KR102169442B1 - Organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Abstract

[화학식 1-1] [화학식 1-2]The present invention relates to an organic light emitting compound employed as a hole transport material, characterized in that represented by the following [Chemical Formula 1-1] to [Chemical Formula 1-2], and the organic light emitting compound according to the present invention is used as an organic light emitting device. When employed in the hole transport layer of, it is possible to manufacture an organic electroluminescent device with improved luminous efficiency and lifetime characteristics at the same time.

[Formula 1-1] [Formula 1-2]

Description

Organic electroluminescent compounds and organic electroluminescent device using the same}

The present invention relates to an organic light-emitting compound, and more specifically, to an organic light-emitting compound employed in a hole transport layer, and an organic light-emitting device having significantly improved long life and luminous efficiency by employing the same.

Organic light-emitting devices can not only form devices on a transparent substrate, but also can drive a low voltage of 10 V or less compared to plasma display panels or inorganic electroluminescent (EL) displays, and consume relatively little power. In addition, it has the advantage of excellent color sense, and can display three colors of green, blue, and red, which has recently attracted much attention as a next-generation display device.

However, in order for such an organic light emitting device to exhibit the above characteristics, the material forming the organic layer in the device, such as hole injection material, hole transport material, light emitting material, electron transport material, electron injection material, etc., is supported by a stable and efficient material. However, the development of an organic material layer material for a stable and efficient organic light emitting device has not been sufficiently developed until now. Accordingly, there is a situation in which the development of new materials capable of satisfying various light emitting characteristics is continuously required.

In particular, as conventional hole transport materials, copper phthalocyanine (CuPc), MTDATA, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-diphenyl- N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), etc., are known, but the problem of lowering luminous efficiency and lifespan when employing them in devices In order to improve this, an aromatic amine derivative compound having various substituents has been developed, but still has a problem that is not sufficient to simultaneously satisfy high luminous efficiency and long life.

Accordingly, an object of the present invention is to provide a novel organic light emitting compound having improved efficiency and lifespan characteristics compared to conventional hole transport materials at the same time, and an organic electroluminescent device having very excellent light emitting efficiency and lifespan characteristics by employing the same in the hole transport layer.

The present invention provides a novel organic light-emitting compound represented by the following [Chemical Formula 1-1] to [Chemical Formula 1-2] in order to solve the above problems.

[Formula 1-1] [Formula 1-2]

Each of the substituents of [Chemical Formula 1-1] to [Formula 1-2] and L will be described later.

In addition, the present invention is an organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode, the organic layer in the above [Formula 1-1] to [Formula 1- 2] provides an organic electroluminescent device comprising at least one or more of the various compounds embodied.

When the organic light-emitting compound according to the present invention is employed in a hole transport layer of an organic light-emitting device, it is possible to manufacture an organic light-emitting device having excellent luminous efficiency and lifespan characteristics of the device.

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.

One aspect of the present invention relates to an organic light emitting compound represented by the following [Formula 1-1] to [Formula 1-2].

[Formula 1-1] [Formula 1-2]

In the above [Formula 1-1] to [Formula 1-2],

A ₁ to A ₂₀ are each independently CX ₁ to CX _20, and two adjacent A of A ₁ to A ₂₀ are bonded to the L to form a condensed ring ([*] means a binding site).

The X ₁ to X ₂₀ are the same as or different from each other, and each independently the following [Formula Q], hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms , A substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted carbon number 1 to 60 The alkoxy group of, a substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms. It is selected from a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms.

However, at least one of the X ₁ to X ₂₀ is characterized in that the following [Formula Q].

[Formula Q]

In the above [Formula Q],

K is a single bond or a substituted or unsubstituted C 1 to C 30 alkylene group, a substituted or unsubstituted C 2 to C 30 Alkenylene group, substituted or unsubstituted C2-C30 alkynylene group, substituted or unsubstituted C3-C30 It is a linking group selected from a cycloalkylene group, a substituted or unsubstituted arylene group having 5 to 50 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, m is an integer of 0 to 4, wherein m is 2 or more In the case, a plurality of Ks may be the same or different from each other.

J ₁ and J ₂ are the same as or different from each other, and each independently, 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 carbon number of 2 to 30 of It is selected from an alkenyl group, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.

Z, W, Y and U are each independently CR ₁ R ₂ , NR ₃ , O, S, SiR ₄ R ₅ , GeR ₆ R ₇ or Se, and at least one of Z, W, Y and U is NR ₃ (however, n is an integer from 0 to 3).

R ₁ above To R ₇ are the same as or different from each other, and each independently of the above [Formula Q], hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or It is selected from unsubstituted C2 to C30 heteroaryl groups.

는 구체적으로 하기 [치환기 B1] 내지 [치환기 B46] 중에서 선택되는 어느 하나일 수 있다.In addition, in [Chemical Formula Q]

Specifically, may be any one selected from the following [substituent B1] to [substituent B46].

[Substituent B1] [Substituent B2] [Substituent B3]

[Substituent B4] [Substituent B5] [Substituent B6]

[Substituent B7] [Substituent B8] [Substituent B9]

[Substituent B10] [Substituent B11] [Substituent B12]

[Substituent B13] [Substituent B14] [Substituent B15]

[Substituent B16] [Substituent B17] [Substituent B18]

[Substituent B19] [Substituent B20] [Substituent B21]

[Substituent B22] [Substituent B23] [Substituent B24]

[Substituent B25] [Substituent B26] [Substituent B27]

[Substituent B28] [Substituent B29] [Substituent B30]

[Substituent B31] [Substituent B32] [Substituent B33]

[Substituent B34] [Substituent B35] [Substituent B36]

[Substituent B37] [Substituent B38] [Substituent B39]

[Substituent B40] [Substituent B41] [Substituent B42]

[Substituent B43] [Substituent B44] [Substituent B45]

[Substituent B46]

In the above [substituent B1] to [substituent B46],

R is hydrogen, deuterium, cyano group, halogen group, alkyl group having 1 to 6 carbon atoms, aryl group having 6 to 18 carbon atoms, arylalkyl group having 6 to 18 carbon atoms, heteroaryl group having 3 to 18 carbon atoms, alkyl having 1 to 12 carbon atoms A silyl group, an arylsilyl group having 6 to 18 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 18 carbon atoms, n is an integer of 0 to 12 , When n is 2 or more, a plurality of Rs are the same as or different from each other, and may be fused with adjacent substituents to form a ring, and * means a site that binds to K in [Chemical Formula Q].

In addition, in [Chemical Formula Q], K may be any one selected from the following [Structural Formula C1] to [Structural Formula C14].

[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]

In the [Structural Formula C1] to [Structural Formula C14],

Hydrogen or deuterium may be bonded to the carbon site in the ring of each structural formula, and R is the same as the definition of X ₁ to X ₂₀ in [Formula 1-1] to [Formula 1-2].

In addition, the'substituted'in'substituted or unsubstituted' in the present invention means that the substituents such as X ₁ to X ₂₀ , R ₁ to R ₇ , K and J ₁ to J ₂ are each independently deuterium, cyano group, halogen Group, hydroxy group, nitro group, alkyl group having 1 to 20 carbon atoms, alkenyl group having 1 to 20 carbon atoms, alkynyl group having 1 to 20 carbon atoms, halogenated alkyl group having 1 to 20 carbon atoms, aryl group having 5 to 24 carbon atoms, 2 to 24 carbon atoms Heteroaryl group, C 1 to C 20 alkoxy group, C 5 to C 24 aryloxy group, C 1 to C 20 alkylsilyl group, C 5 to C 24 arylsilyl group, C 1 to C 20 alkylamine group and C atoms It means further substituted with one or more substituents selected from 6 to 24 arylamine groups.

In addition, the X ₁ to X ₂₀ , R ₁ to R ₇ , K, J ₁ to J ₂ and their substituents are each connected to each other or with adjacent substituents to form an alicyclic ring, a monocyclic or polycyclic aromatic ring or a hetero ring. Can be formed.

In addition, the range of carbon number of the alkyl group or aryl group in the'substituted or unsubstituted alkyl group having 1 to 60 carbon atoms' and'substituted or unsubstituted aryl group having 6 to 60 carbon atoms' consider 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.

On the other hand, the aryl group contained in the organic light-emitting compound according to the present invention is an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and 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, And aromatic groups such as pyrenyl 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 , 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, It may be substituted with a C2-C24 heteroaryl group or a C2-C24 heteroarylalkyl group.

Meanwhile, the heteroaryl group included in the organic light-emitting compound according to the present invention may be any one selected from the following [Structural Formula 1] to [Structural Formula 10].

