KR20150143280A - Organic light- emitting device - Google Patents

Abstract

Disclosed is an organic light-emitting device having improved efficiency, which comprises: a first electrode; a second electrode facing the first electrode; a light emitting layer interposed between the first electrode and the second electrode; and an electron transporting region interposed between the light emitting layer and the second electrode.

Description

[0001] The present invention relates to an organic light-

And 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.

An embodiment of the present invention provides an organic light emitting device.

One embodiment of the present invention is a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And an organic layer including a light emitting layer interposed between the first electrode and the second electrode;

An electron transporting region interposed between the light emitting layer and the second electrode;

Wherein the electron transporting region comprises an electron transporting material represented by the following Formula 1:

≪ Formula 1 >

In Formula 1,

L ₁ to L ₃ independently represent a substituted or unsubstituted C ₂ -C ₁₀ alkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl A substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ arylene group, a C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted 2 non-aromatic condensed polycyclic group, and a substituted or unsubstituted 2 non-aromatic heterocyclic is selected from the condensed polycyclic groups;

a1 to a3 are independently selected from 0, 1, 2 and 3;

R ₁ to R ₃ independently represent a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, A substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ hetero Cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted 1 is selected from non-aromatic heterocyclic polycyclic groups;

R ₄ and R ₅ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl, a cyano, a nitro, an amino, an amidino, a hydrazine, a hydrazone, acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C _A substituted or unsubstituted C ₁ -C ₆ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C _A substituted or unsubstituted C ₁ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic Sum polycyclic group, and a substituted or unsubstituted 1, a non-aromatic heterocyclic is selected from a condensed polycyclic group;

n1 and n2 are independently selected from 0, 1, 2, 3 and 4;

The substituted C ₂ -C ₁₀ alkylene group, the substituted C ₃ -C ₁₀ cycloalkylene group, the substituted C ₁ -C ₁₀ heterocycloalkylene group, the substituted C ₃ -C ₁₀ cycloalkenylene group, the substituted C ₁ -C ₁₀ cycloalkenylene group, -C ₁₀ heterocycloalkyl alkenylene group, substituted C ₆ -C ₆₀ aryl group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted divalent non-aromatic condensed polycyclic group, a substituted divalent non-aromatic hydrocarbon ring condensed A substituted C ₁ -C ₆₀ alkyl group, a substituted C ₂ -C ₆₀ alkenyl group, a substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cyclo alkyl, substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted a non-aromatic condensed polycyclic groups, and substituted monovalent non-aromatic heterocyclic fused polycyclic Group At least one of the ventilation,

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -N (Q _{11) (Q 12), -Si (Q} 13) (Q 14) (Q 15) and _{-B (Q 16) (Q 17} ) of the at least one substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl , A C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

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 aryl A C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group;

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocyclo alkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ - C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 21) (Q} 22), -Si (Q 23) (Q 24) (Q 25) and _{-B (Q 26) (Q 27} ) of the at least one substituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkyl alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ H. Heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic heterocyclic polycyclic group; And

_{-N (Q 31) (Q 32} ), -Si (Q 33) (Q 34) (Q 35) and _{-B (Q 36) (Q 37} ); ;

Q ₁₁ to Q _17, Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are, each independently, hydrogen, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, C ₁ to each other - C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic heterocyclic is selected from a condensed polycyclic group, aromatic condensed polycyclic group, and 1 is non.

The organic light emitting device according to embodiments of the present invention can have a low driving voltage, high efficiency, high brightness, and long life.

1 is a schematic view illustrating a structure of an organic light emitting diode according to an embodiment of the present invention.
2 is a diagram showing the result of thermogravimetric analysis (TGA) of Compound 5. Fig.
Fig. 3 is a diagram showing the results of differential thermal calorimetry (DSC) of Compound 5. Fig.
4 is a diagram showing UV absorption and PL spectral results of Compound 5. Fig.
5 is a diagram showing a cyclic voltammetry result of Compound 5. FIG.

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, "(organic layer) includes a compound represented by the general formula (1)" means that one kind of compound (organic layer) belongs to the category of the above formula 1 or two or more different compounds Quot; can be interpreted as "

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.

1 schematically shows a cross-sectional view of an organic light emitting device 10 according to an embodiment of the present invention. The organic light emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.

Hereinafter, a structure and a manufacturing method of an organic light emitting diode according to an embodiment of the present invention will be described with reference to FIG.

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.

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

The hole transporting region may include at least one of a hole injecting layer (HIL), a hole transporting layer (HTL), a buffer layer and an electron blocking layer (EBL), and the electron transporting region may include at least one of a hole blocking layer (HBL) (ETL), and an electron injection layer (EIL).

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 single layer structure composed of a plurality of different materials, or may have a structure in which a hole injection layer / hole transport layer, a hole injection layer / a hole transport layer / a buffer layer , A hole injection layer / a buffer layer, a hole transporting layer / a buffer layer, a hole injecting layer / a hole transporting layer / an electron blocking layer, 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.

Wherein the hole transporting region is selected from the group consisting of m-MTDATA, TDATA, 2-TNATA, NPB, beta-NPB, TPD, Spiro- TPD, Spiro- NPB, methylated- 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) (Polyaniline) / poly (4-styrenesulfonate)), tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetra A quinone derivative such as fluoro-tetracyano-1,4-benzoquinone dimethine (F4-TCNQ), at least one of the following compound HT-D1, a compound represented by the following formula 201 and a compound represented by the following formula May include:

<Compound HT-D1> <F4-TCNQ>

&Lt; Formula 201 >

&Lt; EMI ID =

Of the above formulas (201) and (202)

The description of L ₂₀₁ to L ₂₀₅ is independent of each other, see description 7 of L ₁ in this 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 ₁ in the present specification.

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

L ₂₀₁ to L ₂₀₅ independently from each other,

A phenylene group, a phenanthrene group, an anthracenylene group, a pyrenylene group, a chrysenylene group, a pyridinyl group, a pyrenyl group, a pyrenyl group, A phenylene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, And

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, Naphthylenylene group, fluorenylene group, spiro-fluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, phenanthrenylene group, and phenanthrenylene group which are substituted with at least one of a hydrogen atom, Anthracenylene group, pyrenylene group, klychenylene group, pyridinylene , A pyrazinyl group, a pyrimidinyl group, a group pyridazinyl, quinolinyl group, isoquinolinyl group, quinoxalinyl carbonyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group; ;

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 represent a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, A cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, And

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A halogen atom, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an azulenyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, Anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyranyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazole A phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, A pyridinyl group, a pyrazinyl group, a pyrimidinyl group, Florida possess group, a quinolinyl group, an isoquinolinium group, a quinoxalinyl group, a quinazolinyl group, a carbazole group and a triazole group possess; , 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 the same as that described in this specification, and R ₂₁₁ and R ₂₁₂ are the same as R ₂₀₃ R ₂₁₃ to R ₂₁₆ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, jongi, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group 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 _A C ₁ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkenyl group, a C ₆ -C ₆₀ aryl group, a C ₆ -C ₆₀ arylox A C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocyclic polycyclic group; &Lt; / RTI &gt;

For example, In the formula, 201A, 201A-1 and 202A, L ₂₀₁ to L ₂₀₃ are independently of each other, a phenyl group, a naphthyl alkylenyl group, a fluorenyl group, a spy-fluorenyl group, a benzo fluorenyl A phenanthrenylene group, a phenanthrene group, a pyrenylene group, a chryshenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an iso Quinolinylene group, quinoxalinylene group, quinazolinylene group, carbazolylene group and triazylene group; And

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, A pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group such as a pyranyl group, a pyranyl group, a pyrenyl group, A phenylene group, a phenanthrenylene group, an anthracenylene group, a phenanthrenylene group, an anthracenylene group, a naphthylene group, , Pyrenylene group, chryshenylene group, pyridinylene , A pyrazinyl group, a pyrimidinyl group, a group pyridazinyl, quinolinyl group, isoquinolinyl group, quinoxalinyl carbonyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group; ;

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

R ₂₀₃ , R ₂₁₁ and R ₂₁₂ independently represent a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, A pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group; And

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, A pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group such as a pyranyl group, a pyranyl group, a pyrenyl group, A phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klycenyl group , A pyridinyl group, a pyrazinyl group, a pyrimidinyl group, Florida possess group, a quinolinyl group, an isoquinolinium group, a quinoxalinyl group, a quinazolinyl group, a carbazole group and a triazole group possess; ;

R ₂₁₃ and R ₂₁₄ independently represent a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, An anthracenyl group, a pyrenyl group, a klychenyl group, a pyridinyl group, a pyridinyl group, a pyranyl group, a pyranyl group, a pyranyl group, a pyranyl group, A C ₁ -C ₂₀ alkyl group substituted with at least one member selected from the group consisting of a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group, A C ₁ -C ₂₀ alkoxy group;

A phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klychenyl group, a pyridinyl group, , A pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group; And

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, A pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group such as a pyranyl group, a pyranyl group, a pyrenyl group, A phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klycenyl group , A pyridinyl group, a pyrazinyl group, a pyrimidinyl group, Florida possess group, a quinolinyl group, an isoquinolinium group, a quinoxalinyl group, a quinazolinyl group, a carbazole group and a triazole group possess; ;

R ₂₁₅ and R ₂₁₆ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, A sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof,

A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, An anthracenyl group, a pyrenyl group, a klychenyl group, a pyridinyl group, a pyridinyl group, a pyranyl group, a pyranyl group, a pyranyl group, a pyranyl group, A C ₁ -C ₂₀ alkyl group substituted with at least one member selected from the group consisting of a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group, A C ₁ -C ₂₀ alkoxy group;

A phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klychenyl group, a pyridinyl group, , A pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group and a triazinyl group; And

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, A pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group such as a pyranyl group, a pyranyl group, a pyrenyl group, A phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klycenyl group , A pyridinyl group, a pyrazinyl group, a pyrimidinyl group, Florida possess group, a quinolinyl group, an isoquinolinium group, a quinoxaline group salicylate group, a quinazolinyl group and a 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 compound HT-D1, but the present invention is not limited thereto.

