KR20130118269A - Aromatic compound and organoelectroluminescent device comprising the compound - Google Patents

Abstract

PURPOSE: An aromatic compound and an organic electroluminescent device containing the same are provided to show stability and superior light emitting properties such as low driving voltage or current efficiency. CONSTITUTION: An aromatic compound is denoted by chemical formula 1. An organic electroluminescent device comprises a first electrode, a second electrode, and one or more organic layers between the first and second electrodes. The organic layers contain one or more aromatic compounds. The organic layers are selected among a hole injection layer, a hole transport layer, a functional layer with hole injecting and transporting functions, a light emitting layer, an electron transport layer, and an electron injection layer. The light emitting layer contains one or more host compounds and dopant compounds.

Description

Aromatic compound and organoelectroluminescent device comprising the compound

The present invention relates to an aromatic compound and an organic electroluminescent device using the same, wherein the organic electroluminescent device comprising the aromatic compound according to the present invention has a low driving voltage and excellent luminous efficiency.

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

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

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

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

Organic electroluminescent devices have been increasingly applied to display and illumination fields of various electronic products. However, efficiency and lifetime characteristics are limiting the expansion of application fields. In order to improve efficiency and lifetime characteristics, Many studies are under way. In terms of materials, the host-dopant system is mainly adopted as a method for maximizing luminous efficiency, and the dopant as a luminescent material is a phosphorescent material, and CBP (4,4'-N, N'-dicarbazolbiphenyl) and substances in which various substituents are introduced into carbazole (Japanese Patent Laid-Open No. 2008-214244, Japanese Patent Laid-Open No. 2003-133075) are known, but further improvement is required in terms of efficiency and lifetime characteristics.

The problem to be solved by the present invention is to provide a novel aromatic compound and an organic light emitting device capable of low voltage drive, including the same, and having excellent luminous efficiency and life characteristics.

The present invention provides an aromatic compound represented by the following [Formula 1] to solve the above problems.

[Formula 1]

In addition, the present invention provides an organic electroluminescent device having an anode, a cathode, and an organic material layer interposed between the anode and the cathode and including an aromatic compound represented by the above [Formula 1].

The specific substituent of the said Formula (1) is mentioned later.

The aromatic compound represented by [Formula 1] according to the present invention is more stable than conventional materials, and has an excellent luminescent property in driving voltage or current efficiency, etc., so that the organic light emitting device including the low voltage can be driven and emit light. The efficiency can be improved.

1 is a schematic view of an organic electroluminescent device according to one embodiment of the present invention.

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

The present invention provides a light emitting layer host material having improved light emission characteristics such as driving voltage, current efficiency, and lifetime characteristics of an organic light emitting diode, and is characterized in that it is an aromatic compound represented by the following [Formula 1].

[Formula 1]

In the above formula (1)

X ₁ to X ₅ are the same as or different from each other, and are each independently selected from N or CR ₁ , provided that at least one of X ₁ to X ₅ is N.

R ₁ is a substituted or unsubstituted C ₁ -C ₃₀ alkyl group, a substituted or unsubstituted C ₆ -C ₄₀ aryl group, a substituted or unsubstituted C ₃ -C ₅₀ heteroaryl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₆ -C ₃₀ aryloxy group, substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, substituted or unsubstituted C ₆ -C ₃₀ aryl Amino group, substituted or unsubstituted C ₁ -C ₂₀ alkylsilyl group, substituted or unsubstituted C ₆ -C ₃₀ arylsilyl group, substituted or unsubstituted C ₁ -C ₅₀ arylalkylamino group, substituted or unsubstituted It may be selected from the group consisting of a substituted C ₂ -C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₄₀ alkynyl group, cyano group, halogen group, small and medium numbers, and hydrogen.

When the R ₁ is a plurality, a plurality of R ₁ is the same as or different from each other, and may be connected to a substituent adjacent to each other to form an alicyclic, aromatic monocyclic or polycyclic ring, wherein the formed alicyclic, aromatic The carbon atom of a monocyclic or polycyclic ring may be substituted with any one or more heteroatoms selected from N, S and O.

R ₂ to R ₁₁ are the same as or different from each other, and each independently hydrogen, deuterium, a C ₁ -C ₂₀ alkyl group, a C ₆ -C ₄₀ aryl group, a C ₃ -C ₅₀ heteroaryl group, C ₁ -C ₂₀ Alkoxy group, C ₆ -C ₃₀ aryloxy group, C ₁ -C ₂₀ alkylamino group, C ₆ -C ₃₀ arylamino group, C ₁ -C ₂₀ alkylsilyl group, C ₆ -C ₃₀ arylsilyl Group, C ₁ -C ₅₀ arylalkylamino group, C ₂ -C ₄₀ alkenyl group, C ₂ -C ₄₀ alkynyl group, cyano group, halogen group, small and medium numbers and hydrogen, Condensed rings may be formed with each other with a substituent.

L is a linking group which is a single bond or a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted carbon atom having 2 to 60 carbon atoms Substituted or unsubstituted C2-C60 alkynylene groups, substituted or unsubstituted C3-C60 alkynylene groups, substituted or unsubstituted C2- Selected from the group consisting of a cycloalkylene group, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms N may be an integer between 1 and 3, and when n is 2 or more, a plurality of Ls may be the same or different.

According to one embodiment of the present invention, R ₂ to R ₁₁ are each independently deuterium, halogen atom, hydroxy group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, phosphoric acid or a salt thereof, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₆₀ a of the cycloalkyl group, C ₅ -C ₆₀ aryl group, an aryloxy group of C ₅ -C _60, C ₅ -C ₆₀ of the coming aryl Im, C ₂ -C ₆₀ heteroaryl group, C ₁ -C ₄₀ alkyl group, C ₆ -C ₄₀ aryl group, a heteroaryl group having a carbon number of C ₃ -C ₄₀ group, may be further substituted with one or more substituents selected from aryl silyl group of the C ₁ -C ₄₀ alkylsilyl group and a C ₆ -C _40.

Meanwhile, the aryl group, which is a substituent used in the present invention, is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and includes a single or fused ring system containing 5 to 7 members, preferably 5 or 6 members. In addition, when there is a substituent on the aryl group may be fused with a neighboring substituent (fused) with each other to further form a ring.

Specific examples of the aryl include phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, 4-methylbiphenyl group, 4- Ethyl biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, 2-naphthyl group, 1-methylnaphthyl group, 2-methylnaphthyl group, anthryl group, phenanthryl group, pyre And aromatic groups such as a silyl group, indenyl, fluorenyl group, tetrahydronaphthyl group, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl and the like.

At least one hydrogen atom of the aryl group may be replaced by a substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a silyl group, an amino group (-NH ₂ , -NH (R) 'And R''each independently represent an alkyl group having 1 to 10 carbon atoms, which is referred to as an "alkylamino group" in this case), an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, A halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, A heteroaryl group having 2 to 24 carbon atoms or a heteroarylalkyl group having 2 to 24 carbon atoms.

The heteroaryl group which is a substituent used in the present invention, in particular, when L is a heteroaryl group which is a divalent linking group as a heteroaryl group, may be any one of substituents selected from the following [formula 1] to [formula 6]. .

[Structural formula 1] [Structural formula 2] [Structural formula 3]

[Structural formula 4] [Structural formula 5] [Structural formula 6]

In the above Structural Formulas 1 to 6,

T ₁ to T ₈ may be the same or different and each independently selected from C (R ₄₁ ), C (R ₄₂ ) (R ₄₃ ), N, N (R ₄₄ ) , R ₃₁ to R ₄₄ are the same or different from each other and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, An aryl group having 5 to 50 carbon atoms, and a heteroaryl group having 2 to 50 carbon atoms having a substituted or unsubstituted heteroatom, O, N or S, and each of [structural formulas 1] to [structural formulas 6], R ₃₁ to R ₄₄ May be bonded to nitrogen in the above formula (1) to form a single bond.

The above-mentioned [formula 3] may include a compound represented by the following formula [3] by a resonance structure according to the movement of electrons.

[Structural Formula 3-1]

In the above structural formula 3-1, T ₁ to T ₅ and R ₃₃ and R ₃₄ are the same as defined above.

Further, according to a preferred embodiment of the present invention, the above Structural Formulas 1 to 6 can be selected from the following Structural Formula 7.

[Structural Formula 7]

In [Formula 7], X is the same as X ₁ to X ₁₄ , m is an integer of 1 to 11, when m is 2 or more, a plurality of X is the same or different from each other, any one of the at least one X May be combined with nitrogen in [Formula 1] to form a single bond.

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

Specific examples of the alkoxy group used in the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isoamyloxy, And may be substituted with the same substituents as those in the case of the alkyl group.

Specific examples of the halogen group which is a substituent used in the compound of the present invention include fluorine (F), chlorine (Cl), bromine (Br) and the like.

The aryloxy group which is a substituent used in the present invention means an -O-aryl radical, wherein the aryl group is as defined above, and specific examples thereof include phenoxy, naphthoxy, anthracenyloxy, phenanthrenyloxy, fluorenyl Oxy, indenyloxy and the like, and at least one hydrogen atom contained in the aryloxy group may be further substituted.

