KR20150132660A - Organic light-emitting device - Google Patents

Abstract

An organic light emitting device is disclosed. The organic light emitting device comprises a first electrode; a second electrode; a light emitting layer interposed between the first electrode and the second electrode; and a hole transport area interposed between the first electrode and the light emitting layer.

Description

Organic light-emitting device

Embodiments of the present invention relate to an organic light emitting device.

An organic light-emitting device is a self-light-emitting device having a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed characteristics, and being able to have multiple colors .

A hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially formed on the first electrode in the organic light emitting device. Lt; / RTI > structure. The holes injected from the first electrode migrate to the light emitting layer via the hole transporting region and electrons injected from the second electrode migrate to the light emitting layer via the electron transporting region. The carriers such as holes and electrons recombine in the light emitting layer region to generate an exiton. This exciton changes from the excited state to the ground state and light is generated.

Embodiments of the present invention provide an organic light emitting device.

One embodiment of the present invention is a liquid crystal display comprising: a first electrode; A second electrode; A light emitting layer interposed between the first electrode and the second electrode; And a hole transporting region interposed between the first electrode and the light emitting layer, wherein the hole transporting region includes an auxiliary layer, and the auxiliary layer comprises an amine compound represented by the following Formula 1: Initiate:

≪ Formula 1 >

&Lt; Formula 2-1 > < Formula 2-2 > < Formula 2-3 &

Among the above-mentioned formulas (1) and (2-1) to (2-3)

L ₁₁ is a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene, a substituted or unsubstituted Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene, substituted or unsubstituted C ₆ -C ₆₀ arylene, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic a diabalent non-aromatic condensed polycycle and a substituted or unsubstituted divalent non-aromatic condensed heteropolycycle;

a11 is selected from 0, 1, 2, 3, 4, 5 and 6;

R ₁₁ and R ₁₂ are, independently of each other, a substituted or unsubstituted C ₁ -C ₆₀ alkyl, substituted or unsubstituted C ₆ -C ₆₀ aryl, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl, A substituted monovalent non-aromatic condensed polycyclic and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic ring, with the proviso that substituted or unsubstituted dibenzofuranyl is excluded;

R ₁₃ is selected from the groups represented by the above formulas (2-1) to (2-3);

R ₂₁ to R ₂₇ are each independently of the other hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and its salts, Substituted or unsubstituted C ₁ -C ₆₀ alkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₆ -C ₆₀ aryl, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl, Substituted or unsubstituted monovalent non-aromatic condensed polycyclic, substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic and -N (Q ₁ ) (Q ₂ );

b22 and b24 are independently selected from 1, 2, 3 and 4;

b23 and 27 are independently of each other selected from 1, 2 and 3;

The substituted C ₃ -C ₁₀ cycloalkylene, substituted C ₁ -C ₁₀ hetero cycloalkylene, substituted C ₃ -C ₁₀ cycloalkyl alkenylene, substituted C ₁ -C ₁₀ heterocycloalkyl alkenylene, substituted C ₆ -C ₆₀ arylene, substituted C ₁ -C ₆₀ heteroarylene, substituted divalent non-aromatic fused polycyclic, unsubstituted bivalent aromatic condensed polycyclic heteroaryl, a C ₁ -C ₆₀ alkyl, substituted At least one of C ₃ -C ₁₀ cycloalkyl, substituted C ₆ -C ₆₀ aryl, substituted C ₁ -C ₆₀ heteroaryl, substituted monovalent non-aromatic condensed polycyclic and substituted monovalent non-aromatic heterocyclic polycyclic &Lt; / RTI &gt;

C ₁ -C ₆ alkyl, C ₂ -C ₆ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acids and salts thereof, ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl and C ₁ -C ₆₀ alkoxy;

Deuterium, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazines, hydrazones, carboxyl and salts thereof, acid and salts thereof, phosphoric acid and salts thereof, C ₃ -C ₁₀ cycloalkyl, C ₃ - C ₃ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio (arylthio), C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic one and is a non-alkenyl aromatic hydrocarbon ring condensed with at least one of the polycyclic substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ al, C ₂ -C ₆₀ alkynyl and C ₁ -C ₆₀ alkoxy;

C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy , C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic heterocyclic polycyclic;

C ₁ -C ₆ alkyl, C ₂ -C ₆ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acids and salts thereof, ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₁ -C ₆₀ alkoxy, C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ hetero cycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic one and is a non-aromatic heterocyclic at least one of the substituted condensed polycyclic, C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heteroaryl cycloalkenyl, C ₆ -C ₆₀ aryl , C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic heterocyclic polycyclic; And

Selected from _{-N (Q 11) (Q 12} ) and;

Q ₁ , Q ₂ , Q ₁₁ and Q ₁₂ are independently from each other selected from hydrogen, deuterium, C ₁ -C ₆₀ alkyl and C ₆ -C ₆₀ aryl;

* Is a nitrogen atom of formula (1) or a binding site with L &lt; ₁₁ &gt;.

The organic light emitting diode according to an exemplary embodiment of the present invention may have a low driving voltage, a high efficiency, and a long life.

1 is a schematic view illustrating a structure of an organic light emitting diode according to an embodiment of the present invention.
1 is a schematic view illustrating a structure of an organic light emitting diode according to another embodiment of the present invention.

BRIEF DESCRIPTION OF THE DRAWINGS The present invention is capable of various modifications and various embodiments, and specific embodiments are illustrated in the drawings and described in detail in the detailed description. The effects and features of the present invention and methods of achieving them will be apparent with reference to the embodiments described in detail below with reference to the drawings. The present invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein.

Hereinafter, exemplary embodiments of the present invention will be described in detail with reference to the accompanying drawings, wherein like reference numerals refer to like or corresponding components throughout the drawings, and a duplicate description thereof will be omitted .

In the following examples, the singular forms "a", "an" and "the" include plural referents unless the context clearly dictates otherwise.

In the following embodiments, terms such as inclusive or possessive are intended to mean that a feature, or element, described in the specification is present, and does not preclude the possibility that one or more other features or elements may be added.

In the following embodiments, when a part of a film, an area, a component or the like is on or on another part, not only the case where the part is directly on the other part but also another film, area, And the like.

In the drawings, components may be exaggerated or reduced in size for convenience of explanation. For example, the size and thickness of each component shown in the drawings are arbitrarily shown for convenience of explanation, and thus the present invention is not necessarily limited to those shown in the drawings.

In the present specification, the phrase "(organic layer) includes at least one amine-based compound" means that one or more amine compounds belonging to the category of the above formula (1) Amine-based compound ".

In the present specification, the term "organic layer" refers to all single layers and / or plural layers interposed between the first electrode and the second electrode of the organic light emitting device. The material contained in the layer of the "organic layer" is not limited to an organic material.

A substrate may be further disposed below the first electrode 110 or over the second electrode 190 of FIG. The substrate may be a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness.

The first electrode 110 may be formed, for example, by providing a first electrode material on the substrate using a deposition method, a sputtering method, or the like. When the first electrode 110 is an anode, the first electrode material may be selected from materials having a high work function to facilitate hole injection. The first electrode 110 may be a reflective electrode, a transflective electrode, or a transmissive electrode. As the material for the first 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 can be used. (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), or the like is used as the first electrode material for forming the first electrode 110 which is a translucent electrode or a reflective electrode. ), Magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag).

The first electrode 110 may have a single layer or a multilayer structure having a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the present invention is not limited thereto.

An organic layer 150 is disposed on the first electrode 110. The organic layer 150 includes a light emitting layer 160.

The organic layer 150 may further include a hole transport region 130 interposed between the first electrode and the light emitting layer. The organic layer 150 may further include an electron transport region 180 interposed between the light emitting layer and the second electrode.

The hole transport region 130 may include an auxiliary layer 140 and may further include at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL) But is not limited thereto. The electron transport region 180 may include at least one of a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL). However, the present invention is not limited thereto.

The hole transporting region may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multi-layered structure having a plurality of layers made of a plurality of different materials.

For example, the hole transporting region may have a structure of a single layer composed of a plurality of different materials, or may have a structure of a hole injection layer / hole transporting layer / auxiliary layer stacked sequentially from the first electrode 110, Layer or hole transporting layer / auxiliary layer structure, but the present invention is not limited thereto.

When the hole transporting region includes a hole injection layer, a vacuum evaporation method, a spin coating method, a casting method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal imaging (LITI) The hole injection layer may be formed on the first electrode 110 by using various methods.

When the hole injection layer is formed by vacuum deposition, the deposition conditions may include, for example, a deposition temperature of about 100 to about 500 DEG C, a vacuum degree of about 10 ^-8 to about ^10-3 torr, and a deposition rate of about 0.01 to about 100 A / sec The hole injection layer structure to be formed and the hole injection layer structure to be formed within the deposition rate range of the hole injection layer to be formed.

When the hole injection layer is formed by the spin coating method, the coating conditions include a compound for a hole injection layer to be deposited and a hole for formation to be formed within a range of a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature range of about 80 [ Can be selected in consideration of the injection layer structure.

When the hole transporting region includes a hole transporting layer, the hole transporting layer may be formed by a vacuum evaporation method, a spin coating method, a casting method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal imaging The hole transport layer may be formed on the first electrode 110 or on the hole injection layer using various methods. When the hole transport layer is formed by the vacuum deposition method and the spin coating method, the deposition conditions and the coating conditions of the hole transport layer refer to the deposition conditions and the coating conditions of the hole injection layer.