The hole transporting region may further include at least one of a buffer layer and an electron blocking layer in addition to the hole injecting layer and the hole transporting layer as described above. The buffer layer may compensate the optical resonance distance according to the wavelength of the light emitted from the light emitting layer to increase the light emission efficiency. As the material contained in the buffer layer, a material that can be included in the hole transporting region may be used. The electron blocking layer is a layer that prevents the injection of electrons from the electron transporting region.

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.

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

The host may comprise at least one of the following TPBi, TBADN, ADN (also referred to as "DNA "), 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; / RTI _{&gt; 301} may be selected from the group consisting of naphthalene, heptalene, fluorenene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene ), Fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, And indenoanthracene;

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocyclo alkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ - C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic group and the condensed polycyclic _{-Si (Q 301) (Q 302} ) (Q 303) ( Q ₃₀₁ to Q ₃₀₃ are the independently from each other , Naphthalene, heptarene, flu, substituted with at least one selected from hydrogen, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₆ -C ₆₀ aryl group and a C ₁ -C ₆₀ heteroaryl group. Ore, spiro-fluorene, Division fluorene, dibenzo fluorene, page nalren, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, Cry Sen, naphthacene, pisen, perylene, penta pen and indeno anthracene; ;

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

R ₃₀₁ is

A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, , group possess is, pyrimidinyl group, pyridyl group pyrazinyl, quinolinyl group, an isoquinolinium group, a quinoxalinyl group, a quinazolinyl group, a carbazole group and a triazinyl group optionally substituted with at least one selected from, C ₁ -C ₂₀ An alkyl group and a C ₁ -C ₂₀ alkoxy group;

A phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klychenyl group, a pyridinyl group, , A pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazole group and a triazinyl group; And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a salt thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spy-fluorenyl group, a fluorenyl group benzo, dibenzo-fluorenyl group, a phenanthrenyl group, A pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a carbazolyl group, and an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, A phenanthrenyl group, an anthracenyl group, a pyrenyl group, a pyrenyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, A benzyl group, a benzyl group, a benzyl group, a benzyl group, A pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazole group and a triazinyl group; ;

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 ,

A phenylene group, a phenanthrene group, an anthracenylene group, a pyrenylene group and a chrysene ring group; a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a salt thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spy-fluorenyl group, a fluorenyl group benzo, dibenzo-fluorenyl group, a phenanthrenyl group, Naphthylene group, fluorenylene group, spiro-fluorenrenylene group, benzofluorenylene group, dibenzofluorenylenylene group, dibenzofluorenylene group, and dibenzofluorenylene group which are substituted with at least one selected from anthracenyl, pyrenyl and klycenyl, , Phenanthrenylene group, anthracenylene group, pyrenylene group and chrysenylene group; ;

R ₃₀₁ is

A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, At least one selected from the group consisting of a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a klycenyl group A substituted C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

A phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group and a klycenyl group; And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a salt thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spy-fluorenyl group, a fluorenyl group benzo, dibenzo-fluorenyl group, a phenanthrenyl group, A phenanthryl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, A cenyl group, a pyrenyl group and a crycenyl group; , 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 further 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 represent a nitrogen atom or a carbon atom;

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,

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, salt, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group (aryloxy) group, a C ₆ -C ₆₀ arylthio (arylthio) group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -N _{(Q 401) (Q 402)} , -Si (Q 403) (Q 404) (Q 405) and -B (Q ₄₀₆₎ at least one substituted, C ₁ -C ₆₀ alkyl group of the (Q _407), C ₂ - A C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, and a C ₁ -C ₆₀ alkoxy group;

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 aryl A C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group;

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A C ₁ -C ₆ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 411) (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 group, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group , C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ Interrogating an aryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic group, fused polycyclic; 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;

Q ₄₀₁ to Q ₄₀₇ , Q ₄₁₁ to Q ₄₁₇ and Q ₄₂₁ to Q ₄₂₇ are independently of each other, hydrogen, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₆ -C ₆₀ aryl group And a C ₁ -C ₆₀ heteroaryl group;

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-C₅알킬렌기, C₂-C₅알케닐렌기, -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 may be, for 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 group, C ₂ -C ₅ alkenylene, -N (R ') - (wherein, R' - can be connected across a) is C ₁ -C ₁₀ alkyl or C ₆ -C ₂₀ aryl group), or -C (= O) have.

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 is a naphthalene, heptalene, fluorenene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene ), Fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, And indenoanthracene;

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A C ₁ -C ₆ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic group and the condensed polycyclic _{-Si (Q 501) (Q 502} ) (Q 503) ( Q ₅₀₁ to Q ₅₀₃ are the independently from each other, hydrogen , A C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₆ -C ₆₀ aryl group and a C ₁ -C ₆₀ heteroaryl group), naphthalene, heptalene, fluorene, Spiro-fluorene, Ben Fluorene, dibenzo fluorene, page nalren, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, Cry Sen, naphthacene, 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 represent a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, A benzyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, A dibenzothiophenyl group; And

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, A pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, a pyrazinyl group, a pyrazinyl group, a pyridinyl group, A phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthryl group, A cyanyl group, a pyrenyl group, a klycenyl group, Group, a group possess is, pyrimidinyl group, pyridyl group pyrazinyl, quinolinyl group, an isoquinolinium group, a quinoxalinyl group, a quinazolinyl group, a carbazole group, a triazinyl group, a dibenzo furanoid group and dibenzo-thio group; ;

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

xd4 is selected from 1, 2, 3 and 4.

The fluorescent host may comprise at least one of the following compounds FD1 to FD9:

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 may be disposed above the light emitting layer.

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

The electron transporting region may include an electron transporting material represented by the following general formula (1). For example, the electron transporting material represented by Formula 1 may be included in the electron transporting layer of the electron transporting region:

&Lt; Formula 1 >

In Formula 1, L ₁ to L ₃ independently represent a substituted or unsubstituted C ₂ -C ₁₀ alkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ alkylene group, C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl alkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ arylene group, , A substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic group.

For example, in the above formula (1), L ₁ to L ₃ are, independently of each other,

A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, An acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrene group, A phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenyl group, A naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubidecylene group, rubicenylene group, coronenylene group, ovalenylene group, pyrrolylene group, An isothiazolylene group, a thiophenylene group, a furanylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, An oxazolylene group, an isooxazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an iso An isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a carbazolylene group, carbazolylene group, phenanthridinylene group, acridinyl group, ene group, a phenanthrolinylene group, a phenazinylene group, a benzoimidazolylene group, a benzofuranylene group, a benzothiophenylene group, a benzothiazolylene group, an isobenzothiazolylene group, an isobenzooxazolylene group, an isobenzooxazolylene group, a triazolylene group, a tetrazolylene group, an isobenzothiazolyl group, an isobenzothiazolyl group, An oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group and a dibenzocarbazolylene group; And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenyl group, Anthracenyl group, anthracenyl group, phenanthrenyl group, phenanthrenyl group, phenanthrenyl group, phenanthryl group, phenanthryl group, phenanthryl group, A fluorenyl group, a fluorenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, , An ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, A pyridinyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an imidazolyl group, an imidazolyl group, A phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, A benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, A phenylene group, a pentalenylene group, an indenylene group, a naphthyl group which is substituted with at least one of a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group and an imidazopyridinyl group, Azulenylene group, heptalenyl group A phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a phenanthrenylene group, an anthracenylene group, a phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, And examples thereof include a fluorenylene group, a fluorenylene group, a fluorenylene group, a fluorenylene group, a fluorenylene group, a fluorenylene group, a fluorenylene group, a fluorenenylene group, a triphenylenylene group, a pyrenylene group, a chryshenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, A thiophenylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a pyridinylene group, An isoindolylene group, an indolylene group, an indazolylene group, a prolinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthaloylphenylene group, a phenanthrene group, Naphthylidene group, quinoxalinylene group, , A quinazolinyl group, a quinazolinyl group, a quinazolinyl group, a cyclopentadienyl group, a benzothiophenylene group, a benzothiophenylene group, a benzothiophenylene group, a benzothiophenylene group, Benzothiophenylene group, dibenzothiophenylene group, dibenzothiophenylene group, dibenzothiophenylene group, dibenzothiophenylene group, dibenzothiophenylene group, dibenzothiophenylene group, dibenzothiophenylene group, dibenzothiophenylene group, dibenzothiophenylene group, dibenzothiophenylene group , Benzocarbazolylene group and dibenzocarbazolylene group; , But is not limited thereto.

