KR20200116873A - Aromatic compound and organoelectroluminescent device comprising the compound - Google Patents

Abstract

The present invention relates to an aromatic compound and an organic electroluminescent device including the same. The aromatic compound is represented by chemical formula 1, and the organic electroluminescent device is excellent in driving voltage, luminous efficiency and lifetime characteristics.

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. The organic electroluminescent device including the aromatic compound according to the present invention has a low driving voltage and excellent luminous efficiency.

An organic electroluminescent device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made 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 formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground. These organic electroluminescent devices are known to have characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

Materials used as the organic material layer in the organic electroluminescent device can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like, according to their functions. The light-emitting material may be classified into a high-molecular-type and a low-molecular-type according to its molecular weight, and may be classified into a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the electron according to the light emitting mechanism. . In addition, the light-emitting material may be classified into blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary for realizing a better natural color according to the light-emitting color.

On the other hand, when only one material is used as a light-emitting material, the maximum emission wavelength shifts to a long wavelength due to intermolecular interactions, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect.Therefore, the increase in color purity and energy transfer A host-dopant system may be used as a light-emitting material in order to increase the luminous efficiency through.

The principle is that when a small amount of a dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, 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 moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

Organic light-emitting devices are gradually expanding their application fields to the display and lighting fields of various electronic products, but efficiency and lifespan characteristics are limiting the expansion of the application field, and materials as well as devices are used to improve efficiency and lifespan characteristics. On the side, many studies are being conducted. In terms of materials, a host-dopant system is mainly used as a method for maximizing luminous efficiency, and a phosphorescent material is used for the dopant as a luminescent material, and CBP (4,4'-N, N'-dicarbazolbiphenyl) and substances in which various substituents are introduced into carbazole (Japanese Patent Publication 2008-214244, Japanese Patent Publication 2003-133075) are known, but additional improvements are required in terms of efficiency and lifespan characteristics.

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

The present invention provides an aromatic compound represented by the following [Chemical Formula 1] in order 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 [Chemical Formula 1].

A specific substituent of the above [Formula 1] will be described later.

Since the aromatic compound represented by [Chemical Formula 1] according to the present invention is stable compared to conventional materials and has excellent luminescence characteristics in driving voltage or current efficiency, etc., an organic electroluminescent device including the same can be driven at a low voltage and emit light. Efficiency can be improved.

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

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

The present invention is a light emitting layer host material having improved light emitting characteristics such as driving voltage, current efficiency, and lifetime characteristics of an organic light emitting device, 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 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, a cyano group, a halogen group, a small number and hydrogen.

When the R ₁ is plural, the plurality of R ₁ is the same or different from each other, and may be connected with a substituent adjacent to each other to form an alicyclic, aromatic monocyclic or polycyclic ring, and the formed alicyclic, aromatic group The carbon atom of the 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, a C ₁ -C ₂₀ Alkoxy group of, 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, may be selected from the group consisting of a small number and hydrogen, adjacent It is possible to form a condensed ring with a substituent group.

L is a linking group, which is a single bond or a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, and a substituted or unsubstituted C2 to C60 group Alkenylene group, substituted or unsubstituted alkynylene group having 2 to 60 carbon atoms, substituted or unsubstituted C3 to C60 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 And n is an integer between 1 and 3, and when n is 2 or more, a plurality of L may be the same or different.

According to an embodiment of the present invention, the R ₂ to R ₁₁ are each independently deuterium, a halogen atom, a hydroxy group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, hydrazone, a carboxyl group or a salt thereof, phosphoric acid Or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₆₀ 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.

On the other hand, the aryl group as 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 the aryl group has a substituent, it may be fused with neighboring substituents to further form a ring.

Specific examples of the aryl group 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- Ethylbiphenyl 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 anyl group, indenyl, fluorenyl group, tetrahydronaphthyl group, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl, and the like.

At least one hydrogen atom in the aryl group is a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a silyl group, an amino group (-NH ₂ , -NH(R), -N(R')(R"), R 'And R'are each independently an alkyl group having 1 to 10 carbon atoms, 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, Halogenated alkyl group having 1 to 24 carbon atoms, alkenyl group having 1 to 24 carbon atoms, alkynyl group having 1 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 6 to 24 carbon atoms, carbon number It may be substituted with a 2 to 24 heteroaryl group or a C 2 to 24 heteroarylalkyl group.

A heteroaryl group as a substituent used in the present invention, particularly in the case where L is a heteroarylene group as a divalent linking group as a heteroaryl group, may be any one substituent selected from the following [Structural Formula 1] to [Structural Formula 6] .

[Structural Formula 1] [Structural Formula 2] [Structural Formula 3]

[Structural Formula 4] [Structural Formula 5] [Structural Formula 6]

In the [Structural Formula 1] to [Structural Formula 6],

T ₁ to T ₈ are the same as or different from each other, and each independently, may be any one selected from C (R ₄₁ ), C (R ₄₂ ) (R ₄₃ ), N, N (R ₄₄ ), O and S, and , The R ₃₁ to R ₄₄ are the same 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 It may be any one selected from a C 5 to C 50 aryl group and a substituted or unsubstituted C 2 to C 50 heteroaryl group having O, N or S as a hetero atom, and each of [Structural Formula 1] to [Structural Formula In 6], one of R ₃₁ to R ₄₄ may be combined with nitrogen in the [Chemical Formula 1] to form a single bond.

In addition, the [Structural Formula 3] may include a compound represented by the following [Structural Formula 3-1] by a resonance structure according to the movement of electrons.

