| Title of Invention | AN ORGANIC COMPOUND AND AN ORGANIC LIGHT EMITTING DEVICE COMPRISING SAID ORGANIC COMPOUND LAYERS DISPOSED BETWEEN ELECTRODES |
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| Abstract | The present invention relates to a novel compound that can significantly improve the lifespan, efficiency and thermal stability of an organic light emitting device, and to an organic electroluminescence device or light emitting device comprising the compound in an organic compound layer is also disclosed. |
| Full Text | WO 2005/090512 PCT/KR2005/000794 NEW MATERIALS FOR INJECTING OR TRANSPORTING HOLES AND ORGANIC ELECTROLUMINESCENCE DEVICES USING THE SAME Technical Field The present, invention relates to a novel compound that can greatly improve lifespan, efficiency and thermal stability of organic light omitting devices, and to an organic light. emitting device comprising the same compound in an organic compound layer. Background Art In the era of advanced information technology of the 21st century, a great deal of information should bo obtained promptly with ease, and thus an importance of. the high performance flat panel display for multimedia increases. Although liquid crystal displays (LCDs) have ployed the main part of" flat panel displays up to now, many attempts are made to develop novel flat, panel displays that are cost-efficient, show excellent performance and are differentiated from liquid crystal displays all over the world. Organic electroluminescence (EL) devices or organic light emitting devices chat are expected to play an important role as advanced flat panel displays have advantages of lower drive voltage, higher response rate, higher efficiency and wider view angle, compared to liquid crystal displays. In addition, because displays using organic electroluminescence phenomenon permit a total module thickness of 2 mm or less and can be manufactured on plastic substrates having a thickness of 0.3 mm or less, it is possible to meet the trend of thinning and downsizing of displays. Moreover, organic electroluminescence displays have an 1 WO 2005/090512 PCT/KR2005/000794 additional advantaqe in that thay are produced lower cost compared to liquid crystal displays. Organic .1 :. qht omit tinq devices are. based on the mechanism wherein electrons and holes injected to an organic film formed of organic; compounds through an anode and a cathode form oxitons when they are recombined and then light havinq a certain wavelength is emitted from 'he exitons. In ]965, Pope et al . found electroluminescence in an anthracene single cryst.i 1 for the first time. Following this, in 1987, Tang el al. in Kodak Co. found that an organic light emitting device formed of organic materials with a structure having separate functional. laminated layers, i.e., a hole transport layer and light emitting layer laminated to each other, can provide a high luminance of 1000 cd/m2 or higher even under a low voitage of 10V or less. After those findings, organic light, emitting devices has been a matter of great interest in the field of display technology (Tang, C.W.; Vanslyke, S. A. Appl. Phys. Lett. 1987, 51, 913). Such organic light emitting devices are classified into those using fluorescence and those using phosphorescence capable of providing a high efficiency of up to three times of the fluorescence-based efficiency. Alternatively, such organic light emitting devices may be classified according to molecular' weights of the organic materials forming organic light emitting devices, i.e., those prepared by a low-molecular weight method wherein a device is formed by using a vacuum sublimation process and those prepared by a high-molecular weight method wherein a device is formed by using solution processes such as a spin coating, ink jet printing or roll coating process. 2 WO 2005/090512 PCT/KR20005/000794 As shown in. FIG. I , a conventional organic Light emitting device "includes an anode, a hole injection layer that accepts. holes from the anode, a hole transport layer that: transports holes, a light emitting layer in which holes and electrons are recombined to emit light, an electron transport layer that accepts electrons from a cathode and transport them to the liqht emitting layer, and a cathode. The above thin film layers are formed by a vacuum deposition process. The reason for manufacturing organic light emitting devices having a multilayered thin film structure is as follows. It is possible to transport, holes and electrons to a light emitting layer more efficiently when a suitable hole transport layer and electron transport layer are used, because the moving rate of holes is significantly higher than that of electrons in organic materials. Additionally, it is possible to increase luminous efficiency when hole density is balanced with electron density in a light emitting layer. Hereinafter, a conventional organic light emitting device will be explained referring to FTG. 1. A substrate 1 is the support for an organic light emitting device and may be formed of a silicone wafer, quartz or glass plate, metal plate, plastic film or sheet, etc. Preferably, glass plates or transparent plates made of synthetic resins such as polyester, polymethacrylate or polysulfone are used. A first electrode (anode) 2 is disposed on the substrate 1. The anode serves to inject holes to a hole injection layer 3 and may be formed of metals such as aluminum, gold, silver, nickel, palladium or platinum, metal oxides such as indium-tin oxides or indium-zinc 3 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 oxides, halogennated metals, carbon black, or conductive polymers such as poly(3-methylthiophene), polypyrrole or polyani1ine. The hole injection layer 3 is disposed on the anode 2. Materials used in the hole injection layer have to provide high efficiency of hole injection from the anode and have to transport. the injected holes efficiently. In this regard, the materials should have low ionization potential, high transparency to visible light and excellent stability to holes. Materials for the hole injection layer include compounds that have excellent thermal, stability while maintaining a stable interface with the anode. Typical examples of the materials include copper phthalocyanine (CuPc), which is a porphyrin-copper complex disclosed in US Patent No. 4,356,429 by Kodak, Co. Because CuPc is the most stable compound for use in a hole injection layer, it has been used widely. However, it shows an absorption band at the blue and red zones, and thus has problems when manufacturing full-color display devices. Recently, starburst-like aromatic aryl amine compounds having no absorption band at the blue zone are known (US Patent No. 5,256,945 and Japanese Laid-Open Patent No. 1999-219788, and see the following formulae 4-12). Particularly, among the starburst-like amines having no absorption band at the blue zone, compounds represented by the following formulae 8-12 having a glass transition temperature of 1000c or higher and excellent stability are used. 4 5 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 WO 2OO5/O9O512 PCT/KR2O05/00O794 6 Recently, many hole injection materials having a higher glass transition temperature and more improved thermal stability have been reported. Most of them are compounds derived irom NPB of Kodak, Co. and are represented by the following formulae 13-17 'see,, Japanese Laid-Open Patent No. elei9-301934 and US Patent Nos. 6,334,283 and 6,541,129). WO 2OO5/O9O5I2 PCT/KR2O05/00O794 Additionally, Japanese Laid-Open Patent No. 2003-23850] discloses aromatic oligoamine derivatives having at least five nitrogen atoms in one molecule (formulae 18 and 19). Further, more recently, Japanese Laid-Open Patent 7 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 8 No. 2003-317966 and US Patent No. 6, 660, 410 disclose a carbazole group containing material (formula 20), which is specifically used as host forming a light omitting layer in. an. organic light emitting device using phosphorescence and is claimed to improve the lifespan of an organic light emitting device compared to conventionally known CBP (carbazole biphenyl ) . Other compounds used in a hole injection layer are represented by the following formulae 21-27. WO 2OO5/O9O5I2 PCT/KR2O05/00O794 A hole transport layer 4 is disposed on the hole injection layer 3. The hole transport layer serves to accept holes from the hole injection layer and transport them to an organic light, emitting layer 5 disposed thereon. The hole transport layer has high hole transportability and stability to holes. It also serves as a barrier to protect electrons. In addition to the above-mentioned basic requirements, when it is used in display devices for cars, tor example, it. is preferable that the materials for a hole transport layer have an improved heat resistance and a glass transition temperature (Tg) of 80°C or higher. Materials satisfying such requirements incJude NPB, spyro-arylamine compounds, perylene-arylamine compounds, azacycloheptatriene compounds, bis(diphenylvinylphenyl) anthracene, silicon germanium oxide compounds, silicon-containing arylamine compounds, or the like. Meanwhile, as an important organic single molecules for a hole transport layer, there is arylamine compounds having high hole transport rate and excellent electrical stability. In order to improve thermal stability of arylamine compounds, hole transport 9 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 materials into which. a naphthyl substituent or spyro group is introduced are reported (see, US Patent. Nos. 5,554,159 and 5,840,217). In the beginning, N,N'-diphenyl -N, N' b.i s ( 3-rnethylphenyl.) -1, 1' -di.phenyl-4, 4' -diamine (TPD) is frequently used as organic hole transport, material. However, because TI'D is unstable at a temperature of 60°C or higher, N-naphthyl N-phenyl-1 , 1' -diphenyl- 4 , 4 ' -diamine (NPD) based materials or amine compounds substituted with a