TWI294454B - New material for injecting or transporting holes and organic electroluminescence devices using the same - Google Patents

Description

1294454 IX. Description of the Invention: [Technical Field] The present invention relates to a novel compound which greatly enhances the service life, performance, and thermal stability of an organic light emitting display; and also relates to a 5 organic electroluminescent device, Among them, the same compound is contained in an organic compound layer. [Prior Art] In the era of advanced information technology in the 21st century, a large amount of information will be quickly and easily obtained, so the importance of a panel for multimedia and high-performance flat display is increasing. Although liquid crystal displays (LCDs) have been the main part of flat-panel displays so far, many attempts have been made to develop novel flat-panel displays that are not only cost-effective and outstanding, but also different from current liquid crystal displays. Compared with liquid crystal displays, organic electro-acoustic 15 (EL) devices or organic light-emitting displays have the advantages of low driving voltage, relatively low response speed, high performance, and wide viewing angle, because 'this expectation plays an important role. The role of an advanced flat panel display. In addition, when the organic electroluminescence phenomenon is applied as a display, the overall module can be allowed to have a thickness of 2 mm or less, and can be fabricated on a plastic substrate having a thickness of 〇3 mm or less to satisfy. The display is getting thinner and shrinking. In addition, the organic electroluminescent display has an additional advantage in that the manufacturing cost is lower than that of the liquid crystal display. The principle mechanism of an organic light-emitting display is based on the injection of electrons and holes into an organic film formed by an organic compound, and the formation of excitons (exitGns) through an anode and a cathode of 1294454. When the excitons are reorganized, there is a certain, long = light will be emitted from the excitons. In 1965, electroluminescence was first discovered in a single crystal of P〇pe et al. Since then, in 1987, Tang et al. found at Kodak that organic light-emitting displays formed from organic 5 materials with individual functional thin-layer structures can provide a homoluminescence of 1000 Cd/m2 or more 'even in 1 〇V or a lower low voltage can be used; wherein the four-layer structure can be exemplified by a hole transfer layer composed of a sheet and an electro-excitation layer structure. After these findings, organic light-emitting displays have hitherto been a research of interest in the field of display technology (Tang, C.W.; 10 Vanslyke, S. A. Appl. Phys. Lett. 1987, 51, 913). The organic light-emitting luminescence can be classified into fluorescence and phosphorescence, and phosphorescence can provide a south performance of more than seven glory base performance. On the other hand, the organic light emitting display can be classified according to the molecular weight of the organic material forming the organic light emitting display. For example, some organic light emitting devices prepared by a low molecular weight method are processes using a vacuum sublimation; The organic light emitting display prepared by the high molecular weight method is a solution process using, for example, spin coating, ink jet printing, or roller coating. Referring to FIG. 1 , a conventional organic light emitting display comprises an anode, a hole injection layer receiving the anode hole, a hole transfer layer for transferring the electricity hole, a hole and an electron. The combined light-emitting electrical excitation layer, an electron transfer layer that receives the cathode electrons and transfers it to the electroluminescent layer, and a cathode, each of which can be formed via a vacuum deposition process. Among them, the reason for manufacturing the organic light-emitting display having a multilayer film structure can be as follows. When a suitable hole transfer layer 1294454: and an electron transfer layer are used, the holes and electrons can be transferred more efficiently to an electro-optical layer because in the organic material, the electric (IV) movement rate is significantly = electron. In addition, when the hole density and the electron density are balanced in the _ electroluminescence layer, the luminescence efficiency can be increased. The following conventional organic light emitting display will be described with reference to FIG. The substrate 1 is a support for an organic light emitting display, and it may be formed of a twin crystal, a quartz or glass plate, a metal plate, a plastic film or a sheet or the like. Preferably, a glass plate; or a transparent plate made of a synthetic resin such as polyester, polymethyl acrylate, or polysulfone may be used. The soil 10 15 -20 and the first electrode (anode) 2 are disposed on the substrate U. The anode injects a hole into a hole injection layer 3, and may be made of a metal such as aluminum, gold, silver, nickel, palladium, or platinum; a metal oxide such as indium-tin oxide or indium-zinc oxide; metal a halide; carbon black; or a conductive polymer such as poly(3-methylthi〇Phene), polypyrrole (P〇iypyrr〇ie), or polyaniline. The hole injection layer 3 is disposed on the anode 2, and the material used for the hole injection layer needs to be injected from the anode to provide high-efficiency holes, and efficiently transfer the injected holes. Therefore, the hole injection The material of the human layer needs to have a low ion potential 'not only for visible light - high transparency, but also good hole stability. When the hole injection layer and the anode are squeezed to form a stable interface, the material contained in the material for the hole injection layer needs to have a good thermal stability. Typical examples of materials may include copper phthalocyanine (copper ph; cyani IJ CuPc), which is a porphyrin copper (p〇rphyrin_c〇pper), and is disclosed in U.S. Patent No. 4,356,429, issued to Kodak. in. Since Cupc is the most stable compound, it has been widely used in a hole injection layer. However, it has an absorption band in the blue and red regions, which causes problems in manufacturing a full color display device. Recently, an attractive aryl 5 aryl arylamine compound is known to have no absorption band in the blue region (U.S. Patent No. 5,256,945, Japanese Laid-Open Publication No. 1999-219788, and the following formulas 4 to 12). Particularly, in the amine compound having no absorption band in the blue region, it can be represented by the following Formula 8 to Formula 12, and it has a ι 〇〇 C or a higher glass transition temperature (Tg) and a good twist. Therefore, 10 has been used as the material of the hole injection layer.

8 8 1294454

Equation 12 η has reported that 'Xu Xi's hole injection material has a higher glass transition degree, and further improve its thermal stability. Most of the compounds are those derived from Kodak Company, and are represented by the following formulas 13 to η as representative compounds (see Japanese Patent Laid-Open No. Hei 9-301934, and U.S. Patent Nos. 6,334,283 and 6,541,129). . 8 10 1294454

Me NPB type 13

Further, Japanese Laid-Open Patent Publication No. 2003-238501 discloses an aromatic oligoamine derivative in which the derivative has at least five nitrogen atoms (Formula 18 and Formula 19) in one molecule. 1294454

In addition, a material containing a carbaz〇le group (Formula 20), which is organic in a light, has been disclosed in Japanese Laid-Open Patent Publication No. 2003-317966 and U.S. Patent No. 6,660,410. In the illuminating display, an electroluminescent layer is formed particularly as a main body, and the lifetime of the organic luminescent display can be increased compared to the conventionally known CBp (carbazole biphenyl). Other compounds for use in a hole injection layer can be represented by the following formulas 21 to 27. 10