[Structural Formula 3-1]

In the [Structural Formula 3-1], T ₁ to T ₅ and R ₃₃ and R ₃₄ are the same as defined above.

In addition, according to a preferred embodiment of the present invention, the [Structural Formula 1] to [Structural Formula 6] may be selected from the following [Structural Formula 7].

[Structural Formula 7]

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

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

Specific examples of the alkoxy group as a substituent used in the present invention include a methoxy group, an ethoxy group, a propoxy group, an isobutyloxy group, a sec-butyloxy group, a pentyloxy group, an iso-amyloxy group, a hexyloxy group, and the like. May be substituted with the same substituent as in the case of the alkyl group.

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

The aryloxy group used in the present invention refers to an -O- aryl radical, wherein the aryl group is as defined above, and specific examples include phenoxy, naphthoxy, anthracenyloxy, phenanthrenyloxy, fluorenyl Oxy, indenyloxy, and the like, and one or more hydrogen atoms contained in the aryloxy group may be further substituted.

Specific examples of the silyl group as a substituent used in the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl, methylcyclobutylsilyl And dimethylfurylsilyl.

Specific examples of the alkenyl group used in the present invention represent a linear or branched alkenyl group, 3-pentenyl group, 4-hexenyl group, 5-heptenyl group, 4-methyl-3-pentenyl group, 2,4 -Dimethyl-pentenyl group, 6-methyl-5-heptenyl group, 2,6-dimethyl-5-heptenyl group, etc. are mentioned.

In addition, in the present invention, the'substituted' in the'substituted or unsubstituted' is 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, Alkenyl group having 1 to 24 carbon atoms, alkynyl group having 1 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 6 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms or carbon number 2 to 24 heteroarylalkyl group, C 1 to C 24 alkoxy group, C 1 to C 24 alkylamino group, C 1 to C 24 arylamino group, C 1 to C 24 hetero arylamino group, C 1 to C 24 alkylsilyl group, It means substituted with one or more substituents selected from the group consisting of 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 range of carbon atoms of the alkyl group or aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms", "substituted or unsubstituted aryl group having 5 to 50 carbon atoms", etc. considers the portion where the substituent is substituted It does not mean the total number of carbon atoms constituting the alkyl moiety or the aryl moiety when viewed as unsubstituted. For example, a phenyl group in which a butyl group is substituted in the para position corresponds to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

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

[Formula 47] [Formula 48] [Formula 49] [Formula 50]

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

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

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

[Chemical Formula 59] [Chemical Formula 60] [Chemical Formula 61] [Chemical 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]

[Chemical Formula 75] [Chemical Formula 76] [Chemical Formula 77] [Chemical 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]

[Chemical Formula 119] [Chemical Formula 120] [Chemical Formula 121] [Chemical Formula 122]

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

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

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

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

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

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

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

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

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

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

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

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

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

[Formula 175] [Formula 176] [Formula 177] [Formula 178]

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

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

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

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

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

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

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

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

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

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

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

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

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

[Formula 231] [Formula 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]

[Chemical Formula 277] [Chemical Formula 278] [Chemical Formula 279] [Chemical 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]

In addition, the present invention includes a first electrode, a second electrode opposite to 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 containing 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, an emission layer, an electron transport layer, and an electron injection layer. . At this time, the organic layer interposed between the first electrode and the second electrode may include a light emitting layer, the light emitting layer is made of a host and a dopant, and the aromatic compound of the present invention may be used as a host.

Meanwhile, in the present invention, a dopant material may be used in addition to a host for the emission layer. When the emission 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 may be used as the material for the electron transport layer, which has a function of stably transporting electrons injected from an electron injection electrode (Cathode). Examples of known electron transport materials include quinoline derivatives, in particular tris(8-quinolinorate)aluminum (Alq3), TAZ, Balq, beryllium bis(benzoquinolin-10-noate) (beryllium bis(benzoquinolin-10-). olate: Bebq2), ADN, [Compound 201], [Compound 202], and oxadiazole derivatives such as PBD, BMD, BND, and the like may be used.

TAZ BAlq

[Compound 201] [Compound 202] BCP

In addition, as for the electron transport layer used in the present invention, an organometallic compound represented by the following [Chemical Formula C] may be used alone or in combination with the electron transport layer material.

[Formula C]

In [Chemical Formula C],

Y is a portion in which any one selected from C, N, O, and S is directly bonded to the M to form a single bond, and a portion in which any one selected from C, N, O, and S forms a coordination bond to the M. It includes, and is a ligand chelated by the single bond and the coordination bond.

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

OA is a monovalent ligand capable of a single bond or coordination bond with M, wherein O is oxygen, and 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, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms Any one selected from an alkenyl group and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom.

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, n=0, and when M is boron or aluminum, m is any one of 1 to 3, and n is any one of 0 to 2, satisfying m+n=3.

'Substituted' in the'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group, alkoxy group, alkylamino group, arylamino group, hetero arylamino group, alkylsilyl group, arylsilyl group, It means substituted with one or more substituents selected from the group consisting of aryloxy group, aryl group, heteroaryl group, germanium, phosphorus and boron.

