c] synthesized in the above Reaction Scheme 7-3 instead of Intermediate 2-a used in Reaction Scheme 6-1 above.

Synthesis of [Reaction Scheme 7-5] [Intermediate 7-e]

[Intermediate 7-e]

[Intermediate 7-b] synthesized in the above Reaction Scheme 7-2 was used instead of the 2-bromo-9,9-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4 and 4-iodophenyl [Intermediate 7-e] (yield 69%) was obtained using [Intermediate 7-d] synthesized in the above [Reaction Scheme 7-4] instead of boronic acid.

Synthesis of [Reaction Scheme 7-6] [Compound 7]

[Compound 7]

[Intermediate 7-e] synthesized in the above Reaction Scheme 7-5 was used in place of [Intermediate 1-e] used in the above Reaction Scheme 1-6, and [Reaction Scheme 3-1] [Compound 7] (yield: 56%) was obtained in the same manner as in [Intermediate 3-a].

MS (MALDI-TOF): 719.40 m / z [M ⁺ ] &^lt;

[Synthesis Example 8] Synthesis of Compound 8

Synthesis of [Reaction Scheme 8-1] [Intermediate 8-a]

[Intermediate 8-a]

Phenylhydrazine (44.3 g, 0.41 mol) was added to 150 mL of acetic acid and heated to 60 ° C. 2-Methylcyclichexanone (45.9 g, 0.41 mol) was slowly added dropwise and refluxed for 8 hours. When the reaction was completed, 100 mL of distilled water was added, followed by basification with sodium hydroxide. The mixture was extracted with ethyl acetate and then separated by column chromatography to obtain 63.8 g of [intermediate 8-a] (yield: 84%).

Synthesis of [Reaction Scheme 8-2] [Intermediate 8-b]

[Intermediate 8-b]

The intermediate [8-a] (37 g, 0.2 mol) obtained in the above Reaction Scheme 8-1 was dissolved in 370 mL of toluene, the temperature was lowered to -10 ° C., 185 mL of 1.6 M methyl lithium was slowly added dropwise thereto, Lt; / RTI > The reaction mixture was extracted with ethyl acetate and then subjected to column chromatography to obtain 30.6 g of [Intermediate 8-b] (yield: 76%).

Synthesis of [Reaction Scheme 8-3] [Intermediate 8-c]

[Intermediate 8-c]

[Intermediate 8-b] synthesized in [Reaction Scheme 8-2] above was used in place of [Intermediate 1-e] used in [Reaction Scheme 1-6] [Intermediate 8-c] (yield: 79%).

Synthesis of [Reaction Scheme 8-4] [Intermediate 8-d]

[Intermediate 8-d]

[Intermediate 8-d] (yield: 80%) was obtained in the same manner as in [Intermediate 8-c] obtained in the above Reaction Scheme 8-3 instead of [Intermediate 4-b] used in the above Reaction Scheme 4-3 .

Synthesis of [Reaction Scheme 8-5] [Intermediate 8-e]

[Intermediate 8-e]

Bisphenacyldiboron (21.6 g, 0.09 mol) and bisdiphenylphosphinoferrocene dichloropalladium (2.3 g, 0.003 mol) obtained in the above Reaction Scheme 8-4 (19.6 g, 0.06 mol) ) And potassium acetate (12.9 g, 0.17 mol) were added to 200 mL of toluene and refluxed for 12 hours. After extraction with toluene, the product was separated by column chromatography to obtain 17.4 g (yield 72%) of [Intermediate 8-e].

Synthesis of [Reaction Scheme 8-6] [Intermediate 8-f]

[Intermediate 8-f]

Instead of 2-bromo-9,9-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4, the above 1-amino-4-bromonaphthalene was used instead of 4-iodophenylboronic acid, [Intermediate 8-f] (yield 69%) was obtained using [Intermediate 8-e] synthesized in Reference Example 8-5.

Synthesis of [Reaction Scheme 8-7] [Intermediate 8-g]

[Intermediate 8-g]

(30.7 g, 0.08 mol), 2-bromoiodobenzene (22.6 g, 0.08 mol) and tris (dibenzylideneacetone) dipalladium (1.1 g, 0.08 mol) obtained in the above Reaction Scheme 8-6 0.0001 mol), 1,1'-bis (diphenylphosphino) ferrocene (0.7 g, 0.0001 mol) and sodium tertiarybutoxide (15.3 g, 0.16 mol) were placed in 250 mL of toluene and refluxed for 24 hours. The product was separated by column chromatography to obtain 18.5 g (yield: 43%) of [intermediate 8-g].

Synthesis of [Reaction Scheme 8-8] [Intermediate 8-h]

[Intermediate 8-h]

(16.2 g, 0.03 mol), potassium acetate (4.0 g, 0.04 mol) and tetrakistriphenylphosphine palladium (0.8 g, 0.001 mol) synthesized in the above Reaction Scheme 8-7 were dissolved in dimethyl Formamide in 125 mL and stirred at 150 < 0 > C for 24 hours. The reaction mixture was separated by column chromatography and recrystallized with hexane to obtain 3.5 g (yield: 25%) of Intermediate 8-h.

