KR20190061314A - Novel organic compounds derivatives and organic light-emitting diode therewith - Google Patents

Abstract

The present invention relates to an organic compound represented by chemical formula A and an organic light emitting element comprising the same. In the chemical formula A, Q1, Q2, and Ar_1 to Ar_4 are the same as described in the description of the invention. The organic light emitting element according to the present invention can have high efficiency, a low voltage, and a long lifespan characteristic compared to an existing organic light emitting element.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel organic compound and an organic light emitting diode (OLED)

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

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

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

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

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

Of these, as a conventional technique relating to an electron transporting layer material, the disclosure of Japanese Patent Laid-Open Publication No. 10-2012-010420 (2012.09.20) has an excellent electron transporting ability and a hole blocking ability and is excellent in luminous efficiency, In order to prepare this high organic compound, an organic compound in which a pyridoindole derivative is bonded to a substituted anthracene ring structure has been described. In JP-A-2010-168363 (2010.08.05), external quantum efficiency and drive Discloses an anthracene derivative having a pyridine naphthyl group, which has excellent characteristics of voltage characteristics.

Further, as a prior art document showing improved properties by providing a hole-assisted layer between the light-emitting layer and the electron-transporting layer, in Patent Document 10-2016-0012066 (2016.02.02), an amine compound is used as an auxiliary layer in the hole- Described is a technique to be used.

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 a material that can be used as an electron transporting layer or a hole assisting layer for a light emitting device and an organic light emitting device including the same.

Japanese Patent Application Laid-Open No. 10-2012-0104204 (2012.09.20) Japanese Unexamined Patent Application Publication No. 2010-168363 (Aug. 05, 2010) Japanese Patent Application Laid-Open No. 10-2016-0012066 (Feb.

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

A second object of the present invention is to provide a novel organic light emitting device including the organic compound in a hole-transporting layer or an electron transporting layer.

The present invention provides an organic compound represented by the following formula (A) to achieve the above technical problems.

(A)

In the above formula (A)

Wherein Q1 and Q2 are the same or different and 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,

Each of Ar 1 to Ar 4 is the same or different and is 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-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 arylthio group, a substituted or unsubstituted C1-C30 alkylamine 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 A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having 0, 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 aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, , Or any one of substituents selected from the following formulas [A] to [Q], wherein one of Ar1 to Ar4 is any one selected from the following Structural Formulas A to Q Lt; / RTI >

In the aromatic hydrocarbon ring or aromatic heterocycle of Q1 and Q2 and the two benzene rings located in the lower part of the formula A, the carbon atoms of the aromatic ring not bonded to Ar1 to Ar4 are each bonded to hydrogen or deuterium,

 [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]

In the above Structural Formulas A to Q,

The linking groups L1 to L3 are the same or different and independently of each other, a single bond, 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 A substituted or unsubstituted alkylene group having 2 to 60 carbon atoms, an alkynylene 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 Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms,

Each of p1 to p3 is an integer of 1 to 3, and when each of them is 2 or more, each of the linking groups L1 to L3 is the same or different from each other,

Each of R 1 to R 9 is the same or different and is 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-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 arylthio group, a substituted or unsubstituted C1-C30 alkylamine 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 A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having 0, N or S, 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 aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, , ≪ / RTI >

And the carbon atom of the formed alicyclic or aromatic monocyclic or polycyclic ring may be any one or more selected from N, S, and O, and the carbon atom of the alicyclic or aromatic monocyclic or polycyclic ring may form a monocyclic or polycyclic ring of alicyclic or aromatic, Which may be substituted by a heteroatom,

The substituent Ra in the formula [Q] is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom,

'- *' means a single bond bonded to Q1, Q2 or the carbon atom of two benzene rings located in the lower part of formula (A).

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 represented by the formula (A) according to the present invention .

The organic light emitting device comprising the compound represented by the formula (A) in the electron transport layer or the hole-assist layer according to the present invention can have high efficiency, low voltage and long life characteristics as compared with the conventional organic light emitting device.

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

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

The organic compound according to the present invention has a structure represented by the following formula (A).

(A)

In the above formula (A)

Wherein Q1 and Q2 are the same or different and 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,

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 alkynyl group having 2 to 30 carbon atoms, , A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon number of 6 to 30 A substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 arylthio group, a substituted or unsubstituted C1-C30 alkylamine group, A substituted or unsubstituted aryl 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 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 aryl group having 2 to 50 carbon atoms, A group selected from the group consisting of a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, Or one of substituents selected from the following formulas [A] to [Q], wherein one of Ar1 to Ar4 is any substituent selected from the following Structural Formulas A to Q,

In the aromatic hydrocarbon ring or aromatic heterocycle of Q1 and Q2 and the two benzene rings located in the lower part of the formula A, the carbon atoms of the aromatic ring not bonded to Ar1 to Ar4 are each bonded to hydrogen or deuterium,

[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]

In the above Structural Formulas A to Q,

The linking groups L1 to L3 are the same or different and independently of each other, a single bond, 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 A substituted or unsubstituted alkylene group having 2 to 60 carbon atoms, an alkynylene 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 Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms,

Each of p1 to p3 is an integer of 1 to 3, and when each of them is 2 or more, each of the linking groups L1 to L3 is the same or different from each other,

Each of R 1 to R 9 is the same or different and is 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-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 arylthio group, a substituted or unsubstituted C1-C30 alkylamine 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 A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having 0, N or S, 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 aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, , ≪ / RTI >

And the carbon atom of the formed alicyclic or aromatic monocyclic or polycyclic ring may be any one or more selected from N, S, and O, and the carbon atom of the alicyclic or aromatic monocyclic or polycyclic ring may form a monocyclic or polycyclic ring of alicyclic or aromatic, Which may be substituted by a heteroatom,

The substituent Ra in the formula [Q] is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom,

Represents a single bond which is bonded to the carbon atoms of two benzene rings located at the bottom of Q1, Q2 or the formula (A)

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 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, An aryloxy group, an aryloxy group, an arylsilyl group, and an aryloxy group having 6 to 24 carbon atoms.