The hole-transporting region may be at least one selected from the group consisting of m-MTDATA, TDATA, 2-TNATA, NPB, beta-NPB, TPD, Spiro- TPD, Spiro- NPB, alpha -NPB, TAPC, HMTPD, TCTA (N-carbazolyl) triphenylamine), Pani / DBSA (polyaniline / dodecylbenzenesulfonic acid), PEDOT / PSS Poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate) / poly (4-styrenesulfonate) / Pani / CSA (polyaniline / camphor sulfonicacid) Styrene sulfonate), PANI / PSS (polyaniline) / poly (4-styrenesulfonate) / poly (4-styrenesulfonate)), a compound represented by the following formula 201 and a compound represented by the following formula can do:

&Lt; Formula 201 >

&Lt; EMI ID =

Of the above formulas (201) and (202)

The descriptions for L ₂₀₁ to L ₂₀₅ are independent of each other, see the description of L ₁₁ in the present specification;

xa1 to xa4 are independently selected from 0, 1, 2 and 3;

xa5 is selected from 1, 2, 3, 4 and 5;

The descriptions of R ₂₀₁ to R ₂₀₅ independently of each other refer to the description of R ₂₁ in the present specification.

For example, of the above formulas (201) and (202)

L ₂₀₁ to L ₂₀₅ independently from each other,

And examples thereof include phenylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorene, dibenzofluorene, phenanthrenylene, anthracenylene, pyrenylene, chrysinylene, pyridinylene, pyrazinylene, Pyrimidinylene, pyridazinylene, quinolinylene, isoquinolinylene, quinoxalinylene, quinazolinylene, carbazolylene and triazienylene; And

C ₁ -C ₂₀ alkyl, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and its salts, _{Wherein R is} selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, Phenylene, naphthylene, fluorenylene, spy which is substituted with at least one of pyridazinyl, pyridazinyl, isoindolyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, Cyclohexylene, pyridazinylene, pyridazinylene, pyridazinylene, pyrimidinylene, pyridazinylene, pyrimidinylene, pyridazinylene, pyrimidinylene, pyridazinylene, Quinolinylene, isoquinolinylene, quinoxalinylene, quinazolinylene, Zolylene and triazinylene; ;

xa1 to xa4 are, independently of each other, 0, 1 or 2;

xa &lt; 5 &gt; is 1, 2 or 3;

R ₂₀₁ to R ₂₀₅ , independently of each other,

Phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, Pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl; And

C ₁ -C ₂₀ alkyl, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and its salts, _20-alkoxy, phenyl, naphthyl, azulenyl, fluorenyl, a spy-fluorenyl, benzo fluorenyl, dibenzo fluorenyl, phenanthrenyl, anthracenyl, pie alkylenyl, Cry anthracenyl, pyridinyl, Phenyl, naphthyl, fluorenyl, spiro, substituted with at least one of pyridinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, A heterocyclic group such as a fluorenyl, a fluorenyl, a benzofluorenyl, a dibenzofluorenyl, a phenanthrenyl, an anthracenyl, a pyrenyl, a klycenyl, a pyridinyl, a pyrazinyl, a pyrimidinyl, a pyridazinyl, a quinolinyl, Naphthyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl; , But is not limited thereto.

The compound represented by Formula 201 may be represented by the following Formula 201A:

&Lt; Formula 201A >

For example, the compound represented by Formula 201 may be represented by the following Formula 201A-1, but is not limited thereto:

<Formula 201A-1>

The compound represented by the formula (202) may be represented by the following formula (202A), but is not limited thereto:

&Lt; Formula 202A >

The description of L ₂₀₁ to L ₂₀₃ , xa 1 to xa 3, xa 5 and R ₂₀₂ to R ₂₀₄ in the above formulas 201A, 201A-1 and 202A is as described in this specification, and R ₂₁₁ refers to the description of R ₂₀₃ , R ₂₁₃ to R ₂₁₆ independently represent hydrogen, deuterium, a halogen atom, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and its salts, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₁ -C ₆₀ alkoxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ heterocycloalkyl, C C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl and non- - aromatic condensed polycyclic groups.

For example, of the above formulas 201A, 201A-1 and 202A,

L ₂₀₁ to L ₂₀₃ independently from each other,

A substituted or unsubstituted heteroarylene group such as phenylen, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, pyrenylene, Pyrimidinylene, pyridazinylene, quinolinylene, isoquinolinylene, quinoxalinylene, quinazolinylene, carbazolylene, and triazienylene; And

C ₁ -C ₂₀ alkyl, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and its salts, _{Wherein R is} selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, Phenylene, naphthylene, fluorenylene, spiro-flu, substituted with at least one member selected from the group consisting of pyridyl, pyridazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinazolinyl, Anthracenylene, pyrenylene, klychenylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazienylene, quinolinylene, benzenetrafluoroethylene, dibenzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, pyrenylene, , Isoquinolinylene, quinoxalinylene, quinazolinylene, Ylene and triazinyl alkylene; ;

xa1 to xa3 are, independently of each other, 0 or 1;

R ₂₀₃ , R ₂₁₁ and R ₂₁₂ , independently of each other,

Phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, Pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl; And

C ₁ -C ₂₀ alkyl, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and its salts, _{Wherein R is} selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, Phenyl, naphthyl, fluorenyl, spiro-fluoro, substituted with at least one member selected from the group consisting of phenyl, naphthyl, pyridazinyl, quinolinyl, Anthracenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyrimidinyl, pyrimidinyl, pyrazinyl, pyrazinyl, pyrazinyl, phenanthryl, Decanyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl , Carbazolyl, and triazinyl; ;

R &lt; ₂₁₃ &gt; and R &lt; ₂₁₄ &

C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy;

Wherein R is selected from the group consisting of hydrogen, deuterium, halogen atoms, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acids and salts thereof, phosphoric acid and salts thereof, A heterocyclic group such as a fluorenyl, a fluorenyl, a benzofluorenyl, a dibenzofluorenyl, a phenanthrenyl, an anthracenyl, a pyrenyl, a klycenyl, a pyridinyl, a pyrazinyl, a pyrimidinyl, a pyridazinyl, a quinolinyl, C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy, which is substituted with at least one selected from nitrogen, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl;

Phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, Pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl; And

C ₁ -C ₂₀ alkyl, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and its salts, _{Wherein R is} selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, Phenyl, naphthyl, fluorenyl, spiro-fluoro, substituted with at least one member selected from the group consisting of phenyl, naphthyl, pyridazinyl, quinolinyl, Wherein R is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, Salinyl, quinazolinyl, carbazolyl and triazinyl; ;

R ₂₁₅ and R ₂₁₆ , independently of each other,

Wherein R is hydrogen, deuterium, halogen atom, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acids and salts thereof,

C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy;

Wherein R is selected from the group consisting of hydrogen, deuterium, halogen atoms, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acids and salts thereof, phosphoric acid and salts thereof, A heterocyclic group such as a fluorenyl, a fluorenyl, a benzofluorenyl, a dibenzofluorenyl, a phenanthrenyl, an anthracenyl, a pyrenyl, a klycenyl, a pyridinyl, a pyrazinyl, a pyrimidinyl, a pyridazinyl, a quinolinyl, C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy, which is substituted with at least one selected from nitrogen, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl;

Phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, Pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, and triazinyl; And

C ₁ -C ₂₀ alkyl, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and its salts, _{Wherein R is} selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, Phenyl, naphthyl, fluorenyl, spiro-fluoro, substituted with at least one member selected from the group consisting of phenyl, naphthyl, pyridazinyl, quinolinyl, Wherein R is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, Salinyl, quinazolinyl, carbazolyl and triazinyl; ;

xa5 is 1 or 2;

In the above formulas 201A and 201A-1, R ₂₁₃ and R ₂₁₄ may combine with each other to form a saturated or unsaturated ring.

The compound represented by Formula 201 and the compound represented by Formula 202 may include the following compounds HT1 to HT20, but are not limited thereto.

The thickness of the hole transporting region may be from about 100 A to about 10,000 A, for example, from about 100 A to about 1000 A. When the hole transporting region includes both the hole injecting layer and the hole transporting layer, the thickness of the hole injecting layer is about 100 Å to about 10,000 Å, for example, about 100 Å to about 1000 Å, and the thickness of the hole transporting layer is about 50 Å For example, from about 100 A to about 1500 A, for example. When the thicknesses of the hole transporting region, the hole injecting layer, and the hole transporting layer satisfy the above-described ranges, satisfactory hole transporting characteristics can be obtained without substantially increasing the driving voltage.

In addition to the materials described above, the hole transporting region may further include a charge-generating material for improving conductivity. The charge-generating material may be uniformly or non-uniformly dispersed within the hole transport region.

The charge-producing material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of the p-dopant include tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone di Quinone derivatives such as phosphorus (F4-TCNQ); Metal oxides such as tungsten oxide and molybdenum oxide; And the following compound HT-D1, but the present invention is not limited thereto.

<Compound HT-D1> <F4-TCNQ>

The auxiliary layer may include an amine compound represented by the following general formula (1).