Equation 21

Equation 23 8 1294454

Equation 24

5 A hole transport layer 4 is disposed on the hole injection layer 3. The hole transport layer can be used to receive holes from the hole injection layer and transport them to an organic electroluminescent layer 5 above the hole transport layer. The hole transport layer has high hole transportability and stability for the hole and also acts as a barrier layer to protect the electrons. In addition to the above basic requirements, when applied to an automotive display device, for example, the material for the hole transport layer preferably has an improved heat resistance and a glass of 80 ° C or higher. Transfer temperature. Materials satisfying this requirement may include NPB, a spyro-arylamine compound, a perylene-arylamine compound, azacycloheptatriene compound, bis(diphenylethylene benzene) 15 () bis (diphenylvinylphenyl) anthracene), agglomerate oxide, an aromatic amine compound containing ruthenium, or the like. 1294454 At the same time, aromatic amine compounds with high hole transport speed and good electrical stability can be used as an important organic single molecule for the hole transport layer. In order to improve the thermal stability of the aromatic amine compound, the hole transporting material can be introduced into a naphthalene substituent or a spyro group (see U.S. Patent Nos. 5,5,554,459 and 5,840,217). Initially, N,N'_diphenyl-N,N,-bis(3-methylphenyl:indole, 1'-diphenyl-4,4,diamine (N,N'-diphenyl-N, N'-bis(3-methylphenyl)-l,l'-diphenyl_4 ,4'-diamine ; TPD) is often used as an organic hole transport material. However, since TPD is unstable at 60 ° C or higher, Currently using N-10 naphthyl-N-phenyl-1,1'-diphenyl-4,4'-diamine (1^_1^?11 to 71-1^-phenyl-l,l'- Diphenyl-4,4'-diamine; NPD)-based materials, or amine-based compounds substituted with a larger number of aromatics and having a higher glass transition temperature. In particular, organic single molecules used in the hole transport layer, It has a high hole transmission speed. In addition, since a hole transport layer is connected to an electric 15 excitation layer and forms an interface with each other, the organic single molecule applied to the hole transport layer must have a sufficient ion potential value. It is interposed between a hole injection layer and an electroluminescent layer to suppress excitons generated at the interface between the hole transport layer and the electroluminescent layer. Further, the hole transport layer Organic single molecule The material may be required to control electron transport from the organic electroluminescent layer 20. An organic electroluminescent layer 5 is disposed on the hole transport layer 4. The organic electroluminescent layer emits light from the anode and cathode. The respective injected holes and electrons are re-elected and formed by materials with high quantum efficiency. The organic single molecules used in the electroluminescent layer can be functionally classified into 13 1294454 bulk materials and objects. A material in which the light emission of the light-emitting layer is achieved by recombination of holes and electrons. Generally, the light is emitted when the host material or the guest material is used alone. However, the host material is designed to solve low efficiency and luminosity. The problem is that the guest material is added, and in addition to the unique characteristics of each molecule, the problem of self-packing of the same molecule affects the characteristics of the excimer. More specifically, the green emission layer When using 8-octahydroquinoline aluminum salt (Alq3) alone, high quantum potency materials such as quinacridone or C545t can be incorporated to enhance hair growth. 10 Efficacy. Organic materials used in a blue-emitting layer have problems due to their low melting point and low luminescent stability, which may cause problems in the early stage of use. Compared with Alq3 green light-emitting materials, blue-emitting materials have a poor service life. In addition, because most of the materials used in the blue-emitting layer are a light blue light, pure blue light is not suitable for full-color displays, so the material is also added to (perylene) or stilbene. Amine (DSA) U enhances luminescence efficacy. The organic material typically used for the blue-emitting layer may comprise (a sulphur-hydrogen compound, a spyro-type compound, an organometallic compound, a heterocyclic compound having an imidazole, or a fused aromatic) Compounds, which are disclosed in U.S. Patent Nos. 5,516,577, 5,366,81, 5,840,217, 5,150, 006, and 5,645, 948. Also, in the case of a red-emitting layer, due to the narrow band of red light emission The characteristics of the gap, so a small amount of green light emitting material is poured into a large amount of green light emitting material. However, such materials have structural problems, thus hindering the life of the component. 1294454 An electron transport layer 6 is disposed in Electromechanical excitation layer 5. In the electron transport layer 6, this type of suitable material (second electrode) needs to have a high electron injection efficiency from the cathode 7, and efficiently transport the injected electrons. Characteristics, this material must have a high degree of electron affinity 5 and electron movement speed, and has good stability for electrons. An aromatic compound such as tetraphenyl butyl dichloride (Japanese Patent Laid-Open No. Sho 57-51781); a metal complex such as 8-hydroxyquinoline (Japanese Patent Laid-Open No. 59-194393) a 10-metal benzoic acid (10-hydroxybenzo[h]quinoliiie) (Japanese Patent Laid-Open No. 6-322362); cyclopentadiene derivative (Japanese Patent Laid-Open No. 2489675) Bisstyrylbenzene derivative (Japanese Patent Laid-Open No. 1-245087, and JP-A-2-222484); 茈(?67&1^) derivative (曰本专利-平平2-189890, and Kaiping 3-791); p-phenylene derivative (Japanese Patent Laid-Open No. Hei 3-33183, and JP Hei No. Hei 11-345686); oxazole derivative; or the like. The organic single molecule used in an electron transport layer may contain an organometallic complex, and it has a relatively high electron stability and electron moving speed. In particular, Alq3 is currently known to be the best material to be used because of its outstanding Stability and high degree of electronic affinity. In addition to the above materials, Other electron transport materials known to those of ordinary skill in the art may comprise a series of flavones or silols, and are available from Chisso, Inc. In addition to the materials described above for use in the electron transport layer, A special choice. In general, the electron transporting material is in the form of a metal to form a mixture of 8 15 1294454, which is used in the cathode. Further, an inorganic material such as a fluorinated clock (LiF) can also be used. The cathode 7 is for injecting electrons into the organic electroluminescent layer 5, and a material for the anode 2 can also be used in the cathode 7. However, in order to inject electrons more efficiently, the cathode 7 preferably uses a metal material having a low working energy. Among them, the metal may include, for example, lithium, planer, sodium, tin, magnesium, indium, consuming, chain, alloys thereof and the like. However, an organic electroluminescent display device using an organic single molecule and formed by lamination generally has a short service life, and has problems of poor durability 10 and reliability. Such problems arise from changes in physical, chemical, photochemical, and electrochemical properties of organic materials, the oxidation of the cathode 'interfacial layer separation', and the dissolution, crystallization, and hydrazine cracking of organic compounds. 15 [Summary of the Invention] As described above, 'conventional organic metal-containing complexes such as CuPC, aromatic amine compounds, and calcareous-containing hole injecting materials have problems in that full-color demand cannot be achieved and poor stability is exhibited. . - The inventors synthesized a novel organic compound containing a sigma-based group, which is shown in the following formula 1, and found that the novel compound can be used as a hole injecting and transporting material to promote the performance of the organic light-emitting display. The service life and thermal stability have been greatly improved. The present invention is based on this finding. As described above, by adjusting the structure of an appropriate organic single molecule, it is possible to obtain a desired color in an organic electroluminescent device. Based on this consideration, 16 1294454 under the "utility-host system" (host-guest systems), can provide a variety of high-performance organic electroluminescent devices. However, this type of device exhibits insufficient electro-excitation characteristics, service life, and durability for practical use. Therefore, the architecture of the present invention is based on the above problems. 5 It is an object of the present invention to provide a novel material for use in hole injection into a hole transport layer which enhances the efficacy, stability, and lifetime of the electroluminescent device and provides - An organic electroluminescent device using this material. 1) Another object of the present invention is to provide a material having a high glass transition temperature, good: stable, and bismuth properties for use in a vacuum vapor deposition process. 4 In one aspect of the invention, there is provided an organic electroluminescent device comprising an organic compound as shown in Formula 1, and a compound comprising the compound in an organic compound layer:

φ , Λ Η r ?2 R2 R4 八 f, Α疋-[R1 —Ν_] or —[R Bushan_Ar one]; 3 is _|>3一&一] 15 ^-[Rs-T -Ar-l ; C θ Γ 1 JC 疋[R5-N-] or a [R5-N-Ar-]; and D is ττ r f8 R10 , ~[R7- N-] or a [R9'N —Ar—]. In the above formula, R#jRi〇 is the same or different, and the lanthanide group 8 1294454 further comprises one or at least two or more of at least one selected from the group consisting of hydrogen atoms; aliphatic hydrocarbons having 1 to 20 carbon atoms; a compound; an unsubstituted or substituted aromatic hydrogen-hydrogen compound wherein the substituent is a terminal group, a sulfhydryl group, a halogen, a decyl group, a methoxy group, or an amine group; and a group having an aromatic substituent An unsubstituted or substituted heterocyclic aromatic hydrocarbon wherein the substituent is a nitro group, a nitroso group, an alkyl group, an alkoxy group, or an amine group; a Ci to C2G hydrocarbon, or a group of thiophenes substituted with an aromatic hydrogen-hydrogen compound; and a boron group substituted with an aromatic hydrocarbon. And Ar is an unsubstituted or substituted aromatic hydrocarbon hydrazine compound in which the substituent may be a stone succinyl group, a nitroso group, a halogen group, a hospital group, an alkoxy group, or an amine group. In the above chemical formula, each of 1, m, and η is an integer of 1 or more, and 〇 is an integer of 0 or more. Preferably, 1, m, and η are both 1 and 〇 is 0, and Ri, R2, R3, R4, Rs, R6, and D 15 of the compound of Formula 1 are not simultaneously a hydrogen atom. The above aromatic hydrocarbon may contain a monocyclic aromatic ring such as (phenyl, biphenyl, and terphenyl); and a polycyclic aromatic mono-cyclic ring such as naphthyl, anthracenyl, Phenanthrene, 'pyrenyl, and perylenyl; or the like. . . . -20 -20. In addition, the above heterocyclic aromatic hydrocarbon may contain thiophene, furan, 0 Pyrrole, imidazole, thiazole, oxazole, 11 oxadiazole, thiadiazole, triazole ), pyridyl, °, pyridazyl, pyrazine, quinoline, isoquinoline, etc. Preferably, The compound represented by the above formula 1 may be any compound selected from the following formula 2a to formula 2e: 5 R2 R3

Equation 2a

Equation 2c

Equation 2b

R2 R3

19 1294454 In a more preferred aspect of the invention, the compound represented by the above formula 1 may be any compound selected from the following formula 3a to formula 3n:

Equation 3c Equation 3d 10

Equation 3e Equation 3f

Formula 3g, formula 3h, 8 1294454

Equation 3iji 3n. 10 In each of the above formulas and formulas 3a to 3n, the illusion to R8 is the same as defined in the first item of the patent application. Hereinafter, the present invention will be explained in more detail. The organic compound represented by Formula 1, Formula 2, or Formula 3 can be used as a hole injection and hole transport material, and in an organic electroluminescent device, 15 can be at least one selected from a hole. An injection layer, a hole transport layer, and an electrical (s) 21 1294454 excitation layer between the layers. In particular, each compound contains a '-salt group and readily accepts and transports holes. The function mentioned here is produced by the cyclic structure present in the card 11 sitting group and exhibits a structure in which an aromatic hydroxyl group is bonded to the carzol group. 5 Therefore, an organic material layer containing the above compound can be injected as a hole or a hole transport layer. In addition, the organic material layer can serve as an electroluminescent layer in which holes and electrons can be recombined to achieve light emission. In other words, the compound of the present invention can achieve at least one function selected from the group consisting of hole injection, (: hole transport, and light emission. Similarly, in an organic 10-light-emitting display, the layer containing the above compound can be And at least one selected from the group consisting of a hole injection layer, a hole transport layer, and an electroluminescence layer. Further, the layer containing the above compound can be used as a hole injection/hole transport layer, and hole injection/electricity. a hole transport/electroluminescence layer, etc. More specifically, an aromatic hydroxyl group bonded to a carzol group by an aromatic hydroxyl group of a carzol group or a substituted 15 group, and a basic body of a carboxazole The compound can stably and safely accept and transport holes. In addition, the substituent bonded to the /carbazole group is derived from an amine group. Such a substituent can be used to carry the movement of the hole, and The structure of the compound of the invention is in a stable state. It does not impede the flow of the holes. Therefore, the 20 electromechanical excitation device containing the compound of the present invention can exhibit excellent stability and improve its service life. Further, the substituent of the compound of the present invention may, for example, be an R 1 to R 10 may be any substituent when a compound having a substituent of R 1 to R 10 exhibits a desired function in an organic electroluminescent device. And exceeds the type of the substituent mentioned above. For example, when R1 to R10 1294454 represents a leukoyl group or a substituent substituted with a leukoyl group, the chain length of each alkyl group is not limited because of the burning contained in the compound. * The base chain length does not affect the resonance length of the compound, so it does not directly affect the wavelength of the compound or the characteristics of the light-emitting device. However, the chain length of the stimuli can affect the choice of the method for applying the compound to an organic 5-luminous display. For example, a vacuum deposition method, or a solution coating method. Therefore, 'there is no particular limitation in the bond length of the alkyl group' and it may include the compound represented by the above formula. • About R1 to R10 in the above formula Particularly exemplified aromatic compounds may contain a monocyclic aromatic ring such as phenyl, biphenyl, terphenyl, etc.; 10 and a polycyclic aromatic ring such as naphthyl, anthracenyl , pyrenyl, perylenyl, etc. Particularly exemplified heterocyclic aromatic compounds may include σ-sept, sigma, pyrrole, imi, imidazole, σ 啥(thiazole), ° oxazole, oxadiazole, thiadiazole, triazole, 15 11 pyridyl, and ratio. Pyridazyl), pyrazine, quinoline, isoquinoline, etc. f The aliphatic hydrocarbon having 1 to 20 carbon atoms may contain linear aliphatic hydrocarbons And branched aliphatic hydrocarbons. In particular, exemplary hydrocarbon types may contain alkyl groups such as fluorenyl, ethyl, n-nonylpropanyl, iso-propane, n-butane, 2-butane, iso-butane And: 'C. tributyl, pentylene, hexane, etc.; an alkenyl group having a double bond, such as styryl; and a fast radical having a triple bond, such as acetylene. The compound of the present invention is not limited, and may include a compound represented by the following formula 28 to formula 260 23 8 1294454.

