KR20170024545A - Organometallic compound and organic light-emitting device including the same - Google Patents

Abstract

Disclosed are an organometallic compound represented by chemical formula 1, and an organic light-emitting device including the organometallic compound. According to the present invention, the organometallic compound exhibits excellent electrical properties and thermal stability.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent device,

Embodiments of the present invention relate to organometallic compounds and organic light emitting devices containing them.

The organic light emitting device is a self light emitting type device having a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed characteristics, and multi-coloring.

According to an example, the organic light emitting element may include an anode, a cathode, and an organic layer interposed between the anode and the cathode and including a light emitting layer. A hole transporting region may be provided between the anode and the light emitting layer, and an electron transporting region may be provided between the light emitting layer and the cathode. The holes injected from the anode move to the light emitting layer via the hole transporting region, and electrons injected from the cathode move to the light emitting layer via the electron transporting region. The holes and electrons recombine in the light emitting layer region to generate excitons. This exciton changes from the excited state to the ground state and light is generated.

Embodiments of the present invention provide an organic metal compound and an organic light emitting device including the organic metal compound.

One embodiment of the present invention discloses an organometallic compound represented by the following Formula 1:

≪ Formula 1 >

In Formula 1,

M is Os or Ru;

R ₁₁ to R ₁₃ and R ₁₆ independently of each other represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl 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 1, a non-condensed polycyclic aromatic group and a substituted or At least one of R ₁₁ to R ₁₃ and R ₁₆ is selected from the group consisting of a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₇ -C ₁₂ aryl group, Substituted or unsubstituted C ₁ -C ₆₀ arylalkyl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryloxy group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylthio group, unsubstituted C ₂ -C ₆₀ heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic Selected from the interrogating condensed polycyclic group, and;

R ₁₄ and R ₁₅ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group and is selected from substituted or unsubstituted C ₆ -C ₆₀ aryl group;

n is selected from 1, 2, and 3;

L ₁₁ is selected from a monodentate ligand and a bidentate ligand;

m is selected from 0, 1, 2, 3 and 4.

Another embodiment of the present invention is directed to a liquid crystal display comprising: a first electrode; A second electrode; And an organic layer including a light emitting layer interposed between the first electrode and the second electrode, wherein the organic layer includes at least one organometallic compound represented by Formula 1.

The organic metal compound has excellent electrical characteristics and thermal stability. The organic light emitting device employing the organic metal compound has excellent efficiency, excellent external quantum efficiency, low driving voltage, high brightness, long life time characteristics and low roll-off characteristics .

1 is a schematic view illustrating a structure of an organic light emitting diode according to an embodiment of the present invention.
FIG. 2 is a diagram showing the photoluminescence (PL) spectra of the compounds 1 and 3. FIG.
FIG. 3 is a graph showing a thermal gravimetric analysis (TGA) of Compound 3. 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. However, the present invention is not limited to the embodiments described below, but may be implemented in various forms.

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

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

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

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

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

In the present specification, the 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.

The organometallic compound is represented by the following Formula 1:

≪ Formula 1 >

In the above formula (1), M may be Os or Ru.

In Formula 1, R ₁₁ to R ₁₃ and R ₁₆ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, Or an unsubstituted C ₃ -C ₁₀ cycloalkyl 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 condensation A polycyclic group, and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group, provided that at least one of R ₁₁ to R ₁₃ and R ₁₆ is a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a C ₇ -C ₆₀ arylalkyl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryloxy group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl, thio group, a substituted or unsubstituted C ₂ -C ₆₀ heteroarylalkyl group, a substituted or unsubstituted 1, a non-condensed polycyclic aromatic group and a substituted or unsubstituted It may be selected from aromatic heterocyclic condensed polycyclic group, - one non-

In one embodiment, R ₁₁ , R ₁₂ , R _13, or R ₁₆ in Formula 1 is 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 monovalent non-aromatic heterocyclic polycyclic group.

For example, in the above formula (1), R ₁₁ represents 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 condensation R ₁₂ , R ₁₃ and R ₁₆ independently of one another are selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, A cyano group, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, and a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group;

R ₁₂ is 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 a non-aromatic heterocyclic is selected from a condensed polycyclic group, R _11, R ₁₃ and R ₁₆ are independently selected from hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, a cyano group, a substituted or unsubstituted C together ₁ -C ₆₀ alkyl group and selected from substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, or;

R ₁₃ is 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 a non-aromatic heterocyclic is selected from a condensed polycyclic group, R _11, R ₁₂ and R ₁₆ are independently selected from hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, a cyano group, a substituted or unsubstituted C together ₁ -C ₆₀ alkyl group and selected from substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, or;

R ₁₆ is 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 Aromatic heterocyclic polycyclic groups and R ₁₁ to R ₁₃ are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C ₁ -C ₆₀ alkyl group and may be selected from substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, and the like.

In another embodiment, R _11, R _12, R ₁₃ and R ₁₆ 2 of the substituents are, independently of each other, substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl But are not limited to, aryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, and substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic groups.