&Lt; Formula 1 >

Wherein L ₁₁ is a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene , Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene, substituted or unsubstituted C ₆ -C ₆₀ arylene, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene, substituted or unsubstituted divalent A non-aromatic condensed polycycle and a substituted or unsubstituted divalent non-aromatic condensed heteropolycycle. The term &quot; non-aromatic condensed polycycle &quot;

For example, in the above formula (1), L &lt; ₁₁ &gt;

And examples thereof include phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthylene ( acenaphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluoranenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoro But are not limited to, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, But are not limited to, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, coronenylene, ovalenylene, pyrrolylene, thiophenyl Thiophenylene, furanylene, imida The present invention relates to a process for producing a polyol (hereinafter referred to as &quot; polyol &quot;), a polyol, a polyol, a polyol, a polyol, a polyol, a polyol, a polyol, pyrazinylene, pyrimidinylene, pyridazinylene, isoindolylene, indolylene, indazolylene, purinylene, quinolinylene, quinolinylene, , Isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cyinolinylene, the present invention relates to a process for producing a cinnolinyl derivative of the general formula (1), wherein the cinnolinylene, carbazolylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzoimidazolylene, (benzofuranylene), There may be mentioned benzothiophenylene, isobenzothiazolylene, benzooxazolylene, isobenzooxazolylene, triazolylene, tetrazolylene, oxadiazole, Examples of the dibenzothiophenylene derivatives include oxadiazolylene, triazinylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, and imidazopyridyl. Nylene; And

C ₁ -C ₂₀ alkyl, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and its salts, ₂₀ alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pental alkylenyl, indenyl, naphthyl, azulenyl, heptal alkylenyl, indazol hexenyl, acetoxy-naphthyl, fluorenyl, spy Fluorenyl, triphenylenyl, pyrenyl, crycenyl, naphthacenyl, picenyl, perylenyl, phenanthryl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, , Pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrroyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl , Pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, inda Wherein R is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, alkynyl, alkynyl, alkynyl, alkynyl, alkynyl, alkynyl, alkynyl, alkynyl, Benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzothiophene, benzothiophenyl, Phenyl, phenanthrenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene substituted with at least one of phenyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl and imidazopyridinyl , Acenaphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylenylene, pie Rhenylene, klychenylene, naphthacenylene, pichenylene , Pyrenylenylene, pentaphenylene, hexacenylene, pentacenylene, rubisenylene, coronenylene, ovalenylene, pyrrolylene, thiophenylene, furanylene, imidazolyl, pyrazolylene, thiazolylene , Isothiazolylene, oxazolylene, isoxazolylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazienylene, isoindolylene, indoleylene, indazolylene, purinylene, quinolinylene, iso And examples thereof include quinolinylene, benzoquinolinylene, phthalazienylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cyanolylene, carbazolylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene , Benzoimidazolylene, benzofuranylene, benzothiophenylene, isobenzothiazolylene, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, di Benzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocaine, Sol ylene, thiadiazol-ylene and already jopi piperidinyl alkenylene; , But is not limited thereto.

As another example, L &lt; ₁₁ &gt;

Phenylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, triphenylenylene, pyrenylene and chlorenylene; And

Phenyl, naphthyl, fluorenyl, spiro-fluorenylene, benzofluorenylene, substituted phenyl, naphthyl, fluorenyl, pyridinyl, pyrazinyl, pyrimidinyl, thiophenyl and furanyl substituted with at least one of , Dibenzofluorenylene, phenanthrenylene, anthracenylene, triphenylrenylene, pyrenylene and chrysinylene; , But is not limited thereto.

As another example, in the above formula (1), L ₁₁ may be a group selected from among the following formulas (3-1) to (3-8), but is not limited thereto:

Among the above-mentioned formulas (3-1) to (3-8)

Z ₁ and Z ₂ are each independently selected from a hydrogen atom, phenyl, naphthyl, fluorenyl, pyridinyl, pyrazinyl, pyrimidinyl, thiophenyl and furanyl,

d1 is selected from integers from 1 to 4;

d2 is selected from integers from 1 to 3;

d3 is selected from integers from 1 to 6;

d4 is selected from integers from 1 to 8;

d6 is selected from integers from 1 to 5;

* And * are binding sites with neighboring atoms.

As another example, in the above formula (1), L ₁₁ may be a group selected from among the following formulas (4-1) to (4-8), but is not limited thereto:

As another example, in the above formula (1), L ₁₁ may be a group selected from among the following formulas (4-1) to (4-8), but is not limited thereto:

In the above formulas 4-1 to 4-8

* And * are binding sites with neighboring atoms.

In the above formula (1), a11 represents the number of L ₁₁ , and a11 may be selected from 0, 1, 2, 3, 4, 5 and 6. When a11 is an integer of 2 or more, a plurality of L &lt; ₁₁ &gt; may be the same as or different from each other. If a11 is 0 (L _{11) a11;} means a direct bond. For example, in formula (1), a11 may be an integer of 0, 1 or 2, but is not limited thereto.

Wherein R ₁₁ and R ₁₂ independently represent a substituted or unsubstituted C ₁ -C ₆₀ alkyl, a substituted or unsubstituted C ₆ -C ₆₀ aryl, a substituted or unsubstituted C ₁ -C ₆₀ hetero Aryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic and substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic ring, with the proviso that substituted or unsubstituted dibenzofuranyl is excluded;

The substituted C ₁ -C ₆₀ alkyl, substituted C ₆ -C ₆₀ aryl, substituted C ₁ -C ₆₀ heteroaryl, substituted monovalent non-aromatic condensed polycyclic and substituted monovalent non-aromatic heterocyclic polycyclic The at least one substituent may be,

C ₁ -C ₆ alkyl, C ₂ -C ₆ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acids and salts thereof, ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl and C ₁ -C ₆₀ alkoxy;

Deuterium, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazines, hydrazones, carboxyl and salts thereof, acid and salts thereof, phosphoric acid and salts thereof, C ₃ -C ₁₀ cycloalkyl, C ₃ - C ₃ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio (arylthio), C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic one and is a non-alkenyl aromatic hydrocarbon ring condensed with at least one of the polycyclic substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ al, C ₂ -C ₆₀ alkynyl and C ₁ -C ₆₀ alkoxy;

C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy , C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic heterocyclic polycyclic; And

C ₁ -C ₆ alkyl, C ₂ -C ₆ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acids and salts thereof, ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₁ -C ₆₀ alkoxy, C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ hetero cycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic one and is a non-aromatic heterocyclic at least one of the substituted condensed polycyclic, C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heteroaryl cycloalkenyl, C ₆ -C ₆₀ aryl , C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic heterocyclic polycyclic; &Lt; / RTI &gt;

For example, In the formula 1, R ₁₁ and R ₁₂ represent, independently of each other,

But are not limited to, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, But are not limited to, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, But are not limited to, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, But are not limited to, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, Pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyridyl, pyrimidinyl, Pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, pyrimidinyl, , Isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, ), Carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzofuranyl, Benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triaryl, triazolyl, Triazinyl, dibenzothiophenyl, benzocarbazolyl, dibenzo &lt; RTI ID = 0.0 &gt; Bar jolil, thiadiazole and imidazole jolil jopi piperidinyl; And

Heavy hydrogen, 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 salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl Im import and C ₂ -C ₆₀ heteroaryl group, at least one substituted phenyl selected from the group consisting of , Phenalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenan Thienyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, klycenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, , Pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrroyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl Pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl Benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, , Triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl and imidazopyridinyl; , But is not limited thereto.

As another example, R &lt; ₁₁ &gt; and R &lt; ₁₂ &

Phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, triphenylenyl, pyrenyl, klycenyl, pyridinyl, pyrimidinyl Thiophenyl, furanyl, carbazolyl, benzofuranyl, benzothiophenyl, dibenzothiophenyl, benzocarbazolyl, benzothiophenyl, benzothiophenyl, benzothiophenyl, benzoxazolyl, And dibenzocarbazolyl; And

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, halogen atom, cyano group, nitro group, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, triphenylenyl, pyrenyl, pyridinyl, Phenyl, naphthyl, fluorenyl, spiro-fluorenylsubstituted by at least one of the following: halogen, cyano, cyano, , Benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, triphenylenyl, pyrenyl, klycenyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, naphthyridyl Neu, quinoxalinyl, quinazolinyl, thiophenyl, furanyl, carbazolyl, benzofuranyl, benzothiophenyl, dibenzothiophenyl, benzocarbazolyl and dibenzocarbazolyl; , But is not limited thereto.

As another example, R &lt; ₁₁ &gt; and R &lt; ₁₂ &

Phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, triphenylenyl, pyrenyl, crycenyl, carbazolyl, benzocarbazolyl and dibenzocarbazolyl; And

Naphthyl, fluorenyl, phenanthrenyl, anthracenyl, phenanthrenyl, and the like substituted with at least one of a halogen atom, a halogen atom, a cyano group, a nitro group, phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, Triphenylenyl, pyrenyl, crycyenyl, carbazolyl, benzocarbazolyl and dibenzocarbazolyl; , But is not limited thereto.

As another example, in the above formula (1), R ₁₁ and R ₁₂ may be independently selected from the group consisting of the following formulas (5-1) to (5-23), but are not limited thereto:

Of the above-mentioned formulas (5-1) to (5-23)

* Is the binding site with neighboring atoms.

In the general formula (1), R ₁₃ may be selected from the groups represented by the general formulas (2-1) to (2-3)

&Lt; Formula 2-1 > < Formula 2-2 > < Formula 2-3 &

Of the above-mentioned formulas (2-1) to (2-3)

R ₂₁ to R ₂₇ are each independently of the other hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and its salts, Substituted or unsubstituted C ₁ -C ₆₀ alkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₆ -C ₆₀ aryl, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl, Substituted or unsubstituted monovalent non-aromatic condensed polycyclic, substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic and -N (Q ₁ ) (Q ₂ );

Said substituted C ₁ -C ₆₀ alkyl, substituted C ₃ -C ₁₀ cycloalkyl, substituted C ₆ -C ₆₀ aryl, substituted C ₁ -C ₆₀ heteroaryl, substituted monovalent non-aromatic condensed polycyclic and substituted At least one substituent of the monovalent non-aromatic heterocyclic polycyclic ring,

C ₁ -C ₆ alkyl, C ₂ -C ₆ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acids and salts thereof, ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl and C ₁ -C ₆₀ alkoxy;

Deuterium, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazines, hydrazones, carboxyl and salts thereof, acid and salts thereof, phosphoric acid and salts thereof, C ₃ -C ₁₀ cycloalkyl, C ₃ - C ₃ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio (arylthio), C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic one and is a non-alkenyl aromatic hydrocarbon ring condensed with at least one of the polycyclic substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ al, C ₂ -C ₆₀ alkynyl and C ₁ -C ₆₀ alkoxy;

C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy , C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic heterocyclic polycyclic;

C ₁ -C ₆ alkyl, C ₂ -C ₆ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acids and salts thereof, ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₁ -C ₆₀ alkoxy, C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ hetero cycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic one and is a non-aromatic heterocyclic at least one of the substituted condensed polycyclic, C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heteroaryl cycloalkenyl, C ₆ -C ₆₀ aryl , C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic heterocyclic polycyclic; And

Selected from _{-N (Q 11) (Q 12} ) and;

Q ₁ , Q ₂ , Q ₁₁ and Q ₁₂ are independently from each other selected from hydrogen, deuterium, C ₁ -C ₆₀ alkyl and C ₆ -C ₆₀ aryl;

b22 and b24 are independently selected from 1, 2, 3 and 4;

b23 and 27 are independently of each other selected from 1, 2 and 3;

* Is a nitrogen atom of formula (1) or a binding site with L &lt; ₁₁ &gt;.

