KR102507585B1 - Novel organic compounds derivatives and organic light-emitting diode therewith - Google Patents

Abstract

The present invention relates to an organic compound represented by the following [Formula A] and an organic light emitting device including the same, wherein in [Formula A], Q1, Q2, Ar1 to Ar4 are the same as described in the detailed description of the invention.
[Formula A]

Description

Novel organic compounds and organic light-emitting devices containing them {Novel organic compounds derivatives and organic light-emitting diode therewith}

The present invention relates to a novel organic compound and an organic light emitting device including the same, and more particularly, to a novel organic compound capable of realizing device characteristics such as high efficiency, long lifespan, and low voltage driving when used as an organic light emitting device, and the same It relates to an organic light emitting device comprising

An organic light emitting diode (OLED) is a display using a self-luminous phenomenon, and has advantages such as a large viewing angle, lightness and compactness compared to liquid crystal displays, and fast response speed. ) Applications to displays or lighting are expected.

In general, an organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material, and an organic light emitting device using the organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.

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

Materials used as the organic layer in the organic light emitting device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc. layer or hole blocking layer or the like may be added.

Among these, as a prior art related to the material for the electron transport layer, in Laid-Open Patent Publication No. 10-2012-010420 (2012.09.20), it has excellent electron transport ability and hole blocking ability, excellent luminous efficiency, and stability in a thin film state In order to prepare this highly organic compound, an organic compound in which a pyridoindole derivative is bonded to a substituted anthracene ring structure is described, and in Japanese Unexamined Patent Publication No. 2010-168363 (August 5, 2010), external quantum efficiency and drive An anthracene derivative having a pyridine naphthyl group having excellent voltage characteristics is described.

In addition, as a prior art document showing more improved characteristics by putting a hole auxiliary layer between the light emitting layer and the electron transport layer, in Publication No. 10-2016-0012066 (February 2, 2016), an amine-based compound is used as an auxiliary layer in the hole transport region. The technology used is described.

However, although various types of methods for manufacturing an organic light emitting device having more efficient light emitting characteristics have been tried in the prior art including the above prior art, low voltage driving is still possible, organic light emitting efficiency and long lifespan are still possible. The need for development of a material that can be used as an electron transport layer or a hole auxiliary layer for a light emitting device and an organic light emitting device including the same has been continuously demanded.

Publication No. 10-2012-0104204 (2012.09.20) Japanese Unexamined Patent Publication No. 2010-168363 (2010.08.05) Publication No. 10-2016-0012066 (2016.02.02)

Therefore, the first technical problem to be achieved by the present invention is to provide a novel organic compound having a specific structure that can have high efficiency, low voltage and long lifespan characteristics by using it in an electron transport layer or a hole auxiliary layer in an organic light emitting device.

In addition, a second technical problem according to the present invention is to provide a novel organic light emitting device including the organic compound in a hole auxiliary layer or an electron transport layer.

In order to achieve the above technical problems, the present invention provides an organic compound represented by the following [Formula A].

[Formula A]

In the above [Formula A],

Q1 and Q2 are each 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,

Ar1 to Ar4 are the same or different, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted carbon atom 2 to 30 alkynyl groups, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl groups having 5 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylamine having 1 to 30 carbon atoms substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms, substituted or unsubstituted heteroatom O , a heteroaryl group having 2 to 50 carbon atoms having 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 germanium group, Any one selected from 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 amide group, an ether group, and an ester group, Or any one substituent selected from the following [Formula A] to [Formula Q], wherein one of Ar1 to Ar4 is any one substituent selected from the following [Formula A] to [Formula Q],

In the aromatic hydrocarbon rings or aromatic heterocycles of Q1 and Q2 and the lower two benzene rings in Formula A, the carbon atoms of the aromatic rings not bonded to Ar1 to Ar4 are bonded to hydrogen or deuterium, respectively,

[Formula A] [Formula B] [Formula C]

[Formula D] [Formula E] [Formula F]

[Formula G] [Formula H] [Formula I]

[Formula J] [Formula K] [Formula L]

[Formula M] [Formula N] [Formula O]

[Formula P] [Formula Q]

In the [Structural Formula A] to [Structural Formula Q],

The linking groups L1 to L3 are each 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, or a substituted or unsubstituted group. Alkynylene group having 2 to 60 carbon atoms, substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, substituted or unsubstituted arylene group having 6 to 60 carbon atoms Or, any one selected from a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms,

The p1 to p3 are each an integer of 1 to 3, but when each of these is 2 or more, each linking group L1 to L3 is the same as or different from each other,

R1 to R9 are the same or different, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted carbon atom 2 to 30 alkynyl groups, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl groups having 5 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylamine having 1 to 30 carbon atoms substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms, substituted or unsubstituted heteroatom O , a heteroaryl group having 2 to 50 carbon atoms having 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 germanium group, Any one selected from 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 amide group, an ether group, and an ester group,

They may be linked to each other adjacent substituents to form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring may be any one or more selected from N, S, and O. May be substituted with a heteroatom,

The substituent Ra in [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 heteroatom,

The '-*' means a single bond bonded to Q1, Q2 or carbon atoms of two lower benzene rings in Formula A.

In addition, the present invention in order to achieve the second object, the 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 at least one organic compound represented by Formula A according to the present invention. .

According to the present invention, the organic light emitting device including the compound represented by [Formula A] in the electron transport layer or hole auxiliary layer may have high efficiency, low voltage, and long lifespan compared to conventional organic light emitting devices.

1 is a schematic diagram of an organic light emitting device according to one 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].

