KR20180023511A - Novel organic compounds and organic light-emitting diode therewith - Google Patents

Abstract

The present invention relates to an organic compound represented by the chemical formula A or B, and to an organic light-emitting diode comprising the same, and in the chemical formula A and the chemical formula B, R1 to R12, L1, L2, Ar1 to Ar3, n and m are as described in the description of the invention. Accordingly, a first technical object of the present invention is to provide a specific structure of organic compound having high efficiency, low voltage and long life characteristics by using the compound in an emitting layer, an electron transporting layer or a hole transporting layer in the organic light emitting diode.

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 luminescent material may be classified into a phosphorescent material derived from the singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to the luminescent mechanism.

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.

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 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.

On the other hand, a material used as an organic material layer in an organic light emitting device can be a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material as well as a light emitting material depending on its function.

Of these, in order to produce an organic compound having excellent electron transporting ability and hole blocking ability, excellent luminous efficiency and high stability in a thin film state, as a prior art related to an electron transporting layer material, it is disclosed in Korean Patent Publication No. 10-2012-0104204 (2012.09.20) describes an organic compound in which a pyridoindole derivative is bonded to a substituted anthracene ring structure, and in JP-A-2010-168363 (2010.08.05), an external quantum efficiency and a driving voltage Discloses an anthracene derivative having a pyridine naphthyl group, which has excellent characteristics.

On the other hand, as a conventional technique related to the hole transporting layer, in JP-A 10-1074193 (Oct. 2011, Oct. 14, 2011), organic compounds using a compound having a core structure in which at least one benzene ring is condensed in a carbazole structure as a hole transporting layer compound Emitting device is disclosed in Japanese Patent Application Laid-Open No. 10-1455156 (Publication Date: Oct. 24, 2014, Oct. 27, 2014), an emission assistant having a HOMO energy level between a hole transport layer HOMO energy level and a light emission layer HOMO energy level is provided between a hole transport layer and a light emission layer Emitting layer having a layer formed thereon is disclosed.

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 for a light emitting layer, an electron transporting layer, and a hole transporting layer for a light emitting device.

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)

Japanese Unexamined Patent Application Publication No. 2010-168363 (Aug. 05, 2010)

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 the compound in an emitting layer, an electron transporting layer, or 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 comprising the organic compound in a light emitting layer, an electron transporting layer, or a hole transporting layer.

In order to achieve the above technical problems, the present invention provides an organic compound represented by the following formula (A) or (B).

(A)

[Chemical Formula B]

In the above formulas (A) and (B)

Wherein X is CR21R22 or NR23,

The substituents R 1 to R 12 are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, 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 C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C5 to C30 cycloalkenyl group, A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms, , A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom, a cyano group, a nitro group, a halogen group, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms , A substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, a substituted or unsubstituted aluminum group, a carbonyl group, a phosphoryl group, an amino group, a thiol group, a hydroxyl group, a selenium group, a tellurium group, An ester group,

R21 to R23 are the same or different from each other and each independently represents hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3- Lt; RTI ID = 0.0 > to 50 < / RTI > heteroaryl groups,

In the above formula (A), one or two substituents of the substituents R 1 to R 12 and the substituent R 23 are a single bond bonded to the above-mentioned A 1,

In the above formula (B), one or two substituents of the substituents R 1 to R 12 are a single bond bonding to the A 2, Ar 2 and L 2 in the A 2 may be connected to each other to form a condensed ring, and Ar 3 and L 2 They may be connected to each other to form a condensed ring,

The linking groups L 1 and L 2 are the same or different and independently represent a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted C2- A substituted or unsubstituted C2-C60 alkynylene group, a substituted or unsubstituted C3-C60 cycloalkylene group, a substituted or unsubstituted C2-C60 heterocycloalkylene group, a substituted or unsubstituted C6-C60 arylene group, Or an unsubstituted heteroarylene group having 2 to 60 carbon atoms;

n and m are the same or different and independently of each other an integer of 0 to 3, and when each of these is 2 or more, each of the linking groups L1 and L2 is the same or different from each other,

Each of Ar 1 to Ar 3 is the same or different and independently represents a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 40 carbon atoms A substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms.

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 the formula (A) or (B) in the light emitting layer, the electron transporting layer or the hole transporting layer according to the present invention can have high efficiency, low voltage and long life .

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 the following formula (A) or (B).