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

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

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

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

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

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

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

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

The organic compound represented by the above formula (A) according to the present invention has two rings (Q1 and Q2 rings connected to Ar1 or Ar2) in the upper part of the above formula (A) are the same or different, Or an unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 40 carbon atoms, and the Q1 and Q2 rings and two rings (Ar3 or Ar4) Only one of the benzene rings to be connected is bonded to any one substituent selected from the following Structural Formulas A to Q, and the organic compound is a hole-transporting layer or an electron transporting layer material in the organic light- When used, it can have high efficiency, low voltage and long life characteristics.

In one embodiment, Q1 and Q2 are each independently a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms, wherein at least one of Q1 and Q2 is phenanthrene , Triphenylene, and pyrene.

When Q1 and Q2 are substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 carbon atoms, one of Q1 and Q2 is any aromatic hydrocarbon ring selected from phenanthrene, triphenylene and pyrene, And the other one may be a benzene ring or a naphthalene ring, more preferably one of Q1 and Q2 is any one aromatic hydrocarbon ring selected from phenanthrene, triphenylene and pyrene, and the other is a benzene ring have.

In the compound represented by the formula (A) according to the present invention, the linking groups L1 to L3 are the same or different and independently of one another, or may be a single bond or a group represented by the following formulas (22) to (30) , And p, q and r may be 1 or 2, respectively.

[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]

In the structural formulas 22 to 30, the carbon of the aromatic ring may be bonded to hydrogen or deuterium.

As preferred examples of Ar1 to Ar4 in the compound represented by the formula (A) according to the present invention, each of Ar1 to Ar4 is the same or different and is independently selected from the group consisting of hydrogen, deuterium, And any one of Ar 1 to Ar 4 may be any one substituent selected from the following Structural Formulas A to Q:

In addition, one of Ar1 to Ar4 may be [Structural Formula A].

In addition, one of Ar1 to Ar4 may be any one of [structural formulas B] to [structural formula H]. And one of Ar1 to Ar4 may be any one of [structural formulas I] to [structural formula P].

Further, as a preferred example of the structural formula Q in the organic compound represented by the formula (A) according to the present invention, Ra represents a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted carbazole, a substituted or unsubstituted dibenzothiophene Substituted or unsubstituted fluorene, and in this case, the benzene ring carbon atom in the dibenzofuran, carbazole, dibenzothiophene and fluorene, or the nitrogen atom of the carbazole or the 9-position carbon atom of the fluorene And may be bonded to L3 in the formula (Q).

Meanwhile, specific examples of the organic compound represented by the above formula (A) according to the present invention may be a compound represented by any one selected from the following [compounds 1] to [232], but are not limited thereto.

<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>

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

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

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

<Compound 205> <Compound 206> <Compound 207> <Compound 208>

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

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

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

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

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

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

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 an organic compound represented by the formula (A) according to the present invention as described above, Device.

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 injecting layer, a hole transporting 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 preferably the organic compound of the present invention can be used for a hole-assisted layer or for an electron-transport layer.

The organic light emitting device according to the present invention can have high efficiency, low voltage driving, and long life time characteristics when the organic compound represented by the above formula (A) is used for the hole assist layer or for the electron transport layer.

The material for the hole transport layer used in the organic light emitting device according to the present invention is not particularly limited as long as it is commonly used in the art and includes, for example, N, N'-bis (3-methylphenyl) (TPD) or N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine (a-NPD ) Can be used. However, the present invention is not necessarily limited thereto.

A HIL (Hole Injection Layer) may be further deposited on the lower portion of the hole transport layer. As the hole injection layer, a copper phthalocyanine (CuPc) or a starburst type amine TCTA 4,4 ', 4 "-tri (N-carbazolyl) triphenyl-amine and m-MTDATA (4,4', 4" -tris- (3-methylphenylphenylamino) triphenylamine).

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

[Formula H] &lt;

In the above formula (H)

X ₁ to X ₁₀ are the same or different from each other and each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms , A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted 5 A substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S, a substituted or unsubstituted hetero atom, a substituted Is a group selected from the group consisting of an unsubstituted silicon group, a substituted or unsubstituted boron group, a substituted or unsubstituted silane group, a carbonyl group, a phosphoryl group, an amino group, a nitrile group, a hydroxyl group, a nitro group, a halogen group, an amide group and an ester group And the groups adjacent to each other may form a condensed ring of an aliphatic, aromatic, aliphatic hetero or aromatic hetero.

