KR20180037889A - Novel organic compounds and organic light-emitting diode therewith - Google Patents

Abstract

The present invention provides an organic compound of a specific structure capable of having high efficiency, low voltage and long lifetime properties by being used in a hole transport layer within an organic light emitting element, and an organic light emitting element including the same. The organic compound is represented by one among chemical formula A to chemical formula E.

Description

TECHNICAL FIELD [0001] The present invention relates to novel organic compounds and organic light-

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel organic compound and an organic light emitting device including the organic compound. More particularly, the present invention relates to a novel organic compound capable of realizing device characteristics such as high efficiency, long life and low- To an organic light emitting device.

The organic light emitting diode (OLED) is a display using a self-luminous phenomenon. The organic light emitting diode (OLED) has a wide viewing angle and is thinner and lighter than a liquid crystal display and has a fast response speed. ) Applications for display or illumination are expected.

Generally, an organic light emitting phenomenon refers to a phenomenon in which an organic material is used to convert electrical energy into light energy. The organic light emitting device using the organic light emitting phenomenon typically has a structure including an anode, an anode, and an organic layer between the anode and the cathode.

Here, in order to enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

The material used as the organic material layer in the organic light emitting device may be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material, Or a hole blocking layer may be added.

Among them, as a conventional technique relating to a hole transporting layer, a compound having a core structure in which at least one benzene ring is condensed in a carbazole structure is used as a hole transporting layer compound in JP-A 10-1074193 (Oct. A hole transport layer and a HOMO energy level between the HOMO energy level of the light emitting layer and a HOMO energy level between the hole transport layer and the light emitting layer are provided between the hole transporting layer and the light emitting layer in Patent Document 10-1455156 Discloses a technique relating to an organic light emitting element in which an auxiliary layer is formed.

However, although various methods for manufacturing an organic light emitting device having more efficient light emitting characteristics have been attempted in the prior art including the above-mentioned prior arts, it is still possible to operate at a low voltage, and the organic light emitting device having improved luminous efficiency and long life There is a continuing need to develop materials that can be used as a hole transport layer for a light emitting device.

Patent Registration No. 10-1074193 (Published on October 14, 2011) Patent Registration No. 10-1455156 (Publication date: Oct. 27, 2014)

Accordingly, the first technical object of the present invention is to provide an organic compound having a specific structure capable of having high efficiency, low voltage and long life characteristics by using it in a hole transporting layer in an organic light emitting device.

A second object of the present invention is to provide a novel organic light emitting device including the organic compound in a hole transport layer.

The present invention provides an organic compound represented by any one of the following formulas (A) to (E) in order to achieve the above technical problems.

(A)

[Chemical Formula B]

≪ RTI ID = 0.0 &

[Chemical Formula D]

(E)

In the above formulas (A) to (E)

X1 is CR < 11 > or N,

X2 is CR12 or N,

X3 is CR13 or N,

X4 is CR14 or N,

X5 is CR < 15 > or N,

X6 is CR16 or N,

X7 is CR < 17 > or N,

X8 is CR < 18 > or N,

X9 is CR < 19 > or N,

X10 is CR < 20 > or N,

At least two of X1 to X4 are selected from CR11 to CR14,

At least three of X5 to X10 are selected from CR15 to CR20,

)이며, Wherein one of X1 to X10 represents a carbon atom bonded to the A1

),

Substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C2-C30 alkenyl group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C2-C30 alkenyl group, A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6- A substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon number of 6 A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, A substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, An amide group, an ether group and an ester group,

The linking group L 1 is a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, And a substituted heteroarylene group having 2 to 60 carbon atoms,

n is an integer of 0 to 3, and when each of these is 2 or more, each of the linking groups L1 is the same or different from each other,

The substituents Ar1 and Ar2 are the same or different from each other and are each independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms or substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms,

Ar1 and L1 in A1 may be connected to each other to form a condensed ring, and Ar2 and L1 may be connected to each other to form a condensed ring.

According to another aspect of the present invention, there is provided a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises at least one organic compound of the present invention.

The organic light emitting device comprising the compound represented by any one of the formulas (A) to (E) in the hole transport layer according to the present invention can have high efficiency, low voltage and long life characteristics as compared with the conventional organic light emitting device.

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

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

The organic compound according to the present invention has a structure represented by any one of the following formulas (A) to (E).

(A)

[Chemical Formula B]

≪ RTI ID = 0.0 &

[Chemical Formula D]

(E)

In the above formulas (A) to (E)

X1 is CR < 11 > or N,

X2 is CR12 or N,

X3 is CR13 or N,

X4 is CR14 or N,

X5 is CR < 15 > or N,

X6 is CR16 or N,

X7 is CR < 17 > or N,

X8 is CR < 18 > or N,

X9 is CR < 19 > or N,

X10 is CR < 20 > or N,

At least two of X1 to X4 are selected from CR11 to CR14,

At least three of X5 to X10 are selected from CR15 to CR20,

)이며, Wherein one of X1 to X10 represents a carbon atom bonded to the A1

),

Substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C2-C30 alkenyl group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C2-C30 alkenyl group, A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6- A substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon number of 6 A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, A substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, An amide group, an ether group and an ester group,

The linking group L 1 is a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, And a substituted heteroarylene group having 2 to 60 carbon atoms,

n is an integer of 0 to 3, and when each of these is 2 or more, each of the linking groups L1 is the same or different from each other,

The substituents Ar1 and Ar2 are the same or different from each other and are each independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms or substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms,

Ar1 and L1 in A1 may be connected to each other to form a condensed ring, Ar2 and L1 may be connected to each other to form a condensed ring,

The 'substituted' in the 'substituted or unsubstituted' refers to a group selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, An alkenyl group, an alkynyl group having 2 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 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, An alkyl group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 6 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, An aryloxy group, an aryloxy group, an arylsilyl group, and an aryloxy group having 6 to 24 carbon atoms.

In consideration of the range of the alkyl or aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms" and "substituted or unsubstituted aryl group having 6 to 50 carbon atoms" in the present invention, The carbon number of the alkyl group having 1 to 30 carbon atoms and the aryl group having 6 to 50 carbon atoms means the total number of carbon atoms constituting the alkyl moiety or the aryl moiety when it is considered that the substituent is not substituted without considering the substituted moiety will be. For example, a phenyl group substituted with a butyl group at the para position should be considered to correspond to an aryl group having 6 carbon atoms substituted with a butyl group having a carbon number of 4.

The aryl group which is a substituent used in the compound of the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen elimination and includes a single or fused ring system containing 5 to 7 atoms, preferably 5 or 6 atoms, When a substituent is present in the aryl group, the adjacent substituent may be fused with each other to form a ring.

Specific examples of the aryl group include a phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m- terphenyl group, p- terphenyl group, naphthyl group, anthryl group, An aromatic group such as a pyridyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a perylenyle, a crycenyl, a naphthacenyl, a fluoranthene and the like, and at least one hydrogen atom of the aryl group may be substituted with a deuterium atom, (-NH ₂ , -NH (R), -N (R ') (R "), R' and R" each independently represent an alkyl group having 1 to 10 carbon atoms 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 alkyl group having 2 to 20 carbon atoms, An alkenyl group having 2 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, It may be substituted with a heteroaryl group of a small number of 6 to 24 aryl group, having 7 to 24 of the arylalkyl group, having 2 to 24 carbon atoms or heteroaryl group having 2 to 24.

The heteroaryl group which is a substituent used in the compound of the present invention is a heteroaryl group having 2 to 24 carbon atoms in which the heteroaryl group includes 1,2 or 3 hetero atoms selected from N, O, P, Si, S, Ge, Refers to a ring aromatic system, which rings may be fused to form a ring. And at least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as the aryl group.

In the present invention, the aromatic heterocyclic ring means that at least one of aromatic carbons in the aromatic hydrocarbon ring is substituted with at least one hetero atom selected from N, O, P, Si, S, Ge, Se and Te.

Specific examples of the alkyl group as the substituent used in the present invention include methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl and hexyl. The hydrogen atom may be substituted with a substituent similar to that of the aryl group.

Specific examples of the alkoxy group used as the substituent in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isoamyloxy, hexyloxy, At least one hydrogen atom in the alkoxy group may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the silyl group used as the substituent in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl , And dimethylpurylsilyl. At least one hydrogen atom of the silyl group may be substituted with the same substituent as the aryl group.

)인 구조를 갖는 화합물인 것을 특징으로 한다.In detail, the characteristics of the compounds represented by any one of the above-mentioned formulas (A) to (E) according to the present invention will be described in detail. The 6-membered aromatic ring containing X1 to X4, A six-membered ring containing a 6-membered aromatic carbon ring-oxygen atom containing a ring-X5 and X10 or X5 and X6 or X9 and X10 or a 6-membered ring containing X6 to X9 or X7 to X10 or X5 to X8 Aromatic carbon ring 'are condensed with each other, an indenodibenzofurane structure capable of containing a nitrogen atom in the ring structure, and one of X1 to X10 in these condensed rings is a carbon atom

). ≪ / RTI >

In one embodiment, in the above formulas (A) to (E), the substituents Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted And a heteroaryl group having 2 to 20 carbon atoms, and more preferably, they may be the same or different and independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present invention, among the substituents R11 to R20 in the above formulas (A) to (E), the substituent which is not bonded to A1 may be hydrogen or deuterium.