(A)

[Chemical Formula B]

In the above formulas (A) and (B)

Wherein X is CR21R22 or NR23,

The substituents R 1 to R 12 are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, 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 C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C5 to C30 cycloalkenyl group, A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms, , A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom, a cyano group, a nitro group, a halogen group, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms , A substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, a substituted or unsubstituted aluminum group, a carbonyl group, a phosphoryl group, an amino group, a thiol group, a hydroxyl group, a selenium group, a tellurium group, An ester group,

R21 to R23 are the same or different from each other and each independently represents hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3- Lt; RTI ID = 0.0 > to 50 < / RTI > heteroaryl groups,

In the above formula (A), one or two substituents of the substituents R 1 to R 12 and the substituent R 23 are a single bond bonded to the above-mentioned A 1,

In the above formula (B), one or two substituents of the substituents R 1 to R 12 are a single bond bonding to the A 2, Ar 2 and L 2 in the A 2 may be connected to each other to form a condensed ring, and Ar 3 and L 2 They may be connected to each other to form a condensed ring,

The linking groups L 1 and L 2 are the same or different and independently represent a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted C2- A substituted or unsubstituted C2-C60 alkynylene group, a substituted or unsubstituted C3-C60 cycloalkylene group, a substituted or unsubstituted C2-C60 heterocycloalkylene group, a substituted or unsubstituted C6-C60 arylene group, Or an unsubstituted heteroarylene group having 2 to 60 carbon atoms;

n and m are the same or different and independently of each other an integer of 0 to 3, and when each of these is 2 or more, each of the linking groups L1 and L2 is the same or different from each other,

Each of Ar 1 to Ar 3 is the same or different and independently represents a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 40 carbon atoms A substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms,

The 'substituted' in the 'substituted or unsubstituted' may be a substituent selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, An alkenyl group, 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 24 carbon atoms An alkenyl group having 2 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, An aryl group having from 6 to 24 carbon atoms, an arylalkyl group having from 7 to 24 carbon atoms, a heteroaryl group having from 2 to 24 carbon atoms, or a heteroarylalkyl group having from 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 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.

The compounds represented by the above formula (A) or (B) according to the present invention will be described in more detail. The 5-membered ring containing 6-membered aromatic carbon ring-X containing R 1 to R 4 -R 5 to R 12 (Phenanthrene skeleton) 'having a carbon number of 14 is condensed with each other, and substituents R1 to R12 in these condensed rings and one or two of R23 bonded to the nitrogen atom when X is nitrogen And one or two substituents of the substituents R 1 to R 12 in these condensed rings are single bonds bonded to the above-mentioned A 2.

In one embodiment, the substituent groups Ar1 to Ar3 in the above-mentioned [Formula A] and [Formula B] 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 C2- Lt; / RTI > to < RTI ID = 0.0 > 30, < / RTI >

More preferably, Ar1 in the formula [A] may be a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and Ar2 and Ar3 in the formula [B] are the same or different, Or an aryl group having 6 to 30 carbon atoms.

In the present invention, when the substituent Ar 1 in the above-mentioned formula [A] is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, the substituent Ar 1 may be any one selected from the following formulas A to S:

[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]

[Structural formula P] [Structural formula Q]

[Structural formula R] [Structural formula S]

The substituents R in the structural formulas A to S are the same as those of R1 to R12 defined above,

K is an integer of 1 to 7, and when k is 2 or more, each R is the same or different,

When k is 2 or more, each substituent R may be bonded to adjacent substituent R to form a saturated or unsaturated ring.

In one preferred embodiment of the present invention, in the above-mentioned formula (A), one of the substituents R 1 to R 12 and R 2 3 is a single bond to be bonded to the above-mentioned A 1, And one substituent may be a single bond which binds to the above-mentioned A2. In this case, in the above-mentioned formulas (A) and (B), one of the substituents R1 to R4 is a single bond which binds to A1 or A2, or one of the substituents R5 to R12 is bonded to A1 or A2 Or in the above formula (A), the substituent R23 may be a single bond bonding with Al.

In an embodiment of the present invention, among the substituents R1 to R12, the substituent which is not connected to A1 or A2 may be hydrogen or deuterium.

In the present invention, the linking groups L 1 and L 2 may be the same or different from each other and each independently 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 of the present invention, the carbon position of the aromatic ring may be bonded to hydrogen or deuterium.

Specific examples of the compound represented by the above formula (A) or (B) according to the present invention include, but are not limited to, a compound represented by any one selected from the following [compounds 1] to [ .

<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 &

<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>

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 layer containing the organic compound 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 .

Further, the light emitting layer includes a phosphorescent host and a phosphorescent dopant, and the organic compound can be used as a phosphorescent host.

In this case, the light emitting layer may further include a dopant other than a host, and 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 .

Further, the organic compound of the present invention can be used for a hole transporting layer or for an electron transporting layer.

As the material of the hole transport layer according to the present invention, the organic compound represented by the formula (A) or the formula (B) of the present invention may be used, and in addition to the organic compound represented by the formula (A) or Compounds may be further included and used. In the case where the organic compound represented by the above formula (A) or (B) is not used, a commonly used hole transport layer material may be used.

As the compound to be used at this time, an electron donor molecule having a low ionization potential can be used, and diamine, triamine or tetraamine derivative having a basic skeleton of triphenylamine is mainly used. For example, N, N ' (TPD) or N, N'-di (naphthalen-1-yl) -N (N'-diphenyl- , N'-diphenylbenzidine (a-NPD), and the like.

