KR101938826B1 - Novel heterocyclic compounds and organic light-emitting diode including the same - Google Patents

Abstract

The present invention relates to a heterocyclic compound having an amine group represented by any one of the formulas (A) to (C), and an organic light emitting device comprising the same. Are the same as those defined in the detailed description.

Description

TECHNICAL FIELD The present invention relates to a novel heterocyclic compound and an organic light emitting device including the heterocyclic compound and an organic light emitting diode including the same.

The present invention relates to a novel heterocyclic compound and an organic light emitting device including the same, and more particularly, to a heterocyclic compound that can be used in a light emitting layer of an organic light emitting device and an organic light emitting device including the same.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween.

Here, in order to enhance the efficiency and stability of the organic light emitting diode OLED, the organic material layer may have a multi-layer structure composed of different materials. For example, the organic layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, have.

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.

On the other hand, when only one material is used as the light emitting material, there arises a problem that the maximum light emitting wavelength shifts to a long wavelength due to intermolecular interaction, the color purity drops, or the efficiency of the device decreases due to the light emission attenuating effect. A host-dopant system can be used as a light emitting material to increase the efficiency of light emission through the transition.

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

When current is applied to the organic light emitting device, holes and electrons are injected from the anode and the cathode, respectively, and injected holes and electrons recombine in the light emitting layer through the respective hole transporting layers and electron transporting layers to form luminescent excitons. The luminescent excitons thus formed emit light while transitioning to the ground state. The light may be divided into fluorescence using a singlet exciton and phosphorescent triplet exciton according to a light emitting mechanism, and the fluorescence and phosphorescence may be used as a light source of an organic light emitting device.

On the other hand, fluorescence using only singlet excitons has a limit of luminous efficiency because the probability of occurrence of singlet excitons is 25%, while phosphorescence using triplet excitons is superior to fluorescence in many cases Is continuing.

As the host material of the phosphorescent light emitting material, CBP is the most widely known, and an organic light emitting device using a hole blocking layer such as BCP and BAlq is known.

However, in the case of a conventional material such as BAlq or CBP used as a host of a phosphorescent material, a device using a conventional phosphorescent material has a higher driving voltage than a device using a fluorescent material, There is no significant advantage in terms of power efficiency (lm / w), and it is disadvantageous in terms of life span.

 As a conventional technique using such a phosphorescent material, Japanese Unexamined Patent Application Publication No. 10-2011-0013220 (Mar. 2, 2011) discloses an organic compound in which an aromatic heterocycle is introduced into the skeleton of a 6-membered aromatic ring or a 6-membered heteroaromatic ring And JP-A-2010-166070 (2010.7.29) discloses an organic compound in which an aryl or heteroaryl ring is bonded to a substituted or unsubstituted pyrimidine or quinazoline skeleton.

Also, in order to produce an organic compound having excellent electron transporting ability and hole blocking ability, excellent light emitting efficiency and high stability in a thin film state, in Patent Publication No. 10-2012-0104204 (2012.09.20), a substituted anthracene ring And an organic compound in which a pyridoindole derivative is bonded to the structure.

However, in spite of efforts to manufacture the light emitting material for the organic light emitting device, there is a continuing need to develop a light emitting material capable of driving at a low voltage.

Japanese Patent Application Laid-Open No. 10-2011-0013220 (Feb., 2011)

Japanese Unexamined Patent Publication No. 2002-166070 (2010.7.29)

Japanese Patent Application Laid-Open No. 10-2012-0104204 (2012.09.20)

Accordingly, a first technical object of the present invention is to provide a novel novel heterocyclic compound which can be used in a light emitting layer of an organic light emitting device and has low voltage driving characteristics.

A second object of the present invention is to provide an organic light emitting device including the organic compound.

In order to achieve the first technical object, the present invention provides a heterocyclic compound having an amine group represented by any one of the following formulas (A) to (C).

(A)

[Chemical Formula B]

≪ RTI ID = 0.0 &

In the above formulas (A) to (C)

A1, A2, E and F are the same or different and each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 40 carbon atoms;

Two carbon atoms adjacent to each other in the aromatic ring of A1 and two carbon atoms adjacent to each other in the aromatic ring of A2 form a condensed ring by forming a 5-membered ring with carbon atoms connected to the substituents R1 and R2;

The linking groups L1 to L10 are the same or different from each other and each independently represents a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkinylene group having 2 to 60 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted arylene group having 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, A substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;

M is any one selected from NR ₃ , CR ₄ R ₅ , SiR ₆ R ₇ , GeR ₈ R ₉ , O, S, Se;

Substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, A substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, , A substituted or unsubstituted C2-C50 hetero aryl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6- 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 carbon A substituted or unsubstituted arylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, A substituted or unsubstituted C1 to C30 alkyl germanium group, a substituted or unsubstituted C6 to C30 aryl germanium group, a cyano group, a nitro group, and a halogen group,

The carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring may be one of N, O, P, Si, S, Ge , Se, and Te;

The substituent HA is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,

Each of p1 to p3, r1 to r3, s1 to s3 and q is the same or different and independently of one another is an integer of 1 to 3, and when each of these is 2 or more, each of the linking groups L1 to L10 is the same or different from each other ,

X, y and z are the same or different and independently of one another an integer of 0 to 3,

Ar1 and Ar2, Ar3 and Ar4, and Ar5 and Ar6 may be linked to each other to form a ring;

In the formula (A) and the formula (B), two carbon atoms adjacent to each other in the A2 ring are bonded to * of the formula Q1 to form a condensed ring, x + y is 1 or more,

In the formula (C), two carbon atoms adjacent to each other in the A1 ring are bonded to * in the formula Q2 to form a condensed ring, and two carbon atoms adjacent to each other in the A2 ring are bonded to * in the formula Q1, And x + y + z is 1 or more.

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, An organic light emitting device comprising at least one heterocyclic compound having the amine group of the present invention is provided.

The heterocyclic compound according to the present invention has low-voltage driving characteristics when used as a material for a phosphorescent host, and can be used for the production of stable and excellent devices.

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 present invention provides a heterocyclic compound having an amine group which can be used in a light emitting layer of an organic light emitting device, and which is represented by any one of the following formulas (A) to (C).