greater number of aromatic groups that have a higher glass transition temperature are used at the present time. Particularly, organic single molecules for use in a hole transport layer should have high hole transport. rate. Additionally, because a hole transport layer is in contact with a light emitting layer and forms an interface therebetween, organic single materials for a hole transport layer should have an adequate ionization potential value of between that of a hole injection layer and that of a light emitting layer so as to inhibit the generation of exitons at the interface between hole transport layer and light emitting layer. Further, the organic single materials for a hole transport layer are required to control the electrons transported from the light emitting layer. An organic light emitting layer 5 is disposed on the hole transport layer 4. The organic light emitting layer, which serves to emit lights by the recombination of holes and electrons injected from the anode and cathode, respectively, is formed of materials having high quantum efficiency. Organic single molecules for use in a light emitting layer where light emission is accomplished by 10 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 the recombination of holer; and electrons are classified functionally into host materials and guest materials. In general, host material;; or guest materials can accomplish light, emission when used alone. However, host mater i.ais are doped with guest materials in order to solve the problems of low efficiency and luminance and the problem of self-pack ing of the same molecules that causes the excimer characteristics to come out in addition to the unique characteristics of each molecule. More particularly, as green light omitting layer, 8-hydroxyquinoline aluminum salt (Aiq3) is uniquely used and may be doped with high-quantum efficiency materials such as quinacridone or C54 51 so as to increase luminous efficiency. Organic materials for a blue Light emitting layer have problems in that they have low melting points and low luminous stability at the initial time and that they have poor lifespan, compared to Alq3 as urecn light emitting material. Additionally, because most materials for a blue light emitting layer represent a light blue color rather than pure blue color, they are not suitable for full-color version displays, and so, they are also doped with perylene or distryl amines (DSA) to increase luminous efficiency. Typical organic materials for a blue light emitting layer include aromatic hydrocarbons, spyro-type compounds, aluminum-containing organometallic compounds, heterocyclic compounds having an imidazole group, fused aromatic compounds, as disclosed in US Patent Nos. 5,516,577, 5,366,811, 5,840,217, 5,150,006 and 5,645,948. Meanwhile, in the case of a red light emitting layer, a large amount of green light emitting material doped with a small amount of red light emitting material is used due to the characteristically narrow 11 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 band gap of red light emission. However, such materials have structural problems disturbing the improvement of: lifespar.. An elecVron transport, layer. 6 is disposed on the organic light emitting layer 5. In the electron transport layer 6, such materials as having high electron injection efficiency from a cathode 7 (a second electrode) and capable of transporting the injected electrons efficiently are used. For satisfying this, the materials should have hiqh electron affinity and electron moving rate and excellent stability to electrons. Materials that meet the above requirements include: aromatic compounds such as tetraphenylbutadiene (Japanese Laid-Open Patent No. Sho57-51781) , metal complexes such as 8-hydroxyquinoline aluminum (Japanese Laid-Open Patent No. Sho59-194 393) , metal complexes of 10-hydroxybenzo[h]quinoline (Japanese Laid-Open Patent No. Hei6-322362) , cyclopentadiene derivatives (Japanese Laid-Open Patent No. Hei2-289675), bisstyrylbenzene derivatives (Japanese Laid-Open Patent Nos. Hei1 -245087 and Hei2-222484) , perylene derivatives (Japanese Laid-Open Patent Nos. Hei2-189890 and Hei3-791), p-phenylene derivatives (Japanese Laid-Open Patent Nos. Hei 3-33183 and Hei11-345686), oxazole derivatives, or the like. Additionally, preferred organic single molecules-for use in an electron transport layer include organometal complexes having relatively high stability to electrons and high electron moving rate. Particularly, it is reported that Alq3 is the most preferred, because it has excellent stability and high electron affinity. In addition to the above-mentioned materials, other electron transport materials known to 12 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 one skilled in the art include Flaven or silol scries available from Chisso Corporation. There is no especially preferred candidate ot hei than the above materials for use in the electron transport layer. Generally, electron transport materials are used in the form of a mixture with metals for use in cathodes. Otherwise, inorganic materials such as lithium fluoride (LiF) may be used. The cathode 7 serves to inject electrons to the organic light emitting layer b. As materials for the cathode, the materials used in the anode 2 may be used. However, it is preferable to use metals having low work function in order to inject electrons more efficiently. Particular examples of the metals include lithium, cesium, sodium, tin, magnesium, indium, calcium, aluminum, etc., and alloys thereof. However, the organic electroluminescence display device using organic single molecules suitable for each of the Layers forming the device generally has short life span and has problems that it provides poor shelf durability and reliability. It is thought that such problems result from physical, chemical, photochemical and electrochemical changes in organic materials, oxidation of cathode, interlayer separation, and melting, crystallization and pyro.lysis of organic compounds. Brief Description of the Drawings FIG. 1 is a sectional view showing the structure of a conventional organic electroluminescence device. 13 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 1: substrate 2: anode 3: hole injection layer 4 : hole transport layer 5: organic light: omitting Layer 6: electron transport, layer 7: cathode Disclosure of the Invention As described above, conventional hole injection materials including organometa.l complexes such as CuPC, arylamine compounds and carbazole group-containing materials. have problems in that they have a difficulty in realizing full color and show poor stability. The present inventors have synthesized novel organic compounds containing a carbazole group, represented by the following formula 1. And They have found that the above novel compounds can provide significantly improved efficiency, lifespar. and thermal stability of an organic light emitting device, when used as hole injection and transport materials. The present invention is based on such findings. As described above, it is possible to realize desired color in an organic electroluminescence device by modifying the structure of a suitable organic single molecule. In this regard, various high-efficiency organic electroluminescence devices are provided by using host-guest systems. However, such devices show insufficient luminance characteristics, lifespan and durability for practical use. Therefore, the present invention has been made in view of the above-mentioned problems. It is an object of the present invention to 14 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 provide a novel material for hole injection and hole transport layer, which can improve luminous efficiency, stability and lifespan or an organic electroluminescence device, and to provide an orqanic electro luminescence device using the same material. It is another object of the present invent: ion to provide a material havinq high glass transition temperature, excellent thermal stability and sublimation property needed for vacuum vapor deposition processes. According to an aspect of the present invention, there are provided an organic compound represented by the following formula and an organic electroluminescence device comprising the same compound in an organic compound layer: In the above formula, Rl to R1O are the same or different, and preferably each comprises, only once or 15 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 repeatedly at least two Vines, at least one selected from the group consistinq of a hydrogen atom; alipharic hydrocarbon having 1-20 carbon atoms; aromatic hydrocarbon non-substituted or substituted with a nitro, nitrile, haloqen, alkyl, alkoxy or amino qroup; silicon group having an aromatic substituent; heterocyclic aromatic hydrocarbon non-substituted or substituted with a nitro, nitrile, halogen, alkyl, alkoxy or amino group; thiophene group substituted with a C1-C20 hydrocarbon or C6-C24 aromatic hydrocarbon; and a boron group substituted with an aromatic hydrocarbon, and Ar is an aromatic hydrocarbon non-substituted or substituted with a nitro, nitrile, halogen, alkyl, alkoxy or amino group. In the above formula, each of 1, m and n is an integer of 1 or more and o is an integer of 0 or more, preferably, 1, m and n represent 1 at the same time*, and o is 0, with the proviso that the compound represented by formula 1 wherein Rl, R2, R3, RA, R5 and RG represent hydrogen atoms simultaneous.) y and U is also a hydrogen atom is excluded. The above aromatic hydrocarbon includes monocycli.c aromatic rings such as phenyl, biphenyl and terphenyl and multicyclic aromatic rings such as naphthyl, antriracenyl, phenanthracene, pyrenyl and perylenyl or the like. Additionally, the above heteroaromatic hydrocarbon includes thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, thiadiazole, triazole, pyridyl, pyridazyl, pyrazine, guinoline, isoquinoline, etc. Preferably, the