[Structural Formula 1] [Structural Formula 2] [Structural Formula 3] [Structural Formula 4]

[Structural Formula 5] [Structural Formula 6] [Structural Formula 7]

[Structural Formula 8] [Structural Formula 9] [Structural Formula 10]

In the [Structural Formula 1] to [Structural Formula 10],

T ₁ to T ₁₂ are the same as or different from each other, and each independently, is selected from C (R ₄₁ ), C (R ₄₂ ) (R ₄₃ ), N, N (R ₄₄ ), O and S, and the R ₄₁ 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 carbon number of 5 to It is selected from an aryl group of 30 and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms having O, N, S or P as a hetero atom.

More preferably, R ₃ may be any one selected from the following [Structural Formula 11].

[Structural Formula 11]

In [Structural Formula 11],

X is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 2 to 20 alkynyl group, substituted or unsubstituted C 3 to C 30 cycloalkyl group, substituted or unsubstituted C 5 to C 30 cycloalkenyl group, substituted or unsubstituted C 1 to C 30 alkoxy group, substituted or unsubstituted A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl thioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkyl having 1 to 30 carbon atoms Selected from an amine group, a substituted or unsubstituted aryl group having 5 to carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms having O, N, S or P as a hetero atom, a cyano group, a nitro group, and a halogen group And 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.

Specific examples of the alkyl group as a substituent used in the present invention include methyl group, ethyl group, propyl group, isopropyl 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, etc., and at least one hydrogen atom of 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, referred to as "alkylsilyl group"), a substituted or unsubstituted amino group (-NH ₂ , -NH(R), -N(R')(R"), wherein R, R'and R" are each Independently, it is an alkyl group having 1 to 24 carbon atoms (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, a C 1 to C 24 alkyl group, a C 1 to 24 C Halogenated alkyl group, C2-C24 alkenyl group, C2-C24 alkynyl group, C1-C24 heteroalkyl group, C5-C24 aryl group, C6-C24 arylalkyl group, C3-C24 hetero It may be substituted with an aryl group or a heteroarylalkyl group having 3 to 24 carbon atoms.

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, diphenylvinylsilyl, methylcyclobutylsilyl, dimethyl Furylsilyl, etc. are mentioned.

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.

The organic light-emitting compound represented by [Chemical Formula 1-1] to [Chemical Formula 1-2] according to the present invention is not limited in its range in the following specific compounds, but more specifically, to [Chemical Formula 2] to [Chemical Formula 460] It may be one selected from among the displayed compounds.

[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]

[Chemical Formula 46] [Chemical Formula 47] [Chemical Formula 48] [Chemical Formula 49]

[Formula 50] [Formula 51] [Formula 52] [Formula 53]

[Formula 54] [Formula 55] [Formula 56] [Formula 57]

[Chemical Formula 58] [Chemical Formula 59] [Chemical Formula 60] [Chemical 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]

[Chemical Formula 78] [Chemical Formula 79] [Chemical Formula 80] [Chemical 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]

[Chemical Formula 118] [Chemical Formula 119] [Chemical Formula 120] [Chemical Formula 121]

[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]

[Chemical Formula 170] [Chemical Formula 171] [Chemical Formula 172] [Chemical 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]

[Chemical Formula 202] [Chemical Formula 203] [Chemical Formula 204] [Chemical 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 232] [Formula 233]

[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]

[Chemical Formula 250] [Chemical Formula 251] [Chemical Formula 252] [Chemical 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]

[Chemical Formula 270] [Chemical Formula 271] [Chemical Formula 272] [Chemical Formula 273]

[Formula 274] [Formula 275] [Formula 276] [Formula 277]

[Formula 278] [Formula 279] [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] [Formula 297]

[Formula 298] [Formula 299] [Formula 300] [Formula 301]

[Formula 302] [Formula 303] [Formula 304] [Formula 305]

[Formula 306] [Formula 307] [Formula 308] [Formula 309]

[Chemical Formula 310] [Chemical Formula 311] [Chemical Formula 312] [Chemical Formula 313]

[화학식 314] [화학식 315] [화학식 316] [화학식 317]

[Formula 314] [Formula 315] [Formula 316] [Formula 317]

[Formula 318] [Formula 319] [Formula 320] [Formula 321]

[Formula 322] [Formula 323] [Formula 324] [Formula 325]

[Formula 326] [Formula 327] [Formula 328] [Formula 329]

[Formula 330] [Formula 331] [Formula 332] [Formula 333]

[Formula 334] [Formula 335] [Formula 336] [Formula 337]

[Formula 338] [Formula 339] [Formula 340] [Formula 341]

[Formula 342] [Formula 343] [Formula 344] [Formula 345]

[Formula 346] [Formula 347] [Formula 348] [Formula 349]

[Chemical Formula 350] [Chemical Formula 351] [Chemical Formula 352] [Chemical Formula 353]

[Formula 354] [Formula 355] [Formula 356] [Formula 357]

[Formula 358] [Formula 359] [Formula 360] [Formula 361]

[Formula 362] [Formula 363] [Formula 364] [Formula 365]

[Formula 366] [Formula 367] [Formula 368] [Formula 369]

[Formula 370] [Formula 371] [Formula 372] [Formula 373]

[Chemical Formula 374] [Chemical Formula 375] [Chemical Formula 376] [Chemical Formula 377]

[Chemical Formula 378] [Chemical Formula 379] [Chemical Formula 380] [Chemical Formula 381]

[Chemical Formula 382] [Chemical Formula 383] [Chemical Formula 384] [Chemical Formula 385]

[Chemical Formula 386] [Chemical Formula 387] [Chemical Formula 388] [Chemical Formula 389]

[Formula 390] [Formula 391] [Formula 392] [Formula 393]

[Chemical Formula 394] [Chemical Formula 395] [Chemical Formula 396] [Chemical Formula 397]

[Chemical Formula 398] [Chemical Formula 399] [Chemical Formula 400] [Chemical Formula 401]

[Formula 402] [Formula 403] [Formula 404] [Formula 405]

[Formula 406] [Formula 407] [Formula 408] [Formula 409]

[Formula 410] [Formula 411] [Formula 412] [Formula 413]

[Formula 414] [Formula 415] [Formula 416] [Formula 417]

[Formula 418] [Formula 419] [Formula 420] [Formula 421]

[Formula 422] [Formula 423] [Formula 424] [Formula 425]

[Formula 426] [Formula 427] [Formula 428] [Formula 429]

[Formula 430] [Formula 431] [Formula 432] [Formula 433]

[Formula 434] [Formula 435] [Formula 436] [Formula 437]

[Formula 438] [Formula 439] [Formula 440] [Formula 441]

[Formula 442] [Formula 443] [Formula 444] [Formula 445]

[Formula 446] [Formula 447] [Formula 448] [Formula 449]

[Chemical Formula 450] [Chemical Formula 451] [Chemical Formula 452] [Chemical Formula 453]

[Formula 454] [Formula 455] [Formula 456] [Formula 457]

[Formula 458] [Formula 459] [Formula 460]

Another aspect of the present invention relates to an organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer is the [Formula 1] 1-1] to [Formula 1-2] characterized in that it comprises at least one organic light-emitting compound.

In addition, the organic layer is made of one or a plurality of organic layers including a light emitting layer, and the organic layer further includes at least one layer selected from a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.

According to a preferred embodiment of the present invention, the organic light emitting compound represented by [Chemical Formula 1-1] to [Chemical Formula 1-2] according to the present invention is characterized in that it is contained in the hole transport layer or the hole injection layer.

In addition, while using the organic light-emitting compound according to the present invention in the hole transport layer, in order to implement more excellent luminous efficiency and long life characteristics, the light-emitting layer may contain one or more host compounds and one or more dopant compounds, respectively, and blue, red, or White light may be emitted by including one or more organic emission layers emitting green light.

In addition, according to a preferred embodiment of the present invention, the emission layer may further include at least one dopant compound, and the dopant compound may be an amine compound represented by the following [Formula I].

[Chemical Formula Ⅰ]

In the above [Formula I],

A is selected from a substituted or unsubstituted aryl group having 5 to 50 carbon atoms and a heteroaryl group having 3 to 50 carbon atoms having O, N or S as a substituted or unsubstituted hetero atom, and X ₁ to X ₂ are the same as each other or And each independently a single bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, X ₁ and X ₂ may be bonded to each other, and Y ₁ to Y ₂ are the same or different from each other, and each independently A substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted C1-C24 Heteroalkyl group, substituted or unsubstituted C3-C24 cycloalkyl group, substituted or unsubstituted C1-C24 alkoxy group, cyano group, halogen group, substituted or unsubstituted C6-C24 aryloxy group, substituted Or an unsubstituted C1 to C40 alkylsilyl group, a substituted or unsubstituted C6 to C30 arylsilyl group, germanium, phosphorus, boron, deuterium and hydrogen, and Y ₁ to Y ₂ are each adjacent to each other Combined with a substituent, an aliphatic, aromatic, aliphatic hetero or aromatic hetero condensed ring may be formed.