(A)

[Chemical Formula B]

≪ RTI ID = 0.0 &

In the above formulas (A) to (C)

A1, A2, E and F are the same or different and each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 40 carbon atoms;

Two carbon atoms adjacent to each other in the aromatic ring of A1 and two carbon atoms adjacent to each other in the aromatic ring of A2 form a condensed ring by forming a 5-membered ring with carbon atoms connected to the substituents R1 and R2;

The linking groups L1 to L10 are the same or different from each other and each independently represents a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkinylene group having 2 to 60 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted arylene group having 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, A substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;

M is any one selected from NR ₃ , CR ₄ R ₅ , SiR ₆ R ₇ , GeR ₈ R ₉ , O, S, Se;

Substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, A substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, , A substituted or unsubstituted C2-C50 hetero aryl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6- 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 carbon A substituted or unsubstituted arylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, A substituted or unsubstituted C1 to C30 alkyl germanium group, a substituted or unsubstituted C6 to C30 aryl germanium group, a cyano group, a nitro group, and a halogen group,

The carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring may be one of N, O, P, Si, S, Ge , Se, and Te;

The substituent HA is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,

Each of p1 to p3, r1 to r3, s1 to s3 and q is the same or different and independently of one another is an integer of 1 to 3, and when each of these is 2 or more, each of the linking groups L1 to L10 is the same or different from each other ,

X, y and z are the same or different and independently of one another an integer of 0 to 3,

Ar1 and Ar2, Ar3 and Ar4, and Ar5 and Ar6 may be linked to each other to form a ring;

In the formula (A) and the formula (B), two carbon atoms adjacent to each other in the A2 ring are bonded to * of the formula Q1 to form a condensed ring, x + y is 1 or more,

In the formula (C), two carbon atoms adjacent to each other in the A1 ring are bonded to * in the formula Q2 to form a condensed ring, and two carbon atoms adjacent to each other in the A2 ring are bonded to * in the formula Q1, And x + y + z is 1 or more,

Here, the 'substitution' in the 'substituted or unsubstituted' in the above Chemical Formulas A to C is a substituent selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 24 carbon atoms, An alkyl group having 2 to 24 carbon atoms, 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 Or a heteroaryl group having 2 to 24 carbon atoms, an alkoxy 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, A silyl group, an arylsilyl group having 6 to 24 carbon atoms, 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 24 carbon atoms" and "substituted or unsubstituted aryl group having 6 to 24 carbon atoms" in the present invention, The carbon number of the alkyl group having 1 to 24 carbon atoms and the aryl group having 6 to 24 carbon atoms means the total number of carbon atoms constituting the alkyl moiety or 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.

In addition, the aryl group used in the compound of the present invention includes 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 include phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, crycenyl, naphthacenyl, fluororan And the like, but are not limited thereto.

At least one of the hydrogen atoms of the aryl group may be substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a silyl group, an amino group (-NH2, -NH (R) 'And R' 'each independently represent 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, A halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, A heteroaryl group having 2 to 24 carbon atoms or a heteroarylalkyl group having 2 to 24 carbon atoms.

The heteroaryl group which is a substituent used in the compound of the present invention is a heteroaryl group having 2 to 6 carbon atoms which may contain 1 to 4 hetero atoms selected from N, O, P, Se, Te, Si, Ge or S in each ring in the aryl group. Quot; means a heteroaromatic radical of from 2 to 24 carbon atoms, 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.

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, iso-amyloxy, 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.

In the formula (A), the substituent HA or the linking group L10 is bonded to the A2 ring when the formula Q1 is connected to the A2 ring, and the x Or y has one or more structural features, wherein in the formula B, the substituent HA or the linking group L10 is always bonded to the A1 ring when the structural formula Q1 is connected to the A2 ring, and one of x or y is one or more structural features , And the substituent HA or the linking group L10 is always bonded to the A2 ring when the formula Q2 is connected to the A1 ring in the formula C and the formula Q1 is connected to the A2 ring, and at least one of x, y or z is 1 Or more.

In the present invention, A ₁ , A ₂ , E and F are the same or different and independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms in Formulas A to C, respectively.

As described above, when A ₁ , A ₂ , E and F in the formulas (A) to (C) are the same or different and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, The substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms may be the same or different and independently selected from [Structural Formula 10] to [Structural Formula 21].

[Structural formula 10] [Structural formula 11] [Structural formula 12]

[Structural Formula 13] [Structural Formula 14] [Structural Formula 15]

[Structural formula 16] [Structural formula 17] [Structural formula 18]

[Structural formula 19] [Structural formula 20] [Structural formula 21]

In the above structural formulas 10 to 21, "- *" represents a 5-membered ring containing carbon atoms connected to the substituents R ₁ and R ₂ , or a 5-membered ring containing M in the structural formulas Q ₁ and Q ₂ Means a binding site for forming a circular ring,

When the aromatic hydrocarbon rings of the above-mentioned structural formulas 10 to 21 are bonded to the structural formula Q ₁ or the structural formula Q ₂ corresponding to the A ₁ ring or the A ₂ ring, two adjacent carbon atoms of the structural formula Q ₁ Lt; / RTI > of formula Q < ₂ > or in combination with * of formula Q2 to form a condensed ring;

In the above Structural Formulas 10 to 21, R is the same as R ₁ and R ₂ defined above, m is an integer of 1 to 8, and when m is 2 or more, or when R is 2 or more, each R is They may be the same or different.

In the present invention, the linking groups L ₁ to L ₁₀ in the above-mentioned Formulas A to C are the same or different and each is a single bond or any one selected from the following Structural Formulas 22 to 30.

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

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

[Structural Formula 30]

The carbon position of the aromatic ring in the linking group may be bonded with hydrogen or deuterium.

In the present invention, the substituent HA in the formulas (A) to (C) may be a substituted or unsubstituted heteroaryl group containing a heteroatom selected from O, S and N having 2 to 30 carbon atoms. In this case, Or an unsubstituted heteroaryl group '(HA) containing a hetero atom selected from O, S and N having 2 to 30 carbon atoms may be any one selected from the following structural formulas A to O.

[Structural formula A] [Structural formula B] [Structural formula C]

[Structural formula D] [Structural formula E] [Structural formula F]

[Structural formula G] [Structural formula H] [Structural formula I]

[Structural formula J] [Structural formula K] [Structural formula L]

[Structural formula M] [Structural formula N] [Structural formula O]

The substituents R in the structural formulas A to O are the same as those of R1 to R9 defined above, and n is an integer of 1 to 7. When n is 2 or more, each R is the same or different, and when n is 2 or more Each substituent R may be bonded to adjacent substituent R to form a saturated or unsaturated ring.

In a preferred embodiment of the present invention, x and y in the above Formulas A to C may be 1, respectively.

Meanwhile, specific examples of the heterocyclic compound having an amine group represented by any one of the above formulas (A) to (C) according to the present invention include compounds represented by any one of the following formulas (101) to But is not limited thereto.