In one embodiment of the present invention, the linking group L 1 in the above-mentioned [Chemical Formulas A] to [E] is a single bond or any one selected from the following Structural Formulas 1 to 9.

[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]

In the structural formulas 1 to 9, the carbon of the aromatic ring is bonded to hydrogen or deuterium.

In one embodiment according to the present invention, in the above-mentioned formulas (A) to (E), n is an integer of 1 or 2, and when n is 2, each of the linking groups L1 may be the same or different from each other.

In the present invention, the compounds represented by formulas (A) to (E) may be characterized in that only one of X1 to X10 is a nitrogen atom or not all of them are nitrogen atoms.

On the other hand, the organic compound represented by any one of the above-mentioned [Chemical Formulas A] to [E] can exhibit improved long life characteristics when Al is bonded to the 1-position of the dibenzofuran moiety.

Here, the carbon position of the dibenzofuran moiety can be represented as shown in FIG.

<Figure A>

The dibenzofuran moiety in the above Formulas A to E is a moiety in which the ring member of the six-membered ring on the outer side of the furan ring in the 6-5-6-5-6 condensed ring is bonded to each position In the present invention, the first position of the dibenzofuran moiety corresponds to X6 in formula A, X7 in formula B, X9 in formula C, X10 in formula D, X5 in formula E, In Formula (A), A1 is bonded to the carbon of X6. In Formula (B), A1 is bonded to the carbon of X7. In Formula (C), A1 is bonded to the carbon of X9. E can exhibit improved long life characteristics when A1 is bonded to the carbon of X5.

Meanwhile, specific examples of the organic compound represented by any one of the above-mentioned formulas (A) to (E) according to the present invention may be any one selected from the compounds represented by the following [compounds 1] to [328] It does not.

<Compound 1> <Compound 2> <Compound 3> <Compound 4>

&Lt; Compound 5 > < Compound 6 > < Compound 7 > < Compound 8 &

&Lt; Compound 9 > < Compound 10 > < Compound 11 &

&Lt; Compound 13 > < Compound 14 > < Compound 15 > < Compound 16 &

&Lt; Compound 17 > < Compound 18 > < Compound 19 &

&Lt; Compound 21 > < Compound 22 > < Compound 23 &

<Compound 25> <Compound 26> <Compound 27> <Compound 28>

&Lt; Compound 29 > < Compound 30 > < Compound 31 &

<Compound 33> <Compound 34> <Compound 35> <Compound 36>

&Lt; Compound 37 > < Compound 38 > < Compound 39 &

&Lt; Compound 41 > < Compound 42 > < Compound 43 &

<Compound 45> <Compound 46> <Compound 47> <Compound 48>

&Lt; Compound 49 > < Compound 50 > < Compound 51 &

<Compound 53> <Compound 54> <Compound 55> <Compound 56>

&Lt; Compound 57 > < Compound 58 > < Compound 59 > < Compound 60 &

&Lt; Compound 61 > < Compound 62 > < Compound 63 > < Compound 64 &

<Compound 65> <Compound 66> <Compound 67> <Compound 68>

&Lt; Compound 69 > < Compound 70 > < Compound 71 > < Compound 72 &

<Compound 73> <Compound 74> <Compound 75> <Compound 76>

&Lt; Compound 77 > < Compound 78 > < Compound 79 > < Compound 80 &

<Compound 81> <Compound 82> <Compound 83> <Compound 84>

&Lt; Compound 85 > < Compound 86 > < Compound 87 > < Compound 88 &

&Lt; Compound 89 > < Compound 90 > Compound 91 > < Compound 92 &

<Compound 93> <Compound 94> <Compound 95> <Compound 96>

&Lt; Compound 97 > < Compound 98 > < Compound 99 > < Compound 100 &

&Lt; Compound 101 > < Compound 102 > < Compound 103 > < Compound 104 &

<Compound 105> <Compound 106> <Compound 107> <Compound 108>

&Lt; Compound 109 > < Compound 110 > < Compound 111 &

<Compound 113> <Compound 114> <Compound 115> <Compound 116>

&Lt; Compound 117 > < Compound 118 > < Compound 119 &

<Compound 121> <Compound 122> <Compound 123> <Compound 124>

<Compound 125> <Compound 126> <Compound 127> <Compound 128>

&Lt; Compound 129 > < Compound 130 > < Compound 131 &

<Compound 133> <Compound 134> <Compound 135> <Compound 136>

&Lt; Compound 137 > < Compound 138 > < Compound 139 &

<Compound 141> <Compound 142> <Compound 143> <Compound 144>

<Compound 145> <Compound 146> <Compound 147> <Compound 148>

<Compound 149> <Compound 150> <Compound 151> <Compound 152>

<Compound 153> <Compound 154> <Compound 155> <Compound 156>

<Compound 157> <Compound 158> <Compound 159> <Compound 160>

<Compound 161> <Compound 162> <Compound 163> <Compound 164>

<Compound 165> <Compound 166> <Compound 167> <Compound 168>

<Compound 169> <Compound 170> <Compound 171> <Compound 172>

<Compound 173> <Compound 174> <Compound 175> <Compound 176>

<Compound 177> <Compound 178> <Compound 179> <Compound 180>

<Compound 181> <Compound 182> <Compound 183> <Compound 184>

<Compound 185> <Compound 186> <Compound 187> <Compound 188>

<Compound 189> <Compound 190> <Compound 191> <Compound 192>

<Compound 193> <Compound 194> <Compound 195> <Compound 196>

<Compound 197> <Compound 198> <Compound 199> <Compound 200>

<Compound 201> <Compound 202> <Compound 203> <Compound 204>

<Compound 205> <Compound 206><Compound207><Compound208>

<Compound 209> <Compound 210> <Compound 211> <Compound 212>

<Compound 213> <Compound 214> <Compound 215> <Compound 216>

<Compound 217> <Compound 218> <Compound 219> <Compound 220>

&Lt; Compound 221 > < Compound 222 > < Compound 223 &

<Compound 225> <Compound 226> <Compound 227> <Compound 228>

<Compound 229> <Compound 230> <Compound 231> <Compound 232>

<Compound 233> <Compound 234> <Compound 235> <Compound 236>

&Lt; Compound 237 > < Compound 238 > < Compound 239 > < Compound 240 &

<Compound 241> <Compound 242> <Compound 243> <Compound 244>

<Compound 245> <Compound 246> <Compound 247> <Compound 248>

<Compound 249> <Compound 250> <Compound 251> <Compound 252>

<Compound 253> <Compound 254> <Compound 255> <Compound 256>

<Compound 257> <Compound 258> <Compound 259> <Compound 260>

<Compound 261> <Compound 262> <Compound 263> <Compound 264>

<Compound 265> <Compound 266> <Compound 267> <Compound 268>

<Compound 269> <Compound 270> <Compound 271> <Compound 272>

<Compound 273> <Compound 274> <Compound 275> <Compound 276>

<Compound 277> <Compound 278> <Compound 279> <Compound 280>

<Compound 281> <Compound 282> <Compound 283> <Compound 284>

<Compound 285> <Compound 286> <Compound 287> <Compound 288>

<Compound 289> <Compound 290> <Compound 291> <Compound 292>

<Compound 293> <Compound 294> <Compound 295> <Compound 296>

<Compound 297> <Compound 298> <Compound 299> <Compound 300>

<Compound 301> <Compound 302> <Compound 303> <Compound 304>

<Compound 305> <Compound 306> <Compound 307> <Compound 308>

<Compound 309> <Compound 310> <Compound 311> <Compound 312>

<Compound 313> <Compound 314> <Compound 315> <Compound 316>

&Lt; Compound 317 > < Compound 318 > < Compound 319 > < Compound 320 &

<Compound 321> <Compound 322> <Compound 323> <Compound 324>

<Compound 325> <Compound 326> <Compound 327> <Compound 328>

The present invention also provides a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes the organic compound according to the present invention described above.

Herein, "(organic layer) contains at least one organic compound" in the present invention means that one or more organic compounds belonging to the category of the present invention (organic layer) Compound "as used herein.

At this time, the organic light emitting device of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer.

The organic layer containing the organic compound may be used for at least one of a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, a light emitting layer, an electron transporting layer, and an electron injecting layer, The organic compound can be used for the hole transport layer.

As the material for the hole transporting layer used in the organic light emitting device according to the present invention, an organic compound represented by any one of the above-mentioned formulas (A) to (E) ], And other compounds may be used as a hole transport layer commonly used in the art.