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

[Compound 301] [Compound 302] [Compound 303] [Compound 304]

[Compound 305] [Compound 306] [Compound 307] [Compound 308]

[Compound 309] [Compound 310] [Compound 311] [Compound 312]

[Compound 213] [Compound 214] [Compound 215] [Compound 216]

[Compound 317] [Compound 318] [Compound 319] [Compound 320]

[Compound 321] [Compound 322] [Compound 323] [Compound 324]

[Compound 325] [Compound 326] [Compound 327] [Compound 328]

[Compound 329] [Compound 330] [Compound 331] [Compound 332]

[Compound 333] [Compound 334] [Compound 335] [Compound 336]

[Compound 337] [Compound 338] [Compound 339] [Compound 340]

[Compound 341] [Compound 342] [Compound 343] [Compound 344]

[Compound 345] [Compound 346] [Compound 347] [Compound 348]

[Compound 349] [Compound 350] [Compound 351] [Compound 352]

[Compound 353] [Compound 354] [Compound 355] [Compound 356]

[Compound 357] [Compound 358] [Compound 359] [Compound 360]

[Compound 361] [Compound 362] [Compound 363] [Compound 364]

[Compound 365] [Compound 366] [Compound 367] [Compound 368]

[Compound 369] [Compound 370] [Compound 371] [Compound 372]

[Compound 373] [Compound 374] [Compound 375] [Compound 376]

[Compound 377] [Compound 378] [Compound 379] [Compound 380]

[Compound 381] [Compound 382] [Compound 383] [Compound 384]

[Compound 385] [Compound 386] [Compound 387] [Compound 388]

[Compound 389] [Compound 390] [Compound 391] [Compound 392]

[Compound 393] [Compound 394] [Compound 395] [Compound 396]

[Compound 397] [Compound 398] [Compound 399] [Compound 400]

[Compound 401] [Compound 402] [Compound 403] [Compound 404]

[Compound 405] [Compound 406] [Compound 407] [Compound 408]

[Compound 409] [Compound 410] [Compound 411] [Compound 412]

[Compound 413] [Compound 414] [Compound 415] [Compound 416]

[Compound 417] [Compound 418] [Compound 419] [Compound 420]

[Compound 421] [Compound 422] [Compound 423] [Compound 424]

[Compound 425] [Compound 426] [Compound 427] [Compound 428]

[Compound 429] [Compound 430] [Compound 431] [Compound 432]

[Compound 433] [Compound 434] [Compound 435] [Compound 436]

[Compound 437] [Compound 438] [Compound 439] [Compound 440]

[Compound 441] [Compound 442] [Compound 443] [Compound 444]

[Compound 445] [Compound 446] [Compound 447] [Compound 448]

[Compound 449] [Compound 450] [Compound 451] [Compound 452]

[Compound 453] [Compound 454] [Compound 455] [Compound 456]

[Compound 457] [Compound 458] [Compound 459] [Compound 460]

[Compound 461] [Compound 462] [Compound 463] [Compound 464]

[Compound 465] [Compound 466] [Compound 467] [Compound 468]

[Compound 469] [Compound 470] [Compound 471] [Compound 472]

[Compound 473] [Compound 474] [Compound 475] [Compound 476]

[Compound 477] [Compound 478] [Compound 479] [Compound 480]

[Compound 481] [Compound 482] [Compound 483] [Compound 484]

[Compound 485] [Compound 486] [Compound 487] [Compound 488]

[Compound 489] [Compound 490] [Compound 491] [Compound 492]

[Compound 493] [Compound 494] [Compound 495] [Compound 496]

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

            [Chemical Formula 1] &lt; EMI ID =

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

A is a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, an optionally substituted arylene group having 6 to 60 carbon atoms , A substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms having a hetero atom O, N or S, and the like.

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

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

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

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

(A10)

Wherein Z ₁ to Z ₂ in the formula [A3] are each independently selected from the group consisting of hydrogen, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted Or an unsubstituted or substituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted aryl group having 2 to 60 carbon atoms (Substituted or unsubstituted C1-C60 alkyl) amino group, or a substituted or unsubstituted C6-C60 aryl) amino group, a substituted or unsubstituted C1-C60 alkylamino group, , (Substituted or unsubstituted aryl group having 6 to 60 carbon atoms) amino group, and Z ₁ to Z ₂ are the same or different from each other and can form a condensed ring with adjacent groups.

In the above formula (1)

X ₁ and X ₂ are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a single bond, X ₁ and X ₂ may be bonded to each other,

Y ₁ and Y ₂ are each independently a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted Or a substituted or unsubstituted C1 to C24 heteroalkyl group, a substituted or unsubstituted C3 to C24 cycloalkyl group, a substituted or unsubstituted C1 to C24 alkoxy group, a cyano group, a halogen group, a substituted or unsubstituted carbon number A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron, deuterium, and hydrogen. more selected species and, Y ₁ to Y ₂ each are the same or different each other, may form a fused ring group of the aliphatic, aromatic, aliphatic hetero, or aromatic heterocyclic group which are adjacent to each other It was.

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

In the above formula (2)

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

In addition, Is a single bond or - [C (R ₅ ) (R ₆ )] _p -, and p is an integer of 1 to 3; when p is 2 or more, R ₅ and R ₆ are the same or different from each other;

Wherein _{R 1, R 2, R 3} , R 5 and R ₆ are, each independently, hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms , A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, Or beach (Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms), a di (substituted or unsubstituted alkyl group having 1 to 60 carbon atoms) amino group, a substituted or unsubstituted amino group having 6 to 60 carbon atoms, An aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron,

a is an integer of 1 to 4, and when a is 2 or more, R ₃ of 2 or more are the same or different, and when R ₃ is plural, each R ₃ may be in fused form, and n is 1 to 4 It is an integer.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[Substituent 52]

In the above substituents, R may be the same or different from each other and is selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted C1 to C60 alkoxy group, A substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, (Substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, or a substituted or unsubstituted aryl (having 6 to 60 carbon atoms) amino group, di (substituted or unsubstituted A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron, and each has 1 To 12 carbon atoms, and each of the substituents may form a condensed ring with adjacent groups.

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

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

In the meantime, the electron transporting layer used in the present invention can use the organic compound according to the present invention alone or in combination with a known compound.