<Formula 101> <Formula 102> <Formula 103>

&Lt; EMI ID = 106.1 >

<Formula 107> <Formula 108> <Formula 109>

&Lt; Formula 110 > < EMI ID =

<Formula 113> <Formula 114> <Formula 115>

&Lt; EMI ID = 116.1 >

&Lt; EMI ID = 120.1 >

&Lt; Formula 122 > < EMI ID =

<Formula 125> Formula 126> Formula 127>

&Lt; Formula 128 > < EMI ID = 129.0 >

&Lt; Formula 131 > < EMI ID =

&Lt; Formula 134 > < EMI ID =

&Lt; Formula 137 > < EMI ID = 139.0 >

&Lt; Formula 140 > < EMI ID =

&Lt; Formula 143 > < EMI ID =

&Lt; Formula 146 > < EMI ID =

<Formula 149> <Formula 150>

<Formula 152> <Formula 153>

<Formula 155> <Formula 156> <Formula 157>

&Lt; Formula 15 > < EMI ID =

<Formula 161> <Formula 162> <Formula 163>

<Formula 164> <Formula 165> <Formula 166>

&Lt; Formula 167 > < EMI ID =

&Lt; Formula 170 > < EMI ID =

&Lt; Formula 173 > < EMI ID =

&Lt; Formula 176 > < EMI ID =

&Lt; Formula 179 > < EMI ID =

&Lt; Formula 182 > < EMI ID =

&Lt; Formula 186 > < EMI ID =

<Formula 188> <Formula 189> <Formula 190>

<Formula 191> <Formula 192> <Formula 193>

&Lt; Formula 194 > < EMI ID =

&Lt; Formula 197 > < EMI ID =

&Lt; Formula 200 > < EMI ID =

&Lt; Formula 203 > < EMI ID =

<Formula 206> <Formula 207>

&Lt; Formula 210 > < EMI ID =

<Formula 212> <Formula 213> <Formula 214>

&Lt; Formula 215 >

<Formula 218> <Formula 219> <Formula 220>

&Lt; Formula 221 > < EMI ID =

<Formula 224> <Formula 225> <Formula 226>

&Lt; Formula 228 > < EMI ID =

&Lt; Formula 230 > < EMI ID =

<Formula 233> <Formula 234> <Formula 235>

<Formula 236> <Formula 237> <Formula 238>

&Lt; Formula 239 > < EMI ID =

&Lt; EMI ID = 242 >

<245> <Formula 246> <Formula 247>

&Lt; Formula 248 > < EMI ID =

[Formula 252] < EMI ID =

&Lt; Formula 254 > < EMI ID =

&Lt; Formula 257 > < EMI ID =

<Formula 260> <Formula 262> <Formula 262>

&Lt; Formula 263 > < EMI ID =

&Lt; Formula 266 > < EMI ID =

&Lt; EMI ID = 31.1 >

&Lt; EMI ID = 272 >

(277) < EMI ID = 275.1 >

&Lt; EMI ID = 278 >

&Lt; Formula 281 > < EMI ID =

&Lt; Formula 284 >

&Lt; Formula 288 > < EMI ID =

&Lt; EMI ID = 290 >

&Lt; Formula 293 > < EMI ID =

&Lt; EMI ID = 298 >

&Lt; Formula 300 > < EMI ID =

&Lt; Formula 302 > < EMI ID =

&Lt; Formula 305 > < EMI ID =

&Lt; Formula 308 > < EMI ID =

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 comprises at least one heterocyclic compound having the amine group in the present invention.

In the present invention, the phrase " (organic layer) contains at least one organic compound " means that one organic compound belonging to the category of the present invention (organic layer) or two or more different compounds belonging to the category of organic compound May be included.

The organic layer may include at least one of a hole injecting layer, a hole transporting layer, an electron blocking layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. At this time, the organic layer interposed between the first electrode and the second electrode includes a light emitting layer, and the light emitting layer comprises a host and a dopant, and the heterocyclic compound having the amine group in the present invention may be used as a host.

In the present invention, a dopant material may be used for the light emitting layer in addition to the host. When the light emitting layer includes a host and a dopant, the 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.

Meanwhile, when the heterocyclic compound of the present invention is used as a host, the organic layer may further include a hole blocking layer or an electron blocking layer.

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.

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

The material for the hole transport layer is not particularly limited as long as it is commonly used in the art and includes, for example, N, N'-bis (3-methylphenyl) -N, N'- Biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine (a-NPD). However, the present invention is not necessarily limited thereto.

Subsequently, an organic light emitting layer 50 is laminated on the hole transport layer 40, and a hole blocking layer (not shown) is selectively deposited on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method. .

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 a light emitting compound with an electron transporting ability. Typical examples thereof include BAlq, BCP, TPBI, Bphen, TPBI, NTAZ, BeBq ₂ , OXD- Liq and any one selected from the formulas (1001) to (1007) may be used, but the present invention is not limited thereto.

BAlq BCP Bphen

TPBI NTAZ BeBq ₂

OXD-7 Liq

(1001)

 (1004)

1007

The electron transport layer 60 is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method.

In the present invention, as an electron transporting layer material of an organic light emitting device, a known electron transporting material can be used as a material that stably transports electrons injected from an electron injection electrode (cathode). Examples of known electron transport materials include quinoline derivatives, especially tris (8-quinolinolate) aluminum (Alq3), TAZ, BAlq, beryllium bis (benzoquinolin-10- olate: Bebq2), compounds 201 and 202, oxadiazole derivatives PBD, BMD, BND, and the like may be used, but the present invention is not limited thereto.

TAZ < Compound 201 > < Compound 202 >

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

[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 A ligand chelated by coordination bond with the single bond, and

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

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

In 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 alkylamino group having 1 to 30 carbon atoms, an unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms and a substituted or unsubstituted arylsilyl And may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring.

On the other hand, after the electron transport layer is deposited, an electron injection layer 70 is formed by a vacuum evaporation method or a spin coating method, and a metal for forming a cathode is vacuum deposited on the electron injection layer 70 to form a cathode 80 ) Electrode is formed to complete the organic light emitting element. 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.

According to a specific example of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 ANGSTROM. Herein, phosphorescent dopants to be used when the light emitting layer utilizes phosphorescence include compounds represented by the following general formulas (A-1) to (J-1). &Lt; / RTI &gt;

[General Formula A-1]

Wherein M is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, preferably Ir, Pt, Pd, Rh, Re , Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag. The ligands L ₁ , L ₂ and L ₃ are the same or different from each other and independently selected from the following structural formulas D, but are not limited thereto.

In the following structural formula D, &quot; * &quot; represents a site coordinated to the metal ion M. [

[Structural formula D]

Wherein R is different from or the same as each other and is independently selected from the group consisting of hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, Or a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2- A substituted or unsubstituted C1-C30 alkylamino group, a substituted or unsubstituted C1-C30 alkylsilyl group, a substituted or unsubstituted C6-C30 arylamino group, and a substituted or unsubstituted C6- An arylsilyl group having 1 to 30 carbon atoms;

Each R is independently selected from an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cyano group, a halogen group, deuterium and hydrogen Which may be further substituted with one or more substituents;

And R may be connected to each adjacent substituent by alkylene or alkenylene to form a monocyclic ring and a monocyclic or polycyclic aromatic ring;

The L may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring.

As one example, the dopant represented by the above-mentioned [formula A-1] may be any one selected from the following compounds.

[Formula B-1]

In the general formula B-1,

M ^A1 represents the same metal ion as defined in the general formula (A1), also, Y ^{A11, A14} Y, Y and Y ^{A15 A18} each independently represent a carbon atom or a nitrogen atom, Y ^{A12, A13} Y, Y ^A16 and Y ^A17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom or a sulfur atom, and L ^A11 , L ^A12 , L ^A13 and L ^A14 each represent a linking group And Q ^A11 and Q ^A12 represent a partial structure containing an atom bonding to M ^A1 .

Exemplary structures of the compound represented by the general formula B-1 include, but are not limited to, the following.

[Formula C-1]

In the general formula C-1,

M ^B1 eunil represents the same metal ion as defined in bansik ^{A-1, Y B11, Y} B14, Y B15 and Y ^B18 represents a carbon atom or a nitrogen atom, each ^{independently, Y B12, Y B13, Y} B16 and Y ^B17 each independently represent a substituted or unsubstituted carbon atoms, a substituted or unsubstituted nitrogen atom, an oxygen atom, a sulfur atom, a, L ^B11, L ^B12, L ^B13, L ^B14 represents a linking group, Q ^B11, Q ^B12 is M ^Lt ; RTI ID = 0.0 &gt; ^B1 . &^Lt; / RTI &gt;

Exemplary structures of the compound represented by the general formula C-1 include, but are not limited to, the following.