For example, in the above formula (1), R ₁₁ and R ₁₆ independently represent a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, Aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group, and R ₁₂ and R ₁₃ independently of one another are selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br , -I, a cyano group, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group and a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group;

R ₁₁ and R ₁₂ independently represent 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 monovalent non-aromatic heterocyclic polycyclic group R ₁₃ and R ₁₆ are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, An unsubstituted C ₁ -C ₆₀ alkyl group and a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group;

R ₁₁ and R ₁₃ independently of each other represent 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 monovalent non-aromatic heterocyclic polycyclic group R ₁₂ and R ₁₆ are independently of each other selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, An unsubstituted C ₁ -C ₆₀ alkyl group and a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group;

R ₁₂ and R ₁₆ are, independently of each other, 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 monovalent non-aromatic heterocyclic polycyclic group R ₁₁ and R ₁₃ are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, An unsubstituted C ₁ -C ₆₀ alkyl group and a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group;

R ₁₃ and R ₁₆ are, independently of each other, 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 monovalent non-aromatic heterocyclic polycyclic group R ₁₁ and R ₁₂ are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, An unsubstituted C ₁ -C ₆₀ alkyl group and a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group;

R ₁₂ and R ₁₃ are, independently of each other, 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 monovalent non-aromatic heterocyclic polycyclic group R ₁₁ and R ₁₆ are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, An unsubstituted C ₁ -C ₆₀ alkyl group and a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, but is not limited thereto.

In still another embodiment, the three substituents of R ₁₁ , R ₁₂ , R ₁₃ and R ₁₆ are, independently of each other, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ A substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group.

For example, in the above formula (1), R ₁₁ , R ₁₂ and R ₁₆ independently represent a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted Or an unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group; R ₁₃ is selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C ₁ -C ₆₀ alkyl group and substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group;

R ₁₁ , R ₁₃ and R ₁₆ independently of one another are 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 A condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group; R ₁₂ is selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C ₁ -C ₆₀ alkyl group and substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group;

R ₁₁ to R ₁₃ independently represent 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 substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic groups; R ₁₆ is selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C ₁ -C ₆₀ alkyl group and substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group;

R ₁₂ , R ₁₃ and R ₁₆ each independently represent 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 A condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group; R ₁₁ can be selected from among hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C ₁ -C ₆₀ alkyl groups and substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl groups However, the present invention is not limited thereto.

In yet another embodiment, R ₁₁ , R ₁₂ , R ₁₃ and R ₁₆ are, independently of each other, 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 monovalent non-aromatic heterocyclic polycyclic group.

In one embodiment, R ₁₁ to R ₁₃ and R ₁₆ in the general formula (1) are independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, An iso-propyl group, a n-butyl group, an iso-butyl group, a sec-butyl group, a tert- A t-butyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group;

An isopropyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, an isopropyl group, a n-butyl group, , tert-butyl group, n-pentyl group, iso-pentyl group, sec-pentyl group, tert-pentyl group and neo-pentyl group; -

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, , a cyclopentyl group, a cyclohexyl group and a cycloheptyl group substituted with at least one of n-pentyl group, iso-pentyl group, sec-pentyl group, tert-pentyl group and neo-pentyl group;

A thiazolyl group, a thiazolyl group, an oxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, A benzothiophenyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophene group such as a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a naphthyridinyl group, A phenyl group; And

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, An amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or its salt, a sulfonic acid or its salt, a phosphoric acid or its salt, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, di group, pyrazinyl group, pyrimidinyl group, triazinyl group and a _{-Si (Q 1) (Q 2} ) (Q 3) of the at least one substituted phenyl group, a naphthyl group, phenanthrenyl group, anthracenyl group, pie les A thiophene group, a thiazolyl group, an oxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolyl group, A thienyl group, a norbornyl group, a quinoxalinyl group, a quinazolinyl group, a naphthyridinyl group, a benzofuranyl group, a benzothiophenyl group, a triazinyl group, a dibenzofuranyl group and a dibenzothiophenyl group; ≪ / RTI >

At least one of R ₁₁ to R ₁₃ and R ₁₆ is a phenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klychenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, A benzofuranyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, Triazinyl group, dibenzofuranyl group and dibenzothiophenyl group; And

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, An amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or its salt, a sulfonic acid or its salt, a phosphoric acid or its salt, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, di group, pyrazinyl group, pyrimidinyl group, triazinyl group and a _{-Si (Q 1) (Q 2} ) (Q 3) of the at least one substituted phenyl group, a naphthyl group, phenanthrenyl group, anthracenyl group, pie les A thiophene group, a thiazolyl group, an oxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolyl group, A thienyl group, a norbornyl group, a quinoxalinyl group, a quinazolinyl group, a naphthyridinyl group, a benzofuranyl group, a benzothiophenyl group, a triazinyl group, a dibenzofuranyl group and a dibenzothiophenyl group; ≪ / RTI >

Q ₁ to Q ₃ may be independently selected from a C ₁ -C ₂₀ alkyl group and a C ₆ -C ₆₀ aryl group.

In another embodiment, R ₁₁ to R ₁₃ and R ₁₆ in Formula 1 are independently selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, a sec-butyl group, a tert-butyl group, a cyclopentyl group and a cyclohexyl group;

An isopropyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, an isopropyl group, a n-butyl group, And tert-butyl groups;

A cyclopentyl group and a cyclohexyl group substituted with at least one of deuterium, -F, -Cl, -Br, -I, cyano group, methyl group and ethyl group;

A phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; And

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a cyano group, a methyl group, ethyl group, n- propyl Propyl group, n-butyl group, isopropyl group, n-butyl group, iso-butyl group, sec- a phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group which are substituted with at least one of -Si (CH ₃ ) ₃ , a tert-butoxy group, a phenyl group and -Si (CH ₃ ) ₃ ; ≪ / RTI >

At least one of R ₁₁ to R ₁₃ and R ₁₆ is a phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; And

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a cyano group, a methyl group, ethyl group, n- propyl Propyl group, n-butyl group, isopropyl group, n-butyl group, iso-butyl group, sec- a phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group which are substituted with at least one of -Si (CH ₃ ) ₃ , a tert-butoxy group, a phenyl group and -Si (CH ₃ ) ₃ ; , But is not limited thereto.