[Formula A]

In the above [Formula A],

Q1 and Q2 are each 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,

They are the same or different, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or 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, or a substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms An aryloxy group, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, substituted or unsubstituted 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 heteroatom having O, N or S A heteroaryl group having 2 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 germanium group, a substituted or unsubstituted Any one selected from a 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 amide group, an ether group, and an ester group, or ] to any one substituent selected from [structural formula Q], wherein one of Ar1 to Ar4 is any one substituent selected from the following [structural formula A] to [structural formula Q],

In the aromatic hydrocarbon rings or aromatic heterocycles of Q1 and Q2 and the lower two benzene rings in Formula A, the carbon atoms of the aromatic rings not bonded to Ar1 to Ar4 are bonded to hydrogen or deuterium, respectively,

[Formula A] [Formula B] [Formula C]

[Formula D] [Formula E] [Formula F]

[Formula G] [Formula H] [Formula I]

[Formula J] [Formula K] [Formula L]

[Formula M] [Formula N] [Formula O]

[Formula P] [Formula Q]

In the [Structural Formula A] to [Structural Formula Q],

The linking groups L1 to L3 are each 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, or a substituted or unsubstituted group. Alkynylene group having 2 to 60 carbon atoms, substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, substituted or unsubstituted arylene group having 6 to 60 carbon atoms Or, any one selected from a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms,

The p1 to p3 are each an integer of 1 to 3, but when each of these is 2 or more, each linking group L1 to L3 is the same as or different from each other,

R1 to R9 are the same or different, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted carbon atom 2 to 30 alkynyl groups, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl groups having 5 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylamine having 1 to 30 carbon atoms substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms, substituted or unsubstituted heteroatom O , a heteroaryl group having 2 to 50 carbon atoms having 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 germanium group, Any one selected from 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 amide group, an ether group, and an ester group,

They may be linked to each other adjacent substituents to form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring may be any one or more selected from N, S, and O. May be substituted with a heteroatom,

The substituent Ra in [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 heteroatom,

The '-*' refers to a single bond bonded to Q1, Q2 or carbon atoms of two benzene rings located at the bottom in Formula A,

Here, 'substitution' in the above 'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxyl group, nitro group, C 1 to 24 alkyl group, C 1 to 24 halogenated alkyl group, C 2 to 24 carbon atoms Alkenyl group, C2-24 alkynyl group, C1-24 heteroalkyl group, C6-24 aryl group, C7-24 arylalkyl group, C2-24 heteroaryl group, or C2-24 hetero Arylalkyl group, C1-24 alkoxy group, C1-24 alkylamino group, C1-24 arylamino group, C1-24 heteroarylamino group, C1-24 alkylsilyl group, C6-24 It means that it is substituted with one or more substituents selected from the group consisting of an arylsilyl group and an aryloxy group having 6 to 24 carbon atoms.

On the other hand, considering the range of the alkyl group or aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms" and the "substituted or unsubstituted aryl group having 6 to 50 carbon atoms" in the present invention, the The range of carbon atoms of an alkyl group having 1 to 30 carbon atoms and an aryl group having 6 to 50 carbon atoms refers to the total number of carbon atoms constituting the alkyl part or the aryl part when the substituent is regarded as unsubstituted without considering the substituted part. will be. For example, a phenyl group in which a butyl group is substituted at the para-position should be regarded as corresponding to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

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 removing one hydrogen, and includes a single or fused ring system containing 5 to 7 members, preferably 5 or 6 members, In addition, when there is a substituent in the aryl group, a ring may be additionally formed by being fused with an adjacent substituent.

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, phenanthryl group, and aromatic groups such as pyrenyl group, indenyl group, fluorenyl group, tetrahydronaphthyl group, perylenyl group, chrysenyl group, naphthasenyl group, fluoranthenyl group, and the like, and at least one hydrogen atom in the aryl group is a deuterium atom, a halogen atom atom, hydroxyl group, nitro group, cyano group, silyl group, amino group (-NH ₂ , -NH(R), -N(R')(R″), R' and R" independently of each other have 1 to 10 carbon atoms In this case, it is referred to as "alkylamino group"), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, 2 to 2 carbon atoms Alkenyl group having 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms or carbon atoms 2 to 24 It may be substituted with a heteroarylalkyl group of

The heteroaryl group, which is a substituent used in the compound of the present invention, contains 1, 2, or 3 hetero atoms selected from N, O, P, Si, S, Ge, Se, and Te, and has 2 to 24 carbon atoms in which the remaining ring atoms are carbon atoms. It refers to a ring aromatic system of , and the rings may be fused to form a ring. In addition, one or more hydrogen atoms of the heteroaryl group may be substituted with the same substituent as that of the aryl group.

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

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

Specific examples of the alkoxy group used in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, and the like, One or more hydrogen atoms in the alkoxy group may be substituted with substituents similar to those of the aryl group.

Specific examples of the substituent silyl group used in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl , dimethylfurylsilyl, and the like, and one or more hydrogen atoms in the silyl group may be substituted with the same substituents as in the case of the aryl group.

In the organic compound represented by [Formula A] according to the present invention, two rings (Q1 and Q2 rings connected to Ar1 or Ar2) positioned at the upper part in Formula A are the same or different, and independently substituted with each other. 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 and Each of the benzene rings connected) has a feature that only one is bonded to any one substituent selected from the following [Structural Formula A] to [Structural Formula Q], and this organic compound is used as a hole auxiliary layer or electron transport layer material in an organic light emitting device. When used, it can have high efficiency, low voltage and long life characteristics.

As an embodiment, Q1 and Q2 are each the same or different, and may be independently substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 carbon atoms. In this case, at least one of Q1 and Q2 is phenanthrene. , triphenylene, may be any one selected from pyrene.

In addition, when Q1 and Q2 are substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 carbon atoms, one of Q1 and Q2 is an aromatic hydrocarbon ring selected from phenanthrene, triphenylene, and pyrene, 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 one may be a benzene ring. there is.

In addition, as preferred examples of the linking groups L1 to L3 in the compound represented by Formula A according to the present invention, the linking groups L1 to L3 are the same or different, and independently of each other, a single bond, or the following [Formula 22] to [Formula 30] It is any one selected from, and in this case, the p, q and r may be 1 or 2, respectively.

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

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

[Structural Formula 30]

In Structural Formulas 22 to 30, hydrogen or deuterium may be bonded to the carbon site of the aromatic ring.

In addition, as preferred examples of Ar1 to Ar4 in the compound represented by Formula A according to the present invention, the Ar1 to Ar4 are the same or different, and independently hydrogen, deuterium, or among the [Formula A] to [Formula Q]. Any one substituent selected, but one of Ar1 to Ar4 may be any one substituent selected from the following [Formula A] to [Formula Q].

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

In addition, one of Ar1 to Ar4 may be any one of [Formula B] to [Formula H]. In addition, one of Ar1 to Ar4 may be any one of [Structural Formula I] to [Structural Formula P].