As such a hole transporting layer material, electron donating molecules having a small ionization potential can be used, and diamine, triamine or tetraamine derivative having a basic skeleton of triphenylamine is widely used, and for example, N, N'- Bis (3-methylphenyl) -N, N'-diphenyl- [1,1-biphenyl] -4,4'- diamine (TPD) or N, N'- N'-diphenylbenzidine (a-NPD), and the like.

A hole injection layer (HIL) may be additionally formed on the lower portion of the hole transport layer. The hole injection layer material may also be an organic compound represented by any one of the formulas (A) to (E) Can be used. In the case where the organic compound represented by any one of the above-mentioned formulas [A] to [E] is not used, a hole injecting layer commonly used in the art can be used.

Such conventionally used hole injection layers include, for example, HATCN (hexaazatriphenylene hexacarbonitrile), CuPc (copper phthalocyanine), TCTA (4,4 ', 4 "-tri (N-carbazolyl) triphenyl- (4,4 ', 4 "-tris- (3-methylphenylphenylamino) triphenylamine) or the like may be used.

In addition, the light emitting layer in the organic light emitting device of the present invention may be composed of a host and a dopant. In this case, the host used in the light emitting layer may include at least one compound represented by the following chemical formula (K) .

[Chemical formula K]

In the above formula (K)

X ₁₁ to X ₂₀ are the same or different from each other and each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, 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 aryloxy group having 6 to 30 carbon atoms , A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon number 6 A substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having a hetero atom, O, N or S, a substituted Or a group selected from the group consisting of an unsubstituted silicon 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 hydroxyl group, a nitro group, a halogen group, And the groups adjacent to each other may form a condensed ring of an aliphatic, aromatic, aliphatic hetero or aromatic hetero.

More specifically, the host may be represented by any one selected from the group consisting of the following formulas (301) to (496), but is not limited thereto.

[Formula 3] &lt; EMI ID =

[Chemical Formula 308] [Chemical Formula 308]

[311] &lt; EMI ID =

[313] [313] [315] [316]

[Formula 31] [Formula 31] [Formula 31] [Formula 31]

(324) [Formula 322]

[328] [328] [328] [328]

[333] [333] [332]

(336) [Chemical Formula 336] [Chemical Formula 336]

[Chemical Formula 33] [Chemical Formula 33] [Chemical Formula 33]

(344) [Chemical Formula 344] [Chemical Formula 344]

[Chemical Formula 347] [Chemical Formula 348] [Chemical Formula 348]

[353] [351] [352]

[356] [356] [356]

[Chemical Formula 357] [Chemical Formula 359]

[363] [363] [363] [364]

[368] [366] [368] [368]

[370] [370]

[376] [376] [376] [376]

[380] [380] [380] [380]

[Formula 38] [Formula 384] [Formula 384]

[Formula 388] [Formula 388] [Formula 388]

[390] [390] [392] [392]

[396] [396] [396]

[Formula 39] [Chemical Formula 39] [Chemical Formula 39] [Chemical Formula 39]

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

(408) [Chemical Formula 408]

[410] [410] [411] [412]

[414] [415] [415] [416]

[Chemical Formula 417] [Chemical Formula 413]

[422] [422] [422]

[428] [428] [428] [428]

[Chemical Formula 431] [Chemical Formula 431] [Chemical Formula 432]

[Chemical Formula 435] [Chemical Formula 436] [Chemical Formula 436]

[440] [440] [440]

(444) [Chemical Formula 444] [Chemical Formula 444]

[Chemical Formula 447] [Chemical Formula 447] [Chemical Formula 448]

[Formula 45] [Chemical Formula 452] [Chemical Formula 452]

[Formula 456] [Formula 456] [Formula 456]

[Chemical Formula 457] [Chemical Formula 457] [Chemical Formula 460]

[Chemical Formula 463] [Chemical Formula 464] [Chemical Formula 464]

[Formula 466] [Formula 466] [Formula 468]

[Chemical Formula 470] [Chemical Formula 471] [Chemical Formula 472]

[Chemical Formula 477] [Chemical Formula 477] [Chemical Formula 476]

[Formula 477] [Formula 477] [Formula 480]

[Formula 48] [Formula 48] [Formula 484]

[488] [488] [488] [488] [488]

[Formula 492] [Formula 492] [Formula 492]

[Formula 49] [Formula 496] [Formula 496]

Meanwhile, the dopant used in the light emitting layer in the organic light emitting device of the present invention may be a compound represented by the following formula (1) or (2), and various known dopant materials may be used.

            [Chemical Formula 1] &lt; EMI ID =

Among the above-mentioned formulas (1) and (2)

A is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms , A substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms having a hetero atom O, N or S, and the like.

More specifically, A is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms or a single bond, preferably an anthracene, pyrene, phenanthrene, indenophenanthrene, klysene, naphthacene, Perylene, pentacene, and more particularly, the A may be a substituent represented by any one of the following formulas (A1) to (A10).

[Formula A1] [Formula A2] [Formula A3]

[Chemical Formula A4] [Chemical Formula A5] [Chemical Formula A6]

[Chemical formula A7] [Chemical formula A8] [Chemical formula A9]

(A10)

Wherein Z ₁ to Z ₂ in the formula [A3] are each independently selected from the group consisting of hydrogen, a deuterium atom, 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 alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted Or an unsubstituted or substituted aryl group having 6 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 aryl group having 2 to 60 carbon atoms (Substituted or unsubstituted C1-C60 alkyl) amino group, or a substituted or unsubstituted C6-C60 aryl) amino group, a substituted or unsubstituted C1-C60 alkylamino group, , (Substituted or unsubstituted aryl group having 6 to 60 carbon atoms) amino group, and Z ₁ to Z ₂ are the same or different from each other and can form a condensed ring with adjacent groups.

In the above formula (1)

X ₂₁ and X ₂₂ are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a single bond, X ₂₁ and X ₂₂ may be bonded to each other,

Y ₁ and Y ₂ are 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 a substituted or unsubstituted C1 to C24 heteroalkyl group, a substituted or unsubstituted C3 to C24 cycloalkyl group, a substituted or unsubstituted C1 to C24 alkoxy group, a cyano group, a halogen group, a substituted or unsubstituted carbon number A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron, deuterium, and hydrogen. more selected species and, Y ₁ to Y ₂ each are the same or different each other, may form a fused ring group of the aliphatic, aromatic, aliphatic hetero, or aromatic heterocyclic group which are adjacent to each other It was,

Each of l and m is an integer of 1 to 20, and n is an integer of 1 to 4.

In the above formula (2)

C _y is a substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms, b is an integer of 1 to 4, and when b is 2 or more, each cycloalkane may be in a fused form, Each of which may be substituted with deuterium or alkyl, and may be the same as or different from each other.

In addition, Is a single bond or - [C (R ₂₅ ) (R ₂₆ )] _p -, and p is an integer of 1 to 3; when p is 2 or more, R ₂₅ and R ₂₆ are the same or different from each other;

R ₂₁ , R ₂₂ , R _23, R ₂₅ and R ₂₆ independently represent 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 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 , A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted aryloxy group having 6 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, Or rain (Substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, or a substituted or unsubstituted (having 6 to 60 carbon atoms) amino group, a di (substituted or unsubstituted) alkyl group having 1 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,

a is an integer of 1 to 4, and when a is 2 or more, R ₂₃ of 2 or more are the same or different, and when R ₂₃ is plural, each R ₂₃ may be in fused form, and n is 1 to 4 It is an integer.

The amine group bonded to A in the formulas (1) and (2) may be represented by any one selected from the group consisting of the following [substituents 1] to [52], but is not limited thereto.

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

[Substituent group 4] [Substituent group 5] [Substituent group 6]

[Substituent group 7]   [Substituent group 8] [Substituent group 9]

 [Substituent group 10] [Substituent group 11] [Substituent group 12]

 [Substituent group 13] [Substituent group 14] [Substituent group 15]

 [Substituent group 16] [Substituent group 17] [Substituent 18]

 [Substituent group 19] [Substituent group 20] [Substituent group 21]

 [Substituent 22]     [Substituent group 23] [Substituent group 24]

[Substituent group 25] [Substituent group 26] [Substituent group 27]

[Substituent 28]    [Substituent group 29] [Substituent group 30]

[Substituent 31]    [Substituent group 32] [Substituent group 33]

[Substituent group 34] [Substituent group 35] [Substituent group 36]

[Substituent group 37]    [Substituent group 38] [Substituent group 39]

[Substituent 40]   [Substituent group 41] [Substituent group 42]

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

[Substituent group 46] [Substituent group 47] [Substituent group 48]

[Substituent group 49] [Substituent group 50] [Substituent group 51]

[Substituent 52]

In the above substituents, R may be the same or different from each other and is selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or 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, a substituted or unsubstituted C1- A substituted or unsubstituted alkylthio 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 6 to 60 carbon atoms, a substituted or unsubstituted C1 to C60 alkoxy group, A substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, (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 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 each has 1 To 12 carbon atoms, and each of the substituents may form a condensed ring with adjacent groups.