In still another embodiment, R ₁₁ to R ₁₃ in the general formula (1) are independently selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, A butyl group, a tert-butyl group, a cyclopentyl group, and a cyclohexyl group;

An isopropyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, an isopropyl group, a n-butyl group, And tert-butyl groups;

A cyclopentyl group and a cyclohexyl group substituted with at least one of deuterium, -F, -Cl, -Br, -I, cyano group, methyl group and ethyl group;

A phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; And

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a cyano group, a methyl group, ethyl group, n- propyl Propyl group, n-butyl group, isopropyl group, n-butyl group, iso-butyl group, sec- a phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group which are substituted with at least one of -Si (CH ₃ ) ₃ , a tert-butoxy group, a phenyl group and -Si (CH ₃ ) ₃ ; ≪ / RTI >

R ₁₆ represents a phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; And

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a cyano group, a methyl group, ethyl group, n- propyl Propyl group, n-butyl group, isopropyl group, n-butyl group, iso-butyl group, sec- a phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group which are substituted with at least one of -Si (CH ₃ ) ₃ , a tert-butoxy group, a phenyl group and -Si (CH ₃ ) ₃ ; , But is not limited thereto.

In another embodiment, R ₁₁ , R ₁₃ and R ₁₆ in the general formula (1) are independently selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, , sec-butyl group, tert-butyl group, cyclopentyl group and cyclohexyl group;

An isopropyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, an isopropyl group, a n-butyl group, And tert-butyl groups;

A cyclopentyl group and a cyclohexyl group substituted with at least one of deuterium, -F, -Cl, -Br, -I, cyano group, methyl group and ethyl group;

A phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; And

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a cyano group, a methyl group, ethyl group, n- propyl Propyl group, n-butyl group, isopropyl group, n-butyl group, iso-butyl group, sec- a phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group which are substituted with at least one of -Si (CH ₃ ) ₃ , a tert-butoxy group, a phenyl group and -Si (CH ₃ ) ₃ ; ≪ / RTI >

R ₁₂ represents a phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; And

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a cyano group, a methyl group, ethyl group, n- propyl Propyl group, n-butyl group, isopropyl group, n-butyl group, iso-butyl group, sec- a phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group which are substituted with at least one of -Si (CH ₃ ) ₃ , a tert-butoxy group, a phenyl group and -Si (CH ₃ ) ₃ ; , But is not limited thereto.

In Formula 1, R ₁₄ and R ₁₅ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, A substituted C ₃ -C ₁₀ cycloalkyl group and a substituted or unsubstituted C ₆ -C ₆₀ aryl group.

For example, in Formula 1, R ₁₄ and R ₁₅ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, A n-pentyl group, a sec-pentyl group, a tert-pentyl group, a neopentyl group, a cyclopentyl group, an iso-butyl group, , A cyclohexyl group, a cycloheptyl group, a phenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a klycenyl group;

An isopropyl group, an n-butyl group, an iso-butyl group, a sec-butyl group and a tert-butyl group substituted with at least one of deuterium, -F, -Cl, -Br and -I, Butyl group, n-pentyl group, iso-pentyl group, sec-pentyl group, tert-pentyl group and neo-pentyl group; And

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, , a cyclohexyl group, a cycloheptyl group, a phenyl group, a naphthyl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, Anthracenyl group, pyrenyl group, and chrysenyl group; , But is not limited thereto.

As another example, in the general formula (1), R ₁₄ and R ₁₅ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, An n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a cyclopentyl group, a cyclohexyl group, a phenyl group and a naphthyl group; And

N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl groups substituted with at least one of hydrogen, , But is not limited thereto.

As another example, in the above formula (1), R ₁₄ and R ₁₅ independently represent hydrogen, deuterium, -F, cyano, methyl, ethyl, n-propyl, isopropyl, -Butyl group, a tert-butyl group, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ and phenyl groups. It is not.

As another example, in Formula 1, R ₁₄ is hydrogen, and R ₁₅ is -F, cyano, methyl, ethyl, n-propyl, iso-propyl, -Butyl group, tert-butyl group, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ and phenyl group.

As another example, in Formula 1, R ₁₅ is hydrogen, and R ₁₄ is -F, cyano, methyl, ethyl, n-propyl, isopropyl, -Butyl group, tert-butyl group, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ and phenyl group.

As another example, in the general formula (1), R ₁₄ and R ₁₅ independently represent -F, cyano, methyl, ethyl, n-propyl, isopropyl, but are not limited to, a sec-butyl group, a tert-butyl group, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ and a phenyl group.

로 표시되는 리간드의 개수를 의미하며, 여기서 * 및 *'은 상기 화학식 1 중 M과의 결합 사이트이다. 상기 화학식 1 중, n은 1, 2 및 3 중에서 선택될 수 있고, n이 2 이상이면 복수개의 상기 리간드는 서로 동일하거나 상이할 수 있다.In the above formula (1), n is

Where * and * are binding sites for M in the above formula (1). In Formula 1, n may be selected from 1, 2, and 3, and when n is 2 or more, a plurality of the ligands may be the same or different from each other.