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

[Structural Formula C1] [Structural Formula C2] [Structural Formula C3]

[Structural Formula C4] [Structural Formula C5] [Structural Formula C6]

[Structural Formula C7] [Structural Formula C8] [Structural Formula C9] [Structural Formula C10]

[Structural Formula C11] [Structural Formula C12] [Structural Formula C13]

[Structural Formula C14] [Structural Formula C15] [Structural Formula C16]

[Structural Formula C17] [Structural Formula C18] [Structural Formula C19] [Structural Formula C20]

[Structural Formula C21] [Structural Formula C22] [Structural Formula C23]

[Structural Formula C24] [Structural Formula C25] [Structural Formula C26]

[Structural Formula C27] [Structural Formula C28] [Structural Formula C29] [Structural Formula C30]

[Structural Formula C31] [Structural Formula C32] [Structural Formula C33]

[Structural Formula C34] [Structural Formula C35] [Structural Formula C36]

[Structural Formula C37] [Structural Formula C38] [Structural Formula C39]

In the [Structural Formula C1] to [Structural Formula C39],

R is the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted A heteroaryl group having 3 to 30 carbon atoms, 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 C1-C30 alkylamino group, substituted or unsubstituted C1-C30 alkylsilyl group, substituted or unsubstituted C6-C30 arylamino group, and substituted or unsubstituted C6-C30 arylsilyl It is selected from groups, and may be connected to an adjacent substituent with alkylene or alkenylene to form a spiro ring or a fused ring.

L is 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 C 5 to 30 carbon atom Selected from a heteroaryl group and a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms, wherein 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, and 3 to 20 carbon atoms It is further substituted with one or more substituents selected from a heteroaryl group, a cyano group, a halogen group, deuterium and hydrogen, and may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring.

Hereinafter, the organic electroluminescent 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 light emitting 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 light emitting layer 50, an electron transport layer 60, and a cathode 80, and if necessary, the hole injection layer 30 and An electron injection layer 70 may be further included, and in addition to that, a first or second intermediate layer may be further formed, and a hole blocking layer or an electron blocking layer may be further formed.

Referring to FIG. 1, an organic light emitting device of the present invention and a method of manufacturing the same will be described as follows.

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

The hole injection layer 30 is formed by vacuum thermal evaporation or spin coating on the anode 20 electrode. Then, the hole transport layer material is vacuum thermally evaporated or spin coated on the hole injection layer 30 to form the hole transport layer 40.

The hole injection layer material is not particularly limited as long as it is commonly used in the art, and may be used, for example, 2-TNATA [4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine] , NPD[N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD[N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'- biphenyl-4,4'-diamine], DNTPD[N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine ], etc. can be used.

In addition, the material of the hole transport layer is not particularly limited as long as it is commonly used in the art. For example, N,N'-bis(3-methylphenyl)-N,N'-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.

Subsequently, an organic light-emitting layer 50 is stacked on the hole transport layer 40, and a hole blocking layer (not shown) is selectively formed on the organic light-emitting layer 50 by vacuum deposition or spin coating to form a thin film. can do. The hole blocking layer plays a role of preventing this problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level because when holes pass through the organic light emitting layer and flow into the cathode, the life and efficiency of the device are reduced. . In this case, the hole blocking material to be used is not particularly limited, but must have an electron transport ability and an ionization potential higher than that of the light emitting compound, and representatively, BAlq, BCP, TPBI, etc. may be used.

As a material used for the hole blocking layer, any one selected from BAlq, BCP, Bphen, TPBI, NTAZ, BeBq ₂ , OXD-7, Liq, and [Formula 101] to [Formula 107] may be used, but limited thereto It does not become.

BAlq BCP Bphen

TPBI NTAZ BeBq ₂

OXD-7 Liq

Formula 101 Formula 102 Chemical Formula 103

Formula 104 Formula 105 Formula 106

Chemical Formula 107

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

In addition, the emission layer may be formed of a host and a dopant, and according to a specific example of the present invention, the thickness of the emission layer is preferably 50 to 2,000 Å.

In this case, the dopant used in the light emitting layer may be one or more compounds selected from compounds represented by the following [General Formula A-1] to [General Formula J-1].

[General 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.

In addition, the L ₁ , L ₂ and L ₃ may be the same as or different from each other as a ligand, and each independently may be any one selected from the following [Structural Formula D], and "*" in the following Structural Formula D is coordinated to the metal ion M Express the site.

[Structural Formula D]

In the [Structural Formula D],

R is different from each other or the same, and each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted carbon number 5 to 50 heteroaryl group, substituted or unsubstituted C 1 to C 30 alkoxy group, substituted or unsubstituted C 3 to C 30 cycloalkyl group, substituted or unsubstituted C 2 to C 30 alkenyl group, substituted or unsubstituted A substituted or unsubstituted alkylamino 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 It may be any one selected from, and wherein R is each independently 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, a heteroaryl group having 3 to 20 carbon atoms, a cyano group, a halogen Group, deuterium and hydrogen may be further substituted with one or more substituents selected from, and the R is connected to each of the adjacent substituents by alkylene or alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring. I can.

L is 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 C 5 to 30 carbon atom Selected from a heteroaryl group and a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms, wherein 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, and 3 to 20 carbon atoms It is further substituted with one or more substituents selected from a heteroaryl group, a cyano group, a halogen group, deuterium and hydrogen, and may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring.

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

[General Formula B-1]

In the above [general formula B-1],

M ^A1 represents the same metal ion as defined in [General Formula A-1], and Y ^A11 , Y ^A14 , Y ^A15 and Y ^A18 each independently represent a carbon atom or a nitrogen atom, and Y ^A12 , Y ^A13 , Y ^A16 and Y ^A17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom, and a sulfur atom, and L ^A11 , L ^A12 , L ^A13 , L ^A14 are each of the above [General Formulas A-1] represents a linking group such as L ₁ , L ₂ and L _3, and Q ^A11 and Q ^A12 represent partial structures containing an atom bonded to M ^A1 .