The light emitting layer may further include various dopants and various hosts as well as the dopant and the host.

When the light emitting layer according to the present invention includes a host and a dopant, the dopant may be selected from the range of about 0.01 to about 20 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

On the other hand, examples of the electron transport layer compound commonly used for the electron transport layer include quinoline derivatives, especially tris (8-quinolinolate) aluminum (Alq3), TAZ, BAlq, beryllium bis (benzoquinolyl- But are not limited to, materials such as beryllium bis (benzoquinolin-10-olate: Bebq2), BCP, compound 501 and compound 502, and oxadiazole derivatives such as PBD, BMD and BND.

TAZ BAlq

&Lt; Compound 501 > < Compound 502 > BCP

As the electron transporting layer compound in the invention, the organometallic compounds represented by the above formula (F) may be used singly or in combination.

 [Chemical Formula F]

In the above formula (F)

Y is a moiety selected from C, N, O and S, which is directly bonded to M to form a single bond, and any moiety selected from C, N, O and S is a moiety coordinating to M And is a ligand chelated by coordination bond with the single bond; Wherein M is an alkali metal, an alkaline earth metal, an aluminum (Al), or a boron (B) atom, and OA is a monovalent ligand capable of single bond or coordination bond with M,

O is oxygen,

A represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted C2 to C20 Substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl groups having 5 to 30 carbon atoms, and substituted or unsubstituted hetero atoms having 2 to 50 carbon atoms having O, N or S, An aryl group,

M is 1 and n is 0 when M is a metal selected from an alkali metal,

M = 1, n = 1, or m = 2 and n = 0 when M is a metal selected from alkaline earth metals,

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

In the present invention, Y may be the same or different and independently of each other may be any one selected from the following formulas [C1] to [C39], but is not limited thereto.

[Structural formula C1] [Structural formula C2] [Structural formula C3]

[Structural formula C4] [Structural formula C5] [Structural formula C6]

[Structural formula C7] [Structural formula C8] [Structural formula C9] [Structural formula C10]

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

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

[Structural formula C17] [Structural formula C18] [Structural formula C19] [Structural formula C20]

[Structural formula C21] [Structural formula C22] [Structural formula C23]

[Structural formula C24] [Structural formula C25] [Structural formula C26]

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

[Structural formula C31] [Structural formula C32] [Structural formula C33]

[Structural formula C34] [Structural formula C35] [Structural formula C36]

[Structural formula C37] [Structural formula C38] [Structural formula C39]

In the above Structural Formula C1 to Structural Formula C39,

R is the same or different and is each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C6-30 aryl, A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms And may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring. Herein, the 'substitution' in the 'substituted or unsubstituted' refers to a substituent selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group, alkoxy group, alkylamino group, arylamino group, heteroarylamino group, An aryl group, a heteroaryl group, germanium, phosphorus, and boron. The term &quot; substituted aryl group &quot;

Meanwhile, an electron injection layer (EIL) may be further formed on the electron transport layer to facilitate injection of electrons from the cathode to ultimately improve power efficiency. The electron injection layer material As long as it is commonly used in the related art, it can be used without any particular limitation. For example, materials such as LiF, NaCl, CsF, Li ₂ O, and BaO can be used.

The deposition conditions of the electron injection layer may vary depending on the compound used, but may generally be selected from the same range of conditions as the formation of the hole injection layer.

The thickness of the electron injecting layer may be from about 1 A to about 100 A, and from about 3 A to about 90 A. When the thickness of the electron injection layer satisfies the above-described range, satisfactory electron injection characteristics can be obtained without substantially increasing the driving voltage.

In the present invention, the negative electrode may be formed of a material selected from the group consisting of Li, Mg, Al, Al-Li, Ca, Mg- Mg-Ag), or a transmissive negative electrode using ITO or IZO can be used to obtain a top-emitting device.

In the present invention, at least one layer selected from the functional layer having the hole injection layer, the hole transport layer, the hole injection function and the hole transport function, the light emitting layer, the electron transport layer, and the electron injection layer may be formed by a deposition process or a solution process .

Here, the deposition method refers to a method of forming a thin film by evaporating a material used as a material for forming each of the layers through heating or the like under vacuum or low pressure, Refers to a method of mixing a material used as a material with a solvent and forming the thin film by a method such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating or the like.

Further, the organic light emitting device of the present invention may be a flat panel display device; A flexible display device; Monochrome or white flat panel illumination devices; And a single-color or white-colored flexible lighting device.

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

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

Referring to FIG. 1, the organic light emitting device of the present invention and a method of manufacturing the same will be described below. First, an anode electrode material is coated on the substrate 10 to form an anode 20. Here, as the substrate 10, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity are used.

A hole injection layer 30 is formed on the anode 20 by vacuum thermal deposition or spin coating. Subsequently, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating on the hole transport layer 30 above the hole injection layer 30.

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

After the electron transport layer 60 is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode forming metal is deposited on the electron injection layer 70 in a vacuum heat- And the cathode 80 is formed by vapor deposition to complete the organic EL device. Here, as the metal for forming the cathode, lithium, magnesium, aluminum, aluminum-lithium, calcium, magnesium-magnesium, Mg-Ag), and a transmissive cathode using ITO or IZO can be used to obtain a top light-emitting device.

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

Synthetic example  1. [Compound 1]  synthesis

Synthetic example  1-1. Synthesis of [intermediate 1-a]

                                     [Intermediate 1-a]

A round bottom flask was charged with 25 g (118 mmol) of dibenzofuran-1-boronic acid, 40.5 g (118 mmol) of methyl-5-bromo- mmol), potassium carbonate (33 g, 237 mmol), toluene (200 ml), 1,4-dioxane (200 ml) and water (100 ml) were added under nitrogen and refluxed for 12 hours. After completion of the reaction, the reaction product was separated, and the organic layer was concentrated under reduced pressure, and then separated by column chromatography to obtain 33.5 g of [intermediate 1-a]. (Yield: 74%)

Synthetic example  1-2. Synthesis of [intermediate 1-b]

                           [Intermediate 1-b]

Add 33.5 g (110 mmol) of [intermediate 1-a] to a round bottom flask containing 150 ml of tetrahydrofuran, lower the temperature to -10 ° C, and add 85 ml (254 mmol) of 3 M methylmagnesium bromide slowly dropwise. After raising the temperature to 40 占 폚, the mixture is stirred for 4 hours. After lowering the temperature to -10 ° C, 70 ml of 2N hydrochloric acid is slowly added dropwise, 70 ml of aqueous ammonium chloride solution is added, and the temperature is raised to room temperature. After completion of the reaction, the reaction product was washed with water, concentrated under reduced pressure, and then separated by column chromatography to obtain 27 g of [intermediate 1-b]. (Yield: 80%)

Synthetic example  1-3. [Synthesis of intermediate 1-c]

                       [Intermediate 1-c]

In a round bottom flask, 27 g (89.2 mmol) of [intermediate 1-b] and 70 ml of phosphoric acid were added under nitrogen atmosphere, and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the mixture was extracted, concentrated and then subjected to column chromatography to obtain 17.6 g of [intermediate 1-c]. (70% yield)

Synthetic example  1-4. [compound 1]  synthesis

                                                  [Compound 1]

A round bottom flask was charged with 10 g (27.5 mmol) of Intermediate 1-c, 8.8 g (27.5 mmol) of bis (4-biphenyl) amine, 0.5 g (0.6 mmol) of bisdibenzylidene acetone dipalladium, 0.7 g 1.1 mmol), sodium tertiary butylate (6.6 g, 68.8 mmol) and toluene (100 ml) were added under a nitrogen atmosphere and refluxed for 12 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure, and then separated by column chromatography to obtain 11.8 g of [Compound 1]. (Yield: 72%)

MS (MALDI-TOF): m / z 603.26 [M] ^&lt; ^{+ &}

Synthetic example  2. [Compound 3]  synthesis

Synthetic example  2-1. [compound 3]  synthesis

                                             [Compound 3]

Except that N- (naphthalene-2-yl) biphenyl-4-amine was used in place of the bis (4-biphenyl) amine used in Synthesis Example 1-4. [Compound 3] was obtained. (Yield 67%)

MS (MALDI-TOF): m / z 577.24 [M] ^&lt; ^{+ &}

Synthetic example  3. [Compound 67]  synthesis

Synthetic example  3-1. Synthesis of [intermediate 3-a]

                 [Intermediate 3-a]

50 g (183 mmol) of 2-bromo-9,9-dimethylfluorene, 59.3 g (1098 mmol) of sodium methoxide, 10.4 g (54.9 mmol) of copper iodide and 200 ml of methanol were added to a round bottom flask under nitrogen Was added and refluxed for 12 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain 33.2 g of [intermediate 3-a]. (Yield: 81%)

Synthetic example  3-2. Synthesis of [intermediate 3-b]

                       [Intermediate 3-b]

30 g (133 mmol) of Intermediate 3-a, 23.8 g (133 mmol) of N-bromosuccinimide and 600 ml of dimethylformamide were added to a round bottom flask under nitrogen atmosphere and stirred at 50 DEG C for 12 hours . After completion of the reaction, the organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain 28 g of [intermediate 3-b]. (70% yield)

Synthetic example  3-3. [Synthesis of intermediate 3-c]

                       [Intermediate 3-c]

49.7 g (164 mmol) of Intermediate 3-b was added to a round bottom flask, 500 ml of tetrahydrofuran was added under nitrogen atmosphere, the temperature was lowered to -78 ° C., 123 ml (197 mmol) of 1.6 M butyllithium was slowly dropped I will. After 1 hour, 22 ml (214 mmol) of trimethyl borate was slowly added thereto while keeping the temperature at low temperature, and the temperature was raised to room temperature and stirred. After completion of the reaction, the organic layer was concentrated under reduced pressure and recrystallized with hexane to obtain 35.6 g (yield: 81%) of [Intermediate 3-c].