For example, in Formula 1, n may be 2, but is not limited thereto.

In the above formula (1), L ₁₁ may be selected from a monodentate ligand and a bidentate ligand.

Examples of the one-site ligands include iodide ion, bromide ion, chloride ion, sulfide, thiocyanate ion, nitrate ion, azide ion, hydroxide ion, cyanide ion, isocyanide ion, water, acetonitrile, pyridine, But are not limited to, carbene, ammonia, carbon monoxide, PPh ₃ , PPh ₂ CH ₃ , PPh (CH ₃ ) ₂ and P (CH ₃ ) ₃ .

Examples of such bidentate ligands include, but are not limited to, ovalate ions, acetylacetonate, picolinic acid, 2- (2-hydroxyphenyl) -pyridine, 2- phenylpyridine, 1,2- bis (diphenylphosphino) dppe), 1,1-bis (diphenylphosphino) methane (dppm), glycinate, ethylenediamine, 2,2'-bipyridine, 1,10-phenanthroline, It is not.

For example, in the above formula (1), L ₁₁ may be a ligand represented by any one of the following formulas (2-1) to (2-12), but is not limited thereto:

Of the above-mentioned formulas (2-1) to (2-12)

A ₂₁ and A ₂₂ are independently from each other selected from C ₅ -C ₂₀ carbocyclic groups and C ₁ -C ₂₀ heterocyclic groups;

X ₂₁ , X ₂₂ , X ₂₈ and X ₂₉ are independently of each other selected from C and N;

X ₂₃ is N or C (Q ₂₃ ); X ₂₄ is N or C (Q ₂₄ ); X ₂₅ is N or C (Q ₂₅ ); X ₂₆ is N or C (Q ₂₆ ); X ₂₇ is N or C (Q ₂₇ );

X ₂₈ is O, S or N (Q ₂₈ ); X ₂₉ is O, S or N (Q ₂₉ );

Y ₂₁ and Y ₂₂ are, independently of each other, a single bond, a double bond, a substituted or unsubstituted C ₁ -C ₅ alkylene group, a substituted or unsubstituted C ₂ -C ₅ alkenylene group and a substituted or unsubstituted C ₆ It is selected from -C ₁₀ arylene group;

Z ₂₁ and Z ₂₂ are independently from each other selected from N, O, N (R ₂₅ ), P (R ₂₅ ) (R ₂₆ ) and As (R ₂₅ ) (R ₂₆ );

Z ₂₃ is selected from P and As;

Z ₂₄ is selected from CO and CH ₂ ;

R ₂₁ to R ₃₀ and Q ₂₃ to Q ₂₉ are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, , Substituted or unsubstituted C ₁ -C ₆₀ alkyl groups, substituted or unsubstituted C ₂ -C ₆₀ alkenyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted aryl groups, 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 aryl come tea, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent A non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group; ; R ₂₁ and R ₂₂ may be optionally combined to form a ring; R ₂₇ and R ₂₈ may be optionally combined to form a ring; R ₂₈ and R ₂₉ may be optionally combined to form a ring; R ₂₉ and R ₃₀ may be optionally combined to form a ring;

b21 and b22 are independently of each other selected from 1, 2 and 3;

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

For example, in formula (2-1), A ₂₁ and A ₂₂ independently represent a benzene group, a naphthalene group, an imidazole group, a benzimidazole group, a pyridine group, a pyrimidine group, a triazine group, a quinoline group, Isoquinoline group, but is not limited thereto.

For example, in Formula 2-1, X ₂₂ and X ₂₉ may be N, but are not limited thereto.

For example, in Formula 2-7, X ₂₃ is C (Q ₂₃ ); X ₂₄ is C (Q ₂₄ ); X ₂₅ is C (Q ₂₅ ); X ₂₆ is C (Q ₂₆ ); X ₂₇ may be C (Q ₂₇ ), but is not limited thereto.

For example, in Formula 2-8, X ₂₈ is N (Q ₂₈ ); X ₂₉ may be N (Q ₂₉ ), but is not limited thereto.

For example, in the general formulas (2-2), (2-3) and (2-8), Y ₂₁ and Y ₂₂ may be independently selected from a substituted or unsubstituted methylene group and a substituted or unsubstituted phenylene group, But is not limited thereto.

For example, in the general formulas (2-1) and (2-2), Z ₂₁ and Z ₂₂ may be O, but are not limited thereto.

For example, in Formula 2-4, Z ₂₃ may be P, but is not limited thereto.

For example, in formulas (2-1) to (2-8), R ₂₁ to R ₃₀ and Q ₂₃ to Q ₂₉ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, , 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, a phosphoric acid group or a salt thereof, 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 C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group;

A phenyl group, a pyranyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, an imidazolyl group, an imidazolyl group, a pyrazolyl group, A pyridinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, an isothiazolyl group, an isothiazolyl group, an isothiazolyl group, an isoxazolyl group, A quinolinyl group, a quinolizinyl group, a quinazolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazole group, a benzoquinolyl group, a benzoquinolinyl group, A thiazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranoyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazole group, a benzoxazolyl group, Diazo and imidazopyridinyl groups; And

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, An amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or its salt, a sulfonic acid or its salt, a phosphoric acid or its salt, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, A pyranyl 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 imidazolyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, A benzoquinolinyl group, a quinazolinyl group, a cyano group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, A thiazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a benzo thiophenyl group, a benzothiophenyl group, a benzothiophene group, Naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group which is substituted with at least one of divalent group, dibenzocarbazolyl group and imidazopyridinyl group, A thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl 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 quinoxalinyl group, a quinazolinyl group, A phenanthrolinyl 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 triazinyl group, a dibenzofurano group, A phenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group and an imidazopyridinyl group; , But is not limited thereto.