As another example, in the above formula (1), L ₁ to L ₃ are, independently of each other,

A phenylene group, a phenanthrene group, a phenanthrenylene group, a pyrenylene group, a chrysenylene group, a pyrrolylene group, a thiophenylene group, a furanylene group, an imidazolylene group, , A pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an indolylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a naphthyridinylene group, a quinoxalinylene group, A benzothiophenylene group, a triazolylene group, a tetrazolenylene group, a tetrazolene group, a tetrazolene group, a tetrazolyl group, a tetrazolyl group, a tetrazolyl group, a quinazolinyl group, Trialkynylene groups, dibenzofuranylene groups and dibenzothiophenylene groups; And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, A thiazolyl group, a thiazolyl group, a pyrazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, An isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, , A benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, A thiazolyl group, an oxadiazolyl group, a triazinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoxazolyl group, , A dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group, each of which is substituted with at least one of a phenylene group, a naphthylene group, a fluorenylene group, a phenanthrenylene group, an anthracenylene group, A thiophenylene group, a furanyl group, an imidazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an indolylene group, a pyridazinyl group, a pyrazolyl group, A thiophenylene group, a quinolinylene group, an isoquinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a sinolinylene group, , Phenanthrolylene group, benz Benzimidazolylenes, benzopyranylene groups, benzothiophenylene groups, triazolylene groups, tetrazolylene groups, triazienylene groups, dibenzofuranylene groups and dibenzothiophenylene groups; , But is not limited thereto.

As another example, L ₁ to L ₃ in the above formula (1) may be independently represented by any one of the following formulas (3-1) to (3-30), but is not limited thereto:

Among the above-mentioned formulas (3-1) to (3-31)

Y ₃₁ is selected from C (R ₃₃ ) (R ₃₄ ), N (R ₃₃ ), O and S;

R ₃₁ to R ₃₄ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, A sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spioro-fluorenyl group, Anthracenyl group, pyranyl group, pyridinyl group, pyridinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinolyl group, A thiazolyl group, a salinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group;

a31 is selected from 1, 2, 3 and 4;

a32 is selected from 1, 2, 3, 4, 5 and 6;

a33 is selected from 1, 2, 3, 4, 5, 6, 7 and 8;

a34 is selected from 1, 2, 3, 4 and 5;

a35 is selected from 1, 2 and 3;

* And * are independent sites of bonding to neighboring atoms.

As another example, in the above formula (1), L ₁ to L ₃ may be independently represented by any one of the following formulas (4-1) to (4-56), but are not limited thereto:

Of the above-mentioned formulas (4-1) to (4-56)

* And * are independent sites of bonding to neighboring atoms.

In the formula 1, a1 refers to the number of L _1, and 0, and can be selected from 1, 2 and 3. For example, in Formula 1, a1 may be selected from 0 and 1, but is not limited thereto. When a1 is an integer of 2 or more, a plurality of L &lt; ₁ &gt; may be the same as or different from each other. If a1 is 0, (L _{1) a1} may represent a single bond.

In Formula 1, a2 means the number of L ₂ , and may be selected from 0, 1, 2, and 3. For example, in Formula 1, a2 may be selected from 0 and 1, but is not limited thereto. As another example, in the above formula (1), a2 may be 0, but is not limited thereto. When a2 is an integer of 2 or more, plural L &lt; ₂ &gt; may be the same as or different from each other. When a2 is 0, (L ₂ ) _a2 may mean a single bond.

In Formula 1, a3 means the number of L ₃ , and may be selected from 0, 1, 2, and 3. For example, in Formula 1, a3 may be selected from 0 and 1, but is not limited thereto. As another example, in the above formula (1), a3 may be 0, but is not limited thereto. When a3 is an integer of 2 or more, a plurality of L &lt; ₃ &gt; may be the same as or different from each other. If a3 is 0, (L _{3) a3} may represent a single bond.

In the above formula (1), R ₁ to R ₃ independently represent a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ A substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C _A substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, Substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic groups.

For example, in Formula 1, R ₁ to R ₃ independently represent a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec- A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, a naphthyl group, An acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group An anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, A perfluorenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, o a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, An isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, an imidazolyl group, an imidazolyl group, A benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, an imidazolinyl group, A benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolyl group, naphthyl group, benzyl group, benzyl group, benzyl group, benzyl group, benzyl group, benzyl group, benzyl group, benzyl group, A triazinyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, A dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyridinyl group, An imidazopyrimidinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group, a pyrimidobenzothiophenyl group, a pyrimidobenzothiophenyl group, a pyrimidobenzothiophenyl group, an imidazopyrimidinyl group, )group; And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, an indacenyl group, an acenaphthyl group, , A spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, A thiophenyl group, an imidazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, , Thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl , A pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a benzoquinolinyl group, a phthalazinyl group, , A quinoxalinyl group, a quinazolinyl group, a cyano group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, Substituted with at least one of an oxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group A phenyl group, a phenanthrenyl group, an indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spioro-fluorenyl group, a benzofluorenyl group, , A phenalenyl group, a phenanthryl group A phenanthryl group, a phenanthryl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a klychenyl group, a naphthacenyl group, A thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, , A pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a benzoquinolinyl group, a phthalazinyl group, , A benzoquinolinyl group, a benzoquinazolinyl group, a cyano group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzoquinazolinyl group, A thiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, a A benzothiophenyl group, a dibenzothiophenyl group, a dibenzothiazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazole group, a thiadiazole group, a thiadiazole group, a thiadiazole group, An imidazopyridinyl group, an imidazopyrimidinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group and a pyrimidobenzothiophenyl group; , But is not limited thereto.

As another example, R ₁ to R ₃ in the general formula (1)

A thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, An isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a naphthyridinyl group , A quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a triazolyl group, a triazinyl group, An imidazopyrimidinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group, and a pyrimidobenzothiophenyl group; a heterocyclic group such as a pyrimidinyl group, an imidazopyrimidinyl group, an imidazopyrimidinyl group, And

A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms such as a methyl group, an ethyl group, a n-propyl group, a tert-butyl group, a methoxy group, an ethoxy group, A thiophene group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, an isoxazolyl group, an isoxazolyl group, an isoxazolyl group, A pyridinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, A carbazolyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, , A dibenzofuranyl group, and a dibenzothiophenyl group, which is substituted with at least one of a phenyl group, A thiazolyl group, a thiazolyl group, an isothiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, A thiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a naphthyridinyl group, A benzothiophenyl group, a triazolyl group, a triazinyl group, a dibenzofuranyl group, a benzothiopyranyl group, a thiazolyl group, a thienyl group, a thienyl group, a thienyl group, A dibenzothiophenyl group, a dibenzosilyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group and a pyrimidobenzothiophenyl group; , But is not limited thereto.

As another example, in the above formula (1), R ₁ to R ₃ independently of each other may be represented by any one of the following formulas (5-1) to (5-51), but are not limited thereto:

Of the above formulas (5-1) to (5-51)

Y ₅₁ is selected from C (R ₅₄ ) (R ₅₅ ), N (R ₅₄ ), O and S;

R ₅₁ to R ₅₅ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, A sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, -CD ₃ , -CF ₃ , a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, A phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klychenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group , An isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group; ;

a51 is selected from 1, 2, 3, 4 and 5;

a52 is selected from 1, 2, 3, 4, 5, 6 and 7;

a53 is selected from 1, 2, 3, 4, 5 and 6;

a54 is selected from 1, 2 and 3;

a55 is selected from 1, 2, 3 and 4;

* Is the binding site with neighboring atoms.

As another example, in the above formula (1), R ₁ to R ₃ independently of each other may be represented by any one of the following formulas (6-1) to (6-83), but are not limited thereto:

Of the above formulas (6-1) to (6-83)

t-Bu is a tert-butyl group;

Ph is a phenyl group;

* Is the binding site with neighboring atoms.

Wherein R ₄ and R ₅ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, A substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl groups, substituted or unsubstituted It may be selected from aromatic heterocyclic group condensed polycyclic-1 is a non-fused polycyclic aromatic group and a substituted or unsubstituted monovalent ratio.

For example, in Formula 1, R ₄ and R ₅ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, , A hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, A phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klychenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a pyrazinyl group, A quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group, but is not limited thereto.

As another example, in the above formula (1), R ₄ and R ₅ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, A hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a methyl group, an ethyl group, a n-propyl group, a tert-butyl group, a methoxy group, But is not limited thereto.