For example, in the above formula (1), R ₁₃ may be selected from the group represented by the following formulas (2-1a), (2-2a), (2-2b) and (2-3a)

&Lt; Formula 2-1a &

<Formula 2-2a>

(2-2b)

<Formula 2-3a>

Of the 2-1a, 2-2a, 2-2b and 2-3a,

R ₂₁ to R ₂₇ and b ₂₂ to b ₂₇ refer to the foregoing.

As another example, in the above formula (1), R ₁₃ may be selected from the group represented by the following formulas (2-1a), (2-2a), (2-2b) and (2-3a)

&Lt; Formula 2-1a &

<Formula 2-2a>

(2-2b)

<Formula 2-3a>

Of the 2-1a, 2-2a, 2-2b and 2-3a,

R ₂₁ to R ₂₇ independently represent hydrogen, deuterium, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, But are not limited to, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, (S) selected from spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, Pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, naphthacenyl, naphthacenyl, But are not limited to, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, Isomers of pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, And examples thereof include pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolyl, Benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl (such as benzoquinolinyl, phthalazinyl, naphthyridinyl, quinazolinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, ), Tetrazolyl, oxadiazolyl, triazinyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl, and -N (Q ₁ ) (Q ₂ ); And

Heavy hydrogen, 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 salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl Im import and C ₂ -C ₆₀ heteroaryl groups substituted with at least one selected from the group consisting of methyl Butyl, isobutyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, Thienyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrene, fluorenyl, Naphthyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, , Thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl , Benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzo Benzothiophenyl, benzothiazolyl, benzooxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazole Zolyl and imidazopyridinyl; ;

Q ₁ and Q ₂ are each independently selected from C ₆ -C ₆₀ aryl;

b22 and b24 are independently selected from 1, 2, 3 and 4;

b23 is selected from 1, 2, and 3.

As another example, in the above formula (1), R ₁₃ may be selected from the group represented by the following formulas (2-1a), (2-2a), (2-2b) and (2-3a)

&Lt; Formula 2-1a &

<Formula 2-2a>

(2-2b)

Of the above-mentioned formulas (2-1a), (2-2a), (2-2b) and (2-3a)

R ₂₁ to R ₂₄ independently represent hydrogen, deuterium, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec- Ph) ₂ ;

b22 and b24 are independently selected from 1, 2, 3 and 4;

b23 is selected from 1, 2, and 3.

In one embodiment, the amine compound represented by Formula 1 may be represented by any one of the following Chemical Formulas 1A to 1D, but is not limited thereto:

&Lt;

&Lt; Formula 1B >

&Lt; Formula 1C >

&Lt; Formula 1D >

Among the above general formulas (1A) to (1D)

L ₁₁ , a11, R ₁₁ , R ₁₂ , R ₂₁ to R _27, and b ₂₂ to b ₂₇ refer to the foregoing.

In another embodiment, when the amine compound represented by Formula 1 is represented by any one of Chemical Formulas 1A to 1C, L &lt; ₁₁ &gt; in Chemical Formulas 1A to 1D is a group selected from Chemical Formulas 4-1 to 4-8 ego; a11 may be an integer of 0, 1 or 2, but is not limited thereto.

In another embodiment, when the amine compound represented by Formula 1 is represented by any one of Chemical Formulas 1A to 1D, R ₁₁ and R ₁₂ are independently selected from the groups represented by Chemical Formulas 5-1 to 5-23 But is not limited thereto.

In still another embodiment, when the amine compound represented by Formula 1 is represented by any one of Chemical Formulas 1A to 1D, R ₂₁ to R ₂₄ independently represent hydrogen, deuterium, methyl, ethyl, n- , iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, phenyl and naphthyl; b22 and b24 are independently selected from 1, 2, 3 and 4; b23 may be selected from 1, 2, and 3, but is not limited thereto.

In another embodiment, the amine compound represented by Formula 1 may be selected from the following compounds 1 to 12, but is not limited thereto:

The thickness of the auxiliary layer may be from about 10 Angstroms to about 100 Angstroms, for example from about 30 Angstroms to about 80 Angstroms. When the thickness of the auxiliary layer satisfies the above-described range, satisfactory hole transporting characteristics can be obtained without substantial increase in driving voltage.

Since the auxiliary layer has good hole injection and mobility, it is possible to provide an organic light emitting device having improved characteristics.

An auxiliary layer 140 may be present at any location in the hole transport region 130.

Alternatively, the auxiliary layer 240 may be disposed in contact with the light emitting layer 260.

A vacuum deposition method, a spin coating method, a casting method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal imaging (LITI) method, or the like is performed on the first electrode 110 or the hole transporting region. ) And the like are used to form a light emitting layer. When the light emitting layer is formed by the vacuum deposition method and the spin coating method, the deposition condition and the coating condition of the light emitting layer refer to the deposition condition and the coating condition of the hole injection layer.

When the organic light emitting device 10 is a full color organic light emitting device, it may be patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer for each light emitting layer and individual sub-pixels. Alternatively, the light emitting layer may have a structure in which a red light emitting layer, a green light emitting layer, and a blue light emitting layer are laminated or a structure in which a red light emitting material, a green light emitting material and a blue light emitting material are mixed without layering, and emits white light. Alternatively, the light emitting layer may be a white light emitting layer, and may further include a color converting layer or a color filter that converts the white light into light of a desired color.

The light emitting layer may include a host and a dopant.

The host may comprise at least one of the following TPBi, TBADN, ADN, CBP, CDBP and TCP:

Alternatively, the host may include a compound represented by Formula 301 below.

&Lt; Formula 301 >

Ar ₃₀₁ - [(L ₃₀₁ ) _{xb 1} -R ₃₀₁ ] _{xb 2}

In Formula 301,

Ar _&lt;

And examples thereof include naphthalene, heptalene, fluorenene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, But are not limited to, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, Indenoanthracene;

C ₁ -C ₆ alkyl, C ₂ -C ₆ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acids and salts thereof, ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₁ -C ₆₀ alkoxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ hetero cycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl group, a non-condensed polycyclic aromatic group and a -Si (Q ₃₀₁₎ ( Q ₃₀₂ ) (Q ₃₀₃ ) wherein Q ₃₀₁ to Q ₃₀₃ are each independently of the other hydrogen, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₆ -C ₆₀ aryl and C ₂ -C ₆₀ heteroaryl Fluorine, pyrene, fluorine, benzene, fluorine, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, Wren, Kraisen, I Tasen, pisen, perylene, penta pen and indeno anthracene; ;

For a description of L ₃₀₁ , see the discussion of L ₂₀₁ herein;

R ₃₀₁ is

C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy;

Wherein R is selected from the group consisting of hydrogen, deuterium, halogen atoms, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acids and salts thereof, phosphoric acid and salts thereof, A heterocyclic group such as a fluorenyl, a fluorenyl, a benzofluorenyl, a dibenzofluorenyl, a phenanthrenyl, an anthracenyl, a pyrenyl, a klycenyl, a pyridinyl, a pyrazinyl, a pyrimidinyl, a pyridazinyl, a quinolinyl, C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy, which is substituted with at least one selected from nitrogen, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl;

Phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, Pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazole and triazinyl; And

C ₁ -C ₂₀ alkyl, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and its salts, _{Wherein R is} selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, Phenyl, naphthyl, fluorenyl, spiro-fluoro, substituted with at least one member selected from the group consisting of phenyl, naphthyl, pyridazinyl, quinolinyl, Wherein R is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, Salinyl, quinazolinyl, carbazolyl and triazinyl; ;

xb1 is selected from 0, 1, 2 and 3;

xb2 is selected from 1, 2, 3 and 4.

For example, in Formula 301,

L ₃₀₁ ,

Phenylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, pyrenylene and chlorenylene; And

C ₁ -C ₂₀ alkyl, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and its salts, _20-alkoxy, phenyl, naphthyl, fluorenyl, a spy-fluorenyl, benzo fluorenyl, dibenzo fluorenyl, phenanthrenyl, anthracenyl, pie alkylenyl and Cry enyl at least one substituted phenyl selected from the group consisting of Naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, pyrenylene and klychenylene; ;

R ₃₀₁ is

C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy;

Wherein R is selected from the group consisting of hydrogen, deuterium, halogen atoms, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acids and salts thereof, phosphoric acid and salts thereof, C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy, substituted with at least one selected from fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl and crecenyl;

Phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl and klycenyl; And

C ₁ -C ₂₀ alkyl, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and its salts, _20-alkoxy, phenyl, naphthyl, fluorenyl, a spy-fluorenyl, benzo fluorenyl, dibenzo fluorenyl, phenanthrenyl, anthracenyl, pie alkylenyl and Cry enyl at least one substituted phenyl selected from the group consisting of , Naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl and klycenyl; , But is not limited thereto.

The compound represented by Formula 301 may include, but is not limited to, at least one of the following compounds H1 to H42:

Alternatively, the host may include, but is not limited to, at least one of the following compounds H43 to H49:

The dopant may include at least one of a fluorescent dopant and a phosphorescent dopant.