In addition, the dopant compound may be an amine compound represented by the following [Chemical Formula II].

[Chemical Formula Ⅱ]

In the above [Formula II],

C _y is a substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms, b is an integer of 1 to 4, but when b is 2 or more, each is the same as or different from each other, and may be in a fused form, and hydrogen substituted thereto May each be substituted with deuterium or alkyl, B is a single bond or -[C(R ₅ )(R ₆ )] _p -, wherein p is an integer of 1 to 3, but when p is 2 or more, 2 or more R ₅ and R ₆ are the same as or different from each other, and R ₁ to R ₆ are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group A salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkyne having 2 to 60 carbon atoms Nyl group, substituted or unsubstituted C1-C60 alkoxy group, substituted or unsubstituted C1-C60 alkylthio group, substituted or unsubstituted C3-C60 cycloalkyl group, substituted or unsubstituted C6-C6 60 aryl group, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, substituted or unsubstituted A substituted (alkyl) amino group having 1 to 60 carbon atoms, a di (substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, or a (substituted or unsubstituted aryl having 6 to 60 carbon atoms) amino group, di (substituted or unsubstituted Aryl) amino group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus and boron, and a is 1 Is an integer of 4, but when a is 2 or more, 2 or more R ₃ are the same as or different from each other, and R ₃ In the case of a plurality of these, each R ₃ may be in a fused form.

According to a preferred embodiment, A is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and may be selected from compounds represented by the following [Chemical Formula A1] to [Chemical Formula A10].

[Formula A1] [Formula A2] [Formula A3] [Formula A4] [Formula A5]

[Formula A6] [Formula A7] [Formula A8] [Formula A9] [Formula A10]

In the above [Formula A3],

Z ₁ to Z ₂ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted carbon number 2 to 60 alkynyl group, substituted or unsubstituted C 1 to C 60 alkoxy group, substituted or unsubstituted C 1 to C 60 alkylthio group, substituted or unsubstituted C 3 to C 60 cycloalkyl group, substituted or unsubstituted A substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted arylheoxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, and a substituted or unsubstituted C2-C60 hetero An aryl group, a substituted or unsubstituted (alkyl) amino group having 1 to 60 carbon atoms, a di(substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, and a (substituted or unsubstituted aryl having 6 to 60 carbon atoms) amino group, It is selected from di(substituted or unsubstituted aryl) amino groups having 6 to 60 carbon atoms, and may be bonded to adjacent groups to form a condensed ring.

In addition, the amine group bonded to A may be any one selected from the group represented by the following [substituent 1] to [substituent 52].

[Substituent 1] [Substituent 2] [Substituent 3] [Substituent 4]

[Substituent 5] [Substituent 6] [Substituent 7] [Substituent 8]

[Substituent 9] [Substituent 10] [Substituent 11] [Substituent 12]

[Substituent 13] [Substituent 14] [Substituent 15] [Substituent 16]

[Substituent 17] [Substituent 18] [Substituent 19] [Substituent 20]

[Substituent 21] [Substituent 22] [Substituent 23] [Substituent 24]

[Substituent 25] [Substituent 26]

[Substituent 27] [Substituent 28] [Substituent 29] [Substituent 30]

[Substituent 31] [Substituent 32] [Substituent 33] [Substituent 34]

[Substituent 35] [Substituent 36] [Substituent 37] [Substituent 38]

[Substituent 39] [Substituent 40] [Substituent 41] [Substituent 42]

[Substituent 43] [Substituent 44] [Substituent 45] [Substituent 46]

[Substituent 47] [Substituent 48] [Substituent 49] [Substituent 50]

[Substituent 51] [Substituent 52]

In the above [substituent 1] to [substituent 52],

Each R is independently hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, substitution Or an unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, A substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C5-C60 Aryloxy group, substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, substituted or unsubstituted (alkyl) amino group having 1 to 60 carbon atoms, di(substituted Or unsubstituted C1-C60 alkyl) amino group, or (substituted or unsubstituted C6-C60 aryl) amino group, di(substituted or unsubstituted C6-C60 aryl) amino group, substituted or unsubstituted At least one selected from an alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron, and may be connected to adjacent substituents to form a condensed ring.

In addition, according to a preferred embodiment of the present invention, the light emitting layer is characterized in that it further comprises at least one host compound, the host compound may be a compound represented by the following [Formula 1A] to [Formula 1D] .

[Formula 1A]

[Formula 1B]

[Formula 1C]

[Formula 1D]

In the above [Formula 1A], X ₁ to X ₁₀ are the same as or different from each other, and each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alke having 2 to 30 carbon atoms Nyl group, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted C 6 to carbon number 30 aryloxy group, substituted or unsubstituted C 1 to C 30 alkyl thioxy group, substituted or unsubstituted C 5 to C 30 arylthioxy group, substituted or unsubstituted C 1 to C 30 alkylamine group, substituted or Unsubstituted C5 to C30 arylamine group, substituted or unsubstituted C5 to C50 aryl group, substituted or unsubstituted and C3 to C50 heteroaryl group having O, N or S as a hetero atom, substituted or It is selected from an unsubstituted silicone group, a substituted or unsubstituted boron group, a substituted or unsubstituted silane group, a carbonyl group, a phosphoryl group, an amino group, a nitrile group, a hydroxy group, a nitro group, a halogen group, an amide group, and an ester group.

In addition, each of X ₁ to X ₁₀ may form a condensed ring of a group adjacent to each other and an aliphatic, aromatic, aliphatic hetero or aromatic hetero.

In the above [Formula 1B], Ar ₁₇ to Ar ₂₀ are the same as or different from each other and are each independently selected from a substituted or unsubstituted aromatic linking group having 5 to 60 carbon atoms and a substituted or unsubstituted heteroaromatic linking group having 2 to 60 carbon atoms .

In addition, R ₆₀ to R ₆₃ are the same as or different from each other, and each independently hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid A group or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, substituted or unsubstituted A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, A substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, -Si (R ₂₁ ) (R ₂₂ ) (R ₂₃ ) and -N (R ₂₄ ) ( R ₂₅ ) is selected from.

In addition, the R ₂₁ to R ₂₅ are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted carbon number of 2 to 60 alkynyl group, substituted or unsubstituted C1-C60 alkoxy group, substituted or unsubstituted C3-C60 cycloalkyl group, substituted or unsubstituted C5-C60 aryl group, substituted or unsubstituted 5 It is selected from aryloxy group of to 60, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In addition, w and ww are the same as or different from each other, x and xx are the same as or different from each other, and w+ww and x+xx values are the same or different from each other, and are each independently an integer of 0 to 3.

In addition, y and yy are the same as or different from each other, z and zz are the same or different from each other, y+yy to z+zz values are 2 or less, and are integers of 0 to 2, respectively.

In [Chemical Formula 1C], Ar ₂₁ to Ar ₂₄ are the same as or different from each other and are each independently selected from a substituted or unsubstituted aromatic linking group having 5 to 60 carbon atoms and a substituted or unsubstituted heteroaromatic linking group having 2 to 60 carbon atoms .

In addition, R ₆₄ to R ₆₇ are the same as or different from each other, and each independently hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid A group or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, substituted or unsubstituted A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, A substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, -Si (R ₂₁ ) (R ₂₂ ) (R ₂₃ ) and -N (R ₂₄ ) ( R ₂₅ ) is selected from.

In addition, the R ₂₁ to R ₂₅ are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted carbon number of 2 to 60 alkynyl group, substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, substituted or unsubstituted aryl group having 5 to 60 carbon atoms, substituted or unsubstituted carbon number It is selected from a 5 to 60 aryloxy group, a substituted or unsubstituted C 5 to C 60 arylthio group, and a substituted or unsubstituted C 2 to C 60 heteroaryl group.

In addition, ee to hh are the same as or different from each other, and each independently an integer of 1 to 4, and ii to ll are the same or different from each other, and each independently an integer of 0 to 4.

In the above [Formula 1D], Ar ₂₅ to Ar ₂₇ are the same as or different from each other and are each independently selected from a substituted or unsubstituted aromatic linking group having 5 to 60 carbon atoms and a substituted or unsubstituted heteroaromatic linking group having 2 to 60 carbon atoms .

In addition, R ₆₈ to R ₇₃ are the same as or different from each other, and each independently hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid A group or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, substituted or unsubstituted A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 5 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, A substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, -Si (R ₂₁ ) (R ₂₂ ) (R ₂₃ ) and -N (R ₂₄ ) ( R ₂₅ ) is selected from.

In addition, the R ₂₁ to R ₂₅ are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted carbon number of 2 to 60 alkynyl group, substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, substituted or unsubstituted aryl group having 5 to 60 carbon atoms, substituted or unsubstituted carbon number It is selected from a 5 to 60 aryloxy group, a substituted or unsubstituted C 5 to C 60 arylthio group, and a substituted or unsubstituted C 2 to C 60 heteroaryl group.