Synthesis of [Reaction Scheme 8-9] [Compound 8]

[Compound 8]

[Compound 8] (yield: 49%) was obtained in the same manner as in [Intermediate 8-h] synthesized in the above Reaction Scheme 8-8 instead of Intermediate 1-e used in Reaction Scheme 1-6.

MS (MALDI-TOF): 796.36 m / z [M ⁺ ] &^lt;

[Synthesis Example 9] Synthesis of Compound 9

Synthesis of [Synthesis 9-1] [Synthesis of Intermediate 9-a]

[Intermediate 9-a]

[Synthesis of Intermediate 9-a] (yield: 72%) was prepared in the same manner as in [Reaction Scheme 3-3] to [Reaction Scheme 3-4], except that phenylmagnesium bromide was used instead of the methylmagnesium bromide used in [Reaction Formula 3-3] ).

Synthesis of [Reaction Scheme 9-2] [Intermediate 9-b]

[Intermediate 9-b]

[Intermediate 9-b] (yield: 81%) was obtained in the same manner as in 2-methylcyclic pentanone used in the above Reaction Scheme 8-1 instead of 2-methylcyclichexanone.

Synthesis of [Synthesis 9-3] [Intermediate 9-c]

[Intermediate 9-c]

[Intermediate 9-c] (yield: 77%) was obtained in the same manner as in [Intermediate 9-b] synthesized in the above Reaction Scheme 9-2 instead of Intermediate 8-a used in Reaction Scheme 8-2 .

Synthesis of [Reaction Scheme 9-4] [Intermediate 9-d]

[Intermediate 9-d]

6-Bromo-2-naphthol (31.2 g, 0.14 mol) was added to 270 mL of dichloromethane and stirred. Pyridine (14 g, 0.18 mol) was added and the reaction was cooled to 0 ° C. Trifluoromethanesulfonic anhydride (42.3 g, 0.15 mol) was slowly added dropwise and stirred at room temperature for 1 hour. 37.8 g (yield 76%) of [intermediate 9-d] was obtained by column chromatography.

Synthesis of [Reaction Scheme 9-5] [Intermediate 9-e]

[Intermediate 9-e]

[Intermediate 9-c] synthesized in [Reaction Scheme 9-3] above was used instead of [Intermediate 1-e] used in [Reaction Scheme 1-6] [Intermediate 9-e] (yield: 83%) was obtained in the same manner as in the synthesis of [Intermediate 9-d].

Synthesis of [Reaction Scheme 9-6] [Intermediate 9-f]

[Intermediate 9-f]

[Intermediate 9-f] (yield 78%) was obtained in the same manner as Intermediate 9-a synthesized in the above Reaction Scheme 9-1 instead of Intermediate 2-a used in Reaction Scheme 6-1 .

Synthesis of [Reaction 9-7] [Intermediate 9-g]

[Intermediate 9-g]

[Intermediate 9-e] synthesized in the above Reaction Scheme 9-5 was used instead of the 2-bromo-9,9-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4, [Intermediate 9-g] (yield: 72%) was obtained using [Intermediate 9-f] synthesized in the above [Reaction Scheme 9-6] instead of phenylboronic acid.

[Synthesis of Compound 9]

[Compound 9]

[Intermediate 9-g] synthesized in [Reaction Scheme 9-7] above was used instead of [Intermediate 1-e] used in [Reaction Scheme 1-6] [Compound 9] (yield 50%) was obtained in the same manner as in [Intermediate 3-a] synthesized.

MS (MALDI-TOF): 973.51 m / z [M ⁺ ] &^lt;

[Synthesis Example 10] Synthesis of Compound 10

Synthesis of [Synthesis 10-1] [Synthesis of Intermediate 10-a]

[Intermediate 10-a]

[Intermediate 10-a] was prepared in the same manner as in [Reaction Scheme 3-3] to [Reaction Scheme 3-4], except that pyridine-4-ylmagnesium bromide was used in place of the phenylmagnesium bromide used in [Scheme 1-2] (Yield: 54%).

Synthesis of [Reaction Scheme 10-2] [Intermediate 10-b]

[Intermediate 10-b]

4-Bromophenylhydrazine hydrochloride (110 g, 492 mmol) and benzyl phenyl ketone (64 g, 328 mmol) were added to 550 mL of ethanol and refluxed for 12 hours. The reaction mixture was neutralized with a base, extracted with ethyl acetate, and then recrystallized with hexane to obtain 68.3 g of [intermediate 10-b] (yield 40%).

Synthesis of [Reaction Scheme 10-3] [Intermediate 10-c]

[Intermediate 10-c]

[Intermediate 10-c] was obtained by using dibenzohydrazone instead of [Intermediate 8-f] used in the above Reaction Scheme 8-7 and using 9-bromophenanthrene instead of 2-bromoiodobenzene, (Yield: 73%).