Equation 28 Equation 29 Equation 30 ~ 5

Type 31, formula 32, type 33

24 1294454

Formula 40

25 1294454

Equation 52 8 1294454 ορο ορο

Equation 53 αρο

5

Equation 57

27 8 1294454

Equation 60

8 1294454αρ οςο

8 1294454

Equation 75 76 30 8 1294454

1294454

Equation 83 Formula 84 32 8 1294454

Q Q

Q Q

33 8 1294454

Equation 89

Equation 90

Formula 94

Formula 95 96 34 8 1294454

Formula 101, formula 35 35 8 1294454

Formula 107

36 1294454

Formula 110

MeO

MeO

OMe

Formula 112

Formula 113

37 8 1294454

Formula 115

117 Type 118 OMe OMe

OMe style 119

Equation 120 38 1294454

Equation 124

OMe OMe

Equation 126 125 39 1294454 OMe OMe

Formula 127

Formula 132 (S) 40 1294454

OMe OMe

Formula 134

137 138 8 1294454

Σο ςο

143 144 42 8 1294454 OMe OMe

Formula 145

8 1294454

Equation 151 OMe OMe

OMe OMe

Formula 152

Formula 153

Equation 154

Formula 155

Equation 156

Equation 158 44 8 1294454

Equation 159 OMe OMe

Formula 161

Formula 162

Equation 165

(g 1294454

Type 168

Type 170 171 type 172

Equation 174

175 176 46 8 1294454

Equation 177

Type 5 179 Type 180

Formula 181

183 184 185

47 1294454 α

Equation 186

Q

r) ΛΝ.) \ 式 187 188

Formula 191

192 type 193 type 194

195 196 197 (8) 48 1294454

199 type 199 type 200

Formula 201, formula 203

Formula 204

Formula 206

10 type 208 type 209 type 210 49 rs) 1294454

Equation 212

Formula 214

Formula 215

217 218 219 50 1294454

221

Equation 222

QO CpO

• Type 227

228 229 51 (s) 1294454

Formula 230

Formula 232

234 235 52 (S) 1294454

Σο cp ν, ρ ςο αρ ν, 〇 236

Formula 240

53 8 1294454 opo Cpo

Equation 246

54 1294454

249

5 type 250 type 251

252 253 (S) 55 1294454

Equation 255

257 5 formula 256

Equation 258

259 56 8 1294454 10

The organic compounds of the above formula can be synthesized by subjecting their starting materials through three to eight process steps. In one embodiment of the synthetic process of the invention, the above compounds can be prepared from the carazole starting materials. First, the carbazole is treated with dentate atoms or dentated benzene to form a dentate or halogenated stupid substituted starting material. Next, each of the compounds of the above formula 1 wherein each of a, b, c, d, 4 R1 to Rio is introduced into the starting material to replace the halogen atom of the starting material to form a desired compound. In this process, a catalyst can be used. In the halogen selection, there is no particular limitation; in general, bromine, chlorine, or the like can be used. Regarding the structural formula of the compound of the present invention, a suitable synthetic process can be designed by a known technique. In the following examples, the synthesis of some of the compounds will be described. Fig. 1 is a preferred embodiment of an organic electroluminescent device. The organic compound of the present invention can be used in at least one organic material layer and formed between an anode and a cathode, for example, at least One is selected from the group consisting of a hole injection layer, a hole transport layer, and an electroluminescent layer. More specifically, the compound can be used for a hole injection layer, a hole transport layer, and an electric 8 1294454 hole injection/ The hole transport layer, or a hole injection/hole transmission/electroluminescence layer, while a bulk material having a large energy gap (for example, CPB) can be incorporated into an organic phosphorescent material (for example: Phenylpyridine iridium, in order to successfully provide a high-performance device. This indicates the effect of a single-single-singlet transition: it can limit the triplet-triplet transition ( Triplet_triplet two transitions. Therefore, when the novel hole injecting material of the present invention is used as a main material to emit phosphorescent-based excitation light, it can obtain a significant improvement of luminous efficacy and service life of 10. Organic electroluminescent device ((C. Adachi, A. Baldo, and S. R. Forrest, Applied Physics Letter, 77, 904, 2000, C. Adachi, MA Baldo, SR Forrest, S. Lamansky, Μ · E. Thompsom, and R. (j. Kwong, Applied Physics Letter, 78; 1622, 2001) o 15 In the organic electroluminescent device, the organic material layer of the present invention comprises the above formulas 1 to 3 and 28 The compound represented by the formula 260 can be provided for significantly improved luminescence efficacy and service life, and exhibits excellent stability, uniformity. 20 [Embodiment]: After that, the present invention will be The following examples are intended to describe in detail the synthesis process of the organic compound of the above formula 1, and the organic electroluminescent device to which it is applied. However, it is to be understood that the following examples are for illustrative purposes only and are not intended to limit the scope of the invention. 58 1294454 In order to prepare a compound represented by the above formula 1, a compound represented by the following formulas a to h can be used as a starting material.

Formula b

Formula c, formula d, e

8 59 1294454 In the above formula a to formula h, hydrazine is a dentate atom, and there is no halogen atom selected thereby. In the following examples, the compound represented by the formula a to the formula h may be selected as a starting material 'where X is Br. The starting material was prepared according to the following procedure of Example 1 to Example 8 < 5 <Preparation Example 1> Preparation of the starting material of the formula a will be carbazole (5.00 g; 29.9 mmol), 1-bromo-4-iodobenzene (9·30 g; 32.9 mmol), K2C〇 3 (16.5 g; 120 mmol), Cu (3.80 g; 59.8 mmol), and 18-crown-6 (18-crown-6, 0.40 g; 1.49 mmol) in 50 ml of o-dichloro In benzene, reflux for 15 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature, and the precipitate was filtered. The filtrate was washed three times with water and dried with MgS04, followed by concentration under reduced pressure. Finally, the reaction mixture was purified by column chromatography to give the compound of formula a (5·85 g; 61%) as starting material. lHNMR (300 MHz, CDC13) 8.13-8.11 (d, 2H), 7.71-7.69 (d, 2H), 7.44-7.21 (ιη, 15 8H); MS [M+H] 322. <Preparation Example 2> Preparation of the starting material of the formula b would be card sniffing (5·00 g; 29.9 mmol), 1-bin-3-brominated benzene (9.30 g, 32.9 mmol), K2C03 (16) · 5 g; 120 mmol), Cu (3.80 g; 59.8 mmol), and 18 crowns _6 (18-cr〇wn_6, 〇·4 gram; i 49 20 mm 〇l) placed at 503⁄4 liters of o. In chlorinated benzene, reflux for 15 hours. After reacting for 70%, the reaction mixture was cooled to room temperature, and the precipitate was filtered off. The filtrate was washed three times with water and dried with Mgs04, then concentrated under reduced pressure. Finally, the reaction mixture was purified by column chromatography to obtain the compound of formula b (5·85 g; 61%) as a starting material. MS [M+H] 322. 25 (S) 60 1294454 <Preparation Example 3> Preparation of starting material of formula c The starting material of formula a (1.5 g; 4.66 mmol) was dissolved in dimethylformamide ( DMF, 20 ml), and N-bromosuccinimide (NBS '1.82 g; ι〇· 2 mmol) was added. Reaction mixture in 50-60X