[Formula D-1]

In the general formula D-1,

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

Exemplary structures of the compound represented by the general formula D-1 include, but are not limited to, the following.

[Formula E-1]

In the general formula E-1,

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

Exemplary structures of the compound represented by the general formula E-1 include, but are not limited to, the following.

[Formula F-1]

In the general formula F-1,

M ^E1 represents the same metal ion as defined in Scheme A-1, and J ^E11 and J ^E12 independently represent an atom group necessary for forming a five-membered ring, and G ^E11 , G ^E12 , and G ^E13 And G ^E14 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom, and Y ^E11 , Y ^E12 , Y ^E13 and Y ^E14 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom.

Exemplary structures of the compound represented by the general formula F-1 include, but are not limited to, the following.

[Formula G-1]

In the general formula G-1,

M ^F1 represents the same metal ion as defined in formula A-1,

L ^F11, L ^F12 and L ^F13 represents a linking ^{group, R F11, R F12, R} F13 and R ^F14 represents a substituent, R ^F11 and R ^F12, R ^F12 and R ^F13, R ^F13 and R ^F14 are connected to each other And the ring formed by R ^F1 and R ^F12 , R ^F13 and R ^F14 is a 5-membered ring. And Q ^F11 and Q ^F12 represent a partial structure containing an atom bonding to M ^F1 .

Exemplary structures of the compound represented by the general formula G-1 include, but are not limited to, the following.

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

In the general formula H-1,

R ¹¹ and R ¹² are substituents of alkyl, aryl or heteroaryl; And q11 and q12 may be 0 to 4, preferably 0 to 2, and they may form a fused ring with substituents adjacent to each other.

When q11 and q12 are 2 to 4, plural R11 and R12 are the same or different,

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

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

It is preferable that n ¹ and m ¹ denote the metal complex represented by the general formula H-1 as a neutral complex.

R ²¹ , R ²² , n ² , m ² , q ²² and L ² are the same as R ¹¹ , R ¹² , n ¹ , m ¹ , q ¹² and L ¹ in the general formula H-2, q ²¹ is an integer of 0 to 2, preferably 0.

Wherein R ³¹ , n ³ , m ³ and L ³ are the same as R ¹¹ , n ¹ , m ¹ and L ¹ , q ³¹ is an integer of 0 to 8, 2 is preferable, and 0 is more preferable.

Examples of the specific compounds of the above-mentioned general formulas H-1 to H-3 are as follows, but are not limited thereto.

[Formula I-1]

In the general formula I-1,

Ring A, ring B, ring C, and ring D represent a nitrogen-containing heterocyclic ring which may have a substituent, and the remaining two rings are an aryl ring or heteroaryl which may have a substituent And a condensed ring can be formed by ring A and ring B, ring A and ring C, and / or ring B and ring D, respectively. X ¹ , X ² , X ³ and X ^{4 each} represent a nitrogen atom in which two of the double bonds coordinate to a platinum atom, and the remaining two represent a carbon atom or a nitrogen atom. Q ¹ , Q ² and Q ³ each independently represent a divalent atom (or a bond), but Q ¹ , Q ² and Q ³ do not simultaneously represent a bond. ^{Two of} Z ¹ , Z ² , Z ³ and Z ⁴ represent coordinate bond, and the remaining two represent a covalent bond, an oxygen atom or a sulfur atom.

Examples of the specific compounds of the general formula I-1 include, but are not limited to, the following.

[Formula J-1]

In the general formula J-1,

M represents the same metal ion as defined in the general formula A-1, Ar1 represents a substituted or unsubstituted cyclic structure, and in the two azomethine bonds (-C = N-) bonded to the M, , And nitrogen atoms (N) are respectively bonded to the M and form a three-terminal ligand which is bonded at the 3-position to the M as a whole.

Further, in Ar 1, C represents a carbon atom constituting a ring structure represented by Ar 1. R 1 and R 2 may be the same or different and each represents a substituted or unsubstituted alkyl or aryl group, and L represents a one-dimensional ligand.

In the general formula J-1, M is preferably Pt. The above-mentioned Ar1 is preferably selected from a 5-membered ring, a 6-membered ring and condensed ring group thereof.

Examples of the specific compounds of the general formula J-1 include, but are not limited to, the following.

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

In the present invention, at least one layer selected from the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer and the electron injecting layer may be formed by a single molecular deposition method 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 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.

(Example)

Synthesis Example 1: Synthesis of Compound (101)

Synthesis of Synthesis Example 1- (1): [Intermediate 1-a]

                                  <Intermediate 1-a>

To a 500 mL round bottom flask was added methyl 5-bromo-2-iodobenzoate (25.0 g, 73 mmol), 4-dibenzofuranboronic acid (18.7 g, 88 mmol), tetrakis (triphenylphosphine) palladium (1.7 g, 0.15 mmol) and potassium carbonate (20.2 g, 146.7 mmol), and then 125 mL of toluene, 125 mL of tetrahydrofuran and 50 mL of water were added. The temperature of the reactor was raised to 80 ° C and stirred for 10 hours. When the reaction was completed, the temperature of the reactor was lowered to room temperature, extracted with ethyl acetate, and the organic layer was separated. The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain <Intermediate 1-a>. (75.0 g, 60.1%).

Synthesis of Synthesis Example 1- (2): [Intermediate 1-b]

                               <Intermediate 1-b>

<Intermediate 1-a> (17.0 g, 45 mmol), sodium hydroxide (2.14 g, 54 mmol) and ethanol (170 ml) were placed in a 500 mL round bottom flask and refluxed for 48 hours. The reaction was terminated by thin film chromatography and then cooled to room temperature. 2 N hydrochloric acid was added dropwise to acidify. The resulting solid was stirred for 30 minutes and then filtered. Recrystallization from dichloromethane and n-hexane gave <Intermediate 1-b>. (14.5 g, 88.6%).

Synthesis of Synthesis Example 1- (3): [Intermediate 1-c]

                             <Intermediate 1-c>

<Intermediate 1-b> (14.5 g, 39 mmol) and 145 ml of methanesulfonic acid were placed in a 250 ml round bottom flask, and the mixture was heated to 80 ° C and stirred for 3 hours. The reaction was terminated by thin film chromatography and then cooled to room temperature. The reaction solution was slowly added dropwise to 150 ml of ice water and then stirred for 30 minutes. The resulting solid was filtered and washed with water and methanol to obtain <Intermediate 1-c>. (11.50 g, 83.4%).