Synthesis of [Reaction Scheme 10-4] [Intermediate 10-d]

[Intermediate 10-d]

(30 g, 80.5 mmol), cyclopentanone (6.78 g, 80.5 mmol) and p-toluenesulfonic acid (45.9 g, 241.5 mmol) obtained in the above Reaction Scheme 10-3 were dissolved in 200 mL of ethanol And refluxed for 12 hours. It was basified with sodium hydroxide and extracted with ethyl acetate. The resultant product was separated by column chromatography to obtain 15.7 g (yield 76%) of [intermediate 10-d].

Synthesis of [Reaction Scheme 10-5] [Intermediate 10-e]

[Intermediate 10-e]

[Intermediate 10-d] (20 g, 77.7 mmol) obtained in the above Reaction Scheme 10-4 was added to 120 mL of acetone and stirred. After cooling to 0 ° C, sodium cyanoborohydride (9.7 g, 155.4 mmol) was slowly added dropwise and stirred for 3 hours. After adding 100 mL of distilled water, it was basified with sodium hydroxide and extracted with ethyl acetate. The product was separated by column chromatography to obtain 16.5 g (yield 80%) of [intermediate 10-e].

Synthesis of Intermediate 10-f

[Intermediate 10-f]

[Intermediate 10-e] was used in place of [Intermediate 1-c], and [Intermediate 10-b] was used instead of [Intermediate 1-e] [Intermediate 10-f] (yield: 76%) was obtained in the same manner.

[Reaction formula 10-7] Synthesis of [Compound 10]

[Compound 10]

[Intermediate 10-f] synthesized in [Scheme 10-6] above was used in place of [Intermediate 1-e] used in [Reaction Scheme 1-6] [Compound 10] (yield: 48%) was obtained in the same manner as in [Intermediate 10-a] synthesized.

MS (MALDI-TOF): 831.34 m / z [M ⁺ ] &^lt;

[Synthesis Example 11] Synthesis of Compound 11

Synthesis of [Intermediate 11-a]

[Intermediate 11-a]

[Synthesis of Intermediate 11-a] (yield: 82%) was obtained in the same manner as in [Scheme 8-1] above using 3,4-dimethyl cyclic hexanone instead of 2-methylcyclic hexanone.

Synthesis of [Reaction Scheme 11-2] [Intermediate 11-b]

[Intermediate 11-b]

[Intermediate 11-b] (yield: 83%) was obtained in the same manner as in [Intermediate 11-a] synthesized in the above Reaction Scheme 11-1 instead of Intermediate 10-d used in Reaction Scheme 10-5 .

Synthesis of [Reaction Scheme 11-3] [Intermediate 11-c]

[Intermediate 11-c]

[Intermediate 11-b] synthesized in the above Reaction Scheme 11-2 was used instead of [Intermediate 1-e] used in the above Reaction Scheme 1-6, and penta-diterate iodobenzene was used instead of [Intermediate 1-c] [Intermediate 11-c] (yield: 79%) was obtained in the same manner.

Synthesis of [Reaction Scheme 11-4] [Intermediate 11-d]

[Intermediate 11-d]

[Intermediate 11-d] (yield 80%) was obtained in the same manner as in [Intermediate 11-c] synthesized in the above Reaction Scheme 11-3 instead of Intermediate 4-b used in Reaction Scheme 4-3 .

Synthesis of [Reaction Scheme 11-5] [Intermediate 11-e]

[Intermediate 11-e]

[Intermediate 11-d] synthesized in the above Reaction Scheme 11-4 was used instead of the 2-bromo-9,9-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4, Indolylboronic acid was used in place of phenylboronic acid to obtain [intermediate 11-e] (yield: 80%).

Synthesis of [Formula 11-6] [Compound 11]

[Compound 11]

[Intermediate 11-e] synthesized in [Reaction Scheme 11-5] above was used instead of [Intermediate 1-e] used in [Reaction Scheme 1-6] [Compound 11] (yield 50%) was obtained in the same manner as in [Intermediate 3-a] synthesized.

MS (MALDI-TOF): m / z 726.45 [M ^< ⁺ &^gt;].

[Synthesis Example 12] Synthesis of Compound 12

[Synthesis of Intermediate 12-a]

[Intermediate 12-a]

Instead of 2-bromo-9,9-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4, and using 9D-carbazole-3 instead of 4-iodophenylboronic acid -Yl boronic acid to obtain [intermediate 12-a] (yield: 83%).

Synthesis of [Reaction Scheme 12-2] [Intermediate 12-b]

[Intermediate 12-b]

[Intermediate 12-b] (yield 88%) was obtained in the same manner as [Intermediate 12-a] synthesized in the above Reaction Scheme 12-1 instead of [Intermediate 4-b] used in the above Reaction Scheme 4-3 .

[Synthesis of Intermediate 12-c]

[Intermediate 12-c]

Was obtained by using 1,2,3,4-tetrahydroquinoline instead of [Intermediate 1-e] used in [Reaction Scheme 1-6] above and using pentaduteoleoiodobenzene in place of [Intermediate 1-c] Intermediate 12-c] (yield: 80%).

Synthesis of [Reaction Scheme 12-4] [Intermediate 12-d]

[Intermediate 12-d]

[Intermediate 12-d] (yield: 88%) was obtained in the same manner as in [Intermediate 12-c] synthesized in the above Reaction Scheme 12-3 instead of [Intermediate 4-b] used in the above Reaction Scheme 4-3 .

