KR20120122897A - New compounds and organic light-emitting diode including the same - Google Patents

Abstract

PURPOSE: A novel compound and an organic light emitting diode containing the same are provided to enhance driving voltage and current efficiency. CONSTITUTION: A novel compound is denoted by chemical formula 1. An organic light emitting diode comprises: an anode; a cathode; and a compound of chemical formula 1, which is inserted between the anode and cathode. The organic light emitting diode further comprises a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, or an electron injection layer between the anode and cathode. The layers are formed by a monomer deposition or a solution process.

Description

New compounds and organic light-emitting diodes including the same

The present invention relates to a novel compound and an organic light emitting device comprising the same as a light emitting material, and more particularly, a novel compound having excellent luminescent properties such as driving voltage and current efficiency and more stable and an organic light emitting diode comprising the same. It relates to an element.

Recently, as the size of the display device increases, the demand for a flat display device having a small space is increasing. A liquid crystal display, which is a typical flat display device, has a merit of being lighter than a conventional cathode ray tube (CRT). The disadvantage is that the angle is limited and the back light is necessary. In contrast, organic light emitting diodes (OLEDs), which are new flat panel display devices, are displays using self-luminous phenomena, and have a large viewing angle, are thinner and shorter than liquid crystal displays, and have fast response speeds. In recent years, the application to full-color display or lighting is expected.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.

An organic light emitting display device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. In this case, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. When it falls back to the ground, it glows. Such an organic electroluminescent device is known to have properties such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

The material used as the organic material layer in the organic electroluminescent device may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function. The light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. . In addition, the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.

On the other hand, when only one material is used as the light emitting material, the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect. A host-dopant system can be used as the luminescent material to increase the luminous efficiency through.

When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.

In order for the organic electroluminescent device to fully exhibit the above-mentioned excellent features, the organic layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. is supported by a stable and efficient material Although this should be preceded, the development of a stable and efficient organic material layer for an organic light emitting device has not been made yet. therefore

Accordingly, the first technical problem to be achieved by the present invention is to provide a novel compound having low driving voltage and excellent luminous efficiency.

The second technical problem to be achieved by the present invention is to provide an organic electroluminescent device comprising the novel compound.

The present invention provides a compound represented by the following [Formula 1] to achieve the first technical problem.

[Formula 1]

In [Formula 1], X is NR_One, O, S, CR_OneR₂, SiR_OneR₂ Or P, wherein R_OneAnd R₂, A and B are each independently the same or different from each other, and R_One, R₂, A and B are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 3 -C 30 cyclo Alkyl group, substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted carbon number 1 An alkylthioxy group of 30 to 30, a substituted or unsubstituted arylthioxy group of 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine group of 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group of 5 to 30 carbon atoms, substituted Or an unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, a substituted or unsubstituted silicon group, substituted or non- A ring boron group, a substituted or unsubstituted silane group, a carbonyl group, a phosphoryl group, an amino group, a nitrile group, a hydroxy group, a nitro group, a halogen group, an amide group and an ester group, selected from the group adjacent to each other, aliphatic, aromatic, Form a condensed ring of aliphatic or aromatic hetero or spiro bonds,

L is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 30 carbon atoms as a chemical bond or a divalent linking group. , A substituted or unsubstituted arylene group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms,

Ar is a substituted or unsubstituted substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom,

An is a substituted or unsubstituted anthracene.

According to an embodiment of the present invention, [Formula 1] may be any one selected from the group represented by the following [Formula 2] to [Formula 25].

[Formula 2] [Formula 3]

[Formula 4] [Formula 5]

[Chemical Formula 6] < EMI ID =

[Formula 8] [Formula 9]

[Formula 10] [Formula 11]

[Formula 12] [Formula 13]

[Formula 14] [Formula 15]

[Formula 16] [Formula 17]

[Formula 18] [Formula 19]

[Formula 20] [Formula 21]

[Formula 22] [Formula 23]

[Formula 24] [Formula 25]

In [Formula 2] to [Formula 25], R ₁ , R ₂ , A, B, L, Ar and An are the same as the definition in [Formula 1].

According to another aspect of the present invention,

Provided are an anode, a cathode, and an organic electroluminescent device interposed between the anode and the cathode and comprising a compound represented by the above [Formula 1].

According to the present invention, the novel compound represented by [Formula 1] has a stable and excellent light emission characteristics compared to the existing material, so that the organic light emitting device including the low voltage can be driven and improve the luminous efficiency.

1 is a schematic diagram of an organic light emitting display device according to an embodiment of the present invention.
2 to 3 are graphs showing lifespan characteristics of an organic light emitting display device according to an embodiment of the present invention and an organic light emitting display device according to a comparative example.

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

The present invention is a novel compound included in the light emitting layer of the organic field device, characterized in that the compound represented by the following [Formula 1], in the formula [1], the substituents are described in more detail as follows.

[Formula 1]

In [Formula 1], X is NR ₁ , O, S, CR ₁ R ₂ , SiR ₁ R ₂ Or P, wherein R ₁ and R ₂ , A and B are the same as or different from each other, and R ₁ , R ₂ , A and B are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted carbon number 1 to 30 alkyl groups, substituted or unsubstituted alkenyl groups having 2 to 30 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl groups having 5 to 30 carbon atoms, substituted or unsubstituted carbon atoms An alkoxy group having 1 to 30, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, substituted Or an unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted hetero atom, O, N Or have S Is a heteroaryl group having 3 to 50 carbon atoms, substituted or unsubstituted silicone group, substituted or unsubstituted boron group, substituted or unsubstituted silane group, carbonyl group, phosphoryl group, amino group, nitrile group, hydroxy group, nitro group, It is selected from the group consisting of a halogen group, an amide group and an ester group, and may form a condensed ring or form a spiro bond of an aliphatic, aromatic, aliphatic hetero or aromatic hetero group with adjacent groups, wherein L is a chemical bond or a divalent linking group. Substituted or unsubstituted C1-C30 alkylene group, substituted or unsubstituted C2-C30 alkenylene group, substituted or unsubstituted C3-C30 cycloalkylene group, substituted or unsubstituted C5-C50 Arylene group, a substituted or unsubstituted C3-C50 heteroarylene group selected from the group consisting of, Ar is substituted or unsubstituted A substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted aryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, and preferably, Ar is a substituted or unsubstituted phenyl group. An may be substituted or unsubstituted anthracene.

Specific examples of the alkyl group which is a substituent used in the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, heptyl, octyl, A stearyl group, a trichloromethyl group, a trifluoromethyl group, and the like, and at least one hydrogen atom of the alkyl group may be a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a trifluoromethyl group, or a silyl group (in this case, Alkylsilyl groups ", substituted or unsubstituted amino groups (-NH ₂ , -NH (R), -N (R ') (R''), wherein R, R' and R" are each independently carbon atoms An alkyl group of 1 to 24 (in this case referred to as an "alkylamino group"), an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group of 1 to 24 carbon atoms, a halogenated alkyl group of 1 to 24 carbon atoms , Alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, 1 carbon atom It may be substituted with a heteroalkyl group of 24 to 24, an aryl group of 5 to 24 carbon atoms, an arylalkyl group of 6 to 24 carbon atoms, a heteroaryl group of 3 to 24 carbon atoms or a heteroarylalkyl group of 3 to 24 carbon atoms.

Specific examples of the alkoxy group which is a substituent used in the compound of the present invention include methoxy group, ethoxy group, propoxy group, isobutyloxy group, sec-butyloxy group, pentyloxy group, iso-amyloxy group, hexyloxy group and the like. These can be mentioned and can substitute by the same substituent as the case of the said alkyl group.

Specific examples of the aryl group which is a substituent used in the compound of the present invention are phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, o-biphenyl group, m-biphenyl group, p-ratio Phenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, 2-naphthyl group, 1-methylnaphthyl group, 2-methylnaphthyl group And an aromatic group such as an anthryl group, a phenanthryl group, a pyrenyl group, a fluorenyl group, a tetrahydronaphthyl group, and the like, and may be substituted with the same substituent as in the alkyl group.

Specific examples of the heteroaryl group which is a substituent used in the compound of the present invention include pyridinyl group, pyrimidinyl group, triazinyl group, indolinyl group, quinolinyl group, pyrrolidinyl group, piperidinyl group, morpholidinyl group, pipepe Radiinyl, carbazolyl, oxazolyl, oxdiazolyl, benzooxazolyl, chiazolyl, thiadiazolyl, benzothiazolyl, triazolyl, imidazolyl and benzoimidazole At least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as in the alkyl group.

Specific examples of the alkenyl group, which is a substituent used in the compound of the present invention, include an alkenyl group in which an aryl group such as a stybenyl group and a styrenyl group are connected. It is not limited.

The arylamine group which is a substituent used in the compound of the present invention is a diphenylamine group, a phenylnaphthylamine group, a phenylbiphenylamine group, a naphthylbiphenylamine group, a dinaphthylamine group, a dibiphenylamine group, a dianthracenylamine Group, 3-methyl-phenylamine group, 4-methyl-naphthylamine group, 2-methyl-biphenylamine group, 9-methyl- anthracenylamine group, ditolyl amine group, phenyl tolyl amine group, triphenylamino A phenyl amine group, a phenyl biphenylamino phenyl amine group, a naphthyl phenylaminophenyl biphenylamine group, etc. are mentioned, but it is not limited to this.

In the present invention, the term "substituted or unsubstituted" is cyano, halogen, hydroxy, nitro, alkyl, alkoxy, alkylamino, arylamino, heteroarylamino, alkylsilyl, arylsilyl, aryl Substituted or unsubstituted with one or more substituents selected from the group consisting of oxy group, aryl group, heteroaryl group, germanium, phosphorus, boron, hydrogen and deuterium.