compound represented by the above formula 1 may be a compound represented by any one 16 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 17 formula selected from the following formulae 2a-2e: WO 2OO5/O9O5I2 PCT/KR2O05/00O794 More preferably, the compound represented by the above formula 1 may be a compound represented by any one formula selected from the following formulae 3a-3n: 18 19 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 20 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 WO 2005/090512 PCT/KR2005/000794 In the above formulae 2a--2e and 3a-3n, each of Rl-R8 is the same as defined with regard to the above formula 1. Hereinafter, the present invention will be described in more detail. The organic compounds represented by the formula of 1, 2 or 3 are capable of serving as hole injection and hole transport materials, and thus can be used in at least one layer selected from a hole injection layer, hole transport layer and a light emitting layer in an organic light emitting device. WO 2OO5/O9O5I2 PCT/KR2O05/00O794 Particularly, each of the compounds comprises a carbazole qroup and accepts and transports holes with ease. It is thought that such functions result from the cyclic structure present in the carbazole qroup and the presence of an aryl group bonded to the carbazolo group. Therefore, an organic material layer comprising the above compound may be used as a hole injection layer or hole transport layer. Additionally, the organic material layer may be used as a light emitting layer where holes and electrons are recombincd to accomplish light emission. In other words, the compound according to the present invention can perform at least one function selected from the group consisting of hole injection, hole transport and light emission. Similarly, the Jayer comprising the above compound in an organic light emitting device can serve as at least one selected from the group consisting of a hole injection layer, hole transport layer and a light emitting layer. Additionally, the layer comprising the above compound can be used as a hole injection/hole transport layer, hole injection/hole transport/light emitting layer, etc. More particularly, it is thought that the compound may accept and transport holes stably and safely by virtue of the aryl group of the carbazole group or the aryl group bonded to the carbazole group as a substituent and the carbazole group itself. In addition, the substituent bonded to the carbazole group is derived from an amine group. Such substituents maintain the movement of holes and the structure of the compound according to the present invention in a stable state, while not disturbing the flow of holes. Therefore, the 22 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 organic light emitting device comprisinq the compound shows excellent stability and improved .lifespan. In addition, the substituents of the compound according to the present invention, i.e., R1-R10 may represent any other substituents than the groups as defined above, as long as the compound having substituents corresponding to Rl-Rl0 can perform a desired function as an organic material layer in an organic light emitting device, for example, when R1-R10 represent alkyl groups or alkyl-substituted substituents, there is no limitation in the length of each alkyl group. Because the length of an alkyl group included in the compound does not affecrt the conjugation length of the compound, it has no direct effect on the wavelength of the compound or on the characteristics of a device. However, the length of an alkyl group may affect the selection of a method of applying the compound to an organic light emitting device, for example, a vacuum deposition method or a solution coating method. Therefore, there is no particular limitation in length of alkyl groups that may be included in the compound represented by the above formulae. With regard to R1-R10 in the above formulae, particular examples of the aromatic compound include monocyclic aromatic rings such as phenyl, biphenyl, terphenyl, etc., and multicyc.lic aromatic rings such as naphthyl, anthracenyl, pyrenyl, perylenyl, etc. Particular examples of the hcteroaromatic compound include thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, thiadiazole, trriazole, pyridyl, pyridazyl, pyrazine, quinoline, isoquinol.ine, etc. 23 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 The aliphatic hydrocarbon havinq 1-20 carbon atoms includes both linear aliphatic hydrocarbons and branched aliphatic hydrocarbons. Particular examples ot such hydrocarbons include alkyl groups such as methyl, ethyl, n-propy.l , iso-propyl, n-butyl, sec butyl, iso-butyl, tert-butyl, pentyl, hexyl, etc.; alkenyl groups having a double bond, such as styryl; and alkynyl groups having a triple bond, such as acetylene. 24 Non-limiting examples of the compound according to the present invention include the compounds represented by the following formulae 28-760. WO 2OO5/O9O5I2 PCT/KR2O05/00O794 26 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 27 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 29 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 30 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 31 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 32 WO 2005/09051 2 PCT/K R2005/000 794 33 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 34 WO 20O5/O9O5I2 PCT/KR20O5/O0O794 35 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 36 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 37 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 38 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 39 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 40 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 41 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 42 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 43 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 44 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 45 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 46 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 47 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 40 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 49 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 50 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 51 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 52 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 53 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 54 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 55 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 WO 2005/090512 PCT/KR2005/000794 The organic compounds represented by the above formulae may be synthesized from their starting materials through three to eight processing steps. In one embodiment of the synthetic process, the above compounds can be prepared from carbazole. First, carbazole is treated with a halogen atom or halogenated benzene to form a starting material substituted with halogen or halogenated benzene. Next, a compound corresponding to each of A, B, C, D or R1-R10 of the above formula 1 is introduced to the starting material to substitute for the halogen atom of the starting material, thereby forming a desired compound. In the 56 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 process, a catalyst may be used. There is no particular limitation in the selection of a halogen atom. Generally, bromine, chlorine, etc. may be used. It will be appreciated that a suitable synthetic process car. be designed by one skilled in the art with reference to the structural formula of the compound according to the present invention. Synthetic processes for some compounds will be described in the following Fxamples. FIG. ] shows a preferred embodiment of the organic electroluminescence device. The organic compound according to the present invention can be used in at least one organic material layer disposed between an anode and cathode, i.e., at least one layer selected from the group consisting of a hole injection layer, hole transport layer and a light emitting layer. More particularly, the compound can be used in a hole injection layer, hole transport layer, hole injection/hole transport layer, or a hole injection/hole transport/light emitting layer. Meanwhile, it is known that a host material having a large energy gap, for example CBP, is doped with an organic phosphorescent material such as phenylpyridine iridium to provide a high-efficiency device successfully. This indicates that limited efficiency by the singlet-singlet transition may be overcome by triplet-triplet transition. Therefore, when the novel hole injection material according to the present invention is applied as a host material for phosphorescence-based luminescence, it will be possible to obtain an organic, electroluminescence device having significantly improved luminous efficiency and lifespan 57 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 (C. Adachi, M. A. Baldo, and 3. R. Forrest, Applied Physics Latter, 77, 904, 2000., C. Adachi, M. A. Baldo, S. R. Forrest, S. Lama risky, M. F,. Thompsom, and R. C. Kwong, Applied Physics hotter, 78, 1622, 2001). According to the present invention, the organic electroluminescence devices comprising the compounds represented by the above formulae 1-3 and 28-260 in organic material layers can provide significantly improved efficiency and lifespan and show excellent stabili ty. Best Mode for Carrying Out the Invention Hereinafter, synthetic processes of the organic-compound represented by the above formula 1 and manufacture of organic electroluminescence devices using the same will be described in more detail through Examples and Comparative Examples. It is to be understood that the following examples are illustrative only and the present invention is not limited thereto. 