Synthesis of [Reaction Scheme 12-5] [Intermediate 12-e]

[Intermediate 12-e]

[Intermediate 12-e] (yield: 77%) was obtained in the same manner as in [Intermediate 12-d] synthesized in [Reaction Formula 12-4] instead of [Intermediate 2-a] used in the above Reaction Scheme 6-1 .

Synthesis of Intermediate 12-f

[Intermediate 12-f]

[Intermediate 12-b] synthesized in the above Reaction Scheme 12-2 was used instead of the 2-bromo-9,9'-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4, [Intermediate 12-f] (yield 77%) was obtained in the same manner as in [Intermediate 12-e] synthesized in the above [Reaction Scheme 12-5] instead of phenylboronic acid.

Synthesis of [Reaction Formula 12-7] [Compound 12]

[Compound 12]

[Intermediate 12-f] synthesized in [Reaction Scheme 12-6] above was used in place of [Intermediate 1-e] used in [Reaction Scheme 1-6] [Compound 12] (yield: 51%) was obtained in the same manner as in [Intermediate 3-a] synthesized.

MS (MALDI-TOF): m / z 789.47 [M ^< ⁺ &^gt;].

[Synthesis Example 13] Synthesis of Compound 13

[Synthesis of Intermediate 13-a]

[Intermediate 13-a]

Methylindoline was used in place of [Intermediate 1-e] used in [Reaction Scheme 1-6], and 4-bromo-1-naphthylboronic acid was used in place of [Intermediate 1-c] Intermediate 13-a] (yield: 76%).

Synthesis of [Reaction Scheme 13-2] [Intermediate 13-b]

[Intermediate 13-b]

3-chloro-10H-phenothiazine instead of 2-bromo-9,9-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4 was used instead of 4-iodophenylboronic acid, [Intermediate 13-b] (yield: 77%) was obtained using [Intermediate 13-a] synthesized in Example 13-1.

[Synthesis of Compound 13]

[Compound 13]

[Compound 13] (yield: 53%) was obtained in the same manner as in [Intermediate 13-b] synthesized in the above Reaction Scheme 13-2 instead of Intermediate 1-e used in Reaction Scheme 1-6.

MS (MALDI-TOF): m / z 760.27 [M ^< ⁺ &^gt;].

[Synthesis Example 14] Synthesis of Compound 14

[Synthesis of Intermediate 14-a]

[Intermediate 14-a]

Bromo-9H-carbazole was used in place of [Intermediate 1-e] used in the above Reaction Scheme 1-6, and [Intermediate 14-a] was obtained in the same manner using iodobenzene instead of [Intermediate 1-c] ] (Yield: 86%).

Synthesis of [Reaction Scheme 14-2] [Intermediate 14-b]

[Intermediate 14-b]

[Intermediate 14-a] synthesized in the above Reaction Scheme 14-1 was used instead of the 2-bromo-9,9-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4, Carbazole-3-ylboronic acid instead of phenylboronic acid to obtain [intermediate 14-b] (yield: 80%).

Synthesis of [Compound 14]

[Compound 14]

[Compound 14] (yield 50%) was obtained in the same manner as in [Intermediate 14-b] synthesized in the above Reaction Scheme 14-2 instead of Intermediate 1-e used in Reaction Scheme 1-6.

MS (MALDI-TOF): m / z 712.26 [M ^< ⁺ &^gt;].

[Synthesis Example 15] Synthesis of Compound 15

[Synthesis of Intermediate 15-a]

[Intermediate 15-a]

1,4-Dibromobenzene (15 g, 63.58 mmol) was added to 300 mL of tetrahydrofuran and 1.6 M normal-butyllithium (26.7 mL, 66.76 mmol) was slowly added dropwise at -78 ° C and stirred for 1 hour. 20.6 mL of chlorotriphenylsilane was dissolved in 70 mL of tetrahydrofuran, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was extracted with ethyl acetate and recrystallized from ethyl acetate and methanol to obtain 17.5 g of [intermediate 15-a] (yield 66%).

Synthesis of [Reaction Scheme 15-2] [Intermediate 15-b]

[Intermediate 15-b]

[Intermediate 15-b] (yield: 76%) was obtained in the same manner as Intermediate 15-a synthesized in the above Reaction Scheme 15-1 instead of Intermediate 2-a used in Reaction Scheme 6-1 .

[Synthesis of Intermediate 15-c]

[Intermediate 15-c]

Instead of 2-bromo-9,9-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4, 2-bromonitrobenzene was used instead of 4-iodophenylboronic acid, [Intermediate 15-c] (yield: 97%) was obtained in the same manner as in [Intermediate 15-b].

Synthesis of Intermediate 15-d

[Intermediate 15-d]

[Intermediate 15-c] (82.3 g, 180 mmol) obtained in the above Reaction Scheme 15-3 was added to 400 mL of 1,2-dichlorobenzene, 800 mL of triethylphosphite was added, and the mixture was refluxed at 150 ° C. for 12 hours . The reaction mixture was cooled to room temperature and separated by column chromatography to obtain [intermediate 15-d] (yield 78%).