The organic light emitting compound of [Formula 1] according to the present invention may be more specifically any one of the compounds represented by the following [Formula 2] to [Formula 1241].

In addition, the present invention provides an organic electroluminescent device comprising an anode, a cathode and a novel compound represented between the anode and the cathode, and represented by the above [Formula 1].

In this case, the layer containing the novel compound is preferably a light emitting layer between the anode and the cathode, and between the anode and the cathode as a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer It may further comprise one or more layers selected from the group consisting of.

In addition, according to another embodiment of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 kPa, and the light emitting layer may further include various phosphorescent host materials.

As a specific example, a hole transport layer (HTL) may be further stacked, and an electron transport layer (ETL) may be additionally stacked between the cathode and the organic light emitting layer. The silver is stacked to facilitate the injection of holes from the anode, and the electron transport molecule having a small ionization potential is used as the material of the hole transport layer. A diamine, triamine or tetraamine derivative mainly based on triphenylamine is used. It is used a lot.

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 (a-NPD).

A hole injection layer (HIL) may be further stacked on the lower portion of the hole transport layer. The hole injection layer material may also be used without particular limitation as long as it is commonly used in the art. For example, CuPc (copperphthalocyanine) or starburst amines TCTA (4,4 ', 4' '-tri (N-carbazolyl) triphenyl-amine), m-MTDATA (4,4', 4 ''-tris- (3 -methylphenylphenyl amino) triphenylamine) may be used.

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 electron transport layer material may be used without particular limitation as long as it is commonly used in the art, and for example, oxadiazole derivatives such as PBD, BMD, BND or Alq ₃ may be used.

Meanwhile, an electron injection layer (EIL) may be further stacked on the electron transport layer to facilitate electron injection from the cathode and ultimately improve power efficiency. Also commonly used in the art may be used without particular limitation, for example, it may be used a material such as LiF, NaCl, CsF, Li ₂ O, BaO.

The organic light emitting display device according to the present invention can be used for a display device, a display device and a monochrome or white lighting device.

1 is a cross-sectional view showing the structure of an organic light emitting display device according to the present invention. The organic light emitting device according to the present invention includes an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60 and a cathode 80, and if necessary, the hole injection layer 30 and The electron injection layer 70 may be further included. In addition, an intermediate layer of one or two layers may be further formed, and a hole blocking layer or an electron blocking layer may be further formed.

Referring to Figure 1 with respect to the organic light emitting device and a method of manufacturing the present invention are as follows. First, the anode 20 is formed by coating an anode electrode material on the substrate 10. As the substrate 10, a substrate used in a conventional organic EL device is used. An organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness is preferable. 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.

The hole injection layer 30 is formed by vacuum-heat deposition or spin coating of the hole injection layer material on the anode 20 electrode. Next, the hole transport layer 40 is formed by vacuum thermal evaporation or spin coating of the hole transport layer material on the hole injection layer 30.

Subsequently, the organic light emitting layer 50 is stacked on the hole transport layer 40, and 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. can do. The hole blocking layer prevents such a problem by using a material having a very low highest Occupied Molecular Orbital (HOMO) level because when the hole is introduced into the cathode through the organic light emitting layer is reduced the lifetime and efficiency of the device. . In this case, the hole blocking material to be used is not particularly limited, but should have an ionization potential higher than the light emitting compound while having an electron transport ability, and typically BAlq, BCP, TPBI, and the like may be used.

After the electron transport layer 60 is deposited on the hole blocking layer through a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed and a cathode forming metal is vacuum-heated on the electron injection layer 70. The organic EL device is completed by vapor deposition to form a cathode 80 electrode. The metal for forming the cathode may be lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lidium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag), and the like, and a transmissive cathode using ITO and IZO can be used to obtain a front light emitting device.

According to another embodiment of the present invention, at least one layer selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer is a single molecule deposition method or a solution process The organic light emitting display device according to the present invention may be used in display devices, display devices, and monochrome or white lighting devices.

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.

<Examples>

Synthesis Example 1 Synthesis of Compound Represented by Formula 26

(1) Synthesis of Compound Represented by [Formula 1-a]

A compound represented by the formula (1-a) was synthesized by the following reaction scheme (1).

[Reaction Scheme 1]

[Chemical Formula 1-a]

In a 1 L three-necked round flask, 50 g (152 mmol) of 1-bromo-2-iodo-4-nitrobenzene, 1.45 g (7.6 mmol) of copper iodide, 3.5 g of Pd (PPh ₃ ) ₄ mmol) and dissolve in 200 ml of triethylamine. After dissolving all the reactants, 21.8 g (198 mmol) of phenylacetylene under nitrogen was slowly added to a dropping funnel and stirred at room temperature for 4 hours. After the reaction was completed, 500 ml of normal hexane was diluted, and the reaction solution was filtered through a Buchner vacuum funnel filled with 200 g of silica gel to remove the catalyst and salt, followed by washing with 1 L of normal hexane. Removal of all solvents in the filtered solution yields yellow oil. (40 g, yield 86%)

(2) Synthesis of Compound Represented by Formula (1-b)

[Chemical Formula 1-b] was synthesized by the following Reaction Scheme 2.

Scheme 2

[Formula 1-a] [Formula 1-b]

40 g (132 mmol) of the compound represented by [Formula 1-a] obtained from the above [Scheme 1], 40.3 g (159 mmol) of Bis (pinacolate) diboron, and Pd (dppf) ₂ Cl ₂ ? H ₂ Cl ₂ 4.3 g (5 mmol) and 27.8 g (331 mmol) of KOAc were added to a 1 L three-necked round flask and dissolved in 400 ml of toluene and refluxed at 110 ° C for 12 hours. At the end of the reaction, the salt is removed with a hot filter, the filtrate is extracted with dimethyl chloride and water and purified by column. (38 g, yield 82%)

(3) Synthesis of Compound Represented by Formula (1-c)

The compound represented by the formula (1-c) was synthesized by the following reaction scheme [3].

Scheme 3

[Chemical Formula 1-b] [Chemical Formula 1-c]

50 g (143 mmol) of the compound represented by 30 g (110 mmol) of 2-bromo-9,9dimethylfluorene and [Formula 1-b] obtained from the above [Scheme 2] in a 1 L three-necked round flask; Pd (dppf) ₂ Cl _2? 5.3 g (7 mmol) of H ₂ Cl _{2 and a} saturated solution of NaHCO ₃ (27.7 g, 329 mmol) were added thereto, dissolved in 500 ml of tetrahydrofuran and refluxed at 80 ° C. for 12 hours. After the reaction, the temperature was lowered to room temperature, cooled, extracted with dimethyl chloride and water, and purified by column. (35 g, yield 76%)

(4) Synthesis of a compound represented by the formula (1-d)

[Chemical Formula 1-d] was synthesized by the following Reaction Scheme 4.

[Reaction Scheme 4]

[Formula 1-c] [Formula 1-d]

Into a 500 mL three-necked round flask, 35 g (84 mmol) of the compound represented by [Formula 1-c] obtained from [Scheme 3] were dissolved in 300 ml of diethyl chloride, and Fe (OTf) ₃ 6.3 g (13 mmol) was added. The mixture was refluxed at 80 ° C. for 3 hours. After the reaction, the temperature was lowered to room temperature and the reaction solution was filtered through a Buchner vacuum funnel filled with silica gel / celite to remove the catalyst, and then cooled and purified by a column. (31 g, yield 88%)

(5) Synthesis of Compound Represented by Formula (1-e)

[Chemical Formula 1-e] was synthesized by the following Reaction Scheme 5.

Scheme 5

[Formula 1-d] [Formula 1-e]

30 g (72 mmol) of the compound represented by [Formula 1-d] obtained from [Scheme 4] were added to a 2 L four-necked round flask, and 600 ml of ethanol and 200 ml of 12N hydrochloric acid were added and stirred. Add 12.8 g (110 mmol) of Tin powder in small portions, paying attention to heat generation at 0 ℃. When all the tin is added, the mixture is heated to 100 ° C. using a heating mantle and stirred for 5 hours. After completion of the reaction, pay attention to exotherm at 0 ° C and slowly add dropwise solution of about 12 N NaOH to adjust Ph9 or more. Extract with ethyl acetate and filter to remove tin remaining in the filtrate (put celite on filtration). Remove all filtrate and recrystallize from normal hexane to obtain apricot solid. (20 g, 72% yield)

(6) Synthesis of Compound Represented by Formula 1-f

The compound represented by [Formula 1-f] by the following [Scheme 6] was synthesized.

[Reaction Scheme 6]

[Formula 1-e] [Formula 1-f]

21 g (54 mmol) of the compound represented by [Formula 1-e] obtained from [Scheme 5] were added to a 2 L four-necked round flask, 600 ml of acetonitrile, 9.4 g (140 mmol) of NaNO ₃ , and 22.6 g of KI. Add (140 mmol) and stir. Slowly add 80 ml of 12N HCl. Stir at room temperature for 12 hours, and after completion of the reaction, add 500 ml of water and stir for 30 minutes. Extract with dimethylchloride and water and purify by column. (18 g, yield 66%)

(7) Synthesis of Compound Represented by Formula 26

The compound represented by [Formula 26] was synthesized by the following [Scheme 7].