A hole injection layer (HIL) may be additionally formed on the lower part of the hole transport layer. The hole injection layer material may be an organic compound represented by the formula (A) or (B) In the case where the organic compound represented by the above formula (A) or (B) is not used, a hole injection layer commonly used in the art can be used.

Such conventionally used hole injection layers include, for example, copper phthalocyanine (CuPc) or starburst type amine TCTA (4,4 ', 4 "-tri (N-carbazolyl) triphenylamine), m- 4 ', 4 "-tris- (3-methylphenylphenylamino) triphenylamine) and the like can be used.

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.

The phosphorescent dopant used in the case where the light emitting layer utilizes phosphorescence is preferably a compound represented by the following general formula (A-1) to (J-1) And the like.

[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 L1, L2 and L3 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,

YA11, YA14, YA15 and YA18 each independently represent a carbon atom or a nitrogen atom, and YA12, YA13, YA16 and YA17 each independently represent a hydrogen atom, Wherein LA11, LA12, LA13, and LA14 each represent a linking group as defined above, and QA11 and QA12 each represent an atom bonding to MA1, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkoxy group, .

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,

YB11, YB14, YB15 and YB18 each independently represent a carbon atom or a nitrogen atom; YB12, YB13, YB16 and YB17 each independently represent a substituted or unsubstituted LB11, LB12, LB13 and LB14 represent a linking group, and QB11 and QB12 represent a partial structure containing an atom bonded to MB1.

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,

MC1 represents a metal ion which is the same metal ion as defined in formula A-1, RC11 and RC12 each independently represent a hydrogen, a substituent forming a 5-membered ring and a substituent having no connection with each other, And GC12 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom, and LC11 and LC12 each represent a linking group or a linking group, And QC11 and QC12 represent partial structures containing atoms bonding to MC1.

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,

MD1 represents the same metal ion as defined in formula (A-1), GD11 and GD12 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom, and JD11, JD12, JD13 and JD14 each independently represent a five- And LD11 and LD12 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,

ME1 represents the same metal ion as defined in formula A-1, JE11 and JE12 each independently represent an atomic group necessary for forming a 5-membered ring, and GE11, GE12, GE13 and GE14 each independently represent a nitrogen atom, a substituent Or an unsubstituted carbon atom, and each of YE11, YE12, YE13 and YE14 independently represents 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,

MF1 represents the same metal ion as defined in the general formula A-1,

RF11, RF12, RF12 and RF13, and RF13 and RF14 are connected to each other to form a ring. At this time, RF1, RF12, RF13, and RF13 are connected to each other. And the ring formed by the RF14 are five-membered rings. QF11 and QF12 also represent a partial structure containing an atom binding to MF1.

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,

R11 and R12 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,

L1 is a ligand which binds to platinum and is preferably a ligand capable of forming an ortho metal platinum complex, a nitrogen-containing heterocyclic ligand, a diketone ligand or a halogen ligand, more preferably an ortho metal ) Ligand forming a platinum complex, a bipyridyl ligand, or a phenanthroline ligand.

n1 is an integer of 0 to 3, preferably 0, and m1 is 1 or 2,

It is preferable that n1 and m1 are such that the metal complex represented by the general formula H-1 is a neutral complex.

R21, R22, n2, m2, q22 and L2 are the same as R11, R12, n1, m1, q12 and L1 in the general formula H-2, q21 is an integer of 0 to 2, .

In the general formula H-3, R31, n3, m3 and L3 are the same as R11, n1, m1 and L1 respectively, q31 is an integer of 0 to 8, preferably 0 to 2, Do.

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]

    [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. X1, X2, X3 and X4 represent a nitrogen atom in which two of the double bonds coordinate to the platinum atom, and the remaining two represent a carbon atom or a nitrogen atom. Q1, Q2 and Q3 each independently represent a divalent atom (or a group) or a bond, but Q1, Q2 and Q3 do not simultaneously represent a bond. Two of Z1, Z2, Z3 and Z4 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.

Meanwhile, the electron transport layer used in the present invention functions to stably transport electrons injected from an electron injection electrode (cathode), and the organic compound represented by the above formula (A) or (B) according to the present invention is used, or When a commonly used material for an electron transporting layer is used as a mixture with the organic compound material of the present invention or when the organic compound represented by the above formula A or B in the present invention is not used, Can be used.

Examples of commonly used electron transporting layer compounds include quinoline derivatives, especially tris (8-quinolinolate) aluminum (Alq3), TAZ, BAlq, beryllium bis (benzoquinolyl- (benzoquinolin-10-olate: Bebq2), BCP, compound 201, compound 202, oxadiazole derivative PBD, BMD, BND and the like may be used.

TAZ BAlq

&Lt; Compound 201 > < Compound 202 > 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, Li2O, and BaO can be used.

As the electron injection layer forming material, any material known as an electron injection layer forming material such as CsF, NaF, LiF, NaCl, Li2O, BaO, or the like 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) or the like which is transparent and excellent in conductivity is 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.

