TW201323379A - 1,1'-binaphthyl-4,4'-diamine derivatives for luminescence of organic electroluminescent device and organic electroluminescent device using them - Google Patents

Abstract

This invention relates to a 1, 1'-binaphthyl-4, 4'-diamine derivative represented by Chemical Formula 1 below for luminescence of an organic electroluminescent device, and to an organic electroluminescent device including the same. In Chemical Formula 1, Ar1 and Ar2, and R1 and R2 are independently the same as or different from each other, Ar1 and Ar2 are phenyl, naphthalene, anthracene, phenanthracene or pyrene, R1 is a substituted or unsubstituted C6 to C30 aryl or a substituted or unsubstituted C5 to C30 heteroaryl, R2 is phenyl, toluene, naphthalene, anthracene, phenanthracene, pyrene, or carbazole, and n and m are an integer ranging from 0 to 3.

Description

1,1'-binaphthyl-4,4'-diamine derivative for illuminating organic electroluminescence device and organic electroluminescent device using the same [Cross-Reference to Related Applications]

The present application claims the "1,1'-binaphthyl-4,4'-diamine derivative for use in the illumination of organic electroluminescent devices and the organic electroluminescent device using the same (November 10, 2011) 1,1 '-binaphthyl-4, 4'-diamine derivatives for luminescence of organic electroluminescent device and organic electroluminescent device using them), the application of which is based on the Korean Patent Application No. 10-2011-0116795 The manner of the full text is incorporated into the present application.

The present invention relates to a binaphthylamine derivative suitable for use in a light source of a display such as a mobile phone, a navigation system, a television set, and the like, and more particularly to 1,1'-binaphthyl-4 for illumination of an organic electroluminescent device. , 4'-diamine derivatives.

Typically, an organic light emitting device (OLED) is configured such that an organic layer is disposed between the cathode and the anode. The overall configuration of the device consists of a transparent anode including indium tin oxide (ITO), a hole injection layer (HIL), a hole transport layer (HTL), an emission layer (EL), and a hole blocking layer (HBL). ), an electron transport layer (ETL), an electron injection layer (EIL), and a cathode including LiAl. One or two layers may be omitted in the organic layer structure as needed. When an electric field is applied between the two electrodes, electrons are injected from the cathode and injected into the hole from the anode. In addition, these electrons recombine with the holes of the emissive layer to produce an excited state, and then emit energy in the form of light when the excited state returns to the ground state.

The luminescent material may be classified into a fluorescent material and a phosphorescent material, and the formation of the emissive layer includes a method of doping a fluorescent host (pure organic material) with a phosphorescent material (organic metal), and using a fluorescent dopant (including A nitrogen organic material or the like is doped with a fluorescent host, and a dopant (DCM, red fluorene, DCJTB or the like) is applied to the luminescent material to achieve a long wavelength or the like. Intensive research is currently underway on the use of doping to improve emission wavelength, efficiency, driving voltage, and lifetime.

The luminescent material comprises a symmetric/asymmetric body/dopant having high blue emission efficiency in the OLED.

Typically, the material used for the emissive layer has a structure comprising: a center such as benzene, naphthalene, anthracene, spiro, anthracene, anthracene, oxazole, etc.; a ligand such as phenyl, biphenyl, naphthalene, heterocyclic or An analog thereof; a bonding position of an ortho, meta and para; and a substituent such as an amine group, a cyano group, a fluorine group, a methyl group, a trimethyl group or the like.

As display screens are becoming larger and larger, OLEDs require materials that exhibit better color purity. Therefore, the target to be solved is a blue luminescent material, and a high-efficiency luminescent material is required from the current sky blue toward blue and dark blue. In addition to the color coordinates of the emission wavelength, it is also desirable to have high emission efficiency at low drive voltages and glass transition temperatures that increase the thermal stability of the chemical structure of the material.

The following compounds have been disclosed as a binaphthyl structure in the field of OLEDs. A specific example is Mol. Cryst. Liq. Cryst., Vol. 531: DNBN (blue emission subject) on page 55/[355] 64 = [364], TPBND published on SPIE (pages 198 to 208). (HTL) and Adv.Funct.Mater. BN1 (blue emission dopant and HTL) of 2010, 20, 24482458, and examples disclosed in Japanese Patent No. 4,215,837 and Korean Patent Application No. 2006-0080471, and Korean Patent Application No. 2008-0040498.

The present inventors conducted intensive studies on the development of materials having the following two amine groups directly bonded to DNBN (4,4'-(dinaphthyl-2-yl)-1,1' -binaphthyl) and BN1 (4,4'-(1,1'-binaphthyl-4,4'-diyl)bis(N,N-diphenylaniline)) 1,1'-binaphthyl 4,4' position, and the material can be used as a hole material different from the previous literature (hole transport material or hole injection material, such as TPBND (3,3'-dimethyl-N4, N4, N4' , N4'-tetraphenyl-1,1'-binaphthyl-4,4'-diamine), and Korean Patent Application No. 2006-0080471, Korean Patent Application No. 2008-0040498, and Japanese Patent No. 4215837 A luminescent material of the compound disclosed in the specification, thereby providing a compound represented by Chemical Formula 1 for illuminating an organic electroluminescence device.

The present invention is intended to provide a 1,1'-binaphthyl-4,4'-diamine derivative for use in illuminating an organic electroluminescence device, which has excellent chemical stability.

Further, the present invention is intended to provide a process for producing a 1,1'-binaphthyl-4,4'-diamine derivative for illuminating an organic electroluminescence device.

Further, the present invention is intended to provide an organic electroluminescence device comprising the 1,1'-binaphthyl-4,4'-diamine derivative.

An object of the present invention is to provide a 1,1'-binaphthyl-4,4'-diamine derivative represented by the following Chemical Formula 1 for illuminating an organic electroluminescence device.