Synthesis of Synthesis Example 1- (4): [Intermediate 1-d]

                            <Intermediate 1-d>

<Intermediate 1-c> (11.5 g, 33 mmol) and 300 ml of dichloromethane were added to a 1 L round bottom flask, and the mixture was stirred at room temperature. Bromine (3.4 ml, 66 mmol) was added dropwise to 50 ml of dichloromethane, and the mixture was stirred at room temperature for 8 hours. After completion of the reaction, 100 ml of acetone was added and stirred. The resulting solid was filtered and washed with acetone. The solid was recrystallized from monochlorobenzene to give < intermediate 1-d >. (11.0 g, 78%)

Synthesis of Synthesis Example 1- (5): [Intermediate 1-e]

                                   <Intermediate 1-e>

2-bromobiphenyl (8.4 g, 0.036 mol) and 110 ml of tetrahydrofuran were placed in a 250 ml round bottom flask and cooled to -78 ° C in a nitrogen atmosphere. N-butyl lithium (19.3 ml, 0.031 mol) was added dropwise at the same temperature. The reaction solution was stirred for 2 hours, and <Intermediate 1-d> (11.0 g, 0.026 mol) was added little by little and stirred at room temperature. When the color of the reaction solution changed, the reaction was terminated by TLC. H ₂ O (50 ml) was added to complete the reaction, followed by extraction with ethyl acetate and water. The organic layer was separated, concentrated under reduced pressure, and recrystallized from acetonitrile to obtain Intermediate 1-e. (12.2 g, 81.5%).

Synthesis of Synthesis Example 1- (6): [Intermediate 1-f]

                              <Intermediate 1-f>

<Intermediate 1-e> (12.0 g, 0.021 mol), acetic acid (120 ml) and sulfuric acid (2 ml) were placed in a 250 ml round bottom flask and refluxed for 5 hours. When a solid was formed, the reaction was terminated by thin film chromatography and then cooled to room temperature. The resulting solid was filtered, washed with H ₂ O and methanol, then dissolved in monochlorobenzene, filtered through silica gel, concentrated and then cooled to room temperature to obtain Intermediate 1-f. (10.7 g, 90%).

Synthesis of Synthesis Example 1- (7): [Intermediate 1-g]

                                   <Intermediate 1-g>

(5.0 g, 0.009 mol), (4-tert-butylphenyl) -phenylamine (2.5 g, 0.011 mol), palladium (II) acetate (0.08 g, 0.4 mmol) were added to a 250 ml round bottom flask. ), Sodium tertiary butoxide (3.4 g, 0.035 mol), triturated butylphosphine (0.07 g, 0.4 mmol) and toluene (60 ml) were added and the mixture was stirred under reflux for 2 hours. After completion of the reaction, the reaction solution was cooled to room temperature. The reaction solution was extracted with dichloromethane and water. The organic layer was separated, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography, and then recrystallized from dichloromethane and acetone to obtain Intermediate 1-g. (2.2 g, 35%).

Synthesis Example 1- (8): Synthesis of [Formula 101]

                                      &Lt; EMI ID =

To a 300 mL round bottom flask was added 2-chloro-4,6-diphenyl-1,3,5-triazine (12.3 g, 46 mmol), Intermediate 1-g (40.0 g, 56.4 mmol) 15.2 g, 91 mmol), tetrakistriphenylphosphine palladium (5.6 g, 9 mmol), water (80 mL), toluene (150 mL) and 1,4-dioxane (150 mL) were added and the mixture was 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 <Formula 101>. (29.3 g, 74%)

MS (MALDI-TOF): m / z 860.35 [M ^&lt; ⁺ &^gt;].

Synthesis Example 2: Synthesis of Compound (119)

Synthesis of Synthesis Example 2- (1): [Intermediate 2-a]

                 <Intermediate 2-a>

Methyl-5-bromosalicylate (41.1 g, 178 mmol) and dichloromethane were added to a 2 L round bottom flask reactor and stirred. Pyridine (28.1 g, 356 mmol) was added in a nitrogen atmosphere, and the mixture was stirred at room temperature for 20 minutes. After cooling to 0 ° C, trifluoromethanesulfonic anhydride (65.24 g, 231 mmol) was added dropwise in a nitrogen atmosphere. After stirring for 3 hours, the reaction was completed by TLC, 20 ml of water was added, and the mixture was stirred for 10 minutes. The reaction solution was concentrated under reduced pressure and then subjected to column separation to obtain <Intermediate 2-a> (38.8 g, 60%).

Synthesis of Synthesis Example 2- (2): [Intermediate 2-b]

&Lt; Intermediate 2-a > < Intermediate 2-b &

A 2 L round bottom flask was charged with ethyl cyanoacetate (202.9 g, 1.794 mol) and dimethylformamide (500 mL). Potassium hydroxide (67.1 g, 1.196 mol) and potassium cyanide (38.95 g, 0.598 mol) were added, and 200 ml of dimethylformamide was added thereto, followed by stirring at room temperature. <Intermediate 2-a> (267.6 g, 0.737 mol) was added in small portions to the reaction solution, followed by stirring at 50 ° C for 72 hours. After completion of the reaction, 200 ml of an aqueous solution of sodium hydroxide (25%) was added and the mixture was stirred under reflux. After stirring for 3 hours, the mixture was cooled to room temperature and extracted with ethyl acetate and water. The organic layer was separated, concentrated under reduced pressure, and separated by column chromatography to obtain <Intermediate 2-b> (73.0 g, 26%).

Synthesis of Synthesis Example 2- (3): [Intermediate 2-c]

                                          <Intermediate 2-c>

Bromobenzene (25.46 g, 0.163 mol) and 170 ml of tetrahydrofuran were placed in a 500 ml round bottom flask and cooled to -78 캜 in a nitrogen atmosphere. N-butyl lithium (1.6 mol) (95.6 ml, 0.153 mol) was added dropwise to the cooled reaction solution. After stirring at the same temperature for 1 hour, <Intermediate 2-b> (19.4 g, 0.051 mol) was added, followed by stirring at room temperature for 3 hours. After completion of the reaction, 50 ml of water was added and stirred for 30 minutes. After extraction with ethyl acetate and water, the organic layer was separated and concentrated under reduced pressure. Acetic acid (200 ml) and hydrochloric acid (1 ml) were added to the concentrated material, and the mixture was stirred at 80 占 폚. After completion of the reaction, the reaction mixture was cooled to room temperature and the resulting solid was filtered. After washing with methanol, <Intermediate 2-c> (17.9 g, 72%) was obtained.

Synthesis Example 2- (4): Synthesis of [intermediate 2-d]

                             <Intermediate 2-d>

<Intermediate 2-c> (18.0 g, 0.037 mol) and 600 ml of chloroform were placed in a 1 L round bottom flask. While stirring at room temperature, bromine (5.7 ml, 0.112 mol) was diluted in 40 ml of chloroform and added dropwise. After stirring for 12 hours at room temperature, 100 ml of methanol was added, and the resulting solid was filtered and washed with methanol. The material was recrystallized from 1,2-dichlorobenzene and acetone to give <intermediate 2-d> (12.8 g, 61%).

Synthesis Example 2- (5): Synthesis of [Formula 119]

Synthesis was carried out in the same manner as in Synthesis Examples 1-7 to 1-8, except that diphenylamine was used instead of (4-tert-butylphenyl) -phenylamine used in Synthesis Example 1-7 to obtain [Formula 119]. (Yield: 57%)

MS (MALDI-TOF): m / z 806.30 [M ^&lt; ⁺ &^gt;

Synthesis Example 3: Synthesis of Formula 242

Synthesis of Synthesis Example 3- (1): [Intermediate 3-a]

                                    <Intermediate 3-a>

4-dibenzoylboronic acid (85.0 g, 0.401 mol), bismuth (III) nitrate pentahydrate (99.2 g, 0.200 mol) and 400 ml of toluene were placed in a 2 L round bottom flask and stirred at 70 ° C for 3 hours in a nitrogen atmosphere . After completion of the reaction, the reaction mixture was cooled to room temperature and the resulting solid was filtered. After washing with toluene, <Intermediate 3-a> (61.5 g, 72%) was obtained.