Synthesis Example 1. Synthesis of [Compound 2]

Synthesis Example 1-1. Synthesis of [intermediate 1-a]

                              [Intermediate 1-a]

A 2 L reactor was charged with 100 g (406 mmol) of 1-bromocarbazole, 113 g (446 mmol) of bis (pinacolato) diboron and 8.9 g of [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (12.2 mmol), potassium acetate (119 g, 1218 mmol), and toluene (1 L) were refluxed for 12 hours. After filtration at a high temperature, the filtrate was concentrated under reduced pressure and then separated by column chromatography to obtain 89.3 g (yield 75%) of [intermediate 1-a].

Synthesis Example 1-2. Synthesis of [intermediate 1-b]

  [Intermediate 1-a] [Intermediate 1-b]

A 2 L reactor was charged with 89 g (304 mmol) of Intermediate 1-a, 56.3 g (304 mmol) of 2-bromobenzaldehyde, 7 g (6.1 mmol) of tetrakis (triphenylphosphine) palladium, 89.5 g 912 mmol), 900 mL of toluene and 300 mL of distilled water, and the mixture was stirred at 100 ° C for 12 hours. After cooling to room temperature, the organic layer was extracted. The mixture was concentrated under reduced pressure and then separated by column chromatography to obtain 52.7 g (yield: 64%) of Intermediate 1-b.

Synthesis Example 1-3. [Synthesis of intermediate 1-c]

[Intermediate 1-b] [Intermediate 1-c]

A 2L reaction vessel was charged with 32.3 g (288 mmol) of potassium tertiary butoxide and 200 ml of tetrahydrofuran, followed by cooling to 0 占 폚 under a nitrogen atmosphere. 98.7 g (288 mmol) of methoxymethyltriphenylphosphonium chloride were dissolved in 300 ml of tetrahydrofuran, and the mixture was stirred for 30 minutes. 53 g (192 mmol) of Intermediate 1-b was dissolved in 500 ml of tetrahydrofuran, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was extracted, and the organic layer was concentrated under reduced pressure, and the resultant product was separated by column chromatography to obtain 50.5 g of [intermediate 1-c]. (Yield: 88%)

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

[Intermediate 1-c] [Intermediate 1-d]

50 g (167 mmol) of Intermediate 1-c, 5.4 g (8.3 mmol) of bismuth (III) trifluoromethanesulfonate and 500 ml of 1,2-dichloroethane were placed in a 1 L reaction vessel under nitrogen atmosphere And the mixture was stirred for 3 hours. After completion of the reaction, methyl alcohol was used to form a precipitate, which was then filtered to obtain 39 g (yield 89%) of [Intermediate 1-d].

Synthesis Example 1-5. Synthesis of [Compound 2]

 [Intermediate 1-d] [Compound 2]

To a 300 mL reactor were added 10 g (37 mmol) of [intermediate 1-d], 14.5 g (37 mmol) of 2- (4-bromophenyl) (Dibenzylideneacetone) 0.67 g (0.74 mmol) of dipalladium, 1.1 g (3.7 mmol) of tritiated butylphosphonium tetrafluoroborate, 7.1 g (74 mmol) of sodium tertiarybutoxide and 100 mL of xylene And refluxed for 12 hours. After filtration at a high temperature, the filtrate was concentrated under reduced pressure and then separated by column chromatography to obtain 13.2 g (yield: 62%) of [Compound 2].

MS (MALDI-TOF): m / z 574.22 [M] &lt; + &

Synthesis Example 2. Synthesis of [Compound 25]

Synthesis Example 2-1. Synthesis of [intermediate 2-a]

                                         [Intermediate 2-a]

A 1 L reactor was charged with 27.4 g (232 mmol) of 2-aminobenzonitrile and 300 mL of tetrahydrofuran, and the mixture was stirred. After cooling to 0 占 폚, 88.2 mL (487 mmol) of 3M-phenylmagnesium bromide was added dropwise, and the mixture was refluxed for 3 hours. After cooling to 0 캜, 44.3 g (732 mmol) of ethyl chloroformate was dissolved in 200 mL of tetrahydrofuran, and the mixture was refluxed for 2 hours. After cooling to 0 ° C, a saturated aqueous ammonium chloride solution was added, and the organic layer was extracted. The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain 40 g (yield 78%) of [intermediate 2-a].

Synthesis Example 2-2. Synthesis of [intermediate 2-b]

  [Intermediate 2-a] [Intermediate 2-b]

40 g (181 mmol) of [intermediate 2-a] and 400 mL of phosphorus oxychloride were placed in a 1 L reactor and refluxed for 5 hours. After cooling to 0 占 폚, distilled water was added dropwise. The reaction solution was filtered and then separated by column chromatography to obtain 29.5 g (yield 68%) of [intermediate 2-b].

Synthesis Example 2-3. [Synthesis of intermediate 2-c]

[Intermediate 1-d] [Intermediate 2-c]

Except that 4-bromo-1-iodobenzene was used instead of 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5 To obtain 22 g (yield 78%) of [intermediate 2-c].