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

[General Formula C-1]

In the above [general formula C-1],

M ^B1 represents the same metal ion as defined in [General Formula A-1], Y ^B11 , Y ^B14 , Y ^B15 and Y ^B18 each independently represent a carbon atom or a nitrogen atom, and Y ^B12 , Y ^B13 , Y ^B16 and Y ^B17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom, and a sulfur atom, L ^B11 , L ^B12 , L ^B13 , L ^B14 represent a linking group, Q ^B11 , Q ^B12 represents a partial structure containing an atom bonded to M ^B1 .

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

[General Formula D-1]

In the above [general formula D-1],

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

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

[General Formula E-1]

In the above [general formula E-1],

M ^D1 represents the same metal ion as defined in [General Formula A-1], and 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 required to form a 5-membered ring, and L ^D11 and L ^D12 represent a linking group.

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

[General Formula F-1]

In the above [general formula F-1],

M ^E1 represents the same metal ion as defined in [General Formula A-1], and J ^E11 and J ^E12 each independently represent an atomic group required to form a 5-membered ring, 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 an embodiment of the present invention, the compound represented by [General Formula F-1] may be any one selected from the following compounds.

[General Formula G-1]

In the above [general formula G-1],

M ^F1 represents the same metal ion as defined in [General Formula A-1], L ^F11 , L ^F12 and L ^F13 represent a linking group, R ^F11 , R ^F12 , R ^F13 and R ^F14 represent a substituent, and R ^F11 and R ^F12 , R ^F12 and R ^F13 , R ^F13 and R ^F14 may be linked 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 an embodiment of the present invention, the compound represented by [General Formula G-1] may be any one selected from the following compounds.

[General Formula H-1] [General Formula H-2] [General 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, and may form a fused ring with a substituent adjacent to each other, and q11 and q12 are integers of 0 to 4, preferably 0 to 2. Further, when q11 and q12 are 2 to 4, a plurality of R11 and R12 may be the same or different, respectively.

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

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

In addition, it is preferable that n ¹ and m ¹ make the metal complex represented by the above [General Formula H-1] a neutral complex.

In the above [General Formula H-2],

R ²¹ , R ²² , n ² , m ² , q ²² , 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 the above [General Formula H-3],

R ³¹ , n ³ , m ³ , L ³ are the same as R ¹¹ , n ¹ , m ¹ , and L ¹ , respectively, and q ³¹ represents an integer of 0 to 8, preferably 0 to 2, and more than 0 desirable.

According to an embodiment of the present invention, the compound represented by [General Formula H-1] to [General Formula H-3] may be any one selected from the following compounds.

[General Formula I-1]

In the above [general formula I-1],

Ring A, Ring B, Ring C, and Ring D represent a nitrogen-containing heterocycle in which any two of the rings A to D may have a substituent, and the other two rings are an aryl ring or heteroaryl which may have a substituent. Represents a ring, and can form a condensed ring with ring A and ring B, ring A and ring C, and/or ring B and ring D.

X ¹ , X ² , X ³ and X ⁴ represent a nitrogen atom in which 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 (term) or a bond, but Q ¹ , Q ² and Q ³ do not represent a bond at the same time. Z ¹ , Z ² , Z ³ and Z ⁴ are any two representing a coordination bond, and the other two represent a covalent bond, an oxygen atom or a sulfur atom.

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

[General Formula J-1]

In the above [general formula J-1],

M represents the same metal ion as defined in [General Formula A-1], Ar1 represents a substituted or unsubstituted ring structure, and two azomethine bonds (-C=N-) bonded to the M In ), the nitrogen atom (N) is each bonded to the M, and as a whole, forms a tridentate ligand bonded to the M at three loci.

In addition, in Ar1, C represents a carbon atom constituting the ring structure represented by Ar1. In addition, R1 and R2 may be the same as or different from each other, and each represents a substituted or unsubstituted alkyl group or aryl group, and L represents a monodentate ligand.

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

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

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

In addition, at least one layer selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer 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 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 inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating, etc., by mixing a material to be formed with a solvent.

In addition, the organic electroluminescent device according to the present invention may be used in a device selected from a flat panel display device, a flexible display device, a monochrome or white flat lighting device, and a single color or white flexible lighting device.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for explaining the present invention in more detail, and it will be apparent to those of ordinary skill in the art that the scope of the present invention is not limited thereto.

Synthesis example 1. Synthesis of Formula 2

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

<1-a> was synthesized according to the following Scheme 1.

[Scheme 1]

<1-a>

In a 5000 mL round-bottom flask under nitrogen, 87 g (0.576 mol) of methyl anthranirate, 135.1 g (0.478 mol) of 1-bromo-4-iodobenzene, and 1.3 g (0.006 of palladium acetate (Pd(OAc) ₂ )) mol), Xantphos 10 g (0.017 mol), cesium carbonate 217.5 g (0.668 mol), and 2500 mL of toluene were added and refluxed for 6 hours. When the reaction was completed, the reaction product was separated into layers to remove an aqueous layer, and the organic layer was separated and concentrated under reduced pressure, and <1-a> 110 g (75%) was obtained through column chromatography.

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

<1-b> was synthesized according to Scheme 2 below.

[Scheme 2]

<1-b>

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

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

<1-c> was synthesized according to Scheme 3 below.