Wherein Ar ₁ and Ar ₂ and R ₁ and R ₂ are independently the same or different from each other, Ar ₁ and Ar ₂ are phenyl, naphthalene, anthracene, phenanthrene or anthracene, and R ₁ is substituted or unsubstituted C6 to C30 aromatic. Or a substituted or unsubstituted C5-C30 heteroaryl group, R ₂ is phenyl, toluene, naphthalene, anthracene, phenanthrene, anthracene or oxazole, and n and m are integers in the range of 0 to 3.

In one embodiment of the present invention embodiment, a C6 ~ C30 aryl group, or with a substituted or non-substituted substituted or non-substituted C5 ~ C30 heteroaryl group R may be represented by the following Table ₁ of FIG. 1 Any one of the compounds selected:

Another object of the present invention is to provide a process for producing a compound of Chemical Formula 1, which comprises subjecting a compound represented by the following Chemical Formula A to a carbon-carbon coupling reaction to synthesize a compound represented by the following Chemical Formula B; The compound shown is subjected to an amination reaction to prepare a compound represented by Chemical Formula 1 in the following Scheme 1.

Still another object of the present invention is to provide an organic electroluminescence device comprising the compound represented by Chemical Formula 1.

Hereinafter, the present invention will be described in detail. The following description is illustrative and the invention is not limited thereto.

According to an aspect of the invention, there is provided a 1,1'-binaphthyl-4,4'-diamine derivative for illuminating an organic electroluminescence device, which is represented by the following Chemical Formula 1.

In Chemical Formula 1, Ar ₁ and Ar ₂ and R ₁ and R ₂ are independently the same or different from each other, and Ar ₁ and Ar ₂ are phenyl, naphthalene, anthracene, phenanthrene or anthracene, and R ₁ is substituted or unsubstituted. C6~C30 aryl, or substituted or unsubstituted C5~C30 heteroaryl, R ₂ is phenyl, toluene, naphthalene, anthracene, phenanthrene, anthracene or oxazole, and n and m are in the range of 0 to 3 The integer.

In one embodiment of the present invention, R ₁ of Chemical Formula 1 for illuminating an organic electroluminescent device is selected from the compounds of Table 1 below:

According to another object of the present invention, there is provided a method for producing a 1,1'-binaphthyl-4,4'-diamine derivative compound represented by the following Chemical Formula 1 for illuminating an organic electroluminescence device, the method comprising The compound represented by the following Chemical Formula A is subjected to a carbon-carbon coupling reaction to synthesize a compound represented by the following Chemical Formula B; and the compound of Chemical Formula B is subjected to an amination reaction to prepare a compound of Chemical Formula 1 in the following Scheme 1.

In Scheme 1, Ar ₁ and Ar ₂ and R ₁ and R ₂ are independently the same or different from each other, and Ar ₁ and Ar ₂ are phenyl, naphthalene, anthracene, phenanthrene or anthracene, and R ₁ is substituted or unsubstituted. C6~C30 aryl, or substituted or unsubstituted C5~C30 heteroaryl, R ₂ is phenyl, toluene, naphthalene, anthracene, phenanthrene, anthracene or oxazole, and n and m are in the range of 0 to 3 The integer.

In one embodiment of the present invention, as the substituted or unsubstituted C6 ~ C30 aryl group, or substituted or unsubstituted aryl of C5 ~ C30 heteroaryl _group, R ₁ is selected by the Table 1 in which any one of compound By.

The following reagents can be used to specify the individual steps of the preparation method, but the invention is not limited thereto.

The compound of formula B is prepared as follows.

In a reactor, N-phenyl-1-naphthylamine [Chemical Formula A] was dissolved in CH ₂ Cl ₂ under a nitrogen stream, and TiCl _{4 was} added dropwise, after which a saturated aqueous solution of potassium carbonate was added to the resulting solution. It was stirred and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO ₄ , evaporated and evaporated.

Subsequently, a compound of Chemical Formula 1 is prepared from the compound of Chemical Formula B as follows.

In the case where X-Ar ₁ -[R ₁ ] _{n is} different from X-Ar ₂ -[R ₂ ] _m , the compound of formula B and the compound X-Ar ₁ containing halogen (X=Br, I, Cl) are made. -[R ₁ ] _n (required for the preparation of Chemical Formula 1) is dissolved in a solvent in a reactor, and Pd ₂ (dba) ₃ , Na(t-Bu)O, and (t-Bu) ₃ PHBF _{4 are added} , which The resulting solution was then heated and stirred. After the completion of the reaction, the reaction solution was extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure and purified by EtOAc EtOAc Further, a compound of Chemical Formula 1 was obtained in the same manner using X-Ar ₂ -[R ₂ ] _m . On the other hand, in the case where X-Ar ₁ -[R ₁ ] _{n is the} same as X-Ar ₂ -[R ₂ ] _m , the compound of Chemical Formula 1 is obtained using the above procedure.

The reagent or reaction solvent used in the above reaction is not particularly limited thereto.

In addition to the use of the above compounds as the luminescent material, the organic electroluminescent device of the present invention can be produced using a typical method of manufacturing an organic electroluminescence device and a material used therefor.

According to another object of the present invention, an organic electroluminescence device using the compound of Chemical Formula 1 is provided.

In an embodiment of the invention, the organic electroluminescent device is an organic light-emitting device (OLED), an organic solar cell (OSC), an electronic paper, an organic photoconductor (organic photoconductor, OPC) and organic thin-film (organic thin-film) Selected from transistor, OTFT).

As shown in FIGS. 1 and 2, the OLED can be configured such that an organic layer is disposed between the anode as the first electrode and the cathode as the second electrode, and the compound of the present invention can be used as a luminescent material.

For example, the OLED of the present invention can be fabricated by depositing a metal, a conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation to form An anode; forming an organic layer including a hole injection layer, a hole transport layer, an emission layer, a hole barrier layer, and an electron transport layer on the anode; and depositing a material for the cathode on the organic layer. In addition to the above methods, the OLED can also be fabricated by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, an emission layer, a hole barrier layer, and an electron transport layer. Further, the organic layer can be produced using various polymer materials by using a solvent method such as spin coating, dip coating, blade scraping, screen printing, ink jet printing or heat transfer without using a deposition method. A smaller number of layers.