Synthetic example  3-4. Synthesis of [intermediate 3-d]

                                               [Intermediate 3-d]

Instead of the dibenzofuran-1-boronic acid used in Synthesis Example 1-1, [Intermediate 3-c] was used and instead of methyl-5-bromo-2-iodobenzoate 1-bromo-3- -Fluorobenzene, the intermediate 3-d was obtained. (Yield: 52%)

Synthetic example  3-5. Synthesis of [intermediate 3-e]

                       [Intermediate 3-e]

30 g (85 mmol) of Intermediate 3-d and 300 ml of dichloromethane were added to a round bottom flask under nitrogen, and 63.9 g (255 mmol) of boron tribromide was diluted in 150 ml of dichloromethane Let go slowly. The temperature was raised to room temperature and stirred for 6 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain 21.3 g of [intermediate 3-e]. (Yield: 74%)

Synthetic example  3-6. [Synthesis of intermediate 3-f]

                            [Intermediate 3-f]

20 g (59 mmol) of Intermediate 3-e, 13 g (94.5 mmol) of potassium carbonate and 200 ml of 1-methyl-2-pyrrolidinone were added to a round bottom flask under nitrogen atmosphere and stirred at 150 DEG C for 12 hours Respectively. After completion of the reaction, the organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain 13.5 g of [intermediate 3-f]. (Yield: 72%)

Synthetic example  3-7. [compound 67]  synthesis

                                                  [Compound 67]

[Compound 67] was obtained in the same manner as Intermediate 3-f except for using [Intermediate 3-f] instead of [Intermediate 1-c] used in Synthesis Examples 1-4. (70% yield)

MS (MALDI-TOF): m / z 603.26 [M] ^&lt; ^{+ &}

Synthetic example  4. [Compound 68]  synthesis

Synthetic example  4-1. Synthesis of [intermediate 4-a]

                                             [Intermediate 4-a]

Instead of dibenzofuran-1-boronic acid used in Synthesis Example 1-1, 4-aminophenylboronic acid pinacol ester was used instead of methyl-5-bromo-2-iodobenzoate, Dimethylfluorene was used in place of 9-dimethylfluorene to obtain [intermediate 4-a]. (Yield: 72%)

Synthetic example  4-2. [Synthesis of intermediate 4-b]

                                             [Intermediate 4-b]

7.0 g (30.6 mmol) of 4-bromobiphenyl, 0.4 g (0.3 mmol) of palladium acetate and 4.2 g (43 mmol) of sodium tertiary butoxide were added to a 250 ml reactor, 0.1 g (0.3 mmol) of triturated butylphosphine and 100 ml of toluene were placed, and the mixture was refluxed with stirring for 13 hours. After completion of the reaction, the reaction mixture was filtered, and the filtrate was concentrated and separated by column chromatography to obtain 7.0 g of [intermediate 4-b]. (Yield: 65%)

Synthetic example  4-3. [compound 68]  synthesis

[화합물 68]

[Compound 68]

Synthesis was carried out in the same manner except that [Intermediate 4-b] was used instead of the bis (4-biphenyl) amine used in Synthesis Example 1-4 and [Intermediate 3-f] was used instead of [Intermediate 1-c] [Compound 68] was obtained. (Yield: 73%)

MS (MALDI-TOF): m / z 719.32 [M] ^&lt; ^{+ &}

Synthetic example  5. [Compound 111]  synthesis

Synthetic example  5-1. Synthesis of [intermediate 5-a]

                                  [Intermediate 5-a]

Except that phenylboronic acid was used in place of dibenzofuran-1-boronic acid used in Synthesis Example 1-1 and 3-bromodibenzofuran was used instead of methyl-5-bromo-2-iodobenzoate To obtain [Intermediate 5-a]. (Yield: 76%)

Synthetic example  5-2. [Synthesis of intermediate 5-b]

                   [Intermediate 5-b]

 50 g (204 mmol) of Intermediate 5-a and 500 ml of tetrahydrofuran were added to a round bottom flask under nitrogen, the temperature was lowered to -78 ° C, and 128 ml (204 mmol) of 1.6 M-butyllithium was slowly added dropwise Stir for 1 hour. 14.3 g (245 mmol) of acetone was slowly added dropwise thereto, followed by stirring at room temperature for 6 hours. After completion of the reaction, 50 ml of ammonium chloride aqueous solution was added and the mixture was layered. The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain [Intermediate 5-b] (38.3 g). (Yield: 62%)

Synthetic example  5-3. Synthesis of [intermediate 5-c]

                              [Intermediate 5-c]

Intermediate 5-c] was obtained in the same manner as Intermediate 5-b except for using [Intermediate 5-b] instead of [Intermediate 1-b] used in Synthesis Examples 1-3. (Yield 69%)

Synthetic example  5-4. Synthesis of [intermediate 5-d]

                           [Intermediate 5-d]

14.5 g (50.9 mmol) of Intermediate 5-c was added to a round bottom flask, 150 ml of tetrahydrofuran was added under nitrogen atmosphere, the temperature was lowered to -78 ° C., and 35 ml (56 mmol) of 1.6 M butyllithium was slowly dropped I will. After 1 hour, 6.3 ml (61.1 mmol) of trimethylborate was slowly added thereto while keeping the temperature at low temperature, and the temperature was raised to room temperature and stirred. After completion of the reaction, the organic layer was concentrated under reduced pressure and recrystallized from hexane to obtain 14.9 g (yield 80%) of [intermediate 5-d].

Synthetic example  5-5. [compound 111]  synthesis

                                           [Compound 111]

[Compound 111] was synthesized in the same way except that [Intermediate 5-d] was used in place of [Intermediate 1-c] used in Synthesis Examples 1-4. (70% yield)

MS (MALDI-TOF): m / z 603.26 [M] ^&lt; ^{+ &}

Synthetic example  6. [Compound 120]  synthesis

Synthetic example  6-1. Synthesis of [intermediate 6-a]

                                   [Intermediate 6-a]

Synthesis was conducted in the same manner as in Synthesis Example 4-2, except that 4-aminobiphenyl was used instead of [intermediate 4-a] and 1-bromodibenzofuran was used instead of 4-bromobiphenyl, to obtain Intermediate 6- a] was obtained. (Yield: 58%)

Synthetic example  6-2. [compound 120]  synthesis

                                               [Compound 120]

Synthesis was carried out in the same manner except that [Intermediate 6-a] was used instead of the bis (4-biphenyl) amine used in Synthesis Example 1-4 and [Intermediate 5-d] was used instead of [Intermediate 1-c] [Compound 120] was obtained. (70% yield)

MS (MALDI-TOF): m / z 617.24 [M] ^&lt; ^{+ &}

Synthetic example  7. [Compound 136]  synthesis

Synthetic example  7-1. [Synthesis of intermediate 7-a]

[Intermediate 7-a]

Dibenzofuran-3-boronic acid was used instead of the dibenzofuran-1-boronic acid used in Synthesis Example 1-1, methyl-5-bromo-2-iodobenzoate -Iodobenzoate synthesized in the same manner as in Synthesis Examples 1-1 to 1-3, whereby [Intermediate 7-a] was obtained. (70% yield)

Synthetic example  7-2. [compound 136]  synthesis

                                                [Compound 136]

Synthesis was conducted in the same way except that [Intermediate 7-a] was used instead of [Intermediate 1-c] used in Synthesis Examples 1-4 to obtain [Compound 136]. (Yield: 72%)

MS (MALDI-TOF): m / z 603.26 [M] ^&lt; ^{+ &}

Synthetic example  8. [Compound 141]  synthesis

Synthetic example  8-1. [Synthesis of intermediate 8-a]

[Intermediate 8-a]

Was synthesized in the same manner as in Synthesis Examples 1-1 to 1-3 using dibenzofuran-3-boronic acid instead of dibenzofuran-1-boronic acid used in Synthesis Example 1-1 to give [Intermediate 8-a] . (Yield: 68%)

Synthetic example  8-2. [compound 141]  synthesis

                                                [Compound 141]