As another example, R ₄ and R ₅ in Formula 1 may be independently selected from hydrogen, deuterium, -F, -Cl, -Br, and -I, but is not limited thereto.

In the formula (1), n1 denotes the number of moieties represented by * - (L ₂ ) a ₂ -R ₂ , and may be selected from 0, 1, 2, 3 and 4. When n1 is 2 or more, the moieties represented by a plurality of * - (L ₂ ) _a2- R ₂ may be the same or different from each other. For example, n1 may be 1, but is not limited thereto.

In Formula 1, n2 is * - (L ₃₎ denotes the number of moieties represented by _a3 -R ₃ and 0, and can be selected from 1, 2, 3 and 4. If n2 is 2 or more, a plurality of * - (L ₃₎ moieties represented by _a3 -R ₃ may be the same or different from each other. For example, n2 may be 1, but is not limited thereto.

For example, the electron transporting material represented by Formula 1 may be represented by the following Formula 1-1, but is not limited thereto:

&Lt; Formula 1-1 >

In Formula 1-1,

L ₁ to L ₃ , a ₁ to a ₃ , R ₁ to R ₅ , n ₁ and n 2 refer to the above formula (1).

As another example, the electron transporting material represented by Formula 1 may be represented by the following Formula 1-11, but is not limited thereto:

&Lt; Formula 1-11 &

In the above formula (1-11)

L ₁ , a ₁ and R ₁ to R ₃ refer to the above formula (1).

For example, in Formula 1-11, L ₁ is represented by any one of formulas 4-1 to 4-56, and a 1 may be selected from 0 and 1, but is not limited thereto.

As another example, in the above formula (1-11), R ₁ to R ₃ may be independently represented by any one of the above formulas (6-1) to (6-83), but are not limited thereto.

As another example, the electron transporting material represented by Formula 1 may be selected from the following compounds, but is not limited thereto:

The electron transporting material represented by the above formula (1) has a high hole blocking property because of its deep HOMO. Therefore, the efficiency of the organic light emitting device including the electron transporting material can be enhanced because the excitons can be effectively integrated into the light emitting layer.

For example, the electron transporting region may further include an alkali metal complex in addition to the electron transporting material represented by Formula 1. [ For example, the electron transporting material represented by Formula 1 and the alkali metal complex may be included in the electron transporting layer in the electron transporting region.

The alkali metal complex may be represented by any one of the following formulas (2-1) to (2-4), but is not limited thereto.

&Lt; Formula (2-1)

&Lt; Formula (2-2)

<Formula 2-3>

<Formula 2-4>

Among the above-mentioned formulas (2-1) to (2-4)

M is an alkali metal;

R ₂₁ to R ₂₃ independently of each other refer to the description of R ₄ in the above formula (1);

R ₂₁ to R ₂₃ may optionally be connected to form a ring;

a21 and a22 are independently selected from 1, 2, 3, and 4;

For example, in the above formulas (2-1) to (2-4), M may be selected from Li, Na and Cs, but is not limited thereto.

As another example, M may be Li, but is not limited thereto.

The alkali metal complexes represented by any one of formulas (2-1) to (2-4) may be selected from among ET-D1 to ET-D8, but are not limited thereto:

The electron transporting material to the alkali metal complex is included in a weight ratio of 10:90 to 90:10, 20:80 to 80:20, 30:70 to 70:30, 40:60 to 60:40, or 50:50 But is not limited thereto.

Due to the interaction between the metal ion of the alkali metal complex and the nitrogen atom contained in the phenanthridine core of the electron transporting material represented by Formula 1, the organic light emitting element comprising the alkali metal complex and the electron transporting material Since the electron transportability is high, the efficiency can be improved.

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 further include at least one of an addition to the electron transporting material represented by Formula 1, BCP, Bphen and to Alq _3, Balq, TAZ and NTAZ.

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

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

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

In the present specification, the C ₂ -C ₆₀ alkynyl group has a structure containing one or more carbon triple bonds at the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include ethynyl, propynyl, , And the like. In the present specification, the C ₂ -C ₆₀ alkynylene group means a divalent group having the same structure as the C ₂ -C ₆₀ alkynyl group.

In the present specification, the C ₃ -C ₁₀ cycloalkyl group means a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, Tyl group and the like. The C ₃ -C ₁₀ cycloalkylene group of the specification and the second having the same structure as the above C ₃ -C ₁₀ cycloalkyl group means a group.

In the present specification, a C ₁ -C ₁₀ heterocycloalkyl group means a monovalent monocyclic group having 1 to 10 carbon atoms including at least one hetero atom selected from N, O, P and S as a ring-forming atom, Examples include tetrahydrofuranyl, tetrahydrothiophenyl, and the like. In the present specification, a C ₁ -C ₁₀ heterocycloalkylene group means a divalent group having the same structure as the above-mentioned C ₁ -C ₁₀ heterocycloalkyl group.

In the present specification, the C ₃ -C ₁₀ cycloalkenyl group 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 a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group and the like. In the present specification, the C ₃ -C ₁₀ cycloalkenylene group means a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkenyl group.

In the present specification, the C ₁ -C ₁₀ heterocycloalkenyl group is a monovalent monocyclic group having 1 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. Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl group include a 2,3-hyrofuranyl group, a 2,3-hydrothiophenyl group and the like. In the present specification, the C ₁ -C ₁₀ heterocycloalkenylene group means a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkenyl group.

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

As used herein, a C ₁ -C ₆₀ heteroaryl group means a monovalent 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 1 to 60 carbon atoms And a C ₁ -C ₆₀ heteroarylene group 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 1 to 60 carbon atoms do. Specific examples of the C ₁ -C ₆₀ heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group and the like. When the C ₁ -C ₆₀ heteroaryl group and the C ₁ -C ₆₀ heteroarylene group include two or more rings, two or more rings may be fused together.

In the present specification, the C ₆ -C ₆₀ aryloxy group indicates -OA ₁₀₂ (wherein A ₁₀₂ is the C ₆ -C ₆₀ aryl group), the C ₆ -C ₆₀ arylthio is -SA ₁₀₃ , And A ₁₀₃ is the above-mentioned C ₆ -C ₆₀ aryl device).

A monovalent non-aromatic condensed polycyclic group in the present specification is a monovalent non-aromatic condensed polycyclic group in which two or more rings are condensed with each other and contain only carbon as the ring forming atom (for example, the number of carbon atoms may be from 8 to 60) Means a monovalent group having non-aromacity. Examples of the non-aromatic condensed polycyclic group include a fluorenyl group 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.

A monovalent non-aromatic heterocyclic polycyclic group in the present specification is a group in which two or more rings are condensed with each other and N, O, P, and S Quot; means a monovalent group containing a selected heteroatom, wherein the whole molecule has non-aromacity. The monovalent non-aromatic heterocyclic polycyclic group includes a carbazolyl group 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, the substituted C ₂ -C ₁₀ alkylene group, the substituted C ₃ -C ₁₀ cycloalkylene group, the substituted C ₁ -C ₁₀ heterocycloalkylene group, the substituted C ₃ -C ₁₀ cycloalkenylene group, the substituted Substituted C ₁ -C ₁₀ heterocycloalkylene groups, substituted C ₆ -C ₆₀ arylene groups, substituted C ₁ -C ₆₀ heteroarylene groups, substituted divalent non-aromatic condensed polycyclic groups, substituted divalent non- An aromatic heterocyclic polycyclic group, a substituted C ₁ -C ₆₀ alkyl group, a substituted C ₂ -C ₆₀ alkenyl group, a substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₆₀ alkoxy group, C ₁₀ cycloalkyl group, a substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl group, a substituted a C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted a non-aromatic condensed polycyclic groups, and substituted monovalent non-aromatic Heterocondensation At least one of the substituents in the polycyclic group is,

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -N (Q _{11) (Q 12), -Si (Q} 13) (Q 14) (Q 15) and _{-B (Q 16) (Q 17} ) of the at least one substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl , A C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

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 aryl A C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group;

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocyclo alkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ - C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 21) (Q} 22), -Si (Q 23) (Q 24) (Q 25) and _{-B (Q 26) (Q 27} ) of the at least one substituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkyl alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ H. Heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic heterocyclic polycyclic group; And

_{-N (Q 31) (Q 32} ), -Si (Q 33) (Q 34) (Q 35) and _{-B (Q 36) (Q 37} ); ;

Q ₁₁ to Q _17, Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are, each independently, hydrogen, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, C ₁ to each other - C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic heterocyclic is selected from a condensed polycyclic group, aromatic condensed polycyclic group, and 1 is non.