The anode material can be a material having a high work function in order to be able to efficiently inject holes into the organic layer. Specific examples of anode materials suitable for use in the present invention include, but are not limited to, metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), Titanium oxide (TiO) or indium zinc oxide (IZO); a combination of a metal and an oxide such as ZnO:Al or SnO ₂ :Sb; a conductive polymer such as poly(3-methylthiophene), poly[3,4- (Extended ethyl-1,2-dioxy)thiophene] (PEDT), polypyrrole, polyaniline, and the like.

The cathode material can be a material having a low work function to facilitate injecting electrons into the organic layer. Specific examples of cathode materials suitable for use in the present invention include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, antimony, lithium, gallium, aluminum, silver, tin, and lead, and alloys thereof; Materials such as LiAl and LiF/Al or LiO ₂ /Al.

The hole injection material may be a material capable of effectively receiving a hole from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) level of the hole injection material may belong to a work function of the anode material. Within the range between HOMO and organic layers. Materials that have good surface adhesion to the anode and have the ability to reduce the surface roughness of the anode are also suitable. HOMO and materials with a minimum unoccupied Molecular Orbital (LUMO) energy level greater than the band gap of the emissive layer are particularly suitable.

In addition, materials having a chemical structure with high thermal stability are suitable. Specific examples of the hole injecting material include, but are not limited to, organic materials such as metalloporphyrin, oligothiophene, arylamine, etc.; organic materials such as hexaazatriphenylene hexanitrile; An organic material such as ketone or the like; an organic material such as ruthenium; and a conductive polymer such as ruthenium, polyaniline, polythiophene or the like.

The hole transport material can be a material having high hole mobility such that holes can be transported from the anode or hole injection layer to the emissive layer. Materials in which the HOMO and LUMO levels are greater than the band gap of the emissive layer are suitable. Materials with a chemical structure with high thermal stability are also suitable. Specific examples thereof include an organic material such as an aromatic amine, a conductive polymer, and a block copolymer having a conjugated and non-conjugated moiety.

Typically, the hole material is mainly exemplified by TPD (N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-benzidine) having a diamine structure, NPB. (N,N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)-benzidine), b-NPB (N,N'-bis(naphthalen-2-yl)-N, N'-bis(phenyl)-benzidine), PAPB (N,N'-bis(phenanthrene-9-yl)-N,N'-bis(phenyl)-benzidine), a-TNB (N, N,N',N'-tetra-naphthalen-2-yl-benzidine) or a,b-TNB(N,N'-di(naphthyl)-N,N'-di(naphthalen-2-yl) -benzidine). N-diaryl structure of hydrazine or hydrazine, such as TPA (9,10-bis[phenyl(m-tolyl)-amino] hydrazine), TTPA (9,10-bis[N,N-di-( p-Tolyl)-amino]oxime), BA-NPB (N ¹⁰ ,N ^{10 '} -diphenyl-N ¹⁰ ,N ^{10 '} -binaphthyl-9,9'-biindole-10,10'- Diamine), BA-TAD (N ¹⁰ , N ¹⁰ , N ^{10 '} , N ^{10 '} -tetraphenyl-9,9'-biindole-10,10'-diamine), BA-TTB [N ¹⁰ , N ¹⁰ , N ^{10 '} , N ^{10 '} -tetramethyl-9,9'-biindole-10,10'-diamine] can be used as a green dopant. The emission wavelengths of MT-01, MT-02, and MT-03 disclosed in Japanese Patent No. 4215837 are 441 nm, 439 nm, and 436 nm, respectively, which are evaluated to be too short. In order to obtain an emission wavelength of 450 nm to 460 nm required for blue light emission, the emission wavelength and efficiency should be adjusted using Ar ₁ , Ar ₂ , R ₁ and R _{2 of} Chemical Formula 1.

The hole blocking material may be a material having a HOMO energy level greater than that of the emission layer. Materials having a chemical structure with high thermal stability are suitable. Specific examples thereof include, but are not limited to, TPBi (2,2',2"-(1,3,5-benzenetriyl)-parade (1-phenyl-1-H-benzimidazole)) and BCP ( 2,9-Dimethyl-4,7-diphenyl-1,10-morpholine), which is the main user; CBP (4,4'-bis(carbazol-9-yl)biphenyl), PBD (2-(4-biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole) and PTCBI (bisbenzimidazo[2,1-a: 1',2-b']蒽[2,1,9-def:6,5,10-d'e'f']diisoquinoline-10,21-dione), BPhen(4,7- Diphenyl-1,10-morpholine) and the like.

The electron transporting material can be a material having a high electron mobility so that electrons can be transported from the cathode to the emissive layer. Materials with a chemical structure with high thermal stability are also suitable. Specific examples thereof include, but are not limited to, 8-hydroxyquinoline aluminum complex, Alq ₃ complex, organic radical compound, hydroxyflavone-metal complex, and the like.

The luminescent material may be a material having high quantum efficiency so that holes and electrons transmitted from the hole transport layer and the electron transport layer are combined to emit in the visible light range. The light inside. Specific examples thereof include a blue luminescent material such as ADN (9,10-di(naphthalen-2-yl)anthracene), MADN (2-methyl-9,10-bis(naphthalen-2-yl)anthracene), DPVBi (4,4'-bis(2,2'-diphenylvinyl)-1,1'-biphenyl), BAlq (bis(2-methyl-8-quinolinyl)-4-(phenyl) Phenolic group) aluminum; etc.; green luminescent materials such as Alq3 and other ruthenium, osmium, iridium, sulfonium, oxazole, benzoxazole, benzothiazole, benzimidazole compounds, polymeric poly(p-phenylene ethylene) Base), polyspiral, polyfluorene, etc., but its efficiency is not satisfactory.