58 In order to prepare the compound represented by the above formula 1, the compounds represented by the following formulae a-h may be used as starting materials. WO 2OO5/O9O5I2 PCT/KR2O05/00O794 In the above formulae a-h, X represents a halogen atom. There is no particular limitation in the selection of a halogen atom. In the following examples, the compounds represented by formulae a-h wherein X is Br are selected as starting materials. The starting materials are prepared according to the following Preparation Examples 1 to 8. Carbazole (5.00 g, 29,9 mmol), l-bromo-4-iodobenzene (9.30 g, 32.9 mmol), K2CO3 (16.5 g, 120 59 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 mmol), Cu (3.80 g, 59.8 mmol) and 18-crown-6 (0.40 q, 1.49 mmol.) were refluxed in 50 ml of o-dichlorobenzene for 15 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and the precipitate was filtered off. The filtrate was washed with water three times, dried over MgSO4 and concentrated under reduced pressure. The reaction mixture was purified by column chromatoqraphy to obtain the compound represented by formula a as starting material (5.85 q, 61%). 1H NMR (300 MHz, CDC13) 8.13-8.11(d, 2H), 7.71-7.69(d, 2H) , 7.44-7.21(m, BH); MS [MtH] 322. Carbazole (5.00 g, 29,9 mmol), l-bromo-3-iodobenzene (9.30 g, 32.9 mmol), K2CO3 (16.5 g, 120 mmol), Cu (3.80 g, 59.8 mmol) and 18-crown-6 (0.40 g, 1.49 mmol) were refJuxed in 50 ml of o-dichiorobenzene for 15 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and the precipitate was filtered off. The filtrate was washed with water three times, dried over MgSO4 and concentrated under reduced pressure. The reaction mixture was purified by column chromatography to obtain the compound represented by formula b as starting material (5.85 g, 61%). MS[M+H] 322. The starting material represented by formula a (1.50 g, 4.66 mmol) was dissolved in dimethyl formaide (DMF, 20 ml) and N-bromosuccinimide (NBS, 1.82 g, 10.2 mmol) was added thereto. The reaction mixture was reacted at 50-60 0C for 2 hours and water (15 ml) was 60 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 added thereto. The resultant: precipitate was filtered, washed with water and then recrystabized in dichloromethane/n-hcxane to obtain the compound represented by formula c as start: ing material (1.93 q, 86%). 1H NMR(300 MHz, CDC13) 8.17 (s, 2rl), 7.75-7.74 (d, 2H), 7.51-7.48(d, 2H), 7. 38-7. 35 (d, 2H) , 7.22-7.19(d, 2H); MS [M+H] 178. The starting material represented by formula b (1.50 g, 4.66 mmol) was dissolved in dimethylformaide (DMF, 20 ml) and N-bromosuccinimide (NBS, 1.82 g, 10.2 mmol) was added thereto. The reaction mixture was reacted at 50-60°C for 2 hours and water (15 ml) was added thereto. The resultant precipitate was filtered, washed with water and then recrystallized in dichloromethane/n-hexane to obtain the compound represented by formula d as starting material (1.93 g, 86%). MS[M+H] 478. 2,5-dibromonitrobenzene (12.0 g, 42.1 mmol) was dissolved in dimethylformamide (DMF, 80 ml), Cu (6.0 g, 93.94 mmol) was added thereto, and then the reaction mixture was reacted at 120°C for 3 hours. The reaction mixture was cooled to room temperature, the insoluble material was filtered off and the filtrate was concentrated. The resultant product was recrystallized in ethanol to obtain 4, 4' -dibromo-2,2'-dinitrobiphenyl (10.2 g, 60%). MS[M+] 354. 4,4'-dibromo-2,2'-dinitrobiphenyl (6.1 g, 15.17 mmol) was stirred in HC1 30 ml/EtOH 75 ml, Sn powder 61 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 (7.2 g, 60.68 mmol) was added thereto, and then the reaction mixture was refluxed for 24 hours. Next, the reaction mixture was cooled to room temperature, neutralized with 105 NaOH solution, and then recrystallixed in ethanol to obtain 4 , 4 ' -dibromo-2, 2' -diaminobiphenyl (3.5 q, 67%). MS[M+H] 341. 4, 4' -dibromo-2, 2'-diami nobiphenyJ (3.5 g, 10.23 mmol) was dissolved in phosphoric acid and heated at 1900C for 24 hours. The reaction mixture was cooled to room temperature and then NaHCO3 (aq) was qradually added thereto to form a solid. Then, the solid was filtered to obtain 2, 7-dibromocarbazole (2.2 g, 66%), the compound represented by formula e. MS[M+] 323. 3, 6-dibromocarbazole (1.63 g, 5.00 mmol), 4- bromophenylboronic acid (2.95 g, 15.0 mmol), 2M potassium carbonate solution (10 ml) and tetrakis(triphenylphosphine)palladium (29.0 mg, 0.25 mmol) were added to 100 ml of THF. The reaction mixture was stirred under reflux for about 24 hours and then cooled to room temperature. Next, the reaction mixture was introduced into toluene and brine and the toluene layer was separated. The separated layer was dried over MgSO4, filtered and concentrated. Then, the reaction mixture was purified by column chromatography to obtain the compound represented by formula f as starting material (1.15 q, 48%). 1H NMR(300 MHz, CDC13) 10.1(s, 1H), 7.77(s, 2H), 7.49-7.46(m, 6H), 7.37(d, 4H), 7.30(d, 2H) ; MS [M+H] 476. 62 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 The compound tepresented by formula f (1.13 g, 3.00 mmol) , l-bromo-4-iodobenzene (1.87 q, 6.60 mmol), K2CO3 (3.32 g, 24 mmol), Cu (0.76 g, 12.0 mmol) and 18-crown-6 (0.08 q, 0.30 mmol) were refluxed in 10 ml of o-di chlorobenzene Cor 15 hours. Aft.er the completion of the reaction, the reaction mixture was cooled to room temperature and the precipitate was filtered off. The filtrate was washed with water three times, dried over MgSO4 and concentrated under reduced pressure. The reaction mixture was purified by column chromatography to obtain the compound represented by formula g as starting material (1.02 g, 54%). lH NMR (300 MHz, CDCl3) 7.77(s, 2H), 7.49-7.40(m, 8H), 7.37(d, 4H), 7.30(d, 2H) , 7.20 (d, 211) ; MS [M+H] 630. The compound represented by formula c (2.40 g, 5.00 mmol), 4-bromophenylboronic acid (3.94 g, 20.0 mmol), 2M potassium carbonate solution (20 ml) and tetrakis (triphenylphosphine) palladium (58.0 mg, 0.50 mmol) were added to 100 ml of THF. The reaction mixture was stirred under reflux for about 24 hours and then cooled to room temperature. Next, the reaction mixture was introduced into toluene and brine and the toluene layer was separated. The separated layer was dried over MgSO4, filtered and concentrated. Then, the reaction mixture was purified by column chromatography to obtain the compound represented by formula h as starting material (2.09 g, 59%). 1H NMR (300 MHz, CDC13) 7.77 (s, 2H) , 7.50-7.46(m, 10H) , 7.37 (m, 6H), 7. 30 (m, 4H) ; MS [M+H] 706. 63 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 represented by formula 61 The compound represonted by formula c (1.00 g, 2.08 mmol), diphonylamine (1.16 g, 6.86 mmol), Pd2(dba)3 (0.125 g, 0.13 mmol), P(t-Bu)1 (0.04 g, 0.2 rrjnol) and sodium tert--butoxide (1.80 g, 18.7 mmol) were added to xylene (40 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution or THF and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystal1ized in ethyl acetate/n-hexane to obtain the compound represented by formula 61 (1.16 g, 75%). 1H NMR (300 MHz, CDC13) 6.78 (d, 2H), 6.96(m, 14H) , 7.12(m, 611), 7.25(s, 2H), 7.5-7.51(m, 14H), 7.65(d, 2H); MS [M+HJ 745. The compound represented by formula c (1.00 g, 2.08 mmol), N-phenyl-1-naphthylamine (1.50 g, 6.86 mmol), Pd2(dba)3 (0.125 g, 0.13 mmol), P(t-Bu)3 (0.04 g, 0.2 mmol) and sodium tert—butoxide (1.80 g, 18.7 mmol) were added to xylene (4 0 ml) and the mixture was refluxed for about 3 hours . After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystallized in ethyl acetate/n-hexane to obtain the compound represented by formula 62 (1.46 g, 79%). 1H NMR (300 MHz, CDC13) 6.78 (dr 2H) , 6.96-7.12(m, 14H) , 7.25(s, 2H) , 7 . 5-7 . 51 (m, 8H) , 64 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 7. 65-7. 66 (m, 8H) , 7 . 80- 7 . 81 (m, 511), 8. 11-8. 12 (m, 6H); MS [M+H] 895. The compound represented by formula c (1.00 q, 2.08 mmol), N-phenyl-2-naphthy lamine (1.50 g, 6.06 mmol), Pd2(dba) (0.125 g, 0.13 mmol), P(t-Bu) (0.04 q, 0.2 mmol) and sodium ter t-butoxide (1.80 q, 18.7 mmol) were added to xylenc (40 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystallized in ethy] acetate/n-hexane to obtain the compound represented by formula 63 (1.21 g, 65%). 1H NMR (300 MHz, CDC13) 6.78(d, 2H), 6.96-7.0(m, 8H) , 7.12(m, 3H), 7.25-7.29(m, 8H) , 7.51-7.73(m, 1.6H) , 7.94-8.05(m, 9H) ; MS [M+H] 895. The compound represented by formula c (1.00 g, 2.08 mmol), N-phenyl- (9-phenanthrenyl) amine (1.8b g, 6.86 mmol), Pd2(dba)3 (0.125 g, 0.13 mmol), P(t-Bu)3 (0.04 g, 0.2 mmol) and sodium tert-butoxide (1.80 g, 18.7 mmol) were added to xylene (40 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystallized in ethyl 65 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 acetate/n-hexane to obtain the compound represented by formula 64 (0.93 g, 43%). 1H NMR (300 MHz, CDCl3) 6.70(d, 2H), 6.96-6.97(m, 8H), 7.12(t, 3H) , 7.25(s, 2H) , 7.41(m, 3H), 7.5-7.51(m, 8H) , 7.65(d, 211), 8. 32-8. 38 (m, 12H), 8.62(d, 6H), 9.43(m, 611) ; MS [M+H] 1045. The compound represented by formula c (1.00 g, 2.08 mmol), N-phenyl-(9-anthrcny1)amine (1.85 g, 6.86 nunol), Pd2(dba)3 (0.125 g, 0.33 mmol), P(t-Bu)3 (0.04 g, 0.2 mmol) and sodium tert-butoxi de (3 .80 g, 18.7 mmol) were added to xylene (40 ml) and the mixture? was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystallized in ethyl acetate/n-hexane to obtain the compound represented by formula 65 (1.24 g, 57%). 1H NMR (300 MHz, CDC13) 6.78(d, 2H), 6.96-6.6.98 (m, 8H) , 7.12(t, 3H), 7.23(s, 2H), 7.5-7.51 (m, 8H) , 7.65-7.66(m, 7H) , 7.81-7.84(m, 10H), 8.14-8.15(m, 12H) ; MS [M+H] 1045. The compound represented by formula c (1.00 g, 2.08 mmol), di-(1-naphthyl)amine (1.85 g, 6.86 mmol), Pd2(dba)3 (0.125 g, 0.13 mmol), P(t-Ru)3 (0.04 g, 0.2 mmol) and sodium tert-butoxide (1.80 g, 18.7 mmol) were added to xylene (40 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and 66 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 added to a mixed solution of THF and H2O . The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystallized in ethyl acetate/n-hexane to obtain the compound represented by formula 68 (1.04 g, 48%). 