[Reaction Scheme 7]

[Formula 1-f] [Formula 26]

8 g (16 mmol) of the compound represented by [Formula 1-f] obtained from the above [Scheme 6], 5.7 g (19 mmol) of phenylanthraceneboronic acid, 0.4 g (1 mmol) of Kd (PPh ₃ ) ₄ , and K ₂ 4.5 g (32 mmol) of CO ₃ were added to a 500 ml round flask, and dissolved in toluene, ethanol and water (180/30/50 ml), and refluxed at 85 ° C. for 12 hours. The reaction was terminated by lowering the temperature to room temperature, and the resulting solid was filtered, washed with n-nucleic acid, dissolved in tetrahydrofuran and purified by recrystallization three or four times. (7 g, yield 70%)

Synthesis Example 2 Synthesis of Compound Represented by Chemical Formula 70

(1) Synthesis of Compound Represented by [Formula 2-a]

The compound represented by [Formula 2-a] was synthesized by the following [Scheme 8].

[Reaction Scheme 8]

[Formula 1-b] [Formula 2-a]

35 g (98 mmol) of a compound represented by 30 g (76 mmol) of 2-bromo-9,9 diphenylfluorene and [Formula 1-b] obtained from the above [Scheme 2] in a 1 L three-necked round flask; 3.7 g (5 mmol) of Pd (dppf) ₂ Cl ₂ -H ₂ Cl _{2 and a} saturated solution of NaHCO ₃ (19 g, 227 mmol) were added thereto, dissolved in 500 ml of tetrahydrofuran and refluxed at 80 ° C. for 12 hours. After the reaction, the temperature was lowered to room temperature, cooled, extracted with dimethyl chloride and water, and purified by column. (32 g, yield 78%)

(2) Synthesis of Compound Represented by [Formula 2-b]

The compound represented by [Formula 2-b] was synthesized by the following [Scheme 9].

Scheme 9

[Formula 2-a] [Formula 2-b]

30 g (56 mmol) of the compound represented by [Formula 2-a] obtained from the above [Scheme 8] were added to a 500 mL three-necked round flask, and dissolved in 300 ml of diethyl chloride. 4.2 g (8 mmol) of Fe (OTf) _{3 was} obtained. The mixture was refluxed at 80 ° C. for 3 hours. After the reaction, the temperature was lowered to room temperature and the reaction solution was filtered through a Buchner vacuum funnel filled with silica gel / celite to remove the catalyst, and then cooled and purified by a column. (25 g, yield 83%)

(3) Synthesis of Compound Represented by [Formula 2-c]

The compound represented by [Formula 2-c] was synthesized by the following [Scheme 10].

[Reaction Scheme 10]

[Formula 2-b] [Formula 2-c]

25 g (46 mmol) of the compound represented by [Formula 2-b] obtained from [Scheme 9] were added to a 2 L four-necked round flask, and 400 ml of ethanol and 100 ml of 12N hydrochloric acid were added and stirred. Be careful not to generate heat at 0 ℃ and add 8.3 g (70 mmol) of tin powder. When all the tin is added, the mixture is heated to 100 ° C. using a heating mantle and stirred for 5 hours. After completion of the reaction, pay attention to the exotherm at 0 ° C and slowly add dropwise solution of about 12 N NaOH to Ph9 or more. Extract with ethyl acetate and filter to remove tin remaining in the filtrate. (Celite is placed on the filtrate.) Remove all the filtrate and recrystallize from normal hexane to obtain apricot solid. (20 g, yield 84%)

(4) Synthesis of Compound Represented by [Formula 2-d]

The compound represented by [Formula 2-d] was synthesized by the following [Scheme 11].

[Reaction Scheme 11]

[Formula 2-c] [Formula 2-d]

20 g (39 mmol) of the compound represented by [Formula 2-c] obtained from [Scheme 10] were added to a 2 L four-necked round flask, 400 ml of acetonitrile, 6.8 g (100 mmol) of NaNO ₃ , and 16.3 g of KI. Add (100 mmol) and stir. Slowly add 60 ml of 12N HCl. Stir at room temperature for 12 hours, and after completion of the reaction, add 500 ml of water and stir for 30 minutes. Extract with dimethylchloride and water and purify by column. (21 g, yield 86%)

(5) Synthesis of Compound Represented by Formula 70

The compound represented by [Formula 70] was synthesized by the following [Scheme 12].

[Reaction Scheme 12]

[Formula 2-d] [Formula 70]

8 g (13 mmol) of the compound represented by [Formula 2-d] obtained from [Scheme 11], 4.6 g (15 mmol) of phenylanthraceneboronic acid, 0.3 g (1 mmol), K _{2 of} Pd (PPh ₃ ) ₄ 3.5 g (26 mmol) of CO ₃ were added to a 500 ml round flask, and dissolved in toluene, ethanol, and water (180/30/50 ml), and refluxed at 85 ° C. for 12 hours. The reaction was terminated by lowering the temperature to room temperature, and the resulting solid was filtered, washed with n-nucleic acid, dissolved in tetrahydrofuran and purified by recrystallization three or four times. (6 g, yield 62%)

Synthesis Example 3 Synthesis of Compound Represented by Formula 114

(1) Synthesis of Compound Represented by [Formula 3-a]

The compound represented by [Formula 3-a] was synthesized by the following [Scheme 13].

[Reaction Scheme 13]

[Formula 3-a]

In a 1 L three-necked round flask, 50 g (138 mmol) of 1,3-dibromo-2-iodobenzene, 1.3 g (6.9 mmol) of copper iodide, and 3.2 g (2.8 mmol) of Pd (PPh ₃ ) ₄ were added. Add and dissolve in 200 ml of triethylamine. After dissolving all the reactants, 17.5 g (171 mmol) of phenylacetylene was slowly added to a dropping funnel under nitrogen, followed by stirring at room temperature for 4 hours. After the reaction was completed, 500 ml of normal hexane was diluted, and the reaction solution was filtered through a Buchner vacuum funnel filled with 200 g of silica gel to remove the catalyst and salt, followed by washing with 1 L of normal hexane. Removal of all solvents in the filtered solution yields yellow oil. (40 g, yield 86%)

(2) Synthesis of Compound Represented by [Formula 3-b]

The compound represented by [Formula 3-b] was synthesized by the following [Scheme 14].

[Reaction Scheme 14]

[Formula 3-a] [Formula 3-b]

40 g (119 mmol) of the compound represented by [Formula 3-a] obtained from the above [Scheme 13], 36.3 g (143 mmol) of Bis (pinacolate) diboron, and Pd (dppf) ₂ Cl ₂ ˜H ₂ Cl ₂ 3.9 g (5 mmol) and 25.1 g (298 mmol) of KOAc were added to a 1 L three-necked round flask and dissolved in 400 ml of toluene and refluxed at 110 ° C for 12 hours. At the end of the reaction, the salt is removed with a hot filter, the filtrate is extracted with dimethyl chloride and water and purified by column. (25 g, yield 54%)

(3) Synthesis of Compound Represented by [Formula 3-c]

The compound represented by [Formula 3-c] was synthesized by the following [Scheme 15].

[Reaction Scheme 15]

[Formula 3-b] [Formula 3-c]

47 g (122 mmol) of the compound represented by 30 g (94 mmol) of 2-iodo-9,9 dimethylfluorene and [Formula 3-b] obtained from the above [Scheme 14] in a 1 L three-neck round flask; 4.6 g (6 mmol) of Pd (dppf) ₂ Cl ₂ -H ₂ Cl _{2 and a} saturated solution of NaHCO ₃ (23.6 g, 281 mmol) were added thereto, dissolved in 500 ml of tetrahydrofuran and refluxed at 80 ° C for 12 hours. After the reaction, the temperature was lowered to room temperature, cooled, extracted with dimethyl chloride and water, and purified by column. (24 g, yield 57%)

(4) Synthesis of Compound Represented by [Formula 3-d]

The compound represented by [Formula 3-d] was synthesized according to Reaction Scheme 16 below.

[Reaction Scheme 16]

[Formula 3-c] [Formula 3-d]

Into a 500 mL three-necked round flask, 24 g (53 mmol) of the compound represented by [Chemical Formula 3-c] obtained from [Scheme 15] were dissolved in 200 ml of diethyl chloride, and Fe (OTf) ₃ 4.0 g (8 mmol) was added. The mixture was refluxed at 80 ° C. for 3 hours. After the reaction, the temperature was lowered to room temperature and the reaction solution was filtered through a Buchner vacuum funnel filled with silica gel / celite to remove the catalyst, and then cooled and purified by a column. (20 g, yield 83%)

(5) Synthesis of Compound Represented by Formula 114

The compound represented by [Formula 114] was synthesized by the following [Scheme 17].

[Reaction Scheme 17]

[Formula 3-d] [Formula 114]

7 g (16 mmol) of the compound represented by [Formula 3-d] obtained from [Scheme 16], 5.6 g (19 mmol) of phenylanthraceneboronic acid, 0.4 g (1 mmol) of Kd (PPh ₃ ) ₄ , and K ₂ 4.3 g (31 mmol) of CO ₃ were added to a 500 ml round flask, and dissolved in toluene, ethanol and water (180/30/50 ml), and refluxed at 85 ° C. for 12 hours. The reaction was terminated by lowering the temperature to room temperature, and the resulting solid was filtered, washed with n-nucleic acid, dissolved in tetrahydrofuran and purified by recrystallization three or four times. (6 g, yield 62%)

Synthesis Example 4 Synthesis of Compound Represented by Formula 115

(1) Synthesis of Compound Represented by Formula 115

The compound represented by [Formula 115] was synthesized by the following [Scheme 18].