Synthesis Example 2-4. Synthesis of [intermediate 2-d]

[Intermediate 2-c] [Intermediate 2-d]

20 g (47 mmol) of [intermediate 2-c] and 200 mL of tetrahydrofuran were added to a 500 mL reaction vessel, and then the temperature was cooled to -78 ° C under a nitrogen atmosphere. After 30 minutes, 32 mL (51.7 mmol) of 1.6 M n-butyllithium was slowly added dropwise, followed by stirring for 1 hour. 5.8 g (56.4 mmol) of trimethylborate was slowly added dropwise at -78 deg. C, and the temperature was raised to room temperature. After stirring for 2 hours, an aqueous hydrochloric acid solution was added to terminate the reaction, followed by distillation under reduced pressure. And recrystallized with hexane to obtain 14.7 g of [intermediate 2-d]. (Yield: 81%)

Synthesis Example 2-5. Synthesis of [Compound 25]

[Intermediate 2-d] [Intermediate 2-b] [Compound 25]

Synthesis was conducted in the same manner as in [Synthesis Example 1-2], except that [Intermediate 2-d] was used instead of [Intermediate 1-a] and [Intermediate 2-b] was used instead of 2-bromobenzaldehyde [Compound 25 ] (8 g, yield: 58%).

MS (MALDI-TOF): m / z 547.20 [M] &lt; + &

Synthesis Example 3. Synthesis of [Compound 39]

Synthesis Example 3-1. Synthesis of [intermediate 3-a]

                                               [Intermediate 3-a]

Instead of [Intermediate 1-d] used in Synthesis Example 1-5 and 1-bromocarbazole was used instead of 2- (4-bromophenyl) -4,6-diphenyl-1,3,5- Benzene was used to synthesize 36 g (yield 68%) of [intermediate 3-a].

Synthesis Example 3-2. Synthesis of [intermediate 3-b]

[Intermediate 3-a] [Intermediate 3-b]

31 g (yield 75%) of [intermediate 3-b] was obtained by the same method as Intermediate 3-a except for using [Intermediate 3-a] instead of 1-bromocarbazole used in Synthesis Example 1-1.

Synthesis Example 3-3. [Synthesis of intermediate 3-c]

[Intermediate 3-b] [Intermediate 3-c]

Synthesis was performed in the same manner as in [Synthesis Example 1-2], except that [Intermediate 3-b] was used instead of [Intermediate 1-a] and 2,5-dibromobenzaldehyde was used instead of 2-bromoaldehyde [Intermediate 3-c] (yield: 52%).

Synthesis Example 3-4. Synthesis of [intermediate 3-d]

[Intermediate 3-c] [Intermediate 3-d]

Except that [intermediate 3-c] was used in place of [intermediate 1-b] used in Synthesis Example 1-3 to obtain 22 g (yield 86%) of [intermediate 3-d].

Synthesis Example 3-5. Synthesis of [intermediate 3-e]

[Intermediate 3-d] [Intermediate 3-e]

(Yield 79%) was obtained by synthesizing [Intermediate 3-e] in the same manner as Intermediate 3-d except for using [Intermediate 3-d] instead of [Intermediate 1-c] used in Synthesis Examples 1-4.

Synthesis Example 3-6. [Synthesis of intermediate 3-f]

[Intermediate 3-e] [Intermediate 3-f]

(Yield: 84%) was obtained by the same method as Intermediate 3-e except for using [Intermediate 3-e] instead of [Intermediate 2-c] used in Synthesis Example 2-4.

Synthesis Example 3-7. Synthesis of [Compound 39]

[Intermediate 3-f] [Compound 39]

Except that [Intermediate 3-f] was used instead of [Intermediate 2-d] used in Synthesis Example 2-2 and 2-chloro-4,6-diphenyl-1,3,5-triazine Was synthesized in the same manner as in Example 1 to obtain 8 g (yield: 58%) of [Compound 39].

MS (MALDI-TOF): m / z 574.22 [M] &lt; + &

Synthesis Example 4. Synthesis of [Compound 67]

Synthesis Example 4-1. Synthesis of [Compound 67]

[Intermediate 4-a] [Compound 67]

[Intermediate 4-a] was synthesized in the same manner except that 2,6-dibromobenzaldehyde was used instead of 2,5-dibromobenzaldehyde used in Synthesis Example 3, and [Intermediate 4-a 3-f] was used in place of [Intermediate 4-a] to obtain 6 g (yield: 45%) of [Compound 67].

MS (MALDI-TOF): m / z 574.22 [M] &lt; + &

Synthesis Example 5. Synthesis of [Compound 104]

Synthesis Example 5-1. Synthesis of [intermediate 5-a]

                                     [Intermediate 5-a]

28 g (yield: 86%) was obtained by synthesizing [Intermediate 5-a], except that 1-bromo-9,9-dimethylfluorene was used in place of [Intermediate 2-c] used in Synthesis Example 2-4. ).

Synthesis Example 5-2. [Synthesis of intermediate 5-b]

[Intermediate 5-a] [Intermediate 5-b]

20 g (yield 68%) of [intermediate 5-b] was obtained by the same method except for using [Intermediate 5-a] instead of [Intermediate 1-a] used in Synthesis Example 1-2.