[Scheme 3]

<1-c>

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

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

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

[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 stirred, and the temperature of the reaction product 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 dropwise addition, it was stirred at room temperature. When the reaction was completed, the reaction product was poured into water, stirred, filtered, and washed with water and methanol to obtain 76.4 g (51.9%).

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

<1-e> was synthesized according to Scheme 5 below.

[Scheme 5]

<1-e>

In a 2000 mL round bottom flask, 76.4 g (0.31 mol) of the compound represented by 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 resultant layer was separated to remove the aqueous layer, and the organic layer was separated and concentrated under reduced pressure, and then <1 -e> 76g (76%) was obtained.

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

<1-f> was synthesized according to Scheme 6 below.

[Scheme 6]

<1-f>

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

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

<1-g> was synthesized according to Scheme 7 below.

[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) of the compound represented by formula 1-f obtained from Scheme 6 tetrakis (triphenylphosphine) palladium (0) 1.2 g (0.001 mol), potassium carbonate 12.1 g (0.09 mol), toluene 50 mL, tetrahydrofuran 50 mL, and water 20 mL were added, followed by refluxing for 12 hours. When the reaction was completed, the reaction product was separated into layers to remove the aqueous layer, the organic layer was separated, concentrated under reduced pressure, and <1-g> 14.6g (93%) was obtained through column chromatography.

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

<1-h> was synthesized according to Scheme 8 below.

[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 nitrogen and refluxed 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. After the dropwise addition, it was refluxed for 2 hours and cooled to room temperature. In another 2L 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. Maintain the temperature of the reaction solution above and add it slowly dropwise. After completion of the reaction, the reaction was terminated with a 4 mol aqueous hydrochloric acid solution, extracted, and the organic layer was concentrated under reduced pressure and recrystallized with hexane to obtain 100 g (68.9%) of <1-h>.

Synthesis example 1-9. < 2> of synthesis

<2> was synthesized according to Scheme 9 below.

[Scheme 9]

<2>

In a 100 mL round bottom flask, 2 g of sodium hydride was dissolved in 200 mL of N,N-diethylamide and cooled to 0 degrees under nitrogen. 14.6 g (0.0324 mol) of the compound represented by Formula 1-g obtained from Scheme 7 at 0° C. was dissolved in 200 mL of N,N-diethylamide and slowly added dropwise. After dropwise addition, the mixture was stirred for 1 hour. 13 g (0.05 mol) of the compound represented by Formula 1-h obtained from Scheme 8 at 0° C. was dissolved in 200 mL of N,N-diethylamide and slowly added dropwise. After dropwise addition, it 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%) of <Chemical Formula 2>.

MS(MALDI-TOF): m/z 681.29[M] ⁺

¹³ C NMR (75 MHz, CDCl3) 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]

Synthesis example 2. Synthesis of Formula 27

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

<2-a> was synthesized according to Scheme 10 below.

[Scheme 10]

<2-a>

<2-a> 12.8g (78.5%) was obtained by synthesizing by the same method as the synthesis method for the compound represented by Chemical Formula 1-g.

Synthesis example 2-2. < 27> of synthesis

<27> was synthesized according to the following Scheme 11.

[Scheme 11]

<27>

It was synthesized in the same manner as for the synthesis of the compound represented by Chemical Formula 2 above to obtain 7.4g (34%).

MS(MALDI-TOF): m/z 566.25 [M] ⁺

¹³ C NMR (75 MHz, CDCl3) 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]

Synthesis example 3. Synthesis of Formula 45

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

<3-a> was synthesized according to Scheme 12 below.

[Scheme 12]

<3-a>

In a 500 mL round bottom flask, 20 g (0.06 mol) of the 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, 6.9 g (0.03 mol) of copper chloride and 160 mL of dimethyl sulfoxide was added and refluxed for 6 hours. When the reaction was completed, the reaction result was extracted, the organic layer was separated, concentrated under reduced pressure, and <3-a> 15.5 g (60%) was obtained through column chromatography.

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

<3-b> was synthesized according to Scheme 13 below.

[Scheme 13]

<3-b>

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

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

<3-c> was synthesized according to Scheme 14 below.

[Scheme 14]

<3-c>

<2-c> 8.5g (40%) was obtained by synthesizing in the same manner as the synthesis method for the compound represented by Chemical Formula 1-g.

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

<3-d> was synthesized according to Scheme 15 below.

[Scheme 15]

<3-d>

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

Synthesis example 3-5. < Of 45> synthesis

<45> was synthesized according to Scheme 16 below.

[Scheme 16]

<45>

It was synthesized in the same manner as the method for synthesizing the compound represented by Formula 2 above to obtain 8.2g (65.7%).

MS(MALDI-TOF): m/z 722.34 [M] ⁺

¹³ C NMR (75 MHz, CDCl3) 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]

Synthesis example 4. Synthesis of Formula 79

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

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

[Scheme 17]

In a 2000 mL round bottom flask, 100 g (0.543 mol) of diphenylthiophene and 800 mL of tetrahydrofuran were added under nitrogen and stirred for 30 minutes under nitrogen, and the temperature of the reaction was cooled to -78 degrees. 1.6 mol normal butyllithium 407 mL (0.65 mol) was slowly added dropwise. After stirring at room temperature for 24 hours, the temperature of the reaction was 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 a 2 mol aqueous hydrochloric acid solution, extracted, the organic layer was concentrated under reduced pressure, and then recrystallized with hexane to obtain 96.4 g (78%).

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

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

[Scheme 18]

<4-b>

Synthesis was carried out in the same manner as for the synthesis of the compound represented by Chemical Formula 1-h, and <4-b> 49.3g (65.5%) was obtained.