'H NMR (300 MHz, CDC13) 6.78(d, 2H), 7.0-7.05(m, 8H) , 7.25(s, 2H) , 7.50-7.66(m, 16H), 7.80-7.81(m, 12M) , 8 . 11-8 . 16 (rn, 12H) ; MS [M+H] 1045. The compound represented by formula c (1.00 g, 2.08 mmol), d: - (2-naphthyl) amine (1.85 g, 6.86 mmol), Pd2(dba)3 (0.125 g, 0.13 mmol), P(t-Bu)3 (0.04 g, 0.2 mmol) and sodium tert-butoxide (1.80 g, 18.7 mmol) were added to xylene (40 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystallized in ethyl acetate/n-hexane to obtain the compound represented by formula 69 (0.89 g, 41%). 1H NMR (300 MHz, CDC13) 6.78(d, 2H), 7.0(d, 2H), 7.26-7.29(m, 14H), 7.5-7.53(m, 16H) , 7.94-8.05(m, 18H);MS [M+H] 1045. The compound represented by formula c (1.50 g, 3.13 mmol), p,p'-ditolylamine (2.03 g, 10.3 mmol), Pd2(dba)3 (0.19 g, 0.21 mmol), P(t-Bu)3 (0.06 g, 0.31 mmol) and sodium tert-butoxide (1.05 g, 10.96 mmol) were added to xylene (30 ml) and the mixture was refluxed for 67 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 about 3 hours. After the completion of The reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THE' and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystalized in ethyl acetate/n-hexane to obtain the compound represented by formula 71 (1.31 g, 50%). 1H NMR (300 MHz, CDCl3) 2.5 5 (s, 18H), 6.48-6.70(m, 1 611) , 6.95 - 7 .01 (m, 14H), 7.2-7.35 (m, 4H); MS [M+H] 82 9. The compound represented by formula c (1.5O g, 3.13 mmol), m, m' -ditolylamine (1.96 ml, 10.3 mmol), Pdr(dba)3 (0.19 g, 0.21 mmol), P(t-Bu)3 (0.06 g, 0.31 mmol) and sodium tert-butoxide (1.05 g, 30.96 mmol) were added to xylene (30 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was coo led to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, ciried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystallized in ethyl acetate/n-hexane to obtain the compound represented by formula 72 (1.55 g, 60%). 1H NMR (300 MHz, CDC13) 2.55(s, 18H), 6.48-6.70(m, 16H), 6 .95-7.01 (m, 14H) , 7.2-7.35(m, 4H); MS [M+H] 829. The compound represented by formula c (1.5O g, 3.13 mmol), 3-methyldiphenylamine (1.88 g, 10.3 mmol), Pd2(dba)3 (0.19 g, 0.21 mmol), P(t-Bu)3 (0.06 g, 0.31 68 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 mmol) and sodium tert-butoxide (1.05 g, 10.96 mmol) were added to xylene (30 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic-layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystal li.zed in ethyl acetate/n-hexane to obtain the compound represented by formula 89 (1.62 g, 66';). MS[M+H] 787. The compound represented by formula c (1.50 g, 3.13 mmol), N-(3-methylphenyl)-1-naphthylamine (2.40 g, 10.3 mmol), Pd2(dba)T (0.19 g, 0.21 mmol), P(t-Bu)3, (0.06 g, 0.31 mmol) and sodium tert-butoxidc (1.05 g, 10.96 mmol) were added to xylene (30 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product, was purified by column chromatography and recrystallized in ethyl acetate/n-hexane to obtain the compound represented by formula 95 (1.92 g, 65%). MS[M+H] 937. The compound represented by formula c (1.50 g, 3.13 mmol), N-(4-methylphenyl)-1-naphthylamine (2.40 g, 10.3 mmol), Pd2(dba)3 (0.19 g, 0.21 mmol), P(t-Bu)3 (0.06 g, 0.31 mmol) and sodium tert-butoxide (1.05 g, 10.96 mmol) were added to xylene (30 ml) and the mixture was 69 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 refluxed for about 3 hours. After the; completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H20. The organic layer was separated, ciried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystallized in ethyl acetate/n-hexane to obtain the convpound represented by formula 96 (1.92 g, 65%). MS[M+H] 937. The compound represented by formula c (1.50 g, 3.13 mmol), N- (3-methylpher.y.l ) -2-na phthylamine (2.40 g, 10.3 mmo]), Pd2(dba)3 (0.19 g, 0.21 mmol), P(t-Bu)3 (0.06 g, 0.31 mmol) and sodium tert-butoxide (3.05 g, 1O.96 mmol) were added to xylene (30 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, ciried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystallized in ethyl acetate/n-hexane to obtain the compound represented by formula 101 (1.92 g, 65%). MS[M+HJ 9 37. The compound represented by formula c (1.50 g, 3.13 mmol), N- (4-methylphenyl) -2-naphthylamine (2.40 g, 10.3 mmol), Pd2(dba)3 (0.19 g, 0.21 mmol), P(t-Bu)3 (0.06 g, 0.31 mmol) and sodium tert-butoxide (1.05 g, 10.96 mmol) were added to xylene (30 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room 70 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystallized in ethyl acetate/n-hexane to obtain the compound represented by formula 102 (1.92 g, 65%). MS[M+H] 937. The compound represented by formula d (1.00 g, 2.08 mmol), diphenylaminc (1.16 g, 6.86 mmol), Pd2(dba)3 (0.125 g, 0.13 mmol), P(t-Bu)3 (0.04 g, 0.2 mmol) and sodium tert-butoxide (1.80 g, 10.7 mmol) were added to xylene (40 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystallized in ethyl acetate/n-hexane to obtain the compound represented by formula 113 (1.16 g, 75%). MS[M+H] 745. The compound represented by formula d (1.00 g, 2.08 mmol), N-phenyl-1-naphthylamine (1.50 g, 6.86 mmol), Pd2(dba)3 (0.125 g, 0.13 mmol), P(t-Bu)3 (0.04 g, 0.2 mmol) and sodium tert-butoxide (1.80 g, 18.7 mmol) were added to xylene (40 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over MgSO4 and 71 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 then concentrated. The rosulant. product was purified by column chromatography and recrystallized in ethy] acetate/n-hexane to obtain the compound represented by formula 114 (1.-16 q, 79%). MS[M+H] 895. The compound represented by formula d (1.00 q, 2.08 mmol), N-phenyl-2-napht hylarni.ne (1.50 g, 6.86 mmol), Pd2(dba)3 (0.125 g, 0.1.3 mmol), P(t.-Bu) 3 (0.04 g, 0.2 mmol) and sodium tert-butoxide (1.80 g, 18.7 mmol) were added to xylene (40 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of TUF and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystallir.od in ethyl acetate/n-hexane to obtain the compound represented by formula 115 (1.21 g, 65%). MS[M+H1 895. The compound represented by formula d (1.50 g, 3.13 mmol), 3-methyldiphenyl.ami ne (1.88 g, 10.3 mmol), Pd2(dba)3 (0.19 g, 0.21 mmol), P(t-Bu)3 (0.06 g, 0.31 mmol) and sodium tert-butoxide (1.05 g, 10.96 mmol) were added to xylene (30 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystallized in ethyl 72 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 acetate/n-hexane to obtain the compound represented by formula 1.16 (1.62 q, 66%). MS[M + H] 737. The compound represented by formula d (1.50 g, 3.13 mmol), N- ( 3-methy1phenyl) -1-naphthylamine (2.40 g, 10.3 mmol), Pd2(dba)3 (0.19 g, 0.21 mmol), P(t.Bu)3 (0.06 g, 0.31 mmol) and sodium tert-butoxide (1.05 q, 10.96 mmol) were added to xyleno (30 ml) and the mixture was refluxed for about. 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystallized in ethyl acetate/n-hexane to obtain the compound represented by formula 120 (1.92 g, 6b%). MS[M+H] 937. The compound represented by formula d (1.50 g, 3.13 mmol), N-(3-methylphenyl)-2-naphthylamine (2.40 g, 10.3 mmol), Pd2(dba)3 (0.19 g, 0.21 mmol), P(t-Bu)3 (0.06 g, 0.31 mmol) and sodium tert-butoxide (1.05 g, 10.96 mmol) were added to xylene (30 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystallized in ethyl acetate/n-hexane to obtain the compound represented by formula 121 (1.92 g, 65%). MS[M+H] 937. 73 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 1) The compound represented by formula e (5.0 g, 15.38 mmol) and di-tert-buty l.-dicarbonate (5.04 g, 23.08 mmol) wore dissolved i.n 50 ml of THF and 4- (dimethylamino) pyridine (0.19 g, 1.54 mmol) was added thereto. Then, the reaction mixture was reacted at room temperature for 24 hours. After the completion of the reaction, the reaction mixture was concentrated and recrystallized in ethanol to obtain a product (6.16 g, 94%) 2) The product obta from from step 1) (6.16 g, 14.4 9 mmol), diphenylamine (5.89 g, 34.78 mmol), sodium tert-butoxide (4.18 g, 43.47 mmol), Pd2(dba)3 (0.17 g, 0.29 mmol) and P(t-Bu)3 (0.06 g, 0.29 mmol) were added to xylene (30 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystallized in ethyl acetate/n-hexane to obtain a compound (5.88 g, 67%). 3) The compound obtained from step 2) (5.88 g, 9.77 mmol) was dissolved in trifluoroacetic acid/chloroform = 50 ml/50 ml and the solution was refluxed for 3 hours. The reaction mixture was cooled to room temperature, quenched with aqueous NaOH solution, extracted with methylene chloride (MC) and then washed with water many times. The resultant product was dried over magnesium sulfate and allowed to evaporate. The crude product was purified by column chromatography 74 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 (ethyl acetate/hexane - 1/9) to obtain a compound (.2.9 g, 59%). 4) The product, obtained from step 3) (2.9 g, 5.78 mmol), 4-bromophenyl-diphenylaminc (1.36 g, 4.21 mmol), Pd2(dba)3 (0.05 g, 0.084 mmol ) and P(t-.-Bu)3 (0.017 g, 0.084 mmol) and sodium tert-butoxide (1.21 g, 12.63 mmol) were added to xylene (30 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over. MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystallized in ethyl acetate/n-hexane to obtain the compound represented by formula 192 (1.5 g, 49%). MS[M+H] 745. 1) The compound represented by formula e (5.0 g, 15.38 mmol) and di-tert-butyl-dicarbonate (5.04 g, 23.08 mmol) were dissolved in 50 ml of THF and 4- (dimethylamino)pyridine (0.19 g, 1.54 mmol) was added thereto. Then, the reaction mixture was reacted at room temperature for 24 hours. After the completion of the reaction, the reaction mixture was concentrated and recrystallized in ethanol to obtain a product (6.16 g, 94%) . 2) The product obtained from step 1) (6.16 g, 14.49 mmol), N-phenyl-1-naphthylamine (7.63 g, 34.78 mmol), sodium tert-butoxide (4.18 g, 43.47 mmol), Pd2(dba)3 (0.17 g, 0.29 mmol) and P(t-Bu)3 (0.06 g, 0.29 mmol) were added to xylene (30 ml) and the mixture was refluxed for about 3 hours. After the completion of the 75 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H20. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystal1ized in ethyl acetate/n-hexane to obtain a compound (6.0 g, 59%). 3) The compound obtained from step 2) (6.0 g, 8.54 mmol) was dissolved in trifluoroacetic: acid/chloroform - 50 ml/50 ml and the solution was refluxed for 3 hours. The reaction mixture was cooled to room temperature, quenched with aqueous NaOH solution, extracted with methylene chloride and then washed with water many times. The resultant product was dried over magnesium sulfate and allowed to evaporate. The crude product was purified by column chromatography (ethyl acetate/hexane = 1/9) to obtain a compound (3.8 g, 7-1?.). 4) The product obtained from step 3) (3.8 g, 6.31 mmol), 4-bromophenyl-N-pheny 1.-1-naphthyiamine (1.57 g, 4.21 mmol), Pd2(dba)3 (0.05 g, 0.084 mmol) and P(t-Bu)3 (0.017 g, 0.084 mmol) and sodium tert-butoxide (1.21 g, 12.63 mmol) were added to xylone (30 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystallized in ethyl acetate/n-hexane to obtain the compound represented by formula 193 (1.2 g, 32%). MS[M+H] 895. 1) The compound represented by formula e (5.0 g, 76 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 15.38 mmol) and di-tert-butyl-dicarbonate (5.04 q, 23.08 mmol) were dissolved in bO ml of THF and 4-(dimethylamino) pyridine (0.19 g, 1.54 mmol) was added thereto. Then, the reaction mixture was reacted at room temperature for 24 hours. Alter the completion of the reaction, the reaction mixture was concentrated and recrysta1lized in ethanol to obtain a product (6.16 g, 94%) . 2) The product obtained from step 1) (6.16 q, 14.4 9 mmol), N-phenyl-2-naphthylamine (7.63 g, 34.78 mmol), sodium tert-butoxide (4.18 g, 43.4 mmol), Pd2(dba)3 (0.17 g, 0.29 mmol) and P(t-Bu)3 (0.06 g, 0.29 mmol) were added to xylene (30 ml ) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatoqraphy and recrystallized in ethyl acetatc/n-hexane to obtain a compound (6.0 g, 59%). 3) The compound obtained from step 2) (6.0 g, 8.54 mmol) was dissolved in trifluoroacetic acid/chloroform - 50 ml/50 ml and the solution was refluxed for 3 hours. The reaction mixture was cooled to room temperature, quenched with aqueous NaOH solution, extracted with methylene chloride and then washed with water many times. The resultant product was dried over magnesium sulfate and allowed to evaporate. The crude product was purified by column chromatography (ethyl acetate/hexane = 1/9) to obtain a compound (3.8 g, 74%). 4) The product obtained from step 3) (3.8 g, 6.31 mmol), 4-bromophenyl-N-phenyl-2-naphthylamine (1.57 g, 77 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 4.21 mmol), Pd2(dba)3. (0.05 g, 0.084 mmol ) and P(t-Bu)3 (0.017 g, 0.084 mmol) and sodium tert-butoxide (1.21 g, 12.63 mmol) were added to xylone (30 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over MgSO4, and then concentrated. The resultant product was purified by column chromatography and recrystallized in ethyl acetate/n-hexane to obtain, the compound represented by formula 194 (1.2 g, 321). MS[M+H] 895. 1) The compound represented by formula e (5.0 g, 15.38 mmol) and di-tert-butyl-dicarbonate (5.04 g, 23.08 mmol) were dissolved in 50 ml of THF and 4-(dimethylamino)pyridine (0.19 g, 1.54 mmol) was added thereto. Then, the reaction mixture was reacted at room temperature for 24 hours. After the completion of the reaction, the reaction mixture was concentrated and recrystallized in ethanol to obtain a product (6.16 g, 94%) . ?,) The product obtained from step 1) (6.16 g, 14.49 mmol), 3-methyl-diphenylamine (6.37 g, 34.78 mmol), sodium tert-butoxide (4.18 g, 43.47 mmol), Pd2(dba)3 (0.17 g, 0.29 mmol) and P(t-Bu)3 (0.06 g, 0.29 mmol) were added to xylene (30 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by 78 WO 2005/090512 PCT/KR20O5/000794 column chrematography and recrystallized in ethyl acetate/n-hexane to obtain a compound (6.3 g, 69%). 3) The compound obtained from step 2) (6.3 g, 10.0 mmol) was dissolved in trifluoroncetic acid/chloroform - 50 ml/50 ml and the solution wan retluxed for 3 hours. The reaction mixture was cooled to room temperature, quenched with aqueous NaOH solution, extracted with methyleno chloride and then washed with water many times. The resultant product was dried over magnesium sulfate and allowed to evaporate. The crude product was purified by column chromatography (ethyl acetate/hexane = 1/9) to obtain a compound (3.B g, 71%) . 4) The product obtained from step 3) (3.8 g, 7.17 mmol), 4-bromophenyl-(3-methyl)-diphenylamine (1.42 q, 4.21 mmol), Pd2(dba)3 (0.05 g, 0.084 mmol) and P(tBu)3 (0.017 g, 0.084 mmol) and sodium tert-butoxide (1.21 g, 12.63 mmol) were added to xylene (30 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystallized in ethyl acetate/n-hexane to obtain the compound represented by formula 197 (1.2 g, 36%). MS[M+H] 787. 1) The compound represented by formula e (5.0 g, 15.38 mmol) and di-tert-butyl-dicarbonate (5.04 g, 23.08 mmol) were dissolved in 50 ml of THF and 4- (dimethylamino) pyridine (0.19 g, 1.54 mmol) was added thereto. Then, the reaction mixture was reacted at room 79 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 temperature Cor 24 hour . After the completion of the reaction, the reaction mixture was concentrated and recrystallized in ethanol to obtain a product (6.16 g, 94% ) . 2) The product obtained from step .1 ) (6.1G q, 14. 49 nuno1) , diphenylamine (5.89 g, 34.78 mmol), sodium tert-butoxide (4.18 g, 43.47 mmol), Pd7(dba)3 (0.17 g, 0.2 9 mmol) and P(t-Bu), (0.06 g, 0.29 mmol) were added to xylene (30 ml) and the mixture was refluxed for about 3 hours. After the completion of. the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and rec.rystall.ized in ethyl acetate/n-hexane to obtain a compound (5.88 g, 67%). 3) The compound obtained from step 2) (5.88 g, 9.77 mmol) was dissolved in trifluoroacetic acid/chloroform = 50 ml/50 ml and the solution was refluxed for 3 hours. The reaction mixture was cooled to room temperature, quenched with aqueous NaOH solution, extracted with methylene chloride and then washed with water many times. The resultant product was dried over magnesium sulfate and allowed to evaporate. The crude product was purified by column chromatography (ethyl acetate/hexane - 1/9) to obtain a compound (2.9 g, 59%). 4) The product obtained from step 3) (2.9 g, 57.8 mmol), 4-bromophenyl-N-phenyl-l-naphthylamine (1.57 g, 4.21 mmol), Pd?(dba)3 (0.05 g, 0.084 mmol) and P(t-Bu)3 (0.017 g, 0.084 mmol) and sodium tert-butoxide (1.21 g, 12. 63 mmol) were added to xylene (30 ml) and the mixture was refluxed for about 3 hours. After the completion of 80 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H?0. The organic Layer was separated, dried over MgSO4 and then concentrated. The resultant product, was purified by column chromatography and recrystallized in ethyl acetate/n-hexane to obtain the compound represented by formula 218 (1.5 g, 49%). MS[M+H] 795. 1) The compound represented by formula e (5.0 q, 15.38 mmol) and di-tert-butyl-dicarbonate (5.04 g, 23.08 mmol) were dissolved in 50 ml of THF and 4- (dimethylamino)pyridine (0.19 g, 1.54 mmol) was added thereto. Then, the reaction mixture was reacted at room temperature for 24 hours. After the completion of the reaction, the reaction mixture was concentrated and recrystallized in ethanol to obtain a product (6.16 g, 94%) . 2) The product obtained from step 1) (6.16 g, 14.49 mmol), N-phenyi-2-naphthylamine (7.63 g, 34.78 mmol), sodium tert-butoxide (4.18 g, 43.47 mmol), Pd2(dba)3 (0.17 g, 0.29 mmol) and P(t-Bu)3 (0.06 g, 0.29 mmol) were added to xylene (30 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product was purified by column chromatography and recrystallized in ethyl acetate/n-hexane to obtain a compound (6.0 g, 59%). 3) The compound obtained from step 2) (6.0 g, 8.54 mmol) was dissolved in trifluoroacetic acid/chloroform = 81 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 50 ml/50 ml and the solution was refluxed tor 3 hours. The reaction mixture was cooled to room temperature, quenched with aqueous NaOH solution, extracted with methylene chloride and then washed with water many times. The resultant product was dried over maqnesium sulfate and allowed to evaporate. The crude product: was purified by column chromatography (ethyl acetate/hexane = 1/9) to obtain a compound (3.8 g, 74%). 4) The product obtained from step 3) (3.8 g, 6.31 mmol), 4-bromophenyl-N-phenyl-l-naphthylamine (1.57 g, 4.21 mmol), Pd2(dba)3 (0.05 g, 0.084 mmol) and P(t-Bu).-, (0.017 g, 0.084 mmol) and sodium tert-butoxide (1.21 g, 12.63 mmol) were added to xylene (30 ml) and the mixture was refluxed for about 3 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and H2O. The organic layer was separated, dried over MgSO4 and then concentrated. The resultant product; was purified by column chromatography and recrystallized in ethyl acetate/n-hexane to obtain the compound represented by formula 219 (1.2 g, 32%). MS[M+H] 895. The compound represented by formula c (1.00 g, 2.08 mmol), triphenylamine-4-boronic acid (1.99 g, 6.87 mmol), 2M potassium carbonate solution (10 ml) and tetrakis (triphenylphosphine) palladium (0.07 g, 0.06 mmol) were added to 40 ml of THF. The mixture was stirred under reflux for about 24 hours and then cooled to room temperature. The reaction mixture was added to toluene/brine, and then the toluene layer was separated, dried over MgSO4, filtered and concentrated. The 82 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 resultant product was purified by column chromatography and recrystallized in ethyl acetate/n-hexane to obtain the compound represented by formula 252 (1.15 g, 55%). lH NMR (300 MHz, COCl3) 6.76-6.82(m, 18H), 6. 92-6. 