Synthesis of [Reaction Scheme 15-5] [Intermediate 15-e]

[Intermediate 15-e]

Bromonitrobenzene was used instead of 2-bromo-9,9-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4, and 1-naphthalene boronic acid was used instead of 4- [Intermediate 15-e] (yield: 91%) was obtained in the same manner.

Synthesis of Intermediate 15-f

[Intermediate 15-f]

[Intermediate 15-f] (yield: 81%) was obtained in the same manner as Intermediate 15-e synthesized in the above Reaction Scheme 15-5 instead of Intermediate 15-c used in Reaction Scheme 15-4 .

[Synthesis of Reaction Formula 15-7] [Intermediate 15-g]

[Intermediate 15-g]

[Intermediate 15-g] (94% yield) was obtained in the same manner as in [Intermediate 15-f] synthesized in the above Reaction Scheme 15-6 instead of Intermediate 4-b used in Reaction Scheme 4-3 .

[Reaction formula 15-8] Synthesis of [intermediate 15-h]

[Intermediate 15-h]

[Intermediate 15-d] synthesized in [Reaction Formula 15-4] above was used in place of [Intermediate 1-e] used in [Reaction Scheme 1-6] [Intermediate 15-h] (yield: 86%) was obtained in the same manner using the synthesized [intermediate 15-g].

[Reaction formula 15-9] Synthesis of [Compound 15]

[Compound 15]

[Compound 15] (yield: 47%) was obtained in the same manner as in [Intermediate 15-h] synthesized in the above Reaction Scheme 15-8 instead of Intermediate 1-e used in Reaction Scheme 1-6.

MS (MALDI-TOF): m / z 944.33 [M ^< ⁺ &^gt;].

[Synthesis Example 16] Synthesis of Compound 16

[Synthesis of Intermediate 16-a]

[Intermediate 16-a]

7-Bromo-3,4-dihydro-2H-l, 4-benzothiazine was used instead of 2,3,4,9-tetrahydro-lH-carbazole used in the above Reaction Scheme 7-3, [Intermediate 16-a] (yield 80%) was obtained in the same manner using iodobenzene instead of 1,4-dibromobenzene.

Synthesis of [Reaction Scheme 16-2] [Intermediate 16-b]

[Intermediate 16-b]

[Intermediate 16-a] synthesized in [Scheme 16-1] above was used instead of 2-bromo-9,9-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4, [Intermediate 16-b] (yield: 85%) was obtained by using 3-bromophenylboronic acid instead of phenylboronic acid in the same manner.

[Synthesis of Reaction Formula 16-3] [Intermediate 16-c]

[Intermediate 16-c]

[Intermediate 16-b] synthesized in [Scheme 16-2] above was used instead of 2-bromo-9,9-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4, Indolylboronic acid was used in place of phenylboronic acid, [Intermediate 16-c] (yield: 79%) was obtained in the same manner.

Synthesis of [Scheme 16-4] [Compound 16]

[Compound 16]

[Intermediate 1-c] synthesized in [Reaction Scheme 16-1] above was used instead of [Intermediate 1-c] instead of [Intermediate 1-c] [Compound 16] (yield: 49%) was obtained in the same manner as in the synthesis of [Intermediate 5-a].

MS (MALDI-TOF): m / z 798.28 [M ^< ⁺ &^gt;].

[Synthesis Example 17] Synthesis of Compound 17

[Synthesis of Intermediate 17-a]

[Intermediate 17-a]

Intermediate 17-a was obtained by using 9H-carbazole-3-ylboronic acid instead of [Intermediate 1-e] used in above Reaction Scheme 1-6 and using iodobenzene instead of [Intermediate 1-c] ] (Yield: 84%).

Synthesis of [Reaction Scheme 17-2] [Intermediate 17-b]

[Intermediate 17-b]

[Intermediate 5-b] synthesized in the above Reaction Scheme 5-2 was used instead of the 2-bromo-9,9-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4, [Intermediate 17-b] (yield: 78%) was obtained in the same manner as in [Intermediate 17-a], which was synthesized in the above [Reaction Scheme 17-1], in place of phenylboronic acid.

Synthesis of [Formula 17-3] [Compound 17]

[Compound 17]

[Compound 17] (yield: 49%) was obtained in the same manner as in [Intermediate 17-b] synthesized in [Scheme 17-2] above, in place of [Intermediate 1-e] used in the above Reaction Scheme 1-6.

MS (MALDI-TOF): m / z 738.28 [M ^< ⁺ &^gt;].

[Synthesis Example 18] Synthesis of Compound 18

Synthesis of [Intermediate 18-a]

[Intermediate 18-a]

[Intermediate 3-d] synthesized in the above Reaction Scheme 3-4 was used instead of the 2-bromo-9,9-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4, [Intermediate 18-a] (yield: 82%) was obtained in the same manner as in the method using pentaduteolephenylboronic acid instead of phenylboronic acid.