After 2 hours of reaction, 15 ml of water was added. Then, the obtained precipitate was filtered, washed with water, and then recrystallized from methylene chloride/n-hexane to give the compound (1.93 g; 86%) as a starting material. 1H 10 15 -20 NMR (300 MHz, CDC13) 8.17 (s, 2H), 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] 478. &lt;Preparation Example 4&gt; Preparation of the starting material of the formula d The starting material of the formula b (1·5 g; 4β66 mm〇l) was dissolved in dimethyl decanoic acid amine (DMF '20 ml) Medium, and added N-bromobutanedithioimine (NBS '1.82 g; 1 〇 · 2 mmol). After the reaction mixture was reacted at 50-60 ° C for 2 hours, 15 ml of water was further added. Subsequently, the obtained precipitate was filtered and washed with water and then recrystallized in a methylene chloride/n-hexane solution to obtain a compound of the formula d (m. 93 g; 86%). MS [M+H] 478 〇&lt;Preparation Example 5&gt; Preparation of the starting material of the formula e: 2,5-monosylmethylide (12.0 g; 42.7 mmol) was dissolved in dimethylformamide (DMF, In 80 ml), cu (6.0 g; 93.94 mmol) was added, and the reaction mixture was reacted for 3 hours in i2 (rc). After the reaction mixture was cooled to room temperature, the insoluble matter was filtered off and the filtrate was taken. Concentration. The obtained product was recrystallized from ethanol to give 4,4, and 2,6,2,2,2,2-dinitrobiphenyl (1 〇 2 g; 60%). MS [M+] 354 Take 4,4'-dibromo-2,2'-dinitrobiphenyl (6·1 g; 15.17 mmol), stir in 75 ml of HC 130 ml / EtOH, and add tin powder (7.2 g; 60.68 mmol) Then, the reaction mixture was refluxed for 24 hours. Next, 5 the reaction mixture was cooled to room temperature and neutralized with a 10% NaOH solution. Finally, recrystallization was carried out in ethanol to obtain 4,4, dibromo-2,2. , _diaminobiphenyl (3.5 g; 67%); MS [M+H] 341. 4,4,-dibromo-2,2'-diaminobiphenyl (3.5 g; 10.23mmol) C .. dissolved in phosphoric acid and heated at 1901 24 After the reaction mixture 10 was cooled to room temperature, NaHCOvw was slowly added to form a solid. Then, the solid was filtered to obtain 2,7-dibromocarbazole (2.2 g; 66%) of the formula e. Compound; MS [M+] 323 ° &lt;Preparation Example 6&gt; Preparation of starting material of formula f: 3,6-dibromocarbazide (1.63 g; 5.00 mmol), 4-bromophenyl-acid 15 (2) · 95 g; 15.0 mmol), 2 M potassium carbonate solution (10 ml), and tetrakis (triplienylphosphine f. palladium, 29.0 mg; 〇·25 mmol) were added to 100 ml of THF. The reaction mixture was stirred under reflux for 24 hours and then cooled to room temperature. Then, the reaction mixture was introduced into toluene and brine, and the toluene layer was separated. The separated toluene layer was dried with MgSCU and then dried. Filtration and concentration. Finally, the reaction mixture was purified by column chromatography to give the compound (1. 1Η), 7.77 (s, 2H), 7.49-7.46 (m, 6H), 7.37 (d, 4H), 7.30 (d, 2H); MS [M+H] 476. 62 25 1294454 &lt;Preparation Example 7&gt; Preparation of the starting material of the formula g: a compound of the formula f (1·43 g; 3.00 mmol), 1-bromo-4-woven benzene (1·87 g; 6.60 mmol ), K2CO3 (3.32 g; 24 mmol), Cu (0.76 g; 12.0 mmol), and 18-crown-6 (18-crown-6' 5 0.08 g; 0·30 mmol) in 10 ml In o-dichlorobenzene, reflux for 15 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the precipitate was filtered. Then, the filtrate was washed three times with water, dried over MgS04, and concentrated under reduced pressure. Finally, the reaction mixture was purified by column chromatography to give the compound of formula g (1·2 g; 54%) as starting material. 1H 10 NMR (300 MHz, CDC13) 7.77 (s, 2H), 7.49-7.40 (m, 8H), 7.37 ((1,4H), 7.30 (d, 2H), 7.20 (d, 2H); MS [M+H] 630. &lt;Preparation Example 8&gt; Preparation of the starting material of the formula h The compound represented by the formula c (2.40 g; 5·00 mmol), 4-bromophenyl succinic acid (3.94 g; 20 · 0 mmol ), 2 M potassium carbonate solution (20 mL), 15 and tetrakis (triphenylphosphine), (tetrakis (triphenylphosphine) palladium, 58.0 mg; 0.50 mmol) were poured into 100 ml of THF. The mixture was stirred and refluxed for 24 hours, and then cooled to room temperature. Then, the reaction mixture was introduced into toluene and brine, and the toluene layer was separated. The separated toluene layer was dried with MgS04, filtered and concentrated. The reaction mixture was purified by column chromatography to give the title compound (2.09 g; 59%) as the starting material. 1H NMR (300 MHz, CDC13) 10.1 (s, 1H), 7.77 (s, 2H) 7.50-7.46 (m, 1_, 7.37 (m, 6H), 7.30 (m, 4H); MS [M+H] 706. 63 25 1294454 &lt;Example 1&gt; Preparation of a compound of formula 61 Compound shown (1 · gram; 2.08 mmol), diphenylamine (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; 18.7 mmol) were added to xylene (40 ml), and the reaction mixture was refluxed for 3 hours. After the reaction was completed: The reaction mixture was cooled to a temperature, and it was added to a mixed solution of THF and diH20, and the organic layer was separated and dried with MgS04, then C was concentrated, and finally purified by column chromatography. The product was recrystallized from ethyl acetate / n-hexane to afford compound (1. 6 g; 75%) of formula 61. 1H NMR (300 MHz, CDC13) 6.78 (d, 2H), 6.96 (m, 14H), 7.12 (m, 6H), 7.25 (s, 2H), 7.5-7.51 (m, 14H), 7.65 (d, 2H); MS [M+H] 745. &lt;Example 2&gt; The compound of formula 62 is prepared as shown in formula 62 (1·00 g; 2·08 mmol), N-phenyl-1-naphthylamine (1·50 g; 6·86 mmol), Pd2(dba)3 (〇·125g; 0·13 /- mmol), P(t-Bu)3 (0·04g) 0.2 mmol), and the third - butoxy, one of sodium (sodium tert-butoxide, 1.80 g of; 18 · 7 mmol) was added two; toluene (40 ml) and the reaction mixture was refluxed for 3 hours.... After the anti-friction completion -.20, the reaction mixture was cooled to a chamber overflow, and it was added to a mixed solution of THF and H20, and the organic layer was separated and dried with MgS04, and then concentrated. Finally, the obtained product was purified by column chromatography, and recrystallized from ethyl acetate / n-hexane to afford compound (. 1H NMR (300 MHz, CDC13) 8 1294454 6.78 (d, 2H), 6.96-7.12 (m, 14H), 7.25 (s, 2H), 7.5_7.51 (m3 8H), 7.65-7.66 (.m, 8Η) ), 7·80-7·81 (ιη, 6H), 8.11-8.12 (m, 6H); MS [M+H] 895 〇 &lt;Example 3 &gt; Preparation of Compound 5 of Formula 63 The compound shown (1.00 g; 2.08 mmol), N-phenyl-2-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 the mixture of benzene (40 ml) and the reaction mixture Reflux for 3 hours. After the completion of the reaction 10, the reaction mixture was cooled to room temperature, and added to a mixed solution of THF and H20, and the organic layer was separated and dried over MgS04, and then concentrated. Finally, the obtained product was purified by column chromatography, and recrystallized from ethyl acetate / n-hexane to give the compound of formula 63 (1·21 g; 65%). 1H NMR (300 MHz, CDC13) 15 6.78 (d, 2H), 6.96-7.0 (m5 8H), 7.12 (m, 3H), 7·25-7·29 (πχ, 8H), 7.51-7.73 (m, 16H), 7·94-8·05 (χη, 9H); MS [M+H] 895. (&lt;Example 4&gt; Preparation of a compound represented by Formula 64: Compound (c) (1.00 g; • 20 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) was added to diphenylbenzene (40 ml), and the reaction mixture was refluxed for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and added to a mixed solution of THF and H20 to give organic The layer was separated 8 1294454 and dried with MgS04 and then concentrated. Finally, the obtained product was purified by column chromatography and recrystallized from ethyl acetate / n-hexane to give the formula Compound (0.93 g; 43%). 1H NMR (300 MHz, CDC13) 6.78 (d, 2H), 6·96-6·97 (ιη, 5 8 Η), 7.12 (t, 3 Η), 7.25 (s, 2 Η) ), 7.41 (m, 3 Η), 7.5-7_51 (m, 8H), 7.65 (d, 2H), 8·32-8·38 (χη, 12H), 8.62 (d, 6H), 9.43 (m, 6H) MS [M+H] 1045. &lt;Example 5&gt; Preparation Compounds of formula c (1.00 g; 2.08 mmol), N-phenyl-(9-10 anthrenyl)amine (1.85 g; 6.86 mmol), Pd2(dba)3 (0.125 g; 0.13 mmol) , P(t-Bu)3 (0.40 g; 0.2 mmol), and sodium tert-butoxide (1-80 g; 18.7 mmol) were added to xylene (40 ml), and the reaction mixture was refluxed. After the reaction was completed, the reaction mixture was cooled to room temperature, and added to a mixed solution of THF 15 and H20, and the organic layer was separated and dried with MgS04, and then concentrated. Chromatography to purify the obtained product, which was recrystallized from ethyl acetate / n-hexane to give compound of formula 65 (1.24 g; 57%). 1H NMR (300 MHz, CDC13 6.78 (d, 2H), 6.96-6.98 (m, 8H), 7.12 (t, 3H), 7.23 (s5 2〇2H), 7.5-7.51 (m, 8H), 7.65-7.66 (m, 7H), 7·81-7·84 (πι, 10H), 8.14-8.15 (m, 12H); MS [M+H] 1045. &lt;Example 6&gt; Preparation of a compound represented by the formula 68 Compound (c.; Dba)3 (0.125 g; 0·13 8 1294454 mmol), P(t-Bu)3 (0.04 g; 0.2 mmol), and sodium tert-butoxide (1·80 g; 18.7 mmol) was added to diphenylbenzene (40 mL) and the reaction mixture was refluxed for 3 h. After the completion of the reaction, the reaction mixture was cooled to room temperature, and added to a mixture of THF and 5, and H20, and the organic layer was separated and dried with MgSO 4 and then concentrated. Finally, the obtained product was purified by column chromatography, and recrystallized from ethyl acetate / n-hexane to afford compound (1.04 g; 48%). 1H NMR (300 MHz, (, CDC13) 6-78 (d, 2H), 7.0-7.05 (m, 8H&gt;, 7.25 (s, 2H), 10 7.50_7.66 (m, 16H), 7·80- 7·81(ιη, 12H), 8·11-8·16(πι, 12H); MS [M+H] 1045. &lt;Example 7&gt; Preparation of a compound of formula 69 Compound of formula c (1.00 g; 2·08 mmol), bis-(2-naphthyl)amine (1·85 g; 6·86 mmol), Pd2 (ciba) 3 (0.125 g; 0.13 15 mmol), P(t-Bu) 3 (0·04 g; 0·2 mmol)', and sodium tert-butoxide (1.80 g; 18.7 mmol) was added to (diphenylbenzene (40 ml), and the reaction mixture was refluxed 3 After the reaction is completed, the reaction mixture is cooled to room temperature, and added to a mixed solution of THF and H20, the organic layer is separated and dried with MgS04, -20 and then concentrated. Chromatography. The product obtained was purified and recrystallized from ethyl acetate/n-hexane to give the compound of formula 69 (0.89 g; 41%). 1H NMR (300 MHz, CDC13 ) 6.78 (d, 2H), 7·0 (ί1, 2H), 7.26-7-29 (m, 14H), 7.5-7.53 (m, 16) Η), 7·94-8·05 (ηι, 18H); MS [M+H] 1045 〇25 (s) 1294454 &lt;Example 8&gt; Preparation of the compound of the formula 71 The compound of the formula c ( 1.50 g; 3.13 mmol), ρ,ρ'-dimethylphenylamine (2.03 g; 10.3 mmol), Pd2(dba)3 (0.19 g; 5 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 reaction mixture was refluxed for 3 hr. After completion of the reaction, the reaction mixture was cooled to room temperature, and it was added to a mixed solution of THF- and H20, and the organic layer was separated and dried with MgS04, then concentrated, and finally purified by column chromatography. The obtained product was recrystallized from ethyl acetate / n-hexane to give the compound of formula 71 (1.31 g; 50%). 1H NMR (300 MHz, CDC13) 2.55 (s, 18H), 6·48-6·70 (ιη, 16Η), 6.95-7·01 (πχ, 14Η), 7·2-7·35 (πι, 4H); MS [Μ+Η] 829. 15 &lt;Example 9&gt; Preparation of the compound of the formula 72 The compound of the formula c (1·50 g; 3.13 mmol), m, m'-diphenyleneamine (1·96 ml; 10·3) Mmmol), Pd2(dba)3 (0.19 g; 0.21 mmo〇, P(t_Bu)3 (0·06 g; 0·31 mmol), and sodium tert-butoxide (1) 05 g; 10.96 mmol) was added to 20-biphenylbenzene (30 ml), and the reaction mixture was refluxed for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and added to a mixed solution of THF and 1120. The organic layer was separated and dried with MgS04, and then concentrated. Finally, the obtained product was purified by column chromatography, and recrystallized from ethyl acetate/n-hexane solution to give 25 formula 72 Compound (Ig 55 g; 60%). 1H NMR (300 MHz, 68 1294454 CDC13) 2.55 (s, 18H), 6.48-6.70 (m, 16H), 6·95-7·01 (χη, 14H) 7·2-7·35(ηι, 4H); MS [M+H] 829. <Example 10> Preparation of the compound of formula 89 Compound of formula c (1·50 g; 3.13 mmol) 3-mercapto-di 5 benzene (1.88 g; 10.3 111111〇1), ?(12(仙&)3(0.19g; 0.21111111〇1), P(t-Bu)3(0·06g; 0·31 mmol), and third - sodium tert-butoxide (1.05 g; 10.96 mmol) was added to xylene (30 ml), and the reaction mixture was refluxed for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and A mixed solution of THF and H 2 O was added, the organic layer was separated and dried over MgS04, and then concentrated. Finally, the obtained product was purified by column chromatography and in ethyl acetate / n-hexane. Recrystallization was carried out to obtain a compound of the formula 89 (1.62 g; 66%); MS [M+H] 787. &lt;&lt;&gt;&gt;&gt;&gt; (1.50 g; 3·13 mmol), N-(3-decylphenyl)_1-naphthylamine (2.40 g; 10.3 mmol), Pd2(dba)3 (0.19 g; 0·21 mmoi), P (t-Bu)3 (0.06 g; 0·31 mmol), and third, sodium tert-butoxide (1.05 g; 10.96 mmol) was added to xylene (30 ml), and the reaction was mixed. Reflux for 3 hours. After the completion of the reaction of 20, the reaction mixture was cooled to room temperature and was added to a mixed solution of THF and hydrazine, and the organic layer was separated and dried with MgSO 4 and then concentrated. Finally, the obtained product was purified by column chromatography, and recrystallized from ethyl acetate/n-hexanes to give the compound of formula 95 (1.92 g; 65%). MS [M+H] 937. 25 69 1294454 &lt;Example 12 &gt; Preparation of a compound of formula 96, compound (c. 2·40 g; 1〇·3 mmol), Pd2(dba)3(〇·19 g; 0.21 mmol), P(t-Bu)3 (〇·〇6 g; 0.31 mmol), and 5 third- Sodium tert-butoxide (1. 05 g; 1 〇 96 mmol) was added to xylene (30 mL) and the reaction mixture was refluxed for 3 hr. After the reaction was completed, the reaction mixture was cooled to room temperature, and added to a mixed solution of THF and H20, which was separated, dried over NigS04, and then concentrated. The product thus obtained was purified by column chromatography, and recrystallized from ethyl acetate / n-hexane to give the compound represented by formula 96 (1·92 g; 65%). MS [Μ+Η] 937 〇&lt;Example 13 &gt; Preparation of the compound of the formula 101 The compound of the formula c (1·50 g; 3.13 mmol), N"(3-methylphenyl)- 2-naphthylamine (2·40 g; 10.3 mmol), Pd2(dba)3 (0·19 15 g; 0·21 mmol), P(t&gt;Bu)3 (0·〇6 g; 0·31 Methyl), and sodium tert-butoxide [1. 05 g; 10.96 mmol) were added to xylene (30 mL) and the reaction mixture was refluxed for 3 hr. After the reaction was completed, the reaction mixture was cooled to room temperature and was added to a mixed solution of THF and H20, and the organic layer was separated and dried with MgSO 4 and then concentrated. Finally, the obtained product was purified by column chromatography, and recrystallized from ethyl acetate/n-hexane to afford compound (1·92 g; 65%). MS [M+H] 937. <Example 14> A compound represented by the formula 102 (1.50 g; 3·13 mmol), N-(4-methyl 1294454 phenyl)-2-naphthylamine (2.40 g; L〇.3mmol), Pd2(dba)3 (〇·ι9 gram; 0·21 mmol), P(t-Bu)3 (0·06 gram, · 0·31 mmol), and third-butoxide (Sodium tert_butoxide, 1.05 g; 10.96 mmol) was added to dichloromethane (30 mL) and the mixture was refluxed for 3 hr. After the completion of the reaction of 5, the reaction mixture was cooled to room temperature and it was added to a mixed solution of THF and HaO, and the organic layer was separated and dried with MgS 4 and then concentrated. Finally, the obtained product was purified by column chromatography, and recrystallized from ethyl acetate / n-hexane to afford compound (1. MS [M+H] 937. 10 &lt;Example 15&gt; The compound of formula 113 was prepared by the compound of formula d (1.00 g; 2.08 mmol), diphenylamine (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; 18·7 mmol) added to xylene (40 ml 15 liters), and the reaction mixture was refluxed for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and it was added to a mixed solution of THF and H20, and the organic layer was separated and dried with MgS04, followed by concentration. Finally, the obtained product was purified by a two-column chromatography, and recrystallized from ethyl acetate/n-hexane to afford compound 20 (1.16 g; 75°/). ; MS [M+H] 745. &lt;Example 16&gt; The compound of the formula 114 was prepared by the compound of the 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 third-butoxy 71 1294454 sodium (sodium tert-butoxide, 1.80 g) ; 18.7 mmol) was added to xylene (40 mL) and the reaction mixture was refluxed for 3 hr. After the completion of the reaction, the reaction mixture was cooled to room temperature, and added to a mixed solution of THF and H20, and the organic layer was separated and dried with MgS04, and then concentrated. Finally, the obtained product was purified by column chromatography, and recrystallized from ethyl acetate / n-hexane to afford compound (1.46 g; 79%). MS [M+H] 895. &lt;Example 17&gt; The compound of the formula 115 was prepared by the compound of the formula d (1·00 g; 2·08 mmol), N-phenyl-2-10-naphthylamine (1·50 g; 6.86) Ment), Pd2(dba)3 (0·125 g; 0·13 mmol), P(t-Bu)3 (0.04 g; 0·2 mmol), and sodium tert-butoxide (sodium tert-butoxide) 1.80 g; 18.7 mmol) was added to xylene (40 mL) and the reaction mixture was refluxed for 3 h. After the completion of the reaction, the reaction mixture was cooled to room temperature, and added to a mixture of THF and 15 and H.sub.2, and the organic layer was separated and dried with &lt;RTIgt; Finally, the obtained product was purified by column chromatography, and recrystallized from ethyl acetate / n-hexane to give the compound of formula 115 (1·21 g; 65%); MS [M +H] 895. &lt;Example 18&gt; Preparation of Compound 20 represented by Formula 116 Compound (d.克; 0·21 mmol), P(t-Bu)3 (0.66 g; 0·31 mmol), and sodium tert-butoxide (1.05 g; 10.96 mmol) were added. Diphenylbenzene (30 liters), and the reaction mixture was refluxed for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and it was added to a mixed solution of THF and H20, and the organic layer was separated and dried over MgS04, and then concentrated. Finally, the obtained product was purified by column chromatography, and recrystallized from ethyl acetate / n-hexane to afford compound (yield: 1.62 g; 66%) of formula 116; M+]H] 787. &lt;Example 19 &gt; Preparation of the compound of the formula 120 The compound of the formula d (1·50 g; 3·13 mmol), Ν·(3-mercaptophenyl)-1-naphthylamine ( 2.40 g; 10.3 mmol), Pd2(dba)3 (0.19 g; 0.21 mmol), P(t-Bu)3 (0.66 g; 0.31 mmol), and the third-10 sodium tert-butoxide , 1.05 g; 10.96 mmol) was added to xylene (30 mL) and the reaction mixture was refluxed for 3 hr. After the completion of the reaction, the reaction mixture was cooled to room temperature, and added to a mixed solution of THF and H20, and the organic layer was separated and dried with &lt;RTIgt; Finally, the obtained product was purified by column chromatography, and recrystallized from ethyl acetate/n-hexane to afford compound (yield: 1.92 g; 65%). MS [M+H] 937. &lt;Example 20 &gt; Preparation of a compound of the formula 121: Compound (m.p. 1.50 g; 3.13 mmol), N-(3-methylphenyl)-2-naphthylamine (2·40 g; 10.3 mmol), Pd2(dba)3 (0·19 20 g; 0.21 mmol), P(t-Bu)3 (0.66 g; 0·31 mmol), and sodium tert-butoxide (sodium tert_butoxide, 1.05 g; 10.96 mmol) was added to xylene (30 mL), and the reaction mixture was refluxed for 3 hr. After the completion of the reaction, the reaction mixture was cooled to room temperature, and added to a mixed solution of THF and H20, and the organic layer was separated and dried, dried, and then concentrated. Finally, the obtained product was purified by column chromatography, and recrystallized from ethyl acetate/n-hexane to afford compound (1·92 g; 65%). MS [M+H] 937. &lt;Example 21 &gt; Preparation of Compound 5 represented by Formula 192 (1) The compound of the formula (5·0 g; 15.38 mmol) and di-tert-butyl-dicarbonate (di-tert-butyl-dicarbonate, 5.04 g; 23.08 mmol) was dissolved in 50 mL of THF and 4-(didecylamino)pyridine (0.19 g; 1. 54 mmol). Then, the reaction mixture was allowed to react at room temperature for 24 hours. After the reaction was completed, the reaction mixture was concentrated and recrystallized from ethyl alcohol to give a product (6.16 g; 94%). (2) The product obtained in Step 1 (6·16 g; 14.49 mmol), diphenylamine (5·89 g; 34.78 mmol), Pd2 (dba) 3 (0.17 g; 0·29 mmol), P ( t-Bu)3 (0.66 g; 0.29 mmol), and sodium tert-butoxide (4.18 g; 43.47 mmol) were added to diphenylbenzene (30 mM 15 liters). And the reaction mixture was refluxed for 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, and the organic layer was separated and dried with MgSO 4 and then concentrated. Finally, the obtained product was purified by column chromatography, and recrystallized from ethyl acetate / n-hexane to afford a product (5.88 20 g; 67%). (3) The product obtained in 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 hr. After the reaction mixture was cooled to room temperature, the reaction was quenched with aqueous NaOH and extracted with dichloromethane (MC) and then washed with water. Next, to 74 1294454