In addition, as a preferred example of structural formula Q in the organic compound represented by formula A according to the present invention, Ra is substituted or unsubstituted dibenzofuran, substituted or unsubstituted carbazole, or substituted or unsubstituted dibenzothiophene. , It may be a substituted or unsubstituted fluorene, in which case the benzene ring carbon atom in the dibenzofuran, carbazole, dibenzothiophene and fluorene or the nitrogen atom of carbazole or the 9th position carbon atom of fluorene is It may be bonded to L3 in the structural formula Q above.

On the other hand, as a specific example of the organic compound represented by [Formula A] according to the present invention, it may be a compound represented by any one selected from the group represented by [Compound 1] to [Compound 232], but is not limited thereto.

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

<Compound 5> <Compound 6> <Compound 7> <Compound 8>

<Compound 9> <Compound 10> <Compound 11> <Compound 12>

<Compound 13> <Compound 14> <Compound 15> <Compound 16>

<Compound 17> <Compound 18> <Compound 19> <Compound 20>

<Compound 21> <Compound 22> <Compound 23> <Compound 24>

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

<Compound 29> <Compound 30> <Compound 31> <Compound 32>

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

<Compound 37> <Compound 38> <Compound 39> <Compound 40>

<Compound 41> <Compound 42> <Compound 43> <Compound 44>

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

<Compound 49> <Compound 50> <Compound 51> <Compound 52>

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

<Compound 57> <Compound 58> <Compound 59> <Compound 60>

<Compound 61> <Compound 62> <Compound 63> <Compound 64>

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

<Compound 69> <Compound 70> <Compound 71> <Compound 72>

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

<Compound 77> <Compound 78> <Compound 79> <Compound 80>

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

<Compound 85> <Compound 86> <Compound 87> <Compound 88>

<Compound 89> <Compound 90> <Compound 91> <Compound 92>

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

<Compound 97> <Compound 98> <Compound 99> <Compound 100>

<Compound 101> <Compound 102> <Compound 103> <Compound 104>

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

<Compound 109> <Compound 110> <Compound 111> <Compound 112>

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

<Compound 117> <Compound 118> <Compound 119> <Compound 120>

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

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

<Compound 129> <Compound 130> <Compound 131> <Compound 132>

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

<Compound 137> <Compound 138> <Compound 139> <Compound 140>

<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>

<Compound 221> <Compound 222> <Compound 223> <Compound 224>

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

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

In addition, the present invention is 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 the organic compound represented by Chemical Formula A according to the present invention described above. provide a small

In this case, in the present invention, "(the organic layer) contains one or more kinds of organic compounds" means "(the organic layer) includes one organic compound belonging to the scope of the present invention or two or more different kinds belonging to the category of the organic compound. It may contain a compound".

At this time, the organic layer containing the organic compound of the present invention is at least one of a hole injection layer, a hole transport layer, a hole auxiliary 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. Preferably, the organic compound of the present invention may be used for a hole auxiliary layer or for an electron transport layer.

The organic light emitting diode according to the present invention may have high efficiency, low voltage drive and long lifespan when the organic compound represented by [Formula A] is used for a hole auxiliary layer or an electron transport layer.

The material of 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, for example, N,N'-bis(3-methylphenyl)-N,N '-diphenyl-[1,1-biphenyl]-4,4'-diamine (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 Hole Injecting Layer (HIL) may be additionally stacked on the lower part of the hole transport layer. As the hole injection layer, CuPc (copperphthalocyanine) or starburst amine type TCTA (which is commonly used in the art) 4,4',4"-tri(N-carbazolyl)triphenyl-amine), m-MTDATA(4,4',4"-tris-(3-methylphenylphenylamino)triphenylamine) and the like may be used.

In addition, the light emitting layer in the organic light emitting device of the present invention may be made of a host and a dopant, and in this case, the host used for the light emitting layer may include one or more compounds represented by Formula H below, but is not limited thereto. .

[Formula H]

In the above [formula H],

X ₁ to X ₁₀ are the same or different, and independently of each other, 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 Ringed cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, 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 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, or a substituted or unsubstituted 5 carbon atoms to 30 arylamine groups, substituted or unsubstituted aryl groups having 5 to 50 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 50 carbon atoms having O, N or S as heteroatoms, and substituted or unsubstituted silicon groups. , 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, any one selected from the group consisting of an amide group and an ester group, Groups adjacent to each other may form an aliphatic, aromatic, aliphatic hetero or aromatic hetero condensed ring.

More specifically, the host may be represented by any one selected from the group represented by [Compound 301] to [Compound 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 [Formula 2], and various other known dopant materials may be used.

[Formula 1] [Formula 2]

Among the [Formula 1] and [Formula 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, or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms , It may be any one selected from a heteroarylene group having 3 to 50 carbon atoms, substituted or unsubstituted, and having O, N or S as a heteroatom.

More specifically, A is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms or a single bond, and is preferably anthracene, pyrene, phenanthrene, indenophenanthrene, chrysene, naphthacene, picene, or triphenyl. It may be any one of ene, perylene, and pentacene, and more specifically, A may be a substituent represented by any one of the following formulas A1 to A10.

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

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

[Formula A7] [Formula A8] [Formula A9]

[Formula A10]

Here, Z ₁ to Z ₂ in [Formula A3] are 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, or a substituted or unsubstituted carbon atom 2 to 60 alkynyl groups, substituted or unsubstituted alkoxy groups having 1 to 60 carbon atoms, substituted or unsubstituted alkylthio groups having 1 to 60 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 60 carbon atoms, substituted Or an unsubstituted 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, or a substituted or unsubstituted aryl group having 2 to 60 carbon atoms. Heteroaryl group, substituted or unsubstituted C1-60 (alkyl) amino group, di(substituted or unsubstituted C1-60 alkyl) amino group, or (substituted or unsubstituted C6-60 aryl) amino group , Di (substituted or unsubstituted aryl having 6 to 60 carbon atoms) at least one selected from the group consisting of amino groups, Z ₁ to Z ₂ Each of which is the same as or different from each other, may form a condensed ring with a group adjacent to each other. .

In addition, in [Formula 1],

Wherein 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;

Wherein 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, or a substituted Or an unsubstituted heteroalkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 24 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 24 carbon atoms, a cyano group, a halogen group, a substituted or unsubstituted carbon number 1 from the group consisting of an aryloxy group having 6 to 24, 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, deuterium and hydrogen More than species are selected, Y ₁ to Y ₂ are each the same as or different from each other, and may form an aliphatic, aromatic, aliphatic hetero or aromatic hetero condensed ring with a group adjacent to each other.