Synthesis Example 5-3. Synthesis of [intermediate 5-c]

[Intermediate 5-b] [Intermediate 5-c]

(Yield 82%) was obtained by synthesizing [Intermediate 5-c] in the same manner as Intermediate 5-b except for using [Intermediate 5-b] instead of [Intermediate 1-b] used in Synthesis Example 1-3.

Synthesis Example 5-4. Synthesis of [intermediate 5-d]

[Intermediate 5-c] [Intermediate 5-d]

(Yield 75%) was obtained by synthesizing [Intermediate 5-d] in the same manner as Intermediate 5-c except for using [Intermediate 5-c] instead of [Intermediate 1-c] used in Synthesis Examples 1-4.

Synthesis Example 5-5. Synthesis of [intermediate 5-e]

[Intermediate 5-d] [Intermediate 5-e]

15 g (50.9 mmol) of Intermediate 5-d and 150 ml of dichloromethane were placed in a 1 L reactor and stirred. Bromine (8.9 g, 56 mmol) was slowly added dropwise at room temperature, followed by stirring for 5 hours. After completion of the reaction, precipitation was carried out using methanol and filtration was conducted to obtain 9.9 g of [intermediate 5-e]. (Yield: 52%)

Synthesis Example 5-6. [Synthesis of intermediate 5-f]

    [Intermediate 5-e] [Intermediate 5-f]

(Yield 88%) was obtained by synthesizing [Intermediate 5-f] in the same manner as Intermediate 5-e except for using [Intermediate 5-e] instead of [Intermediate 2-c] used in Synthesis Example 2-4.

Synthesis Example 5-7. Synthesis of [Compound 104]

[Intermediate 5-f] [Compound 104]

6 g (yield 65%) of [Compound 104] was obtained by the same method as Intermediate 5-f except for using Intermediate 5-f instead of Intermediate 3-f used in Synthesis Example 3-7.

MS (MALDI-TOF): m / z 525.22 [M] &lt; + &

Synthesis Example 6. Synthesis of [Compound 116]

Synthesis Example 6-1. [Synthesis of intermediate 6-b]

 [Intermediate 6-a] [Intermediate 6-b]

[Intermediate 6-a] was synthesized in the same manner except that 2,5-dibromobenzaldehyde was used instead of 2-bromobenzaldehyde used in Synthesis Example 5, and [Intermediate 2- 14 g (yield: 79%) of [intermediate 6-b] was obtained by the same method as in [Intermediate 6-a]

Synthesis Example 6-2. Synthesis of [Compound 116]

[Intermediate 6-b] [Compound 116]

Was synthesized in the same manner as in [Synthesis Example 3-7], except that [Intermediate 6-b] was used instead of [Intermediate 3-f] used in Synthesis Example 3-7 to obtain 7.8 g (Yield: 44%) of [Compound 116].

MS (MALDI-TOF): m / z 525.22 [M] &lt; + &

Synthesis Example 7. Synthesis of [Compound 139]

Synthesis Example 7-1. Synthesis of [Compound 139]

[Intermediate 7-a] [Compound 139]

[Intermediate 7-a] was synthesized in the same manner except that 2,5-dibromobenzaldehyde was used instead of 2-bromobenzaldehyde used in Synthesis Example 5, and [Intermediate 2- c] was used in place of [Intermediate 7-a], 14 g (yield 79%) of [Compound 139] was obtained.

MS (MALDI-TOF): m / z 525.22 [M] &lt; + &

Synthesis Example 8. Synthesis of [Compound 155]

Synthesis Example 8-1. [Synthesis of intermediate 8-a]

                                        [Intermediate 8-a]

40 g (236 mmol) of diphenylamine was dissolved in 400 mL of dimethylformamide, and the mixture was stirred at 0 占 폚. 82 g (461 mmol) of N-bromosuccinimide was slowly added to the reactor, and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, H 2 O was added dropwise at room temperature. When brown crystals were formed, the mixture was filtered and then recrystallized from toluene and methanol to obtain 40 g of [intermediate 8-a]. (Yield 60%)

Synthesis Example 8-2. Synthesis of [Intermediate 8-b]

[Intermediate 8-a] [Intermediate 8-b]

12 g (37 mmol) of intermediate 8-a, 10 g (81 mmol) of phenylboronic acid, 15.2 g (11 mmol) of potassium carbonate, 1.7 g (1 mmol) of tetrakistriphenylphosphine palladium, 40 mL of H2O, 100 mL of toluene and 100 mL of 1,4-dioxane were added, and the mixture was refluxed with stirring for 24 hours. After completion of the reaction, the reaction product was separated, and the organic layer was concentrated under reduced pressure and then recrystallized to obtain 9.9 g of Intermediate 8-b. (Yield: 75%)

Synthesis Example 8-3. [Synthesis of intermediate 8-c]

[Intermediate 8-b] [Intermediate 8-c]

A solution of 7.9 g (24.6 mmol) of Intermediate 8-b, 8.3 g (30 mmol) of 4-bromoiodobenzene, 0.4 g (0.3 mmol) of palladium acetate and 4.2 g (43 mmol) of sodium tert- , 0.1 g (0.3 mmol) of triturated butylphosphine and 100 ml of toluene, 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 4.0 g of [Intermediate 8-c]. (Yield: 45%)

Synthesis Example 8-4. Synthesis of [Compound 155]

 [Intermediate 6-b] [Intermediate 8-c] [Compound 155]

Was synthesized in the same manner as in Synthesis Example 6-2, except that [Intermediate 8-c] was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 6-2 to obtain 5.8 g (Yield: 52%).