In addition, each of R ₂₁ to R ₂₅ may be connected to an adjacent substituent to form a saturated or unsaturated cyclic structure.

Further, mm to ss are the same as or different from each other, and are each independently an integer of 0 to 4.

According to a preferred embodiment, the [Chemical Formula 1A] may be selected from compounds represented by the following [Chemical Formula 1Aa] to [Chemical Formula 1Ae].

[Formula 1Aa]

[Formula 1Ab]

[Formula 1Ac]

[Formula 1Ad]

[Formula 1Ae]

In the [Formula 1Aa], Ar ₇ and Ar ₈ are the same as or different from each other and are each independently selected from a substituted or unsubstituted aromatic linking group having 5 to 60 carbon atoms and a substituted or unsubstituted heteroaromatic linking group having 2 to 60 carbon atoms .

Also, R ₂₁ To R ₃₀ are the same as or different from each other, each independently the same as the definition in X ₁ to X ₁₀ , e and f are the same as or different from each other, and each independently an integer of 0 to 4.

In the [Chemical Formula 1Ab], Ar ₉ and Ar ₁₀ are the same as or different from each other and are each independently the same as the definition in Ar ₇ to Ar ₈ , and R ₃₁ to R ₄₀ are the same or different from each other, and each independently the X _{It is the} same as the definition in ₁ to X ₁₀ , g and h are the same as or different from each other and are each independently an integer of 0 to 4, and each of the substituents may be linked to an adjacent substituent to form a saturated or unsaturated cyclic structure. However, in [Chemical Formula 1Ab], there is no case where an independent substituent is bonded to each of the 9-positions and 10-positions of the central anthracene so that the symmetrical group is bonded to the anthracene phase.

In the [Chemical Formula 1Ac], Ar ₁₁ to Ar ₁₂ are the same as or different from each other and are each independently the same as the definition in Ar ₇ to Ar ₈ , i and j are the same or different from each other, and each independently an integer of 1 to 4 to be.

In addition, one of the substituents c1 to c4 is bonded to the * moiety of the formula Ac, and X is selected from -O-, -S-, -N(R ₅₀ )- and -N(R ₅₁ R ₅₂ ), and R41 To R49 are the same as or different from each other, and each independently the same as defined in X ₁ to X ₁₀ , k is an integer of 1 to 4, and when k is 2 or more, the two or more R ₄₂ to R ₄₉ are the same as each other or Different.

In the [Chemical Formula 1Ad], Ar ₁₃ and Ar ₁₄ are the same as or different from each other and are each independently the same as the definition in Ar ₇ to Ar ₈ , R ₅₃ and R ₅₄ are the same as the definition in X ₁ to X ₁₀ , and , L and m are the same as or different from each other, and each independently an integer of 1 to 4, and P and q are the same or different from each other, and each independently an integer of 0 to 4.

In the above [Formula 1Ae], L2 is a single bond, -O-, -S-, -N(R55)-, an alkylene group or an arylene group, and r is 2 or 3, in which case each of the [] They can be the same or different, and the * parts are connected to each other.

In addition, Ar ₁₅ and Ar ₁₆ are the same as or different from each other and are each independently the same as defined in Ar ₇ to Ar ₈ , and R ₅₆ to R ₅₉ are the same or different from each other, and each independently defined in X ₁ to X ₁₀ Is the same as, u is an integer of 1 to 4, v is an integer of 1 to 3, s and t are the same as or different from each other and are each independently an integer of 0 to 4, wherein s, t, u, v are When two or more are each independently, Ar ₁₅ and Ar ₁₆ and R ₅₆ to R ₅₉ may be the same or different from each other.

According to a more preferred embodiment, [Formula 1A] to [Formula 1D] may be any one selected from the following [Compound 1] to [Compound 310].

In addition, the electron transport layer used in the organic light emitting device according to the present invention smoothly transports electrons supplied from the cathode to the organic light emitting layer and inhibits the movement of holes that could not be combined in the organic light emitting layer, thereby recombining in the light emitting layer. It serves to increase.

3,3-(3,8-di(biphenyl-4yl)pyrene-1,6-diyl)dipyridine was used as the material for the electron transport layer, but it is not particularly limited and may be used as long as it is commonly used in the art. Of course, for example, the oxadiazole derivatives PBD, BMD, BND or Alq ₃ may be used.

On the other hand, on the top of the electron transport layer, an electron injecting layer (EIL) that facilitates electron injection from the cathode and ultimately improves power efficiency may be further stacked. The material of the electron injection layer Also, as long as it is commonly used in the art, it may be used without particular limitation, and for example, materials such as LiF, NaCl, CsF, Li ₂ O, and BaO may be used.

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 light emitting layer 50, an electron transport layer 60, and a cathode. Including 80, may further include a hole injection layer 30 and an electron injection layer 70 if necessary, it is also possible to further form an intermediate layer of one or two layers, and hole blocking layer Alternatively, 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 typical 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.

A hole injection layer 30 is formed on the anode 20 electrode, and a hole transport layer 40 is formed on the hole injection layer 30. The hole injection layer or the hole transport layer is formed by vacuum thermal evaporation or spin coating of the organic light-emitting compound according to the present invention.

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 such a 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.

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, according to another embodiment of the present invention, 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 is a monomolecular deposition method or a solution process. The organic light emitting diode according to the present invention may be used in a display device, a display device, and a single color or white lighting device.

Hereinafter, the present invention will be described in more detail by examples. However, the following examples are presented as examples, and the present invention is not limited thereto.

<Example 1> Synthesis of the compound represented by [Chemical Formula 5]

(1) Synthesis of a compound represented by [Formula 1-a]

A compound represented by [Chemical Formula 1-a] was synthesized by the following [Scheme 1].

[Scheme 1]

[Formula 1-a]

To dibenzothiophene 50 g (271 mmol), tetrahydrofuran 400 mL was added and stirred at -78 °C. After 30 minutes, 178 mL (285 mmol) of normal butyllithium was slowly added dropwise, and then 69 g (271 mmol) of iodine was slowly added dropwise after 1 hour, and the temperature was raised to room temperature. After stirring for 24 hours, an aqueous sodium thiosulfate solution was added. After concentration under reduced pressure, it was recrystallized with hexane to obtain 52 g of a compound represented by [Chemical Formula 1-a]. (Yield 60%)

(2) Synthesis of a compound represented by [Formula 1-b]

A compound represented by [Chemical Formula 1-b] was synthesized by the following [Scheme 2].

[Scheme 2]

[Formula 1-a] [Formula 1-b]

[Formula 1-a] obtained from [Scheme 1] 52 g (168 mmol), copper iodide 6.5 g (34 mmol), trans-4-hydroxy-L-proline 8.9 g (68 mmol), calcium carbonate 69.6 g (504 mmol), 260 mL of dimethylsulfoxide was added, and 167.9 g of 28% aqueous ammonia was slowly added thereto. Stir at 100° C. for 12 hours. When the reaction was completed, it was cooled to room temperature, concentrated under reduced pressure, and separated by column chromatography to obtain 10 g of a compound represented by [Chemical Formula 1-b]. (Yield 30%)

(3) Synthesis of a compound represented by [Formula 1-c]

A compound represented by [Chemical Formula 1-c] was synthesized by the following [Scheme 3].

[Scheme 3]

[Formula 1-b] [Formula 1-c]

Add 10 g (50 mmol) of the compound represented by [Chemical Formula 1-b] obtained from [Scheme 2] and 100 mL of hydrochloric acid, and adjust to 5°C. Mix sodium nitrite 3.45 g (50 mmol) and 20 mL of water, and add it slowly. After holding for 2 hours at 5 ℃, a solution of 56.6 g (251 mmol) of tin (II) chloride dihydrate and 200 mL of hydrochloric acid was slowly added. After holding at room temperature for 3 hours, it was filtered to obtain 8 g of a compound represented by [Chemical Formula 1-c]. (Yield 63%)

(4) Synthesis of a compound represented by [Formula 1-d]

A compound represented by [Chemical Formula 1-d] was synthesized by the following [Scheme 4].

[Scheme 4]

[Formula 1-c] [Formula 1-d]

3,3-dimethyl-2,3-dihydro-1H-inden-1-one 4.26 g (27 mmol), 8 g (32 mmol) of the compound represented by [Chemical Formula 1-c] obtained from [Scheme 3] ), add 43 mL of acetic acid and 2.13 mL of hydrochloric acid, and stir under reflux for 12 hours. Concentrated under reduced pressure and separated by column chromatography to obtain 4.9 g of a compound represented by [Chemical Formula 1-d]. (Yield 54%)

(5) Synthesis of a compound represented by [Formula 1-e]

A compound represented by [Chemical Formula 1-e] was synthesized by the following [Scheme 5].