For example, the substituted C ₂ -C ₁₀ alkylene group, the substituted C ₃ -C ₁₀ cycloalkylene group, the substituted C ₁ -C ₁₀ heterocycloalkylene group, the substituted C ₃ -C ₁₀ cycloalkenylene group, Substituted C ₁ -C ₁₀ heterocycloalkenylene groups, substituted C ₆ -C ₆₀ arylene groups, substituted C ₁ -C ₆₀ heteroarylene groups, substituted divalent non-aromatic condensed polycyclic groups, substituted divalent groups - an aromatic heterocyclic polycyclic group, a substituted C ₁ -C ₆₀ alkyl group, a substituted C ₂ -C ₆₀ alkenyl group, a substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₆₀ alkoxy group, A substituted C ₁ -C ₁₀ cycloalkyl group, a substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted a non-aromatic condensed polycyclic groups, and substituted monovalent non- Aromatic hetero-condensation At least one of the substituents of the ring group is,

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₃₀ alkyl group, a C ₂ -C ₃₀ alkenyl group, a C ₂ -C ₃₀ alkynyl group and a C ₁ -C ₃₀ alkoxy group;

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₃₀ aryl group, C ₆ -C ₃₀ aryloxy, C ₆ -C ₃₀ arylthio, C ₁ -C ₃₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -N (Q _{11) (Q 12), -Si (Q} 13) (Q 14) (Q 15) and _{-B (Q 16) (Q 17} ) of the at least one substituted, C ₁ -C ₃₀ alkyl, C ₂ -C ₃₀ alkenyl , A C ₂ -C ₃₀ alkynyl group and a C ₁ -C ₃₀ alkoxy group;

A cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a cyclohexyl group, A carbamoyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, Phenanthrenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, and spearyl groups substituted with at least one of a quinolinyl group, a quinoxalinyl group, A phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a fluorantrenyl group, a triphenylenyl group, a pyrenyl group, a klychenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, , Hexacenyl group, pyrrolyl group, imidazole A pyridazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group A phenanthridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, A thiazolyl group, a tetrazolyl group, an oxadiazole group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, A thiazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyrimidinyl group and an imidazopyridinyl group;

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₃₀ alkyl group, a C ₂ -C ₃₀ alkenyl group, a C ₂ -C ₃₀ alkynyl group and a C ₁ -C ₃₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocyclo alkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₃₀ aryl group, C ₆ -C ₃₀ aryloxy, C ₆ -C ₃₀ arylthio, C ₁ - C ₃₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 21) (Q} 22), -Si (Q 23) (Q 24) (Q 25) and -B at least one (Q ₂₆₎ (Q ₂₇₎ as one substitution, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, a cyclopentenyl group, a cyclohexenyl group, a heptenyl cycloalkyl group, a phenyl group, a naphthyl group , Anthracenyl group, pyrenyl group, phenanthrenyl group , A fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, An acetyl group, an acenaphthyl group, an acenaphthyl group, an acenaphthyl group, an acenaphthyl group, an acenaphthyl group, an acenaphthyl group, an acenaphthyl group, an acenaphthyl group, an acenaphthyl group, an acenaphthyl group, A phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a fluorantrenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a phenenyl group, a phenanthryl group, a phenanthryl group, A pyridyl group, a pyridinyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a furyl group, an imidazolyl group, A quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinolyl group, A thiazolyl group, a thiazolyl group, a thiazolyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, , A furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, , Triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group and imidazopyridinyl group; And

_{-N (Q 31) (Q 32} ), -Si (Q 33) (Q 34) (Q 35) and _{-B (Q 36) (Q 37} ); ;

Q ₁₁ to Q ₁₇ and Q ₃₁ to Q ₃₇ independently represent hydrogen, a C ₁ -C ₃₀ alkyl group, a C ₂ -C ₃₀ alkenyl group, a C ₂ -C ₃₀ alkynyl group, a C ₁ -C ₃₀ alkoxy group, a cyclo A cyclopentenyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a cycloheptenyl group, a cycloheptenyl group, A thiazolyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, A phenanthrenyl group, an indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spirobifluorenyl group which is substituted with at least one of a pyridyl group, A fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluorantrenyl group, A pyridyl group, a pyridinyl group, a pyridinyl group, a pyridazinyl group, a pyridazinyl group, a pyranyl group, a pyranyl group, a pyranyl group, A pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, A phenanthrolinyl group, a phenanthrolinyl group, a benzoxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzoyl group, a benzothiophenyl group, Thiazolyl, thiazolyl, isothiazolyl, benzothiazolyl, isoxazolyl, oxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzofuranyl, A thiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, An imidazopyrimidinyl group, and an imidazopyridinyl group, but the present invention is not limited thereto.

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

Hereinafter, compounds and organic light emitting devices according to one embodiment of the present invention will be described in more detail with reference to Synthesis Examples and Examples, but the present invention is not limited to the following Synthesis Examples and Examples. In the following Synthesis Examples, the amounts of 'B' and 'A' used in the expression "B" was used in place of "A" were the same on the molar equivalent basis.

[Example]

Synthesis Example 1: Synthesis of Compound 5

1) Synthesis of intermediate 1

4,4-dibromobiphenyl (20.0 g, 64.0 mmol) was added to a 1000-mL three-necked flask, dissolved in 70 mL of CH ₂ Cl ₂ , 240 mL of acetic anhydride was added, Respectively. The temperature of the reaction was lowered to 0 ° C using ice, and a mixture of 50 mL of acetic acid and 70 mL of nitric acid was slowly added dropwise using a dropping funnel. After stirring for 8 hours, the temperature was lowered with ice, and the reaction was poured into 300 mL of 2M NaOH. Stir 1 h and filter the resulting yellow solid. The reaction mixture was extracted with CH ₂ Cl ₂ , dried over anhydrous MgSO ₄ , and evaporated under reduced pressure. Washed with hexane and dried to obtain Intermediate 1 (yield: 17.0 g, 74%). The structure of Intermediate 1 was confirmed by ¹ H NMR.

_{^{1 H NMR (300MHz, CD 2}} Cl 2, δ): 8.10 (d, 1H), 7.85 (dd, 1H), 7.62 (d, 2H), 7.35 (d, 1H), 7.22 ppm (d, 2H).

2) Synthesis of intermediate 2

A 500 mL three-necked flask was charged with Intermediate 1 (17.0 g, 47.6 mmol) dissolved in 160 mL of ethanol, followed by the addition of 80 mL of 35% HCl. The tin powder (11.3 g, 95.2 mmol) was slowly added and refluxed at 90 ° C for 9 hours. The temperature of the reaction was lowered to room temperature and 2 M NaOH was added until the pH reached 9. The resulting solid was filtered off, washed thoroughly with distilled water and dried to give Intermediate 2 (yield: 13.1 g, 84%). The structure of intermediate 2 was confirmed by ¹ H NMR.

^{1 H NMR (300MHz, CDCl3,} δ): 7.60 (d, 2H), 7.31 (d, 2H), 6.95 - 6.93 (m, 3H), 3.78 ppm (s, 2H).

3) Synthesis of intermediate 3

A 500 mL three-necked flask was charged with Intermediate 2 (10.0 g, 30.6 mmol) and dissolved in 200 mL of THF, followed by 10 mL of triethylamine. The temperature of the reaction was lowered to 0 캜, and 4-bromobenzoyl chloride (10.4 g, 47.4 mmol) was slowly added dropwise to the reaction solution in THF. The mixture was stirred at room temperature for 9 hours. The residue was extracted with ethyl acetate, dried over anhydrous MgSO ₄ , and then distilled under reduced pressure. The crude product was purified by column chromatography using an eluant of ethyl acetate and hexane mixed at a ratio of 1: 50 to obtain Intermediate 3 (yield: 8.0 g, 51%). The structure of intermediate 3 was confirmed by ¹ H NMR.

^{1 H NMR (300MHz, CD2Cl2,} δ): 8.67 (d, 1H), 7.82 (s, 1H), 7.70 (d, 2H), 7.63 (d, 2H), 7.53 (d, 2H), 7.42 (dd, 1H), 7.34 (d, 2H), 7.21 ppm (d, 1 H).

4) Synthesis of intermediate 4

Intermediate 3 (8.0 g, 15.6 mmol) was added to a 250 mL three-necked flask and dissolved in 40 mL of nitrobenzene, followed by POCl ₃ (3.6 g, 21.8 mmol). After refluxing at 200 ° C for 1 hour, tin chloride (0.8 g, 3.0 mmol) was added slowly and the reaction was terminated after 2 hours. The reaction mixture was extracted with ethyl acetate, dried over anhydrous MgSO ₄ , and evaporated under reduced pressure. Purification by column chromatography using ethyl acetate and hexane gave an intermediate 4 (yield: 4.7 g, 61%) The structure of intermediate 4 was confirmed by ¹ H NMR.

^{1 H NMR (300MHz, CDCl3,} δ): 8.54 (d, 1H), 8.43 (d, 2H), 8.21 (s, 1H), 7.99 (d, 1H), 7.82 (d, 1H), 7.75 (d, 2H), 7.61 ppm (d, 2H).