The obtained product was dried by MgSCU, and the solvent was evaporated to dryness. Finally, the crude product (ethyl acetate / n-hexane = 1 / 9) was purified by column chromatography to give a compound (2.9 g; 59%). (4) The product obtained in the step 3 (2.9 g; 5.78 mmol), 4-phenyl bromide-diphenylamine (1·36 g; 4·21 mmol), Pd2(dba)3 (0·05)克; 0·084 mmol), p(t-Bu)3 (0·017 g; 0.084 mmol), and sodium tert-butoxide (1.21 g; 12·63 mmol) added to xylene (30 ml), and the reaction mixture was refluxed for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and added to a mixed solution of 10 THF and H 2 hydr., and the organic layer was separated and dried with Mg?? Finally, the obtained product was purified by column chromatography, and recrystallized from ethyl acetate/n-hexane to give the compound of formula 192 (1.5 g; 49%). MS [M+H] 745. &lt;Example 22 &gt; Preparation of Compound 15 represented by Formula 193 (1) Compound of the formula e (5.0 g; 15.38 mmol) and di-tert-butyl-dicarbonate (di-tert-butyl-dicarbonate) , 5.04 g; 23.08 mmol) was dissolved in 50 mL of THF and 4-(dimethylamino)indole (0.19 g; 1.54 mmol). Then, the reaction mixture was placed in a chamber at room temperature for 24 hours. After the reaction was completed, the reaction mixture was concentrated and 20 was recrystallized from ethanol to give a product (6.16 g; 94%) ??? (2) The product obtained in Step 1 (6.16 g; 14.49 mmol) 'N&quot; 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; 〇.29 mmol) were added to 75 8 1294454 xylene (30 ml), and the reaction mixture was refluxed for 3 hr. After the completion of the reaction, the reaction mixture was cooled to room temperature, and added to a mixed solution of THF and H20, and the organic layer was separated and dried with Mg. Finally, the obtained product 5 was purified by column chromatography and recrystallized from acetic acid to give a product (6.0 g; 59%). (3) The product obtained in the 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. After the reaction mixture was cooled to room temperature, the reaction was quenched with aqueous NaOH and extracted with dichloromethane (MC) and then washed with water. Next, the obtained product was dried with MgS04, and the solvent was evaporated to dryness. Finally, the crude product (ethyl acetate / n-hexane = 1 / 9) was purified by column chromatography to give a compound (3.8 g; 74%). (4) The product obtained in Step 3 (3.8 g; 6.31 mmol), 4-bromo 15-phenyl-N-phenyl-1-naphthylamine (1·57 g; 4·21 mmol), Pd2. (dba) 3 (0.55 g; 0.084 mmol), P(t-Bu)3 (0.017 g; 0.084 mmol), and sodium telrt-butoxidib (1. 21 g; 12.63 mmol) It was added to diphenylbenzene (30 ml), and the reaction mixture was refluxed for 3 hr. After the completion of the reaction, the reaction mixture was cooled to room temperature, and 20 was added to a mixed solution of THF and H20, and the organic layer was separated and dried over MgS04, and then concentrated. Finally, the obtained product was purified by column chromatography, and recrystallized from ethyl acetate/n-hexane to give the compound of formula 193 (1.2 g; 32%); MS[M +H] 895. 76 25 1294454 &lt;Example 23 &gt; Preparation of Compound (1) represented by Formula 194 The compound of the formula e (5.0 g; 15.38 mmol) and di-tert&gt;butyl-dicarbonate (di-tert&gt; 5·04 g; 23.08 mmol) was dissolved in 50 ml of THF, and 4-(dimethylamino) 5 pyridine (0.19 g; 1.54 mmol) was added. Then, the reaction mixture was allowed to react at room temperature for 24 hours. After completion of the reaction, the reaction mixture was concentrated and recrystallized from ethanol to give a product (6.16 g; 94%). (2) The product obtained in the step 1 (6·16 g; 14.49 mmol), N-phenyl-2-naphthylamine (7·63 g; 34.78 mmol), and the third. Sodium butoxide (Sodium 10 tert_butoxide, 4.18 g; 43.47 mmol), Pd2 (ciba) 3 (0.17 g; 0.29 mmol), and P(t-Bu)3 (0.66 g; 0.29 mmol) were added to xylene ( In 30 ml), and the reaction mixture was refluxed for 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, and the organic layer was separated and dried over MgS04, and then concentrated. Finally, the obtained product was purified by column chromatography, and recrystallized from ethyl acetate/n-hexane to afford a product (6.0 g; 59%). (3) The product obtained in the 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. After reacting the mixture to room temperature, the reaction was quenched with aqueous NaOH and extracted with dichloromethane (MC) and then washed with water. Next, the obtained product was dried with MgS04, and the solvent was evaporated to dryness. Finally, the crude product (ethyl acetate / n-hexane = 1/9) was purified by column chromatography to give a compound (3.8 g; 74%). 77 1294454 (4) The product obtained in Step 3 (3·8 g; 6.31 mmol), 4-bromophenyl-N-phenyl-2-naphthylamine (1.57 g; 4·21 mmol), Pd2 (dba) 3 (0.05 g; 0.084 mmol), P(t-Bu)3 (0·017 g; 0.084 mmol), and sodium tert-butoxide (1. 21 g; 12.63 5 mmol) Into xylene (30 mL), and the mixture was refluxed for 3 h. After the completion of the reaction, the reaction mixture was cooled to room temperature, and added to a mixed solution of THF and H20, and the organic layer was separated and dried with Mg?? Finally, the obtained product was purified by column chromatography and subjected to 10 recrystallization in ethyl acetate / n-hexane to give the compound of formula 194 (1.2 g; 32%); M+H] 895 〇&lt;Example 24&gt; Preparation of the compound of the formula 197 (1) The compound of the formula e, (5.0 g; 15.38 mmol) and di-tert-butyl dicarbonate (di-tert) -butyl-dicarbonate, 5.04 g; 23.08 15 mmol) was dissolved in 50 mL of THF and 4-(didecylamino)pyridine (0.19 g; 1.54 mmol). Then, the reaction mixture was allowed to react at room temperature for 24 hours. After the reaction was completed, the reaction mixture was concentrated and recrystallized from ethanol to give a product (6.16 g; 94%). (2) The product obtained in Step 1 (6.16 g; 14.49 mmol), 3-20 mercapto-diphenylamine (6.37 g; 34.78 mmol), and 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 diphenylbenzene (30 ml), and the reaction mixture was refluxed 3 hour. After the completion of the reaction, the reaction mixture was cooled to room temperature, and added to a mixture of THF and a mixture of 78 1294454 and H20, and the organic layer was separated and dried over MgS04 and then concentrated. Finally, the obtained product was purified by column chromatography, and recrystallized from ethyl acetate/n-hexane to afford a product (6.3 g; 69%). 5 (3) The product obtained in Step 2 (6.3 g; 10.0 mmol) was dissolved in trifluoroacetic acid/chloroform (50 ml / 50 ml), and the solution was refluxed for 3 hours. After the reaction mixture was cooled to room temperature, the reaction was quenched with aqueous NaOH and extracted with dichloromethane (MC) and then washed with water. Next, the obtained product was dried with MgS04, and the solvent was evaporated to dryness. Finally, the crude product (ethyl acetate / n-hexane = 1 / 9) was purified by column chromatography to give a compound (3·8 g; 71%). (4) The product obtained in Step 3 (3.8 g; 7.17 mmol), 4-bromophenyl-(3-methyl)-diphenylamine (1·42 g; 4-21 mmol), Pd2(dba)3 ( 0.05 g; 0.084 mmol), P(t_Bu)3 (0.017 g; 0.084 mmol), 15 and sodium tert-butoxide (1.21 g; 12.63 mmol) added to xylene (30 ml) The reaction mixture was refluxed for 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, and the organic layer was separated and dried over MgS04, and then concentrated. Finally, the obtained product was purified by column chromatography, and recrystallized from ethyl acetate / n-hexane to give the compound of formula 197 (1.2 g; 36%); MS[M +H] 787. &lt;Example 25&gt; The compound (1) represented by the formula 218 was prepared by the compound of the formula (5.0 g; 15.38 mmol) and the di-tert-butyl-dicarbonate (di-tert-butyl-dicarbonate). • 4 g, 23.08 mmol) was dissolved in 50 mL of THF and 4-(dimethylamino) 17-pyridine (0.19 g; 1.54 mmol) was added. Then, the reaction mixture was allowed to stand at room temperature for 24 hours. After the reaction was completed, the reaction mixture was concentrated and recrystallized from ethyl alcohol to give a product (6·16 g; 94%). (2) The product obtained in Step 1 (6.16 g; 14.49 mmol), diphenylamine (5.89 g; 34.78 mmol), sodium tert-butoxide (4·18 g; 43.47 mmol), Pd2 ( Dba) 33 (0·17 g; 〇.29 mmol), and P(t-Bu)3 (0·06 g; 〇.29 mmol), added 10 to toluene (30 ml), and the reaction mixture was refluxed for 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, and the organic layer was separated and dried over MgS04, and then concentrated. Finally, the obtained product was purified by column chromatography, and recrystallized from ethyl acetate / n-hexane to afford a product (5.88 g; 67%). (3) The product obtained in Step 2 ( 5.88 g; 9.77 mmol) was dissolved in &lt;RTIgt;&lt;/RTI&gt;&gt; trifluoroacetic acid/chloroform (50 ml / 50 ml) and the solution was refluxed for 3 hours. After the reaction mixture was cooled to room temperature, the reaction was quenched with aqueous NaOH and extracted with dichloromethane (MC) and then washed with water. Next, the obtained product was dried at 20 MSs 〇4, and the solvent was evaporated to dryness. Finally, the crude product (ethyl acetate / n-hexane = 1 / 9) was purified by column chromatography to give a compound (2·9 g; 59%). (4) The product obtained in the step 3 (2.9 g; 5.78 mmol), 4· desertified phenylsulfonyl _i_naphthylamine (ι·57 g; 4.21 mmol), Pd2 (ciba) 3 (0.05