[Scheme 5]

[Formula 1-d] [Formula 1-e]

Compound 7 g (21 mmol) represented by [Formula 1-d] obtained from [Scheme 4], iodobenzene 8.41 g (31 m mol), copper powder 3.93 g (62 mmol), 18-crown-6- Ether 1.09 g (4 mmol), potassium carbonate 14.25 g (103 mmol), and dichlorobenzene were added and stirred under reflux for 24 hours. After completion of the reaction, dichlorobenzene was removed and separated by column chromatography to obtain 6.8 g of a compound represented by [Chemical Formula 1-e]. (79% yield)

(6) Synthesis of a compound represented by [Formula 1-f]

A compound represented by [Chemical Formula 1-f] was synthesized by the following [Scheme 6].

[Scheme 6]

[Formula 1-e] [Formula 1-f]

10 g (24 mmol) of the compound represented by [Chemical Formula 1-e] obtained from [Scheme 5], dissolved in 70 mL of dimethylformamide, and stirred at 0°C. 4.24 g (21 mmol) of N-bromosuccinimide is slowly added. After raising to room temperature, it was stirred for 4 hours. After completion of the reaction, H ₂ O was added dropwise at room temperature, and when brown crystals were formed, filtered and recrystallized with toluene and methanol to obtain 8.3 g of a compound represented by [Formula 1-f]. (Yield 70%)

(7) Synthesis of a compound represented by [Formula 1-g]

A compound represented by [Chemical Formula 1-g] was synthesized by the following [Scheme 7].

[Scheme 7]

[Formula 1-g]

Dissolve 40 g (236 mmol) of diphenylamine in 400 mL of dimethylformamide in a 1 L reactor, and stir at 0°C. 82 g (461 mmol) of N-bromosuccinimide is slowly added. After raising to room temperature, it was stirred for 4 hours. After the reaction was completed, H ₂ O was added dropwise at room temperature, and when brown crystals were formed, filtered and recrystallized with toluene and methanol to obtain 40 g of a compound represented by [Chemical Formula 1-g]. (Yield 60%)

(8) Synthesis of a compound represented by [Formula 1-h]

A compound represented by [Chemical Formula 1-h] was synthesized by the following [Scheme 8].

[Scheme 8]

[Formula 1-g] [Formula 1-h]

Compound 12 g (37 mmol) represented by [Chemical Formula 1-g] obtained from [Scheme 7], phenyl boronic acid 10 g (81 mmol), potassium carbonate 15.2 g (11 mmol), tetrakistriphenylphosphine palladium 1.7 g (1 mmol), H ₂ O 40 mL, toluene 100 mL, and 1,4-dioxane 100 mL were added and stirred under reflux for 24 hours. After concentration under reduced pressure, it was recrystallized with toluene and methanol to obtain 7.9 g of a compound represented by [Chemical Formula 1-h]. (Yield 65%)

(9) Synthesis of a compound represented by [Formula 1-i]

A compound represented by [Chemical Formula 1-i] was synthesized by the following [Scheme 9].

[Scheme 9]

[Formula 1-h] [Formula 1-i]

7.9 g (24.6 mmol) of the compound represented by [Chemical Formula 1-h] obtained from [Scheme 8], 8.3 g (30 mmol) of 4-bromo iodobenzene, 0.4 g (0.3 mmol) of palladium acetate, sodium tertiary 4.2 g (43 mmol) of butoxide, 0.1 g (0.3 mmol) of triturateylphosphine, and 100 ml of toluene were added and stirred under reflux for 13 hours. After concentration under reduced pressure, separation was performed by column chromatography, and recrystallized with methylene chloride and methanol to obtain 4.0 g of a compound represented by [Chemical Formula 1-i]. (Yield 45%)

(10) Synthesis of a compound represented by [Formula 1-j]

A compound represented by [Chemical Formula 1-j] was synthesized by the following [Scheme 10].

[Scheme 10]

[Formula 1-i] [Formula 1-j]

125 g (262.4 mmol) of the compound represented by [Chemical Formula 1-i] obtained from [Scheme 9], 78 g of bispinacolatodiboron, (314.8 mmol), palladium chloride-1,1'-bis(diphenylphos) Pinot) ferrocene 7.5 g (9 mmol), potassium acetate 72.2 g (524.9 mmol), and toluene 1250 mL were added and stirred under reflux for 10 hours. Concentrated under reduced pressure and separated by column chromatography to obtain 102 g of a compound represented by [Chemical Formula 1-j]. (Yield 83%)

(11) Synthesis of the compound represented by [Chemical Formula 5]

A compound represented by [Chemical Formula 5] was synthesized by the following [Scheme 11].

[Scheme 11]

[Formula 1-f] [Formula 1-j] [Formula 5]

Compound 7 g (13 mmol) represented by [Formula 1-f] obtained from [Scheme 6], 11.12 g (21 mmol) compound represented by [Formula 1-j] obtained from [Scheme 10], potassium carbonate 3.9 g (28 mmol), tetrakistriphenylphosphine palladium 0.3g (0.6 mmol), H ₂ O 14 mL, toluene 35 mL and 1,4-dioxane 35 mL were added and stirred under reflux for 24 hours. Concentrated under reduced pressure, and separated by column chromatography to obtain 3.6 g of a compound represented by [Chemical Formula 5]. (Yield 31%)

MS [M] ⁺ : 812

<Example 2> Synthesis of the compound represented by [Chemical Formula 7]

(1) Synthesis of a compound represented by [Formula 2-a]

A compound represented by [Chemical Formula 2-a] was synthesized by the following [Scheme 12].

[Scheme 12]

[Formula 2-a]

Biphenyl-4-amine 50.0 g (330 mmol), 2-bromo-9,9-dimethyl-9H-fluorene 43.2 g (276 mmol), palladium acetate 1.2 g (5.6 mmol), xantphos 6.4 g (11.02 mmol), 126 g (386 mmol) of cesium carbonate, and 1000 mL of toluene were added and stirred under reflux for 24 hours. After completion of the reaction, the mixture was cooled to room temperature, concentrated under reduced pressure, and separated by column chromatography to obtain 57 g of a compound represented by [Chemical Formula 2-a]. (Yield 91%)

(2) Synthesis of a compound represented by [Formula 2-b]

A compound represented by [Chemical Formula 2-b] was synthesized by the following [Scheme 13].

[Scheme 13]

[Formula 2-a] [Formula 2-b]

Except for using [Chemical Formula 2-a] instead of [Chemical Formula 1-h] used in [Scheme 9] of Example 1-9, it was synthesized in the same manner to obtain 47 g of a compound represented by [Chemical Formula 2-b] . (Yield 55%)

(3) Synthesis of a compound represented by [Formula 2-c]

A compound represented by [Chemical Formula 2-c] was synthesized by the following [Scheme 14].

[Scheme 14]

[Formula 2-b] [Formula 2-c]

Except for using [Chemical Formula 2-b] instead of [Chemical Formula 1-i] used in [Scheme 10] of Example 1-10, it was synthesized in the same manner to obtain 13 g of a compound represented by [Chemical Formula 2-c] . (Yield 71%)

(4) Synthesis of the compound represented by [Chemical Formula 7]

A compound represented by [Chemical Formula 7] was synthesized by the following [Scheme 15].

[Scheme 15]

[Formula 1-f] [Formula 2-c] [Formula 7]

Except for using [Chemical Formula 2-c] instead of [Chemical Formula 1-j] used in [Scheme 11] of Example 1-11, it was synthesized in the same manner to obtain 3.7 g of a compound represented by [Chemical Formula 7]. (Yield 29%)

MS [M] ⁺ : 852

<Example 3> Synthesis of the compound represented by [Chemical Formula 41]

(1) Synthesis of a compound represented by [Chemical Formula 3-a]

A compound represented by [Chemical Formula 3-a] was synthesized by the following [Scheme 16].

[Scheme 16]

[Formula 3-a]

Except for using dibenzofuran instead of dibenzothiophene used in [Scheme 1] of Example 1-1, it was synthesized in the same manner to obtain 52 g of a compound represented by [Chemical Formula 3-a]. (Yield 60%)

(2) Synthesis of a compound represented by [Chemical Formula 3-b]

A compound represented by [Chemical Formula 3-b] was synthesized by the following [Scheme 17].

[Scheme 17]

[Formula 3-a] [Formula 3-b]

Except for using [Chemical Formula 3-a] instead of [Chemical Formula 1-a] used in [Scheme 2] of Example 1-2, it was synthesized by the same method to obtain 9 g of a compound represented by [Chemical Formula 3-b] . (Yield 30%)

(3) Synthesis of a compound represented by [Formula 3-c]

A compound represented by [Chemical Formula 3-c] was synthesized by the following [Scheme 18].