5) Synthesis of Compound 5

Intermediate 4 (3.0 g, 6.1 mmol) and Pd (PPh ₃ ) ₄ (0.3 g, 0.3 mmol) were added to a 250 mL three-necked flask and dissolved with 30 mL of toluene and stirred. 3- (tributylstannyl) pyridine (11.1 g, 30.4 mmol) was added thereto and refluxed at 90 ° C for 9 hours. CHCl ₃ and then dried over anhydrous MgSO ₄ to remove moisture and then distilled under reduced pressure. CH ₂ Cl ₂ and ethanol in a ratio of 20: 1, to obtain Compound 5 (yield: 0.7 g, 23%). The structure of Compound 5 was confirmed by ¹ H NMR and Mass.

^{1 H NMR (300MHz, CDCl3,} δ): 9.10 (d, 1H), 8.97 (dd, 2H), 8.77 (d, 1H), 8.68 (d, 1H), 8.67 (m, 3H), 8.55 (d, 1H), 8.42 (d, 1H), 8.04-8.03 (m, 2H), 8.01-7.95 (m, 5H), 7.84 (d, 2H), 7.46 ppm (m, 3H);

HRMS (EI, m / z): [M ^&lt; ⁺ &^gt;] calcd for C34H22N4486.1844; found: 486.1846.

Synthesis Example 2: Synthesis of Compound 8

1) Synthesis of intermediate 6

In a 500 mL three-necked flask, add Intermediate 2 (8.0 g, 25.4 mmol), dissolve in 250 mL of THF, and add 8 mL of triethylamine. After the temperature of the reaction was lowered to 0 ° C, 2-naphthoyl chloride (7.2 g, 37.9 mmol) was slowly added dropwise to THF. The mixture was stirred at room temperature for 9 hours. The residue was extracted with ethyl acetate, dried over anhydrous MgSO ₄ , and then distilled under reduced pressure. Ethyl acetate and hexane at a ratio of 1: 50, and then recrystallized from CH ₂ Cl ₂ and hexane to obtain Intermediate 6 (yield: 4.0 g, 32%). The structure of intermediate 6 was confirmed by ¹ H NMR.

^{1 H NMR (300MHz, CD2Cl2,} δ): 8.76 (s, 1H), 8.15 (s, 1H), 8.04 (s, 1H), 7.93 (t, 3H), 7.74 - 7.69 (m, 3H), 7.65 - 7.58 (m, 2H), 7.45-7.39 (m, 3H), 7.23 ppm (d, 1H).

2) Synthesis of intermediate 7

Intermediate 6 (4.0 g, 8.3 mmol) was added to a 250 mL three-necked flask and dissolved in 23 mL of nitrobenzene. POCl ₃ (1.8 g, 12.0 mmol) was then added. After refluxing at 200 ° C for 1 hour, tin chloride (0.4 g, 1.7 mmol) was added slowly and the reaction was terminated after 2 hours. The residue was extracted with ethyl acetate, dried over anhydrous MgSO ₄ , and then distilled under reduced pressure. Separation by column chromatography using an eluent mixture of ethyl acetate and hexane gave Intermediate 7 (yield: 2.5 g, 63%). The structure of Intermediate 7 was confirmed by ¹ H NMR.

^{1 H NMR (300MHz, CDCl3,} δ): 8.56 (d, 1H), 8.46 (d, 2H), 8.32 (d, 1H), 8.22 (s, 1H), 8.09 (d, 1H), 7.99 (m, 3H), 7.83 (m, 2H), 7.62 ppm (t, 2H).

3) Synthesis of Compound 8

(2.5 g, 5.4 mmol) and naphthalen-2-ylboronic acid (2.8 g, 16.2 mmol) were added to a 250 mL three-necked flask and dissolved with 15 mL of THF and 25 mL of toluene. Lt; / RTI &gt; 2 MK ₂ CO _{3 (} 20 mL) and Pd (PPh ₃ ) ₄ (0.5 g, 0.4 mmol) were added and refluxed at 80 ° C for 9 hours. CHCl ₃ and then dried over anhydrous MgSO ₄ to remove moisture and then distilled under reduced pressure. The residue was recrystallized from CHCl ₃ and hexane, and the residue was subjected to soxhlet in the order of hexane, toluene and CHCl ₃ to obtain Compound 8 (yield: 0.6 g, 20%). The structure of Compound 8 was confirmed by ¹ H NMR and MS.

^{1 H NMR (300MHz, CDCl,} δ): 8.96 (d, 1H), 8.87 (d, 1H), 8.67 (d, 1H), 8.60 (d, 1H), 8.38 (dd, 3H), 8.23 (dd, 1H), 8.15 (d, 2H), 8.07-7.82 (m, 11H), 7.69-7.50 ppm (m, 6H);

HRMS (EI, m / z): [M ⁺ ] calcd for C43H27N 557.2143; found: 557.2142.

Synthesis Example 3: Synthesis of Compound 11

1) Synthesis of intermediate 9

Intermediate 2 (3.2 g, 9.7 mmol) was added to a 500 mL three-necked flask and dissolved in 120 mL of THF, followed by 5 mL of triethylamine. After the temperature of the reaction was lowered to 0 ° C, benzoimidazol-2-yl benzoyl chloride (3.9 g, 11.7 mmol) was slowly added dropwise to THF. The mixture was stirred at room temperature for 9 hours. The residue was extracted with ethyl acetate, dried over anhydrous MgSO ₄ , and then distilled under reduced pressure. The residue was purified by column chromatography using an eluant of ethyl acetate and hexane mixed at a ratio of 1: 2 to obtain Intermediate 9 (yield: 2.5 g, 41%). The structure of intermediate 9 was confirmed by ¹ H NMR. Y

^{1 H NMR (300MHz, CD2Cl2,} δ): 8.69 (d, 1H), 7.86 (d, 2H), 7.67 (m, 4H), 7.57 (m, 5H), 7.43 - 7.30 (m, 8H), 7.20 ppm (d, 1 H).

2) Synthesis of intermediate 10

Intermediate 9 (2.5 g, 4.0 mmol) was added to a 250 mL three-necked flask and dissolved in 25 mL of nitrobenzene. POCl ₃ (0.8 g, 5.6 mmol) was then added. After refluxing at 200 ° C for 1 hour, tin chloride (0.2 g, 0.8 mmol) was added slowly and the reaction was terminated after 2 hours. The residue was extracted with ethyl acetate, dried over anhydrous MgSO ₄ , and then distilled under reduced pressure. The intermediate 10 (yield: 2.0 g, 82%) was obtained by column chromatography using an eluent comprising ethyl acetate and hexane. The structure of Intermediate 10 was confirmed by ¹ H NMR.

¹ H NMR (300 MHz, CD ² Cl ² , 隆): 8.58 (d, IH), 8.50 (d, IH), 8.37 m, 4H), 7.72-7.58 (m, 5H), 7.49-7.40 (m, 2H), 7.37-7.33 ppm (m, 3H).

3) Synthesis of Compound 11

Intermediate 10 (2.0 g, 3.3 mmol) and naphthalene-2-ylboronic acid (1.7 g, 9.8 mmol) were added to a 250 mL three-necked flask and dissolved with 10 mL of THF and 20 mL of toluene. 2 MK ₂ CO ₃ 16 mL and Pd (PPh ₃ ) ₄ (0.3 g, 0.3 mmol) were added and refluxed at 80 ° C. for 9 hours. CHCl ₃ and then dried over anhydrous MgSO ₄ to remove moisture and then distilled under reduced pressure. Compound 11 (yield: 0.6 g, 32%) was obtained by separating by column chromatography using an eluent comprising ethyl acetate and hexane. The structure of compound 11 was confirmed by ¹ H NMR and MS.

^{1 H NMR (300MHz, CD2Cl2,} δ): 8.93 (d, 1H), 8.85 (d, 1H), 8.63 (d, 1H), 8.52 (d, 1H), 8.39 - 8.36 (m, 2H), 8.24 - 8.18 (m, 2H), 8.07-7.86 (m, 13H), 7.62-7.34 ppm (m, 12H);

HRMS (EI, m / z): [M ⁺ ] calcd for C52H33N3699.2674; found: 699.2678.

Example 1

The front substrate formed of ITO / Ag / ITO was ultrasonically cleaned for 5 minutes using isopropyl alcohol and pure water, and then irradiated with ultraviolet rays for 10 minutes, exposed to ozone, cleaned, and the ITO glass substrate was installed in a vacuum deposition apparatus Respectively.

HT1 was deposited on the ITO anode to form a hole injection layer having a thickness of 100 A, HT3 was deposited on the hole injection layer to form a hole transport layer having a thickness of 1100 A, and then an ADN (host) And FD9 (dopant) were co-deposited at a weight ratio of 200: 3 to form a light emitting layer having a thickness of 200 ANGSTROM.

Compound 5 was deposited on the light emitting layer to form an electron transport layer having a thickness of 360 ANGSTROM. ET-D1 was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 ANGSTROM. Then, Mg and Ag 110: 10 by weight to form a cathode having a thickness of 110 Å. Thus, a front organic light emitting device was fabricated.

Example 2

An organic luminescent device was fabricated in the same manner as in Example 1, except that Compound 8 was used instead of Compound 5 in forming the electron transport layer.