Synthesis of [Reaction Scheme 18-2] [Intermediate 18-b]

[Intermediate 18-b]

[Intermediate 18-a] synthesized in [Reaction Scheme 18-1] above was used instead of [Intermediate 1-e] used in [Reaction Scheme 1-6] [Intermediate 18-b] (yield: 76%) was obtained in the same manner as in the synthesis of [Intermediate 7-b].

Synthesis of [Compound 18]

[Compound 18]

[Intermediate 1-c] was prepared in the same manner as in [Reaction Scheme 3-1], except that [Intermediate 1-c] synthesized in [Scheme 18-2] above was used instead of [Intermediate 1-e] [Compound 18] (yield: 52%) was obtained in the same manner as the synthesized intermediate [intermediate 3-a].

MS (MALDI-TOF): m / z 762.45 [M ^< ⁺ &^gt;].

[Synthesis Example 19] Synthesis of Compound 19

Synthesis of [Synthesis 19-1] [Intermediate 19-a]

[Intermediate 19-a]

Instead of 2-bromo-9,9-dimethyl-9H-fluorene used in the above Reaction Scheme 1-4, 2-bromonitrobenzene was used instead of 4-iodophenylboronic acid, ] [Intermediate 19-a] (yield: 78%) was obtained in the same manner as in [Intermediate 6-a]

Synthesis of [Reaction Scheme 19-2] [Intermediate 19-b]

[Intermediate 19-b]

[Intermediate 19-b] (yield 65%) was obtained in the same manner as [Intermediate 19-a] synthesized in the above [Intermediate 19-1] instead of [Intermediate 15-c] used in the above Reaction Scheme 15-4 .

Synthesis of [Reaction formula 19-3] [Compound 19]

[Compound 19]

[Compound 19] (yield: 48%) was obtained in the same manner as in [Intermediate 19-b] synthesized in the above Reaction Scheme 19-2 instead of Intermediate 1-e used in Reaction Scheme 1-6.

MS (MALDI-TOF): m / z 586.22 [M ^< ⁺ &^gt;].

[Synthesis Example 20] Synthesis of Compound 20

[Synthesis of Intermediate 20-a]

[Intermediate 20-a]

[Intermediate 20-a] was obtained in the same manner as in [Reaction Scheme 8-7] except that 2-bromoaniline was used in place of [Intermediate 8-f] and 4-iodobenzofuran was used instead of 2-bromoiodobenzene. (Yield: 47%).

Synthesis of [Reaction Scheme 20-2] [Intermediate 20-b]

[Intermediate 20-b]

[Intermediate 20-b] (yield 44%) was obtained in the same manner as in [Intermediate 20-a] synthesized in [Reaction Formula 20-1] instead of [Intermediate 8-g] used in the above Reaction Scheme 8-8 .

[Synthesis of Compound 20]

[Compound 20]

[Reaction Scheme 5-4] was used instead of [Intermediate 1-c], except that [Intermediate 20-b] synthesized in the above Reaction Scheme 20-2 was used in place of [Intermediate 1-e] [Compound 20] (yield: 53%) was obtained in the same manner as in [Intermediate 5-d] which was synthesized in the same manner.

MS (MALDI-TOF): m / z 589.22 [M ^< ⁺ &^gt;].

[Synthesis Example 21] Synthesis of Compound 21

[Synthesis of Intermediate 21-a]

[Intermediate 21-a]

[Intermediate 9-a] synthesized in the above Reaction Scheme 9-1 was used instead of [Intermediate 1-e] used in the above Reaction Scheme 1-6, and 3-iodopyridine was used instead of [Intermediate 1-c] [Intermediate 21-a] (yield: 76%) was obtained in the same manner.

Synthesis of [Reaction Scheme 21-2] [Intermediate 21-b]

[Intermediate 21-b]

2-chloroaniline was used in place of [Intermediate 8-f] used in the above Reaction Scheme 8-7, and [Intermediate 21-a] synthesized in the above Reaction Scheme 21-1 instead of 2-bromoiodobenzene was used [Intermediate 21-b] (yield: 60%) was obtained in the same manner.

[Synthesis of Intermediate 21-c]

[Intermediate 21-c]

[Intermediate 21-c] (yield: 47%) was obtained in the same manner as in [Intermediate 21-b] synthesized in the above Reaction Scheme 21-2 instead of Intermediate 8-g used in Reaction Scheme 8-8 .

Synthesis of [Formula 21-4] [Compound 21]

[Compound 21]

[Compound 21] (yield 47%) was obtained in the same manner as in [Intermediate 21-c] synthesized in the above Reaction Scheme 21-3 instead of Intermediate 1-e used in Reaction Scheme 1-6.

MS (MALDI-TOF): m / z 803.30 [M ^< ⁺ &^gt;

[Examples 1 to 21] Preparation of organic light emitting diode

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber, the substrate was pressurized to have a pressure of 1 × 10 ^-6 torr. Then, an organic material was injected onto the ITO using DNTPD (700 Å), α-NPB (300 Å) Alq ₃ (350 Å), LiF (5 Å), and Al (1,000 Å) were deposited in the order of + (piq) ₂ Ir (acac) (10%) (300 Å).