[Scheme 18]

[Formula 3-b] [Formula 3-c]

Except for using [Chemical Formula 3-b] instead of [Chemical Formula 1-b] used in [Scheme 3] of Example 1-3, it was synthesized in the same manner to obtain 7 g of a compound represented by [Chemical Formula 3-c] . (Yield 63%)

(4) Synthesis of a compound represented by [Chemical Formula 3-d]

A compound represented by [Chemical Formula 3-d] was synthesized by the following [Scheme 19].

[Scheme 19]

[Formula 3-c] [Formula 3-d]

Except for using [Chemical Formula 3-c] instead of [Chemical Formula 1-c] used in [Scheme 4] of Example 1-4, it was synthesized in the same manner to obtain 4.8 g of a compound represented by [Chemical Formula 3-d] . (Yield 54%)

(5) Synthesis of a compound represented by [Formula 3-e]

A compound represented by [Chemical Formula 3-e] was synthesized by the following [Scheme 20].

[Scheme 20]

[Formula 3-d] [Formula 3-e]

Except for using [Chemical Formula 3-d] instead of [Chemical Formula 1-d] used in [Scheme 5] of Example 1-5, it was synthesized in the same manner to obtain 63 g of a compound represented by [Chemical Formula 3-e] . (Yield 60%)

(6) Synthesis of a compound represented by [Chemical Formula 3-f]

A compound represented by [Chemical Formula 3-f] was synthesized by the following [Scheme 21].

[Scheme 21]

[Formula 3-e] [Formula 3-f]

Except for using [Chemical Formula 3-e] instead of [Chemical Formula 1-d] used in [Scheme 5] of Example 1-5, it was synthesized in the same manner to obtain 11 g of a compound represented by [Chemical Formula 3-f] . (Yield 60%)

(6) Synthesis of the compound represented by [Formula 41]

A compound represented by [Chemical Formula 41] was synthesized by the following [Scheme 22].

[Scheme 22]

[Formula 3-f] [Formula 1-j] [Formula 41]

Except for using [Chemical Formula 3-f] instead of [Chemical Formula 1-f] used in [Scheme 11] of Example 1-11, it was synthesized in the same manner to obtain 3.2 g of a compound represented by [Chemical Formula 41]. (Yield 25%)

MS [M] ⁺ : 795

<Example 4> Synthesis of the compound represented by [Chemical Formula 49]

(1) Synthesis of a compound represented by [Formula 4-a]

A compound represented by [Chemical Formula 4-a] was synthesized by the following [Scheme 23].

[Scheme 23]

[Formula 4-a]

Add 40 mL of dichloromethane and 50 mL (50 mmol) of 1M titanium tetrachloride dissolved in dichloromethane, and stir at -40 °C. Slowly add 35.5 mL (71.1 mmol) of 2 M dimethyl zinc dissolved in toluene, and stir at -40 °C for 20 minutes. 6-bromo-2,3-dihydro-1H-inden-1-one 5 g (23.7 mmol) and 40 mL of dichloromethane were added, slowly added dropwise, and stirred at room temperature overnight. The reaction was stopped with 10 ml of methanol, concentrated under reduced pressure, and separated by column chromatography to obtain 3.3 g of a compound represented by [Chemical Formula 4-a]. (Yield 62%)

(2) Synthesis of a compound represented by [Formula 4-b]

A compound represented by [Chemical Formula 4-b] was synthesized by the following [Scheme 24].

[Scheme 24]

[Formula 4-a] [Formula 4-b]

Compound 4 g (17.8 mmol) represented by [Chemical Formula 4-a] obtained from [Scheme 23], chromium oxide 280 mg (1.8 mmol), and dichloromethane 40 mL were added, and tertiary-butyl hydroxide 19 mL (190 mmol) was slowly added dropwise and stirred at room temperature overnight. After concentration under reduced pressure, it was separated by column chromatography to obtain 2.9 g of a compound represented by [Chemical Formula 4-b]. (Yield 68%)

(3) Synthesis of a compound represented by [Formula 4-c]

A compound represented by [Chemical Formula 4-c] was synthesized by the following [Scheme 25].

[Scheme 25]

[Formula 4-b] [Formula 4-c]

Synthesis by the same method except that [Formula 4-b] was used instead of 3,3-dimethyl-2,3-dihydro-1H-inden-1-one used in [Scheme 4] of Example 1-4 Thus, 12.3 g of a compound represented by [Chemical Formula 4-c] was obtained. (Yield 68%)

(4) Synthesis of a compound represented by [Formula 4-d]

A compound represented by [Chemical Formula 4-d] was synthesized by the following [Scheme 26].

[Scheme 26]

[Formula 4-c] [Formula 4-d]

Except for using [Chemical Formula 4-c] instead of [Chemical Formula 1-d] used in [Scheme 5] of Example 1-5, it was synthesized in the same manner to obtain 13 g of a compound represented by [Chemical Formula 4-d] . (Yield 66%)

(5) Synthesis of the compound represented by [Chemical Formula 49]

A compound represented by [Chemical Formula 49] was synthesized by the following [Scheme 27].

[Scheme 27]

[Formula 4-d] [Formula 49]

Except for using [Chemical Formula 4-d] instead of [Chemical Formula 1-f] used in [Scheme 11] of Example 1-11, it was synthesized in the same manner to obtain 4.3 g of a compound represented by [Chemical Formula 49]. (Yield 36%)

MS [M] ⁺ : 812

<Example 5> Synthesis of a compound represented by [Chemical Formula 99]

(1) Synthesis of the compound represented by [Formula 5-a]

A compound represented by [Chemical Formula 5-a] was synthesized by the following [Scheme 28].

[Scheme 28]

[Formula 3-c] [Formula 4-b] [Formula 5-a]

[Chemical Formula 1-c], 3,3-dimethyl-2,3-dihydro-1H-inden-1-one used in [Scheme 4] of Example 1-4 [Chemical Formula 3-c], [Chemical Formula Except for using 4-b], it was synthesized in the same manner to obtain 9.6 g of a compound represented by [Chemical Formula 5-a]. (Yield 54%)

(2) Synthesis of the compound represented by [Chemical Formula 5-b]

A compound represented by [Chemical Formula 5-b] was synthesized by the following [Scheme 29].

[Scheme 29]

[Formula 5-a] [Formula 5-b]

Except for using [Chemical Formula 5-a] instead of [Chemical Formula 1-d] used in [Scheme 5] of Example 1-5, it was synthesized in the same manner to obtain 17 g of a compound represented by [Chemical Formula 5-b] . (Yield 72%)

(3) Synthesis of a compound represented by [Chemical Formula 99]

A compound represented by [Chemical Formula 99] was synthesized by the following [Scheme 30].

[Scheme 30]

[Formula 5-b] [Formula 99]

Except for using [Chemical Formula 1-f] and [Chemical Formula 1-j] used in [Scheme 11] of Example 1-11, except for using [Chemical Formula 5-b] and [Chemical Formula 2-c], 3.1 g of a compound represented by [Chemical Formula 99] was obtained. (Yield 34%)

MS [M] ⁺ : 836

<Example 6> Synthesis of a compound represented by [Chemical Formula 147]

(1) Synthesis of a compound represented by [Formula 6-a]

A compound represented by [Chemical Formula 6-a] was synthesized by the following [Scheme 31].

[Scheme 31]

[Formula 6-a]

30 g (163 mmol) of dibenzothiophene and 300 mL of acetic acid were stirred. At 0 ℃ bromine 94.7 g (593 mmol) was slowly added. After complete dropwise addition, the mixture was stirred overnight at 50° C., and when crystals were formed, it was filtered to obtain 32 g of a compound represented by [Formula 6-a]. (Yield 75%)

(2) Synthesis of a compound represented by [Formula 6-b]

A compound represented by [Chemical Formula 6-b] was synthesized by the following [Scheme 32].

[Scheme 32]

[Formula 6-a] [Formula 6-b]

Except for using [Formula 6-a] instead of [Formula 1-a] used in [Scheme 2] of Example 1-2, it was synthesized in the same manner to obtain 10 g of a compound represented by [Formula 6-b] . (Yield 30%)

(3) Synthesis of a compound represented by [Formula 6-c]

A compound represented by [Chemical Formula 6c] was synthesized by the following [Scheme 33].

[Scheme 33]

[Formula 6-b] [Formula 6-c]

Except for using [Chemical Formula 6-b] instead of [Chemical Formula 1-b] used in [Scheme 3] of Example 1-3, it was synthesized by the same method to obtain 8 g of a compound represented by [Chemical Formula 6-c] . (Yield 63%)

(4) Synthesis of the compound represented by [Formula 6-d]

A compound represented by [Chemical Formula 6-d] was synthesized by the following [Scheme 34].