Wherein l, m is an integer of 1 to 20, respectively, n is an integer of 1 to 4.

In addition, in [Formula 2],

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

Also above B is a single bond or -[C(R ₅ )(R ₆ )] _p -, wherein p is an integer from 1 to 3, but when p is 2 or more, two or more R ₅ and R ₆ are the same as or different from each other;

Wherein R ₁ , R ₂ , R _{3 ,} R ₅ and R ₆ are each independently selected from hydrogen, heavy hydrogen, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group, A salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, or a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms. , substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, substituted or unsubstituted carbon atoms Aryl group having 6 to 60 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, substituted Or an unsubstituted (alkyl) amino group having 1 to 60 carbon atoms, a di (substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, or a (substituted or unsubstituted aryl having 6 to 60 carbon atoms) amino group, a di (substituted or It may be selected from an unsubstituted aryl) amino group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron. ,

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

In addition, the amine group bonded to A in [Formula 1] and [Formula 2] may be represented by any one selected from the group represented by the following [substituent 1] to [substituent 52], but is not limited thereto.

[substituent 1] [substituent 2] [substituent 3]

[substituent 4] [substituent 5] [substituent 6]

[substituent 7] [substituent 8] [substituent 9]

[substituent 10] [substituent 11] [substituent 12]

[substituent 13] [substituent 14] [substituent 15]

[substituent 16] [substituent 17] [substituent 18]

[substituent 19] [substituent 20] [substituent 21]

[substituent 22] [substituent 23] [substituent 24]

[substituent 25] [substituent 26] [substituent 27]

[substituent 28] [substituent 29] [substituent 30]

[substituent 31] [substituent 32] [substituent 33]

[substituent 34] [substituent 35] [substituent 36]

[substituent 37] [substituent 38] [substituent 39]

[substituent 40] [substituent 41] [substituent 42]

[substituent 43] [substituent 44] [substituent 45]

[substituent 46] [substituent 47] [substituent 48]

[substituent 49] [substituent 50] [substituent 51]

[substituent 52]

In the above substituents, R is the same or independently of each other, hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or its salt, sulfonic acid group or its salt, phosphoric acid or salts thereof, substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 60 carbon atoms, substituted or unsubstituted alkynyl groups having 2 to 60 carbon atoms, substituted or unsubstituted carbon atoms 1 to 60 An alkoxy group having 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 aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted Unsubstituted aryloxy group having 5 to 60 carbon atoms, substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, substituted or unsubstituted aryl group having 1 to 60 carbon atoms (Alkyl)amino group, di(substituted or unsubstituted alkyl having 1 to 60 carbon atoms)amino group, or (substituted or unsubstituted aryl having 6 to 60 carbon atoms)amino group, di(substituted or unsubstituted aryl having 6 to 60 carbon atoms) ) It may be selected from an amino group, 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, each of which may be substituted by 1 to 12 atoms. and each substituent may form a condensed ring with a group adjacent to each other.

In addition, the light emitting layer may further include various hosts and various dopant materials in addition to the dopant and the host.

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

Meanwhile, for the electron transport layer used in the present invention, the organic compound according to the present invention may be used alone or in combination with a known compound.

When the electron transport layer is used as a mixture with the organic compound of the present invention, any material for the electron transport layer that can be mixed can be used as long as it functions to stably transport electrons injected from the electron injection electrode (cathode). As such, a known electron transport material may be used.

Examples of such known electron transport materials include quinoline derivatives, particularly tris(8-quinolinolate) aluminum (Alq3), TAZ, BAlq, beryllium bis(benzoquinolin-10-noate) (beryllium bis(benzoquinolin-10 -olate: Bebq2), compound 501, compound 502, BCP, oxadiazole derivatives such as PBD, BMD, BND, etc. may be used, but are not limited thereto.

TAZ BAlq

<Compound 501> <Compound 502> BCP

In addition, the electron transport layer used in the present invention may use the organometallic compound represented by Formula F alone or in combination with the electron transport layer material.

[Formula F]

In the above [Formula F],

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

O is oxygen,

A is 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, or a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms An alkynyl group, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, and a substituted or unsubstituted heteroatom having 2 to 50 carbon atoms having O, N or S Any one selected from aryl groups,

When M is one metal selected from alkali metals, m = 1 and n = 0,

When M is one metal selected from alkaline earth metals, m = 1, n = 1, or m = 2, n = 0,

When M is boron or aluminum, m is any one of 1 to 3, and n is any one of 0 to 2, satisfying m + n = 3.

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

[Formula C1] [Formula C2] [Formula C3]

[Formula C4] [Formula C5] [Formula C6]

[Formula C7] [Formula C8] [Formula C9] [Formula C10]

[Formula C11] [Formula C12] [Formula C13]

[Formula C14] [Formula C15] [Formula C16]

[Formula C17] [Formula C18] [Formula C19] [Formula C20]

[Formula C21] [Formula C22] [Formula C23]

[Formula C24] [Formula C25] [Formula C26]

[structural formula C27] [structural formula C28] [structural formula C29] [structural formula C30]

[Formula C31] [Formula C32] [Formula C33]

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

[Formula C37] [Formula C38] [Formula C39]

In the above [structural formula C1] to [structural formula C39],

R are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, 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 30 carbon atoms, a substituted or unsubstituted Heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted Unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and substituted or unsubstituted arylsilyl having 6 to 30 carbon atoms It is selected from groups, and may be linked with adjacent substituents through alkylene or alkenylene to form a spiro ring or a fused ring. However, here, 'substitution' in the above 'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group, alkoxy group, alkylamino group, arylamino group, heteroarylamino group, alkylsilyl group, aryl It means that it is substituted with one or more substituents selected from the group consisting of a silyl group, an aryloxy group, an aryl group, a heteroaryl group, germanium, phosphorus, and boron.

On the other hand, an electron injection layer (EIL) may be further laminated on top of the electron transport layer to facilitate electron injection from the cathode and ultimately improve power efficiency. Anything commonly used in the art may be used without particular limitation, and the electron injection layer forming material may be any known electron injection layer forming material such as CsF, NaF, LiF, NaCl, Li ₂ O, BaO, and the like. material can be used. Deposition conditions for the electron injection layer vary depending on the compound used, but may generally be selected from a range of conditions almost identical to those for forming the hole injection layer.

The electron injection layer may have a thickness of about 1 Å to about 100 Å or about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the aforementioned range, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.