Synthesis of Synthesis Example 3- (2): [Intermediate 3-b]

                                 <Intermediate 3-b>

A 2 L round bottom flask was charged with ethyl cyanoacetate (202.9 g, 1.794 mol) and dimethylformamide (500 mL). Potassium hydroxide (67.1 g, 1.196 mol) and potassium cyanide (38.95 g, 0.598 mol) were added, and 200 ml of dimethylformamide was added thereto, followed by stirring at room temperature. <Intermediate 3-a> (127.5 g, 0.737 mol) was gradually added to the reaction solution, followed by stirring at 50 ° C for 72 hours. After completion of the reaction, 200 ml of an aqueous solution of sodium hydroxide (25%) was added and the mixture was stirred under reflux. After stirring for 3 hours, the mixture was cooled to room temperature and extracted with ethyl acetate and water. The organic layer was separated, concentrated under reduced pressure, and subjected to column chromatography to separate <Intermediate 3-b> (20.0 g, 16%).

Synthesis Example 3- (3): Synthesis of Intermediate 3-c

<Intermediate 3-b> <Intermediate 3-c>

170 ml of <Intermediate 3-b> (20.0 g, 0.096 mol), 600 ml of ethanol and 142.26 g (2.53 mol) of potassium hydroxide aqueous solution was added to a 2 L round bottom flask and the mixture was refluxed for 12 hours. When the reaction was completed, the reaction solution was cooled to room temperature. The reaction solution was acidified with 400 ml of 6N hydrochloric acid. The resulting solid was stirred for 20 minutes and then filtered. The solid was washed with ethanol and <Intermediate 3-c> (17.0 g, 88.5%) was obtained.

Synthesis Example 3- (4): Synthesis of Intermediate 3-d

<Intermediate 3-c> <Intermediate 3-d>

<Intermediate 3-c> (17.0 g, 0.075 mol) and 15 ml of sulfuric acid were placed in a 2 L round bottom flask, and the mixture was stirred under reflux for 72 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with ethyl acetate and water. The organic layer was separated and washed with aqueous sodium hydrogencarbonate solution. The organic layer was excessively loaded with methanol under reduced pressure, and the resulting solid was filtered to obtain <Intermediate 3-d> (14.0 g, 77.6%).

Synthesis Example 3- (5): Synthesis of Intermediate 3-e

<Intermediate 3-d> <Intermediate 3-e>

<Intermediate 3-d> (14.0 g, 0.058 mol), 20 ml of hydrochloric acid and 100 ml of water were added to a 500 ml round-bottom flask, which was cooled to 0 ° C and stirred for 1 hour. At the same temperature, 50 ml of an aqueous solution of sodium nitrite (7.4 g, 0.116 mol) was added dropwise to the reaction solution, followed by stirring for 1 hour. When 100 ml of an aqueous solution of potassium iodide (30.0 g, 0.180 mol) was added dropwise, the temperature of the reaction solution was dropped so that the temperature did not exceed 5 ° C. After stirring for 5 hours at room temperature, the reaction mixture was washed with an aqueous solution of sodium cyanosulfate and extracted with ethyl acetate and water. The organic layer was separated and concentrated under reduced pressure, followed by separation by column chromatography to obtain Intermediate 3-e (9.1 g, 48%)

Synthesis Example 3- (6): Synthesis of Intermediate 3-f

<Intermediate 3-e> <Intermediate 3-f>

(9.3 g, 25 mmol), 1-dibenzofuranboronic acid (8.3 g, 28 mmol), tetrakis (triphenylphosphine) palladium (0.6 g, 0.05 mmol) in a 250 mL round bottom flask, , Potassium carbonate (6.7 g, 50 mmol), and 50 mL of toluene, 50 mL of tetrahydrofuran and 20 mL of water were added. The temperature of the reactor was raised to 80 ° C and stirred for 10 hours. When the reaction was completed, the temperature of the reactor was lowered to room temperature, extracted with ethyl acetate, and the organic layer was separated. The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain <Intermediate 3-f> (5.3 g, 52.3%).

Synthesis Example 3- (7): Synthesis of Intermediate 3-g

<Intermediate 3-f> <Intermediate 3-g>

<Intermediate 3-f> (5.3 g, 15 mmol), sodium hydroxide (0.7 g, 17 mmol) and ethanol (50 ml) were added to a 100 mL round bottom flask and the mixture was refluxed for 48 hours. The resulting solid, which was acidified by dropwise addition of 2-N hydrochloric acid to the solution cooled to room temperature, was stirred for 30 minutes and then filtered. Recrystallization from dichloromethane and hexane gave <Intermediate 3-g> (4.5 g, 88.0%).

Synthesis Example 3- (8): Synthesis of Intermediate 3-h

<Intermediate 3-g> <Intermediate 3-h>

<Intermediate 3-g> (4.5 g, 12 mmol) and 30 ml of methanesulfonic acid were placed in a 100 ml round bottom flask, and the mixture was heated to 80 ° C. and stirred for 3 hours. After cooling to room temperature, the reaction solution was slowly added dropwise to 50 ml of ice water, followed by stirring for 30 minutes. The resulting solid was filtered and washed with water and methanol to obtain <Intermediate 3-h> (3.8 g, 88.8%).

Synthesis Example 3- (9): Synthesis of Intermediate 3-i

<Intermediate 3-h> <Intermediate 3-i>

<Intermediate 3-h> (3.8 g, 11 mmol) and 40 ml of dichloromethane were added to a 100 mL round bottom flask and stirred at room temperature. Bromine (1.1 ml, 22 mmol) was added dropwise to 10 ml of dichloromethane, and the mixture was stirred at room temperature for 8 hours. After completion of the reaction, 20 ml of acetone was added to the reaction vessel and stirred. The resulting solid was filtered and washed with acetone. The solid was recrystallized from monochlorobenzene to give <Intermediate 3-i> (3.0 g, 55%).

Synthesis Example 3- (10): Synthesis of Intermediate 3-j

<Intermediate 3-i> <Intermediate 3-j>

2-bromobiphenyl (2.1 g, 0.009 mol) and 30 ml of tetrahydrofuran were placed in a 100 ml round bottom flask and cooled to -78 캜 in a nitrogen atmosphere. N-butyl lithium (4.8 ml, 0.008 mol) was added dropwise at the same temperature to the cooled reaction solution. The reaction solution was stirred for 2 hours, <Intermediate 3-i> (3.0 g, 0.006 mol) was added little by little and the mixture was stirred at room temperature. The reaction was completed by adding 10 ml of H 2 O and extracted with ethyl acetate and water. The organic layer was separated, concentrated under reduced pressure, and recrystallized from acetonitrile to obtain Intermediate 3-j (2.5 g, 64%).