[Reaction Scheme 18]

[Formula 3-d] [Formula 115]

7 g (16 mmol) of the compound represented by [Formula 3-d] obtained from [Scheme 16], phenylanthracenephenylboronic acid 7.0 g (19 mmol), Pd (PPh ₃ ) ₄ 0.4 g (1 mmol), K 4.3 g (31 mmol) of ₂ CO ₃ are added to a 500 ml round flask, and dissolved in toluene, ethanol and water (180/30/50 ml), and refluxed at 85 ° C. for 12 hours. The reaction was terminated by lowering the temperature to room temperature, and the resulting solid was filtered, washed with n-nucleic acid, dissolved in tetrahydrofuran and purified by recrystallization three or four times. (7.2 g, yield 66%)

Synthesis Example 5 Synthesis of Compound Represented by Chemical Formula 162

(1) Synthesis of Compound Represented by [Formula 2-a]

The compound represented by [Formula 5-a] was synthesized according to Reaction Scheme 19 below.

Scheme 19

[Formula 5-a]

Into a 5-liter four-necked round flask, add 250 g (884 mmol) of 1-bromo-2-iodobenzene, 8.4 g (44.2 mmol) of copper iodide, and 20.4 g (18 mmol) of Pd (PPh ₃ ) ₄ Dissolve in 1000 ml of ethylamine. After dissolving all the reactants, 116.4 g (1060 mmol) of phenylacetylene was slowly added to a dropping funnel under nitrogen and stirred at room temperature for 4 hours. After the reaction, 2000 ml of normal hexane was added to the mixture, and the reaction solution was filtered through a Buchner vacuum funnel filled with 1.5-2 kg of silica gel to remove the catalyst and salt, followed by washing with 5 L of normal hexane. Removal of all solvents in the filtered solution yields yellow oil. (225 g, yield 99%)

(2) Synthesis of Compound Represented by Formula 5-b

The compound represented by [Formula 5-b] was synthesized by the following [Scheme 20].

[Reaction Scheme 20]

[Formula 5-a] [Formula 5-b]

100 g (389 mmol) of the compound represented by [Formula 5-a] obtained from [Scheme 19] and Bis (pinacolate) diboron 128.4 g (506 mmol) and Pd (dppf) ₂ Cl ₂ ? H ₂ Cl ₂ 15.9 g (20 mmol) and 95.3 g (970 mmol) of KOAc were added to a 2 L four-necked round flask and dissolved in 1000 ml of toluene and refluxed at 110 ° C for 12 hours. At the end of the reaction, the salt is removed with a hot filter, the filtrate is extracted with dimethyl chloride and water and purified by column. (60 g, yield 50%)

(3) Synthesis of Compound Represented by [Formula 5-c]

The compound represented by [Formula 5-c] was synthesized by the following [Scheme 21].

Scheme 21

[Formula 5-b] [Formula 5-c]

43 g (143 mmol) of the compound represented by 30 g (110 mmol) of 2-bromo-9,9dimethylfluorene and [Formula 5-b] obtained from the above Reaction Scheme 20 in a 1 L three-necked round flask; 5.3 g (7 mmol) of Pd (dppf) ₂ Cl ₂ -H ₂ Cl _{2 and a} saturated NaHCO ₃ solution (27.7 g, 329 mmol) were added thereto, dissolved in 500 ml of tetrahydrofuran and refluxed at 80 ° C for 12 hours. After the reaction, the temperature was lowered to room temperature, cooled, extracted with dimethyl chloride and water, and purified by column. (33 g, yield 81%)

(4) Synthesis of Compound Represented by [Formula 5-d]

The compound represented by [Formula 5-d] was synthesized by the following [Scheme 22].

[Reaction Scheme 22]

[Formula 5-c] [Formula 5-d]

In a 1 L three-necked round flask, 30 g (81 mmol) of the compound represented by [Formula 5-c] obtained from [Scheme 21] were dissolved in 400 ml of dimethyl chloride and cooled to -78 ° C. Under nitrogen, 1.0 M solution of monoiodochloride (97 ml) was slowly added into a dropping funnel and stirred at room temperature for 4 hours. The reaction was terminated by adding saturated NaHSO3 solution, extracted with dimethyl chloride and water and purified by column. (34 g, yield 84%)

(5) Synthesis of Compound Represented by Formula 162

The compound represented by [Formula 162] was synthesized by the following [Scheme 23].

[Reaction Scheme 23]

[Formula 5-d] [Formula 162]

7.5 g (15 mmol) of the compound represented by [Formula 5-d] obtained from [Scheme 22], 6.8 g (18 mmol) of phenylanthracenephenylboronic acid, 0.35 g (1 mmol), K of Pd (PPh ₃ ) ₄ 4.2 g (30 mmol) of ₂ CO ₃ are added to a 500 ml round flask, and dissolved in toluene, ethanol and water (180/30/50 ml), and refluxed at 85 ° C. for 12 hours. The reaction was terminated by lowering the temperature to room temperature, and the resulting solid was filtered, washed with n-nucleic acid, dissolved in tetrahydrofuran and purified by recrystallization three or four times. (7.0 g, yield 66%)

Synthesis Example 6 Synthesis of Compound Represented by Chemical Formula 165

(1) Synthesis of Compound Represented by Formula 165

The compound represented by [Formula 165] was synthesized by the following [Scheme 24].

Scheme 24

[Formula 5-d] [Formula 165]

7.5 g (15 mmol) of the compound represented by [Formula 5-d] obtained from [Scheme 22], 7.7 g (18 mmol) of phenylanthracenenaphthylboronic acid, 0.35 g (1 mmol) of Pd (PPh ₃ ) ₄ , 4.2 g (30 mmol) of K ₂ CO ₃ were added to a 500 ml round flask, and dissolved in toluene, ethanol and water (180/30/50 ml), and refluxed at 85 ° C. for 12 hours. The reaction was terminated by lowering the temperature to room temperature, and the resulting solid was filtered, washed with n-nucleic acid, dissolved in tetrahydrofuran and purified by recrystallization three or four times. (8 g, yield 70%)

Synthesis Example 7 Synthesis of Compound Represented by Formula 174

(1) Synthesis of Compound Represented by [Formula 7-a]

The compound represented by [Formula 7-a] was synthesized by the following [Scheme 25].

[Reaction Scheme 25]

[Formula 7-a]

Into a 1 L four-necked round flask, 44 g (156 mmol) of 1-bromo-2-iodobenzene, 1.5 g (7.8 mmol) of copper iodide, and 3.6 g (3.1 mmol) of Pd (PPh ₃ ) ₄ were added. Dissolve in 300 ml of ethylamine. After dissolving all the reactants, 25.1 g (193 mmol) of 3,5-dimethylphenylacetylene was slowly added to a dropping funnel under nitrogen, followed by stirring at room temperature for 4 hours. After the reaction was completed, 400 ml of normal hexane was diluted, and the reaction solution was filtered through a Buchner vacuum funnel filled with 500 g of silica gel to remove the catalyst and salt, followed by washing with 5 L of normal hexane. Removal of all solvents in the filtered solution yields yellow oil. (40 g, 90% yield)

(2) Synthesis of Compound Represented by [Formula 7-b]

The compound represented by [Formula 7-b] was synthesized by the following [Scheme 26].

[Reaction Scheme 26]

[Formula 7-a] [Formula 7-b]

40 g (140 mmol) of the compound represented by [Formula 7-a] obtained from [Scheme 25], 42.7 g (168 mmol) of Bis (pinacolate) diboron, and Pd (dppf) ₂ Cl ₂ ? H ₂ Cl ₂ 4.58 g (6 mmol) and 29.5 g (750 mmol) of KOAc were added to a 1 L four-necked round flask and dissolved in 500 ml of toluene and refluxed at 110 ° C for 12 hours. At the end of the reaction, the salt is removed with a hot filter, the filtrate is extracted with dimethyl chloride and water and purified by column. (35 g, yield 75%)

(3) Synthesis of Compound Represented by [Formula 7-c]

The compound represented by [Formula 7-c] was synthesized by the following [Scheme 27].

[Reaction Scheme 27]

Formula 7-b Formula 7-c

31.6 g (95 mmol) of the compound represented by 20 g (73 mmol) of 2-bromo-9,9dimethylfluorene and [Formula 7-b] obtained from the above Scheme 26 in a 1 L three-neck round flask; 3.6 g (4 mmol) of Pd (dppf) ₂ Cl ₂ -H ₂ Cl _{2 and a} saturated NaHCO ₃ solution (18.5 g, 220 mmol) were added thereto, dissolved in 350 ml of tetrahydrofuran and refluxed at 80 ° C for 12 hours. After the reaction, the temperature was lowered to room temperature, cooled, extracted with dimethyl chloride and water, and purified by column. (24 g, yield 82%)

(4) Synthesis of Compound Represented by [Formula 7-d]

The compound represented by [Formula 7-d] was synthesized by the following Reaction Scheme 28.

[Reaction Scheme 28]

[Formula 7-c] [Formula 7-d]

In a 1 L three-necked round flask, 20 g (50 mmol) of the compound represented by [Formula 7-c] obtained from [Scheme 27] were dissolved in 300 ml of dimethyl chloride and cooled to -78 ° C. Under nitrogen, monoiodochloride 1.0 M solution (60 ml) was slowly added into a dropping funnel and stirred at room temperature for 4 hours. The reaction is terminated by adding saturated NaHSO 3 solution, extracted with dimethyl chloride and water and purified by column. (21 g, yield 80%)

(5) Synthesis of Compound Represented by Formula 174

The compound represented by [Formula 174] was synthesized by the following [Scheme 29].