In addition, in the present invention, a negative electrode is present on the electron injection layer, and the negative electrode is lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium- A metal such as indium (Mg-In) or magnesium-silver (Mg-Ag) may be used for forming the cathode, or a transmissive cathode using ITO or IZO may be used to obtain a top light emitting device.

In addition, in the present invention, one or more layers selected from the hole injection layer, the hole transport layer, the functional layer having both 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. can

Here, the deposition method refers to a method of forming a thin film by evaporating a material used as a material for forming each layer through heating in a vacuum or low pressure state, and the solution process is to form each layer. It refers to a method of forming a thin film by mixing a material used as a material for a solvent with a solvent and mixing the same with a method such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating, and the like.

In addition, the organic light emitting device in the present invention is a flat panel display device; flexible display devices; devices for monochromatic or white flat lighting; And, it can be used for any one device selected from; a single color or white flexible lighting device.

Hereinafter, the organic light emitting device of the present invention will be described with reference to FIG. 1 .

1 is a cross-sectional view showing the 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 auxiliary layer 45, an organic light emitting layer 50, an electron transport layer 60 and a cathode 80, and holes are provided as needed. It may further include an injection layer 30 and an electron injection layer 70, and in addition to that, it is possible to further form one or two intermediate layers, and a hole blocking layer or an electron blocking layer may be further formed.

Referring to FIG. 1 , an organic light emitting device and a manufacturing method thereof according to the present invention are as follows. First, the anode 20 is formed by coating a material for an anode electrode on the substrate 10 . Here, as the substrate 10, a substrate used in a typical organic EL device is used, and an organic substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and water resistance is preferable. In addition, as materials for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, are used.

The hole injection layer 30 is formed by vacuum thermal deposition or spin coating of a hole injection layer material on the anode 20 electrode. Next, the hole transport layer 40 is formed by vacuum thermal evaporation or spin coating of a hole transport layer material on the hole injection layer 30 .

Subsequently, a hole auxiliary layer 45 is formed on the hole transport layer 40, and then, an organic light emitting layer 50 is laminated on top of the hole auxiliary layer 45 and selectively formed on top of the organic light emitting layer 50. As a result, the hole blocking layer (not shown) may be formed as a thin film using a vacuum deposition method or a spin coating method. The hole-blocking layer serves to prevent this problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level because the lifespan and efficiency of the device are reduced when holes pass through the organic light emitting layer and flow into the cathode. . At this time, the hole-blocking material used is not particularly limited, but should have electron transport ability and higher ionization potential than the light emitting compound, and typically BAlq, BCP, TPBI, and the like may be used.

After depositing the electron transport layer 60 on the hole blocking layer through a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a metal for forming a cathode is vacuum-heated on top of the electron injection layer 70. The organic EL device is completed by depositing and forming the cathode 80 electrode. Here, the metal for forming the cathode is lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag) may be used, and a transmissive cathode using ITO or IZO may be used to obtain a top light emitting device.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for explaining the present invention in more detail, and it will be apparent to those skilled in the art that the scope of the present invention is not limited thereto.

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) were mixed with 1-methyl-2-pyrrolidinone 500 under nitrogen conditions. ml and stirred at 150 °C for 12 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure and separated by column to obtain [Intermediate 1-a]. (71.5g, 65%)

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

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

Under nitrogen conditions [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 (52.9g, 352 mmol) was added to 500 ml of toluene and stirred at 110°C for 24 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure and separated by column to obtain [Intermediate 1-b]. (50.5 g, 78%)

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

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

Under nitrogen conditions [intermediate 1-b] (50 g, 136 mmol), bis (pinacolato) diborane (51.9 g, 204 mmol), (diphenylphosphinoferrocene) palladium dichloride (5 g, 6.8 mmol), potassium acetate ( 40.1 g, 408 mmol) was 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 separated by column to obtain [Intermediate 1-c]. (46.8g, 75%)

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

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

[Intermediate 1-c] (45 g, 98 mmol), 2,5-dibromobenzaldehyde (25.9 g, 98 mmol), tetrakis (triphenylphosphine) palladium (2.3 g, 2 mmol), potassium carbonate (40.7 g, 294 mmol), 500 mL of toluene, and 150 mL of distilled water were added, 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 separated by column to obtain [Intermediate 1-d]. (31.8g, 63%)

.

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

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

Potassium tertiary butoxide (9.8g, 87mmol) and 100ml of tetrahydrofuran were stirred under nitrogen, and then cooled to 0°C. After dissolving (methoxymethyl)triphenylphosphonium chloride (29.9g, 87mmol) in 150ml of tetrahydrofuran, the mixture was stirred for 30 minutes. [Intermediate 1-d] (30g, 58mmol) was dissolved in 300ml of tetrahydrofuran and 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 separated by column to obtain [Formula 1-e]. (29.1g, 92%)

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

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

Under nitrogen conditions, [Intermediate 1-e] (29g, 55mmol) and bismuth (III) trifluoromethanesulfonate (1.8g, 2.8mmol) were added to 300ml of 1,2-dichloroethane and 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]. (23.2g, 82%)

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

[Intermediate 1-f] [Compound 17]

[Intermediate 1-f] (10g, 19.6mmol), bis(4-biphenyl)amine (6.3g, 19.6mmol), bisdibenzylideneacetone dipalladium (0.2g, 0.4mmol), BINAP (0.5mmol) under nitrogen conditions g, 0.8 mmol) and sodium tertiary butoxide (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 separated by column to obtain [Compound 17]. (11.8g, 72%)

MS (MALDI-TOF): m/z 751.29 [M ⁺ ]

Synthesis Example 2. Synthesis of Compound 18

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

[Intermediate 2-a]

[Intermediate 2-a] was obtained by synthesizing in the same manner except that 3-chlorophenol was used instead of 4-chlorophenol used in Synthesis Example 1-(1). (68g, 69%)

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

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

[Intermediate 2-b] was obtained by synthesizing in the same manner except that [Intermediate 2-a] was used instead of [Intermediate 1-a] used in Synthesis Example 1-(2). (57g, 72%)

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

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

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

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

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

[Intermediate 2-d] was obtained by synthesizing in the same manner except that [Intermediate 2-c] was used instead of [Intermediate 1-c] used in Synthesis Example 1-(4). (28g, 62%)

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

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

[Intermediate 2-e] was obtained by synthesizing in the same manner except that [Intermediate 2-d] was used instead of [Intermediate 1-d] used in Synthesis Example 1-(5). (25g, 88%)