The material for the electron transport layer that can be mixed when the electron transport layer is used in combination with the organic compound of the present invention can be used as long as it functions to stably transport electrons injected from the electron injection electrode, A known electron transporting material can be used.

Examples of such known electron transporting materials include quinoline derivatives, especially tris (8-quinolinolate) aluminum (Alq3), TAZ, BAlq, beryllium bis (benzoquinolin-10 -olate: Bebq2), compound 501, compound 502, BCP, oxadiazole derivative PBD, BMD, BND, and the like may be used, but the present invention is not limited thereto.

TAZ BAlq

&Lt; Compound 501 > < Compound 502 > BCP

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 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 The material for forming the electron injection layer may be any material known as an electron injection layer forming material such as CsF, NaF, LiF, NaCl, Li ₂ O, BaO, or the like as an electron injection layer forming material, as long as it is commonly used in the art. Materials 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, a cathode is present on the electron injection layer, and the cathode is formed of a material selected from the group consisting of Li, Mg, Al, Al-Li, Ca, (Mg-In) and magnesium-silver (Mg-Ag), or a transmissive negative electrode using ITO or IZO can be used to obtain a top light 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, a hole assisting layer 45, an organic light emitting layer 50, an electron transport layer 60, and a cathode 80, The electron injection layer 70 and the injection layer 30 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.

Subsequently, a hole-assist layer 45 is formed on the hole-transport layer 40, an organic light-emitting layer 50 is formed on the hole-assist layer 45, A thin film can be formed as a vacuum deposition method or a spin coating method using a hole blocking layer (not shown). 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 17

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

                                         [Intermediate 1-a]

4-Chlorophenol (50 g, 389 mmol), 1-bromo-2-fluorobenzene (68.1 g, 389 mmol) and potassium carbonate (80.7 g, 583 mmol) ml &lt; / RTI &gt; and stirred at 150 &lt; 0 &gt; C for 12 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure and then subjected to column separation to obtain [intermediate 1-a]. (71.5 g, 65%).

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

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

Under nitrogen conditions, a solution of intermediate [1-a] (50 g, 176 mmol), 9-fluorenone (63.6 g, 352 mmol), tetrakis (triphenylphosphine) palladium (4.1 g, 3.5 mmol), trifluoromethanesulfonic acid (52.9 g, 352 mmol) were added to 500 ml of toluene, and the mixture was stirred at 110 ° C for 24 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure and then subjected to column separation to obtain [Intermediate 1-b] (50.5 g, 78%).

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

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

(50 g, 136 mmol), bis (pinacolato) diborane (51.9 g, 204 mmol), (diphenylphosphinoferrocene) palladium dichloride (5 g, 6.8 mmol) and potassium acetate 40.1 g, 408 mmol) were added to 500 ml of toluene and stirred for 12 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure and then subjected to column separation to obtain [intermediate 1-c]. (46.8 g, 75%)

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

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

(25 g, 98 mmol), tetrakis (triphenylphosphine) palladium (2.3 g, 2 mmol), potassium carbonate (40.7 g, g, 294 mmol), 500 mL of toluene and 150 mL of distilled water, and the mixture was stirred at 100 ° C for 12 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure and then subjected to column separation to obtain [intermediate 1-d]. (31.8 g, 63%).

.

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

[Intermediate 1-d] [Intermediate 1-e]

Potassium tertiary butoxide (9.8 g, 87 mmol) and 100 ml of tetrahydrofuran were stirred under nitrogen and cooled to 0 占 폚. (Methoxymethyl) triphenylphosphonium chloride (29.9 g, 87 mmol) were dissolved in 150 ml of tetrahydrofuran, and the mixture was stirred for 30 minutes. [Intermediate 1-d] (30 g, 58 mmol) was dissolved in 300 ml of tetrahydrofuran, and the mixture was slowly added dropwise, followed by stirring at room temperature for 2 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure and then subjected to column separation to obtain [Formula 1-e]. (29.1 g, 92%).

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

[Intermediate 1-e] [Intermediate 1-f]

300 ml of 1,2-dichloroethane was added to a solution of [intermediate 1-e] (29 g, 55 mmol) and bismuth (III) trifluoromethanesulfonate (1.8 g, 2.8 mmol) under nitrogen atmosphere and the mixture was stirred at room temperature for 3 hours . After completion of the reaction, methyl alcohol was used to form a precipitate, and the solid was filtered to obtain [intermediate 1-f]. (23.2 g, 82%)

Synthesis Example 1- (7): Synthesis of Compound 17

[Intermediate 1-f] [Compound 17]

(10 g, 19.6 mmol), bis (4-biphenyl) amine (6.3 g, 19.6 mmol), bisdibenzylidene acetone dipalladium (0.2 g, 0.4 mmol), BINAP g, 0.8 mmol) and sodium tertiary butylate (3.8 g, 39.1 mmol) were added to 100 ml of toluene and refluxed for 12 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure and then subjected to column separation to obtain [Compound 17]. (11.8 g, 72%).

MS (MALDI-TOF): m / z 751.29 [M ^&lt; ⁺ &^gt;].

Synthesis Example 2. Synthesis of Compound 18

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

                                              [Intermediate 2-a]

(68 g, 69%) was obtained in the same manner except that 3-chlorophenol was used in place of the 4-chlorophenol used in the above Synthesis Example 1- (1) to obtain Intermediate 2-a.

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

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

Was synthesized in the same manner as Intermediate 2-b except for using [Intermediate 2-a] instead of [Intermediate 1-a] used in Synthesis Example 1- (2). (57 g, 72%).