First, the blue luminescent material is required to have an emission wavelength of 445 nm to 470 nm. If the emission wavelength is too short, the band gap (Eg) may increase, thereby unnecessarily increasing the driving voltage or accumulating many layers. Second, there is currently a need for 6 candelas per amp (cd/A) to 7 candelas per amp or greater than 7 candelas per amp. The measurement varies depending on the type of method of manufacturing the device, and the performance is compared using standard materials. Third, thermal stability is required and the glass transition temperature (Tg) should be 120 ° C or greater than 120 ° C. Tg is related to lifetime because it is related to the thermal stability of the structure of the compound. Fourth, long life is required, and the life is affected by various factors such as driving voltage, purity, thermal stability, etc., and is mainly affected by device configuration, compound structure, and purity. Fifth, HOMO should be 5.7 eV to 6.0 eV, and the bandgap (Eg) should be 2.9 eV or greater than 2.9 eV. If the HOMO is 6.0 eV or greater than 6.0 eV, the difference from the hole transport layer (HTL; 5.6 eV to 5.7 eV) may increase, thereby increasing the driving voltage.

The present inventors have been working to solve the green wavelengths of N-diaryl structures (TPD, TPA, TTPA, BA-NPB, BA-TAD, BA-TTB) such as conventional hydrazine or hydrazine, and MT-01 in JP 4215837. , MT-02 and MT-03, the problem of too short wavelength, and the synthesis of the compound of the chemical formula 1 and its use as a control of 9,10-di-(2-naphthyl)anthracene (ADN) with respect to emission efficiency And the wavelength is compared. Therefore, it was confirmed that the compound of the present invention exhibited excellent emission efficiency and a desired wavelength.

The OLED of the present invention may be of a front emission type, a back emission type or a double side emission type depending on the type of material used. According to principles similar to those applied to OLEDs, the compounds of the invention may also function in organic electroluminescent devices, including organic solar cells, illuminated OLEDs, flexible OLEDs, organic photoconductors, organic transistors, and the like.

A better understanding of the present invention can be obtained by the following examples, which are set forth to illustrate the invention, but should not be construed as limiting the invention.

[Example] Intermediate product [1]: Preparation of N4,N4'-diphenyl-1,1'-binaphthyl-4,4'-diamine [A-01]

(1) N-phenyl-1-naphthylamine (5 mmol) was dissolved in dichloromethane under a nitrogen stream, after which the temperature of the solution was maintained at -5 ° C and then TiCl ₄ (TiCl was added dropwise) ₄ /CH ₂ Cl ₂ 1:1 solution, 1.7 mmoles for 5 minutes, followed by a reaction at -5 ° C for 1 hour and then at 0 ° C for 8 hours.

(2) was added to the reaction solution with saturated aqueous potassium carbonate solution (10 mL), and then (2 × 15 mL) ₂ Cl ₂ 30 CH minutes stirring at 0 deg.] C, to thereby obtain the organic layer subsequently MgSO ₄ ( Drying with anhydrous magnesium sulfate), dehydration under reduced pressure, and purification using silica gel chromatography to give a brown solid compound. The NMR data is shown in Figure 4.

The following compounds represent the compounds obtained in Synthesis Example 1 to Synthesis Example 15:

Synthesis Example 1: Preparation of A-1

Preparation of 4-bromo-1,2-diiodobenzene

(1) 55 ml of H ₂ SO _{4 was} placed in a double neck reactor, the reactor temperature was maintained at 0 ° C, 7.95 g of NaNO ₂ was added at 0 ° C, and the reaction mixture was stirred. The temperature was gradually increased to effect dissolution at 70 ° C for 20 minutes and then cooled to room temperature.

(2) 75 ml of AcOH was placed in a double neck reactor, and 9.35 g of 4-bromobenzene-1,2-diamine was added and slowly dissolved therein.

(3) 4-Bromobenzene-1,2-diamine dissolved in AcOH was slowly added dropwise to NaNO ₂ /H ₂ SO ₄ at 0 °C.

(4) In a double neck reactor, 19 g of KI was dissolved in 300 ml of H ₂ O, and the resulting solution was stirred at 60 °C.

The mixture obtained in the previous step was slowly added dropwise to the KI solution. After 15 minutes, an aqueous NaOH solution (130 g / 250 ml) was gradually added dropwise.

(5) After the completion of the reaction, the reaction solution was cooled, stirred with 300 ml of CH ₂ Cl ₂ and extracted with CH ₂ Cl ₂ to obtain an organic layer which was then dried over MgSO ₄ , dehydrated under reduced pressure and used Purification by silica gel chromatography gave white crystals in 40% yield.

Preparation of 4-bromo-1,2-diphenylbenzene

(1) 4-bromo-1,2-diphenylbenzene (4.2 mmol), phenylboronic acid (9.1 mmol) and Pd(PPh ₃ ) ₄ (0.21 mmol) were placed in a three-neck reaction Dissolved in 5 ml of THF under a stream of nitrogen.

(2) 2 MK ₂ CO ₃ was slowly added to the above solution, and then the solution was heated and stirred to react at 110 ° C for 12 hours.

(3) After completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ . The organic layer was then dried over MgSO _4, dehydrated under reduced pressure, and purified using silica gel chromatography, to give 60% yield of 0.72 g of the title compound.

Preparation A-1

(1) Add A-01 intermediate (1.145 mmol) and 4-bromo-1,2-diphenylbenzene (2.519 mmol), and add 0.096 g (0.1053 mmol) Pd ₂ (dba) ₃ 0.759 g (7.902 mmol) of Na(t-Bu)O and 0.031 g (0.1053 mmol) (t-Bu) ₃ PHBF ₄ and then dissolved in 20 ml of toluene under a stream of nitrogen at 120 ° C The resulting solution was heated and stirred for 12 hours.