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

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

[Intermediate 2-f] was obtained by synthesizing in the same manner except that [Intermediate 2-e] was used instead of [Intermediate 1-e] used in Synthesis Example 1-(6). (20g, 85%)

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

[Intermediate 2-f] [Compound 18]

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

MS (MALDI-TOF): m/z 751.29 [M ⁺ ]

Synthesis Example 3. Synthesis of Compound 28

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

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

[Intermediate 3-a] was obtained by synthesizing in the same manner except that 2,4-dibromobenzaldehyde was used instead of 2,5-dibromobenzaldehyde used in Synthesis Example 2-(4). (29g, 59%)

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

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

[Intermediate 3-b] was obtained by synthesizing in the same manner except that [Intermediate 3-a] was used instead of [Intermediate 1-d] used in Synthesis Example 1-(5). (26g, 89%)

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

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

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

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

[Intermediate 3-c] [Compound 28]

[Intermediate 3-c] was used instead of [Intermediate 1-f] used in Synthesis Example 1-(7), and bis(9,9-dimethyl-9 H -fluorene-7 instead of bis(4-biphenyl)amine [Compound 28] was obtained by synthesizing in the same manner except that -yl)amine was used. (13g, 65%)

MS (MALDI-TOF): m/z 831.35 [M ⁺ ]

Synthesis Example 4. Synthesis of Compound 57

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

[Intermediate 4-a]

[Intermediate 4-a] was obtained by synthesizing in the same manner except that 2-chlorophenol was used instead of 4-chlorophenol used in Synthesis Example 1-(1). (52g, 66%)

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

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

[Intermediate 4-b] was obtained by synthesizing in the same manner except that [Intermediate 4-a] was used instead of [Intermediate 1-a] used in Synthesis Example 1-(2). (49g, 75%)

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

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

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

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

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

[Intermediate 4-d] was obtained by synthesizing in the same manner except that [Intermediate 4-c] was used instead of [Intermediate 1-c] used in Synthesis Example 1-(4). (23g, 59%)

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

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

[Intermediate 4-e] was obtained by synthesizing in the same manner except that [Intermediate 4-d] was used instead of [Intermediate 1-d] used in Synthesis Example 1-(5). (20g, 91%)

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

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

[Intermediate 4-f] was obtained by synthesizing in the same manner except that [Intermediate 4-e] was used instead of [Intermediate 1-e] used in Synthesis Example 1-(6). (14g, 79%)

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

[Intermediate 4-f] [Compound 57]

[Intermediate 4-f] was used instead of [Intermediate 1-f] used in Synthesis Example 1-(7), and N- [4-(1-naphthyl)phenyl]-4 instead of bis(4-biphenyl)amine [Compound 57] was obtained by synthesizing in the same manner except that biphenylamine was used. (11g, 66%)

Synthesis Example 5. Synthesis of Compound 58

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

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

[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. Thus, [Intermediate 5-a] was obtained. (34g, 62%)

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

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

[Intermediate 5-b] was obtained by synthesizing in the same manner except that [Intermediate 5-a] was used instead of [Intermediate 1-d] used in Synthesis Example 1-(5). (28g, 93%)

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

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

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

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

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

[Intermediate 5-c] (23g, 53mmol) and 200 m of tetrahydrofuran were added under nitrogen, and the mixture was cooled to minus 78°C. After 30 minutes, 1.6M n-butyllithium (50mL, 79mmol) was slowly added dropwise, followed by stirring at room temperature for 2 hours. Trimethylborate (8.2g, 79mmol) was slowly added dropwise at 78°C below zero, and the mixture was stirred at room temperature for 2 hours. The reaction was terminated by adding an aqueous hydrochloric acid solution, and the organic layer was extracted and concentrated under reduced pressure. Crystals were formed with hexane, and the solid was filtered and dried to obtain [Intermediate 5-d]. (18 g, 71%)

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

[Intermediate 5-e]

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

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

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

[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 in the same manner. Synthesis gave [Compound 58]. (9g, 53%)

MS (MALDI-TOF): m/z 765.27 [M ⁺ ]

Synthesis Example 6. Synthesis of Compound 81

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

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

Intermediate 6-a was synthesized in the same manner except that 2-bromo biphenyl was used instead of 2,5-dibromobenzaldehyde used in Synthesis Example 1-(4). (44g, 59%)

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

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

[Intermediate 6-a] (40g, 82.5mmol), 80mL of nitromethane, and 400mL of dichloromethane were added under nitrogen, and the mixture was cooled to 0°C. After adding iron trichloride (40.1 g, 247 mmol), the mixture was stirred at room temperature for 1 hour. Crystals were formed using methanol, filtered and dried to obtain [Intermediate 6-b]. (31g, 57%)

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

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

[Intermediate 6-b] (30g, 62.1mmol) was added to 300 mL of tetrahydrofuran under nitrogen and then cooled to minus 78°C. N-butyllithium (47mL, 74.6mmol) was slowly added dropwise and then stirred 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. Extraction was performed using an aqueous solution of sodium thiosulfate, and the organic layer was concentrated under reduced pressure. [Formula 6-c] was obtained by forming crystals with hexane, filtering, and drying. (38g, 46%)

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

[Intermediate 6-c] [Compound 81]

Except for using [Intermediate 6-c] instead of [Intermediate 1-f] used in Synthesis Example 1-(7) and using N-biphenyl 4-dibenzofuranamine instead of bis(4-biphenyl)amine [Compound 81] was obtained by synthesizing in the same manner. (12g, 63%)

MS (MALDI-TOF): m/z 815.28 [M ⁺ ]

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 by synthesizing in the same manner except that [Intermediate 1-f] was used instead of [Intermediate 1-b] used in Synthesis Example 1-(3). (25g, 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-1,3, [Compound 101] was obtained by synthesizing in the same manner except for using 5-triazine. (11g, 66%)

MS (MALDI-TOF): m/z 663.23 [M ⁺ ]

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

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

[Intermediate 8-a] [Compound 123]

[Intermediate 8-a] was used instead of [Intermediate 1-c] used in Synthesis Example 1-(4), and 2-chloro-4-naphthyl-6-phenyl-1, [Compound 123] was obtained by synthesizing in the same manner except for using 3,5 triazine. (10 g, 62%)

MS (MALDI-TOF): m/z 713.25 [M ⁺ ]