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

[Intermediate 2-b] [Intermediate 2-c]

Intermediate 2-c] was obtained in the same manner as Intermediate 2-b except for using [Intermediate 2-b] instead of [Intermediate 1-b] used in Synthesis Example 1- (3). (33 g, 73%).

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

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

Was synthesized in the same manner as Intermediate 2-d except for using [Intermediate 2-c] instead of [Intermediate 1-c] used in Synthesis Example 1- (4). (28 g, 62%).

Synthesis Example 2- (5): Synthesis of Intermediate 2-e

[Intermediate 2-d] [Intermediate 2-e]

Was synthesized in the same manner as Intermediate 2-e except for using [Intermediate 2-d] instead of [Intermediate 1-d] used in Synthesis Example 1- (5). (25 g, 88%).

Synthesis Example 2- (6): Synthesis of intermediate 2-f

[Intermediate 2-e] [Intermediate 2-f]

Was synthesized in the same manner as Intermediate 2-f except for using [Intermediate 2-e] instead of [Intermediate 1-e] used in Synthesis Example 1- (6). (20 g, 85%).

Synthesis Example 2- (7): Synthesis of Compound 18

[Intermediate 2-f] [Compound 18]

[Compound 18] was obtained by the same method except for using [Intermediate 2-f] instead of [Intermediate 1-f] used in Synthesis Example 1- (7). (12 g, 69%).

MS (MALDI-TOF): m / z 751.29 [M ^&lt; ⁺ &^gt;].

Synthesis Example 3. Synthesis of Compound 28

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

[Intermediate 2-c] [Intermediate 3-a]

Dibromobenzaldehyde was used instead of 2,5-dibromobenzaldehyde used in Synthesis Example 2- (4) to obtain [Intermediate 3-a]. (29 g, 59%).

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

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

Was synthesized in the same manner as Intermediate 3-b except for using [Intermediate 3-a] instead of [Intermediate 1-d] used in Synthesis Example 1- (5). (26 g, 89%).

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

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

Intermediate 3-c] was obtained in the same manner as Intermediate 3-b except for using [Intermediate 3-b] instead of [Intermediate 1-e] used in Synthesis Example 1- (6). (20 g, 83%).

Synthesis Example 3- (4): Synthesis of Compound 28

[Intermediate 3-c] [Compound 28]

Synthesis Example 1- (7) using [Intermediate 1-f] instead use the intermediate 3-c] and bis (4-biphenyl) amine instead of bis (9,9-dimethyl -9 H in-fluorene -7 -Yl) -amine was used in place of diethylamine to give [compound 28]. (13 g, 65%)

MS (MALDI-TOF): m / z 831.35 [M ^&lt; ⁺ &^gt;].

Synthesis Example 4. Synthesis of Compound 57

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

                                           [Intermediate 4-a]

Was synthesized in the same manner as in Synthesis Example 1- (1), except that 2-chlorophenol was used in place of 4-chlorophenol, to thereby give [Intermediate 4-a]. (52 g, 66%).

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

[Intermediate 4-a] [Intermediate 4-b]

Was synthesized in the same manner as Intermediate 4-b except for using [Intermediate 4-a] instead of [Intermediate 1-a] used in Synthesis Example 1- (2). (49 g, 75%)

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

[Intermediate 4-b] [Intermediate 4-c]

Intermediate 4-c] was obtained in the same manner as Intermediate 4-b except for using [Intermediate 4-b] instead of [Intermediate 1-b] used in Synthesis Example 1- (3). (34 g, 70%)

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

[Intermediate 4-c] [Intermediate 4-d]

Was synthesized in the same manner as Intermediate 4-d except for using [Intermediate 4-c] instead of [Intermediate 1-c] used in Synthesis Example 1- (4). (23 g, 59%).

Synthesis Example 4- (5): Synthesis of Intermediate 4-e

[Intermediate 4-d] [Intermediate 4-e]

Was synthesized in the same manner as Intermediate 4-e except for using [Intermediate 4-d] instead of [Intermediate 1-d] used in Synthesis Example 1- (5). (20 g, 91%).

Synthesis Example 4- (6): Synthesis of Intermediate 4-f

[Intermediate 4-e] [Intermediate 4-f]

Was synthesized in the same manner as Intermediate 4-f except for using [Intermediate 4-e] instead of [Intermediate 1-e] used in Synthesis Example 1- (6). (14 g, 79%).

Synthesis Example 4- (7): Synthesis of Compound 57

[Intermediate 4-f] [Compound 57]

Synthesis Example 1 (7) Use the intermediate 1-f] instead of [Intermediate 4-f] used in the bis (4-biphenyl) amine instead of N - [4- (1-naphthyl) phenyl] -4 -Biphenylamine, the compound [57] was obtained. (11 g, 66%).

Synthesis Example 5. Synthesis of Compound 58

Synthesis Example 5- (1): Synthesis of Intermediate 5-a

[Intermediate 4-c] [Intermediate 5-a]

Synthesis was carried out in the same manner except that [Intermediate 4-c] was used instead of [Intermediate 1-c] used in Synthesis Example 1- (4) and 2-bromobenzaldehyde was used instead of 2,5-dibromobenzaldehyde To obtain [intermediate 5-a]. (34 g, 62%).

Synthesis Example 5- (2): Synthesis of Intermediate 5-b

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

Was synthesized in the same manner as Intermediate 5-b except for using [Intermediate 5-a] instead of [Intermediate 1-d] used in Synthesis Example 1- (5). (28 g, 93%).

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

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

Intermediate 5-c] was obtained by the same method except for using [Intermediate 5-b] instead of [Intermediate 1-e] used in Synthesis Example 1- (6). (20 g, 83%).