Synthesis Example 3- (11): Synthesis of Intermediate 3-k

<Intermediate 3-j> <Intermediate 3-k>

<Intermediate 3-j> (2.5 g, 0.04 mol), 25 ml of acetic acid and 0.5 ml of sulfuric acid were placed in a 100 ml round bottom flask, and the mixture was refluxed and stirred for 5 hours. When a solid was formed, the reaction was terminated by thin film chromatography and then cooled to room temperature. The resulting solid was filtered, washed with H2O and methanol, dissolved in monochlorobenzene, filtered through silica gel, concentrated and then cooled to room temperature to obtain <Intermediate 3-k> (2.2 g, 90%).

Synthesis Example 3- (12): Synthesis of Intermediate 3-l

                          <Intermediate 3-l>

(8.0 g, 0.035 mol), 4-tertiarybutyl aniline (5.8 g, 0.039 mol), tris (dibenzylideneacetone) dipalladium (0 ) (0.65 g, 0.0007 mol), sodium tertiary butoxide (6.79 g, 0.0706 mol), 2,2'-bis (diphenylphosphino) -1,1'-binaphthalene And the mixture was stirred under reflux for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with ethyl acetate and water. The organic layer was separated, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The reaction mixture was separated by column chromatography to obtain <Intermediate 3-l> (7.5 g, 72%).

Synthesis of Synthesis Example 3- (13): [Formula 242]

Intermediate 3-l> was obtained in the same manner as in Synthesis Example 1-7, except that <Intermediate 3-k> was used instead of <Intermediate 1-f> used in Synthesis Example 1-7 and Intermediate 3-1 was used in place of (4-tert- To (1-8) to give [Formula 242]. (Yield: 55%)

MS (MALDI-TOF): m / z 1022.40 [M ^&lt; ⁺ &^gt;

Synthesis Example 4: Synthesis of Formula 252

Synthesis Example 4- (1): Synthesis of Intermediate 4-a

<Intermediate 3-f> <Intermediate 4-a>

Bromobenzene (25.5 g, 0.163 mol) and 170 ml of tetrahydrofuran were placed in a 500 ml round-bottomed flask and cooled to -78 캜 in a nitrogen atmosphere. Butyllithium (1.6 M) (95.6 ml, 0.153 mol) was added dropwise to the cooled reaction solution. After stirring at the same temperature for 1 hour, <Intermediate 3-f> (20.0 g, 0.051 mol) was added, followed by stirring at room temperature for 3 hours. After completion of the reaction, 50 ml of water was added and stirred for 30 minutes. After extraction with ethyl acetate and water, the organic layer was separated and concentrated under reduced pressure. Acetic acid (200 ml) and hydrochloric acid (1 ml) were added to the concentrated material, and the mixture was stirred at 80 占 폚. After completion of the reaction, the reaction mixture was filtered at room temperature and washed with methanol to obtain <Intermediate 4-a> (20.0 g, 78%).

Synthesis Example 4- (2): Synthesis of Intermediate 4-b

&Lt; Intermediate 4-a > < Intermediate 4-b &

Bromine (5.8 ml, 116 mmol) was added dropwise to 10 ml of dichloromethane, and the mixture was stirred for 8 hours at room temperature. The reaction mixture was stirred at room temperature for 2 hours. <Intermediate 4-a> (20 g, 58 mmol) and 40 ml of dichloromethane were added to a 100 ml round bottom flask. After completion of the reaction, 20 ml of acetone was added to the reaction vessel, and the resulting solid was filtered and washed with acetone, and recrystallized from monochlorobenzene to obtain <Intermediate 4-b> (15.8 g, 55%) .

Synthesis Example 4- (3): Synthesis of [Formula 252]

Intermediate 4-b> was used in place of <Intermediate 1-f> used in Synthesis Example 1-7, and Synthesis Example 1-7 was performed using di-p-tolylamine instead of (4-tert-butylphenyl) To (1-8) to give [Formula 252]. (Yield: 58%)

MS (MALDI-TOF): m / z 924.35 [M ^&lt; ⁺ &^gt;].

Examples 1 to 4: Preparation of organic light emitting device (red phosphorescent host)

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, an organic material was coated on the ITO using HATCN (50 Å), NPD (1500 Å), compound prepared by the present invention + red phosphorescent dopant RD) to form a light emitting layer having a thickness of 400 Å.

Then, the following compounds were deposited in the order of ET: Liq = 1: 1 (300 Å), Liq (10 Å), and Al (1,000 Å). remind

The structures of HATCN, NPD, RD, ET and Liq are as follows.

[HATCN] [NPD]

[RD] [ET] [Liq]

Comparative Example  One

The organic light emitting device for Comparative Example 1 was fabricated in the same manner as in Example 1 except that BAlq, which is generally used as a red phosphorescent host material, was used instead of the compound prepared by the present invention. The structure is as follows.

[BAlq]

The voltage and color coordinates of the organic light emitting device manufactured according to Examples 1 to 4 and Comparative Example 1 were measured and the results are shown in Table 1 below.

division Host V CIEx CIEy Comparative Example 1 BAlq 6.2 0.665 0.334 Example 1 Formula 101 3.2 0.663 0.336 Example 2 (119) 3.1 0.663 0.336 Example 3 242 3.1 0.662 0.337 Example 4 252 3.2 0.663 0.336

As shown in Table 1, it can be confirmed that the heterocyclic compound prepared by the present invention has a lower driving voltage than that of Comparative Example 1.

Claims (13)

A heterocyclic compound having an amine group represented by any one of the following formulas (A) to (C).
(A)

[Chemical Formula B]

&Lt; RTI ID = 0.0 &

In the above formulas (A) to (C)
A1, A2, E and F are the same or different and each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 40 carbon atoms;
Two carbon atoms adjacent to each other in the aromatic ring of A1 and two carbon atoms adjacent to each other in the aromatic ring of A2 form a condensed ring by forming a 5-membered ring with carbon atoms connected to the substituents R1 and R2;
Each of the linking groups L1 to L10 is the same or different and independently selected from a single bond and a substituted or unsubstituted arylene group having 6 to 60 carbon atoms;
M is any one selected from NR ₃ , CR ₄ R ₅ , O, and S;
Substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, A substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 alkylsilyl group, a substituted or unsubstituted C6 to C30 aryl And a silyl group
The substituents R3 to R5 are selected from among hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, and substituted or unsubstituted C6-C50 aryl Which one,
R 1 and R 2 may be connected to each other to form a monocyclic or polycyclic ring of alicyclic or aromatic,
The substituent HA is a substituted or unsubstituted heteroaryl group containing a heteroatom selected from O, S and N having 2 to 30 carbon atoms,
Each of p1 to p3, r1 to r3, s1 to s3 and q is the same or different and independently of one another is an integer of 1 to 3, and when each of these is 2 or more, each of the linking groups L1 to L10 is the same or different from each other ,
X, y and z are the same or different and independently of one another an integer of 0 to 1,
Ar1 and Ar2, Ar3 and Ar4, and Ar5 and Ar6 may be linked to each other to form a ring;
In the above formulas (A) and (B), two carbon atoms adjacent to each other in the A2 ring are bonded to * in the above formula (Q1) to form a condensed ring, and x = 1, y =
In the formula (C), two carbon atoms adjacent to each other in the A1 ring are bonded to * in the formula Q2 to form a condensed ring, and two carbon atoms adjacent to each other in the A2 ring are bonded to * in the formula Q1, Wherein x = 1, y and z are each 0,
Herein, the 'substitution' in the 'substituted or unsubstituted' in the above Chemical Formulas A to C is a substituent selected from the group consisting of deuterium, a cyano group, a halogen group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, An arylalkyl group having 7 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, and an arylsilyl group having 6 to 24 carbon atoms Substituted with one or more substituents selected from the group consisting of &lt; RTI ID = 0.0 &gt; The method according to claim 1,
Wherein A ₁ , A ₂ , E and F are the same or different and are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms. 3. The method of claim 2,
The substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms may be the same or different and independently selected from the group consisting of Structural Formulas 10 to 21.
[Structural formula 10] [Structural formula 11] [Structural formula 12]