80 1294454 g; 0.084 mmol), P(t-Bu)3 (〇·〇17 g; 0·084 mmol), and sodium tert-butoxide (1.21 g; 12.63 mmol) were added to the second Intoluene (30 mL), and the reaction mixture was refluxed for 3 hr. After completion of the reaction, the anti-friction mixture was cooled to room temperature, and 5 was added to a mixed solution of THF and H20, and the organic layer was separated and dried with Mg?? Finally, the obtained product was purified by column chromatography, and recrystallized from ethyl acetate/n-hexane to afford compound of formula 218 (1.5 g; 49%); MS[M+H 795 〇10 &lt;Example 26&gt; The compound (1) represented by the formula 219 was prepared as a compound of the formula (5.0 g; 15-38 mmol) and di-tert-butyl-dicarbonate (di-tert-butyl-dicarbonate). 5·〇4 g; 23.08 mmol) was dissolved in 50 ml of THF, and 4-(didecylamino)pyridine (〇·19 g; 1.54ππηο1) was added. Then, the reaction mixture was allowed to react at room temperature for 15 hours. After the reaction was completed, the reaction mixture was concentrated and recrystallized from ethanol to give a product (6.16 g; 94%). (2) The product obtained in the first step (6·16 g; H.49 mmol), Ν-phenyl-2-naphthylamine (7.63 g; 34.78 111111〇1), and the third-butoxysodium oxide (3〇4) ^1111 tert_butoxide, 4·18 g; 43.47 mmol), Pd2(dba)3 (0.17 g; 20 0.29 mmol), and P(t-Bu)3 (0.66 g; 〇·29 mmol) were added to In xylene (30 mL), the reaction mixture was refluxed for 3 h. After the completion of the reaction, the reaction mixture was cooled to room temperature, and added to a mixed solution of THF and H20, and the organic layer was separated and dried with MgSCU, and then concentrated. Finally, the obtained (S) 1294454 product was purified by column chromatography, and recrystallized from ethyl acetate / n-hexane to afford a product (6.0 g; 59%). (3) The product obtained in the 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. After the mixture was cooled to room temperature, the reaction was quenched with aqueous Na.sub.2H and extracted with dichloromethane (MC) and then washed with water. Next, the obtained product was dried with MgS04, and the solvent was evaporated to dryness. Finally, the crude product (ethyl acetate / n-hexane = 1 / 9) was purified by column chromatography to give a compound (3·8 g; 74%). 10 (4) The product obtained in Step 3 (3·8 g; 6.31 mmol), 4-bromophenyl-N-phenyl-1-naphthylamine (1.57 g; 4.21 mmol), Pd2 (dba) 3 ( 0.05 g; 0.084 mmol), P(t-Bu)3 (0·017 g; 0.084 mmol), and sodium tert-butoxide (1.21 g; 12.63 mmol) added to xylene (30 ml), and the reaction mixture was refluxed for 3 15 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, and the organic layer was separated and dried over MgS04, and then concentrated. Finally, the obtained product was purified by column chromatography, and recrystallized from ethyl acetate/hexane solution to obtain a compound of formula 219 (1.2 g; 32%); [M+H] 20 895 〇 &lt;Example 27 &gt; Preparation of the compound of formula 252 The compound of formula c (1.00 g; 2.08 mmol), triphenylamine-4·boric acid (1.99 g; · 87 mmol), 2M potassium carbonate solution (10 ml), and tetrakis(triphenylphosphine) palladium