Specific examples of the silyl group which is a substituent used in the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl and methylcyclobutylsilyl , Dimethyl furyl silyl, and the like.

Specific examples of the alkenyl group used in the present invention include straight chain or branched chain alkenyl groups and include 3-pentenyl, 4-hexenyl, 5-heptenyl, 4-methyl- Dimethyl-pentenyl group, 6-methyl-5-heptenyl group and 2,6-dimethyl-5-heptenyl group.

In the present invention, the 'substituted' in the 'substituted or unsubstituted' may be a substituent selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, An alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, An alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, An arylsilyl group having 1 to 24 carbon atoms, an aryloxy group having 1 to 24 carbon atoms, germanium, phosphorus, and boron.

In addition, the carbon number range of the alkyl group or the aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms", "substituted or unsubstituted carbon group having 5 to 50 carbon atoms", and the like may be considered in the substituent-substituted portion. It means the total carbon number constituting the alkyl moiety or aryl moiety when viewed as unsubstituted without. For example, a phenyl group substituted with a butyl group in the para position means a aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

The aromatic compound represented by [Formula 1] according to the present invention may be selected from the compounds represented by the following [Formula 2] to [Formula 296].

[Formula 2] [Formula 3] [Formula 4] [Formula 5]

[Formula 6] [Formula 7] [Formula 8] [Formula 9]

[Formula 10] [Formula 11] [Formula 12] [Formula 13]

[Formula 14] [Formula 15] [Formula 16] [Formula 17]

[Formula 18] [Formula 19] [Formula 20] [Formula 21]

[Formula 22] [Formula 23] [Formula 24] [Formula 25]

[Formula 26] [Formula 27] [Formula 28] [Formula 29]

[Formula 30] [Formula 31] [Formula 32] [Formula 33]

[Formula 34] [Formula 35] [Formula 36] [Formula 37]

[Formula 38] [Formula 39] [Formula 40] [Formula 41]

[Formula 42] [Formula 43] [Formula 44] [Formula 45]

[Formula 43] [Formula 44] [Formula 45] [Formula 46]

[화학식 47] [화학식 48] [화학식 49] [화학식 50]

[Chemical Formula 48] [Chemical Formula 49] [Chemical Formula 50]

[Formula 51] [Formula 52] [Formula 53] [Formula 54]

[Formula 55] [Formula 56] [Formula 57] [Formula 58]

[Formula 55] [Formula 56] [Formula 57] [Formula 58]

[Formula 59] [Formula 60] [Formula 61] [Formula 62]

[Formula 63] [Formula 64] [Formula 65] [Formula 66]

[Formula 67] [Formula 68] [Formula 69] [Formula 70]

[Formula 71] [Formula 72] [Formula 73] [Formula 74]

[Formula 75] [Formula 76] [Formula 77] [Formula 78]

[Formula 79] [Formula 80] [Formula 81] [Formula 82]

[Formula 83] [Formula 84] [Formula 85] [Formula 86]

[Formula 87] [Formula 88] [Formula 89] [Formula 90]

[Formula 91] [Formula 92] [Formula 93] [Formula 94]

[Formula 95] [Formula 96] [Formula 97] [Formula 98]

[Formula 99] [Formula 100] [Formula 101] [Formula 102]

[Formula 103] [Formula 104] [Formula 105] [Formula 106]

[Formula 107] [Formula 108] [Formula 109] [Formula 110]

[Formula 111] [Formula 112] [Formula 113] [Formula 114]

[Formula 115] [Formula 116] [Formula 117] [Formula 118]

[화학식 119] [화학식 120] [화학식 121] [화학식 122]

[Chemical Formula 120]

[Formula 123] [Formula 124] [Formula 125] [Formula 126]

[Formula 127] [Formula 128] [Formula 129] [Formula 130]

[Formula 131] [Formula 132] [Formula 133] [Formula 134]

[Formula 135] [Formula 136] [Formula 137] [Formula 138]

[Formula 139] [Formula 140] [Formula 141] [Formula 142]

[Formula 143] [Formula 144] [Formula 145] [Formula 146]

[Formula 147] [Formula 148] [Formula 149] [Formula 150]

[Formula 151] [Formula 152] [Formula 153] [Formula 154]

[Formula 155] [Formula 156] [Formula 157] [Formula 158]

[Formula 159] [Formula 160] [Formula 161] [Formula 162]

[Formula 163] [Formula 164] [Formula 165] [Formula 166]

[Formula 167] [Formula 168] [Formula 169] [Formula 170]

[Formula 171] [Formula 172] [Formula 173] [Formula 174]

[화학식 175] [화학식 176] [화학식 177] [화학식 178]

[Formula 177] [Formula 177] [Formula 178]

[Formula 179] [Formula 180] [Formula 181] [Formula 182]

[Formula 183] [Formula 184] [Formula 185] [Formula 186]

[Formula 187] [Formula 188] [Formula 189] [Formula 190]

[Formula 191] [Formula 192] [Formula 193] [Formula 194]

[Formula 195] [Formula 196] [Formula 197] [Formula 198]

[Formula 199] [Formula 200] [Formula 201] [Formula 202]

[Formula 203] [Formula 204] [Formula 205] [Formula 206]

[Formula 207] [Formula 208] [Formula 209] [Formula 210]

[Formula 211] [Formula 212] [Formula 213] [Formula 214]

[Formula 215] [Formula 216] [Formula 217] [Formula 218]

[Formula 219] [Formula 220] [Formula 221] [Formula 222]

[Formula 223] [Formula 224] [Formula 225] [Formula 226]

[Formula 227] [Formula 228] [Formula 229] [Formula 230]

[Formula 231] [Formula 234] [Formula 235] [Formula 236]

[Formula 237] [Formula 238] [Formula 239] [Formula 240]

[Formula 241] [Formula 242] [Formula 243] [Formula 244]

[Formula 245] [Formula 246] [Formula 247] [Formula 248]

[Formula 249] [Formula 250] [Formula 251] [Formula 252]

[화학식 253] [화학식 254] [화학식 255] [화학식 256]

[Formula 253] [Formula 254] [Formula 255] [Formula 256]

[Formula 257] [Formula 258] [Formula 259] [Formula 260]

[Formula 261] [Formula 262] [Formula 263] [Formula 264]

[Formula 265] [Formula 266] [Formula 267] [Formula 268]

[Formula 269] [Formula 270] [Formula 271] [Formula 272]

[Formula 273] [Formula 274] [Formula 275] [Formula 276]

[Formula 277] [Formula 278] [Formula 279] [Formula 280]

[Formula 280] [Formula 281] [Formula 282] [Formula 283]

[화학식 284] [화학식 285] [화학식 286] [화학식 287]

[Formula 284] [Formula 285] [Formula 286] [Formula 287]

[화학식 288] [화학식 289] [화학식 290] [화학식 291]

[Formula 288] [Formula 289] [Formula 290] [Formula 291]

[Formula 292] [Formula 293] [Formula 294] [Formula 295] [Formula 296]

The present invention also includes a first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer is an aromatic represented by [Formula 1]. It may contain one or more compounds.

In addition, the organic layer including the aromatic compound of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function at the same time, a light emitting layer, an electron transport layer, and an electron injection layer. . In this case, the organic layer interposed between the first electrode and the second electrode may include a light emitting layer, the light emitting layer is composed of a host and a dopant, the aromatic compound of the present invention may be used as a host.

In the present invention, a dopant material may be used for the light emitting layer in addition to the host. When the light emitting layer includes a host and a dopant, the content of the dopant may be generally selected from about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host.

In addition, in the present invention, a known electron transport material can be used as the electron transport layer material, which functions to stably transport electrons injected from an electron injection electrode (cathode). Examples of known electron transporting materials include quinoline derivatives, especially tris (8-quinolinolate) aluminum (Alq3), TAZ, Balq, beryllium bis (benzoquinolin-10- olate: Bebq2), ADN, [Compound 201], [Compound 202], oxadiazole derivative PBD, BMD, BND and the like may be used.

TAZ BAlq

[Compound 201] [Compound 202] BCP

Further, the electron transporting layer used in the present invention can be used as the organometallic compound represented by the following formula (C) alone or in combination with the electron transporting layer material.

≪ RTI ID = 0.0 &

In [Formula C],

Y is a moiety selected from C, N, O and S, which is directly bonded to M to form a single bond, and any moiety selected from C, N, O and S is a moiety coordinating to M And is a ligand chelated by coordination bond with the single bond.

M is an alkali metal, an alkaline earth metal, an aluminum (Al), or a boron (B) atom.

OA is a monovalent ligand capable of single bond or coordination bond with M, O is oxygen, A is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, Substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C30 cycloalkyl, An alkenyl group, and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having a hetero atom O, N, or S.

In addition, when M is one metal selected from alkali metals, m = 1, n = 0, and when M is one metal selected from alkaline earth metals, m = 1, n = 1, or m = 2 and n = 0, and when M is boron or aluminum, any one of m = 1 to 3, and n satisfies m + n = 3 as any one of 0 to 2.