Synthesis Example 5- (4): Synthesis of Intermediate 5-d

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

[Intermediate 5-c] (23 g, 53 mmol) and 200 m of tetrahydrofuran were put under a nitrogen condition and then cooled to -78 ° C. After 30 minutes, 1.6M n-butyl lithium (50 mL, 79 mmol) was slowly added dropwise, followed by stirring at room temperature for 2 hours. Trimethylborate (8.2 g, 79 mmol) was slowly added dropwise at -78 占 폚, and the mixture was stirred at room temperature for 2 hours. An aqueous hydrochloric acid solution was added to terminate the reaction, and the organic layer was extracted and concentrated under reduced pressure. Crystals were formed with hexane and the solid was filtered off and dried to give [intermediate 5-d] (18 g, 71%).

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

                                        [Intermediate 5-e]

Except that N-phenyl-2-dibenzofuranamine was used in place of the bis (4-biphenyl) amine used in Synthesis Example 1- (7) and 3-bromoiodobenzene was used in place of [Intermediate 1-f] Were synthesized in the same manner as in [Intermediate 5-e]. (12 g, 69%).

Synthesis Example 5- (6): Synthesis of Compound 58

[Intermediate 5-d] [Intermediate 5-e] [Compound 58]

The same procedure was followed except that [Intermediate 5-d] was used instead of [Intermediate 1-c] used in Synthesis Example 1- (4) and Intermediate 5-e was used instead of 2,5-dibromobenzaldehyde To obtain [Compound 58]. (9 g, 53%).

MS (MALDI-TOF): m / z 765.27 [M ^&lt; ⁺ &^gt;].

Synthesis Example 6. Synthesis of Compound 81

Synthesis Example 6- (1): Synthesis of Intermediate 6-a

[Intermediate 1-c] [Intermediate 6-a]

Was synthesized in the same manner as in Synthesis Example 1- (4), except that 2-bromobiphenyl was used instead of 2,5-dibromobenzaldehyde to obtain [Intermediate 6-a]. (44 g, 59%).

Synthesis Example 6- (2): Synthesis of Intermediate 6-b

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

[Intermediate 6-a] (40 g, 82.5 mmol), nitromethane 80 mL, and dichloromethane 400 mL were added under nitrogen and cooled to 0 占 폚. Iron trichloride (40.1 g, 247 mmol) was added thereto, followed by stirring at room temperature for 1 hour. The crystals were formed using methanol, followed by filtration and drying to obtain [Intermediate 6-b]. (31 g, 57%)

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

[Intermediate 6-b] [Intermediate 6-c]

Under nitrogen, [Intermediate 6-b] (30 g, 62.1 mmol) was added to 300 mL of tetrahydrofuran and then cooled to -78 ° C. N-Butyl lithium (47 mL, 74.6 mmol) was slowly added dropwise, followed by stirring at room temperature for 2 hours. After cooling to -78 ° C, iodine (24.6 g, 96.9 mmol) was slowly added dropwise, followed by stirring at room temperature for 8 hours. The mixture was extracted with an aqueous sodium thiosulfate solution and the organic layer was concentrated under reduced pressure. The crystals were formed with hexane, filtered and dried to obtain the compound of the formula (6-c). (38 g, 46%).

Synthesis Example 6- (4): Synthesis of Compound 81

[Intermediate 6-c] [Compound 81]

Except that [Intermediate 6-c] was used instead of [Intermediate 1-f] used in Synthesis Example 1- (7) and N-biphenyl 4-dibenzofuranamine was used in place of bis (4-biphenyl) Synthesis was conducted in the same manner to obtain [Compound 81]. (12 g, 63%).

MS (MALDI-TOF): m / z 815.28 [M ^&lt; ⁺ &^gt;].

Synthesis Example 7. Synthesis of Compound 101

Synthesis Example 7- (1): Synthesis of Intermediate 7-a

[Intermediate 1-f] [Intermediate 7-a]

Intermediate 7-a] was obtained in the same manner as Intermediate 1-b except for using [Intermediate 1-f] instead of [Intermediate 1-b] used in Synthesis Example 1- (3). (25 g, 64%).

Synthesis Example 7- (2): Synthesis of Compound 101

[Intermediate 7-a] [Compound 101]

[Intermediate 7-a] was used instead of [Intermediate 1-c] used in Synthesis Example 1- (4), and 2-chloro-4,6-diphenyl- 5-triazine was used to synthesize [Compound 101]. (11 g, 66%).

MS (MALDI-TOF): m / z 663.23 [M ^&lt; ⁺ &^gt;].

Synthesis Example 8. Synthesis of Compound 123

Synthesis Example 8- (1): Synthesis of Intermediate 8-a

[Intermediate 2-f] [Intermediate 8-a]

[Intermediate 8-a] was obtained in the same manner except that [Intermediate 2-f] was used instead of [Intermediate 1-b] used in Synthesis Example 1- (3). (17 g, 71%).

Synthesis Example 8- (2): Synthesis of Compound 123

[Intermediate 8-a] [Compound 123]

Except that [Intermediate 8-a] was used in place of [Intermediate 1-c] used in Synthesis Example 1- (4) and 2-chloro-4-naphthyl- 3,5-triazine was used to synthesize [Compound 123] (10 g, 62%).