[Reaction Scheme 29]

[Formula 7-d] [Formula 174]

7.0 g (13 mmol) of the compound represented by [Formula 7-d] obtained from [Scheme 28], 6.0 g (16 mmol) of phenylanthracenephenylboronic acid, 0.31 g (1 mmol), K of Pd (PPh ₃ ) ₄ 3.7 g (27 mmol) of ₂ CO ₃ was added to a 500 ml round flask, and dissolved in toluene, ethanol and water (180/30/50 ml), and refluxed at 85 ° C. for 12 hours. The reaction was terminated by lowering the temperature to room temperature, and the resulting solid was filtered, washed with n-nucleic acid, dissolved in tetrahydrofuran and purified by recrystallization three or four times. (8.0 g, 61% yield)

Synthesis Example 8 Synthesis of Compound Represented by Formula 206

(1) Synthesis of Compound Represented by [Formula 8-a]

The compound represented by [Formula 8-a] was synthesized by the following [Scheme 30].

Scheme 30

[Formula 1-c] [Formula 8-a]

In a 500 mL three-necked round flask, 35 g (84 mmol) of the compound represented by [Formula 1-c] obtained from [Scheme 3] were dissolved in 400 ml of dimethyl chloride and cooled to -78 ° C. Under nitrogen, 1.0 M solution of monoiodochloride (101 ml) was slowly added into a dropping funnel and stirred at room temperature for 4 hours. The reaction is terminated by adding saturated NaHSO 3 solution, extracted with dimethyl chloride and water and purified by column. (40 g, yield 87%)

(2) Synthesis of Compound Represented by Formula (8-b)

The compound represented by [Formula 8-b] was synthesized by the following [Scheme 31].

Scheme 31

[Formula 8-a] [Formula 8-b]

40 g (74 mmol) of the compound represented by [Formula 8-a] obtained from [Scheme 30], 10.8 g (89 mmol) of phenylboronic acid, 1.7 g (1 mmol) of Pd (PPh ₃ ) ₄ , K ₂ CO ₃ 20.4 g (148 mmol) was added to a 1 L four-necked round flask and dissolved in toluene and ethanol water (360/60/100 ml) and refluxed at 85 ° C. for 12 hours. The reaction was terminated by lowering the temperature to room temperature, extracted with ethyl acetate and water and purified by column. (30 g, yield 82%)

(3) Synthesis of Compound Represented by Formula (8-c)

The compound represented by [Formula 8-c] was synthesized by the following [Scheme 32].

Scheme 32

[Formula 8-b] [Formula 8-c]

30 g (61 mmol) of the compound represented by [Formula 8-b] obtained from [Scheme 31] were added to a 2 L four-necked round flask, and 600 ml of ethanol and 200 ml of 12N hydrochloric acid were added and stirred. Add 10.9 g (90 mmol) of Tin powder. When all the tin is added, the mixture is heated to 100 ° C. using a heating mantle and stirred for 5 hours. After completion of the reaction, pay attention to the exotherm at 0 ° C and slowly add dropwise solution of about 12 N NaOH to Ph9 or more. Extract with ethyl acetate and filter to remove tin remaining in the filtrate (put celite on filtration). Remove all filtrate and recrystallize from normal hexane to obtain apricot solid. (23 g, yield 81%)

(4) Synthesis of Compound Represented by Formula 8-d

The compound represented by [Formula 8-d] was synthesized by the following Reaction Scheme 33.

Scheme 33

[Formula 8-c] [Formula 8-d]

2 L 4 necked round flask, and the above-mentioned Reaction Formula 32] [Chemical Formula 8-c] into the compound 20 g (43 mmol) shown in acetonitrile 500 ml and NaNO ₃ 7.4 g (110 mmol) obtained from, KI 18.0 g Add (110 mmol) and stir. Slowly add 70 ml of 12N HCl. Stir at room temperature for 12 hours, and after completion of the reaction, add 500 ml of water and stir for 30 minutes. Extract with dimethylchloride and water and purify by column. (16 g, yield 64%)

(5) Synthesis of Compound Represented by Formula 206

The compound represented by [Formula 206] was synthesized according to Reaction Scheme 34 below.

Scheme 34

[Formula 8-d] [Formula 206]

8 g (14 mmol) of the compound represented by [Formula 8-d] obtained from [Scheme 33], 5.0 g (179 mmol) of phenylanthraceneboronic acid, 0.3 g (1 mmol) of Kd (PPh ₃ ) ₄ , and K ₂ 3.9 g (28 mmol) of CO ₃ were added to a 500 ml round flask, and dissolved in toluene, ethanol and water (180/30/50 ml), and refluxed at 85 ° C. for 12 hours. The reaction was terminated by lowering the temperature to room temperature, and the resulting solid was filtered, washed with n-nucleic acid, dissolved in tetrahydrofuran and purified by recrystallization three or four times. (7 g, 72% yield)

Synthesis Example 9 Synthesis of Compound Represented by Chemical Formula 218

(1) Synthesis of Compound Represented by Formula 218

The compound represented by [Formula 218] was synthesized by the following [Scheme 35].

Scheme 35

[Formula 9-a] [Formula 218]

8.0 g (13 mmol) of the compound represented by Formula 9-a, 4.6 g (15 mmol) of phenylanthraceneboronic acid, 0.30 g (1 mmol) of Pd (PPh ₃ ) ₄ , 3.6 g (26 mmol) of K ₂ CO ₃ ) Was dissolved in toluene, ethanol and water (180/30/50 ml) and refluxed at 85 ° C. for 12 hours. The reaction was terminated by lowering the temperature to room temperature, and the resulting solid was filtered, washed with n-nucleic acid, dissolved in tetrahydrofuran and purified by recrystallization three or four times. (6 g, yield 62%)

Synthesis Example 10 Synthesis of Compound Represented by Chemical Formula 709

(1) Synthesis of Compound Represented by Formula 709

The compound represented by [Formula 709] was synthesized by the following [Scheme 36].

Scheme 36

[Formula 10-a] [Formula 709]

7.0 g (13 mmol) of the compound represented by Formula 10-a, 5.8 g (15 mmol) of phenylanthracenephenylboronic acid, 0.30 g (1 mmol) of Pd (PPh ₃ ) ₄ , 3.5 g of K ₂ CO ₃ (26 mmol) was added to a 500 ml round flask and dissolved in toluene, ethanol and water (180/30/50 ml) and refluxed at 85 ° C. for 12 hours. The reaction was terminated by lowering the temperature to room temperature, and the resulting solid was filtered, washed with n-nucleic acid, dissolved in tetrahydrofuran and purified by recrystallization three or four times. (7.5 g, yield 78%)

Synthesis Example 11 Synthesis of Compound Represented by Chemical Formula 902

(1) Synthesis of Compound Represented by Formula 902

The compound represented by [Formula 902] was synthesized by the following [Scheme 37].

Scheme 37

[Formula 11-a] [Formula 902]

6.0 g (10 mmol) of the compound represented by Formula 11-a, 2.7 g (12 mmol) of phenylanthracenephenylboronic acid, 0.30 g (1 mmol) of Pd (PPh ₃ ) ₄ , 3.5 g of K ₂ CO ₃ (19 mmol) was added to a 500 ml round flask and dissolved in toluene, ethanol and water (180/30/50 ml) and refluxed at 85 ° C. for 12 hours. The reaction was terminated by lowering the temperature to room temperature, and the resulting solid was filtered, washed with n-nucleic acid, dissolved in tetrahydrofuran and purified by recrystallization three or four times. (5.0 g, yield 63%)

Synthesis Example 12 Synthesis of Compound Represented by Formula 934

(1) Synthesis of Compound Represented by Formula 934

The compound represented by [Formula 934] was synthesized by the following [Scheme 38].

Scheme 38

[Formula 12-a] [Formula 934]

5.0 g (8 mmol) of the compound represented by Formula 12-a, 2.7 g (9 mmol) of phenylanthraceneboronic acid, 0.18 g (1 mmol) of Pd (PPh ₃ ) ₄ , 2.1 g (16 mmol) of K ₂ CO ₃ ) Was dissolved in toluene, ethanol and water (180/30/50 ml) and refluxed at 85 ° C. for 12 hours. The reaction was terminated by lowering the temperature to room temperature, and the resulting solid was filtered, washed with n-nucleic acid, dissolved in tetrahydrofuran and purified by recrystallization three or four times. (3.8 g, yield 63%)

Synthesis Example 13 Synthesis of Compound Represented by Chemical Formula 959

(1) Synthesis of Compound Represented by Formula 959

The compound represented by [Formula 959] was synthesized by the following [Scheme 39].

Scheme 39

[Formula 13-a] [Formula 959]

5.0 g (8 mmol) of the compound represented by Formula 13-a, 3.5 g (9 mmol) of phenylanthracenephenylboronic acid, 0.18 g (1 mmol) of Pd (PPh ₃ ) ₄ , 2.1 g (16) of K ₂ CO ₃ mmol) was added to a 500 ml round flask and dissolved in toluene, ethanol and water (180/30/50 ml) and refluxed at 85 ° C. for 12 hours. The reaction was terminated by lowering the temperature to room temperature, and the resulting solid was filtered, washed with n-nucleic acid, dissolved in tetrahydrofuran and purified by recrystallization three or four times. (4.0 g, 61% yield)

Synthesis Example 14 Synthesis of Compound Represented by Chemical Formula 1079

(1) Synthesis of Compound Represented by Formula 1079

The compound represented by [Formula 1079] was synthesized by the following [Scheme 40].