MS (MALDI-TOF): m / z 689.31 [M] &lt; + &

Synthesis Example 9. Synthesis of [Compound 168]

Synthesis Example 9-1. Synthesis of [Compound 168]

  [Intermediate 5-f] [Intermediate 8-c] [Compound 168]

Synthesis was conducted in the same manner as in Synthesis Example 8-4, except that [Intermediate 5-f] was used in place of [Intermediate 6-b] to obtain 7.1 g (yield: 55%) of [Compound 168].

MS (MALDI-TOF): m / z 689.31 [M] &lt; + &

Synthesis Example 10. Synthesis of [Compound 184]

Synthesis Example 10-1. Synthesis of [Compound 184]

[Intermediate 7-a] [Intermediate 8-c] [Compound 184]

Synthesis was conducted in the same manner as in Synthesis Example 8-4, except that [Intermediate 7-a] was used instead of [Intermediate 6-b] to obtain 6.4 g (yield 48%) of [Compound 184].

MS (MALDI-TOF): m / z 689.31 [M] &lt; + &

Examples 1 to 4 (phosphorescent host applications)

Manufacture of organic light-emitting diodes

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 compound ET: Liq = 1: 1 (300 Å), Liq (10 Å) and Al (1,000 Å) were deposited in this order.

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

     [HATCN] [NPD] [RD]

        [ET] [Liq]

Comparative Example 1

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

        [BAlq]

The voltage, luminance, color coordinates and lifetime 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. T95 means the time required for the luminance to be reduced to 95% at the initial luminance (3000 cd / m ² ).

division Host V Cd / A CIEx CIEy T ₉₅ (Hr) Comparative Example 1 BAlq 6.22 14.7 0.665 0.334 40 Example 1 Compound 2 4.6 21.3 0.664 0.335 140 Example 2 Compound 25 4.2 20.8 0.664 0.335 125 Example 3 Compound 39 4.3 22.1 0.664 0.335 145 Example 4 Compound 37 4.1 22.8 0.666 0.333 150

As shown in Table 1, the organic compound obtained according to the present invention has higher efficiency, lower driving voltage and longer lifetime than BAlq, which is widely used as a phosphorescent host material.

Examples 5 to 7 (Use for electron transport layer)

Manufacture of organic light-emitting diodes

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 deposited on the ITO using HATCN (50 Å), NPD (650 Å), [BH] + Blue dopant (300 Å), Liq (10 Å), and Al (1,000 Å) were deposited in this order and measured at 0.4 mA.

The structures of [BH] and [BD] are as follows

    [BH] [BD]

Comparative Example 2

The organic light emitting device for Comparative Example 2 was fabricated in the same manner except that ET, which is generally used as an electron transport layer material, was used in place of the compound produced by the invention in the device structure of the embodiment.

The voltage, luminance, color coordinates and lifetime of the organic light emitting device manufactured according to Examples 5 to 7 and Comparative Example 2 were measured, and the results are shown in Table 2 below. T95 means the time required for the luminance to be reduced to 95% compared with the initial luminance (2000 cd / m ² )

division ETL V Cd / A CIEx CIEy T ₉₅ (Hrs) Comparative Example 2 ET 4.3 6.5 0.133 0.129 13 Example 5 Compound 104 3.8 7.8 0.133 0.129 28 Example 6 Compound 116 3.7 8.4 0.132 0.130 38 Example 7 Compound 139 3.8 8.2 0.132 0.128 34

As shown in Table 2, the organic compound obtained according to the present invention has higher efficiency, lower driving voltage and longer life than ET, which is widely used as an electron transport layer material.

Examples 8 to 10 (Use of the hole transport layer)

Manufacture of organic light-emitting diodes

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 coated on the ITO using HATCN (50 Å) as a hole transporting layer, the compound (650 Å) Doped with a host (BH) + blue dopant (BD) of 5% to form a 200 Å thick light emitting layer. Then, the compound ET: Liq = 1: 1 (300 ANGSTROM) and the electron injecting layer Liq (10 ANGSTROM) and Al (1,000 ANGSTROM) were sequentially deposited as the electron transporting layer.

Comparative Example 3

The organic light emitting device for Comparative Example 3 was fabricated in the same manner as in Examples 8 to 10 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.