MS (MALDI-TOF): m / z 713.25 [M ⁺ ] &^lt;

Synthesis Example 9. Synthesis of Compound 124

Synthesis Example 9- (1): Synthesis of Intermediate 9-a

[Intermediate 3-c] [Intermediate 9-a]

Intermediate 9-a] was obtained in the same manner as Intermediate 3-c except for using [Intermediate 3-c] instead of [Intermediate 1-b] used in Synthesis Example 1- (3). (15 g, 78%)

Synthesis Example 9- (2): Synthesis of Compound 124

[Intermediate 9-a] [Compound 124]

Was used instead of [Intermediate 9-a] instead of [Intermediate 7-a] used in Synthesis Example 7- (2) to obtain [Compound 124]. (15 g, 78%)

MS (MALDI-TOF): m / z 663.23 [M ^&lt; ⁺ &^gt;].

Synthesis Example 10. Synthesis of Compound 163

Synthesis Example 10- (1): Synthesis of Intermediate 10-a

[Intermediate 4-f] [Intermediate 10-a]

Was synthesized in the same manner as Intermediate 10-a except for using [Intermediate 4-f] instead of [Intermediate 1-b] used in Synthesis Example 1- (3). (12 g, 72%).

Synthesis Example 10- (2): Synthesis of Compound 163

[Intermediate 10-a] [Compound 163]

Except that [Intermediate 10-a] was used instead of [Intermediate 1-c] used in Synthesis Example 1- (4) and 2-chloro-4-phenylquinazoline was used instead of 2,5-dibromobenzaldehyde Synthesis was conducted in the same manner to give [Compound 163] (8 g, 65%).

MS (MALDI-TOF): m / z 636.22 [M ^&lt; ⁺ &^gt;

Synthesis Example 11. Synthesis of Compound 164

Synthesis Example 11- (1): Synthesis of Compound 164

[Intermediate 5-d] [Compound 164]

Except that 2- (3-bromo-phenyl) -4,6-diphenyl-1,3,5-triazine was used in place of [Intermediate 5-e] used in Synthesis Example 5- (6) To give [compound 164]. (9 g, 51%).

MS (MALDI-TOF): m / z 739.26 [M ^&lt; ⁺ &^gt;].

Synthesis Example 12. Synthesis of Compound 180

Synthesis Example 12- (1): Synthesis of Compound 180

[Intermediate 8-a] [Compound 180]

Chloro-3- (dibenzo [b, d] turan-4-yl) -pyridine instead of 2-chloro-4-naphthyl- ) -6-phenyl-1,3,5-triazine was used in place of the compound [180]. (11 g, 64%).

MS (MALDI-TOF): m / z 753.24 [M ^&lt; ⁺ &^gt;].

Examples 1 to 14: Preparation of blue organic electroluminescent device

In the following Examples 1 to 14, the organic compound represented by Chemical Formula (A) according to the present invention is used as a material for a hole-transporting layer in an organic light emitting device.

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, organic materials were deposited on the ITO in the order HATCN (50 Å) and NPD (600 Å) , A compound prepared by the present invention was formed into a thickness of 50 Å and doped with 5 wt% of a blue host (BH) + blue dopant (BD) to form a 200 Å thick light emitting layer. The films were deposited in the order of [ET]: Liq = 1: 1 (300 Å), Liq (10 Å), and Al (1,000 Å). The structures of [HATCN], [NPD], [BH], [BD], and [Liq] [ET] are as follows.

     <HATCN> <NPD>

        <BH> <BD>

         <Liq> <ET>

Comparative Example 1

Except that the hole assist layer used in Examples 1 to 14 was not used and NPD (650 ANGSTROM) was used.

The voltage, current, luminance, color coordinate and lifetime of the organic EL device manufactured according to Examples 1 to 14 and Comparative Example 1 were measured and the results are shown in Table 1 below. Here, T95 represents the time required for the luminance to be reduced to 95% of the initial luminance (2000 cd / m 2).

division Hole assist layer V Cd / A CIEx CIEy T95 (Hrs) Comparative Example 1 - 4.3 6.8 0.132 0.128 15 Example 1 Compound 1 4.2 8.1 0.133 0.129 23 Example 2 Compound 4 4.3 8.3 0.133 0.128 25 Example 3 Compound 9 4.2 8.0 0.132 0.127 22 Example 4 Compound 17 4.1 8.1 0.134 0.128 24 Example 5 Compound 18 4.2 8.1 0.134 0.130 23 Example 6 Compound 21 4.2 8.1 0.133 0.129 24 Example 7 Compound 28 4.1 8.2 0.132 0.127 25 Example 8 Compound 36 4.1 8.2 0.132 0.128 25 Example 9 Compound 57 4.2 8.1 0.133 0.128 24 Example 10 Compound 58 4.1 8.2 0.132 0.127 23 Example 11  Compound 64 4.3 8.0 0.134 0129 27 Example 12  Compound 81 4.2 8.1 0.133 0128 26 Example 13  Compound 85 4.3 8.1 0.133 0.129 25 Example 14  Compound 88 4.2 8.3 0.133 0.126 24

As shown in Table 1, when the organic compound obtained according to the present invention is used as a hole-assisted layer, it has higher efficiency and longer life than Comparative Example 1. Thus, the production of an organic light emitting device It is possible to utilize it.

Examples 15 to 27: Manufacture of organic electroluminescent device

 Examples 15 to 27 are examples in which the organic compound represented by the formula (A) according to the present invention is used as a material for an electron transport layer in an organic light emitting device, and a method of manufacturing the organic light emitting device is as follows.

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 and then an organic material was deposited on the ITO using HATCN (50 Å), NPD (650 Å), Blue host (BH) + Blue dopant BD) to form a light emitting layer having a thickness of 200 ANGSTROM. The compound prepared by the present invention: Liq = 1: 1 (300 Å), Liq (10 Å) and Al (1,000 Å) were deposited in this order and measured at 0.4 mA. The structures of [HATCN], [NPD], [BD], [BH], and [Liq] are as follows.