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

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

[Scheme 19]

<4-c>

<4-c> 10g (73.6%) was obtained by synthesizing in the same manner as for the synthesis of the compound represented by Chemical Formula 1-g.

Synthesis example 4-4. < 79> of synthesis

<79> was synthesized according to the following Scheme 20.

[Scheme 20]

<79>

Synthesis was performed in the same manner as for the synthesis of the compound represented by Chemical Formula 2 to obtain 7.8g (35.5%).

MS(MALDI-TOF): m/z 632.28 [M] ⁺

¹³ C NMR (75 MHz, CDCl3) 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]

Synthesis example 5. Synthesis of Formula 107

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

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

[Scheme 21]

<5-a>

It was synthesized in the same manner as the synthesis method for the compound represented by Formula 1-h above to obtain 47.6g (76%) of <5-a>.

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

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

[Scheme 22]

<5-b>

Synthesis was carried out in the same manner as the method for synthesizing the compound represented by Formula 2 above to obtain 38.4g (51.5%) of <5-b>.

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

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

[Scheme 23]

<5-c>

<5-c> 15.4g (72.3%) was obtained by synthesizing in the same manner as for the synthesis of the compound represented by Formula 2 above.

Synthesis example 5-4. < 107> of synthesis

<107> was synthesized according to Scheme 24 below.

[Scheme 24]

<107>

In a 1 L round bottom flask, 15.4 g (0.024 mol) of the compound represented by 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), triteributylphosphine 0.3g (0.01mol), potassium carbonate 6.8g (0.05mol) and xylene 400mL were added and refluxed for 12 hours. After the reaction was completed, extraction, 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, CDCl3) 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]

Synthesis example 6. Synthesis of Formula 138

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

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

[Scheme 25]

<6-a>

Synthesized by the same method as the synthesis method for the compound represented by Chemical Formula 1-h above to obtain 37.9g (61.8%) of <6-a>.

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

<6-b> was synthesized according to Scheme 26 below.

[Scheme 26]

<6-b>

Synthesis was carried out in the same manner as in the synthesis of the compound represented by Chemical Formula 2 above to obtain 43.2g (72.2%) of <6-b>.

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

<6-c> was synthesized according to Scheme 27 below.

[Scheme 27]

<6-c>

<6-c> 15g (84.9%) was obtained by synthesizing in the same manner as for the synthesis of the compound represented by Chemical Formula 1-g.

Synthesis example 6-4. < 138> of synthesis

<138> was synthesized according to Scheme 28 below.

[Scheme 28]

<138>

Synthesis was carried out in the same manner as the method for synthesizing the compound represented by Chemical Formula 2 above to obtain 9.8g (yield 36%).

MS(MALDI-TOF): m/z 708.26[M] ⁺

¹³ C NMR (75 MHz, CDCl3) 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]

Synthesis example 7. Synthesis of Formula 239

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

<7-a> was synthesized according to Scheme 29 below.

[Scheme 29]

<7-a>

<7-a> 40g (98%) was obtained by synthesizing in the same manner as the synthesis method for the compound represented by Formula 1-f above.

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

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

[Scheme 30]

<7-b>

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

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

<7-c> was synthesized according to Scheme 31 below.

[Scheme 31]

<7-c>

In a 1 L round bottom flask, to 20 g (0.045 mol) of the compound represented by 7-b obtained in Scheme 30, 250 mL of N,N-dimethylamide was added, stirred under nitrogen for 30 minutes, and the temperature of 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 dropwise addition, it 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 obtain 18.46 g (78%) of the compound represented by Formula 7-c.

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

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

[Scheme 32]

<7-d>

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

Synthesis example 7-5. < 239> of synthesis

<239> was synthesized according to Reaction Scheme 33 below.

[Scheme 33]

<239>

Synthesis was performed in the same manner as for the synthesis of the compound represented by Chemical Formula 2 above to obtain 7.9g (39.2%).

MS(MALDI-TOF): m/z 856.27 [M] ⁺

¹³ C NMR (75 MHz, CDCl3) 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]

Synthesis example 8. Synthesis of Formula 240

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

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

[Scheme 34]

<8-a>

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

Synthesis example 8-2. < 240> of synthesis

<240> was synthesized according to Scheme 35 below.

[Scheme 35]

<240>

Synthesis was performed in the same manner as for the synthesis of the compound represented by Chemical Formula 2 to obtain 6.3g (40%).

MS(MALDI-TOF): m/z 724.28 [M] ⁺

¹³ C NMR (75 MHz, CDCl3) 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]

Synthesis example 9. Synthesis of Formula 272

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

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

[Scheme 36]

<9-a>

Synthesis was performed in the same manner as for the synthesis of the compound represented by Chemical Formula 4-a, to obtain 99.1g (78.6%) of <9-a>.

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

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

[Scheme 37]

<9-b>

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

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

<9-c> was synthesized according to Scheme 38 below.

[Scheme 38]

<9-c>

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

Synthesis example 9-4. < 272> of synthesis

<272> was synthesized according to Scheme 39 below.

[Scheme 39]

<272>

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

MS(MALDI-TOF): m/z 772.28 [M] ⁺

¹³ C NMR (75 MHz, CDCl3) 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]

Synthesis example 10. Synthesis of Formula 282

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

<10-a> was synthesized according to Scheme 40 below.