The phosphorescent dopant may include an organometallic complex represented by the following formula (401): &lt; EMI ID =

&Lt; Formula 401 >

In the above formula (401)

M is selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thorium (TM);

X ₄₀₁ to X ₄₀₄ independently of one another are nitrogen or carbon;

The A ₄₀₁ and A ₄₀₂ rings may be, independently of one another, substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted spirofluorene, substituted or unsubstituted indene Substituted or unsubstituted thiophenes, substituted or unsubstituted thiophenes, substituted or unsubstituted furan, substituted or unsubstituted imidazoles, substituted or unsubstituted pyrazoles, substituted or unsubstituted thiols, substituted or unsubstituted thiophenes, Substituted or unsubstituted thiazoles, substituted or unsubstituted isothiazoles, substituted or unsubstituted oxazoles, substituted or unsubstituted isoxazoles, substituted or unsubstituted pyridines, substituted or unsubstituted pyrazines, substituted or unsubstituted pyrimidines, Substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazoline, substituted or unsubstituted quinazoline, substituted or unsubstituted quinazoline, substituted or unsubstituted quinazoline, substituted or unsubstituted quinazoline, substituted or unsubstituted quinazoline, Substituted or unsubstituted benzoimidazoles, substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophenes, substituted or unsubstituted isobenzothiophenes, substituted or unsubstituted benzothiophenes, substituted or unsubstituted benzothiophenes, Substituted or unsubstituted benzoxazole, substituted or unsubstituted benzoxazole, substituted or unsubstituted isobenzoxazole, substituted or unsubstituted triazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted triazine, substituted or unsubstituted dibenzofuran, And substituted or unsubstituted dibenzothiophene;

The substituted benzene, substituted naphthalene, substituted fluorene, substituted spiro-fluorene, substituted indene, substituted pyrrole, substituted thiophene, substituted furan, substituted imidazole, substituted pyrazole, Substituted thiazoles, substituted thiazoles, substituted isothiazoles, substituted oxazoles, substituted isoxazoles, substituted pyridines, substituted pyrazines, substituted pyrimidines, substituted pyridazines, substituted quinolines, substituted isoquinolines, Substituted quinoxaline, substituted quinazoline, substituted carbazole, substituted benzoimidazole, substituted benzofuran, substituted benzothiophene, substituted isobenzothiophene, substituted benzoxazole, substituted iso At least one substituent of the benzooxazole, the substituted triazole, the substituted oxadiazole, the substituted triazine, the substituted dibenzofuran and the substituted dibenzothiophene,

C ₁ -C ₆ alkyl, C ₂ -C ₆ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acids and salts thereof, ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl and C ₁ -C ₆₀ alkoxy;

Deuterium, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazines, hydrazones, carboxyl and salts thereof, acid and salts thereof, phosphoric acid and salts thereof, C ₃ -C ₁₀ cycloalkyl, C ₃ - C ₃ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio (arylthio), C ₂ -C ₆₀ heteroaryl group, a non-condensed polycyclic aromatic group (non-aromatic condensed polycyclic group) , -N (Q 401) (Q 402), -Si (Q 403) (Q 404) (Q ₄₀₅₎ and _{-B (Q 406) (Q 407} ) of the at least one substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl and C ₁ -C ₆₀ alkoxy;

C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy , C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl, and non-aromatic condensed polycyclic groups;

C ₁ -C ₆ alkyl, C ₂ -C ₆ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acids and salts thereof, ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₁ -C ₆₀ alkoxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ (Q ₄₁₁ ) (optionally substituted with one or _more substituents selected from the group consisting of C ₁ -C ₆ alkoxy, heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl, _{Q 412), -Si (Q 413} ) (Q 414) (Q 415) and _{-B (Q 416) (Q 417} ) of the at least one substituted, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ heterocycloalkyl Alkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ hetero Aryl and non-aromatic condensed polycyclic groups; And

Q ₄₂₁ , Q ₄₂₂ , Q ₄₂₃ , Q ₄₂₄ , Q ₄₂₅ , and -B Q ₄₂₆ , Q ₄₂₇ ; ;

L ₄₀₁ is an organic ligand;

xc1 is 1, 2 or 3;

xc2 is 0, 1, 2 or 3;

The L ₄₀₁ may be any monovalent, divalent or trivalent organic ligand. For example, L ₄₀₁ may be a halogen ligand (e.g. Cl, F), a diketone ligand (e.g., acetylacetonate, 1,3-diphenyl-l, 3- propanedionate, 6,6-tetramethyl-3,5-heptanedionate, hexafluoroacetonate), carboxylic acid ligands (e.g., picolinate, dimethyl-3-pyrazolecarboxylate, benzoate), carbon But are not limited to, monooxide ligands, isonitrile ligands, cyano ligands, and phosphorus ligands (e.g., phosphine, phosphaite).

If the formula of A 401 ₄₀₁ is to have two or more substituents, bonded to each other at least two substituents of A ₄₀₁ can form a saturated or unsaturated ring.

If the formula of A 401 ₄₀₂ is to have two or more substituents, bonded to each other at least two substituents of A ₄₀₂ can form a saturated or unsaturated ring.

는 서로 동일하거나 상이할 수 있다. 상기 화학식 401 중 xc1이 2 이상일 경우, A₄₀₁ 및 A₄₀₂는 각각 이웃하는 다른 리간드의 A₄₀₁ 및 A₄₀₂와 각각 직접(directly) 또는 연결기(예를 들면, C₁-C₅알킬렌, -N(R')-(여기서, R'은 C₁-C₁₀알킬기 또는 C₆-C₂₀아릴기임) 또는 -C(=O)-)를 사이에 두고 연결될 수 있다.When xc1 in Formula 401 is 2 or more, a plurality of ligands of Formula 401

May be the same or different from each other. If the formula xc1 401 is 2 or more of, A ₄₀₁ and A ₄₀₂ are each of the other ligands neighboring A and ₄₀₁ respectively direct and A ₄₀₂ (directly) or linking group (e.g., C ₁ -C ₅ alkylene, -N (R ') - (wherein, R' - may be connected across a) is C ₁ -C ₁₀ alkyl or C ₆ -C ₂₀ aryl group), or -C (= O).

The phosphorescent dopant may include, but is not limited to, at least one of the following compounds PD1 to PD74:

Alternatively, the phosphorescent dopant may comprise the following PtOEP:

The fluorescent dopant may include at least one of DPAVBi, BDAVBi, TBPe, DCM, DCJTB, Coumarin 6, and C545T.

Alternatively, the fluorescent dopant may include a compound represented by the following formula (501):

<Formula 501>

In the above formula (501)

Ar ₅₀₁

And examples thereof include naphthalene, heptalene, fluorenene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, But are not limited to, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, Indenoanthracene;

C ₁ -C ₆ alkyl, C ₂ -C ₆ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acids and salts thereof, ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₁ -C ₆₀ alkoxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ hetero cycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl group, a non-condensed polycyclic aromatic group and a -Si (Q ₅₀₁₎ ( Q ₅₀₂ ) (Q ₅₀₃ ) wherein Q ₅₀₁ to Q ₅₀₃ are each independently of the other hydrogen, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₆ -C ₆₀ aryl and C ₂ -C ₆₀ heteroaryl Fluorine, pyrene, fluorine, benzene, fluorine, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, Wren, Kraisen, I Tasen, pisen, perylene, penta pen and indeno anthracene; ;

The descriptions of L ₅₀₁ to L ₅₀₃ refer to the description of L ₂₀₁ in the present specification, respectively;

R ₅₀₁ and R ₅₀₂ , independently of each other,

Phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, Pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazole, triazinyl, dibenzofuranyl and dibenzothiophenyl; And

C ₁ -C ₂₀ alkyl, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and its salts, _{Wherein R is} selected from the group consisting of hydrogen, alkyl, alkoxy, phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, Naphthyl, which is substituted by at least one member selected from the group consisting of pyridyl, pyridazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinazolinyl, carbazolyl, triazinyl, dibenzofuranyl and dibenzothiophenyl , Pyrenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, klycenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, Quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, Azinyl and dibenzo-furanyl and dibenzo-thiophenyl; ;

xd1 to xd3 are independently selected from 0, 1, 2 and 3;

xb4 is selected from 1, 2, 3 and 4.

The fluorescent dopant may comprise at least one of the following compounds FD1 to FD8:

The content of the dopant in the light emitting layer may be selected from the range of about 0.01 to about 15 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

The thickness of the light emitting layer may be about 100 Å to about 1000 Å, for example, about 200 Å to about 600 Å. When the thickness of the light-emitting layer satisfies the above-described range, it is possible to exhibit excellent light-emitting characteristics without substantial increase in driving voltage.

Next, an electron transporting region 180 may be disposed above the light emitting layer.

The electron transport region 180 may include at least one of a hole blocking layer, an electron transport layer (ETL), and an electron injection layer, but is not limited thereto.

For example, the electron transporting region 180 may have a structure of an electron transporting layer / electron injecting layer or a hole blocking layer / electron transporting layer / electron injecting layer sequentially stacked from the light emitting layer, but the present invention is not limited thereto.

The electron transporting region may include a hole blocking layer. The hole blocking layer may be formed to prevent the triplet excitons or holes from diffusing into the electron transporting layer when the light emitting layer is a phosphorescent dopant.

When the electron transporting region includes a hole blocking layer, a vacuum evaporation method, a spin coating method, a casting method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal imaging (LITI) The hole blocking layer may be formed on the light emitting layer. When the hole blocking layer is formed by the vacuum deposition method and the spin coating method, the deposition conditions and the coating conditions of the hole blocking layer refer to the deposition conditions and the coating conditions of the hole injection layer.

The hole blocking layer may include, for example, at least one of the following BCP and Bphen, but is not limited thereto.

The thickness of the hole blocking layer may be about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer satisfies the above-described range, excellent hole blocking characteristics can be obtained without increasing the driving voltage substantially.

The electron transporting region may include an electron transporting layer. The electron transport layer may be formed using various methods such as vacuum deposition, spin coating, casting, LB method, inkjet printing, laser printing, and laser induced thermal imaging (LITI) And may be formed on the light emitting layer or on the hole blocking layer. When the electron transport layer is formed by the vacuum deposition method and the spin coating method, the deposition conditions and the coating conditions of the electron transport layer refer to the deposition conditions and coating conditions of the hole injection layer.

The electron transport layer may include at least one of the BCP, Bphen and to Alq _3, Balq, TAZ and NTAZ.