(2) After the completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure, and purified using silica gel chromatography The yield gave 0.56 g of product. Its DSC data is shown in Figure 5A. MS[M+H]+=893.1

¹ H-NMR (CDCl ₃ , 400 NMR) δ (ppm) 8.114 (t, 2H), 7.583-7.537 (m, 6H), 7.506-7.480 (m, 7H), 7.411-7.383 (m, 8H), 7.315- 7.259 (m, 14H), 7.211-7.171 (m, 8H), 7.083 (m, 1H), 6.997-6.976 (m, 2H)

Synthesis Example 2: Preparation of A-2

Preparation A-02

(1) A-01 intermediate (1.145 mmol) and 3-bromobiphenyl (1.2595 mmol) were placed in a three-neck reactor, and 0.096 g (0.1053 mmol) Pd ₂ (dba) was added. ₃ , 0.759 g (7.902 mmol) of Na(t-Bu)O and 0.031 g (0.1053 mmol) (t-Bu) ₃ PHBF ₄ and then dissolved in 20 ml of toluene under a stream of nitrogen at 70 ° C The resulting solution was heated and stirred for 6 hours.

(2) After the completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure and purified by silica gel chromatography The rate gave 0.34 g of the title compound.

Preparation A-2

(1) A-02 intermediate (1.145 mmol) and 4-bromo-1,2-diphenylbenzene (1.2595 mmol) were placed in a three-neck reactor with 0.096 g (0.1053 mmol) Ear) Pd ₂ (dba) ₃ , 0.759 g (7.902 mmol) Na(t-Bu)O and 0.031 g (0.1053 mmol) (t-Bu) ₃ PHBF ₄ and then dissolved in 20 ml under a stream of nitrogen The resulting solution was heated and stirred at 120 ° C for 12 hours in toluene.

(2) After the completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure and purified using silica gel chromatography The rate gave 0.65 grams of product. Its DSC data is shown in Figure 5B. MS[M+H]+=817.0

¹ H-NMR (CDCl ₃ , 400 NMR) δ (ppm) 8.12-8.10 (d, 2H), 7.58-7.549 (t, 6H), 7.541-7.52 (d, 2H), 7.503-7.487 (d, 6H), 7.431-7.392(t,6H),7.371-7.347(d,4H),7.330-7.309(m,8H),7.214-7.174(t,8H),7.029-6.993(t,2H)

Synthesis Example 3: Preparation of A-3

Preparation A-03

(1) A-01 intermediate product (1.145 mmol) and 9-bromophenanthrene (1.2595 mmol) were placed in a three-neck reactor, and 0.016 g (0.1053 mmol) of Pd ₂ (dba) _{3 was added.} 0.759 g (7.902 mmol) of Na(t-Bu)O and 0.031 g (0.1053 mmol) (t-Bu) ₃ PHBF ₄ and then dissolved in 20 ml of toluene under a stream of nitrogen at 70 ° C The resulting solution was heated and stirred for 6 hours.

(2) After the completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure and purified by silica gel chromatography The rate gave 0.34 g of the title compound. MS[M+H]+=841.1

Preparation A-3

(1) A-03 intermediate (1.145 mmol) and 4-bromo-1,2-diphenylbenzene (1.2595 mmol) were placed in a three-neck reactor with 0.096 g (0.1053 mmol) Ear) Pd ₂ (dba) ₃ , 0.759 g (7.902 mmol) Na(t-Bu)O and 0.031 g (0.1053 mmol) (t-Bu) ₃ PHBF ₄ and then dissolved in 20 ml under a stream of nitrogen The resulting solution was heated and stirred at 120 ° C for 12 hours in toluene.

(2) After the completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure and purified using silica gel chromatography The rate gave 0.69 grams of product.

Synthesis Example 4: Preparation of A-4

Preparation of 1-(4-bromophenyl)naphthalene

(1) 1,4-dibromobenzene (21.2 mmol), naphthalene-1-boronic acid (31.8 mmol) and Pd(PPh ₃ ) ₄ (1.06 mmol) were placed in a three-neck reactor. And dissolved in 50 ml of THF under a stream of nitrogen.

(2) 2 MK ₂ CO ₃ was slowly added to the above solution, and the resulting solution was heated and stirred to react at 70 ° C for 6 hours.

(3) After completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure and purified using silica gel chromatography The rate yielded 3.6 grams of the title compound.

Preparation A-4

(1) A-01 intermediate (1.145 mmol) and 1-(4-bromophenyl)naphthalene (2.519 mmol) were placed in a three-neck reactor with 0.096 g (0.1053 mmol) Pd ₂ (dba) ₃ , 0.759 g (7.902 mmol) Na(t-Bu)O and 0.031 g (0.1053 mmol) (t-Bu) ₃ PHBF ₄ and then dissolved in 20 ml of toluene under a stream of nitrogen And the resulting solution was heated and stirred at 120 ° C for 12 hours.

(2) After the completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure and purified using silica gel chromatography The rate gave 0.69 grams of product. MS[M+H]+=841.1

¹ H-NMR (CDCl ₃ , 400 NMR) δ (ppm) 8.192 (d, 2H), 8.052 (d, 2H), 7..07 (d, 2H), 7.844 (d, 2H), 7.615-7.557 (m, 6H) , 7.518-7.441 (m, 10H), 7.405-7.384 (m, 6H), 7.337-7.315 (m, 8H), 7.233 (m, 4H), 7.029 (t, 2H)

Synthesis Example 5: Preparation of A-5

(1) A-02 intermediate (1.145 mmol) and 1-(4-bromophenyl)naphthalene (1.2595 mmol) were placed in a three-neck reactor with 0.096 g (0.1053 mmol) Pd ₂ (dba) ₃ , 0.759 g (7.902 mmol) Na(t-Bu)O and 0.031 g (0.1053 mmol) (t-Bu) ₃ PHBF ₄ and then dissolved in 20 ml of toluene under a stream of nitrogen And the resulting solution was heated and stirred at 120 ° C for 12 hours.