[Scheme 40]

<10-a>

In a 5L round-bottom flask, add 200g (0.73mol) of 2-bromo-9,9'-dimethylfluorene and 2400mL of tetrahydrofuran, stir for 30 minutes under nitrogen, and cool the reaction product to -78 degrees. 549 mL (0.88 mol) of 1.6 mol normal butyl lithium was slowly added dropwise. After stirring at room temperature for 24 hours, the temperature of the reaction was 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 the reaction was completed, the reaction was terminated with an aqueous sodium thiosulfate solution, extracted, the organic layer was concentrated under reduced pressure, and then separated by column chromatography using hexane to give 209 g (89%) of <10-a>.

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

<10-b> was synthesized according to Scheme 41 below.

[Scheme 41]

<10-b>

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

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

<10-c> was synthesized according to Scheme 42 below.

[Scheme 42]

<10-c>

In a 2L round-bottom flask, 70 g (0.19 mol) of the compound represented by 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, and potassium carbonate 53.1 g (0.384 mol) and 700 mL of N,N-dimethylacetamide were added and refluxed for 12 hours. After completion of the reaction, extraction, the organic layer was concentrated under reduced pressure, recrystallized with hexane, and dried to give 46.3 g (85%) of <10-c>.

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

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

[Scheme 43]

<10-d>

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

Synthesis example 10-5. < 282> of synthesis

<282> was synthesized according to Scheme 44 below.

[Scheme 44]

<282>

Synthesis was performed in the same manner as for the synthesis of the compound represented by Chemical Formula 107 to obtain 7.8g (40%).

MS(MALDI-TOF): m/z 873.38 [M] ⁺

¹³ C NMR (75 MHz, CDCl3) δ:

21.3 30.9 45.5 50.1 105.4 109.5 110.9 114.4 116 118.7 119.8 119.9 120.2 121.4 121.6 123.2 126.6 126.7 127.5 128.1 129 129.1 129.2 129.5 129.6 129.7 130.5 131.1 131.9 132.4 133 133.9 134 134.7 135.5 135.9 137.1 141 144.7 145.4 147.8 172.2 178.2 [63C]

Synthesis example 11. Synthesis of Formula 292

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

<11-a> was synthesized according to Scheme 45 below.

[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, followed by stirring. 112.9 mL (339 mmol) of phenyl magnesium bromide (3.0 M in Et ₂ O) was added dropwise. After stirring at reflux for about 1 hour, the temperature was set to 0°C. Ethyl chloroformate (22.0g, 203mmol) was added dropwise and stirred under reflux for about 1 hour. An aqueous ammonium chloride solution was added until it became slightly acidic, and the resulting solid was filtered and washed with water and heptane to obtain 30.1 g of <11-a>. (Yield: 80%)

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

<11-b> was synthesized according to Scheme 46 below.

[Scheme 46]

<11-b>

At room temperature, the synthesized [Intermediate 11-a] (30.0 g, 135 mmol) and about 80 mL of phosphorus oxychloride were added to a round bottom flask under a nitrogen stream and stirred. After reflux stirring overnight, the temperature was cooled to -20℃ the next day, and water was slowly added dropwise about 400mL. The resulting solid was filtered and washed with water, methanol, and heptane. 14.6 g of <11-b> was obtained by recrystallization from toluene and heptane. (Yield: 44.9%)

Synthesis example 11-3. < 292> of synthesis

<292> was synthesized according to Scheme 47 below.

[Scheme 47]

<292>

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

MS(MALDI-TOF): m/z 654.28[M] ⁺

¹³ C NMR (75 MHz, CDCl3) 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]

Synthesis example 12. Synthesis of Formula 293

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

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

[Scheme 48]

<12-a>

Under a stream of nitrogen, 1-nitronaphthalene (50.0 g, 289 mmol), ethyl cyanoacetate (98.0 g, 866 mmol), potassium cyanide (20.7 g, 318 mmol), potassium hydroxide (32.4 g, 577 mmol) in a round bottom flask immersed in water And stirred. 100 mL of dimethylformamide was added, the temperature was raised to 60° C., and the mixture was stirred overnight. The next day, the change of TLC was checked and the temperature of the flask was set to room temperature. The reaction solution was concentrated under reduced pressure to remove all possible dimethylformamide. The concentrate was transferred to a reactor with a small amount of dichloromethane, and 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. It was separated by column chromatography using ethyl acetate and heptane. Recrystallized from toluene and heptane to give 24.6 g (yield 50.7%) of <12-a> as a white solid.

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

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

[Scheme 49]

<12-b>

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

Synthesis example 12-3. < 293> of synthesis

<293> was synthesized according to the following Scheme 50.

[Scheme 50]

<293>

[Chemical Formula 293] 5.8g (46%) was obtained by using the synthesized <12-b> instead of <1-h> used in [Scheme 9].

MS(MALDI-TOF): m/z 704.29[M] ⁺

¹³ C NMR (75 MHz, CDCl3) 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 [51C]

Synthesis example 13. Synthesis of Formula 295

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

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

[Scheme 51]

<13-a>

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

Synthesis example 13-2. < 295> of synthesis

<295> was synthesized according to the following Scheme 52.

[Scheme 52]

<295>

[Chemical Formula 295] 5.2g (41%) was obtained by using the synthesized <13-a> instead of <1-h> used in [Scheme 9].

MS(MALDI-TOF): m/z 704.29[M] ⁺

¹³ C NMR (75 MHz, CDCl3) 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 an organic light emitting diode

The ITO glass was patterned so that the light emitting area was 2 mm × 2 mm in size and washed. After mounting the substrate in a vacuum chamber, the base pressure was 1×10 ^-6 torr, and then the organic material was placed on the ITO with DNTPD (700Å), NPD (300Å), 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) were formed in the order, and 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 fabricated in the same manner as in the device structures of Examples 1 to 10 except that CBP, which is generally used as a phosphorescent host material, was used instead of the compound prepared by the invention. The structure is as follows.