The 'substituted' in the 'substituted or unsubstituted' may be a substituent selected from the group consisting of deuterium, cyano, halogen, hydroxy, nitro, alkyl, alkoxy, alkylamino, arylamino, heteroarylamino, alkylsilyl, An aryl group, an aryl group, a heteroaryl group, germanium, phosphorus, and boron.

In addition, each Y is the same or different, and may be any one selected from the following [formula C1] to [formula C39] independently of each other.

[Structure C1] [Structure C2] [Structure C3]

[Structure C4] [Structure C5] [Structure C6]

[Structure C7] [Structure C8] [Structure C9] [Structure C10]

[Structural formula C11] [Structural formula C12] [Structural formula C13]

[Structural formula C14] [Structural formula C15] [Structural formula C16]

[Structure C17] [Structure C18] [Structure C19] [Structure C20]

[Structure C21] [Structure C22] [Structure C23]

[Structure C24] [Structure C25] [Structure C26]

[Structural formula C27] [Structural formula C28] [Structural formula C29] [Structural formula C30]

[Structure C31] [Structure C32] [Structure C33]

[Structure C34] [Structure C35] [Structure C36]

[Structure C37] [Structure C38] [Structure C39]

In the above Structural Formula C1 to Structural Formula C39,

R is the same or different and is each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C6-30 aryl, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms And may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring.

L represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted group having 5 to 30 carbon atoms A substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms, L is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, an aryl group having 3 to 20 carbon atoms, A heteroaryl group, a cyano group, a halogen group, deuterium, and hydrogen, and may be connected to an adjacent substituent by an alkylene or an alkenylene to form a spiro ring or a fused ring.

Hereinafter, the organic light emitting display device of the present invention will be described with reference to FIG. 1.

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

The organic electroluminescent device of the present invention and its manufacturing method will be described with reference to FIG.

First, the anode 20 is formed by coating an anode electrode material on the substrate 10. Here, as the substrate 10, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity are used.

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

The hole injection layer material is not particularly limited as long as it is conventionally used in the art. For example, 2-TNATA [4,4 ', 4 "-tris (2-naphthylphenyl-phenylamino) -triphenylamine] , NPD [N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'- biphenyl-4,4'-diamine], DNTPD [N, N'-diphenyl-N, N'-bis- [4- ] Can be used.

In addition, it is not particularly limited as long as it is commonly used in the art as a material of the hole transport layer, for example, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1 -Biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine (α-NPD) and the like can be used.

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

Wherein as material used for the hole blocking layer, BAlq, BCP, Bphen, TPBI, NTAZ, BeBq _2, OXD-7, Liq and [Formula 101] to [Chemical Formula 107] either, but one that can be used is selected from, this limited It is not.

BAlq BCP Bphen

TPBI NTAZ BeBq ₂

OXD-7 Liq

(101)

≪ RTI ID = 0.0 >

Formula 107

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

In addition, the light emitting layer may be formed of a host and a dopant. According to a specific example of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 kPa.

At this time, the dopant used in the light emitting layer may be at least one compound selected from the compounds represented by the following general formulas (A-1) to (J-1).

[Formula A-1]

In the above general formula A-1,

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

L ₁ , L ₂ and L ₃ may be the same or different from each other as ligands, independently of one another, selected from the following Structural Formula D, and "*" in the following Structural Formula D is coordinated to the metal ion M Represents a site.

[Formula D]

In [Formula D],

R is different from or the same as each other and is independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C6-50 aryl, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 carbon atoms, A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms And R is independently selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, Which may be further substituted with one or more substituents selected from a heteroaryl group having 3 to 20 carbon atoms, a cyano group, a halogen group, deuterium, and hydrogen, and R may be linked to each adjacent substituent by alkylene or alkenylene, Aromatic ring and a monocyclic or polycyclic aromatic ring.

L represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted group having 5 to 30 carbon atoms A substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms, L is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, an aryl group having 3 to 20 carbon atoms, A heteroaryl group, a cyano group, a halogen group, deuterium, and hydrogen, and may be connected to an adjacent substituent by an alkylene or an alkenylene to form a spiro ring or a fused ring.

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

[Formula B-1]

In [Formula B-1],

M ^A1 represents the same metal ion as defined in the above-mentioned [formula A-1], and Y ^A11 , Y ^A14 , Y ^A15 and Y ^A18 Each independently represent a carbon atom or a nitrogen atom, Y ^A12, Y ^A13, Y ^A16 and Y ^A17 each independently represents a substituted or unsubstituted carbon atoms, a substituted or unsubstituted nitrogen atom, an oxygen atom, a sulfur atom, the L ^A11 , L ^A12 , L ^A13 and L ^A14 each represent a linking group such as L ₁ , L ₂ and L ₃ defined in the above [formula A-1], and Q ^A11 and Q ^A12 represent an atom bonding to M ^A1 . ≪ / RTI >

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

[Formula C-1]

In [Formula C-1],

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

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

[Formula D-1]

In [Formula D-1],

M ^C1 represents a metal ion as defined in the above-mentioned [formula A-1], R ^C11 and R ^C12 each independently represent a hydrogen atom, a substituent which is mutually connected to form a 5-membered ring, , R ^C11 and R ^C12 each independently represent a hydrogen atom, a substituent which is mutually connected to form a 5-membered ring or a substituent which is not connected to each other, R ^C13 and R ^C14 each independently represent a hydrogen atom, G ^C11 and G ^C12 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom, L ^C11 and L ^C12 represent a linking group, Q ^C11 and Q ^C12 Represents a partial structure containing an atom bonding to M ^C1 .

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

[Formula E-1]

In [Formula E-1],

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

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

[Formula F-1]

In [Formula F-1],

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

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

[General Formula G-1]

In [General Formula G-1],

M ^F1 is above represents the same metal ion as defined from the following formula ^{A-1], L F11,} L F12 and L ^F13 represents a linking group, R ^F11, R ^F12, R ^F13 and R ^F14 represents a substituent, R ^F11 and R ^F12 , R ^F12 And R ^F13 , R ^F13 and R ^F14 may be connected to each other to form a ring, wherein the ring formed by R ^F1 and R ^F12 , R ^F13 and R ^F14 is a 5-membered ring. In addition, Q ^F11 and Q ^F12 represent a partial structure containing an atom bonded to M ^F1 .

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

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

In the above general formula H-1,

R ¹¹ and R ¹² are an alkyl group, an aryl group, or a heteroaryl group, which may form a fused ring with adjacent substituents, and q 11 and q 12 are integers of 0 to 4, preferably 0 to 2. When q11 and q12 are 2 to 4, a plurality of R11 and R12 may be the same or different.

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

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

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

In [Formula H-2],

R ²¹ , R ²² , n ² , m ² , q ²² and L ² are the same as R ¹¹ , R ¹² , n ¹ , m ¹ , q ¹² and L ¹ , respectively, and q ²¹ is an integer of 0 to 2; , 0 is preferred.

In [Formula H-3],

^{R 31, n 3, m 3} , L 3 are each as defined in the ^{R 11, n 1, m 1} , L 1 and, q ³¹ represents an integer of 0-8, and 0-2 are preferred, greater than 0, desirable.

According to one embodiment of the present invention, the compounds represented by the above-mentioned [formula H-1] to [formula H-3] may be any one selected from the following compounds.

[Formula I-1]

In [Formula I-1],

Ring A, ring B, ring C, and ring D represent a nitrogen-containing heterocyclic ring which may have a substituent, and the remaining two rings are an aryl ring or heteroaryl which may have a substituent A condensed ring can be formed by ring A and ring B, ring A and ring C and / or ring B and ring D, respectively.

X ¹ , X ² , X ³ and X ⁴ represent a nitrogen atom in which any two of them are coordinated to a platinum atom, and the other two represent a carbon atom or a nitrogen atom.

Q ¹ , Q ² and Q ³ each independently represent a divalent atom (bond) or a bond, but Q ¹ , Q ² and Q ³ do not simultaneously represent a bond. ^{Two of} Z ¹ , Z ² , Z ³ and Z ⁴ represent coordinate bond, and the remaining two represent a covalent bond, an oxygen atom or a sulfur atom.

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

[Formula J-1]

In [formula J-1],

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

In Ar1, C represents a carbon atom constituting the ring structure represented by Ar1. In addition, said R1 and R2 may mutually be same or different, and represent a substituted or unsubstituted alkyl group or an aryl group, respectively, and L represents a monodentate ligand.

M is preferably Pt, and Ar1 is preferably selected from a 5-membered ring, a 6-membered ring and condensed ring thereof.

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

In addition to the dopant and the host, the emission layer may further include various hosts and various dopant materials.

In addition, one or more layers selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer may be formed by a single molecule deposition method or a solution process, wherein the deposition method Means a method of forming a thin film by evaporating a material used as a material for forming each layer through heating or the like in a vacuum or low pressure state, and the solution process is used as a material for forming each layer. It refers to a method of forming a thin film through a method such as mixing the material with a solvent and inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating and the like.