The voltage, luminance, color coordinates and lifetime of the organic EL device manufactured according to Examples 8 to 10 and Comparative Example 3 were measured, and the results are shown in Table 3 below. T95 means 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 3 NPD 4.3 6.5 0.133 0.129 13 Example 8 Formula 155 3.6 8.4 0.133 0.129 33 Example 9 168 3.8 8.1 0.132 0.130 30 Example 10 184 3.8 8.5 0.133 0.128 29

As shown in Table 3, the organic compound obtained according to the present invention has higher efficiency, lower driving voltage and longer life than NPD, which is widely used as a hole transport layer material.

Claims (19)

An organic compound represented by the following formula (A) or (B).
(A)

[Chemical Formula B]

In the above formulas (A) and (B)
Wherein X is CR21R22 or NR23,
The substituents R 1 to R 12 are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, 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 C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C5 to C30 cycloalkenyl group, A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms, , A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom, a cyano group, a nitro group, a halogen group, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms , A substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, a substituted or unsubstituted aluminum group, a carbonyl group, a phosphoryl group, an amino group, a thiol group, a hydroxyl group, a selenium group, a tellurium group, An ester group,
R21 to R23 are the same or different from each other and each independently represents hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3- Lt; RTI ID = 0.0 &gt; to 50 &lt; / RTI &gt; heteroaryl groups,
In the above formula (A), one or two substituents of the substituents R 1 to R 12 and the substituent R 23 are a single bond bonded to the above-mentioned A 1,
In the above formula (B), one or two substituents of the substituents R 1 to R 12 are a single bond bonding to the A 2, Ar 2 and L 2 in the A 2 may be connected to each other to form a condensed ring, and Ar 3 and L 2 They may be connected to each other to form a condensed ring,
The linking groups L 1 and L 2 are the same or different and independently represent a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted C2- A substituted or unsubstituted C2-C60 alkynylene group, a substituted or unsubstituted C3-C60 cycloalkylene group, a substituted or unsubstituted C2-C60 heterocycloalkylene group, a substituted or unsubstituted C6-C60 arylene group, Or an unsubstituted heteroarylene group having 2 to 60 carbon atoms;
n and m are the same or different and independently of each other an integer of 0 to 3, and when each of these is 2 or more, each of the linking groups L1 and L2 is the same or different from each other,
Each of Ar 1 to Ar 3 is the same or different and independently represents a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 40 carbon atoms A substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms,
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,
The substituents Ar1 to Ar3 in the above-mentioned [Formula A] and [Formula B] 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 heteroaryl having 2 to 30 carbon atoms Wherein R &lt; 1 &gt; and R &lt; 2 &gt; The method according to claim 1,
Wherein Ar 1 in the above [Formula A] is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. The method according to claim 1,
Ar2 and Ar3 in the above formula (B) are the same or different and independently of each other, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. The method of claim 3,
Wherein the substituent Ar1 in the above formula (A) is any one selected from the following structural formulas A to S.
[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]

[Structural formula P] [Structural formula Q]

[Structural formula R] [Structural formula S]

The substituents R in the structural formulas A to S are the same as those of R 1 to R 12 defined in claim 1,
K is an integer of 1 to 7, and when k is 2 or more, each R is the same or different,
When k is 2 or more, each substituent R may be bonded to adjacent substituent R to form a saturated or unsaturated ring. The method according to claim 1,
In the above-mentioned formula (A), one of the substituents R 1 to R 12 and the substituent R 23 is a single bond which binds to the above-mentioned Al,
Wherein, in the above formula (B), one of the substituents R 1 to R 12 is a single bond which binds to the above-mentioned A 2. The method according to claim 6,
In the above Formulas A and B,
Wherein one of the substituents R 1 to R 4 is a single bond bonded to A 1 or A 2. The method according to claim 6,
Wherein in the above formulas A and B, one of the substituents R5 to R12 is a single bond bonding with Al or A2. The method according to claim 6,
In the above formula (A), the substituent R23 is a single bond to be bonded to Al. The method according to claim 1,
Wherein the substituent which is not connected to A1 or A2 among the substituents R1 to R12 is hydrogen or deuterium. The method according to claim 1,
Wherein the linking groups L 1 and L 2 are the same or different and are each independently 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,
Wherein the compound represented by the above formula (A) or (B) is any one selected from the group consisting of the following compounds [1] to [192].
<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 &

<Compound 89><Compound90><Compound91><Compound92>

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

&Lt; Compound 97 >< 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>

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 the organic compound according to any one of claims 1 to 12. 14. The method of claim 13,
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. 14. The method of claim 13,
Wherein the light emitting layer comprises a phosphorescent host and a phosphorescent dopant, and the organic compound is used as a phosphorescent host. 14. The method of claim 13,
Wherein the organic compound is used for a hole transport layer. 14. The method of claim 13,
Wherein the organic compound is used for an electron transport layer. 15. The method of claim 14,
Wherein at least one layer selected from the respective layers is formed by a deposition process or a solution process. 14. The method of claim 13,
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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