As another example, in the above formula (1), L ₁₁ may be a ligand represented by any one of the following formulas (3-1) to (3-25), but is not limited thereto:

Of the above formulas (3-1) to (3-25)

Ph is a phenyl group;

Ph-d < ₅ > is a phenyl group in which all hydrogen is substituted with deuterium;

* And * are binding sites with neighboring atoms.

In the formula (1), m represents the number of L ₁₁ , and m may be selected from 0, 1, 2, 3 and 4. When m is 2 or more, plural L < ₁₁ > may be the same or different from each other.

For example, in Formula 1, m may be selected from 1 and 2, but is not limited thereto.

For example, the organometallic compound represented by Formula 1 may be a heteroleptic or a homoleptic organometallic compound, but is not limited thereto.

For example, in the above formula (1), n is 2 and m is 2, but is not limited thereto.

For example, in the above formula (1), n is 2 and m is 1, but is not limited thereto.

In one embodiment, in Formula 1, M is Os or Ru;

R ₁₁ to R ₁₃ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₃ -C _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 ₁₆ is 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 ₁₄ and R ₁₅ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group and is selected from substituted or unsubstituted C ₆ -C ₆₀ aryl group;

n is selected from 1, 2, and 3;

L ₁₁ is selected from a monodentate ligand and a bidentate ligand;

m may be selected from 0, 1, 2, 3 and 4, but is not limited thereto.

In another embodiment, the organometallic compound represented by Formula 1 may be represented by any one of the following Formulas 1-1 to 1-9, but is not limited thereto:

Among the above formulas 1-1 to 1-9,

M, R ₁₂ to R ₁₅ , n, L ₁₁ and m are as defined in Formula 1,

Ar ₁₁ is 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,

Provided that R ₁₂ to R ₁₅ are not each hydrogen.

The organometallic compound represented by Formula 1 may be represented by any one of the following Formulas 1-11 to 1-19 and 1-21 to 1-29, but is not limited thereto:

Of the above formulas 1-11 to 1-19 and 1-21 to 1-29,

L < ₁₁ > and m are as defined in formula (1) above;

Ar _11a and Ar _11b independently represent 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 substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic groups;

R _12a and R _12b independently of one another refer to the definition of R _{12 in} the above formula (1);

R _13a and R _13b independently of one another refer to the definition of R _{13 in} the above formula (1);

R _14a and R _14b independently of one another refer to the definition of R ₁₄ in Formula 1 above;

R _15a and R _15b independently of one another refer to the definition of R ₁₅ in Formula 1 above;

L < ₁₂ > refers to the definition of L < ₁₁ > in the above formula (1)

Provided that R ₁₂ to R ₁₅ are not each hydrogen.

The organometallic compound represented by Formula 1 may be selected from the following compounds 1 to 176, but is not limited thereto:

The organometallic compound represented by Formula 1 may be substituted with an aryl group or the like to the pyridine ring to improve the electrical, chemical and / or physical stability of the pyridine ring. In addition, the organometallic compound represented by the general formula (1) includes an aryl group and the like, so that hole mobility can be improved. Therefore, the lifetime and efficiency of the organic light emitting device including the organometallic compound represented by Formula 1 may be improved.

The organometallic compound represented by Formula 1 is substituted by an aryl group or the like in the pyridine ring, and thus the planarity of the organometallic compound represented by Formula 1 may be lowered. Therefore, aggregation of the organometallic compound represented by Formula 1 may be reduced, and the efficiency of the organic light emitting device including the organometallic compound may be improved.

Since the organometallic compound represented by Formula 1 includes Os or Ru, it may have an octahedral structure. Compounds having such an octahedral structure may have a shorter damping time than compounds having a square planar structure (for example, an organometallic compound containing Pt). In addition, the organometallic compound represented by Formula 1 has less exciton quenching and triplet-triplet annihilation can be reduced, so that the organic light emitting device including the organometallic compound has a high efficiency, Lt; / RTI >

For example, the results of simulations using Gaussian for HOMO, LUMO and T ₁ energy levels for some of the above compounds and Compound B are shown in Table 1 below:

Compound No. HOMO (eV) LUMO (eV) T ₁ (eV) One -4.548 -1.367 2.309 3 -4.569 -1.348 2.330 9 -4.571 -1.316 2.355 7 -4.580 -1.509 2.210 B -4.522 -1.317 2.304

The method for synthesizing the organometallic compound represented by the above formula (1) can be recognized by those skilled in the art with reference to the following synthesis examples.

Accordingly, the organic metal compound represented by Formula 1 may be suitable for use as an organic layer of an organic light emitting device, for example, as a dopant of a light emitting layer in the organic layer. According to another aspect of the present invention, A second electrode; And an organic layer interposed between the first electrode and the second electrode, the organic layer including a light-emitting layer and containing at least one or more organic metal compounds represented by the general formula (1).