Further, the organic light emitting display device according to the present invention can be used in a device selected from a flat panel display device, a flexible display device, a flat or white flat illumination device and a single or white flexible illumination device.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be apparent, however, to those skilled in the art that these embodiments are for further explanation of the present invention and that the scope of the present invention is not limited thereby.

Synthetic example  1. Synthesis of Formula 2

Synthetic example  1-1. Synthesis of <1-a>

<1-a> was synthesized according to Reaction Scheme 1 below.

[Reaction Scheme 1]

<1-a>

5000 mL round bottom flask under nitrogen you methyl anthranilate state rate 87 g (0.576 mol), 1- bromo-4-iodo-benzene 135.1 g (0.478 mol), palladium acetate _{(Pd (OAc) 2) 1.3} g (0.006 10 g (0.017 mol) of zincphosphate, 217.5 g (0.668 mol) of cesium carbonate and 2500 mL of toluene were charged and refluxed for 6 hours. When the reaction was completed, the reaction product was separated into layers and the aqueous layer was removed. The organic layer was separated, concentrated under reduced pressure, and <110 g (75%) was obtained through column chromatography.

Synthetic example  1-2. Synthesis of <1-b>

<1-b> was synthesized by the following Scheme 2.

[Reaction Scheme 2]

<1-b>

110 g (0.359 mol) of the compound represented by Chemical Formula 1-a obtained from Scheme 1 and 1650 mL of diisopropyl ether were added to a 5000 mL round bottom flask under nitrogen, and 419 mL of methylmagnesium bromide was slowly added dropwise thereto. After dropping, the mixture was stirred at 50 degrees. When the reaction was completed, the resulting product was separated into layers to remove the aqueous layer, and the organic layer was separated and concentrated under reduced pressure to obtain 108 g (98.2%) of <1-b> through column chromatography.

Synthetic example  1-3. Synthesis of <1-c>

&Lt; 1-c > was synthesized by the following Reaction Scheme 3.

Scheme 3

<1-c>

108 g (0.36 mol) of the compound represented by Chemical Formula 1-b obtained from Scheme 2 and 400 mL of phosphoric acid were added to a 1000 mL round bottom flask, followed by stirring at room temperature. When the reaction was completed, water was added to the resultant of the reaction and stirred. After stirring, the mixture was filtered and washed with water and methanol. Column chromatography gave 75g (75%) of <1-c>.

Synthetic example  1-4. Synthesis of <1-d>

<1-d> was synthesized according to Scheme 4 below.

[Reaction Scheme 4]

<1-d>

In a 2000 mL round bottom flask, 100 g (0.598 mol) of carbazole was added to 250 mL of N, N-diethylamide under nitrogen, and the reaction mixture was cooled to 0 degrees. 106.44 g (0.598 mol) of N-bromosuccinimide was dissolved in 530 mL of N, N-dimethylamide and added dropwise. After the dropwise addition, the mixture was stirred at room temperature. When the reaction was completed, the resultant of the reaction was poured into water, stirred, filtered and washed with water and methanol to give 76.4 g (51.9%) of <1-d>.

Synthetic example  1-5. Synthesis of <1-e>

<1-e> was synthesized by the following Reaction Scheme 5.

[Reaction Scheme 5]

<1-e>

In a 2000 mL round-bottom flask, 76.4 g (0.31 mol) of compound represented by Chemical Formula 1-d obtained from Scheme 4 under nitrogen, 111.8 g (0.466 mol) of iodobenzene, 86 g (0.62 mol) of potassium carbonate, and 4.32 g of copper chloride ( 0.02 mol) and 650 mL of dimethyl sulfoxide were added and refluxed for 12 hours. When the reaction was completed, the reaction product was separated by layer, the aqueous layer was removed, the organic layer was separated and concentrated under reduced pressure, and then column chromatography was performed. -e> 76 g (76%) was obtained.

Synthetic example  1-6. Synthesis of <1-f>

<1-f> was synthesized by the following Reaction Scheme 6.

[Reaction Scheme 6]

<1-f>

In a 1000 mL round bottom flask, 73 g (0.26 mol) of compound represented by the formula (I-e) obtained from Scheme 5, 61 g (0.272 mol) of bispinolacholate diborone, [1,1'-bis (diphenylphosphino) ferrocene] die 4.89 g (0.007 mol) of chloropalladium (2), 45.42 g (0.68 mol) of potassium acetate, and 520 mL of toluene were added, and the mixture was refluxed for 12 hours. After the reaction was completed, the resultant of the reaction was extracted and the organic layer was concentrated under reduced pressure, and then <1-f> 68g (81%) was obtained through column chromatography.

Synthetic example  1-7. Synthesis of <1-g>

<1-g> was synthesized according to the following Reaction Scheme 7.

[Reaction Scheme 7]

<1-g>

In a 250 mL round bottom flask, 10 g (0.035 mol) of the compound represented by Formula 1-c obtained from Scheme 3 and 16.7 g (0.045 mol) tetrakis (triphenylphosphine) palladium represented by formula 1-f obtained by Scheme 6 (0) 1.2 g (0.001 mol), potassium carbonate 12.1 g (0.09 mol), toluene 50 mL, tetrahydrofuran 50 mL and 20 mL of water were added, and the mixture was refluxed for 12 hours. When the reaction was completed, the resultant of the reaction was separated into layers to remove the aqueous layer, the organic layer was separated and concentrated under reduced pressure to give <1-g> 14.6g (93%) through column chromatography.

Synthetic example  1-8. Synthesis of <1-h>

<1-h> was synthesized by the following Reaction Scheme 8.

[Reaction Scheme 8]

<1-h>

In a 2000 mL round bottom flask, 39.5 g (1.7 mol) of magnesium, 10 g of iodine and 100 mL of tetrahydrofuran were added under reflux under nitrogen to reflux for 2 hours. After cooling to room temperature, 212.8 g (1.4 mol) of bromobenzene was dissolved in 200 mL of tetrahydrofuran and slowly added dropwise. The mixture was refluxed for 2 hours and cooled to room temperature. In another 2 L round bottom flask, 100 g (0.54 mol) of cyanuric chloride was dissolved in 200 mL of tetrahydrofuran, and the reaction solution was cooled to 0 degrees. The reaction solution was slowly added dropwise while maintaining the temperature at 0 degrees. After completion of the reaction, the reaction was terminated with 4 mole hydrochloric acid aqueous solution, extracted, and the organic layer was concentrated under reduced pressure and recrystallized with hexane to obtain <1-h> 100g (68.9%).

Synthetic example  1-9. Synthesis of <2>

<2> was synthesized by the following Scheme 9.

[Reaction Scheme 9]

&Lt; 2 &

In a 100 mL round bottom flask, 2 g of sodium hydride was dissolved in 200 mL of N, N-diethylamide under nitrogen, and cooled to 0 ° C. 14.6 g (0.0324 mol) of the compound represented by Chemical Formula 1-g obtained in Scheme 7 at 0 degrees was dissolved in 200 mL of N, N-diethylamide and slowly added dropwise thereto. After dropping, the mixture was stirred for 1 hour. 13 g (0.05 mol) of the compound represented by Chemical Formula 1-h obtained at 0 ° C was dissolved in 200 mL of N, N-diethylamide and slowly added dropwise thereto. After the dropwise addition, the mixture was stirred at room temperature. When the reaction was completed, the resultant of the reaction was poured into water, stirred, filtered and washed with water and methanol to give 3.6g (20%).

MS (MALDI-TOF): m / z 681.29 [M] ⁺

¹³ C NMR (75 MHz, CDCl 3) δ:

22.6 30.9 109.5 110 111.6 111.7 112.2 116.8 118.7 119.4 119.8 120.1 121.4 125.4 125.5 126.3 126.6 127.5 129 129.2 129.3 130.5 130.9 131.1 131.4 131.7 134 134.7 136 136.8 137.1 143.7 144.3 172.2 178.2 [48C]

Synthetic example  2. Synthesis of Chemical Formula 27

Synthetic example  2-1. Synthesis of <2-a>

&Lt; 2-a > was synthesized by the following Reaction Scheme 10.

[Reaction Scheme 10]

<2-a>

Synthesis was performed in the same manner as the compound synthesis method represented by Chemical Formula 1-g, to obtain 12.8 g (78.5%) of <2-a>.

Synthetic example  2-2. Synthesis of <27>

<27> was synthesized according to Scheme 11 below.

[Reaction Scheme 11]

<27>

7.4 g (34%) was obtained by the same method as the synthesis method of the compound represented by Formula 2.

MS (MALDI-TOF): m / z 566.25 [M] ⁺

¹³ C NMR (75 MHz, CDCl 3) δ:

22.6 30.9 111.7 112.2 118.7 120.1 125.1 125.4 126.3 127.2 127.5 128.3 129 129.2 130.5 130.9 131.1 132.1 133.1 134.2 134.7 136 136.7 137.1 172.2 178.2 [40C]

Synthetic example  3. Synthesis of Chemical Formula 45

Synthetic example  3-1. Synthesis of <3-a>

&Lt; 3-a > was synthesized by the following Reaction Scheme 12.