(2) After the completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure, and purified using silica gel chromatography The rate gave 0.65 grams of product. Its DSC data is shown in Figure 5C. MS[M+H]+=791.0

¹ H-NMR (CDCl ₃ , 400 NMR) δ (ppm) 8.184 (d, 1H), 8.134 (d, 1H), 8.051 (d, 1H), 7. 910 (d, 1H), 7.842 (d, 1H), 7.583 (m, 3H), 7.515-7.379 (m, 18H), 7.330-7.268 (m, 8H), 7.204 (m, 5H), 7.086 (d, 1H), 7.020-6.999 (dd, 2H)

Synthesis Example 6: Preparation of A-6

Preparation of 1-(3-bromophenyl)naphthalene

(1) 1,3-dibromobenzene (21.2 mmol), naphthalene-1-boronic acid (31.8 mmol), and Pd(PPh ₃ ) ₄ (1.06 mmol) were placed in a three-neck reactor. And dissolved in 50 ml of THF under a stream of nitrogen.

(2) 2 MK ₂ CO ₃ was slowly added to the above solution, and the resulting solution was heated and stirred to react at 70 ° C for 6 hours.

(3) After completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure and purified using silica gel chromatography The rate yielded 3.6 grams of the title compound.

Preparation A-6

(1) A-01 intermediate (1.145 mmol) and 1-(3-bromophenyl)naphthalene (2.519 mmol) were placed in a three-neck reactor with 0.096 g (0.1053 mmol) Pd ₂ (dba) ₃ , 0.759 g (7.902 mmol) Na(t-Bu)O and 0.031 g (0.1053 mmol) (t-Bu) ₃ PHBF ₄ and then dissolved in 20 ml of toluene under a stream of nitrogen And the resulting solution was heated and stirred at 120 ° C for 12 hours.

(2) After the completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure and purified using silica gel chromatography The rate gave 0.67 g of product. MS[M+H]+=841.1

¹ H-NMR (CDCl ₃ , 400 NMR) δ (ppm) 8.160 (d, 2H), 7.852 (dd, 4H), 7.666 (d, 2H), 7.472 (m, 6H), 7.431-7.382 (m, 10H) , 7.281(m,8H), 7.241-7.153(m,8H),7.111(d,2H),6.999(t,2H)

Synthesis Example 7: Preparation A-7

(1) A-02 intermediate (1.145 mmol) and 1-(3-bromophenyl)naphthalene (1.2595 mmol) were placed in a three-neck reactor with 0.096 g (0.1053 mmol) Pd ₂ (dba) ₃ , 0.759 g (7.902 mmol) Na(t-Bu)O and 0.031 g (0.1053 mmol) (t-Bu) ₃ PHBF ₄ and then dissolved in 20 ml of toluene under a stream of nitrogen And the resulting solution was heated and stirred at 120 ° C for 12 hours.

(2) After completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure and purified using silica gel chromatography The rate gave 0.68 grams of product. Its DSC data is shown in Figure 5D. MS[M+H]+=791.0

¹ H-NMR (CDCl ₃ , 400 NMR) δ (ppm) 8.172-8.094 (dd, 2H), 7.851-7.791 (dd, 2H), 7.495 (m, 9H), 7.387 (m, 10H), 7.331-7.259 ( m, 9H), 7.197 (m, 6H), 7.12-7.060 (dd, 2H), 6.995 (t, 2H)

Synthesis Example 8: A-8

(1) A-01 intermediate product (1.145 mmol) and 3,5-bis(4-methylphenyl)bromobenzene (2.519 mmol) were placed in a three-neck reactor with the addition of 0.096 g ( 0.1053 mmol) Pd ₂ (dba) ₃ , 0.759 g (7.902 mmol) Na(t-Bu)O and 0.031 g (0.1053 mmol) (t-Bu) ₃ PHBF ₄ and then dissolved under a nitrogen stream The resulting solution was heated and stirred at 120 ° C for 20 hours in 20 ml of toluene.

(2) After the completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure, and purified using silica gel chromatography The rate yielded 0.7 grams of product. MS[M+H]+=949.2

Synthesis Example 9: Preparation A-9

Preparation of 9-(4-bromophenyl)-9H-carbazole

(1) Place 1,4-dibromobenzene (21.2 mmol) and 9 H -carbazole (31.8 mmol) in a three-neck reactor with Pd ₂ (dba) ₃ (0.9752 mmol) ), Na(t-Bu)O (73.14 mmol) and (t-Bu) ₃ PHBF ₄ (0.9752 mmol) and then dissolved in 100 ml of toluene under a stream of nitrogen, and heated and stirred at 70 ° C The resulting solution was continued for 6 hours.

(2) After completion of the reaction, the reaction solution was cooled and extracted with CH ₂ CL ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure and purified using silica gel chromatography The rate gave 3 g of the title compound.

Preparation A-9

(1) A-01 intermediate (1.145 mmol) and 9-(4-bromophenyl)-9H-carbazole (2.519 mmol) were placed in a three-neck reactor with 0.096 g (0.1053) Millol) Pd ₂ (dba) ₃ , 0.759 g (7.902 mmol) Na(t-Bu)O and 0.031 g (0.1053 mmol) (t-Bu) ₃ PHBF ₄ and then dissolved in a stream of nitrogen In 20 ml of toluene, the resulting solution was heated and stirred at 120 ° C for 12 hours.

(2) After completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure and purified using silica gel chromatography The rate gave 0.63 grams of product. MS[M+H]+=919.1

Synthesis Example 10: Preparation of A-10

Preparation of 9-(4-bromophenyl)phenanthrene

(1) 9-bromophenanthrene (21.2 mmol), 4-bromophenylboronic acid (31.8 mmol), and Pd(PPh ₃ ) ₄ (1.06 mmol) were placed in a three-neck reactor, and Dissolved in 50 ml of THF under a stream of nitrogen.

(2) 2 MK ₂ CO ₃ was slowly added to the above solution, and the resulting solution was heated and stirred to react at 70 ° C for 6 hours.

(3) After the completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure and purified using silica gel chromatography The rate gave 5 g of the title compound.