Alternatively, the electron transporting layer may include at least one of the compounds represented by the following formula (601):

<Formula 601>

Ar ₆₀₁ - [(L ₆₀₁ ) _{xe 1} -E ₆₀₁ ] _{xe 2}

In the above formula (601)

Ar ₆₀₁

And examples thereof include naphthalene, heptalene, fluorenene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, But are not limited to, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, Indenoanthracene;

C ₁ -C ₆ alkyl, C ₂ -C ₆ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acids and salts thereof, ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₁ -C ₆₀ alkoxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ hetero cycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl group, a non-condensed polycyclic aromatic group and a -Si (Q ₃₀₁₎ ( Q ₃₀₂ ) (Q ₃₀₃ ) wherein Q ₃₀₁ to Q ₃₀₃ are each independently of the other hydrogen, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₆ -C ₆₀ aryl and C ₂ -C ₆₀ heteroaryl Fluorine, pyrene, fluorine, benzene, fluorine, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, Wren, Kraisen, I Tasen, pisen, perylene, penta pen and indeno anthracene; ;

For a description of L ₆₀₁ , see the discussion of L ₂₀₁ herein;

E ₆₀₁ ,

Pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, thiazolyl, Isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, indolyl, ), Purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, ), Quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoyl, phenanthrolinyl, For example, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, But are not limited to, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzo Dibenzothiophenyl, benzocarbazolyl and dibenzocarbazolyl; And

C ₁ -C ₂₀ alkyl, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and its salts, _20-alkoxy, phenyl, pental alkylenyl, indenyl, naphthyl, azulenyl, heptal alkylenyl, indazol hexenyl, acetoxy-naphthyl, fluorenyl, a spy-fluorenyl, benzo fluorenyl, dibenzo fluorenyl, Naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, naphthyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, Pyrimidinyl, pyridazinyl, isoindole, pyrimidinyl, pyrimidinyl, pyrimidinyl, pyrimidinyl, pyrimidinyl, imidazolyl, isothiazolyl, isoxazolyl, isoxazolyl, isoxazolyl, Yl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, Benzothiophenyl, isobenzothiazole, benzothiophenyl, benzothiophene, benzothiophene, benzothiophene, benzothiophene, benzothiophene, benzothiophene, benzothiophene, Substituted or unsubstituted pyrrolyl, which is substituted with at least one of benzoyl, benzoyl, benzoyl, benzoyl, benzoyl, benzoyl, benzoyl, benzoyl, benzoyl, benzoyl, benzoyl, benzooxazolyl, benzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, , Thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, Wherein the aryl group is selected from the group consisting of pyridyl, quinolyl, quinolinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, Phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothio Carbonyl, iso jolil benzothiazole, benzoxazole jolil, iso jolil benzoxazole, triazole jolil, tetra jolil, oxadiazolyl jolil, triazinyl, dibenzo-furanyl, dibenzo-thiophenyl, benzo and dibenzo-carbazole carbazole jolil jolil; ;

xe1 is selected from 0, 1, 2 and 3;

xe2 is selected from 1, 2, 3 and 4.

Alternatively, the electron transporting layer may include at least one of compounds represented by the following formula (602):

<Formula 602>

In the above formula (602)

₆₁₁ X is N or _{C- (L 611) xe611 -R 611} , X 612 is N or _{C- (L 612) xe612 -R 612} , X 613 is N or C- (L _{613) xe613} -R _613, and , At least one of X ₆₁₁ to X ₆₁₃ is N;

For a description of each of L ₆₁₁ to L ₆₁₆ , refer to the description of L ₂₀₁ in this specification;

R ₆₁₁ to R ₆₁₆ , independently of each other,

Phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, Pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl; And

C ₁ -C ₂₀ alkyl, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and its salts, _20-alkoxy, phenyl, naphthyl, azulenyl, fluorenyl, a spy-fluorenyl, benzo fluorenyl, dibenzo fluorenyl, phenanthrenyl, anthracenyl, pie alkylenyl, Cry anthracenyl, pyridinyl, Phenyl, naphthyl, fluorenyl, spiro, substituted with at least one of pyridinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, A heterocyclic group such as a fluorenyl, a fluorenyl, a benzofluorenyl, a dibenzofluorenyl, a phenanthrenyl, an anthracenyl, a pyrenyl, a klycenyl, a pyridinyl, a pyrazinyl, a pyrimidinyl, a pyridazinyl, a quinolinyl, Naphthyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl; ;

xe611 to xe616 are independently selected from 0, 1, 2 and 3;

The compound represented by Formula 601 and the compound represented by Formula 602 may include at least one of the following compounds ET1 to ET15.

The thickness of the electron transporting layer may be about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transporting layer satisfies the above-described range, satisfactory electron transporting characteristics can be obtained without substantially increasing the driving voltage.

The electron transporting layer may further include a metal-containing material in addition to the above-described materials.

The metal-containing material may comprise a Li complex. The Li complex may include, for example, the following compound ET-D1 (lithium quinolate, LiQ) or ET-D2.

The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190.

The electron injecting layer may be formed using various methods such as vacuum deposition, spin coating, casting, LB method, inkjet printing, laser printing, and laser induced thermal imaging (LITI) , And on the electron transport layer. When the electron injection layer is formed by the vacuum deposition method and the spin coating method, the deposition conditions and the coating conditions of the electron injection layer refer to the deposition conditions and coating conditions of the hole injection layer.

The electron injection layer may include at least one selected from LiF, NaCl, CsF, Li ₂ O, BaO and LiQ.

The thickness of the electron injection 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.

The second electrode 190 is disposed on the organic layer 150 as described above. The second electrode 190 may be a cathode, which is an electron injection electrode. At this time, the material for the second electrode 190 may be a metal, an alloy, an electrically conductive compound having a low work function, Can be used. Specific examples of the material for the second electrode 190 include Li, Mg, Al, Al-Li, Ca, Mg-In, , Magnesium-silver (Mg-Ag), and the like. Alternatively, ITO or IZO may be used as the material for the second electrode 190. The second electrode 190 may be a reflective electrode, a transflective electrode, or a transmissive electrode.

The organic light emitting device has been described above with reference to FIG. 1, but the present invention is not limited thereto.

In the present specification, C ₁ -C ₆₀ alkyl means a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms. Specific examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, ter- Butyl, pentyl, iso-amyl, hexyl, and the like. In the present specification, C ₁ -C ₆₀ alkylene means a divalent group having the same structure as the above C ₁ -C ₆₀ alkyl.

In the present specification, C ₁ -C ₆₀ alkoxy means a monovalent group having the formula -OA ₁₀₁ (wherein A ₁₀₁ is the above C ₁ -C ₆₀ alkyl), and specific examples thereof include methoxy, ethoxy , Isopropyloxy, and the like.

In the present specification, C ₂ -C ₆₀ alkenyl means a hydrocarbon group containing at least one carbon-carbon double bond at the middle or end of the C ₂ -C ₆₀ alkyl. Specific examples thereof include ethenyl, propenyl, butenyl, etc. . In the present specification, C ₂ -C ₆₀ alkenylene means a divalent group having the same structure as the C ₂ -C ₆₀ alkenyl.

In the present specification, C ₂ -C ₆₀ alkynyl means a hydrocarbon group containing at least one carbon-carbon triple bond at the middle or end of the C ₂ -C ₆₀ alkyl group. Specific examples thereof include ethynyl, propynyl propynyl, and the like. In the present specification, C ₂ -C ₆₀ alkynylene means a divalent group having the same structure as the above C ₂ -C ₆₀ alkynyl.

In the present specification, C ₃ -C ₁₀ cycloalkyl means a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, examples of which include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like do. In the present specification, C ₃ -C ₁₀ cycloalkylene means a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkyl.

In the present specification, C ₃ -C ₁₀ heterocycloalkyl means a monovalent monocyclic group having 3 to 10 carbon atoms including at least one heteroatom selected from N, O, P and S as a ring-forming atom, Specific examples include tetrahydrofuranyl, tetrahydrothiophenyl, and the like. In the present specification, C ₃ -C ₁₀ heterocycloalkylene means a divalent group having the same structure as the above-mentioned C ₃ -C ₁₀ heterocycloalkyl.

In the present specification, C ₃ -C ₁₀ cycloalkenyl is a monovalent monocyclic group having 3 to 10 carbon atoms, which has at least one double bond in the ring, but does not have aromatics, Examples include cyclopentenyl, cyclohexenyl, cycloheptenyl, and the like. In the present specification, C ₃ -C ₁₀ cycloalkenylene means a divalent group having the same structure as the above-mentioned C ₃ -C ₁₀ cycloalkenyl.

In the present specification, C ₃ -C ₁₀ heterocycloalkenyl is a monovalent monocyclic group having 3 to 10 carbon atoms including at least one hetero atom selected from N, O, P and S as a ring-forming atom, It has one double bond. The C ₃ -C ₁₀ Specific examples of the heterocycloalkyl alkenyl, and the like 2,3-dihydro-furanyl, 2,3-dihydro-thiophenyl. In the present specification, C ₃ -C ₁₀ heterocycloalkenylene means a divalent group having the same structure as the above-mentioned C ₃ -C ₁₀ heterocycloalkenyl.

In the present specification, C ₆ -C ₆₀ aryl means a monovalent group having 6 to 60 carbon atoms in the carbocyclic aromatic system, and C ₆ -C ₆₀ arylene has 6 to 60 carbon atoms, Quot; means a divalent group having a cyclic aromatic system. Specific examples of the C ₆ -C ₆₀ aryl include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, crycenyl, and the like. The C ₆ -C ₆₀ aryl and C ₆ -C ₆₀ aryl If the alkylene contains 2 or more rings, the 2 or more rings may be fused to each other.