[Scheme 34]

[Formula 6-c] [Formula 4-b] [Formula 6-d]

[Chemical Formula 1-c], 3,3-dimethyl-2,3-dihydro-1H-inden-1-one used in [Scheme 4] of Example 1-4 [Chemical Formula 6-c], [Chemical Formula Except for using 4-b], it was synthesized in the same manner to obtain 14.6 g of a compound represented by [Formula 6-d]. (Yield 59%)

(5) Synthesis of a compound represented by [Chemical Formula 6-e]

A compound represented by [Chemical Formula 6-e] was synthesized by the following [Scheme 35].

[Scheme 35]

[Formula 6-d] [Formula 6-e]

Except for using [Chemical Formula 6-d] instead of [Chemical Formula 1-d] used in [Scheme 5] of Example 1-5, 9.8 g of a compound represented by [Chemical Formula 6-e] was obtained . (Yield 52%)

(6) Synthesis of the compound represented by [Chemical Formula 147]

A compound represented by [Chemical Formula 147] was synthesized by the following [Scheme 36].

[Scheme 36]

[Formula 6-e] [Formula 147]

Except for using [Chemical Formula 1-f] and [Chemical Formula 1-j] used in [Scheme 11] of Example 1-11, except for using [Chemical Formula 6-e] and [Chemical Formula 2-c], 3.5 g of a compound represented by [Chemical Formula 147] was obtained. (Yield 29%)

MS [M] ⁺ : 852

<Example 7> Synthesis of a compound represented by [Chemical Formula 229]

(1) Synthesis of a compound represented by [Formula 7-a]

A compound represented by [Chemical Formula 7-a] was synthesized by the following [Scheme 37].

[Scheme 37]

[Formula 7-a]

Compound represented by [Chemical Formula 7-a] synthesized by the same method except that 3-bromo-9-phenylcarbazole was used instead of [Chemical Formula 1-a] used in [Scheme 2] of Example 1-2 40.8 g was obtained. (Yield 60%)

(2) Synthesis of a compound represented by [Formula 7-b]

A compound represented by [Chemical Formula 7-b] was synthesized by the following [Scheme 38].

[Scheme 38]

[Formula 7-a] [Formula 7-b]

Except for using [Chemical Formula 7-a] instead of [Chemical Formula 1-b] used in [Scheme 3] of Example 1-3, it was synthesized by the same method to obtain 9 g of a compound represented by [Chemical Formula 7-b] . (Yield 63%)

(3) Synthesis of a compound represented by [Formula 7-c]

A compound represented by [Chemical Formula 7-c] was synthesized by the following [Scheme 39].

[Scheme 39]

[Formula 7-b] [Formula 7-c]

Except for using [Chemical Formula 7-b] instead of [Chemical Formula 1-c] used in [Scheme 4] of Example 1-4, it was synthesized in the same manner to obtain 11.3 g of a compound represented by [Chemical Formula 7-c] . (Yield 33%)

(4) Synthesis of a compound represented by [Chemical Formula 229]

A compound represented by [Chemical Formula 229] was synthesized by the following [Scheme 40].

[Scheme 40]

[Formula 7-c] [Formula 229]

Except for using [Chemical Formula 7-c] instead of [Chemical Formula 1-f] used in [Scheme 11] of Example 1-11, it was synthesized in the same manner to obtain 4.3 g of a compound represented by [Chemical Formula 229]. (Yield 34%)

MS [M] ⁺ : 718

<Example 8> Synthesis of a compound represented by [Chemical Formula 258]

(1) Synthesis of a compound represented by [Formula 8-a]

A compound represented by [Chemical Formula 8-a] was synthesized by the following [Scheme 41].

[Scheme 41]

[Formula 3-c] [Formula 8-a]

[Formula 1-c] used in [Reaction Scheme 4] of Example 1-4 [Formula 3-c], 1, instead of 3,3-dimethyl-2,3-dihydro-1H-inden-1-one Except for using 1-dimethyl-1,3-dihydro-2H-inden-2-one, it was synthesized in the same manner to obtain 9.6 g of a compound represented by [Chemical Formula 8-a]. (61% yield)

(2) Synthesis of a compound represented by [Formula 8-b]

A compound represented by [Chemical Formula 8-b] was synthesized by the following [Scheme 42].

[Scheme 42]

[Formula 8-a] [Formula 8-b]

[Chemical Formula 1-d] used in [Scheme 5] of Example 1-5, instead of iodobenzene [Chemical Formula 8-a]. Except for using 3-iodopyridine, it was synthesized in the same manner to obtain 23 g of a compound represented by [Chemical Formula 8-b]. (Yield 75%)

(3) Synthesis of a compound represented by [Formula 8-c]

A compound represented by [Chemical Formula 8-c] was synthesized by the following [Scheme 43].

[Scheme 43]

[Formula 8-b] [Formula 8-c]

Except for using [Chemical Formula 8-b] instead of [Chemical Formula 1-d] used in [Scheme 5] of Example 1-5, it was synthesized in the same manner to obtain 20 g of a compound represented by [Chemical Formula 8-c] . (Yield 78%)

(4) Synthesis of a compound represented by [Formula 258]

A compound represented by [Chemical Formula 258] was synthesized by the following [Scheme 44].

[Scheme 44]

[Formula 8-c] [Formula 258]

Except for using [Chemical Formula 8-c] instead of [Chemical Formula 1-f] used in [Scheme 11] of Example 1-11, it was synthesized in the same manner to obtain 3.1 g of a compound represented by [Chemical Formula 258]. (Yield 33%)

MS [M] ⁺ : 795

<Example 9> Synthesis of the compound represented by [Chemical Formula 287]

(1) Synthesis of a compound represented by [Formula 9-a]

A compound represented by [Chemical Formula 9-a] was synthesized by the following [Scheme 45].

[Scheme 45]

[Formula 6-c] [Formula 9-a]

Except for using [Chemical Formula 1-c] used in [Scheme 4] of Example 1-4, and instead of using [Chemical Formula 6-c], 13.6 g of a compound represented by [Chemical Formula 9-a] was synthesized Got it. (Yield 31%)

(2) Synthesis of a compound represented by [Chemical Formula 287]

A compound represented by [Chemical Formula 287] was synthesized by the following [Scheme 46].

[Scheme 46]

[Formula 9-a] [Formula 287]

5 g (15 mmol) of the compound represented by [Formula 9-a] obtained from [Scheme 45] of Example 9-1, 8.45 g (18) of the compound represented by [Formula 1-i] obtained from [Scheme 9] mmol), tris(dibenzylideneacetone) dipalladium 0.27 g (0.29 mmol), tritery butylphosphonium tetrafluoroborate 0.43 g (1.4 mmol), sodium tertiary reviewoxide 2.83 g (29 mmol) and xyl 50 mL of len was added and refluxed for 12 hours. When the reaction is finished, it is filtered under reduced pressure while hot. Separated by column chromatography to obtain 2.7 g of a compound represented by [Chemical Formula 287]. (Yield 25%)

MS [M] ⁺ : 735

<Example 10> Synthesis of a compound represented by [Chemical Formula 291]

(1) Synthesis of a compound represented by [Formula 10-a]

A compound represented by [Chemical Formula 10-a] was synthesized by the following [Scheme 47].

[Scheme 47]

[Formula 9-a] [Formula 10-a]

[Chemical Formula 1-d] used in [Scheme 5] of Example 1-5, [Chemical Formula 9-a] instead of iodobenzene, and iodonaphthalene were synthesized in the same manner except for using [Chemical Formula 10-a] 27 g of the compound represented by was obtained. (Yield 69%)

(2) Synthesis of a compound represented by [Formula 10-b]

A compound represented by [Chemical Formula 10-b] was synthesized by the following [Scheme 48].

[Scheme 48]

[Formula 10-a] [Formula 10-b]

Except for using [Chemical Formula 10-a] instead of [Chemical Formula 1-d] used in [Scheme 5] of Example 1-5, it was synthesized by the same method to obtain 17 g of a compound represented by [Chemical Formula 10-b] . (Yield 69%)

(3) Synthesis of a compound represented by [Chemical Formula 291]

A compound represented by [Chemical Formula 291] was synthesized by the following [Scheme 49].

[Scheme 49]

[Formula 10-b] [Formula 291]

Except for using [Formula 1-f] and [Formula 1-j] instead of [Formula 1-f] and [Formula 2-c] used in [Scheme 11] of Example 1-11, synthesized by the same method 3.5 g of a compound represented by [Chemical Formula 291] was obtained. (Yield 29%)

MS [M] ⁺ : 852

Examples 1 to 10: Preparation of 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 the substrate is mounted in a vacuum chamber, the base pressure is 1 × 10 ^-6 torr, and then an organic material is deposited on the ITO in the order of DNTPD (700 Å) and the organic light emitting compound (300 Å) according to the present invention. Subsequently, the host BH1 and 3% of the dopant BD1 were mixed to form a film (250 Å), and then compound E1: Liq = 1:1 (250 Å), Liq (10 Å), and Al (1,000 Å) were formed in the order, and at 0.4 mA The measurements were made.