95 (m, 6H) , 7.31-7.35(m, 12H), 7.53-7.60(m, 10H), 7.76-9.07(m, 6H); MS [M+H] 973. A glass substrate on which a thin film of ITO (indium tin oxide) was coated to a thickness of 1000A was immersed in distilled water containing a detergent to wash the substrate with ultrasonic waves. The detergent was a product commercially available from Fisher Co. The distilled water has been filtered twice by using a filter commercially available from Millipore Co. After washing ITO for 30 minutes, washing with ultrasonic waves was repeated twice for 10 minutes by using distilled water. After the completion of washing with distilled water, washing with ultrasonic waves was carried out by using isopropyl alcohol, acetone and methanol, in turn. The resultant substrate was dried and transferred to a plasma cleaner. Then, the substrate was cleaned for 5 minutes by using oxygen plasma and transferred to a vacuum deposition device. On the ITO transparent electrode (first electrode) prepared as described above, the compound represented by the above formula 61 was coated to a thickness of 600A by thermal vacuum deposition, thereby forming a hole injection layer. Next, NPB as a hole transport material was coated thereon to a thickness of 400A by vacuum deposition. Additionally, Alq3, which serves as light emitting/electron injection/electron transport material 83 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 was coated theieon to a thickness of 500A by vacuum deposition to complete the formation of a thin film of organic materials. On tho A.]q3 layer, Lithium fluoride (LiF) and aluminum were sequentially vacuum-deposited to a thickness of l5)A and 2500A, respectively, to form a cathode (second electrode). In the above process, deposition rate of each orqanic material was maintained at C.5-1.0 A/sec and deposition rates of lithium fluoride and aluminum were maintained at 0.2 A/sec and 2-3 A/sec, respectively. The resultant orqanic electroluminescence device showed a spectrum havinq a luminance of 3.87 cd/A under the application of a forward electric field with a drive voltage of 7.17V at a current density of .100 mA/cm2. On the ITO transparent electrode prepared as described in Example 28, the compound represented by the above formula 62 was coated t.o a thickness of 800A by thermal vacuum deposition , thereby forming a hole injection layer. Next, NPB as a hole transport material was coated thereon to a thickness of 400A by vacuum deposition. Additionally, A.lq3, which serves as light emitting/electron injection/electron transport material was coated thereon to a thickness of 300A by vacuum deposition to complete the formation of a thin film of organic materials. The remaining procedure was the same as Example 28. The resultant organic electroluminescence device showed a spectrum having a luminance of 3.8 6 cd/A under the application of a forward electric field with a drive voltage of 7.8V at a current density of 100 mA/cm2. 84 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 Example 28 was repeated to manufacture an organic electroluminescence device, except that the compound represented by the above formula 63 was used instead of: the compound represented by the above formula 61. The resuJtant organic electroluminescence device showed a spectrum having a luminance of 3.8 cd/A under the application of a forward electric field with a drive voltage of 7.8V at a current density of 100 mA/cm2. Example 28 was repeated to manufacture an organic electroluminescence device, except that the compound represented by the above formula 64 was used instead of the compound represented by the above formula 61. The resultant organic electroluminescence device showed a spectrum having a luminance of 3.61 cd/A under the application of a forward electric field with a drive voltage of 8.1V at a current density of 100 mA/cm2. Example 28 was repeated to manufacture an organic electroluminescence device, except that the compound represented by the above formula 69 was used instead of the compound represented by the above formula 61. The resultant organic electroluminescence device showed a spectrum having a luminance of 3.82 cd/A under the application of a forward electric field with a drive voltage of 8.0V at a current density of 100 mA/cm2. 85 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 Example 28 was repeated to manufacture an organic electroluminescence device, except that the compound represented by the above formula 71 was used instead of the compound represented by the above formula 61. The resultant organic electroluminescence device showed a spectrum having a luminance of 4.4 cd/A under the application of a forward electric field with a drive voltage of 7.6V at a current density of 100 mA/cm2. Example 28 was repeated to manufacture an organic electroluminescence device, except that the compound represented by the above formula 72 was used instead of the compound represented by the above formula 61. The resultant organic electrolumainescence device showed a spectrum having a luminance of 4.15 cd/A under the application of a forward electric field with a drive voltage of 7.8V at a current density of 100 mA/cm2. Example 28 was repeated to manufacture an organic electroluminescence device, except that the compound represented by the above formula 89 was used instead of the compound represented by the above formula 61. The resultant organic electroluminescence device showed a spectrum having a luminance of 4.3 cd/A under the application of a forward electric field with a drive voltage of 7.5 at a current density of 100 mA/cm2. Example 28 was repeated to manufacture an organic electroluminescence device, except that the compound 86 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 represented by the above formula 95 WAS used instead of the compound represented by the above formula 61 . The resultant organic electroluminescence device showed a spectrum having a Luminance of.. 4.5 cd/A under the application of a forward electric field with a drive voltage of 7.3V at a current density of 100 mA/cm2. Example 28 was repeated to manufacture an organic electroluminescence device, except that the compound represented by the above formula 9G was used instead of the compound represented by the above formula 61. The resultant organic electroluminescence device showed a spectrum having a luminance of 4.4 cd/A under the application of a forward electric field with a drive voltage of 7.2V at a current density of 100 mA/cm2. Example 28 was repeated to manufacture an organic electroluminescence device, except that the compound represented by the above formula 113 was used instead of the compound represented by the above formula 61. The resultant organic electroluminescence device showed a spectrum having a luminance of 4.2 cd/A under the application of a forward electric field with a drive voltage of 7.7V at a current density of 100 mA/cm2. Example 28 was repeated to manufacture an organic electroluminescence device, except that the compound represented by the above formula 114 was used instead'of the compound represented by the above formula 61. 87 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 The resultant, organic electroluminescence device showed a spectrum having a luminance of 4.1 cd/A under the application of a forward electric field with a drive voltage of 7.6V at. a current density of 100 mA/cm2. Example 28 was repeated to manufacture an organic electroluminescence device, except that the compound represented by the above formula 120 was used instead of the compound represented by the above formula 61. The resultant organic electroluminescence device showed a spectrum having a luminance of 3.98 cd/A under the application of a forward electric field with a drive voltage of 7.8V at a current density of 100 mA/cm2. On the 1T0 transparent electrode prepared as described in F.xample 28, the compound represented by the above formula 192 was coated to a thickness of 800A by thermal vacuum deposition, thereby forming a hole injection layer. Next, NPB as a hole transport material was coated thereon to a thickness of 300 A by vacuum deposition. Additionally, Alq3, which serves as light emitting/electron injection/electron transport material was coated thereon to a thickness of 300A by vacuum deposition to complete the formation of a thin film of organic materials. The remaining procedure was the same as Example 28. The resultant organic electroluminescence device showed a spectrum having a luminance of 3.7 cd/A under the application of a forward electric field with a drive voltage of 6.7V at a current density of 100 mA/cm2. 88 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 Example 11 war. repeated to manufacture an organic electroluminescence device, except that the compound represented by the above formula 193 was used instead of the compound represented by the above formula 192. The resultant organic electroluminescence device showed a spectrum having a luminance of 3.6 cd/A under the application of a forward electronic field with a drive voltage of 6.9V at a current density of 100 mA/cm2. Example 41 was repeated to manufacture an organic electroluminescence device, except that the compound represented by the above formula 194 was used instead of the compound represented by the above formula 192. The resultant organic electroluminescence device showed a spectrum having a luminance of 3.5 cd/A under the application of a forward electric field with a drive voltage of 6.8V at a current density of 100 mA/cm2. Example 41 was repeated to manufacture an organic electroluminescence device, except that the compound represented by the above formuZLa 197 was used instead of the compound represented by the above formula 192. The resultant organic electroluminescence device showed a spectrum having a luminance of 3.9 cd/A under the application of a forward electric field with a drive voltage of 6.9V at a current density of 100 mA/cm2. 