Preparation A-10

(1) A-01 intermediate (1.145 mmol) and 9-(4-bromophenyl)phenanthrene (2.519 mmol) were placed in a three-neck reactor with 0.096 g (0.1053 mmol) Pd ₂ (dba) ₃ , 0.759 g (7.902 mmol) Na(t-Bu)O and 0.031 g (0.1053 mmol) (t-Bu) ₃ PHBF ₄ and then dissolved in 20 ml of toluene under a stream of nitrogen And the resulting solution was heated and stirred at 120 ° C for 12 hours.

(2) After completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure and purified using silica gel chromatography The rate yielded 0.8 g of product. MS[M+H]+=941.2

Synthesis Example 11: Preparation of A-11

(1) A-01 intermediate (1.145 mmol) and 9-(4-bromophenyl)fluorene (2.519 mmol) were placed in a three-neck reactor with 0.096 g (0.1053 mmol) Pd ₂ (dba) ₃ , 0.759 g (7.902 mmol) Na(t-Bu)O and 0.031 g (0.1053 mmol) (t-Bu) ₃ PHBF ₄ and then dissolved in 20 ml of toluene under a stream of nitrogen And the resulting solution was heated and stirred at 120 ° C for 12 hours.

(2) After the completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure and purified using silica gel chromatography The rate gave 0.78 grams of product. MS[M+H]+=941.2

Synthesis Example 12: Preparation of A-12

Preparation of 4'-bromo-1,1'-binaphthyl

(1) 1,4-dibromonaphthalene (21.2 mmol), naphthalene-1-boronic acid (31.8 mmol), and Pd(PPh ₃ ) ₄ (1.06 mmol) were placed in a three-neck reactor. And dissolved in 50 ml of THF under a stream of nitrogen.

(2) 2 MK ₂ CO ₃ was slowly added to the above solution, and the resulting solution was heated and stirred to react at 70 ° C for 6 hours.

(3) After the completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure, and purified using silica gel chromatography The rate gave 3.88 g of the title compound.

A-12

(1) A-01 intermediate (1.145 mmol) and 4'-bromo-1,1'-binaphthyl (2.519 mmol) were placed in a three-neck reactor, adding 0.096 g (0.1053 mmol) Ear) Pd ₂ (dba) ₃ , 0.759 g (7.902 mmol) Na(t-Bu)O and 0.031 g (0.1053 mmol) (t-Bu) ₃ PHBF ₄ and then dissolved in 20 ml under a stream of nitrogen The resulting solution was heated and stirred at 120 ° C for 12 hours in toluene.

(2) After the completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure and purified using silica gel chromatography The rate gave 0.72 grams of product. MS[M+H]+=941.2

Synthesis Example 13: Preparation A-13

(1) A-01 intermediate (1.145 mmol) and 4-bromo-1,3'-binaphthyl (2.519 mmol) were placed in a three-neck reactor with 0.096 g (0.1053 mmol) Pd ₂ (dba) ₃ , 0.759 g (7.902 mmol) Na(t-Bu)O and 0.031 g (0.1053 mmol) (t-Bu) ₃ PHBF ₄ and then dissolved in 20 ml of toluene under a stream of nitrogen The solution was heated and stirred at 120 ° C for 12 hours.

(2) After completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure and purified using silica gel chromatography The rate yielded 0.8 g of product. MS[M+H]+=941.2

Synthesis Example 14: Preparation A-14

(1) A-01 intermediate product (1.145 mmol) and 2-bromo-7-(naphthalen-1-yl)phenanthrene (2.519 mmol) were placed in a three-neck reactor with 0.096 g (0.1053) Millol) Pd ₂ (dba) ₃ , 0.759 g (7.902 mmol) Na(t-Bu)O and 0.031 g (0.1053 mmol) (t-Bu) ₃ PHBF ₄ and then dissolved in a stream of nitrogen In 20 ml of toluene, the resulting solution was heated and stirred at 120 ° C for 12 hours.

(2) After the completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure and purified using silica gel chromatography The rate gave 0.87 g of product. MS[M+H]+=1041.3

Synthesis Example 15: Preparation of A-15

(1) A-01 intermediate product (1.145 mmol) and 1-bromo-6-(naphthalen-1-yl)anthracene (2.519 mmol) were placed in a three-neck reactor with 0.096 g (0.1053) Millol) Pd ₂ (dba) ₃ , 0.759 g (7.902 mmol) Na(t-Bu)O and 0.031 g (0.1053 mmol) (t-Bu) ₃ PHBF ₄ and then dissolved in a stream of nitrogen In 20 ml of toluene, the resulting solution was heated and stirred at 120 ° C for 12 hours.

(2) After the completion of the reaction, the reaction solution was cooled and extracted with CH ₂ Cl ₂ to give an organic layer, which was then dried over MgSO _{4 ,} dried under reduced pressure and purified using silica gel chromatography The rate gave 0.87 g of product. MS[M+H]+=1089.3

<OLED>

In the comparative examples and examples, the hole transport layer is made of NPB (N, N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)-benzidine) or JP4215837, luminescent material. For the AND-only (9,10-bis(naphthalen-2-yl)fluorene) host or the AND host and one of the dopants A-1 to A-15, the hole blocking layer is composed of TPBi (2, 2',2"-(1,3,5-phenyltriyl)-parade (1-phenyl-1-H-benzimidazole)), and the electron transport layer is composed of Alq ₃ (parameter (8- Made of hydroxy-quinolyl) aluminum) or LiF (lithium fluoride).