Example 3

An organic luminescent device was fabricated in the same manner as in Example 1, except that Compound 11 was used instead of Compound 5 in forming the electron transport layer.

Example 4

The front substrate formed of ITO / Ag / ITO was ultrasonically cleaned for 5 minutes using isopropyl alcohol and pure water, and then irradiated with ultraviolet rays for 10 minutes, exposed to ozone, cleaned, and the ITO glass substrate was installed in a vacuum deposition apparatus Respectively.

HT1 was deposited on the ITO anode to form a hole injection layer having a thickness of 100 A, HT3 was deposited on the hole injection layer to form a hole transport layer having a thickness of 1100 A, and then an ADN (host) And FD9 (dopant) were co-deposited at a weight ratio of 200: 3 to form a light emitting layer having a thickness of 200 ANGSTROM.

Compound 5 and ET-D1 were co-deposited on the light emitting layer at a weight ratio of 50:50 to form an electron transport layer having a thickness of 360 ANGSTROM. ET-D1 was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 ANGSTROM Mg and Ag were co-deposited on the electron injecting layer at a weight ratio of 110: 10 to form a cathode having a thickness of 110 Å. Thus, an organic light emitting device was fabricated.

Example 5

An organic luminescent device was fabricated in the same manner as in Example 4, except that Compound 8 was used instead of Compound 5 in forming the electron transport layer.

Example 6

An organic luminescent device was fabricated in the same manner as in Example 4, except that Compound 11 was used instead of Compound 5 in forming the electron transport layer.

Comparative Example 1

An organic luminescent device was fabricated in the same manner as in Example 1, except that Alq ₃ was used instead of the compound 5 in forming the electron transport layer.

Comparative Example 2

An organic luminescent device was fabricated in the same manner as in Example 1, except that Compound A was used instead of Compound 5 in forming the electron transport layer.

<Compound A>

Comparative Example 3

An organic luminescent device was fabricated in the same manner as in Example 4, except that Alq ₃ was used instead of the compound 5 in forming the electron transport layer.

Comparative Example 2

An organic luminescent device was fabricated in the same manner as in Example 4, except that Compound A was used in place of Compound 5 in forming the electron transport layer.

<Compound A>

Evaluation example 1

The driving voltage, the current density, the luminance, the efficiency, the luminescence color and the half-life of the organic light-emitting devices fabricated in Examples 1 to 6 and Comparative Examples 1 to 4 were measured using a Kethlee SMU 236 and a luminance meter PR650, Tables 1 and 2 show:

Electron transport layer Driving voltage
(V) Current density
(MA / cm2) Luminance
(cd / m 2) efficiency
(cd / A) CIE_x CIE_y Example 1 Compound 5 3.9 16.9 600 3.4 0.147 0.040 Example 2 Compound 8 4.5 16.6 600 3.2 0.149 0.041 Example 3 Compound 11 5.2 16.1 600 3.4 0.144 0.040 Example 4 Compound 5: Liq = 50: 50 4.8 14.5 600 4.5 0.141 0.048 Example 5 Compound 8: Liq = 50: 50 5.2 15.3 600 4.2 0.143 0.045 Example 6 Compound 11: Liq = 50: 50 4.9 14.8 600 4.2 0.146 0.048 Comparative Example 1 Alq ₃ 6.6 23.6 600 2.6 0.145 0.044 Comparative Example 2 Compound A 5.1 16.9 600 3.0 0.144 0.047 Comparative Example 3 Compound ₃ Alq: Liq = 50:50 6.3 17.6 600 3.2 0.146 0.043 Comparative Example 4 Compound A: Liq = 50: 50 4.5 14.6 600 3.6 0.141 0.043

From Table 1, the driving voltage, current density, luminance, efficiency and color purity of the organic light-emitting device of Examples 1 to 6 are the same as those of the organic light-emitting device of Comparative Examples 1 to 4 in terms of driving voltage, current density, It can be confirmed that it is superior to the color purity.

Evaluation example 2

Compound 5 was subjected to thermogravimetric analysis (TGA) and differential thermal calorimetry (DSC) while heating at 40 ° C to 800 ° C at a rate of 10 ° C / min under a nitrogen atmosphere. The results of the analysis of Compound 5 are shown in Figures 2, 3 and Table 2:

T _d T _g T _m 438 ° C 109 ℃ 253 ° C

* T _d : decomposition temperature, T _g : glass transition temperature, T _m : melting point

Evaluation example 3

Compound 5 in a concentration of 1X10 &lt; ^-5 &gt; M was dissolved in a chloroform solvent to obtain UV and PL spectra. Furthermore, Compound 5 was formed into a film to obtain UV and PL spectra. The results are shown in Figures 4, 5 and Table 3:

UV spectrum (nm) PL spectrum (nm) solution film solution film 294 298 393 421

Evaluation example  4

The electrochemical characteristics of Compound 5 were measured by a circulating voltage-current method, and the results are shown in Fig. The HOMO of Compound 5 was 6.77 eV, the LUMO was 3.67 eV, and the band gap was 3.10.

10: Organic light emitting device
110: first electrode
150: organic layer
190: second electrode

Claims (20)

A first electrode; A second electrode facing the first electrode; And an organic layer including a light emitting layer interposed between the first electrode and the second electrode;
An electron transporting region interposed between the light emitting layer and the second electrode;
Wherein the electron transporting region comprises an electron transporting material represented by the following Formula 1:
&Lt; Formula 1 >

In Formula 1,
L ₁ to L ₃ independently represent a substituted or unsubstituted C ₂ -C ₁₀ alkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl A substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ arylene group, a C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted 2 non-aromatic condensed polycyclic group, and a substituted or unsubstituted 2 non-aromatic heterocyclic is selected from the condensed polycyclic groups;
a1 to a3 are independently selected from 0, 1, 2 and 3;
R ₁ to R ₃ independently represent a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, A substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ hetero Cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted 1 is selected from non-aromatic heterocyclic polycyclic groups;
R ₄ and R ₅ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl, a cyano, a nitro, an amino, an amidino, a hydrazine, a hydrazone, acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C _A substituted or unsubstituted C ₁ -C ₆ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C _A substituted or unsubstituted C ₁ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic Sum polycyclic group, and a substituted or unsubstituted 1, a non-aromatic heterocyclic is selected from a condensed polycyclic group;
n1 and n2 are independently selected from 0, 1, 2, 3 and 4;
The substituted C ₂ -C ₁₀ alkylene group, the substituted C ₃ -C ₁₀ cycloalkylene group, the substituted C ₁ -C ₁₀ heterocycloalkylene group, the substituted C ₃ -C ₁₀ cycloalkenylene group, the substituted C ₁ -C ₁₀ cycloalkenylene group, -C ₁₀ heterocycloalkyl alkenylene group, substituted C ₆ -C ₆₀ aryl group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted divalent non-aromatic condensed polycyclic group, a substituted divalent non-aromatic hydrocarbon ring condensed A substituted C ₁ -C ₆₀ alkyl group, a substituted C ₂ -C ₆₀ alkenyl group, a substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cyclo alkyl, substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted a non-aromatic condensed polycyclic groups, and substituted monovalent non-aromatic heterocyclic fused polycyclic Group At least one of the ventilation,
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -N (Q _{11) (Q 12), -Si (Q} 13) (Q 14) (Q 15) and _{-B (Q 16) (Q 17} ) of the at least one substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl , A C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;
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 aryl A C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group;
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocyclo alkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ - C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 21) (Q} 22), -Si (Q 23) (Q 24) (Q 25) and _{-B (Q 26) (Q 27} ) of the at least one substituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkyl alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ H. Heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic heterocyclic polycyclic group; And
_{-N (Q 31) (Q 32} ), -Si (Q 33) (Q 34) (Q 35) and _{-B (Q 36) (Q 37} ); ;
Q ₁₁ to Q _17, Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are, each independently, hydrogen, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, C ₁ to each other - C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic heterocyclic is selected from a condensed polycyclic group, aromatic condensed polycyclic group, and 1 is non. The method according to claim 1,
L ₁ to L ₃ are, independently of each other,
A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, An acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrene group, A phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenyl group, A naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubidecylene group, rubicenylene group, coronenylene group, ovalenylene group, pyrrolylene group, An isothiazolylene group, a thiophenylene group, a furanylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, An oxazolylene group, an isooxazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an iso An isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, carbazolylene group, phenanthridinylene group, acridinyl group, ene group, a phenanthrolinylene group, a phenazinylene group, a benzoimidazolylene group, a benzofuranylene group, a benzothiophenylene group, a benzothiazolylene group, an isobenzothiazolylene group, an isobenzooxazolylene group, an isobenzooxazolylene group, a triazolylene group, a tetrazolylene group, an isobenzothiazolyl group, an isobenzothiazolyl group, An oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group and a dibenzocarbazolylene group; And
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenyl group, Anthracenyl group, anthracenyl group, phenanthrenyl group, phenanthrenyl group, phenanthrenyl group, phenanthryl group, phenanthryl group, phenanthryl group, A fluorenyl group, a fluorenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, , An ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, A pyridinyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an imidazolyl group, an imidazolyl group, A phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, A benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, A phenylene group, a pentalenylene group, an indenylene group, a naphthyl group which is substituted with at least one of a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group and an imidazopyridinyl group, Azulenylene group, heptalenyl group A phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a phenanthrenylene group, an anthracenylene group, a phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, And examples thereof include a fluorenylene group, a fluorenylene group, a fluorenylene group, a fluorenylene group, a fluorenylene group, a fluorenylene group, a fluorenylene group, a fluorenenylene group, a triphenylenylene group, a pyrenylene group, a chryshenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, A thiophenylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a pyridinylene group, An isoindolylene group, an indolylene group, an indazolylene group, a prolinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthaloylphenylene group, a phenanthrene group, Naphthylidene group, quinoxalinylene group, , A quinazolinyl group, a quinazolinyl group, a quinazolinyl group, a cyclopentadienyl group, a benzothiophenylene group, a benzothiophenylene group, a benzothiophenylene group, a benzothiophenylene group, Benzothiophenylene group, dibenzothiophenylene group, dibenzothiophenylene group, dibenzothiophenylene group, dibenzothiophenylene group, dibenzothiophenylene group, dibenzothiophenylene group, dibenzothiophenylene group, dibenzothiophenylene group, dibenzothiophenylene group, dibenzothiophenylene group , Benzocarbazolylene group and dibenzocarbazolylene group; &Lt; / RTI &gt; The method according to claim 1,
L &_lt; ₁ &gt; to L &_lt; _{3 & gt} ; independently of one another are represented by any one of the following formulas (3-1) to