[Reaction Scheme 12]

<3-a>

In a 500 mL round bottom flask, 20 g (0.06 mol) of compound represented by 1-c obtained from Scheme 3, 18.36 g (0.09 mol) of iodobenzene, 14.4 g (0.104 mol) of potassium carbonate, and 6.9 g (0.03 mol) of copper chloride 160 mL of dimethyl sulfoxide was added and refluxed for 6 hours. When the reaction was completed, the resultant of the reaction was extracted and the organic layer was separated and concentrated under reduced pressure, and then obtained 15.5 g (60%) through column chromatography.

Synthetic example  3-2. Synthesis of <3-b>

<3-b> was synthesized according to the following Reaction Scheme 13.

[Reaction Scheme 13]

<3-b>

17-g (73%) of <2-b> was obtained by the same method as the synthesis method of the compound represented by Chemical Formula 1-f.

Synthetic example  3-3. Synthesis of <3-c>

<3-c> was synthesized by the following Reaction Scheme 14.

[Reaction Scheme 14]

<3-c>

It was synthesized in the same manner as the compound synthesis method represented by the formula 1-g to obtain <2-c> 8.5g (40%).

Synthetic example  3-4. Synthesis of <3-d>

<3-d> was synthesized by the following Reaction Scheme 15.

[Reaction Scheme 15]

<3-d>

53 g (73%) of <3-d> was obtained by the same method as the compound synthesis method of Chemical Formula 1-h.

Synthetic example  3-5. Synthesis of <45>

<45> was synthesized according to Scheme 16 below.

[Reaction Scheme 16]

<45>

Synthesis was carried out in the same manner as in the synthesis of the compound represented by Formula 2 to obtain 8.2g (65.7%).

MS (MALDI-TOF): m / z 722.34 [M] ⁺

¹³ C NMR (75 MHz, CDCl 3) δ:

22.6 30.9 102.4 111.7 112.2 115.3 115.8 118.7 120.1 123.6 123.7 125.4 125.7 126.3 126.8 127.5 128.7 129 129.2 129.6 130.5 130.9 131.1 131.7 132.6 134.4 134.7 135.5 135.8 136 136.6 137.1 145.9 163.5 165.2 169.1 [52C]

Synthetic example  4. Synthesis of Chemical Formula 79

Synthetic example  4-1. Synthesis of <4-a>

<4-a> was synthesized according to Scheme 17 below.

[Reaction Scheme 17]

In a 2000 mL round bottom flask, add 100 g (0.543 mol) of diphenylthiophene and 800 mL of tetrahydrofuran under nitrogen, stir for 30 minutes under nitrogen, and cool the reaction to -78 degrees. 407 mL (0.65 mol) of 1.6 mol normal butyllithium was slowly added dropwise. After stirring for 24 hours at room temperature the reaction is cooled to -78 degrees. 84.76 mL (0.76 mol) of trimethylborate was slowly added dropwise. The temperature was raised to room temperature and stirred for 2 hours. When the reaction was completed, the reaction was terminated with 2 molar hydrochloric acid aqueous solution, extracted, and the organic layer was concentrated under reduced pressure and recrystallized with hexane to give 96.4 g (78%).

Synthetic example  4-2. Synthesis of <4-b>

<4-b> was synthesized according to Scheme 18 below.

[Reaction Scheme 18]

<4-b>

49.3 g (65.5%) of <4-b> was obtained by the same method as the synthesis method of the compound represented by Chemical Formula 1-h.

Synthetic example  4-3. Synthesis of <4-c>

<4-c> was synthesized according to Scheme 19 below.

Scheme 19

<4-c>

Synthesis was carried out in the same manner as in the synthesis of the compound represented by Formula 1-g to obtain <4-c> 10g (73.6%).

Synthetic example  4-4. Synthesis of <79>

It was synthesized according to Reaction Scheme 20 below.

[Reaction Scheme 20]

<79>

7.8 g (35.5%) was obtained by the same method as the synthesis method of the compound represented by Formula 2.

MS (MALDI-TOF): m / z 632.28 [M] ⁺

¹³ C NMR (75 MHz, CDCl 3) δ:

22.6 30.9 111.7 112.2 118.7 120.1 122.1 122.7 122.8 123.2 124.3 124.4 124.8 125.4 125.6 126.1 126.3 126.5 127 127.5 129 130.5 130.9 134.4 135.5 136 137.1 139.9 172.2 178.2 [42C]

Synthetic example  5. Synthesis of Formula 107

Synthetic example  5-1. Synthesis of <5-a>

<5-a> was synthesized according to Scheme 21 below.

[Reaction Scheme 21]

<5-a>

Synthesis was carried out in the same manner as in the synthesis of the compound represented by Formula 1-h to give <5-a> 47.6g (76%).

Synthetic example  5-2. Synthesis of <5-b>

<5-b> was synthesized according to Scheme 22 below.

[Reaction Scheme 22]

<5-b>

Compound <5-b> 38.4 g (51.5%) was obtained by the same method as the synthesis method of the compound represented by Formula 2.

Synthetic example  5-3. Synthesis of <5-c>

<5-c> was synthesized according to Scheme 23 below.

[Reaction Scheme 23]

<5-c>

Synthesis was carried out in the same manner as in the synthesis of the compound represented by Formula 2 to obtain <5-c> 15.4 g (72.3%).

Synthetic example  5-4. Synthesis of <107>

It was synthesized according to Scheme 24 below.

Scheme 24

<107>

In a 1 L round bottom flask, 15.4 g (0.024 mol) of compound represented by the formula (5-c) obtained from Scheme 23, 6.2 g (0.037 mol) of diphenylamine, and 0.22 g (0.24) of tris (dibenzideneacetone) dipalladium (0) mmol), 18-crown-6-ether 0.2g (0.001mol), tributylbutylphosphine 0.3g (0.01mol), potassium carbonate 6.8g (0.05mol) and 400 mL of zylene were added and refluxed for 12 hours. After the completion of the reaction, the mixture was extracted and the organic layer was concentrated under reduced pressure and recrystallized with hexane to obtain 7.4 g (42%).

MS (MALDI-TOF): m / z 701.33 [M] ⁺

¹³ C NMR (75 MHz, CDCl 3) δ:

22.3 30.9 109.5 111.7 112.6 118.7 119.8 120.3 120.5 121.4 122.5 125.4 125.6 125.7 126.6 126.8 127 127.5 129 129.6 130.5 130.9 131.5 132.4 134.4 137.1 138.7 145.9 173.2 177.7 179.6 [48C]

Synthetic example  6. Synthesis of Chemical Formula 138

Synthetic example  6-1. Synthesis of <6-a>

<6-a> was synthesized according to Scheme 25 below.

[Reaction Scheme 25]

<6-a>

Synthesis was carried out in the same manner as in the synthesis of the compound represented by Formula 1-h to give <6-a> 37.9 g (61.8%).

Synthetic example  6-2. Synthesis of <6-b>

<6-b> was synthesized by the following Scheme 26.

[Reaction Scheme 26]

<6-b>

43.2 g (72.2%) of <6-b> was obtained by the same method as the synthesis method of the compound represented by Formula 2.

Synthetic example  6-3. Synthesis of <6-c>

<6-c> was synthesized by the following Scheme 27.

[Reaction Scheme 27]

<6-c>

Synthesis was carried out in the same manner as in the synthesis of the compound represented by Formula 1-g to obtain <6-c> 15g (84.9%).

Synthetic example  6-4. Synthesis of <138>

It was synthesized by Reaction Scheme 28 below.

[Reaction Scheme 28]

<138>

Synthesis was carried out in the same manner as in the synthesis of the compound represented by Formula 2 to obtain 9.8 g (yield 36%).

MS (MALDI-TOF): m / z 708.26 [M] ⁺

¹³ C NMR (75 MHz, CDCl 3) δ:

22.6 30.9 95.6 109.5 113.5 115.3 115.8 117.8 119.7 119.8 121.4 121.6 122.7 122.8 123.2 123.6 123.7 124.3 124.4 125.4 126.3 126.4 126.6 127.6 127.9 129.2 129.8 130.5 130.9 132.6 134.4 135.5 136.6 138 138.8 139.7 140.8 141.6 142 142.4 143.3 [51C]

Synthetic example  7. Synthesis of Formula 239

Synthetic example  7-1. Synthesis of <7-a>

<7-a> was synthesized by the following Reaction Scheme 29.

[Reaction Scheme 29]

<7-a>

40g (98%) of <7-a> was obtained by the same method as the synthesis method of the compound represented by Chemical Formula 1-f.

Synthetic example  7-2. Synthesis of <7-b>

<7-b> was synthesized according to Scheme 30 below.

[Reaction Scheme 30]

<7-b>

37g (94%) of <7-b> was obtained by the same method as the synthesis method of the compound represented by Chemical Formula 1-g.

Synthetic example  7-3. Synthesis of <7-c>

<7-c> was synthesized by the following Scheme 31.