[DNTPD] [[alpha] -NPB]

_{[(piq) 2 Ir (acac} )] [Alq 3]

[Example 22]

Except that [Compound 14] was used for the light emitting layer in the device structures of Examples 1 to 21 and [PTOEP] was used in place of [(piq) ₂ Ir (acac)] in the organic light emitting diode device for Example 22 The structure of [PTOEP] is as follows.

[PTOEP]

[Comparative Example 1]

The organic light emitting diode device for Comparative Example 1 was fabricated in the same manner except that CBP, which is generally used as a phosphorescent host material, was used instead of the compound manufactured by the invention in the device structure of the embodiment, and the structure of the CBP is as follows .

[CBP]

[Comparative Examples 2 to 7]

The organic light emitting diode devices for Comparative Examples 2 to 7 were fabricated in the same way except that the following compounds [101] to [106] were used in place of the compounds prepared according to the invention in the device structures of Examples 1 to 21 The structure is as follows.

[Compound 101] [Compound 102] [Compound 103]

[Compound 104] [Compound 105] [Compound 106]

[Comparative Example 8]

The organic light emitting diode device for Comparative Example 8 was fabricated in the same manner except that [Compound 102] was used in place of [Compound 14] produced by the invention in the device structure of Example 22 above.

The voltage, the current density, the luminance, the color coordinate, and the lifetime of the organic electroluminescent device manufactured according to Examples 1 to 22 and Comparative Examples 1 to 8 were measured, and the results are shown in Table 1 below.

T ₉₀ means the time required for the luminance to decrease from the initial luminance (5000 nits) to 90%.

division Host Dopant Voltage (V) Brightness (Cd / m2) CIEx CIEy T ₉₀ Example 1 Compound 1 (piq) < / RTI > ₂ Ir (acac) 4 1500 0.673 0.323 1305 Example 2 Compound 2 (piq) < / RTI > ₂ Ir (acac) 3.9 1290 0.672 0.326 1120 Example 3 Compound 3 (piq) < / RTI > ₂ Ir (acac) 3.8 1980 0.669 0.323 1490 Example 4 Compound 4 (piq) < / RTI > ₂ Ir (acac) 3.8 1820 0.669 0.323 1513 Example 5 Compound 5 (piq) < / RTI > ₂ Ir (acac) 3.9 1830 0.672 0.327 1350 Example 6 Compound 6 (piq) < / RTI > ₂ Ir (acac) 3.8 1900 0.673 0.324 1695 Example 7 Compound 7 (piq) < / RTI > ₂ Ir (acac) 3.3 1790 0.674 0.326 1535 Example 8 Compound 8 (piq) < / RTI > ₂ Ir (acac) 3.2 1510 0.676 0.323 1277 Example 9 Compound 9 (piq) < / RTI > ₂ Ir (acac) 3.3 1320 0.672 0.324 1590 Example 10 Compound 10 (piq) < / RTI > ₂ Ir (acac) 3.8 1850 0.674 0.323 1430 Example 11 Compound 11 (piq) < / RTI > ₂ Ir (acac) 3.7 1990 0.673 0.328 1522 Example 12 Compound 12 (piq) < / RTI > ₂ Ir (acac) 3.8 1890 0.677 0.325 1536 Example 13 Compound 13 (piq) < / RTI > ₂ Ir (acac) 3.9 1850 0.675 0.324 1273 Example 14 Compound 14 (piq) < / RTI > ₂ Ir (acac) 3.8 1890 0.675 0.322 1713 Example 15 Compound 15 (piq) < / RTI > ₂ Ir (acac) 3.9 1850 0.674 0.324 1095 Example 16 Compound 16 (piq) < / RTI > ₂ Ir (acac) 3.5 1120 0.675 0.325 1244 Example 17 Compound 17 (piq) < / RTI > ₂ Ir (acac) 3.4 1080 0.676 0.329 1600 Example 18 Compound 18 (piq) < / RTI > ₂ Ir (acac) 3.4 1160 0.667 0.32 1680 Example 19 Compound 19 (piq) < / RTI > ₂ Ir (acac) 4 1860 0.671 0.329 1538 Example 20 Compound 20 (piq) < / RTI > ₂ Ir (acac) 4.1 1700 0.667 0.332 1310 Example 21 Compound 21 (piq) < / RTI > ₂ Ir (acac) 4.2 1850 0.675 0.325 1275 Example 22 Compound 14 PTOEP 3.8 1940 0.676 0.323 1438 Comparative Example 1 CBP (piq) < / RTI > ₂ Ir (acac) 7.9 350 0.667 0.324 125 Comparative Example 2 Compound 101 (piq) < / RTI > ₂ Ir (acac) 4.2 1310 0.676 0.326 312 Comparative Example 3 Compound 102 (piq) < / RTI > ₂ Ir (acac) 3.8 1830 0.674 0.325 1180 Comparative Example 4 Compound 103 (piq) < / RTI > ₂ Ir (acac) 3.9 1280 0.675 0.325 162 Comparative Example 5 Compound 104 (piq) < / RTI > ₂ Ir (acac) 4.3 1010 0.675 0.326 5 Comparative Example 6 Compound 105 (piq) < / RTI > ₂ Ir (acac) 4.2 1210 0.673 0.327 281 Comparative Example 7 Compound 106 (piq) < / RTI > ₂ Ir (acac) 4 1550 0.67 0.324 332 Comparative Example 8 Compound 102 PTOEP 4 1760 0.667 0.327 890

As shown in Table 1, the organic compound obtained according to the present invention has much lower driving voltage, higher luminous efficiency, and longer life than CBP among the host materials that are widely used as a phosphorescent host material.