Scheme 40

[Formula 14-a] [Formula 1079]

6.0 g (9 mmol) of the compound represented by Formula 14-a, 4.0 g (11 mmol) of phenylanthracenephenylboronic acid, 0.21 g (1 mmol) of Pd (PPh ₃ ) ₄ , 2.5 g of K ₂ CO ₃ (18 mmol) was added to a 500 ml round flask and dissolved in toluene, ethanol and water (180/30/50 ml) and refluxed at 85 ° C. for 12 hours. The reaction was terminated by lowering the temperature to room temperature, and the resulting solid was filtered, washed with n-nucleic acid, dissolved in tetrahydrofuran and purified by recrystallization three or four times. (5.0 g, yield 64%)

Synthesis Example 15 Synthesis of Compound Represented by Formula 1168

(1) Synthesis of Compound Represented by Formula 1168

The compound represented by [Formula 1168] was synthesized by the following [Scheme 41].

Scheme 41

[Formula 15-a] [Formula 1168]

7.0 g (10 mmol) of the compound represented by Formula 15-a, 4.4 g (12 mmol) of phenylanthracenephenylboronic acid, 0.23 g (1 mmol) of Pd (PPh ₃ ) ₄ , and 2.7 g of K ₂ CO ₃ (20) mmol) was added to a 500 ml round flask and dissolved in toluene, ethanol and water (180/30/50 ml) and refluxed at 85 ° C. for 12 hours. The reaction was terminated by lowering the temperature to room temperature, and the resulting solid was filtered, washed with n-nucleic acid, dissolved in tetrahydrofuran and purified by recrystallization three or four times. (5.3 g, yield 58%)

<Examples 1 to 15> Preparation of an organic light emitting display device including the compound synthesized in Synthesis Examples 1 to 15

The light emitting layer preferably comprises a pyrene-based compound of the following [formula] as a guest material.

[Chemical Formula]

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After mounting the ITO glass in the vacuum chamber and base pressure to 1 × 10 ^-7 torr, and then formed on the ITO in order of CuPc (800 kPa), α-NPD (300 kPa) 3% of the compound prepared by the present invention and the guest compound of the above formula were mixed to form a film (250 Å), followed by Alq ₃ (350 kV), LiF (5 kV), and Al (500 kV) in order to form an organic light emitting display device.

[CuPc]

[α-NPD]

[Alq ₃ ]

&Lt; Comparative Example 1 &

An organic electroluminescent device for a comparative example was manufactured in the same manner except for using an anthracene-based compound represented by the following [formula] instead of a compound prepared by the present invention as a host material in the device structure of the above embodiment.

[Chemical Formula]

Voltage Current density (㎃ / ㎠) Luminance (Cd / ㎡) CIEx CIEy T97 Example 1 3.77 10 869.4 0.13 0.10 32 Example 2 4.01 10 683.1 0.13 0.08 34 Example 3 3.99 10 620.5 0.14 0.09 30 Example 4 4.02 10 697.3 0.14 0.10 52 Example 5 4.04 10 327.0 0.13 0.09 4 Example 6 4.24 10 335.2 0.14 0.11 4 Example 7 4.11 10 507.3 0.13 0.09 37 Example 8 4.01 10 679.5 0.15 0.09 76 Example 9 4.08 10 655.1 0.14 0.10 2 Example 10 3.85 10 681.1 0.13 0.10 2 Example 11 3.77 10 807.2 0.13 0.10 33 Example 12 3.97 10 820.4 0.14 0.10 85 Example 13 3.89 10 869.7 0.14 0.11 92 Example 14 3.83 10 621.3 0.14 0.10 33 Example 15 3.95 10 690.1 0.13 0.13 20 Comparative Example 1 5.1 10 560 0.14 0.09 One

Voltage, current density, luminance, color coordinates, and lifespan of the organic light emitting diodes manufactured according to <Examples 1 to 15> and <Comparative Example 1> were measured, and the results are shown in [Table 1]. T97 means the time taken for the luminance to decrease to 97% of the initial luminance.

From the results of <Examples 1 to 15>, <Comparative Example 1> and [Table 1], the organic light emitting device including the compound represented by [Formula 1] according to the present invention has a low driving voltage, luminous efficiency Since it shows excellent characteristics, it can be seen that it can be usefully used for display devices, display devices, and lighting.

10: substrate 20: anode
30: hole injection layer 40: hole transport layer
50: organic light emitting layer 60: electron transport layer
70: electron injection layer 80: cathode

Claims (8)

A compound represented by the following [Formula 1]:
[Formula 1]

In [Formula 1],
X is NR ₁ , O, S, CR ₁ R ₂ , SiR ₁ R ₂ Or P,
R ₁ and R ₂ , A and B are the same as or different from each other, and R ₁ , R ₂ , A and B are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted carbon group having 1 to 30 carbon atoms Alkoxy group, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, substituted or unsubstituted An alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, substituted or unsubstituted and having O, N or S as a hetero atom Carbon number 3 Heteroaryl group, substituted or unsubstituted silicon group, substituted or unsubstituted boron group, substituted or unsubstituted silane group, carbonyl group, phosphoryl group, amino group, nitrile group, hydroxy group, nitro group, halogen group, It is selected from the group consisting of an amide group and an ester group, may form a condensed ring of the aliphatic, aromatic, aliphatic hetero or aromatic hetero group and adjacent groups with each other, or may form a spiro bond,
L is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 30 carbon atoms as a chemical bond or a divalent linking group. , A substituted or unsubstituted arylene group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms,
Ar is a substituted or unsubstituted substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom,
An is a substituted or unsubstituted anthracene. The method of claim 1,
[Formula 1] is a compound, characterized in that any one selected from the group represented by the following [Formula 2] to [Formula 25]:
[Formula 2] [Formula 3]

[Formula 4] [Formula 5]

[Formula 6] [Formula 7]

[Formula 8] [Formula 9]

[Formula 10] [Formula 11]

[Formula 12] [Formula 13]

[Formula 14] [Formula 15]

[Formula 16] [Formula 17]

[Formula 18] [Formula 19]

[Formula 20] [Formula 21]

[Formula 22] [Formula 23]

[Formula 24] [Formula 25]

In [Formula 2] to [Formula 25],
R ₁ , R ₂ , A, B, L, Ar, and An are the same as defined in [Formula 1]. The method of claim 1,
[Formula 1] is a compound, characterized in that any one selected from the compounds represented by the following [Formula 26] to [Formula 1241]:

[Chemical Formula 28] [Chemical Formula 28]

[Chemical Formula 32] [Chemical Formula 32]

[Chemical Formula 35] [Chemical Formula 35]

[Chemical Formula 40] [Chemical Formula 40] [Chemical Formula 40]

[Chemical Formula 43] [Chemical Formula 44] [Chemical Formula 45]

[Chemical Formula 48] [Chemical Formula 48] [Chemical Formula 48]

[Chemical Formula 51] [Chemical Formula 52] [Chemical Formula 53]

[Chemical Formula 55] [Chemical Formula 55] [Chemical Formula 55]

[Formula 58] [Formula 59] [Formula 60] [Formula 61]

[Chemical Formula 62] [Chemical Formula 65] [Chemical Formula 65]

[Chemical Formula 67] [Chemical Formula 68] [Chemical Formula 69]

[Formula 70] [Formula 71] [Formula 72] [Formula 73]

[Formula 74] [Formula 75] [Formula 76] [Formula 77]

[Formula 78] [Formula 79] [Formula 80] [Formula 81]

[Formula 82] [Formula 83] [Formula 84] [Formula 85]

[Formula 86] [Formula 87] [Formula 88] [Formula 89]

[Formula 90] [Formula 91] [Formula 92] [Formula 93]

[Chemical Formula 95] [Chemical Formula 96] [Chemical Formula 97]

[Chemical Formula 100] [Chemical Formula 100]

[Formula 103] [Formula 103]

[Chemical Formula 10] [Chemical Formula 10] [Chemical Formula 10] [Chemical Formula 10]

[Formula 110] [Formula 111] [Formula 112] [Formula 113]

[Formula 114] [Formula 115] [Formula 116] [Formula 117]

[Formula 118] [Formula 119] [Formula 120] [Formula 121]

[Formula 122] [Formula 123] [Formula 124] [Formula 125]

[Formula 126] [Formula 127] [Formula 128] [Formula 129]

[Formula 130] [Formula 131] [Formula 132] [Formula 133]

[Formula 134] [Formula 135] [Formula 136] [Formula 137]

[Formula 138] [Formula 139] [Formula 140] [Formula 141]

[Formula 142] [Formula 143] [Formula 144] [Formula 145]

[Formula 146] [Formula 147] [Formula 148] [Formula 149]

[Formula 150] [Formula 151] [Formula 152] [Formula 153]

[Formula 154] [Formula 155] [Formula 156] [Formula 157]

[Formula 158] [Formula 159] [Formula 160] [Formula 161]

[Formula 162] [Formula 163] [Formula 164] [Formula 165]

[Formula 166] [Formula 167] [Formula 168] [Formula 169]

[Formula 170] [Formula 171] [Formula 172] [Formula 173]

[Formula 174] [Formula 175] [Formula 176] [Formula 177]

[Formula 178] [Formula 179] [Formula 180] [Formula 181]

[Formula 182] [Formula 183] [Formula 184] [Formula 185]

[Formula 186] [Formula 187] [Formula 188] [Formula 189]

[Formula 190] [Formula 191] [Formula 192] [Formula 193]

[Formula 194] [Formula 195] [Formula 196] [Formula 197]

[Formula 198] [Formula 199] [Formula 200] [Formula 201]

[Formula 202] [Formula 203] [Formula 204] [Formula 205]
[Formula 206] [Formula 207] [Formula 208] [Formula 209]

[Formula 210] [Formula 211] [Formula 212] [Formula 213]

[Formula 214] [Formula 215] [Formula 216] [Formula 217]

[Formula 218] [Formula 219] [Formula 220] [Formula 221]