[Reaction Scheme 31]

<7-c>

In a 1 L round bottom flask, 250 mL of N, N-dimethylamide was added to 20 g (0.045 mol) of the compound represented by 7-b obtained in Scheme 30, stirred for 30 minutes under nitrogen, and the reaction was cooled to 0 degrees. 18.5 g (0.068 mol) of N-bromosuccinimide was dissolved in 170 mL of N, N-dimethylamide and added dropwise. After the dropwise addition, the mixture was stirred at room temperature. When the reaction was completed, the resulting product was poured into water, stirred, filtered, washed with water and methanol to obtain 18.46 g (78%) of the compound represented by the formula (7-c).

Synthetic example  7-4. Synthesis of <7-d>

<7-d> was synthesized according to Scheme 32 below.

[Reaction Scheme 32]

<7-d>

14.7 g (81%) of <7-d> was obtained by the same method as the synthesis method of the compound represented by Chemical Formula 1-g.

Synthetic example  7-5. Synthesis of <239>

It was synthesized by the following Reaction Scheme 33.

[Reaction Scheme 33]

<239>

7.9 g (39.2%) was obtained by the same method as the synthesis method of the compound represented by Formula 2.

MS (MALDI-TOF): m / z 856.27 [M] ⁺

¹³ C NMR (75 MHz, CDCl 3) δ:

21.3 50.7 119.4 120.1 122.8 123.2 123.7 124.3 124.4 125.9 127.5 128.1 129.2 129.5 130.5 131.1 132.9 134.7 135.9 137.1 139.6 140.7 143.4 144.7 172.2 178.2 [58C]

Synthetic example  8. Synthesis of Chemical Formula 240

Synthetic example  8-1. Synthesis of <8-a>

<8-a> was synthesized according to Scheme 34 below.

[Reaction Scheme 34]

<8-a>

10.7 g (75%) of <8-a> was obtained by the same method as the synthesis method of the compound represented by Chemical Formula 1-g.

Synthetic example  8-2. Synthesis of <240>

<240> was synthesized according to Scheme 35 below.

[Reaction Scheme 35]

<240>

Synthesis was carried out in the same manner as the synthesis method of the compound represented by Formula 2, to obtain 6.3 g (40%).

MS (MALDI-TOF): m / z 724.28 [M] ⁺

¹³ C NMR (75 MHz, CDCl 3) δ:

21.3 49.5 107.1 112 120.1 120.3 123.3 127.5 128.1 129.2 129.5 130.5 131.1 132.9 134.7 135.9 137.1 142.9 144.7 154 172.2 178.2 [50C]

Synthetic example  9. Synthesis of Chemical Formula 272

Synthetic example  9-1. Synthesis of <9-a>

<9-a> was synthesized according to Scheme 36 below.

[Reaction Scheme 36]

<9-a>

99.1g (78.6%) of <9-a> was obtained by the same method as the synthesis method of the compound represented by Chemical Formula 4-a.

Synthetic example  9-2. Synthesis of <9-b>

<9-b> was synthesized according to Scheme 37 below.

[Reaction Scheme 37]

<9-b>

20g (52%) of <9-a> was obtained by the same method as the synthesis method of the compound represented by Chemical Formula 7-c.

Synthetic example  9-3. Synthesis of <9-c>

<9-c> was synthesized by the following Scheme 38.

[Reaction Scheme 38]

<9-c>

20.5 g (69.5%) of <9-c> was obtained by the same method as the synthesis method of the compound represented by Chemical Formula 1-g.

Synthetic example  9-4. Synthesis of <272>

It was synthesized by the following Reaction Scheme 39.

[Reaction Scheme 39]

<272>

Synthesis was carried out in the same manner as in the synthesis of the compound represented by Formula 2 to obtain 10.4 g (35.6% yield).

MS (MALDI-TOF): m / z 772.28 [M] ⁺

¹³ C NMR (75 MHz, CDCl 3) δ:

22.9 30.9 111.5 112.2 117.1 119.8 120.1 120.9 122.8 123.3 123.5 123.8 124.7 126.3 126.5 127.5 129.2 130.9 131 131.1 134.7 136 145.9 151.2 172.2 178.2 [54C]

Synthetic example  10. Synthesis of Chemical Formula 282

Synthetic example  10-1. Synthesis of <10-a>

&Lt; 10-a > was synthesized by the following Reaction Formula 40.

[Reaction Scheme 40]

<10-a>

200 g (0.73 mol) of 2-bromo-9,9'-dimethylfluorene and 2400 mL of tetrahydrofuran were added to a 5 L round bottom flask, and the mixture was stirred under nitrogen for 30 minutes and cooled to -78 degrees. 549 mL (0.88 mol) of 1.6 mol normal butyllithium was slowly added dropwise. After stirring for 24 hours at room temperature the reaction is cooled to -78 degrees. Slowly add 223 g (0.88 mol) of iodine. The temperature was raised to room temperature and stirred for 12 hours. After completion of the reaction, the reaction was terminated with an aqueous solution of sodium thiosulfate and extracted. The organic layer was concentrated under reduced pressure, and then separated by column chromatography using hexane, thereby obtaining 209 g (89%).

Synthetic example  10-2. Synthesis of <10-b>

<10-b> was synthesized by the following Reaction Scheme 41.

[Reaction Scheme 41]

<10-b>

In a 5 L round bottom flask, 209 g (0.63 mol) of the compound represented by 5-a from chemical formula 9, 122.1 g (0.789 mol) of 2-bromoaniline, 12 g of tris (dibenzideneacetone) dipalladium (0) 0.013 mol), 1,1'-bis (diphenylphosphino) ferrocene 14.5g (0.026mol), sodium tert-butoxide 94.1g (0.979mol) and toluene 2100mL were added and refluxed for 12 hours. After completion of the reaction, the mixture was filtered and concentrated under reduced pressure, and then separated by column chromatography using hexane to obtain <10-b> 164g (69%).

Synthetic example  10-3. Synthesis of <10-c>

<10-c> was synthesized by the following Scheme 42.

[Reaction Scheme 42]

<10-c>

In a 2 L round bottom flask, 70 g (0.19 mol) of compound represented by the formula (5-b) obtained from Scheme 9, 1.4 g (0.004 mol) of tricyclohexylphosphinium tetrafluoroborate, 0.431 g (0.002 mol) of palladium acetate, potassium carbonate 53.1 g (0.384 mol) and 700 mL of N, N-dimethylacetamide were added thereto, and the mixture was refluxed for 12 hours. After the completion of the reaction and extraction, the organic layer was concentrated under reduced pressure, recrystallized with hexane and dried to give 46.3g (85%) of <10-c>.

Synthetic example  10-4. Synthesis of <10-d>

<10-d> was synthesized according to Scheme 43 below.

[Reaction Scheme 43]

<10-d>

Synthesis was carried out in the same manner as in the synthesis of the compound represented by Formula 2 to obtain <10-d> 16g (yield 87%).

Synthetic example  10-5. Synthesis of <282>

It was synthesized according to Scheme 44 below.

[Reaction Scheme 44]

<282>

7.8 g (40%) was obtained by the same method as the synthesis method of the compound represented by Formula 107.

MS (MALDI-TOF): m / z 873.38 [M] ⁺

¹³ C NMR (75 MHz, CDCl 3) δ:

21.3 30.9 45.5 50.1 105.4 109.5 110.9 114.4 116 118.7 119.8 119.9 120.2 121.4 121.6 123.2 126.6 126.7 127.5 128.1 129 129.1 129.2 129.5 129.6 129.7 130.5 131.1 131.9 132.4 133 133.9 134 134.7 135.5 135.9 137.1 141 144.7 145.4 147.8 172.2 178

Synthetic example  11.Synthesis of Formula 292

Synthetic example  11-1. Synthesis of <11-a>

<11-a> was synthesized by the following Scheme 45.

[Reaction Scheme 45]

<11-a>

At room temperature, 2-aminobenzonitrile (20.0 g, 169 mmol) and 140 mL of tetrahydrofuran were added to a round bottom flask under a nitrogen stream and stirred. 112.9 mL (339 mmol) of phenylmagnesium bromide (3.0 M in Et ₂ O) was added dropwise. After reflux stirring for about 1 hour, the temperature was set to 0 캜. Ethyl chloroformate (22.0 g, 203 mmol) was added dropwise thereto, followed by reflux stirring for about 1 hour. An aqueous ammonium chloride solution was added until weakly acidic, and the resulting solid was filtered and washed with water and heptane to give 30.1 g of <11-a>. (Yield 80%)

Synthetic example  11-2. Synthesis of <11-b>

<11-b> was synthesized by the following Scheme 46.

[Reaction Scheme 46]

<11-b>

At room temperature, about 80 mL of the above-described [intermediate 11-a] (30.0 g, 135 mmol) and phosphorus oxychloride were added to a round bottom flask under a nitrogen stream, followed by stirring. After refluxing overnight, the temperature was cooled to −20 ° C. the next day and water was slowly added dropwise to about 400 mL. The resulting solid was filtered and washed with water, methanol and heptane. Recrystallization with toluene and heptane yielded 14.6 g of <11-b>. (Yield: 44.9%).