The organometallic compound represented by Formula 1 may be used between a pair of electrodes of an organic light emitting device. For example, the organic metal compound represented by Formula 1 may be included in the light emitting layer. In this case, the organic metal compound serves as a dopant, and the light emitting layer may further include a host (i.e., the content of the organometallic compound represented by Formula 1 is smaller than the content of the host).

In the present specification, the phrase "(organic layer) contains at least one organometallic compound" means that "(organic layer) contains one organometallic compound belonging to the category of the above formula (1) Or more of the organic metal compound ".

For example, the organic layer may contain only the compound 1 as the organometallic compound. At this time, the compound 1 may exist in the light emitting layer of the organic light emitting device. Alternatively, the organic layer may include the compound 1 and the compound 2 as the organometallic compound. At this time, the compound 1 and the compound 2 are present in the same layer (for example, both the compound 1 and the compound 2 may exist in the light emitting layer).

The first electrode is a cathode which is a hole injection electrode and the second electrode is a cathode which is an electron injection electrode, or the first electrode is a cathode which is an electron injection electrode and the second electrode is an electron hole injection electrode.

For example, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may include i) at least one of a hole injecting layer, a hole transporting layer, and an electron blocking layer interposed between the first electrode and the light emitting layer A hole transport region including one; And ii) an electron transporting region interposed between the light emitting layer and the second electrode, the electron transporting region including at least one of a hole blocking layer, an electron transporting layer, and an electron injection layer.

1 schematically shows a cross-sectional view of an organic light emitting device 10 according to an embodiment of the present invention. 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. The organic light emitting diode 10 has a structure in which the first electrode 11, the organic layer 15, and the second electrode 19 are sequentially stacked.

A substrate may further be disposed below the first electrode 11 or above the second electrode 19. As the substrate, a substrate used in a conventional organic light emitting device can be used. A glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness can be used.

The first electrode 11 can be formed, for example, by providing a first electrode material on the substrate using a deposition method, a sputtering method, or the like. The first electrode 11 may be an anode. The first electrode material may be selected from materials having a high work function to facilitate hole injection. The first electrode 11 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 can be used. Alternatively, a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium- .

The first electrode 11 may have a single layer or a multilayer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but the present invention is not limited thereto.

An organic layer 15 is disposed on the first electrode 11.

The organic layer 15 may include a hole transport region; An emission layer; And an electron transport region.

The hole transporting region may be disposed between the first electrode 11 and the light emitting layer.

The hole transporting region may include at least one of a hole injecting layer, a hole transporting layer, an electron blocking layer, and a buffer layer.

The hole transporting region may include only a hole injecting layer, or may include only a hole transporting layer. Alternatively, the hole transporting region may have a structure of a hole injecting layer / a hole transporting layer or a hole injecting layer / a hole transporting layer / an electron blocking layer which are sequentially stacked from the first electrode 11.

When the hole transporting region includes a hole injecting layer, the hole injecting layer (HIL) may be formed on the first electrode 11 by various methods such as a vacuum deposition method, a spin coating method, a casting method, an LB method, have.

When the hole injection layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the hole injection layer material, the structure and thermal properties of the desired hole injection layer, and the like. For example, 500 ° C, a degree of vacuum of about 10 ^-8 to about 10 ^-3 torr, and a deposition rate of about 0.01 to about 100 Å / sec.

When the hole injection layer is formed by the spin coating method, the coating conditions vary depending on the structure and thermal properties of the compound used as the hole injection layer material, the desired hole injection layer, and the coating speed of about 2000 rpm to about 5000 rpm, The heat treatment temperature for removing the solvent after coating may be selected from the range of about 80 캜 to 200 캜, but is not limited thereto.

The conditions for forming the hole transporting layer and the electron blocking layer refer to conditions for forming the hole injection layer.

NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, TCTA (4,4 ', 2'- , 4 "-tris (N-carbazolyl) triphenylamine), Pani / DBSA (polyaniline / dodecylbenzenesulfonic acid: polyaniline / dodecylbenzenesulfonic acid) Poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate) / poly (4-styrene sulfonate), Pani / CSA (Polyaniline / Camphor sulfonicacid (Polyaniline / camphorsulfonic acid), PANI / PSS (polyaniline) / poly (4-styrenesulfonate): polyaniline) / poly (4-styrenesulfonate)), the compound represented by Chemical Formula 201 and the compound represented by Chemical Formula 202 And may include at least one:

≪ Formula 201 >

≪ EMI ID =

In the above formula (201), Ar ₁₀₁ and Ar ₁₀₂ , independently of each other,

A phenanthrenyl group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, A phenylene group, a phenylene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, And

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, 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 ₃ -C ₁₀ cycloalkenyl group , C ₁ -C ₁₀ heterocycloalkyl 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 hetero aryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is non-inde aromatic heterocyclic condensed polycyclic group with at least one substituted phenyl group, a penta-alkylenyl group wherein carbonyl group, a naphthyl group, an azulenyl group, a heptal A phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a cyano group, a phenanthrene group, Carbonyl alkylenyl group, a hexenyl group naphtha, blood hexenyl group, a perylenyl group and a carbonyl penta hexenyl groups; ≪ / RTI >

In Formula 201, xa and xb may be independently an integer of 0 to 5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0, but is not limited thereto.