(4-biphenyl) - (9,9-dimethylfluoren-2-yl) amine was used instead of the bis (4-biphenyl) [Synthesis of Intermediate 8-a] [Compound 141] was synthesized in the same manner as Intermediate 8-a. (Yield: 75%)

MS (MALDI-TOF): m / z 643.29 [M] ^&lt; ^{+ &}

Synthetic example  9. [Compound 181]  synthesis

Synthetic example  9-1. Synthesis of [intermediate 9-a]

                    [Intermediate 9-a]

50 g (202 mmol) of 3-bromodibenzofuran, 54.6 g (1214 mmol) of sodium methoxide aqueous solution, 11.5 g (60.7 mmol) of copper iodide and 200 ml of methanol were added to a round bottom flask under a nitrogen atmosphere, . After completion of the reaction, the organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain 36 g of [intermediate 9-a]. (Yield: 90%)

Synthetic example  9-2. [Synthesis of intermediate 9-b]

                       [Intermediate 9-b]

36 g (181 mmol) of Intermediate 9-a, 32.3 g (181 mmol) of N-bromosuccinimide and 700 ml of dimethylformamide were placed in a round bottom flask and stirred at 50 ° C for 12 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain 35 g of [intermediate 9-b]. (70% yield)

Synthetic example  9-3. [Synthesis of intermediate 9-c]

                         [Intermediate 9-c]

Intermediate 9-c] was obtained in the same manner except that [Intermediate 9-b] was used instead of [Intermediate 3-b] used in Synthesis Example 3-3. (Yield: 78%)

Synthetic example  9-4. Synthesis of intermediate 9-d

                                         [Intermediate 9-d]

[Intermediate 9-c] was used instead of the dibenzofuran-1-boronic acid used in Synthesis Example 1-1, and methyl-2-bromobenzoate was used instead of methyl-5-bromo- Was synthesized in the same manner as [Intermediate 9-d]. (Yield 64%)

Synthetic example  9-5. Synthesis of [intermediate 9-e]

                     [Intermediate 9-e]

[Intermediate 9-e] was obtained by the same method except for using [Intermediate 9-d] instead of [Intermediate 1-a] used in Synthesis Example 1-2. (Yield: 77%)

Synthetic example  9-6. [Synthesis of intermediate 9-f]

                       [Intermediate 9-f]

[Intermediate 9-e] was used instead of [Intermediate 1-b] used in Synthesis Example 1-3 to obtain Intermediate 9-f. (Yield 67%)

Synthetic example  9-7. Synthesis of intermediate 9-g

                            [Intermediate 9-g]

In a round bottom flask, add 30 g (95.4 mmol) of intermediate 9-f and 200 ml of dichloromethane in a nitrogen atmosphere and lower the temperature to 0 ° C. 120 g (143 mmol) of boron tribromide was diluted in 300 mL of dichloromethane, and the mixture was slowly dropped, followed by stirring at room temperature for 3 hours. After completion of the reaction, the reaction mixture was poured into 1 L of distilled water, and the organic layer was concentrated under reduced pressure and then subjected to column chromatography to obtain 19.2 g of [intermediate 9-g]. (Yield 67%)

Synthetic example  9-8. [Synthesis of intermediate 9-h]

                          [Intermediate 9-h]

Add 10 g (33.2 mmol) of [intermediate 9-g] in a round bottom flask under nitrogen and lower the temperature to 0 ° C. 3.2 ml (39.9 mmol) of pyridine and 7.3 ml (43.2 mmol) of trifluoromethanesulfonic anhydride were slowly added dropwise thereto, followed by stirring at room temperature for 2 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain 12.2 g of [intermediate 9-h]. (Yield: 85%)

Synthetic example  9-9. [compound 181]  synthesis

                                                 [Compound 181]

To a round bottom flask was added 17.3 g (40 mmol) of Intermediate 9-h, 19.3 g (60 mmol) of bis (4-biphenyl) amine, 0.5 g (2 mmol) of palladium acetate, 1.9 g 5.8 g (60 mmol) of Tartar Reviews Tosoxide and 200 ml of toluene were added under a nitrogen atmosphere, stirred at room temperature for 30 minutes, and then refluxed at 120 ° C for 12 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure, and then separated by column chromatography to obtain 14.7 g of [Compound 181]. (Yield: 61%)

MS (MALDI-TOF): m / z 603.26 [M] ^&lt; ^{+ &}

Synthetic example  10. [Compound 183]  synthesis

Synthetic example  10-1. Synthesis of [intermediate 10-a]

                           [Intermediate 10-a]

Instead of the dibenzofuran-1-boronic acid used in Synthesis Example 1-1 and using biphenyl-4-boronic acid instead of methyl-5-bromo-2-iodobenzoate, Was synthesized in the same manner as in [Intermediate 10-a] except that benzene was used. (Yield: 74%)

Synthetic example  10-2. Synthesis of [intermediate 10-b]

                                   [Intermediate 10-b]

Except that phenylboronic acid was used in place of the dibenzofuran-1-boronic acid used in Synthesis Example 1-1 and [Intermediate 10-a] was used instead of methyl-5-bromo-2-iodobenzoate To give [intermediate 10-b]. (Yield: 75%)

Synthetic example  10-3. [Synthesis of intermediate 10-c]

                                       [Intermediate 10-c]

The procedure of Intermediate 10-b was repeated except that 4-aminobiphenyl was used in place of [Intermediate 4-a] used in Synthesis Example 4-2 and [Intermediate 10-b] was used instead of 4-bromobiphenyl. c]. (Yield: 54%)

Synthetic example  10-4. [compound 183]  synthesis

                                                [Compound 183]

Was synthesized in the same manner as in Synthesis Example 9-9, except that [Intermediate 10-c] was used in place of the bis (4-biphenyl) amine used in Synthesis Example 9-9 to obtain [Compound 183]. (Yield 67%)

MS (MALDI-TOF): m / z 755.32 [M] ^&lt; ^{+ &}

Synthetic example  11. [Compound 238]  synthesis

Synthetic example  11-1. Synthesis of [intermediate 11-a]

[Intermediate 11-a]

Was synthesized in the same manner as in Synthesis Examples 1-2 to 1-3 using 3 M-ethyl magnesium bromide instead of 3 M-methyl magnesium bromide used in Synthesis Example 1-2 to obtain [Intermediate 11-a]. (Yield 67%)

Synthetic example  11-2. [compound 238]  synthesis

Except that bis (3-biphenyl) amine was used in place of the bis (4-biphenyl) amine used in Synthesis Example 1-4 and [Intermediate 11-a] was used in place of [Intermediate 1-c] To obtain [Compound 238]. (Yield: 75%)

MS (MALDI-TOF): m / z 631.29 [M] ^&lt; ^{+ &}

Synthetic example  12. [Compound 254]  synthesis

Synthetic example  12-1. Synthesis of [intermediate 12-a]

[Intermediate 12-a]

Synthesis was conducted in the same manner as in Synthesis Examples 3-1 to 3-6 except that 2-bromo-9,9-diethylfluorene was used instead of 2-bromo-9,9-dimethylfluorene used in Synthesis Example 3-1. To obtain [intermediate 12-a]. (70% yield)

Synthetic example  12-2. [compound 254]  synthesis

Except that N-phenyl-4-biphenylamine was used in place of the bis (4-biphenyl) amine used in Synthesis Example 1-4 and [Intermediate 12-a] was used in place of [Intermediate 1-c] To obtain [Compound 254]. (Yield: 75%)

MS (MALDI-TOF): m / z 555.26 [M] ^&lt; ^{+ &}

Synthetic example  13. [Compound 262]  synthesis

Synthetic example  13-1. Synthesis of [intermediate 13-a]

[Intermediate 13-a]

Synthesis was conducted in the same manner as in Synthesis Examples 5-2 to 5-4, except that 2,4-dimethyl-3-pentanone used in Synthesis Example 5-2 was used instead of acetone to obtain [Intermediate 13-a]. (Yield 50%)

Synthetic example  13-2. [compound 262]  synthesis

Except that 4-methyldiphenylamine was used in place of the bis (4-biphenyl) amine used in Synthesis Example 1-4 and [Intermediate 13-a] was used instead of [Intermediate 1-c] Compound 262]. (Yield: 72%)

MS (MALDI-TOF): m / z 610.30 [M] ^&lt; ^{+ &}

Synthetic example  14. [Compound 268]  synthesis

Synthetic example  14-1. Synthesis of [intermediate 14-a]

[Intermediate 14-a]

Except that 3 M-ethyl magnesium bromide was used instead of 3 M-methyl magnesium bromide used in Synthesis Example 1-2 and [Intermediate 9-d] was used instead of [Intermediate 1-a], Synthesis Examples 9-6 to 9-8 and Synthesis was conducted in the same manner as in [Intermediate 14-a]. (Yield: 55%)

Synthetic example  14-2. [compound 268]  synthesis

(4-biphenyl) - (9,9-dimethylfluoren-2-yl) amine was used instead of the bis (4-biphenyl) [Compound 268] was obtained by the same method as Intermediate 14-a except for using [Intermediate 14-a]. (Yield: 74%)