<CBP>

For the organic electroluminescent devices 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 Table 1 below. T80 refers to the time it takes for the luminance to decrease from the initial luminance (7000nit) to 80%.

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 lower driving voltage and excellent luminous efficiency than CBP, which is widely used as a phosphorescent host material.

<Examples 11 to 13> Preparation of organic electroluminescent devices including compounds synthesized according to Synthesis Examples 11 to 13

The ITO glass was patterned so that the light emitting area was 2 mm × 2 mm in size and washed. After mounting the substrate in the vacuum chamber, the base pressure was 1×10 ^-6 torr, and then the organic material was placed on the ITO with DNTPD (700 Å), NPD (300 Å), the compound synthesized by Synthesis Examples 11 to 13 + (piq ) ₂ Ir (acac) (10%) (300 Å), Alq ₃ (350 Å), LiF (5 Å), Al (1,000 Å) were formed in the order, and measured at 0.4 mA.

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

[(piq) ₂ Ir(acac)]

<Example 14> In the device structures of Examples 11 to 13, [Chemical Formula 295] was used for the light emitting layer, and [PTOEP] was used instead of [(piq) ₂ Ir(acac)], and the same was produced [ The structure of [PTOEP] is as follows.

[PTOEP]

<Comparative Example 2>

The organic light emitting diode device for Comparative Example 2 was fabricated in the same manner as in the device structures of Examples 11 to 13, except that CBP was used instead of the compound prepared by the present invention as a host material.

For the organic electroluminescent devices prepared 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 Table 2 below. T90 refers to the time it takes for the luminance to decrease from the initial luminance (3700nit) to 90%.

division Host Dopant Doping concentration% V Cd/㎡ CIEx CIEy T ₉₀ (Hr) Example 11 292 (piq) ₂ Ir(acac) 10 4.4 1420 0.667 0.331 1320 Example 12 293 (piq) ₂ Ir(acac) 10 4.0 1510 0.675 0.323 1270 Example 13 295 (piq) 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) ₂ Ir(acac) 10 7.5 410 0.667 0.328 140

Claims (9)

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, each independently selected from N or CR ₁ , and 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 ₂ -C ₄₀ selected from the group consisting of alkenyl group, cyano group, halogen group, small number and hydrogen,
R ₂ to R ₉ 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, a C ₁ -C ₂₀ Alkoxy group of, 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, a C ₁ -C ₅₀ arylalkylamino group, a C ₂ -C ₄₀ alkenyl group, a C ₂ -C ₄₀ alkynyl group, a cyano group and a halogen group,
At least one of R ₂ to R ₉ is a C ₆ -C ₄₀ aryl group, a C ₃ -C ₅₀ heteroaryl group, a C ₆ -C ₃₀ aryloxy group, a C ₁ -C ₂₀ alkylamino group, C ₆ -C ₃₀ arylamino group, C ₁ -C ₂₀ alkylsilyl group, C ₆ -C ₃₀ arylsilyl group and C ₁ -C ₅₀ selected from the group consisting of arylalkylamino group,
R ₁₀ and R ₁₁ are the same as or different from each other, and each independently selected from the group consisting of a C ₁ -C ₂₀ alkyl group and a C ₆ -C ₄₀ aryl group,
L is a single bond, and n is an integer of 1. The method of claim 1,
The R ₂ to R ₁₁ is an aromatic compound, characterized in that the adjacent substituents are connected to each other to form a condensed ring. The method of claim 1,
When the number of R ₁ is plural, the plurality of R ₁ is the same or different from each other, and is connected with a substituent adjacent to each other to form an alicyclic, aromatic monocyclic or polycyclic ring. The method of claim 3,
An aromatic compound, characterized in that the formed alicyclic, aromatic monocyclic or polycyclic carbon atoms are substituted with any one or more heteroatoms selected from N, S and O. The method of claim 1,
[Chemical Formula 1] is an aromatic compound, characterized in that any one selected from the group of compounds represented by the following [Chemical Formula 2] to [Chemical 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]

[Formula 47] [Formula 48] [Formula 49] [Formula 50]

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

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

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

[Chemical Formula 59] [Chemical Formula 60] [Chemical Formula 61] [Chemical 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]

[Chemical Formula 75] [Chemical Formula 76] [Chemical Formula 77] [Chemical 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]

[Chemical Formula 119] [Chemical Formula 120] [Chemical Formula 121] [Chemical Formula 122]

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

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

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

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

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

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

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

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

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

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

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

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

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

[Formula 175] [Formula 176] [Formula 177] [Formula 178]

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

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

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

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

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

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

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

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

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

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

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

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

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

[Formula 231] [Formula 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]

[Chemical Formula 277] [Chemical Formula 278] [Chemical Formula 279] [Chemical 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 one or more organic layers interposed between the first electrode and the second electrode,
The organic layer is an organic electroluminescent device comprising at least one aromatic compound represented by [Chemical Formula 1] according to claim 1. The method of claim 6,
The organic layer comprises at least one layer selected from 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. The method of claim 7,
The emission layer includes at least one host compound and at least one dopant compound, and the host compound is an aromatic compound represented by [Chemical Formula 1]. The method of claim 6,
An organic electroluminescent device, characterized in that the organic layer further includes at least one organic emission layer emitting red, green, or blue light to emit white light.

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