In Formulas 201 and 202, R ₁₀₁ to R ₁₀₈ , R ₁₁₁ to R _119, and R ₁₂₁ to R ₁₂₄ are, independently of each other,

A halogen atom, a hydroxyl group, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₁₀ alkyl group (e.g., methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, etc.) and C ₁ -C ₁₀ alkoxy group (e.g., methoxy, ethoxy Propoxy group, butoxy group, pentoxy group, etc.);

A sulfonic acid or a salt thereof and a phosphoric acid or a sulfonic acid or a salt thereof, or a salt thereof, or a salt thereof, A C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group substituted with one or more of the salts thereof;

A phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group; And

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group substituted with at least one of a salt thereof, a C ₁ -C ₁₀ alkyl group, and a C ₁ -C ₁₀ alkoxy group; , But is not limited thereto.

In the above formula (201), R < ₁₀₉ &

A phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group; And

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A naphthyl group, an anthracenyl group and a pyridinyl group substituted with at least one of a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group and a pyridinyl group; ≪ / RTI >

According to one embodiment, the compound represented by Formula 201 may be represented by Formula 201A below, but is not limited thereto:

≪ Formula 201A >

In the above formula (201A), R ₁₀₁ , R ₁₁₁ , R ₁₁₂ and R ₁₀₉ are described in detail above.

For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include, but are not limited to, the following compounds HT1 to HT20:

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-tetracano-1,4-benzoquinone di Quinone derivatives such as phosphorus (F4-TCNQ); Metal oxides such as tungsten oxide and molybdenum oxide; And cyano group-containing compounds such as the following compounds HT-D1 and the like, but are not limited thereto.

<Compound HT-D1> <F4-TCNQ>

The hole transporting region may further include a buffer layer.

The buffer layer may serve to increase the efficiency by compensating the optical resonance distance according to the wavelength of the light emitted from the light emitting layer.

A light emitting layer (EML) may be formed on the hole transporting region by a method such as a vacuum evaporation method, a spin coating method, a casting method, or an LB method. In the case of forming the light emitting layer by the vacuum deposition method and the spin coating method, the deposition conditions and the coating conditions vary depending on the compound used, but generally, the conditions can be selected from substantially the same range as the formation of the hole injection layer.

Meanwhile, when the hole transporting region includes an electron blocking layer, the electron blocking layer material may be selected from a material that can be used in the hole transporting region as described above and a host material described below, but is not limited thereto . For example, when the hole transporting region includes an electron blocking layer, mCP described later can be used as the electron blocking layer material.

The light emitting layer may include a host and a dopant, and the dopant may include an organometallic compound represented by the general formula (1).

The host may comprise at least one of the following TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, Mcp,

<mCP> <Compound H50> <Compound H51>

Alternatively, the host may further comprise a compound represented by Formula 301:

&Lt; Formula 301 >

In Formula 301, Ar ₁₁₁ and Ar ₁₁₂ are, independently from each other,

A phenylene group, a naphthylene group, a phenanthrenylene group and a pyrenylene group; And

A phenylene group, a naphthylene group, a phenanthrenylene group and a pyrenylene group which are substituted with at least one of a phenyl group, a naphthyl group and an anthracenyl group; &Lt; / RTI &gt;

In Formula 301, each of Ar ₁₁₃ to Ar ₁₁₆ independently represents,

A C ₁ -C ₁₀ alkyl group, a phenyl group, a naphthyl group, a phenanthrenyl group and a pyrenyl group; And

A phenyl group, a naphthyl group, a phenanthrenyl group and a pyrenyl group substituted with at least one of a phenyl group, a naphthyl group and an anthracenyl group; &Lt; / RTI &gt;

G, h, i, and j in Formula 301 may be independently an integer of 0 to 4, for example, 0, 1, or 2.

In Formula 301, Ar ₁₁₃ to Ar ₁₁₆ independently represent,

A C ₁ -C ₁₀ alkyl group substituted by at least one of a phenyl group, a naphthyl group and an anthracenyl group;

A phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group and a fluorenyl group;

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, 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 phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group A phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group and a fluorenyl group which are substituted with at least one of a fluorenyl group and a fluorenyl group; And

; 중에서 선택될 수 있으나, 이에 한정되는 것은 아니다.

; , But is not limited thereto.

Alternatively, the host may comprise a compound represented by Formula 302:

&Lt; Formula 302 >

For details of Ar ₁₂₂ to Ar ₁₂₅ in the above formula (302), see the description of Ar ₁₁₃ in the above formula (301).

Ar ₁₂₆ and Ar ₁₂₇ in the formula (302) may be, independently of each other, a C ₁ -C ₁₀ alkyl group (for example, a methyl group, an ethyl group or a propyl group).

And k and l in Formula 302 may be independently an integer of 0 to 4. For example, k and l may be 0, 1 or 2.

The compound represented by Formula 301 and the compound represented by Formula 302 may include the following compounds H1 to H42, but are not limited thereto.

When the organic light emitting device is a full color organic light emitting device, the light emitting layer may be patterned as a red light emitting layer, a green light emitting layer, and a blue light emitting layer. Alternatively, the light emitting layer may have a structure in which a red light emitting layer, a green light emitting layer, and / or a blue light emitting layer are stacked to emit white light.

When the light emitting layer includes a host and a dopant, the dopant 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 is disposed above the light emitting layer.

The electron transporting region may include at least one of a hole blocking layer, an electron transporting layer, and an electron injection layer.

For example, the electron transporting region may have a structure of a hole blocking layer / electron transporting layer / electron injecting layer or electron transporting layer / electron injecting layer, but is not limited thereto. The electron transporting layer may have a single layer or a multi-layer structure including two or more different materials.