82 1294454 (tetrakis(triphenylphosphine) palladium, 〇·〇7 g; 〇·〇 6 mmol) was added to 40 ml of THF, and the reaction mixture was stirred under reflux for 24 hr then cooled to room temperature. Next, the reaction mixture was introduced into toluene and brine, and the toluene layer was separated. The separated toluene layer was dried over MgS04 5 and filtered and concentrated. Finally, the reaction mixture was purified by column chromatography to give the compound of formula 252 (1.15 g; 55%) as starting material. lHNMR (300 MHz, CDCl3) 6.76-6.82 (m, 18H), 6.92-6.95 (m, 6H), 7.31-7.35 (m, 12H), 7·53-7·60 (ιη, 1〇H), 7 · 76-8·07 (χη, 6H); MS [M+H] 973. 1〇&lt;;Example 28&gt; Preparation of Organic Electroluminescent Device A glass substrate coated with a 1000 A thick ITO (Indium Tin Oxide) film on one surface, immersed in a distilled water containing detergent, and using ultrasonic waves The substrate is washed. The cleaning agent used in this example was a product purchased by Fisher's and the steamed water used was obtained by two filtrations of a 15 filter commercially available from Millipore. After washing the ITO for 30 minutes, the washing was repeated twice by ultrasonic waves for 10 minutes by means of distilled water. After the steaming water washing is completed, isopropanol, acetone, and methanol are sequentially used to wash the ultrasonic waves. Next, the obtained substrate was dried and transferred as a plasma cleaner. Then, the substrate was cleaned by oxygen plasma for 5 minutes, and then transferred to a vacuum deposition apparatus. In the preparation of the above ITO transparent electrode (first electrode), the compound of the above formula 61 is coated with a thickness of 600 A by thermal vacuum deposition, thereby forming a hole injection layer. Next, an NPB as a hole transport layer is coated with a thickness of 400 A on the hole injection layer by vacuum deposition. Further, Alq3, which is 83 (S) 1294454 as a light emission/electron injection/electron transport material, is coated with a thickness of 500 A on the NPB by vacuum deposition to complete the formation of an organic material film. On the Alq3 layer, lithium fluoride (LiF) and aluminum were each produced in a continuous vacuum deposition manner to have a thickness of 15A and 2500A to form a cathode 5 (second electrode). In the above process, the deposition rate of each organic material is maintained between 0.5 and 1.0 A/sec, and the deposition speeds of lithium fluoride and aluminum materials are each maintained at 0·2 A / sec, and 2 to 3 A / sec. . The organic electroluminescence device obtained in this example showed a spectrum having an electric excitation light of 3.87 cd/A under the operation of a forward electric field of a current density of 7.17 V and a current density of 100 mA/cm2. &lt;Example 29&gt; Preparation of organic electroluminescent device In the preparation of the ITO transparent electrode (first electrode) of the above Example 28, the compound of the above formula 61 was coated by a vacuum deposition to a thickness of 800 A. Thus, a hole injection layer is formed. Next, an NPB as a transmission layer of the hole 15 is coated with a thickness of 400 A on the hole injection layer by vacuum deposition. Further, Alq3 as a light radiation/electron injection/electron transport material is coated with a thickness of 300 A on the NPB by vacuum deposition to complete the formation of the thin film of the organic material. The remaining process steps are the same as in Example 28. The organic electroluminescence device obtained in this example exhibited a spectrum having an electric excitation light of 3.86 cd/A under the operation of a forward electric field of a current density of 7.8 V and a current density of 100 mA/cm2. &lt;Example 30&gt; Preparation of organic electroluminescent device Repeat the procedure of Example 28 for preparing an organic electroluminescent device, except

84 1294454 A compound of the formula 63 above is used in place of the compound of the formula 61. The organic electroluminescence device obtained in this example exhibited a spectrum having an electric excitation light of 3.8 cd/A under the operation of a forward electric field of a current density of 7.8 V and a current density of 100 mA/cm2. 5 &lt;Example 31 &gt; Preparation of organic electroluminescent device The procedure of preparing an organic electroluminescent device was repeated as in Example 28 except that the compound of the above formula 64 was used instead of the compound of the formula 61. The organic electroluminescent device obtained in this example exhibited a spectrum having an electric excitation light of 3.61 cd/A under the operation of a forward electric field of a current driving voltage of 100 mA/cm2. &lt;Example 32&gt; Preparation of organic electroluminescent device The procedure of preparing an organic electroluminescent device was repeated as in Example 28 except that the compound of the above formula 69 was used instead of the compound of the formula 61. The organic electroluminescence device obtained in this example showed a spectrum having an electric excitation light of 3.82 cd/A under the action of a forward electric field of a current density of 8.0 V and a current density of 100 mA/cm2. &lt;Example 33 &gt; Preparation of organic electroluminescent device The procedure of preparing an organic electroluminescent device was repeated as in Example 28 except that the compound of the formula 71 was substituted for the compound of the formula 61. The organic electroluminescence device obtained in this example exhibited a spectrum having an electric excitation light of 4.4 cd/A under the operation of a forward electric field of a current density of 7.6 V and a current density of 100 mA/cm2. &lt;Example 34&gt; Preparation of organic electroluminescent device The procedure of preparing an organic electroluminescent device was repeated as in Example 28 except that the compound of the above formula 72 was used in place of the compound of the formula 61. The organic electroluminescence device obtained in this example exhibited a spectrum having an electric excitation light of 4.3 cd/A under the operation of a forward electric field of a current density of 7.8 V and a current density of 100 mA/cm2. 5 <Example 35 &gt; Preparation of organic electroluminescent device The procedure of preparing an organic electroluminescent device was repeated as in Example 28 except that the compound of the above formula 89 was used instead of the compound of the formula 61. The organic electroluminescence device obtained in this example showed a spectrum having an electrical excitation light of 4.3 cd/A under the operation of a forward electric field of a current density of 7.5 V and a current density of 100 mA/cm2. &lt;Example 36&gt; Preparation of organic electroluminescent device The procedure of preparing an organic electroluminescent device was repeated as in Example 28 except that the compound of the above formula 95 was used instead of the compound of the formula 61. The organic electroluminescence device obtained in this example exhibited a spectrum having an electrical excitation light of 4.5 cd/A under the operation of a forward electric field of a current density of 7.5 V and a current density of 100 mA/cm2. &lt;Example 37&gt; Preparation of organic electroluminescent device The procedure of preparing an organic electroluminescent device was repeated as in Example 28 except that the compound of the above formula 96 was used instead of the compound of the formula 61. The organic electroluminescence device obtained in this example exhibited a spectrum having an electric excitation light of 4.4 cd/A under the operation of a forward electric field of a current density of 7.2 V and a current density of 100 mA/cm2. &lt;Example 38&gt; Preparation of organic electroluminescent device The procedure of preparing an organic electroluminescent device was repeated as in Example 28 except that the compound of the above formula 113 was used in place of the compound of the formula 61. The organic electroluminescent device obtained in this example exhibited a spectrum having an electric excitation of 4.2 cd/A under a 7.7 V driving voltage and a current density of 100 mA/cm2. 5 &lt;Example 39&gt; Preparation of organic electroluminescent device The procedure of preparing an organic electroluminescent device was repeated as in Example 28 except that the compound of the above formula 114 was used instead of the compound of the formula 61. The organic electroluminescent device obtained in this example exhibited a spectrum having an electric excitation light of 4.1 cd/A under the operation of a forward electric field of a current density of 7.6 V and a current density of 100 mA/cm2. &lt;Example 40 &gt; Preparation of organic electroluminescent device The procedure of preparing an organic electroluminescent device was repeated as in Example 28 except that the compound of the above formula 120 was used instead of the compound of the formula 61. The organic electroluminescence device obtained in this example exhibited a spectrum having an electric excitation light of 3.98 cd/A under the operation of a forward electric field of a current density of 7.8 V driving 15 voltage and 100 mA/cm 2 . &lt;Example 41 &gt; Preparation of organic electroluminescent device In the preparation of the ITO transparent electrode (first electrode) of the above Example 28, the compound of the above formula 192 was coated with a thickness of 800 A via thermal vacuum deposition. 20 degrees, thus forming a hole injection layer. Next, an NPB as a hole transport layer is coated with a thickness of 300 A on the hole injection layer by vacuum deposition. Further, Alq3 as a light radiation/electron injection/electron transport material was coated with a thickness of 300 A on the NPB by vacuum deposition to complete the formation of the film of the organic material. And the remaining process steps are the same as the embodiment