Claims (8)

An organic light-emitting compound represented by the following Formula 1:
[Chemical Formula 1]

In the above formula (1)
A ₁ to A ₈ are the same or different and are each independently N or CR ₀ ,
B is selected from the following formulas (B1) to (B19)
[Formula B1] [Formula B2]

[Formula B3] [Formula B4]

(B5)

[Formula B6]

(B7)

(B8)

(B9)

(B10)

[B11]

(B12)

(B13)

(B14)

[B15]

(B16)

[Chemical formula B17]

[Formula B18]

[Chemical formula B19]

In the above formulas (1) and (B1) to (B19)
Z ₁ to Z ₄ are the same or different and each independently N or CR ₅ to CR ₈ ,
R and R ₀ to R ₁₇ are the same or different and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, A substituted or unsubstituted C2 to C60 heteroaryl group, a substituted or unsubstituted C3 to C60 cycloalkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C1 to C60 alkoxy group, Or an unsubstituted aryloxy group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms. A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms,
Cy is a substituted or unsubstituted cycloalkyl group having 3 to 8 carbon atoms,
Y is _{CR 18 R 19, NR 20,} O, S, SiR 21 R 22, GeR 23 R 24, PR 25, PR 26 (= O), C = O, BR 27,
X and X ₁ are each independently is a single bond _{CR 28 R 29, NR 30,} O, S, SiR 31 R 32, GeR 33 R 34, PR 35, PR 36 (= O), C = O, BR 37 , and ,
W ₁ to W ₄ are each independently CR ₃₈ to CR ₄₁ , and W ₁ to W ₄ Are bonded to Q ₁ to Q ₃ to form a fused ring,
L ₁ and L ₂ are each independently a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon group having 2 to 60 carbon atoms Substituted or unsubstituted C2-C60 alkynylene groups, substituted or unsubstituted C3-C60 alkynylene groups, substituted or unsubstituted C2- Substituted or unsubstituted C2-C60 heterocycloalkylene group, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 arylene group and substituted Or a substituted or unsubstituted C2-C60 heteroarylene group in which at least one unsubstituted C3-C30 cycloalkyl is fused,
Wherein R ₁₈ to R ₄₁ are the same as defined in R ₀ to R ₁₇ ,
m and m 'are integers of 1 to 2, n and n' are integers of 0 to 3, o is an integer of 0 to 3, and p is an integer of 1 to 3. The method according to claim 1,
The organic luminescent compound according to any one of the above [1] to [19] is any one selected from the following structural formula 1:
[Structural formula 1]

In the above formula 1,
R ₁ to R ₁₇ , X, X ₁ , Y, Z ₁ to Z ₄ , L ₂ , Cy, m, m ', n', p and W ₁ to W ₄ are the same as defined in the above , W ₁ to W ₄ Are adjacent to each other to form a fused ring by combining with Q ₁ to Q ₄ ,
remind

Is any one selected from the following C1 to C8,

C1 C2 C3 C4

C5 C6 C7 C8
In the above C1 to C8, - denotes a site bonded to a structural formula, and R 'is the same as the definition of R. The method according to claim 1,
Wherein R and R ₀ to R ₄₁ , Cy, X, X ₁ , Y, Z ₁ to Z ₄ and W ₁ to W ₄ , L ₁ and L ₂ are independently selected from the group consisting of hydrogen, deuterium, cyano, An alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 2 to 40 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, an arylamino group having 1 to 30 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, An aryl group having 6 to 40 carbon atoms, an aryloxy group having 6 to 40 carbon atoms, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 40 carbon atoms, and the substituent R ₀ To R ₄₁ , Cy, X, X ₁ , Y, Z ₁ to Z ₄ , W ₁ to W ₄ , L ₁ and L ₂ may be bonded to each other to form a saturated or unsaturated ring. A first electrode; A second electrode, and at least one organic layer interposed between the first electrode and the second electrode,
Wherein the organic layer comprises at least one organic electroluminescent compound represented by Formula 1 according to Claim 1. 5. The method of claim 4,
Wherein the organic layer comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer. 5. The method of claim 4,
Wherein the organic layer interposed between the first electrode and the second electrode comprises a light emitting layer. The method according to claim 6,
Wherein the light emitting layer comprises a host compound and a dopant compound, wherein the organic light emitting compound of Formula 1 is used as a host,
Wherein the light emitting layer further comprises at least one dopant compound. 8. The method of claim 7,
Wherein the organic layer further comprises one or more organic luminescent layers emitting red, green or blue light to emit white light.

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