[HATCN] [NPB] [BD]

    [BH] [Liq]

Comparative Example 2

The organic electroluminescent 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 above embodiment. .

     [ET]

The voltage, current, luminance, color coordinate, and lifetime of the organic EL device manufactured according to Examples 15 to 27 and Comparative Example 2 were measured, and the results are shown in Table 2 below. Here, T95 represents the time required for the luminance to be reduced to 95% of the initial luminance (2000 cd / m ² ).

division ETL V Cd / A CIEx CIEy T ₉₅ (Hrs) Comparative Example 2 ET 4.2 6.7 0.133 0.129 16 Example 15 Compound 101 3.7 7.6 0.132 0.129 32 Example 16 Compound 105 3.8 7.5 0.132 0.129 37 Example 17 Compound 109 3.5 7.8 0.132 0.128 35 Example 18 Compound 123 3.4 7.9 0.133 0.127 29 Example 19 Compound 124 3.6 7.6 0.133 0.126 32 Example 20 Compound 142 3.9 7.6 0.133 0.127 35 Example 21 Compound 145 3.8 8.0 0.132 0.126 38 Example 22 Compound 163 4.0 8.1 0.133 0.129 35 Example 23 Compound 164 3.7 7.7 0.132 0.130 32 Example 24 Compound 180 3.7 7.7 0.133 0.128 37 Example 25 Compound 201 3.6 7.8 0.132 0.129 33 Example 26 Compound 226 3.8 7.5 0.133 0.126 38 Example 27 Compound 232 3.9 7.9 0.134 0.130 35

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.

Claims (17)

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

In the above formula (A)
Wherein Q1 and Q2 are the same or different and 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,
Each of Ar 1 to Ar 4 is the same or different and is 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-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 arylthio group, a substituted or unsubstituted C1-C30 alkylamine 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 A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having 0, 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 aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, , Or any one of substituents selected from the following formulas [A] to [Q], wherein one of Ar1 to Ar4 is any one selected from the following Structural Formulas A to Q Lt; / RTI &gt;
In the aromatic hydrocarbon ring or aromatic heterocycle of Q1 and Q2 and the two benzene rings located in the lower part of the formula A, the carbon atoms of the aromatic ring not bonded to Ar1 to Ar4 are each bonded to hydrogen or deuterium,
[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]

In the above Structural Formulas A to Q,
The linking groups L1 to L3 are the same or different and independently of each other, a single bond, 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 A substituted or unsubstituted alkylene group having 2 to 60 carbon atoms, an alkynylene 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 Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms,
Each of p1 to p3 is an integer of 1 to 3, and when each of them is 2 or more, each of the linking groups L1 to L3 is the same or different from each other,
Each of R 1 to R 9 is the same or different and is 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-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 arylthio group, a substituted or unsubstituted C1-C30 alkylamine 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 A substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having 0, N or S, 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 aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, , &Lt; / RTI &gt;
And the carbon atom of the formed alicyclic or aromatic monocyclic or polycyclic ring may be any one or more selected from N, S, and O, and the carbon atom of the alicyclic or aromatic monocyclic or polycyclic ring may form a monocyclic or polycyclic ring of alicyclic or aromatic, Which may be substituted by a heteroatom,
The substituent Ra in the formula [Q] is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom,
Represents a single bond which is bonded to the carbon atoms of two benzene rings located at the bottom of Q1, Q2 or the formula (A)
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 1 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,
Q1 and Q2 in the above formula (A) are the same or different and independently of each other, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms. 3. The method of claim 2,
Wherein at least one of Q1 and Q2 is any aromatic hydrocarbon ring selected from phenanthrene, triphenylene and pyrene. 3. The method of claim 2,
Wherein one of Q1 and Q2 is any one aromatic hydrocarbon ring selected from phenanthrene, triphenylene and pyrene, and the other is a benzene ring or a naphthalene ring. 5. The method of claim 4,
Wherein one of Q1 and Q2 is any one aromatic hydrocarbon ring selected from phenanthrene, triphenylene and pyrene, and the other is a benzene ring. The method of claim 1, wherein
Each of the linking groups L1 to L3 is the same or different and independently of one another is a single bond or any one selected from the following Structural Formulas 22 to 30,
p, q and r are 1 or 2, respectively.
[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]

In the structural formulas 22 to 30, the carbon of the aromatic ring may be bonded to hydrogen or deuterium. The method according to claim 1,
Wherein each of Ar1 to Ar4 is the same or different and is independently hydrogen, deuterium, or any substituent selected from among the above Structural A to Structural Formula Q, To Q &lt; / RTI &gt; The method according to claim 1,
Wherein one of Ar1 to Ar4 is [Structural Formula A]. The method according to claim 1,
Wherein one of Ar 1 to Ar 4 is any one of [structural formulas B] to [structural formula H]. The method according to claim 1,
Wherein one of Ar1 to Ar4 is any one of [structural formulas I] to [structural formula P]. The method according to claim 1,
Wherein the compound represented by the formula (A) is any one selected from the group consisting of the following compounds [1] to [232].
<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>

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

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

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

<Compound 205><Compound206><Compound207><Compound208>

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

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

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

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

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

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

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 11. 13. The method of claim 12,
Wherein the organic light emitting device includes at least one of a hole injecting layer, a hole transporting 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, device. 14. The method of claim 13,
Wherein the organic compound is used as a hole-assist layer. 14. The method of claim 13,
Wherein the organic compound is used for an electron transport layer. 14. The method of claim 13,
Wherein at least one layer selected from the respective layers is formed by a deposition process or a solution process. 13. The method of claim 12,
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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