[Structural Formula 13] [Structural Formula 14] [Structural Formula 15]

[Structural formula 16] [Structural formula 17] [Structural formula 18]

[Structural formula 19] [Structural formula 20] [Structural formula 21]

In the above structural formulas 10 to 21, "- *" represents a 5-membered ring containing carbon atoms connected to the substituents R ₁ and R ₂ , or a 5-membered ring containing M in the structural formulas Q ₁ and Q ₂ Means a binding site for forming a circular ring,
When the aromatic hydrocarbon rings of the above-mentioned structural formulas 10 to 21 are bonded to the structural formula Q ₁ or the structural formula Q ₂ corresponding to the A ₁ ring or the A ₂ ring, two adjacent carbon atoms of the structural formula Q ₁ Lt; / RTI &gt; of formula Q &lt; ₂ &gt; or in combination with * of formula Q2 to form a condensed ring;
Wherein R is the same as R ₁ and R ₂ defined in claim 1, and m is an integer of 1 to 8, and when m is 2 or more, or when R is 2 or more, May be the same as or different from each other. The method according to claim 1,
The linking groups L ₁ to L ₁₀ in the above formulas A to C are the same or different and each is a single bond or a group selected from the following formulas [22], [23], [25], [27] Is a group selected from the group consisting of a hydrogen atom, a halogen atom and a halogen atom.
[Structural Formula 22] [Structural Formula 23] [Structural Formula 25]

[Structural Formula 27] [Structural Formula 28]

[Structural Formula 30]

The carbon position of the aromatic ring in the linking group may be bonded with hydrogen or deuterium. delete The method according to claim 1,
Wherein HA in any one of formulas (A) to (C) is any heteroaryl group selected from formulas (A) to (O).
[Structural formula A] [Structural formula B] [Structural formula C]

[Structural formula D] [Structural formula E] [Structural formula F]

[Structural formula G] [Structural formula H] [Structural formula I]

[Structural formula J] [Structural formula K] [Structural formula L]

[Structural formula M] [Structural formula N] [Structural formula O]

The substituents R in the structural formulas A to O are the same as those of R 1 to R 5 defined in claim 1,
Wherein n is an integer of 1 to 7, and when n is 2 or more, each R is the same or different,
When n is 2 or more, each substituent R may combine with adjacent substituent R to form a saturated or unsaturated ring. delete The method according to claim 1,
The heterocyclic compound having an amine group represented by any one of the above formulas A to C is any one selected from the following formulas (101) to (277), (284) to (310) compound.
<Formula 101><Formula102><Formula103>

&Lt; EMI ID = 106.1 >

<Formula 107><Formula108><Formula109>

&Lt; Formula 110 >< EMI ID =

<Formula 113><Formula114><Formula115>

&Lt; EMI ID = 116.1 &gt;

&Lt; EMI ID = 120.1 &gt;

&Lt; Formula 122 &gt;&lt; EMI ID =

<Formula 125> Formula 126> Formula 127>

&Lt; Formula 128 >< EMI ID = 129.0 >

&Lt; Formula 131 >< EMI ID =

&Lt; Formula 134 &gt;&lt; EMI ID =

&Lt; Formula 137 >< EMI ID = 139.0 >

&Lt; Formula 140 >< EMI ID =

&Lt; Formula 143 &gt;&lt; EMI ID =

&Lt; Formula 146 >< EMI ID =

<Formula 149><Formula150>

<Formula 152><Formula153>

<Formula 155><Formula156><Formula157>

&Lt; Formula 15 &gt;&lt; EMI ID =

<Formula 161><Formula162><Formula163>

<Formula 164><Formula165><Formula166>

&Lt; Formula 167 >< EMI ID =

&Lt; Formula 170 &gt;&lt; EMI ID =

&Lt; Formula 173 >< EMI ID =

&Lt; Formula 176 &gt;&lt; EMI ID =

&Lt; Formula 179 >< EMI ID =

&Lt; Formula 182 &gt;&lt; EMI ID =

&Lt; Formula 186 >< EMI ID =

<Formula 188><Formula189><Formula190>

<Formula 191><Formula192><Formula193>

&Lt; Formula 194 &gt;&lt; EMI ID =

&Lt; Formula 197 >< EMI ID =

&Lt; Formula 200 &gt;&lt; EMI ID =

&Lt; Formula 203 >< EMI ID =

<Formula 206><Formula207>

&Lt; Formula 210 &gt;&lt; EMI ID =

<Formula 212><Formula213><Formula214>

&Lt; Formula 215 >

<Formula 218><Formula219><Formula220>

&Lt; Formula 221 >< EMI ID =

<Formula 224><Formula225><Formula226>

&Lt; Formula 228 &gt;&lt; EMI ID =

&Lt; Formula 230 >< EMI ID =

<Formula 233><Formula234><Formula235>

<Formula 236><Formula237><Formula238>

&Lt; Formula 239 &gt;&lt; EMI ID =

&Lt; EMI ID = 242 >

<245><Formula246><Formula247>

&Lt; Formula 248 >< EMI ID =

[Formula 252] &lt; EMI ID =

&Lt; Formula 254 >< EMI ID =

&Lt; Formula 257 &gt;&lt; EMI ID =

<Formula 260><Formula262><Formula262>

&Lt; Formula 263 >< EMI ID =

&Lt; Formula 266 &gt;&lt; EMI ID =

&Lt; EMI ID = 31.1 >

&Lt; EMI ID = 272 >

(277) < EMI ID = 275.1 >

&Lt; Formula 284 >

&Lt; Formula 288 >< EMI ID =

&Lt; EMI ID = 290 &gt;

&Lt; Formula 293 &gt;&lt; EMI ID =

&Lt; EMI ID = 298 >

&Lt; Formula 300 >< EMI ID =

&Lt; Formula 302 &gt;&lt; EMI ID =

&Lt; Formula 305 >< EMI ID =

&Lt; Formula 308 &gt;&lt; EMI ID =

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 a heterocyclic compound having an amine group of any one of claims 1 to 4, 6 and 8, An organic light-emitting device comprising at least one organic light-emitting device. 10. The method of claim 9,
Wherein the organic layer comprises at least one of a hole injecting layer, a hole transporting layer, an electron blocking layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. 10. The method of claim 9,
An organic layer interposed between the first electrode and the second electrode includes a light emitting layer,
Wherein the light emitting layer comprises a host and a dopant, and the heterocyclic compound having an amine group is used as a host. 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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