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 by synthesizing in the same manner except that [Intermediate 3-c] was used instead of [Intermediate 1-b] used in Synthesis Example 1-(3). (15g, 78%)

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

[Intermediate 9-a] [Compound 124]

[Compound 124] was obtained in the same manner except that [Intermediate 9-a] was used instead of [Intermediate 7-a] used in Synthesis Example 7-(2). (15g, 78%)

MS (MALDI-TOF): m/z 663.23 [M ⁺ ]

Synthesis Example 10. Synthesis of Compound 163

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

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

[Intermediate 10-a] was obtained by synthesizing in the same manner except that [Intermediate 4-f] was used instead of [Intermediate 1-b] used in Synthesis Example 1-(3). (12g, 72%)

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

[Intermediate 10-a] [Compound 163]

Except for using [Intermediate 10-a] instead of [Intermediate 1-c] used in Synthesis Example 1-(4) and using 2-chloro-4-phenyl quinazoline instead of 2,5-dibromobenzaldehyde [Compound 163] was obtained by synthesizing in the same manner. (8 g, 65%)

MS (MALDI-TOF): m/z 636.22 [M ⁺ ]

Synthesis Example 11. Synthesis of Compound 164

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

[Intermediate 5-d] [Compound 164]

Except for using 2-(3-bromo-phenyl)-4,6-diphenyl-1,3,5-triazine instead of [Intermediate 5-e] used in Synthesis Example 5-(6), the same [Compound 164] was obtained through the synthesis method. (9g, 51%)

MS (MALDI-TOF): m/z 739.26 [M ⁺ ]

Synthesis Example 12. Synthesis of Compound 180

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

[Intermediate 8-a] [Compound 180]

2-chloro-3-(dibenzo[b,d]turan-4-yl instead of 2-chloro-4-naphthyl-6-phenyl-1,3,5triazine used in Synthesis Example 8-(2) [Compound 180] was obtained by synthesizing in the same manner except for using )-6-phenyl-1,3,5-triazine. (11g, 64%)

MS (MALDI-TOF): m/z 753.24 [M ⁺ ]

Examples 1 to 14: Preparation of blue organic light emitting device

Examples 1 to 14 below are examples in which the organic compound represented by Formula A according to the present invention is used as a material for a hole auxiliary layer in an organic light emitting device, and the manufacturing method of the organic light emitting device is as follows.

After the ITO glass was patterned so that the light emitting area had a size of 2 mm × 2 mm, it was cleaned. After mounting the substrate in a vacuum chamber, the base pressure was set to 1 × 10 ^-6 torr, and organic materials were formed on the ITO in the order of HATCN (50 Å) and NPD (600 Å), and then as a hole auxiliary layer according to Table 1 below. , The compound prepared according to the present invention was formed into a film (50 Å), and doped with 5 wt% of a blue host (BH) + blue dopant (BD) to form a light emitting layer having a thickness of 200 Å. [ET]:Liq = 1:1 (300 Å), Liq (10 Å), Al (1,000 Å) were formed in this order, and the measurement was performed at 0.4 mA. The structures of [HATCN], [NPD], [BH], [BD], [Liq] and [ET] are as follows.

<HATCN> <NPD>

<BH> <BD>

<Liq> <ET>

Comparative Example 1

An organic light emitting device was manufactured in the same manner as in Examples 1 to 14, except that the hole auxiliary layer was not used and NPD (650 Å) was used.

For the organic electroluminescent device manufactured according to Examples 1 to 14 and Comparative Example 1, voltage, current, luminance, color coordinates and lifetime were measured, and the results are shown in [Table 1]. Here, T95 means the time required for the luminance to decrease to 95% compared to the initial luminance (2000 cd/m2).

division hole auxiliary 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 by the present invention is used as a hole auxiliary layer, it can be seen that it has higher efficiency and longer lifespan than Comparative Example 1, and thus manufacture of an organic light emitting device that can have improved characteristics indicates that it can be used.

Examples 15 to 27: Preparation of organic electroluminescent device

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

The ITO glass was patterned so that the light emitting area had a size of 2 mm x 2 mm, and then washed. After the substrate is mounted in a vacuum chamber, the base pressure is 1x10-6 torr, and then the organic material is placed on the ITO with HATCN (50Å), NPD (650Å), blue host (BH) + blue dopant ( BD) A light emitting layer having a thickness of 200 Å was formed by doping with 5 wt%. Compounds prepared by the present invention: Films were formed in the order of Liq = 1:1 (300 Å), Liq (10 Å), and Al (1,000 Å), and the measurement was performed 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 manufactured in the same manner as the device structure of the above example, except that ET, which is generally used as an electron transport layer material, was used instead of the compound prepared by the invention, and the structure of the ET is as follows. .

[ET]

For the prepared organic light emitting device manufactured according to Examples 15 to 27 and Comparative Example 2, voltage, current, luminance, color coordinates and lifetime were measured, and the results are shown in [Table 2]. Here, T95 means the time required for the luminance to decrease to 95% compared to 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 by the present invention has higher efficiency, lower driving voltage and longer lifespan than ET, which is widely used as an electron transport layer material.

Claims (17)

An organic compound represented by the following [Formula A].
[Formula A]

In the above [Formula A],
One of Q1 and Q2 is an aromatic hydrocarbon ring selected from phenanthrene, triphenylene, and pyrene, and the other is a benzene ring,
Ar1 to Ar4 are the same or different, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted carbon atom having 6 carbon atoms to 50 aryl groups, substituted or unsubstituted arylalkyl groups having 7 to 50 carbon atoms, cyano groups, nitro groups, halogen groups, alkylsilyl groups having 1 to 24 carbon atoms, and arylsilyl groups having 6 to 24 carbon atoms. Or, or any one substituent selected from the following [Formula A] to [Formula Q], wherein one of Ar1 to Ar2 is any one substituent selected from the following [Formula A] to [Formula Q],
In the aromatic hydrocarbon rings of Q1 and Q2 and the lower two benzene rings in Formula A, the carbon atoms of the aromatic rings not bonded to Ar1 to Ar4 are bonded to hydrogen or deuterium, respectively,
[Formula A] [Formula B] [Formula C]

[Formula D] [Formula E] [Formula F]

[Formula G] [Formula H] [Formula I]

[Formula J] [Formula K] [Formula L]

[Formula M] [Formula N] [Formula O]