MS (MALDI-TOF): m / z 671.32 [M] ^&lt; ^{+ &}

Synthesis Example 15. Synthesis of [Compound 317]

Synthetic example  15-1. Synthesis of [intermediate 15-a]

[Intermediate 15-a]

Except that 1-bromo-2-iodo-3-fluorobenzene was used in place of 1-bromo-3-chloro-2-fluorobenzene used in Synthesis Example 3-4 Synthesis was conducted in the same manner as Intermediate 3-f to give [Intermediate 15-a]. (Yield: 52%)

Synthesis Example 15-2. Synthesis of [Compound 317]

Except that N-phenyl-4-biphenylamine was used in place of the bis (4-biphenyl) amine used in Synthesis Example 1-4 and [Intermediate 15-a] was used instead of [Intermediate 1-c] To obtain [Compound 317]. (Yield: 74%)

MS (MALDI-TOF): m / z 671.32 [M] ^&lt; ^{+ &}

Synthesis Example 16. Synthesis of [Compound 321]

Synthetic example  16-1. Synthesis of [intermediate 16-a]

                     [Intermediate 16-a]

50 g (235 mmol) of 1-fluoro-9,9'-dimethylfluorene was added to a round-bottomed flask, 500 ml of tetrahydrofuran was added under nitrogen atmosphere, the temperature was lowered to -78 ° C., and 161 ml 259 mmol) is slowly added dropwise. The temperature was raised to room temperature and stirred for 4 hours. Thereafter, the temperature was further lowered to -78 ° C., trimellitic borate (32 ml, 282 mmol) was slowly added while keeping the temperature at low temperature, and the temperature was raised to room temperature and stirred. After completion of the reaction, the organic layer was concentrated under reduced pressure and recrystallized from hexane to obtain 45 g (yield 75%) of [Intermediate 16-a].

Synthetic example  16-2. [Synthesis of intermediate 16-b]

[Intermediate 16-b]

Except that 1-bromo-2-iodo-3-fluorobenzene was used in place of 1-bromo-3-chloro-2-fluorobenzene used in Synthesis Example 3-4 Synthesis was conducted in the same manner as Intermediate 3-f to give [Intermediate 16-b]. (Yield 50%)

Synthesis Example 16-3. Synthesis of [Compound 321]

Except that N-phenyl-4-biphenylamine was used in place of the bis (4-biphenyl) amine used in Synthesis Example 1-4 and [Intermediate 16-b] was used in place of [Intermediate 1-c] To obtain [Compound 321]. (Yield: 71%)

Synthesis Example 17. Synthesis of [Compound 325]

Synthetic example  17-1. Synthesis of [intermediate 17-a]

[Intermediate 17-a]

Dibenzofuran-3-boronic acid was used instead of dibenzofuran-1-boronic acid used in Synthesis Example 1-1, methyl-2-bromobenzoate Were used to synthesize [Intermediate 17-a] in the same manner as Synthesis Examples 1-1 to 1-3. (70% yield)

Synthetic example  17-2. [Synthesis of intermediate 17-b]

[Intermediate 17-b]

[Intermediate 17-b] was obtained in the same manner except that [Intermediate 17-a] was used instead of 1-fluoro-9,9'-dimethylfluorene used in Synthesis Example 16-1. (Yield: 74%)

Synthesis Example 17-3. Synthesis of [Compound 325]

Except that N-phenyl-4-biphenylamine was used in place of the bis (4-biphenyl) amine used in Synthesis Example 1-4 and [Intermediate 17-b] was used in place of [Intermediate 1-c] To obtain [Compound 325]. (Yield: 71%)

Example  1 to 17: Preparation of organic light emitting diode

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber and the base pressure was adjusted to ¹ × 10 ^-6 torr, an organic material was deposited on the ITO using HATCN (50 Å) as a hole transport layer, the compound (650 Å) Doped with a host (BH) + blue dopant (BD) of 5% to form a 200 Å thick light emitting layer. Thereafter, the compound ET: Liq = 1: 1 (300 ANGSTROM), the electron injecting layer Liq (10 ANGSTROM) and Al (1,000 ANGSTROM) were sequentially deposited as the electron transporting layer.

The structures of [HATCN], [BH], [BD], [ET], and [Liq] are as follows.

[HATCN] [BH] [BD]

    [ET] [Liq]

Comparative Example  One

The organic light-emitting diode device for Comparative Example 1 was fabricated in the same manner as in Example 1 except that NPD, which is widely used as a hole transport layer material in the prior art, was used instead of the compound prepared by the present invention .

[NPD]

The voltage, luminance, color coordinates, and lifetime of the organic EL device manufactured according to Examples 1 to 17 and Comparative Example 1 were measured, and the results are shown in Table 1 below.

Here, T95 represents the time required for the luminance to be reduced to 95% of the initial luminance (2000 cd / m ² )

division HTL V Cd / A CIEx CIEy T ₉₅ (Hrs) Comparative Example 1 NPD 4.2 6.3 0.133 0.129 13 Example 1 Formula 1 3.6 8.0 0.132 0.130 35 Example 2 (3) 3.7 7.8 0.133 0.128 33 Example 3 (67) 3.4 8.0 0.132 0.126 34 Example 4 68 3.6 7.9 0.133 0.125 37 Example 5 Formula 111 3.8 8.0 0.133 0.125 43 Example 6 120 3.7 7.9 0.132 0.126 40 Example 7 136 3.7 7.8 0.132 0.130 34 Example 8 Formula 141 3.5 7.7 0.133 0.128 34 Example 9 181 3.6 8.1 0.133 0.125 40 Example 10 183 4.0 7.8 0.132 0.129 35 Example 11 238 3.8 7.7 0.132 0.130 35 Example 12 254 3.6 7.7 0.133 0.130 38 Example 13 262 3.7 7.8 0.133 0.128 36 Example 14 268 3.6 7.9 0.132 0.129 40 Example 15 317 3.6 7.8 0.133 0.126 60 Example 16 321 3.7 7.9 0.132 0.129 55 Example 17 324 3.6 8.0 0.133 0.125 56

As shown in Table 1, the organic compound obtained according to the present invention has higher efficiency, lower driving voltage and longer lifetime than NPD, which is widely used as a hole transport layer material, It can be used for the production of

In addition, among Examples 1 to 17, Examples 15 to 17 have improved long life characteristics than those of the other Examples.

Comparative Example 2: Production of organic light emitting diode

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber, the substrate was adjusted to have a pressure of 1 × 10 ^-6 torr. Then, HATCN (50 Å), NPD (900 Å) host CBP and green phosphorescent dopant (GD) 7% to form a 300 Å thick luminescent layer. The films were deposited in the order of ET: Liq = 1: 1 (300 Å), Liq (10 Å), and Al (1,000 Å).

[HATCN] [NPD] [CBP]

[ET] [Liq] [GD]

Comparative Example 3

An organic electroluminescent device was fabricated according to a conventional method using Comparative Compound 1 as a hole-assisted layer material. First, the ITO glass was patterned to have a light emitting area of 2 mm x 2 mm, and then cleaned. After the substrate was mounted in a vacuum chamber, the substrate was adjusted to have a pressure of 1 × 10 ^-6 torr. Then, HATCN (50 Å) and NPD (550 Å) were formed on the ITO and Comparative Organic Compound 1 (350 Å) After forming, the host used CBP and the green phosphorescent dopant (GD) was doped with 7% to form a 300 Å thick luminescent layer. The films were deposited in the order of ET: Liq = 1: 1 (300 Å), Liq (10 Å), and Al (1,000 Å).

[Comparative Compound 1]

Example  18 to 23

An organic electroluminescent device was fabricated in the same manner as in Comparative Example 2, except that the compound of the present invention was used instead of the comparative compound 1 as the hole-assisted layer material.

division Hole assist layer V Cd / A CIEx CIEy T ₉₅ (Hrs) Comparative Example 2 - 6.9 36 0.335 0.625 20 Comparative Example 3 Comparative compound 1 6.9 42 0.329 0.631 25 Example 18 (67) 6.9 51 0.327 0.632 41 Example 19 Formula 111 6.8 49 0.330 0.631 45 Example 20 181 7.0 50 0.337 0.625 43 Example 21 317 6.9 52 0.329 0.631 71 Example 22 321 6.8 53 0.327 0.632 65 Example 23 324 6.9 51 0.329 0.631 68

As shown in Table 2, when the organic compound obtained according to the present invention is used as a hole-assisted layer, it can be seen that it has higher efficiency and longer life than Comparative Examples 2 to 3. Thus, It can be used for manufacturing a light emitting device.

In addition, among Examples 18 to 23 among Examples, Examples 21 to 23 have more improved long life characteristics than the other Examples.