As used herein, C ₂ -C ₆₀ heteroaryl means a monovalent group comprising at least one heteroatom selected from N, O, P and S as ring-forming atoms and having a carbocyclic aromatic system having from 2 to 60 carbon atoms And C ₂ -C ₆₀ heteroarylene means a divalent group having at least one heteroatom selected from N, O, P and S as a ring-forming atom and having a carbocyclic aromatic system having from 2 to 60 carbon atoms do. Specific examples of the C ₂ -C ₆₀ heteroaryl include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl and the like. When said C ₂ -C ₆₀ heteroaryl and C ₂ -C ₆₀ heteroarylene comprise two or more rings, two or more rings may be fused together.

In the specification, C ₆ -C ₆₀ aryloxy refers to -OA ₁₀₂ (wherein A ₁₀₂ is the C ₆ -C ₆₀ aryl), and the C ₆ -C ₆₀ arylthio refers to -SA ₁₀₃ , And A ₁₀₃ is the above C ₆ -C ₆₀ aryl group.

In the present specification, a monovalent non-aromatic condensed polycyclic group is a monovalent aromatic condensed polycyclic group in which two or more rings are condensed with each other and contain only carbon as a ring-forming atom and the whole molecule is non-aromatic. &Lt; / RTI &gt; Examples of the monovalent non-aromatic condensed polycyclic group include fluorenyl and the like. In the present specification, the divalent non-aromatic condensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

In the present specification, a monovalent non-aromatic condensed heteropolycyclic group is a monovalent aromatic condensed heteropolycyclic group in which two or more rings are condensed with each other and contain heteroatoms selected from N, O, P and S in addition to carbon as a ring- , And mono-valent groups in which the whole molecule has non-aromacity. The monovalent non-aromatic heterocyclic polycyclic group includes carbazolyl and the like. In the present specification, the divalent non-aromatic heterocyclic polycyclic group means a divalent group having the same structure as the monovalent non-aromatic heterocyclic polycyclic group.

In the present specification, "Ph" means phenyl, "Me" means methyl, "Et" means ethyl, and "ter-Bu" or "But" means tert-butyl.

Hereinafter, the organic light-emitting device according to one embodiment of the present invention will be described in more detail with reference to synthesis examples and examples. In the following Synthesis Examples, the molar equivalent of A and the molar equivalent of B in the expression &quot; B was used instead of A &quot;

Example  One

An ITO glass substrate (manufactured by Corning) having an ITO layer of 15 Ω / cm ² (1200 Å) formed was cut into a size of 50 mm × 50 mm × 0.7 mm and ultrasonically cleaned using isopropyl alcohol and purified water for 5 minutes each , The substrate was irradiated with ultraviolet rays for 30 minutes, exposed to ozone to be cleaned, and the ITO glass substrate was placed in a vacuum deposition apparatus.

M-MTDATA was deposited on the ITO anode to form a hole injection layer having a thickness of 600 Å. HT 5 was deposited on the hole injection layer to form a hole transport layer having a thickness of 200 Å. Then, compound 1 was deposited on the hole transport layer To form a 100 Å thick auxiliary layer. ADN (host) and FD1 (dopant) were co-deposited on the auxiliary layer above the light emitting layer at a weight ratio of 95: 5 to form a 200 Å thick light emitting layer.

An electron injection layer having a thickness of 10 Å was formed by depositing LiF on the electron transport layer to form an electron transport layer having a thickness of 300 Å. Then, Al was deposited on the electron injection layer to form a 1000 Å thick Thereby forming an organic light emitting device.

Example  2

An organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 4 was used instead of Compound 1 in forming the auxiliary layer.

Example  3

An organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 5 was used instead of Compound 1 in forming the auxiliary layer.

Example  4

An organic light emitting device was fabricated using the same method as in Example 1 except that Compound 12 was used instead of Compound 1 in forming the auxiliary layer.

Comparative Example  One

An organic light emitting device was fabricated in the same manner as in Example 1 except that NPB was used instead of Compound Compound 1 in forming the auxiliary layer.

Comparative Example  2

An organic light emitting device was fabricated using the same method as in Example 1 except that Compound A was used in place of Compound Compound 1 in forming the auxiliary layer.

<Compound A>

Evaluation example

The lifetime (at a current density of 1000 nit) of each of the organic light emitting devices of Examples 1 to 4 and Comparative Examples 1 and 2 was evaluated using a PR650 Spectroscan Source Measurement Unit (manufactured by PhotoResearch). The results are shown in Table 1 below.

Auxiliary layer material Driving voltage [V] Efficiency [cd / A] life span Example 1 Compound 1 4.1 1.2 1.2 Example 2 Compound 4 4.0 1.3 1.3 Example 3 Compound 5 4.08 1.2 1.2 Example 4 Compound 12 4.0 1.1 1.3 Comparative Example 1 NPB 4.05 0.9 0.8 Comparative Example 2 Compound A 4.2 1.1 0.9

According to Table 1, the organic light emitting device of Example 1 showed better efficiency and injection characteristics than the organic light emitting devices of Comparative Examples 1 and 2.

10, 20: Organic light emitting device
110, 210: a first electrode
130, 230: hole transport region
140, 240: auxiliary layer
150, 250: organic layer
160, 260: light emitting layer
180, 280: electron transport region
190, 290: second electrode

Claims (20)

A first electrode; A second electrode; A light emitting layer interposed between the first electrode and the second electrode; And
And a hole transporting region interposed between the first electrode and the light emitting layer,
Wherein the hole transporting region comprises an auxiliary layer and the auxiliary layer comprises an amine compound represented by the following Formula 1:
&Lt; Formula 1 >

&Lt; Formula 2-1 >< Formula 2-2 >< Formula 2-3 &

Among the above-mentioned formulas (1) and (2-1) to (2-3)
L ₁₁ is a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene, a substituted or unsubstituted Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene, substituted or unsubstituted C ₆ -C ₆₀ arylene, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic a diabalent non-aromatic condensed polycycle and a substituted or unsubstituted divalent non-aromatic condensed heteropolycycle;
a11 is selected from 0, 1, 2, 3, 4, 5 and 6;
R ₁₁ and R ₁₂ are, independently of each other, a substituted or unsubstituted C ₁ -C ₆₀ alkyl, substituted or unsubstituted C ₆ -C ₆₀ aryl, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl, A substituted monovalent non-aromatic condensed polycyclic and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic ring, with the proviso that substituted or unsubstituted dibenzofuranyl is excluded;
R ₁₃ is selected from the groups represented by the above formulas (2-1) to (2-3);
R ₂₁ to R ₂₇ are each independently of the other hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and its salts, Substituted or unsubstituted C ₁ -C ₆₀ alkyl, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl, substituted or unsubstituted C ₆ -C ₆₀ aryl, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl, Substituted or unsubstituted monovalent non-aromatic condensed polycyclic, substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic and -N (Q ₁ ) (Q ₂ );
b22 and b24 are independently selected from 1, 2, 3 and 4;
b23 and 27 are independently of each other selected from 1, 2 and 3;
The substituted C ₃ -C ₁₀ cycloalkylene, substituted C ₁ -C ₁₀ hetero cycloalkylene, substituted C ₃ -C ₁₀ cycloalkyl alkenylene, substituted C ₁ -C ₁₀ heterocycloalkyl alkenylene, substituted C ₆ -C ₆₀ arylene, substituted C ₁ -C ₆₀ heteroarylene, substituted divalent non-aromatic fused polycyclic, unsubstituted bivalent aromatic condensed polycyclic heteroaryl, a C ₁ -C ₆₀ alkyl, substituted At least one of C ₃ -C ₁₀ cycloalkyl, substituted C ₆ -C ₆₀ aryl, substituted C ₁ -C ₆₀ heteroaryl, substituted monovalent non-aromatic condensed polycyclic and substituted monovalent non-aromatic heterocyclic polycyclic &Lt; / RTI &gt;
C ₁ -C ₆ alkyl, C ₂ -C ₆ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acids and salts thereof, ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl and C ₁ -C ₆₀ alkoxy;
Deuterium, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazines, hydrazones, carboxyl and salts thereof, acid and salts thereof, phosphoric acid and salts thereof, C ₃ -C ₁₀ cycloalkyl, C ₃ - C ₃ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio (arylthio), C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic one and is a non-alkenyl aromatic hydrocarbon ring condensed with at least one of the polycyclic substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ al, C ₂ -C ₆₀ alkynyl and C ₁ -C ₆₀ alkoxy;
C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy , C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic heterocyclic polycyclic;
C ₁ -C ₆ alkyl, C ₂ -C ₆ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acids and salts thereof, ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₁ -C ₆₀ alkoxy, C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ hetero cycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic one and is a non-aromatic heterocyclic at least one of the substituted condensed polycyclic, C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heteroaryl cycloalkenyl, C ₆ -C ₆₀ aryl , C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic heterocyclic polycyclic; And
Selected from _{-N (Q 11) (Q 12} ) and;
Q ₁ , Q ₂ , Q ₁₁ and Q ₁₂ are independently from each other selected from hydrogen, deuterium, C ₁ -C ₆₀ alkyl and C ₆ -C ₆₀ aryl;
* Is a nitrogen atom of formula (1) or a binding site with L &lt; ₁₁ &gt;. The method according to claim 1,
In the above formula (1), L ₁₁ represents
And examples thereof include phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthylene, acenaphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluoranenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoro But are not limited to, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, But are not limited to, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, coronenylene, ovalenylene, pyrrolylene, thiophenyl Thiophenylene, furanylene, imida The present invention relates to a process for producing a polyol (hereinafter referred to as &quot; polyol &quot;), a polyol, a polyol, a polyol, a polyol, a polyol, a polyol, a polyol, pyrazinylene, pyrimidinylene, pyridazinylene, isoindolylene, indolylene, indazolylene, purinylene, quinolinylene, quinolinylene, , Isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cyinolinylene, the present invention relates to a process for producing a cinnolinyl derivative of the general formula (1), wherein the cinnolinylene, carbazolylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzoimidazolylene, (benzofuranylene), There may be mentioned benzothiophenylene, isobenzothiazolylene, benzooxazolylene, isobenzooxazolylene, triazolylene, tetrazolylene, oxadiazole, Examples of the dibenzothiophenylene derivatives include oxadiazolylene, triazinylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, and imidazopyridyl. Nylene; And
C ₁ -C ₂₀ alkyl, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkoxy, halogen, halogen, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxyl and salts thereof, sulfonic acid and its salts, ₂₀ alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pental alkylenyl, indenyl, naphthyl, azulenyl, heptal alkylenyl, indazol hexenyl, acetoxy-naphthyl, fluorenyl, spy Fluorenyl, triphenylenyl, pyrenyl, crycenyl, naphthacenyl, picenyl, perylenyl, phenanthryl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, , Pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrroyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl , Pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, inda Wherein R is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, alkynyl, alkynyl, alkynyl, alkynyl, alkynyl, alkynyl, alkynyl, alkynyl, Benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzothiophene, benzothiophenyl, Phenyl, phenanthrenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene substituted with at least one of phenyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl and imidazopyridinyl , Acenaphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylenylene, pie Rhenylene, klychenylene, naphthacenylene, pichenylene , Pyrenylenylene, pentaphenylene, hexacenylene, pentacenylene, rubisenylene, coronenylene, ovalenylene, pyrrolylene, thiophenylene, furanylene, imidazolyl, pyrazolylene, thiazolylene , Isothiazolylene, oxazolylene, isoxazolylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazienylene, isoindolylene, indoleylene, indazolylene, purinylene, quinolinylene, iso And examples thereof include quinolinylene, benzoquinolinylene, phthalazienylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cyanolylene, carbazolylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene , Benzoimidazolylene, benzofuranylene, benzothiophenylene, isobenzothiazolylene, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, di Benzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocaine, Sol ylene, thiadiazol-ylene and already jopi piperidinyl alkenylene; &Lt; / RTI &gt; The method according to claim 1,
In the above formula (1), L ₁₁ represents
Phenylene, naphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, triphenylenylene, pyrenylene and chlorenylene; And
Phenyl, naphthyl, fluorenyl, spiro-fluorenylene, benzofluorenylene, substituted phenyl, naphthyl, fluorenyl, pyridinyl, pyrazinyl, pyrimidinyl, thiophenyl and furanyl substituted with at least one of , Dibenzofluorenylene, phenanthrenylene, anthracenylene, triphenylrenylene, pyrenylene and chrysinylene; &Lt; / RTI &gt; The method according to claim 1,
Wherein L ₁₁ is a group selected from the following formulas (3-1) to (3-8):