<DNTPD> <BH1> <BD1>

<E1>

Comparative Example 1

An organic electroluminescent device was manufactured in the same manner, except that the following compounds were used instead of the organic light-emitting compounds according to the present invention in the above example, and the luminescence characteristics were also measured under the same conditions, 0.4 mA. For the organic electroluminescent devices manufactured according to Examples 1 to 10 and Comparative Example 1, voltage, 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 to 80% compared to the initial luminance (3000cd/㎡).

division Hole transport compound V Cd/㎡ CIEx CIEy T ₈₀ (Hrs)
at 3000cd/㎡ Comparative Example 1 α-NPB 4.3 650 0.133 0.129 85 Example 1 Formula 5 4.2 830 0.133 0.130 170 Example 2 Formula 7 4.2 850 0.133 0.128 150 Example 3 Formula 41 4.2 815 0.132 0.126 170 Example 4 Formula 49 4.1 790 0.132 0.127 165 Example 5 Formula 99 4.2 825 0.134 0.129 160 Example 6 Chemical Formula 147 4.1 810 0.132 0.128 145 Example 7 Chemical Formula 229 4.2 760 0.133 0.127 130 Example 8 Chemical Formula 258 4.1 805 0.133 0.129 150 Example 9 Chemical Formula 287 4.2 820 0.132 0.130 165 Example 10 Chemical Formula 291 4.2 815 0.133 0.130 140

As shown in [Table 1], the organic compound secured by the present invention has higher luminous efficiency and longer life than α-NPB, which is widely used as a material for a hole transport layer in the related art.

Claims (10)

An organic light emitting compound represented by any one of the following [Formula 1-1] to [Formula 1-2]:

[Formula 1-1] [Formula 1-2]
In the [Formula 1-1] to [Formula 1-2],
A ₁ to A ₂₀ are each independently CX ₁ to CX _20, and two adjacent two of A ₁ to A ₁₆ are bonded to the L to form a condensed ring ([*] means a binding site),
Z, W, Y and U are each independently CR ₁ R ₂ , NR ₃ , O, S or SiR ₄ R ₅ , and at least one of Z, W, Y and U is NR ₃ (wherein n is Is an integer from 0 to 3),
The R ₁ to R ₅ are the same as or different from each other, and each independently the following [Chemical Formula Q], hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms And a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,
X ₁ to X ₂₀ are each independently of the following [Chemical Formula Q], hydrogen, deuterium, halogen group, cyano group, substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, substituted Or an unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C1-C30 alkyl It is selected from a silyl group and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms,
At least one of X ₁ to X ₂₀ and R ₃ excluding those bound to * of L is the following [Formula Q],
[Formula Q]

In the above [Formula Q],
K is a single bond or a linking group selected from a substituted or unsubstituted arylene group having 5 to 50 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms,
m is an integer of 0 to 4, and when m is 2 or more, a plurality of Ks are the same or different from each other,
J ₁ and J ₂ are the same as or different from each other, and each independently, 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 carbon number of 5 to 50 It is selected from an aryl group and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms,
The K, J ₁ and J ₂ may be combined with each other or with an adjacent substituent to form a saturated or unsaturated ring. delete delete The method of claim 1,
The X ₁ to X ₂₀ , R ₁ to R ₅ , K and J ₁ to J ₂ are each independently deuterium, a cyano group, a halogen group, an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, and 5 to An organic light-emitting compound, characterized in that further substituted with one or more substituents selected from 24 aryl groups and C2-C24 heteroaryl groups. The method of claim 1,
Any one of the [Formula 1-1] to [Formula 1-2] is an organic light-emitting compound, characterized in that it is any one compound selected from the group represented by the following [Formula 2] to [Formula 460]:

[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]

[Chemical Formula 46] [Chemical Formula 47] [Chemical Formula 48] [Chemical Formula 49]

[Formula 50] [Formula 51] [Formula 52] [Formula 53]

[Formula 54] [Formula 55] [Formula 56] [Formula 57]

[Chemical Formula 58] [Chemical Formula 59] [Chemical Formula 60] [Chemical 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]

[Chemical Formula 78] [Chemical Formula 79] [Chemical Formula 80] [Chemical 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]

[Chemical Formula 118] [Chemical Formula 119] [Chemical Formula 120] [Chemical Formula 121]

[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]

[Chemical Formula 170] [Chemical Formula 171] [Chemical Formula 172] [Chemical 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]

[Chemical Formula 202] [Chemical Formula 203] [Chemical Formula 204] [Chemical 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 232] [Formula 233]

[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]

[Chemical Formula 250] [Chemical Formula 251] [Chemical Formula 252] [Chemical 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]

[Chemical Formula 270] [Chemical Formula 271] [Chemical Formula 272] [Chemical Formula 273]

[Formula 274] [Formula 275] [Formula 276] [Formula 277]

[Formula 278] [Formula 279] [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] [Formula 297]

[Formula 298] [Formula 299] [Formula 300] [Formula 301]

[Formula 302] [Formula 303] [Formula 304] [Formula 305]

[Formula 306] [Formula 307] [Formula 308] [Formula 309]

[Chemical Formula 310] [Chemical Formula 311] [Chemical Formula 312] [Chemical Formula 313]

[Formula 314] [Formula 315] [Formula 316] [Formula 317]

[Formula 318] [Formula 319] [Formula 320] [Formula 321]

[Formula 322] [Formula 323] [Formula 324] [Formula 325]

[Formula 326] [Formula 327] [Formula 328] [Formula 329]

[Formula 330] [Formula 331] [Formula 332] [Formula 333]

[Formula 334] [Formula 335] [Formula 336] [Formula 337]

[Formula 338] [Formula 339] [Formula 340] [Formula 341]

[Formula 342] [Formula 343] [Formula 344] [Formula 345]

[Formula 346] [Formula 347] [Formula 348] [Formula 349]

[Chemical Formula 350] [Chemical Formula 351] [Chemical Formula 352] [Chemical Formula 353]

[Formula 354] [Formula 355] [Formula 356] [Formula 357]

[Formula 358] [Formula 359] [Formula 360] [Formula 361]

[Formula 362] [Formula 363] [Formula 364] [Formula 365]

[Formula 366] [Formula 367] [Formula 368] [Formula 369]

[Formula 370] [Formula 371] [Formula 372] [Formula 373]

[Chemical Formula 374] [Chemical Formula 375] [Chemical Formula 376] [Chemical Formula 377]

[Chemical Formula 378] [Chemical Formula 379] [Chemical Formula 380] [Chemical Formula 381]

[Chemical Formula 382] [Chemical Formula 383] [Chemical Formula 384] [Chemical Formula 385]

[Chemical Formula 386] [Chemical Formula 387] [Chemical Formula 388] [Chemical Formula 389]

[Formula 390] [Formula 391] [Formula 392] [Formula 393]

[Chemical Formula 394] [Chemical Formula 395] [Chemical Formula 396] [Chemical Formula 397]

[Chemical Formula 398] [Chemical Formula 399] [Chemical Formula 400] [Chemical Formula 401]

[Formula 402] [Formula 403] [Formula 404] [Formula 405]

[Formula 406] [Formula 407] [Formula 408] [Formula 409]

[Formula 410] [Formula 411] [Formula 412] [Formula 413]

[Formula 414] [Formula 415] [Formula 416] [Formula 417]

[Formula 418] [Formula 419] [Formula 420] [Formula 421]

[Formula 422] [Formula 423] [Formula 424] [Formula 425]

[Formula 426] [Formula 427] [Formula 428] [Formula 429]

[Formula 430] [Formula 431] [Formula 432] [Formula 433]

[Formula 434] [Formula 435] [Formula 436] [Formula 437]

[Formula 438] [Formula 439] [Formula 440] [Formula 441]

[Formula 442] [Formula 443] [Formula 444] [Formula 445]

[Formula 446] [Formula 447] [Formula 448] [Formula 449]

[Chemical Formula 450] [Chemical Formula 451] [Chemical Formula 452] [Chemical Formula 453]

[Formula 454] [Formula 455] [Formula 456] [Formula 457]

[Formula 458] [Formula 459] [Formula 460] A first electrode; A second 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 organic light emitting compound of any one of [Formula 1-1] to [Formula 1-2] according to claim 1. The method of claim 6,
The organic layer is made of one or a plurality of organic layers including an emission layer, the organic layer further includes a hole transport layer,
An organic electroluminescent device comprising at least one organic light emitting compound in the hole transport layer. The method of claim 6,
The organic layer further comprises at least one layer selected from a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, and an electron injection layer. The method of claim 7,
The light emitting layer is an organic electroluminescent device, characterized in that each comprising at least one host compound and at least one dopant compound. The method of claim 6,
The organic light-emitting device is an organic light-emitting device, characterized in that it emits white light by including at least one organic light-emitting layer emitting blue, red, or green light.

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