Comparative Example 1: ITO/NPB/ADN/TPBi/Alq ₃ /LiF/Al

A glass substrate coated with a ITO (Indium Tin Oxide) film having a thickness of 1500 angstroms was placed in secondary distilled water in which a detergent purchased from Fischer was dissolved, and washed in an ultrasonic manner. The ITO was washed twice with distilled water for 30 minutes and then washed by ultrasonic for 10 minutes. bell. After washing with distilled water is completed, the substrate is ultrasonically washed using a solvent such as isopropyl alcohol, acetone or methanol, dried, and transferred to a plasma cleaner. The substrate was washed with oxygen plasma for 5 minutes and then transferred to a vacuum evaporator.

a hole layer NPB having a thickness of 700 angstroms, an emission layer having a thickness of 300 angstroms using a ruthenium-based ADN compound, a hole barrier layer having a thickness of 200 angstroms using a TPBi compound, and a thickness of 400 angstroms using an Alq ₃ compound. The electron transport layer was vacuum deposited on the thus prepared ITO transparent electrode, followed by depositing 5 angstroms of LiF and 1000 angstroms of Al (aluminum) in order to form a cathode. In this procedure, the deposition rate of the organic material was maintained at 1 angstrom/second, the lithium fluoride was 0.2 angstrom/second, and the Al was 3 angstrom/second to 7 angstrom/second.

The electroluminescent properties of the manufactured OLEDs are shown in Table 2 below.

Comparative Example 2: ITO/JP4215837/ADN/TPBi/Alq ₃ /LiF/Al

An OLED was fabricated in the same manner as in Comparative Example 1, except that JP4215837 was not vacuum deposited at a thickness of 700 angstroms instead of NPB as a hole transporting material.

Example 1: ITO/NPB/ADN: A-1/TPBi/Alq ₃ /LiF/Al

An OLED was manufactured in the same manner as in Comparative Example 1, except that the ADN of the emission layer was doped with 0.5% of the A-1 compound of Synthesis Example 1.

Example 2 to Example 15

The OLED was fabricated in the same manner as in Example 1 except that A-2 to A-15 were used instead of A-1, respectively. The electroluminescent properties of OLEDs are shown in Table 2 below.

The properties of the OLEDs of Comparative Example 1 and Comparative Example 2 and Examples 1 to 15 were evaluated. The results are shown in Table 2 below. The unit of current density is mA A/cm2, the unit of color coordinates is CIE 1931 (x, y), the efficiency is calculated using brightness and current density and its unit is candle/ampere, and the life is in hours under 1000 nits.

As apparent from Table 2, the compound represented by Chemical Formula 1 according to the present invention can be used to form a thin film layer for OLED light emission, and emit light in blue, sky blue, and green wavelength ranges, and its color coordinates, emission efficiency, and lifetime are obtained. Improvement.

Specifically, an example in which ADN is doped with a compound of Chemical Formula 1 (wherein R ₂ is a phenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group or a fluorenyl group) can be observed as compared with the ruthenium compound (AND) of the comparative example. Color coordinates at various wavelengths, excellent emission efficiency, and improved lifetime.

According to the present invention, the 1,1'-binaphthyl-4,4'-diamine derivative for OLED light emission can produce blue light emission, high emission efficiency, and long life. Therefore, such an OLED can be actually used and it is extremely easy to obtain industrially. The OLED of the present invention can be suitably applied to a flat panel display, a flat panel luminescent material, a luminescent material for illuminating a surface emitting OLED, a flexible luminescent material, a photocopier, a printer, a light source of a meter or an LCD backlight, and a display panel. , indicators, etc.

Although the embodiments of the present invention have been disclosed for the purpose of illustration, it will be understood by those of ordinary skill in the art that, without departing from the scope and spirit of the invention as disclosed in the appended claims Different modifications, additions, and substitutions are possible. Accordingly, the modifications, additions and substitutions are also to be understood as falling within the scope of the invention.

1 schematically illustrates the structure of an OLED; FIG. 2 illustrates a multilayer structure of an OLED; FIG. 3 illustrates a multilayer structure of a hole-free barrier layer; FIG. 4 illustrates NMR of an intermediate product [1]; and FIGS. 5A, 5B, 5C, and 5D shows the DSC data of Compound A-1, Compound A-2, Compound A-5 and Compound A-7, respectively.

Claims (6)

A 1,1'-binaphthyl-4,4'-diamine derivative for illuminating an organic electroluminescence device, which is represented by the following Chemical Formula 1: Wherein Ar ₁ and Ar ₂ and R ₁ and R ₂ are independently the same or different from each other, Ar ₁ and Ar ₂ are phenyl, naphthalene, anthracene, phenanthrene or anthracene, and R ₁ is substituted or unsubstituted C6-C30 aromatic Or a substituted or unsubstituted C5-C30 heteroaryl group, R ₂ is phenyl, toluene, naphthalene, anthracene, phenanthrene, anthracene or oxazole, and n and m are integers in the range of 0 to 3. The 1,1'-binaphthyl-4,4'-diamine derivative as described in claim 1, wherein R ₁ is selected from the compounds shown in Table 1 below: [Table 1] A method for producing a 1,1'-binaphthyl-4,4'-diamine derivative compound represented by the following Chemical Formula 1 for illuminating an organic electroluminescence device, the method comprising: a compound represented by the following chemical formula A A carbon-carbon coupling reaction occurs to synthesize a compound represented by the following Chemical Formula B; and an amination reaction of the compound represented by Chemical Formula B is carried out to prepare the compound represented by Chemical Formula 1 in the following Scheme 1: Wherein Ar ₁ and Ar ₂ and R ₁ and R ₂ are independently the same or different from each other, Ar ₁ and Ar ₂ are phenyl, naphthalene, anthracene, phenanthrene or anthracene, and R ₁ is substituted or unsubstituted C6-C30 aromatic Or a substituted or unsubstituted C5-C30 heteroaryl group, R ₂ is phenyl, toluene, naphthalene, anthracene, phenanthrene, anthracene or oxazole, and n and m are integers in the range of 0 to 3; The method of claim 3, wherein R ₁ is selected from the compounds shown in Table 1 below: [Table 1] An organic electroluminescence device comprising the compound represented by Chemical Formula 1 as described in claim 1 or 2. The organic electroluminescence device according to claim 5, wherein the organic electroluminescence device is selected from the group consisting of: an organic light-emitting device (OLED), an organic solar cell (OSC), and an electronic paper. , organic photoconductor (OPC) and organic thin film transistor (OTFT).