89 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 Example 41 was repeated to manufacture an organic-elect roluminescence device, except that the compound represented by the above formula 218 was used instead of the compound represented by the above formula 192. The resultant organic electroluminescence device showed a spectrum having a Luminance of 3.8 cd/A under the application of a forward electric field with a drive voltage of 6.8V at. a current density of 100 mA/cm2. Example 41 was repeated to manufacture an organic electroluminescence device, except that the compound represented by the above formula 219 was used instead of the compound represented by the above formula 192. The resultant organic electroluminescence device showed a spectrum having a luminance of 3.6 cd/A under the application of a forward electric field with a drive voltage of 6.8V at a current density of 100 mA/cm2. Example 41 was repeated to manufacture an organic electroluminescence device, except that the compound represented by the above formula 252 was used instead of the compound represented by the above formula 192. The resultant organic electroluminescence device showed a spectrum having a luminance of 3.2 cd/A under the application of a forward electric field with a drive voltage of 6.88V at a current density of 100 mA/cm2. As can be seen from the above Examples, the organic electroluminescence device using the compound according to the present invention as a hole injection 90 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 material can provide excellent electroluminescence effect as demonstrated by a luminance of 3.2-4.5 cd/A under a forward electric: field of about 6.88V at. a current density of 100 mA/cm2. In other words, when the compound according to the present invention is used as hole injection material in an organic electroluminescence device comprising NPD as hole transport material, and A.lq3 as light emitting/electron injection/electron transport material, it is possible to improve electroluminescence effect significantly compared to conventional devices. Industrial Applicability As can be seen from the foregoing, novel compounds according to the present invention can rea.li.2e improvements in luminous efficiency and lifespan, when they are used in organic compound layers of an organic electroluminescence (EL) device, which is one of light emitting devices. Therefore, the compound according to the present invention can be advantageously used in the field of electric devices including organic light emitting devices. 91 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 Claims 1. A compound represented by the following formula 1: Rl to R1O are the same or different and each comprises, only once or repeatedly at least two times, at least one selected from the group consisting of a hydrogen atom; aliphatic hydrocarbon having 1-20 carbon atoms; aromatic hydrocarbon non-substituted or substituted with a nitro, nitrile, halogen, alkyl, alkoxy or amino group; silicon group having an aromatic substituent; heterocyclic aromatic hydrocarbon non-substituted or substituted with a nitro, nitrile, halogen, alkyl, alkoxy or amino group; thiophene group substituted with a C1-C20 hydrocarbon or C6-C24 aromatic hydrocarbon; and a boron group substituted with an aromatic hydrocarbon; 92 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 Ar is an aromatic hydrocarbon non-substituted or substituted with a nitro, nitrile, haloqen, alkyl, alkoxy or amino group; and each or 1, m and n is an integer of 1 or more and o is an integer or 0 or more; with the proviso that the compound represented by formula 1 wherein Rl, R2, R3, R4, R5 and R6 represent, hydrogen atoms simultaneously and D is also a hydrogen atom is excluded. 2. The compound according to claim 1, wherein the aromatic hydrocarbon includes phenyl, biphenyl, terphenyl, naphthyl, anthracenyl , phenanthrene, pyrenyl and perylenyl. 3. The compound according to claim 1, wherein the heteroaromatic hydrocarbon includes thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, thiadiazole, triazole, pyridyl, pyridazyl, pyrazine, quinoline and isoquinoline. 4. The compound according to claim 1, wherein the compound is represented by any one formula selected from the group consisting of the following formulae 2a-2e: [formula 2a] 93 94 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 wherein each of 1, m, n, o and R1-R8 is the same as defined in claim 1. 5. The compound according to claim 1, wherein the compound is represented by any one formula selected from the following formulae 3a-3n: 95 96 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 97 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 wherein each of R1-R8 is the same as defined in claim 1. 6. The compound according to claim 1, v/herein the compound represented by formula 1 is any one of compounds represented by the following formulae 61-227: 98 99 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 100 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 101 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 102 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 103 WO 2005/090512 PCT/KR2O05/0O0794 104 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 105 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 106 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 107 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 108 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 109 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 110 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 111 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 112 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 113 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 114 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 115 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 116 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 117 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 118 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 119 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 120 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 WO 2OO5/O9O5I2 PCT/KR2O05/00O794 7. An organic 1iqht omitting device comprising a first electrode, a second electrode and one or more organic compound layers disposed between both the electrodes, wherein at least one of the organic compound layers comprises at least one compound as defined in any one of claims 1 to 6. 8. The organic light emitting device according to claim 7, wherein the organic compound layer comprising at least one compound as defined in any one of claims 1 to 6 is a hole injection/hole transport layer having WO 2OO5/O9O5I2 PCT/KR2O05/00O794 hole injection and hoie transport functions. 9. The organic light emitting device according to claim 7, wherein the organic compound layer comprising at least one compound as defined in any one of claims 1 to 6 is a hole injection/hole transport/light emitting layer having hole injection, hole transport and light emitting functions. 10. The organic light emitting device according to claim 7, wherein the organic compound layer comprising at least one compound as defined in any one of claims 1 to 6 is a hole injection layer having hole injection function. 11. The organic light emitting device according to claim 7, which comprises a substrate, anode, hole injection layer, hole transport layer, organic light emitting layer, electron transport layer and a cathode, from the bottom, wherein the organic compound layer comprising at least, one compound as defined in any one of claims 1 to 6 is at least one selected from the group consisting off the hole injection layer, hole transport layer and the light emitting layer. The present invention relates to a novel compound that can significantly improve the lifespan, efficiency and thermal stability of an organic light emitting device, and to an organic electroluminescence device or light emitting device comprising the compound in an organic compound layer is also disclosed. |
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01638-kolnp-2006 correspondence others.pdf
01638-kolnp-2006 description (complete).pdf
01638-kolnp-2006 international publication.pdf
01638-kolnp-2006 international search report.pdf
01638-kolnp-2006 priority document.pdf
01638-kolnp-2006-assignment.pdf
01638-kolnp-2006-correspondence others-1.1.pdf
01638-kolnp-2006-correspondence-1.2.pdf
1638-KOLNP-2006-(28-02-2013)-ABSTRACT.pdf
1638-KOLNP-2006-(28-02-2013)-AMANDED PAGES OF SPECIFICATION.pdf
1638-KOLNP-2006-(28-02-2013)-ANNEXURE TO FORM-3.pdf
1638-KOLNP-2006-(28-02-2013)-CLAIMS.pdf
1638-KOLNP-2006-(28-02-2013)-CORRESPONDENCE.pdf
1638-KOLNP-2006-(28-02-2013)-DRAWINGS.pdf
1638-KOLNP-2006-(28-02-2013)-FORM-1.pdf
1638-KOLNP-2006-(28-02-2013)-FORM-2.pdf
1638-KOLNP-2006-(28-02-2013)-OTHERS.pdf
1638-KOLNP-2006-(28-02-2013)-PETITION UNDER RULE 137-1.pdf
1638-KOLNP-2006-(28-02-2013)-PETITION UNDER RULE 137.pdf
1638-KOLNP-2006-CORRESPONDENCE.pdf
| Patent Number | 256488 | |||||||||||||||||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Indian Patent Application Number | 1638/KOLNP/2006 | |||||||||||||||||||||||||||||||||
| PG Journal Number | 26/2013 | |||||||||||||||||||||||||||||||||
| Publication Date | 28-Jun-2013 | |||||||||||||||||||||||||||||||||
| Grant Date | 24-Jun-2013 | |||||||||||||||||||||||||||||||||
| Date of Filing | 13-Jun-2006 | |||||||||||||||||||||||||||||||||
| Name of Patentee | LG CHEM, LTD. | |||||||||||||||||||||||||||||||||
| Applicant Address | LG TWIN TOWER 20, YOIDO-DONG, YOUNGDUNGPO-GU, SEOUL, 150-721 | |||||||||||||||||||||||||||||||||
Inventors:
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| PCT International Classification Number | C09K 11/06 | |||||||||||||||||||||||||||||||||
| PCT International Application Number | PCT/KR2005/000794 | |||||||||||||||||||||||||||||||||
| PCT International Filing date | 2005-03-18 | |||||||||||||||||||||||||||||||||
PCT Conventions:
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