Synthetic example  11-3. Synthesis of <292>

<292> was synthesized according to Scheme 47 below.

[Reaction Scheme 47]

<292>

4.9 g (35%) of <292> was obtained in the same manner using the synthesized <11-b> instead of the <1-h> used in [Scheme 9].

MS (MALDI-TOF): m / z 654.28 [M] ⁺

¹³ C NMR (75 MHz, CDCl 3) δ:

22.6 30.9 109.5 110 111.6 111.7 112.2 116.8 118.5 118.7 119.4 119.8 120.1 121.4 122.9 125 125.4 125.5 125.8 126.3 126.6 127.5 128.7 129 129.2 129.3 130.5 130.9 131.4 131.7 131.8 134 136 136.8 137.1 143.7 144.3 149.2 155.6 160 [47C]

Synthetic example  12. Synthesis of Chemical Formula 293

Synthetic example  12-1. Synthesis of <12-a>

<12-a> was synthesized according to Scheme 48 below.

[Reaction Scheme 48]

<12-a>

Under nitrogen stream, 1-nitronaphthalene (50.0g, 289mmol), ethyl cyanoacetate (98.0g, 866mmol), potassium cyanide (20.7g, 318mmol), potassium hydroxide (32.4g, 577mmol) in a round bottom flask immersed in water Was added and stirred. 100 mL of dimethylformamide was added and the temperature was raised to 60 ° C., followed by stirring overnight. The next day, the change in TLC was checked and the temperature of the flask was brought to room temperature. The reaction solution was concentrated under reduced pressure to remove all possible dimethylformamide. The concentrate was transferred to the reactor with a small amount of dichloromethane, 500 mL of 5% aqueous sodium hydroxide solution was added thereto, followed by stirring. After reflux stirring for about 1 hour, the temperature was brought to room temperature. Extracted with ethyl acetate and water. The residue was subjected to column chromatography using ethyl acetate and heptane. Recrystallization with toluene and heptane yielded 24.6 g (yield 50.7%) of <12-a> as a white solid.

Synthetic example  12-2. Synthesis of <12-b>

<12-b> was synthesized according to Scheme 49 below.

[Reaction Scheme 49]

<12-b>

Instead of 2-aminobenzonitrile used in [Scheme 45], the synthesized compound was synthesized in the same manner as in [Scheme 45] to [Scheme 46], using 21 <a-a> synthesized above to obtain 21 g of <12-b>. (Yield 74.5%)

Synthetic example  12-3. Synthesis of <293>

<293> was synthesized according to Scheme 50 below.

[Reaction Scheme 50]

<293>

Instead of <1-h> used in [Scheme 9], 5.8 g (46%) of [Formula 293] was obtained by the same method as described in <12-b>.

MS (MALDI-TOF): m / z 704.29 [M] ⁺

¹³ C NMR (75 MHz, CDCl 3) δ:

22.6 30.9 109.5 110 111.6 111.7 112.2 116.8 118.5 118.7 119.4 119.8 120.1 121.4 123.1 124.9 125.4 125.5 125.8 126.3 126.6 127.2 127.3 127.5 128.7 129 129.2 129.3 129.5 130.5 130.9 131.4 131.7 131.8 133.5 134 136 136.8 137.1 143.7 144.3 149.9 155.6 160

Synthetic example  13. Synthesis of Chemical Formula 295

Synthetic example  13-1. Synthesis of <13-a>

<13-a> was synthesized according to Scheme 51 below.

[Reaction Scheme 51]

<13-a>

Instead of <12-a> used in [Scheme 49], 3-amino-2-naphtonitrile was synthesized in the same manner to obtain 20 g of <13-a>. (Yield 71%)

Synthetic example  13-2. Synthesis of <295>

<295> was synthesized according to Scheme 52 below.

[Reaction Scheme 52]

<295>

Instead of <1-h> used in [Scheme 9], 5.2 g (41%) of [Formula 295] was obtained by the same method as described in <13-a>.

MS (MALDI-TOF): m / z 704.29 [M] ⁺

¹³ C NMR (75 MHz, CDCl 3) δ:

22.6 30.9 109.5 110 111.6 111.7 112.2 116.8 118.5 118.7 119.4 119.8 120.1 121.4 123.4 125.1 125.4 125.5 126.3 126.6 127.2 127.3 127.5 128.7 129 129.2 129.3 130.5 130.9 131.4 131.7 131.8 132 133.5 134 136 136.8 137.1 143.7 144.3 149.2 155.6 160 [51C]

Example  1 to 10: Preparation of Organic Light Emitting Diode

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After mounting the substrate in the vacuum chamber, the base pressure is 1 × 10 ^-6 torr and the organic material is placed on the ITO DNTPD (700 kPa), NPD (300 kPa), the compound prepared in Synthesis Examples 1 to 10 + Ir (ppy ) ₃ (10%) (300 Å), Alq ₃ (350 Å), LiF (5 Å), Al (1,000 Å) in the order of the film formation, and was measured at 0.4 mA.

[DNTPD] [NPD]

[Ir (ppy) ₃ ] [Alq ₃ ]

Comparative Example  One

The organic light emitting diode device for Comparative Example 1 was manufactured in the same manner except for using CBP, which is generally used as a phosphorescent host material, instead of the compound prepared by the invention in the device structures of Examples 1 to 10. The structure is shown below.

<CBP>

For organic light emitting diodes manufactured according to Examples 1 to 10 and Comparative Example 1, voltage, current density, luminance, color coordinates, and lifetime were measured, and the results are shown in the following [Table 1]. T80 means the time it takes for the luminance to decrease to 80% from the initial luminance (7000 nit).

division Host Dopant Doping concentration% V Cd / ㎡ CIEx CIEy T ₈₀ (Hr) Comparative Example 1 CBP Ir (ppy) ₃ 10 7.93 3801 0.297 0.624 68 Example 1 2 Ir (ppy) ₃ 10 4.21 4948 0.264 0.631 162 Example 2 27 Ir (ppy) ₃ 10 4.19 5128 0.292 0.618 146 Example 3 45 Ir (ppy) ₃ 10 4.16 4876 0.279 0.629 129 Example 4 79 Ir (ppy) ₃ 10 4.30 4698 0.304 0.625 134 Example 5 107 Ir (ppy) ₃ 10 4.10 4909 0.312 0.627 169 Example 6 138 Ir (ppy) ₃ 10 4.61 4911 0.297 0.625 97 Example 7 239 Ir (ppy) ₃ 10 4.54 5030 0.291 0.621 167 Example 8 240 Ir (ppy) ₃ 10 4.15 5299 0.306 0.626 159 Example 9 272 Ir (ppy) ₃ 10 4.34 5119 0.286 0.619 187 Example 10 282 Ir (ppy) ₃ 10 4.47 4832 0.310 0.626 106

As shown in Table 1, the aromatic compound according to the present invention has a low driving voltage and excellent luminous efficiency as compared with CBP which is widely used as a phosphorescent host material.

<Examples 11 to 13> Preparation of an organic light emitting display device including the compound synthesized in Synthesis Examples 11 to 13

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After mounting the substrate in a vacuum chamber, the base pressure is 1 × 10 ^-6 torr, and then the organic material is synthesized on the ITO by DNTPD (700 kPa), NPD (300 kPa), the synthesis examples 11 to 13 + (piq ) ₂ Ir (acac) (10%) (300 Å), Alq ₃ (350 Å), LiF (5 Å), Al (1,000 Å) was formed in the order of, was measured at 0.4 mA.

The structure of (piq) ₂ Ir (acac) is as follows.

[(piq) ₂ Ir (acac)]

<Example 14> [Chemical Formula 295] was used for the light emitting layer in the device structure of Examples 11 to 13, and was manufactured in the same manner except that [PTOEP] was used instead of [(piq) ₂ Ir (acac)] [ PTOEP] has the following structure.

[PTOEP]

Comparative Example 2

An organic light emitting diode device for Comparative Example 2 was manufactured in the same manner as in Example 11 to 13 except for using CBP instead of the compound prepared according to the present invention as a host material.