Among the above-mentioned formulas (3-1) to (3-31)
Y ₃₁ is selected from C (R ₃₃ ) (R ₃₄ ), N (R ₃₃ ), O and S;
R ₃₁ to R ₃₄ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, A sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spioro-fluorenyl group, Anthracenyl group, pyranyl group, pyridinyl group, pyridinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinolyl group, A thiazolyl group, a salinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group;
a31 is selected from 1, 2, 3 and 4;
a32 is selected from 1, 2, 3, 4, 5 and 6;
a33 is selected from 1, 2, 3, 4, 5, 6, 7 and 8;
a34 is selected from 1, 2, 3, 4 and 5;
a35 is selected from 1, 2 and 3;
* And * are independent sites of bonding to neighboring atoms. The method according to claim 1,
L &_lt; ₁ &gt; to L &_lt; _{3 & gt} ; each independently represent any one of the following formulas (4-1) to

Of the above-mentioned formulas (4-1) to (4-56)
* And * are independent sites of bonding to neighboring atoms. The method according to claim 1,
and a1 is selected from 0 and 1. The method according to claim 1,
and a2 and a3 are each 0. The method according to claim 1,
R ₁ to R ₃ are each independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec- An indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, an acenaphthyl group, an acenaphthyl group, , A fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoro group, And examples thereof include a fluorenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, A pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a heptadecenyl group, a heptadecenyl group, a heptadecenyl group, However, A thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, An isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a benzoquinolinyl group A phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group (for example, a benzoquinazolinyl group, a benzoquinazolinyl group, A cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a phenanthrolinyl group, A benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, Triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, A dibenzoyl group, a dibenzosilyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, A pyrimidobenzofuranyl group, a pyridobenzothiophenyl group, and a pyrimidobenzothiophenyl group; a pyrimidobenzofuranyl group; And
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, an indacenyl group, an acenaphthyl group, , A spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, A thiophenyl group, an imidazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, , Thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl , A pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a benzoquinolinyl group, a phthalazinyl group, , A quinoxalinyl group, a quinazolinyl group, a cyano group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, Substituted with at least one of an oxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group A phenyl group, a phenanthrenyl group, an indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spioro-fluorenyl group, a benzofluorenyl group, , A phenalenyl group, a phenanthryl group A phenanthryl group, a phenanthryl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a klychenyl group, a naphthacenyl group, A thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, , A pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a benzoquinolinyl group, a phthalazinyl group, , A benzoquinolinyl group, a benzoquinazolinyl group, a cyano group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzoquinazolinyl group, A thiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, a A benzothiophenyl group, a dibenzothiophenyl group, a dibenzothiazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazole group, a thiadiazole group, a thiadiazole group, a thiadiazole group, An imidazopyridinyl group, an imidazopyrimidinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group and a pyrimidobenzothiophenyl group; &Lt; / RTI &gt; The method according to claim 1,
R ₁ to R ₃ are, independently of each other,
A thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, An isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a naphthyridinyl group , A quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a triazolyl group, a triazinyl group, An imidazopyrimidinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group, and a pyrimidobenzothiophenyl group; a heterocyclic group such as a pyrimidinyl group, an imidazopyrimidinyl group, an imidazopyrimidinyl group, And
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms such as a methyl group, an ethyl group, a n-propyl group, a tert-butyl group, a methoxy group, an ethoxy group, A thiophene group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, an isoxazolyl group, an isoxazolyl group, an isoxazolyl group, A pyridinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, A carbazolyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, , A dibenzofuranyl group, and a dibenzothiophenyl group, which is substituted with at least one of a phenyl group, A thiazolyl group, a thiazolyl group, an isothiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, A thiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a naphthyridinyl group, A benzothiophenyl group, a triazolyl group, a triazinyl group, a dibenzofuranyl group, a benzothiopyranyl group, a thiazolyl group, a thienyl group, a thienyl group, a thienyl group, A dibenzothiophenyl group, a dibenzosilyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group and a pyrimidobenzothiophenyl group; &Lt; / RTI &gt; The method according to claim 1,
R ₁ to R ₃ are independently of each other represented by any one of the following formulas (5-1) to (5-51):

Of the above formulas (5-1) to (5-51)
Y ₅₁ is selected from C (R ₅₄ ) (R ₅₅ ), N (R ₅₄ ), O and S;
R ₅₁ to R ₅₅ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, A sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, -CD ₃ , -CF ₃ , a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, A phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klychenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group , An isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group; ;
a51 is selected from 1, 2, 3, 4 and 5;
a52 is selected from 1, 2, 3, 4, 5, 6 and 7;
a53 is selected from 1, 2, 3, 4, 5 and 6;
a54 is selected from 1, 2 and 3;
a55 is selected from 1, 2, 3 and 4;
* Is the binding site with neighboring atoms. The method according to claim 1,
R ₄ and R ₅ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl, a cyano, a nitro, an amino, an amidino, a hydrazine, a hydrazone, A sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, Anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, isoquinolinyl group, A quinazolinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group. The method according to claim 1,
Wherein the electron transporting material is represented by the following Formula 1-1:
&Lt; Formula 1-1 >

In Formula 1-1,
L ₁ to L ₃ , a ₁ to a ₃ , R ₁ to R ₅ , n ₁ and n 2 are the same as those described in the above formula (1). The method according to claim 1,
Wherein the electron transporting material is represented by the following Formula 1-11:
&Lt; Formula 1-11 &

In the above formula (1-11)
The definitions of L ₁ , a ₁ and R ₁ to R ₃ are the same as those described in the above formula (1). 13. The method of claim 12,
L ₁ is represented by any one of the following formulas (4-1) to (4-56), and a 1 is selected from 0 and 1:

Of the above-mentioned formulas (4-1) to (4-56)
* And * are binding sites with neighboring atoms. 13. The method of claim 12,
R ₁ to R ₃ independently represent an organic light-emitting element represented by any of the following formulas (6-1) to (6-83):

Of the above formulas (6-1) to (6-83)
t-Bu is a tert-butyl group;
Ph is a phenyl group;
* Is the binding site with neighboring atoms. The method according to claim 1,
Wherein the electron transporting material is selected from the following compounds:

The method according to claim 1,
Wherein the electron transport region further comprises an alkali metal complex. 17. The method of claim 16,
Wherein the alkali metal complex is represented by any one of the following Chemical Formulas 2-1 to 2-4:
&Lt; Formula (2-1)

&Lt; Formula (2-2)

<Formula 2-3>

<Formula 2-4>

Among the above-mentioned formulas (2-1) to (2-4)
M is an alkali metal;
R ₂₁ to R ₂₃ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C _A substituted or unsubstituted C ₁ -C ₆ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C _A substituted or unsubstituted C ₁ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-direction The condensed polycyclic groups, and substituted or unsubstituted 1, a non-aromatic heterocyclic is selected from the condensed polycyclic group;
R ₂₁ to R ₂₃ may optionally be connected to form a ring;
a21 and a22 are independently selected from 1, 2, 3, and 4; 17. The method of claim 16,
Wherein the weight ratio of the electron transporting material to the alkali metal complex is from 10:90 to 90:10. The method according to claim 1,
Wherein the electron transporting region includes an electron transporting layer, and the electron transporting material is contained in the electron transporting layer. 20. The method of claim 19,
Wherein the electron transport layer further comprises an alkali metal complex.

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