[Formula 222] [Formula 223] [Formula 224] [Formula 225]

[Formula 226] [Formula 227] [Formula 228] [Formula 229]

[Formula 230] [Formula 231] [Formula 232] [Formula 233]

[Formula 234] [Formula 235] [Formula 236] [Formula 237]

[Formula 238] [Formula 239] [Formula 240] [Formula 241]

[Formula 242] [Formula 243] [Formula 244] [Formula 245]

[Formula 246] [Formula 247] [Formula 248] [Formula 249]

[Formula 250] [Formula 251] [Formula 252] [Formula 253]

[Formula 25] [Formula 25] [Formula 25] [Formula 25]

[Formula 252] [Chemical Formula 260] [Chemical Formula 261]

[Formula 262] [Formula 264] [Formula 265]

[268] [268] [268] [269]

[273] [272] [272] [272]

(277) [Formula 277] [Formula 277]

(281) [Chemical Formula 280] [Chemical Formula 280]

[Formula 28] [Formula 28] [Formula 28]

[Formula 288] [Formula 288] [Formula 289]

[290] [290] [292] [293]

[Formula 294] [Formula 295] [Formula 296] [Formula 297]

[Formula 298] [Formula 299] [Formula 300] [Formula 301]

[Formula 302] [Formula 303] [Formula 304] [Formula 305]

[Formula 306] [Formula 307] [Formula 308] [Formula 309]

[Formula 310] [Formula 311] [Formula 312] [Formula 313]

[Formula 314] [Formula 315] [Formula 316] [Formula 317]

[Formula 318] [Formula 319] [Formula 320] [Formula 321]

[Formula 322] [Formula 323] [Formula 324] [Formula 325]

[Formula 326] [Formula 327] [Formula 328] [Formula 329]

[Formula 330] [Formula 331] [Formula 332] [Formula 333]

[Formula 334] [Formula 335] [Formula 336] [Formula 337]

[Formula 338] [Formula 339] [Formula 340] [Formula 341]

[Formula 342] [Formula 343] [Formula 344] [Formula 345]

[Formula 346] [Formula 347] [Formula 348] [Formula 349]

[Formula 350] [Formula 351] [Formula 352] [Formula 353]

[Formula 354] [Formula 355] [Formula 356] [Formula 357]

[Formula 358] [Formula 359] [Formula 360] [Formula 361]

[Formula 362] [Formula 363] [Formula 364] [Formula 365]

[Formula 366] [Formula 367] [Formula 368] [Formula 369]

[Formula 370] [Formula 371] [Formula 372] [Formula 373]

[Formula 374] [Formula 375] [Formula 376] [Formula 377]

[Formula 378] [Formula 379] [Formula 380] [Formula 381]

[Formula 382] [Formula 383] [Formula 384] [Formula 385]

[Formula 386] [Formula 387] [Formula 388] [Formula 389]

[Formula 390] [Formula 391] [Formula 392] [Formula 393]

[Formula 394] [Formula 395] [Formula 396] [Formula 397]

[Formula 398] [Formula 399] [Formula 400] [Formula 401]

[Formula 402] [Formula 403] [Formula 404] [Formula 405]

[Formula 406] [Formula 407] [Formula 408] [Formula 409]

[Formula 410] [Formula 411] [Formula 412] [Formula 413]

[Formula 414] [Formula 415] [Formula 416] [Formula 417]

[Formula 418] [Formula 419] [Formula 420] [Formula 421]

[Formula 422] [Formula 423] [Formula 424] [Formula 425]

[Formula 426] [Formula 427] [Formula 428] [Formula 429]

[Formula 430] [Formula 431] [Formula 432] [Formula 433]

[Formula 434] [Formula 435] [Formula 436] [Formula 437]

[Formula 438] [Formula 439] [Formula 440] [Formula 441]

[Formula 442] [Formula 443] [Formula 444] [Formula 445]

[Formula 446] [Formula 447] [Formula 448] [Formula 449]

[Formula 450] [Formula 451] [Formula 452] [Formula 453]

[Formula 454] [Formula 455] [Formula 456] [Formula 457]

[Formula 458] [Formula 459] [Formula 460] [Formula 461]

[Formula 462] [Formula 463] [Formula 464] [Formula 465]

[Formula 466] [Formula 467] [Formula 468] [Formula 469]

[Formula 470] [Formula 471] [Formula 472] [Formula 473]

[Formula 474] [Formula 475] [Formula 476] [Formula 477]

[Formula 478] [Formula 479] [Formula 480] [Formula 481]

[Formula 482] [Formula 483] [Formula 484] [Formula 485]

[Formula 486] [Formula 487] [Formula 488] [Formula 489]

[Formula 490] [Formula 491] [Formula 492] [Formula 493]

[Formula 494] [Formula 495] [Formula 496] [Formula 497]

[Formula 498] [Formula 499] [Formula 500] [Formula 501]

[Formula 502] [Formula 503] [Formula 504] [Formula 505]

[Formula 506] [Formula 507] [Formula 508] [Formula 509]

[Formula 510] [Formula 511] [Formula 512] [Formula 513]

[Formula 514] [Formula 515] [Formula 516] [Formula 517]

[Formula 518] [Formula 519] [Formula 520] [Formula 521]

[Formula 522] [Formula 523] [Formula 524] [Formula 525]

[Formula 526] [Formula 527] [Formula 528] [Formula 529]

[Formula 530] [Formula 531] [Formula 532] [Formula 533]

[Formula 534] [Formula 535] [Formula 536] [Formula 537]

[Formula 538] [Formula 539] [Formula 540] [Formula 541]

[Formula 542] [Formula 543] [Formula 544] [Formula 545]

[Formula 546] [Formula 547] [Formula 548] [Formula 549]

[Formula 550] [Formula 551] [Formula 552] [Formula 553]

[Formula 554] [Formula 555] [Formula 556] [Formula 557]

[Formula 558] [Formula 559] [Formula 560] [Formula 561]

[Formula 562] [Formula 563] [Formula 564] [Formula 565]

[Formula 566] [Formula 567] [Formula 568] [Formula 569]

[Formula 570] [Formula 571] [Formula 572] [Formula 573]

[Formula 574] [Formula 575] [Formula 576] [Formula 577]

[Formula 578] [Formula 579] [Formula 580] [Formula 581]

[Formula 582] [Formula 583] [Formula 584] [Formula 585]

[Formula 586] [Formula 587] [Formula 588] [Formula 589]

[Formula 590] [Formula 591] [Formula 592] [Formula 593]

[Formula 594] [Formula 595] [Formula 596] [Formula 597]

[Formula 598] [Formula 599] [Formula 600] [Formula 601]

[Formula 602] [Formula 603] [Formula 604] [Formula 605]

[Formula 606] [Formula 607] [Formula 608] [Formula 609]

[Formula 610] [Formula 611] [Formula 612] [Formula 613]

[Formula 614] [Formula 615] [Formula 616] [Formula 617]

[Formula 618] [Formula 619] [Formula 620] [Formula 621]

[Formula 622] [Formula 623] [Formula 624] [Formula 625]

[Formula 626] [Formula 627] [Formula 628] [Formula 629]

[Formula 630] [Formula 631] [Formula 632] [Formula 633]

[Formula 634] [Formula 635] [Formula 636] [Formula 637]

[Formula 638] [Formula 639] [Formula 640] [Formula 641]

[Formula 642] [Formula 643] [Formula 644] [Formula 645]

[Formula 646] [Formula 647] [Formula 648] [Formula 649]

[Formula 650] [Formula 651] [Formula 652] [Formula 653]

[Formula 654] [Formula 655] [Formula 656] [Formula 657]

[Formula 658] [Formula 659] [Formula 660] [Formula 661]

[Formula 662] [Formula 663] [Formula 664] [Formula 665]

[Chemical Formula 666] [Chemical Formula 667] [Chemical Formula 668]

[Formula 670] [Formula 671] [Formula 672] [Formula 673]

[Formula 674] [Formula 675] [Formula 676] [Formula 677]

[Formula 678] [Formula 679] [Formula 680] [Formula 681]

[Formula 682] [Formula 683] [Formula 684] [Formula 685]

[Formula 686] [Formula 687] [Formula 688] [Formula 689]

[Formula 690] [Formula 691] [Formula 692] [Formula 693]

[Formula 694] [Formula 695] [Formula 696] [Formula 697]

[Formula 698] [Formula 699] [Formula 700] [Formula 701]

[Formula 702] [Formula 703] [Formula 704] [Formula 705]

[Formula 706] [Formula 707] [Formula 708] [Formula 709]

[Formula 710] [Formula 711] [Formula 712] [Formula 713]

[Formula 714] [Formula 715] [Formula 716] [Formula 717]

[Formula 718] [Formula 719] [Formula 720] [Formula 721]

[Formula 722] [Formula 723] [Formula 724] [Formula 725]

[Formula 726] [Formula 727] [Formula 728] [Formula 729]

[Formula 730] [Formula 731] [Formula 732] [Formula 733]

[Formula 734] [Formula 735] [Formula 736] [Formula 737]

[Formula 738] [Formula 739] [Formula 740] [Formula 741]

[Formula 742] [Formula 743] [Formula 744] [Formula 745]

[Formula 746] [Formula 747] [Formula 748] [Formula 749]

[Formula 750] [Formula 751] [Formula 752] [Formula 753]

[Formula 754] [Formula 755] [Formula 756] [Formula 757]

[Formula 758] [Formula 759] [Formula 760] [Formula 761]

[Formula 762] [Formula 763] [Formula 764] [Formula 765]

[Formula 766] [Formula 767] [Formula 768] [Formula 769]

[Formula 770] [Formula 771] [Formula 772] [Formula 773]