Claims (13)

An organic compound represented by any one of the following formulas (A) to (E).
(A)

[Chemical Formula B]

&Lt; RTI ID = 0.0 &

[Chemical Formula D]

(E)

In the above formulas (A) to (E)
X1 is CR &lt; 11 &gt; or N,
X2 is CR12 or N,
X3 is CR13 or N,
X4 is CR14 or N,
X5 is CR &lt; 15 &gt; or N,
X6 is CR16 or N,
X7 is CR &lt; 17 &gt; or N,
X8 is CR &lt; 18 &gt; or N,
X9 is CR &lt; 19 &gt; or N,
X10 is CR &lt; 20 &gt; or N,
At least two of X1 to X4 are selected from CR11 to CR14,
At least three of X5 to X10 are selected from CR15 to CR20,
Wherein one of X1 to X10 represents a carbon atom bonded to the A1

),
Substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C2-C30 alkenyl group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C2-C30 alkenyl group, A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6- A substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon number of 6 A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, A substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, An amide group, an ether group and an ester group,
The linking group L 1 is a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, And a substituted heteroarylene group having 2 to 60 carbon atoms,
n is an integer of 0 to 3, and when each of these is 2 or more, each of the linking groups L1 is the same or different from each other,
The substituents Ar1 and Ar2 are the same or different from each other and are each independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms or substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms,
Ar1 and L1 in A1 may be connected to each other to form a condensed ring, Ar2 and L1 may be connected to each other to form a condensed ring,
The 'substituted' in the 'substituted or unsubstituted' refers to a group selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, An alkenyl group, an alkynyl group having 2 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 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, An alkyl group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 6 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, An aryloxy group, an aryloxy group, an arylsilyl group, and an aryloxy group having 6 to 24 carbon atoms. The method according to claim 1,
Wherein Ar 1 and Ar 2 are the same or different and independently of each other, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. The method according to claim 1,
The substituent R11 to R20 in the above formulas (A) to (E) is hydrogen or deuterium. The method according to claim 1,
Wherein the linking group L1 in the above formulas (A) to (E) is a single bond or any one selected from the following structural formulas (1) to (9).
[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]

In the structural formulas 1 to 9, the carbon of the aromatic ring is bonded to hydrogen or deuterium. The method according to claim 1,
In the above formulas (A) to (E), n is an integer of 1 or 2, and when n is 2, each of the linking groups L1 is the same or different from each other. The method according to claim 1,
Lt; RTI ID = 0.0 &gt; X1 &lt; / RTI &gt; to 10 are nitrogen atoms or not all are nitrogen atoms. The method according to claim 1,
Wherein the compound represented by any one of the above Chemical Formulas A to E is selected from the following compounds represented by the following Chemical Formulas 1 to 328:

<Compound 1><Compound2><Compound3><Compound4>

&Lt; Compound 5 >< Compound 6 >< Compound 7 >< Compound 8 &

&Lt; Compound 9 >< Compound 10 >< Compound 11 &

&Lt; Compound 13 >< Compound 14 >< Compound 15 >< Compound 16 &

&Lt; Compound 17 >< Compound 18 >< Compound 19 &

&Lt; Compound 21 >< Compound 22 >< Compound 23 &

<Compound 25><Compound26><Compound27><Compound28>

&Lt; Compound 29 >< Compound 30 >< Compound 31 &

<Compound 33><Compound34><Compound35><Compound36>

&Lt; Compound 37 >< Compound 38 >< Compound 39 &

&Lt; Compound 41 >< Compound 42 >< Compound 43 &

<Compound 45><Compound46><Compound47><Compound48>

&Lt; Compound 49 >< Compound 50 >< Compound 51 &

<Compound 53><Compound54><Compound55><Compound56>

&Lt; Compound 57 >< Compound 58 >< Compound 59 >< Compound 60 &

&Lt; Compound 61 >< Compound 62 >< Compound 63 >< Compound 64 &

<Compound 65><Compound66><Compound67><Compound68>

&Lt; Compound 69 >< Compound 70 >< Compound 71 >< Compound 72 &

<Compound 73><Compound74><Compound75><Compound76>

&Lt; Compound 77 >< Compound 78 >< Compound 79 >< Compound 80 &

<Compound 81><Compound82><Compound83><Compound84>

&Lt; Compound 85 >< Compound 86 >< Compound 87 >< Compound 88 &

&Lt; Compound 89 >< Compound 90 > Compound 91 &gt;&lt; Compound 92 &

<Compound 93><Compound94><Compound95><Compound96>

&Lt; Compound 97 &gt;&lt; Compound 98 >< Compound 99 >< Compound 100 &

&Lt; Compound 101 >< Compound 102 >< Compound 103 >< Compound 104 &

<Compound 105><Compound106><Compound107><Compound108>

&Lt; Compound 109 >< Compound 110 >< Compound 111 &

<Compound 113><Compound114><Compound115><Compound116>

&Lt; Compound 117 >< Compound 118 >< Compound 119 &

<Compound 121><Compound122><Compound123><Compound124>

<Compound 125><Compound126><Compound127><Compound128>

&Lt; Compound 129 >< Compound 130 >< Compound 131 &

<Compound 133><Compound134><Compound135><Compound136>

&Lt; Compound 137 >< Compound 138 >< Compound 139 &

<Compound 141><Compound142><Compound143><Compound144>

<Compound 145><Compound146><Compound147><Compound148>

<Compound 149><Compound150><Compound151><Compound152>

<Compound 153><Compound154><Compound155><Compound156>

<Compound 157><Compound158><Compound159><Compound160>

<Compound 161><Compound162><Compound163><Compound164>

<Compound 165><Compound166><Compound167><Compound168>

<Compound 169><Compound170><Compound171><Compound172>

<Compound 173><Compound174><Compound175><Compound176>

<Compound 177><Compound178><Compound179><Compound180>

<Compound 181><Compound182><Compound183><Compound184>

<Compound 185><Compound186><Compound187><Compound188>

<Compound 189><Compound190><Compound191><Compound192>

<Compound 193><Compound194><Compound195><Compound196>

<Compound 197><Compound198><Compound199><Compound200>

<Compound 201><Compound202><Compound203><Compound204>

<Compound 205> <Compound 206><Compound207><Compound208>

<Compound 209><Compound210><Compound211><Compound212>

<Compound 213><Compound214><Compound215><Compound216>

<Compound 217><Compound218><Compound219><Compound220>

&Lt; Compound 221 >< Compound 222 >< Compound 223 &

<Compound 225><Compound226><Compound227><Compound228>

<Compound 229><Compound230><Compound231><Compound232>

<Compound 233><Compound234><Compound235><Compound236>

&Lt; Compound 237 >< Compound 238 >< Compound 239 >< Compound 240 &

<Compound 241><Compound242><Compound243><Compound244>

<Compound 245><Compound246><Compound247><Compound248>

<Compound 249><Compound250><Compound251><Compound252>

<Compound 253><Compound254><Compound255><Compound256>

<Compound 257><Compound258><Compound259><Compound260>

<Compound 261><Compound262><Compound263><Compound264>

<Compound 265><Compound266><Compound267><Compound268>

<Compound 269><Compound270><Compound271><Compound272>

<Compound 273><Compound274><Compound275><Compound276>

<Compound 277><Compound278><Compound279><Compound280>

<Compound 281><Compound282><Compound283><Compound284>

<Compound 285><Compound286><Compound287><Compound288>

<Compound 289><Compound290><Compound291><Compound292>

<Compound 293><Compound294><Compound295><Compound296>

<Compound 297><Compound298><Compound299><Compound300>

<Compound 301><Compound302><Compound303><Compound304>

<Compound 305><Compound306><Compound307><Compound308>

<Compound 309><Compound310><Compound311><Compound312>

<Compound 313><Compound314><Compound315><Compound316>

&Lt; Compound 317 >< Compound 318 >< Compound 319 >< Compound 320 &

<Compound 321><Compound322><Compound323><Compound324>

<Compound 325><Compound326><Compound327><Compound328> The method according to claim 1,
The organic compound represented by any one of the above formulas (A) to (E) is a compound wherein A1 is bonded to the 1-position of the dibenzofuran moiety,
In formula (A), A1 is bonded to the carbon of X6, in formula (B), A1 is bonded to the carbon of X7, in formula (C), A1 is bonded to the carbon of X9, Lt; RTI ID = 0.0 &gt; X5. &Lt; / RTI &gt; A first electrode;
A second electrode facing the first electrode; And
And an organic layer interposed between the first electrode and the second electrode,
Wherein the organic layer comprises an organic compound according to any one of claims 1 to 8. 10. The method of claim 9,
Wherein the organic light emitting device comprises at least one of a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, a light emitting layer, an electron transporting layer, and an electron injecting layer. 10. The method of claim 9,
Wherein the organic compound is used for a hole transport layer. 11. The method of claim 10,
Wherein at least one layer selected from the respective layers is formed by a deposition process or a solution process. 10. The method of claim 9,
The organic light emitting device includes a flat panel display device; A flexible display device; Monochrome or white flat panel illumination devices; And a device for flexible illumination of a single color or a white color.

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