87 1294454 28 The organic electroluminescent device obtained in the present embodiment exhibits a spectrum having an electrical excitation light of 3.7 cd/A under a 6.7 V driving voltage and a forward electric field of a current density of 100 mA/cm 2 . . 5 &lt;Example 42&gt; Preparation of organic electroluminescent device The procedure of preparing an organic electroluminescent device was repeated as in Example 41 except that: The compound of the formula 193 was used instead of the compound of the formula 192. The organic electroluminescent device obtained in this embodiment exhibits a 3.6 ?d/A electrical excitation at a 6.9V driving electric current (: a voltage, a forward electric field of a current density of 100 mA/cm2). Spectrum of Light. <Example 43> Preparation of Organic Electroluminescent Device The procedure of preparing an organic electroluminescent device was repeated as in Example 41 except that the compound of the above formula 194 was used instead of the compound of the formula 192. The organic electroluminescent device obtained in the example showed a spectrum having an electrical excitation light of 3.5 cd/A under operation of a forward electric field of a current density of 6.8 V and a current density of 100 mA/cm 2 . 44 &gt; Preparation of Organic Electroluminescent Device The procedure of preparing an organic electroluminescent device was repeated in Example 41 except that the compound of the above formula 197 was used instead of the compound of the formula 192. -20 obtained in this example An organic electroluminescent device exhibits a spectrum having an electrical excitation light of 3.9 cd/A at a driving current of 6.9 V and a forward electric field of a current density of 100 mA/cm2. &lt;Example 45 &gt; Preparation Electromechanical excitation device repeat The preparation of an organic electroluminescent device is carried out in the same manner as in Example 41 except that the compound of the above formula 218 is used in place of the compound of the formula 192. The organic electroluminescent device obtained in this embodiment has a driving voltage of 6.8 V. Under the operation of a forward electric field of a current density of 100 mA/cm2, a spectrum having an electric excitation light of 3.8 cd/A was shown. 5 &lt;Example 46&gt; Preparation of Organic Electroluminescent Device Repeating Example 41 Preparation of an Organic Electrode The step of exciting the optical device, except that the compound of the above formula 219 is used instead of the compound of the formula 192. The organic electroluminescent device obtained in this embodiment has a current density of 6.8 V and a current density of 100 mA/cm 2 . Under the operation of the forward electric field, a spectrum having an electric excitation light of 3.6 cd/A is shown. &lt;Example 47&gt; Preparation of Organic Electroluminescence Device: The procedure of preparing an organic electroluminescence device in Example 41 was repeated. In addition to the use of the compound of the above formula 252, in place of the compound of the formula 192. The organic electroluminescent device obtained in this example, a forward current of a current density of 100 mA/cm2 at a voltage of 6.88V. Under the operation of the field, a spectrum having an electrical excitation light of 3.2 cd/A is shown. It can be seen from the above embodiments that the organic electroluminescent device using the compound of the present invention as a hole injecting material has a driving voltage of 6.88V. An operation of a forward electric field of 100 20 mA/cm2 current density provides an excellent electroluminescence effect of 3.2 to 4.5 cd/A. In other words, a crucible containing a hole transport material and Alq3 In the organic electroluminescence device as a light emission/electron injection/electron transport material, when the compound of the present invention is used as a material for a hole injection layer, the present invention can effectively improve the effect of the electric 25 excitation light as compared with the conventional device. 89 1294454 It is known from the above that when the novel compound of the present invention is applied to an organic compound layer contained in an organic electroluminescent (el) device of a light-emitting device, the performance of the excitation light and its lifetime can be improved. Thus, the compounds of the invention can be used in the field of devices comprising organic electroluminescent devices. ~ [Simple description of the diagram] Figure 1 is a schematic diagram of the structure of a conventional organic electroluminescent device 10 [Description of main components] 1 substrate 2 anode 3 hole injection layer 4 pen hole transmission layer 5 organic electroluminescence layer 6 electron transmission 7 cathode stomach

Claims (1)

1294454 X. Patent application scope: 1. A compound of the following formula 1: ,Formula 1 R2 wherein A is a [R1 - N-], 5 is a [R3-N-], or a [R3-N-Ar-]; C is a [R5-N-], R6 Re R10 or -Ar-] ; D is Η, -[R7-N-], or a [R9-N-Ar-]; R1 to R10 are the same or different and each contain at least one of at least one time a group selected from the group consisting of hydrogen atoms; an aliphatic hydrocarbon having 1 to 20 carbon atoms; unsubstituted or substituted with a mononitro, nitroso, halogen, /0 alkyl, alkoxy or amine group An aromatic hydrocarbon; an anthracene group having an aryl group substituted; a heterocyclic aromatic group which is unsubstituted or substituted with a mononitro group, a nitroso group, a dentate element, an alkyl group, an alkoxy group or an amine group; a hydrocarbon; a thiophenyl group substituted with a C! to C2G hydrocarbon, or a €:6 to &lt;:24 aromatic hydrocarbon; and a 15 group consisting of a boron group substituted with an aromatic hydrocarbon Group; Ar is an unsubstituted or aromatic hydrocarbon substituted with a stone succinyl, nitroso, halogen, alkyl, oxy or amine group; each of the 1, m, and η is one Or a count greater than 1' The lanthanide is a 0 wei 91 1294454 an integer greater than 0; and the R!, R2, R3, R4, R5, R6, and D of the compound of Formula 1 are not simultaneously a hydrogen atom. 2. The compound according to claim 1, wherein the aromatic hydrogen barrier compound comprises phenyl, biphenyl, terphenyl, 5 naphthyl, anthracenyl, phenanthrene. , pyrenyl, and perylenyl. 3. The compound according to claim 1, wherein the heterocyclic aromatic hydrocarbon comprises porphin, sigma, σ ratio 11 (pyrrole), imidazole, mouth plug Thiazole, oxazole, 10 oxadiazole, thiadiazole, triazole, pyridyl, 11 唆11 Pyridazyl), pyrazine, quinoline, and isoquinoline 〇4. The compound of claim 1, wherein the compound 15 is any Free group of the following formula 2a to 2e: (s) 20 1294454 Equation 2c, Equation 2d, and Here, each of m, n, o, and R1 to R8 is the same as defined in item 1 of the patent application range. 5. The compound of claim 1, wherein the compound is any compound selected from the group consisting of the following formula 3a to formula 3: 10 1294454 Equation 3c, Equation 3d, 94 1294454 Wherein, each of R1 to R8 is the same as defined in item 1 of the scope of the patent application. 6. The compound according to claim 1, wherein the compound represented by the formula 1 is any one selected from the group consisting of the following formulas 3a to 3n: 95 1294454 Equation 64, Equation 63, Equation 66, (R) 96 1294454 Equation 71, Equation 72, Equation 73, 74, 97 1294454 Equation 78, 98 1294454 99 1294454 100 (8) 1294454 8 1294454 Formula 93, Formula 94, Formula 97, Formula 98, 102 1294454 5 formula 101, 103 (S) 1294454 Equation 106, ρο φο Formula 107, Formula 111, formula 112, (8 104 1294454 OMe OMe Rs\ 105 1294454 Formula 123, Equation 124, 125, OMe OMe 126, 106 (s) 1294454 127, 1294454 133, Formula 135, Equation 136, 108 1294454 Σο , ςο 109 1294454 OMe OMe Equation 145, 150, OMe OMe Equation 151 OMe OMe style 152, (s) 1294454 OMe OMe OMe OMe 154, 153, 156, 155, Formula 158, 159, OMe OMe 160, 111 1294454 Formula 163, 112 10 1294454 113 1294454 Formula 181, formula 182, 186, 187, 188, 114 1294454 189, 190, 191, 198, 199, 200, 10 1294454 OMe 10 type 208, type 209, type 210, 116 1294454 Equation 211, Equation 215, formula 216, 217, 218, 219, 117 1294454 220, 221, 222, 223, 224, 225, Equation 226, and Equation 227. An organic electro-excitation device comprising: a first electrode; a second electrode; and one or more organic compound layers between the electrodes; wherein at least one organic compound layer comprises At least as claimed in any one of the first to sixth shots of the specific range. The organic compound layer of the compound described in any one of the first to sixth aspects of the patent range 1 to 6 is a hole injection/electricity with a hole injection and a hole transmission function. The hole passes through the wheel. The organic electroluminescent device of claim 7, wherein the organic compound layer containing at least one of the compounds of any one of claims 5 to 6 of the patent application, It is a hole injection/hole transmission/electric excitation layer with electrical connection, electric hole, transmission and illumination function. The organic electroluminescent device according to the seventh aspect of the invention, wherein the organic compound layer of the compound according to any one of claims [6 to 6] is It is a 10 hole injection layer with a hole injection function. 11. The organic electroluminescent device according to claim 7, wherein the substrate comprises a substrate, an anode, a hole injection layer, a hole transport layer, an organic electroluminescent layer, An electron transporting layer, and a cathode, wherein the organic compound layer containing at least one of the compounds of any one of clauses 1 to 6 of the patent application is at least one selected from the group consisting of the hole injection layer, a hole transport layer and a group of the electroluminescent layers. 119