[Chemical Formula 774] [Chemical Formula 775] [Chemical Formula 776]

[Formula 778] [Formula 779] [Formula 780] [Formula 781]

[Formula 782] [Formula 783] [Formula 784] [Formula 785]

[Formula 786] [Formula 787] [Formula 788] [Formula 789]

[Formula 790] [Formula 791] [Formula 792] [Formula 793]

[Formula 794] [Formula 795] [Formula 796] [Formula 797]

[Formula 798] [Formula 799] [Formula 800] [Formula 801]

[Formula 802] [Formula 803] [Formula 804] [Formula 805]

[Formula 806] [Formula 807] [Formula 808] [Formula 809]

[Formula 810] [Formula 811] [Formula 812] [Formula 813]

[Formula 814] [Formula 815] [Formula 816] [Formula 817]

[Formula 818] [Formula 819] [Formula 820] [Formula 821]

[Formula 822] [Formula 823] [Formula 824] [Formula 825]

[Formula 826] [Formula 827] [Formula 828] [Formula 829]

[Formula 830] [Formula 831] [Formula 832] [Formula 833]

[Formula 834] [Formula 835] [Formula 836] [Formula 837]

[Formula 838] [Formula 839] [Formula 840] [Formula 841]

[Formula 842] [Formula 843] [Formula 844] [Formula 845]

[Formula 846] [Formula 847] [Formula 848] [Formula 849]

[Formula 850] [Formula 851] [Formula 852] [Formula 853]

[Formula 854] [Formula 855] [Formula 856] [Formula 857]

[Formula 858] [Formula 859] [Formula 860] [Formula 861]

[Formula 862] [Formula 863] [Formula 864] [Formula 865]

[Formula 866] [Formula 867] [Formula 868] [Formula 869]

[Formula 870] [Formula 871] [Formula 872] [Formula 873]

[Formula 874] [Formula 875] [Formula 876] [Formula 877]

[Formula 878] [Formula 879] [Formula 880] [Formula 881]

[Formula 882] [Formula 883] [Formula 884] [Formula 885]

[Formula 886] [Formula 887] [Formula 888] [Formula 889]

[Formula 890] [Formula 891] [Formula 892] [Formula 893]

[Formula 894] [Formula 895] [Formula 896] [Formula 897]

[Formula 898] [Formula 899] [Formula 900] [Formula 901]

[Formula 902] [Formula 903] [Formula 904] [Formula 905]

[Formula 906] [Formula 907] [Formula 908] [Formula 909]

[Formula 910] [Formula 911] [Formula 912] [Formula 913]

[Formula 914] [Formula 915] [Formula 916] [Formula 917]

[Formula 918] [Formula 919] [Formula 920] [Formula 921]

[Formula 922] [Formula 923] [Formula 924] [Formula 925]

[Formula 926] [Formula 927] [Formula 928] [Formula 929]

[Formula 930] [Formula 931] [Formula 932] [Formula 933]

[Formula 934] [Formula 935] [Formula 936] [Formula 937]

[Formula 938] [Formula 939] [Formula 940] [Formula 941]

[Formula 942] [Formula 943] [Formula 944] [Formula 945]

[Formula 946] [Formula 947] [Formula 948] [Formula 949]

[Formula 950] [Formula 951] [Formula 952] [Formula 953]

[Formula 954] [Formula 955] [Formula 956] [Formula 957]

[Formula 958] [Formula 959] [Formula 960] [Formula 961]

[Formula 962] [Formula 963] [Formula 964] [Formula 965]

[Formula 966] [Formula 967] [Formula 968] [Formula 969]

[Formula 970] [Formula 971] [Formula 972] [Formula 973]

[Formula 974] [Formula 975] [Formula 976] [Formula 977]

[Formula 978] [Formula 979] [Formula 980] [Formula 981]

[Formula 982] [Formula 983] [Formula 984] [Formula 985]

[Formula 986] [Formula 987] [Formula 988] [Formula 989]

[Formula 990] [Formula 991] [Formula 992] [Formula 993]

[Formula 994] [Formula 995] [Formula 996] [Formula 997]

[Formula 998] [Formula 999] [Formula 1000] [Formula 1001]

[Formula 1002] [Formula 1003] [Formula 1004] [Formula 1005]

[Formula 1006] [Formula 1007] [Formula 1008] [Formula 1009]

[Formula 1010] [Formula 1011] [Formula 1012] [Formula 1013]

[Formula 1014] [Formula 1015] [Formula 1016] [Formula 1017]

[Formula 1018] [Formula 1019] [Formula 1020] [Formula 1021]

[Formula 1022] [Formula 1023] [Formula 1024] [Formula 1025]

[Formula 1026] [Formula 1027] [Formula 1028] [Formula 1029]

[Formula 1030] [Formula 1031] [Formula 1032] [Formula 1033]

[Formula 1034] [Formula 1035] [Formula 1036] [Formula 1037]

[Formula 1038] [Formula 1039] [Formula 1040] [Formula 1041]

[Formula 1042] [Formula 1043] [Formula 1044] [Formula 1045]

[Formula 1046] [Formula 1047] [Formula 1048] [Formula 1049]

[Formula 1050] [Formula 1051] [Formula 1052] [Formula 1053]

[Formula 1054] [Formula 1055] [Formula 1056] [Formula 1057]

[Formula 1058] [Formula 1059] [Formula 1060] [Formula 1061]

[Formula 1062] [Formula 1063] [Formula 1064] [Formula 1065]

[Formula 1066] [Formula 1067] [Formula 1068] [Formula 1069]

[Formula 1070] [Formula 1071] [Formula 1072] [Formula 1073]

[Formula 1074] [Formula 1075] [Formula 1076] [Formula 1077]

[Formula 1078] [Formula 1079] [Formula 1080] [Formula 1081]

[Formula 1082] [Formula 1083] [Formula 1084] [Formula 1085]

[Formula 1086] [Formula 1087] [Formula 1088] [Formula 1089]

[Formula 1090] [Formula 1091] [Formula 1092] [Formula 1093]

[Formula 1094] [Formula 1095] [Formula 1096] [Formula 1097]

[Formula 1098] [Formula 1099] [Formula 1100] [Formula 1101]

[Formula 1102] [Formula 1103] [Formula 1104] [Formula 1105]

[Formula 1106] [Formula 1107] [Formula 1108] [Formula 1109]

[Formula 1110] [Formula 1111] [Formula 1112] [Formula 1113]

[Formula 1114] [Formula 1115] [Formula 1116] [Formula 1117]

[Formula 1118] [Formula 1119] [Formula 1120] [Formula 1121]

[Formula 1122] [Formula 1123] [Formula 1124] [Formula 1125]

[Formula 1126] [Formula 1127] [Formula 1128] [Formula 1129]

[Formula 1130] [Formula 1131] [Formula 1132] [Formula 1133]

[Formula 1134] [Formula 1135] [Formula 1136] [Formula 1137]

[Formula 1138] [Formula 1139] [Formula 1140] [Formula 1141]

[Formula 1142] [Formula 1143] [Formula 1144] [Formula 1145]

[Formula 1146] [Formula 1147] [Formula 1148] [Formula 1149]

[Formula 1150] [Formula 1151] [Formula 1152] [Formula 1153]

[Formula 1154] [Formula 1155] [Formula 1156] [Formula 1157]

[Formula 1158] [Formula 1159] [Formula 1160] [Formula 1161]

[Formula 1162] [Formula 1163] [Formula 1164] [Formula 1165]

[Formula 1166] [Formula 1167] [Formula 1168] [Formula 1169]

[Formula 1170] [Formula 1171] [Formula 1172] [Formula 1173]

[Formula 1174] [Formula 1175] [Formula 1176] [Formula 1177]

[Formula 1178] [Formula 1179] [Formula 1180] [Formula 1181]

[Formula 1182] [Formula 1183] [Formula 1184] [Formula 1185]

[Formula 1186] [Formula 1187] [Formula 1188] [Formula 1189]

[Formula 1190] [Formula 1191] [Formula 1192] [Formula 1193]

[Formula 1194] [Formula 1195] [Formula 1196] [Formula 1197]

[Formula 1198] [Formula 1199] [Formula 1200] [Formula 1201]

[Formula 1202] [Formula 1203] [Formula 1204] [Formula 1205]

[Formula 1206] [Formula 1207] [Formula 1208] [Formula 1209]

[Formula 1210] [Formula 1211] [Formula 1212] [Formula 1213]

[Formula 1214] [Formula 1215] [Formula 1216] [Formula 1217]

[Formula 1218] [Formula 1219] [Formula 1220] [Formula 1221]

[Formula 1222] [Formula 1223] [Formula 1224] [Formula 1225]

[Formula 1226] [Formula 1227] [Formula 1228] [Formula 1229]

[Formula 1230] [Formula 1231] [Formula 1232] [Formula 1233]

[Formula 1234] [Formula 1235] [Formula 1236] [Formula 1237]

[Formula 1238] [Formula 1239] [Formula 1240] [Formula 1241] Anode;
Cathode; And
An organic electroluminescent device interposed between the anode and the cathode and comprising the compound of any one of claims 1 to 3. The method of claim 4, wherein
The compound is an organic light emitting device, characterized in that contained in the light emitting layer between the anode and the cathode. The method of claim 5, wherein
An organic electroluminescent device further comprising at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer between the anode and the cathode. The method according to claim 6,
At least one layer selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer is formed by a single molecule deposition method or a solution process. The method of claim 4, wherein
The organic electroluminescent device is an organic electroluminescent device, characterized in that used for a display device, a display device, or a device for monochrome or white illumination.

Images