For organic light emitting diodes manufactured according to Examples 11 to 14 and Comparative Example 2, voltage, current density, luminance, color coordinates, and lifetime were measured, and the results are shown in the following [Table 2]. T90 refers to the time taken for the luminance to decrease to 90% from the initial luminance (3700nit).

division Host Dopant Doping concentration% V Cd / ㎡ CIEx CIEy T ₉₀ (Hr) Example 11 292 (piq) &lt; / RTI &gt; ₂ Ir (acac) 10 4.4 1420 0.667 0.331 1320 Example 12 293 (piq) &lt; / RTI &gt; ₂ Ir (acac) 10 4.0 1510 0.675 0.323 1270 Example 13 295 (piq) &lt; / RTI &gt; ₂ Ir (acac) 10 4.1 1480 0.670 0.328 1230 Example 14 295 PTOEP 10 4.1 1470 0.655 0.343 1220 Comparative Example 2 CBP (piq) &lt; / RTI &gt; ₂ Ir (acac) 10 7.5 410 0.667 0.328 140

Claims (11)

An aromatic compound represented by the following formula (1):
[Chemical Formula 1]

In [Formula 1],
X ₁ to X ₅ are the same as or different from each other, each independently selected from N or CR ₁ , at least one of X ₁ to X ₅ is N,
R ₁ is a substituted or unsubstituted C ₁ -C ₃₀ alkyl group, a substituted or unsubstituted C ₆ -C ₄₀ aryl group, a substituted or unsubstituted C ₃ -C ₅₀ heteroaryl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₆ -C ₃₀ aryloxy group, substituted or unsubstituted C ₁ -C ₂₀ alkylamino group, substituted or unsubstituted C ₆ -C ₃₀ aryl Amino group, substituted or unsubstituted C ₁ -C ₂₀ alkylsilyl group, substituted or unsubstituted C ₆ -C ₃₀ arylsilyl group, substituted or unsubstituted C ₁ -C ₅₀ arylalkylamino group, substituted or unsubstituted Selected from the group consisting of a substituted C ₂ -C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₄₀ alkynyl group, a cyano group, a halogen group, a small to medium number and hydrogen,
R ₂ to R ₁₁ are the same as or different from each other, and each independently hydrogen, deuterium, a C ₁ -C ₂₀ alkyl group, a C ₆ -C ₄₀ aryl group, a C ₃ -C ₅₀ heteroaryl group, C ₁ -C ₂₀ Alkoxy group, C ₆ -C ₃₀ aryloxy group, C ₁ -C ₂₀ alkylamino group, C ₆ -C ₃₀ arylamino group, C ₁ -C ₂₀ alkylsilyl group, C ₆ -C ₃₀ arylsilyl A group, a C ₁ -C ₅₀ arylalkylamino group, a C ₂ -C ₄₀ alkenyl group, a C ₂ -C ₄₀ alkynyl group, a cyano group, a halogen group, a small to medium number and hydrogen,
L is a single bond or a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylene group having 2 to 60 carbon atoms Substituted or unsubstituted C2-C60 alkynylene groups, substituted or unsubstituted C3-C60 alkynylene groups, substituted or unsubstituted C2- Selected from the group consisting of a cycloalkylene group, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms N is an integer between 1 and 3, and when n is 2 or more, a plurality of Ls are the same or different. The method of claim 1,
The R ₂ to R ₁₁ is connected to each other with an adjacent substituent to form a condensed ring aromatic compound. The method of claim 1,
When the R ₁ is a plurality, a plurality of R ₁ are the same or different from each other, and are connected to a substituent adjacent to each other to form an alicyclic, aromatic monocyclic or polycyclic ring, characterized in that. The method of claim 3,
The aromatic compound, characterized in that the carbon atoms of the alicyclic, aromatic monocyclic or polycyclic ring formed is substituted with any one or more heteroatoms selected from N, S and O. The method of claim 1,
The L is an aromatic compound, characterized in that any one selected from [formula 1] to [formula 6]:
[Structural formula 1] [Structural formula 2] [Structural formula 3]

[Structural formula 4] [Structural formula 5] [Structural formula 6]

In the above Structural Formulas 1 to 6,
T ₁ to T ₈ are the same or different and each independently selected from C (R ₄₁ ), C (R ₄₂ ) (R ₄₃ ), N, N (R ₄₄ )
R ₃₁ to R ₄₄ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted group Any one selected from an aryl group having 5 to 50 carbon atoms and a heteroaryl group having 2 to 50 carbon atoms substituted or unsubstituted and having O, N or S as a hetero atom,
The R ₃₁ to R ₄₄ One is to form a single bond with the nitrogen of [Formula 1]. The method of claim 5,
[Formula 1] to [Formula 6] is an aromatic compound, characterized in that any one selected from the following [formula 7]:
[Structure 7]

In the above formula 7,
X is the same as X ₁ to X ₁₄ , m is an integer of 1 to 11, when m is 2 or more, a plurality of X is the same or different from each other, any one of the at least one X is in the formula [1] It combines with nitrogen to form a single bond. The method of claim 1,
[Formula 1] is an aromatic compound, characterized in that any one selected from the group of compounds represented by the following [Formula 2] to [Formula 296]:

[Chemical Formula 2] &lt; EMI ID =

[Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9]

[Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13]

[Chemical Formula 14] [Chemical Formula 15]

[Chemical Formula 20] [Chemical Formula 20]

[Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 25]

[Chemical Formula 28] [Chemical Formula 28]

[Chemical Formula 32] [Chemical Formula 32]

[Chemical Formula 35] [Chemical Formula 35]

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

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

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

[Chemical Formula 48] [Chemical Formula 49] [Chemical Formula 50]

[Chemical Formula 51]

[Chemical Formula 55] [Chemical Formula 55]

[Chemical Formula 55] [Chemical Formula 55]

[Chemical Formula 60] [Chemical Formula 61] [Chemical Formula 62]

[Chemical Formula 65] [Chemical Formula 65]

[Chemical Formula 70] [Chemical Formula 70]

[Chemical Formula 72] [Chemical Formula 73] [Chemical Formula 74]

[Formula 75] &lt; EMI ID = 78.1 &gt;

[Formula 80] [Formula 81] [Formula 82]

[Formula 83] [Formula 85] [Formula 86]

[Formula 90] [Formula 90] [Formula 90]

[Chemical Formula 91] [Chemical Formula 93] [Chemical Formula 94]

[Chemical Formula 97] [Chemical Formula 97] [Chemical Formula 98]

[Chemical Formula 100] [Chemical Formula 101] [Chemical Formula 101]

[Formula 103] [Formula 105] [Formula 106]

[Formula 110] [Formula 110] [Formula 110]

[Formula 111] [Formula 113] [Formula 114]

[Chemical Formula 116] [Chemical Formula 117] [Chemical Formula 118]

[Chemical Formula 120]

[Formula 124] [Formula 125] [Formula 126]

[Formula 127] &lt; EMI ID = 129.0 &gt;

[Formula 131] [Formula 133] [Formula 134]

[Chemical Formula 135] [Chemical Formula 135]

[Formula 140] [Formula 141] [Formula 142]

[Chemical Formula 144] [Chemical Formula 145] [Chemical Formula 146]

[Formula 150] [Formula 149] [Formula 150]

[Formula 154] [Formula 154] [Formula 154]

[Formula 157] &lt; EMI ID = 158.1 &gt;

[Formula 161] [Formula 161] [Formula 161]

[Formula 166] [Formula 166] [Formula 166]

[Formula 16] [Formula 16]

[Formula 173] [Formula 174] [Formula 174]

[Formula 177] [Formula 177] [Formula 178]

[Formula 181] [Formula 181] [Formula 182]

[Formula 184] [Formula 184] [Formula 186] [Formula 186]

[Formula 188] [Chemical Formula 189] [Chemical Formula 190]

[193] [193] [193] [194]

[Formula 195] [Formula 196] [Formula 197] [Formula 198]

[Chemical Formula 200] [Chemical Formula 201] [Chemical Formula 202]

[Chemical Formula 203]

[Chemical Formula 20] [Chemical Formula 20] [Chemical Formula 20]

[Chemical Formula 212] [Chemical Formula 213] [Chemical Formula 214]

[Formula 21] [Formula 21] [Formula 21]

[Formula 21] &lt; EMI ID =

[Formula 226] [Formula 226] [Formula 226]

[228] [230] [229]

[Formula 231] [Formula 234] [Formula 235] [Formula 236]

[Formula 237] [Formula 238] [Formula 239] [Formula 240]

[Formula 241] [Formula 242] [Formula 243] [Formula 244]

[Formula 245] [Formula 246] [Formula 247] [Formula 248]

[Formula 249] [Formula 250] [Formula 251] [Formula 252]

[Formula 253] [Formula 254] [Formula 255] [Formula 256]

[Formula 257] [Formula 258] [Formula 259] [Formula 260]

[Formula 261] [Formula 262] [Formula 263] [Formula 264]

[Formula 265] [Formula 266] [Formula 267] [Formula 268]

[Formula 269] [Formula 270] [Formula 271] [Formula 272]

[Formula 273] [Formula 274] [Formula 275] [Formula 276]

[Formula 277] [Formula 278] [Formula 279] [Formula 280]

[Formula 280] [Formula 281] [Formula 282] [Formula 283]

[Formula 284] [Formula 285] [Formula 286] [Formula 287]

[Formula 288] [Formula 289] [Formula 290] [Formula 291]

[Formula 292] [Formula 293] [Formula 294] [Formula 295] [Formula 296] A first electrode; A second electrode facing the first electrode; And at least one organic layer interposed between the first electrode and the second electrode,
The organic layer is an organic light emitting device, characterized in that it comprises at least one aromatic compound represented by [Formula 1] according to claim 1. 9. The method of claim 8,
Wherein the organic layer comprises one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light emitting layer, an electron transport layer and an electron injection layer. 10. The method of claim 9,
The emission layer includes at least one host compound and at least one dopant compound, wherein the host compound is an aromatic compound represented by the formula [1]. 9. The method of claim 8,
Wherein the organic layer further comprises one or more organic light emitting layers emitting red, green, or blue light to emit white light.

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