[Formula P] [Formula Q]

In the [Structural Formula A] to [Structural Formula Q],
The linking groups L1 to L3 are each the same or different, and independently any one selected from a single bond and a substituted or unsubstituted arylene group having 6 to 60 carbon atoms,
wherein p1 to p3 are each 1;
In the above [structural formula A],
R1 to R2 are the same or different, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted carbon atom having 6 carbon atoms to 50 aryl groups, substituted or unsubstituted arylalkyl groups having 7 to 50 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms having O, N or S as heteroatoms, cyano groups, nitro groups, halogen groups , Any one selected from an alkylsilyl group having 1 to 24 carbon atoms and an arylsilyl group having 6 to 24 carbon atoms,
In the [Formula B] to [Formula Q],
R1 to R9 are the same or different, and independently of each other, hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted carbon atom having 6 carbon atoms to 50 aryl groups, substituted or unsubstituted arylalkyl groups having 7 to 50 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms having O, N or S as heteroatoms, cyano groups, nitro groups, halogen groups , Any one selected from an alkylsilyl group having 1 to 24 carbon atoms and an arylsilyl group having 6 to 24 carbon atoms,
The substituent Ra in [Formula Q] is a substituted or unsubstituted carbazole,
The '-*' refers to a single bond bonded to Q1, Q2 or carbon atoms of two benzene rings located at the bottom in Formula A,
Here, 'substitution' in 'substituted or unsubstituted' means deuterium, cyano group, halogen group, nitro group, C1-24 alkyl group, C1-24 halogenated alkyl group, C6-24 carbon atom group. It means substituted with one or more substituents selected from the group consisting of an aryl group, an arylalkyl group having 7 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, and an arylsilyl group having 6 to 24 carbon atoms. delete delete delete delete According to claim 1
Linking groups L1 to L3 are each the same or different, and independently of each other, are single bonds or selected from the following [Formula 22], [Formula 23], [Formula 25], [Formula 27], [Formula 28] and [Formula 30] An organic compound, characterized in that any one of which is.
[Structural Formula 22] [Structural Formula 23] [Structural Formula 25]

[Formula 27] [Formula 28] [Formula 30]

In Structural Formula 22, Structural Formula 23, Structural Formula 25, Structural Formula 27, Structural Formula 28 and Structural Formula 30, hydrogen or deuterium is bonded to the carbon site of the aromatic ring. According to claim 1,
The organic compound, characterized in that Ar3 and Ar4 are the same as or different from each other, and each independently represent hydrogen or deuterium. According to claim 1,
An organic compound, characterized in that one of Ar1 to Ar2 is [Structural Formula A]. According to claim 1,
An organic compound, characterized in that one of Ar1 to Ar2 is any one of [Formula B] to [Formula H]. According to claim 1,
An organic compound, characterized in that one of Ar1 to Ar2 is any one of [Structural Formula I] to [Structural Formula P]. According to claim 1,
The compound represented by [Formula A] is the following <Compound 1> to <Compound 7>, <Compound 9> to <Compound 13>, <Compound 17> to <Compound 23>, <Compound 25> to <Compound 31> , <Compound 33> to <Compound 38>, <Compound 41> to <Compound 44>, <Compound 46>, <Compound 49> to <Compound 51>, <Compound 53> to <Compound 55>, <Compound 57> to <Compound 61>, <Compound 63>, <Compound 65> to <Compound 68>, <Compound 71>, <Compound 74>, <Compound 77> to <Compound 83>, <Compound 85> to <Compound 89><Compound91>,<Compound93> to <Compound 98>, <Compound 100> to <Compound 105>, <Compound 109> to <Compound 114>, <Compound 117> to <Compound 130>, <Compound 133> to <Compound 139>, <Compound 141> to <Compound 150>, <Compound 153> to <Compound 159>, <Compound 161> to <Compound 188>, <Compound 193> to <Compound 198>, <Compound 201> to <Compound 223>, <Compound 225> to <Compound 227>, and <Compound 229> to <Compound 231>.
<Compound 1><Compound2><Compound3><Compound4>

<Compound 5><Compound6><Compound7>

<Compound 9><Compound10><Compound11><Compound12>

<Compound 13>

<Compound 17><Compound18><Compound19><Compound20>

<Compound 21><Compound22><Compound23>

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

<Compound 29><Compound30><Compound31>

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

<Compound 37><Compound38>

<Compound 41><Compound42><Compound43><Compound44>

<Compound 46>

<Compound 49><Compound50><Compound51>

<Compound 53><Compound54><Compound55>

<Compound 57><Compound58><Compound59><Compound60>

<Compound 61><Compound63>

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

<Compound 71><Compound74>

<Compound 77><Compound78><Compound79><Compound80>

<Compound 81><Compound82><Compound83>

<Compound 85><Compound86><Compound87><Compound88>

<Compound 89><Compound91>

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

<Compound 97><Compound98><Compound100>

<Compound 101><Compound102><Compound103><Compound104>

<Compound 105>

<Compound 109><Compound110><Compound111><Compound112>

<Compound 113><Compound114>

<Compound 117><Compound118><Compound119><Compound120>

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

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

<Compound 129><Compound130>

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

<Compound 137><Compound138><Compound139><Compound140>

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

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

<Compound 149><Compound150>

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

<Compound 157><Compound158><Compound159>

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

<Compound 197><Compound198>

<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>

<Compound 221><Compound222><Compound223>

<Compound 225><Compound226><Compound227>

<Compound 229><Compound230><Compound231>

a first electrode;
a second electrode facing the first electrode; and
An organic light emitting device comprising an organic layer interposed between the first electrode and the second electrode,
An organic light emitting device characterized in that the organic layer contains the organic compound according to any one of claims 1 and 6 to 11. According to claim 12,
The organic light emitting device includes at least one of a hole injection layer, a hole transport layer, a hole auxiliary 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. device. According to claim 13,
The organic compound is an organic light emitting device, characterized in that used for the hole auxiliary layer. According to claim 13,
The organic light emitting device, characterized in that the organic compound is used for the electron transport layer. According to claim 13,
At least one layer selected from the respective layers is an organic light emitting device, characterized in that formed by a deposition process or a solution process. According to claim 12,
The organic light emitting diode may include a flat panel display device; flexible display devices; devices for monochromatic or white flat lighting; And, a monochromatic or white flexible lighting device; characterized in that used in any one device selected from the organic light emitting device.

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