Among the above-mentioned formulas (3-1) to (3-8)
Z ₁ and Z ₂ are each independently selected from a hydrogen atom, phenyl, naphthyl, fluorenyl, pyridinyl, pyrazinyl, pyrimidinyl, thiophenyl and furanyl,
d1 is selected from integers from 1 to 4;
d2 is selected from integers from 1 to 3;
d3 is selected from integers from 1 to 6;
d4 is selected from integers from 1 to 8;
d6 is selected from integers from 1 to 5;
* And * are binding sites with neighboring atoms. The method according to claim 1,
Wherein L &lt; ₁₁ &gt; is a group selected from the following formulas (4-1) to (4-8)

In the above formulas 4-1 to 4-8
* And * are binding sites with neighboring atoms. The method according to claim 1,
In the general formula (1), a11 is an integer of 0, 1 or 2. The method according to claim 1,
Wherein R ₁₁ and R ₁₂ are, independently of each other,
But are not limited to, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, But are not limited to, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, But are not limited to, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, But are not limited to, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, Pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyridyl, pyrimidinyl, Pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, pyrimidinyl, , Isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, ), Carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzofuranyl, Benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triaryl, triazolyl, Triazinyl, dibenzothiophenyl, benzocarbazolyl, dibenzo &lt; RTI ID = 0.0 &gt; Bar jolil, thiadiazole and imidazole jolil jopi piperidinyl; And
Heavy hydrogen, 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 salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl Im import and C ₂ -C ₆₀ heteroaryl group, at least one substituted phenyl selected from the group consisting of , Phenalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenan Thienyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, klycenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, , Pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrroyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl Pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl Benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, , Triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl and imidazopyridinyl; &Lt; / RTI &gt; The method according to claim 1,
Wherein R ₁₁ and R ₁₂ are, independently of each other,
Phenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, triphenylenyl, pyrenyl, klycenyl, pyridinyl, pyrimidinyl Thiophenyl, furanyl, carbazolyl, benzofuranyl, benzothiophenyl, dibenzothiophenyl, benzocarbazolyl, benzothiophenyl, benzothiophenyl, benzothiophenyl, benzoxazolyl, And dibenzocarbazolyl; And
Wherein the substituent is selected from the group consisting of hydrogen, deuterium, halogen atom, cyano group, nitro group, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, triphenylenyl, pyrenyl, pyridinyl, Phenyl, naphthyl, fluorenyl, spiro-fluorenylsubstituted by at least one of the following: halogen, cyano, cyano, , Benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, triphenylenyl, pyrenyl, klycenyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, naphthyridyl Neu, quinoxalinyl, quinazolinyl, thiophenyl, furanyl, carbazolyl, benzofuranyl, benzothiophenyl, dibenzothiophenyl, benzocarbazolyl and dibenzocarbazolyl; &Lt; / RTI &gt; The method according to claim 1,
Wherein R ₁₁ and R ₁₂ are, independently of each other,
Phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, triphenylenyl, pyrenyl, crycenyl, carbazolyl, benzocarbazolyl and dibenzocarbazolyl; And
Naphthyl, fluorenyl, phenanthrenyl, anthracenyl, phenanthrenyl, and the like substituted with at least one of a halogen atom, a halogen atom, a cyano group, a nitro group, phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, Triphenylenyl, pyrenyl, crycyenyl, carbazolyl, benzocarbazolyl and dibenzocarbazolyl; &Lt; / RTI &gt; The method according to claim 1,
Wherein R ₁₁ and R ₁₂ are each independently a group selected from the following formulas (5-1) to (5-23):

Of the above-mentioned formulas (5-1) to (5-23)
* Is the binding site with neighboring atoms. The method according to claim 1,
Wherein R < ₁₃ > is selected from the group consisting of the following Chemical Formulas 2-1a, 2-2a, 2-2b and 2-3a:
&Lt; Formula 2-1a &

<Formula 2-2a>

(2-2b)

<Formula 2-3a>

Of the 2-1a, 2-2a, 2-2b and 2-3a,
R ₂₁ to R ₂₇ and b ₂₂ to b ₂₇ are as defined in claim 1. The method according to claim 1,
Wherein R < ₁₃ > is selected from the group consisting of the following Chemical Formulas 2-1a, 2-2a, 2-2b and 2-3a:
&Lt; Formula 2-1a &

<Formula 2-2a>

(2-2b)

<Formula 2-3a>

Of the 2-1a, 2-2a, 2-2b and 2-3a,
R ₂₁ to R ₂₇ independently represent hydrogen, deuterium, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, But are not limited to, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, (S) selected from spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, Pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, naphthacenyl, naphthacenyl, But are not limited to, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, Isomers of pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isooxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, And examples thereof include pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolyl, Benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl (such as benzoquinolinyl, phthalazinyl, naphthyridinyl, quinazolinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, ), Tetrazolyl, oxadiazolyl, triazinyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl, and -N (Q ₁ ) (Q ₂ ); And
Heavy hydrogen, 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 salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl Im import and C ₂ -C ₆₀ heteroaryl groups substituted with at least one selected from the group consisting of methyl Butyl, isobutyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, Thienyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrene, fluorenyl, Naphthyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, , Thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl , Benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzo Benzothiophenyl, benzothiazolyl, benzooxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazole Zolyl and imidazopyridinyl; ;
Q ₁ and Q ₂ are each independently selected from C ₆ -C ₆₀ aryl;
b22 and b24 are independently selected from 1, 2, 3 and 4;
b23 is selected from 1, 2, and 3. The method according to claim 1,
Wherein R < ₁₃ > is selected from the group consisting of the following Chemical Formulas 2-1a, 2-2a, 2-2b and 2-3a:
&Lt; Formula 2-1a &

<Formula 2-2a>

(2-2b)

Of the above-mentioned formulas (2-1a), (2-2a), (2-2b) and (2-3a)
R ₂₁ to R ₂₄ independently represent hydrogen, deuterium, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec- Ph) ₂ ;
b22 and b24 are independently selected from 1, 2, 3 and 4;
b23 is selected from 1, 2, and 3. The method according to claim 1,
Wherein the amine compound is represented by any one of the following Chemical Formulas 1A to 1D:
&Lt;

&Lt; Formula 1B &gt;

&Lt; Formula 1C &gt;

&Lt; Formula 1D &gt;

Among the above general formulas (1A) to (1D)
L ₁₁ , a11, R ₁₁ , R ₁₂ , R ₂₁ to R ₂₇ and b ₂₂ to b ₂₇ are as defined in claim 1. 15. The method of claim 14,
L ₁₁ is a group selected from the following formulas (4-1) to (4-8);
a11 is an integer of 0, 1 or 2;

Among the above-mentioned formulas (4-1) to (4-8)
* And * are binding sites with neighboring atoms. 15. The method of claim 14,
R ₁₁ and R ₁₂ independently represent a group selected from the following formulas (5-1) to (5-23):

Of the above formulas (5-1) to (5-22)
* Is the binding site with neighboring atoms. 15. The method of claim 14,
R ₂₁ to R ₂₄ independently represent hydrogen, deuterium, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec- Ph) ₂ ;
b22 and b24 are independently selected from 1, 2, 3 and 4;
and b23 is selected from 1, 2, and 3. The method according to claim 1,
Wherein the amine compound is selected from the following compounds 1 to 12:

The method according to claim 1,
Wherein the light emitting layer and the auxiliary layer are disposed in contact with each other. The method according to claim 1,
Wherein the thickness of the auxiliary layer is in the range of 10 to 1000 ANGSTROM.

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