The forming conditions of the hole blocking layer, the electron transporting layer and the electron injecting layer in the electron transporting region refer to the forming conditions of the hole injecting layer.

When the electron transport region includes a hole blocking layer, the hole blocking layer may include, but is not limited to, at least one of BCP, Bphen, and Balq.

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

Alternatively, the electron transporting layer may include at least one of the following compounds ET1 and ET2, but is not limited thereto.

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

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

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

The electron transport region may also include an electron injection layer (EIL) that facilitates the injection of electrons from the second electrode 19.

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

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.

A second electrode 19 is formed on the organic layer 15. The second electrode 19 may be a cathode. As the material for the second electrode 19, a metal, an alloy, an electrically conductive compound having a relatively low work function, or a combination thereof may be used. Specific examples thereof include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium- And may be used as a material for forming the second electrode 19. Alternatively, the transmissive second electrode 19 can be formed using ITO or IZO to obtain a front light emitting element.

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 C ₆ -C ₆₀ aryl group. In the present specification, the C ₇ -C ₆₀ arylalkyl group refers to -A ₁₀₄ A ₁₀₅ (wherein A ₁₀₅ is the C ₆ -C ₅₉ aryl group and A ₁₀₄ is the C ₁ -C ₅₄ alkylene group).

In the specification C ₁ -C ₆₀ heteroaryloxy group -OA ₁₀₆ (wherein, A ₁₀₆ is a C ₁ -C ₆₀ heteroaryl group), point a, the specification of the C ₁ -C ₆₀ heteroaryl thio groups -SA ₁₀₇ ( Wherein A ₁₀₇ is the above C ₁ -C ₆₀ heteroaryl group, and the C ₂ -C ₆₀ heteroarylalkyl group in this specification is -A ₁₀₈ A ₁₀₉ wherein A ₁₀₉ is the above C ₁ -C ₅₉ heteroaryl group And A ₁₀₈ is the above C ₁ -C ₅₉ alkylene group.

In the present specification, a monovalent non-aromatic condensed polycyclic group is a monovalent aromatic condensed polycyclic group in which two or more rings are condensed with each other and contain only carbon as a ring-forming atom and the whole molecule is non-aromatic. (E. G., Having from 8 to 60 carbon atoms). Examples of the monovalent 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.

In the present specification, a monovalent non-aromatic condensed heteropolycyclic group is a monovalent aromatic condensed heteropolycyclic group in which two or more rings are condensed with each other and contain heteroatoms selected from N, O, P and S in addition to carbon as a ring- , And the whole molecule is a monovalent group (for example, having a carbon number of 1 to 60) having 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 ₁ -C ₆₀ alkyl group, the substituted C ₂ -C ₆₀ alkenyl group, the substituted C ₂ -C ₆₀ alkynyl group, the substituted C ₁ -C ₆₀ alkoxy group, the substituted C ₃ -C ₁₀ Substituted cycloalkyl groups, substituted C ₁ -C ₁₀ heterocycloalkyl groups, substituted C ₃ -C ₁₀ cycloalkenyl groups, substituted C ₁ -C ₁₀ heterocycloalkenyl groups, substituted C ₆ -C ₆₀ aryl groups, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₇ -C ₆₀ arylalkyl group, a substituted C ₁ -C ₆₀ heteroaryl group, substituted C ₁ -C ₆₀ heteroaryloxy A substituted C ₁ -C ₆₀ heteroarylthio group, a substituted C ₂ -C ₆₀ heteroarylalkyl group, a substituted monovalent non-aromatic condensed polycyclic group, and a substituted monovalent non-aromatic heterocyclic polycyclic group At least one,

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A sulfonic acid or a salt thereof, a phosphoric acid 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, an amino group, an amidino group, a hydrazine group, a hydrazone group, A C ₁ -C ₆₀ alkoxy group;

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, C ₃ -C ₁₀ cycloalkyl groups, C ₁ -C ₁₀ heterocycloalkyl groups, C ₃ -C ₈ heterocycloalkyl groups, C ₃ -C ₁₀ cycloalkyl groups, and the like, which are unsubstituted or substituted with at least _one substituent selected from the group consisting of an amino group, an amidino group, a hydrazine group, a hydrazone group, 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 ₇ -C ₆₀ arylalkyl groups, C ₁ -C ₆₀ heteroaryl groups, C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ hetero arylthio group, C ₂ -C ₆₀ heteroarylalkyl group 1 is a non-fused polycyclic aromatic group and a monovalent non-aromatic heterocyclic 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 substituted with at least one of a condensed polycyclic 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 C ₆ -C ₆₀ arylthio groups, C ₇ -C ₆₀ arylalkyl groups, C ₁ -C ₆₀ heteroaryl groups, C ₁ -C ₆₀ heteroaryloxy groups, C ₁ -C ₆₀ heteroarylthio groups, C ₂ -C ₆₀ heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic group, fused polycyclic;

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A sulfonic acid or a salt thereof, a phosphoric acid 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, an amino group, an amidino group, a hydrazine group, a hydrazone group, group, C ₁ -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 ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₇ -C ₆₀ arylalkyl group, C ₁ -C ₆₀ heteroaryl groups, C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ hetero arylthio group, C ₂ -C ₆₀ heteroarylalkyl, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-at least one of the substituted aromatic heterocyclic condensed polycyclic group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ hete Cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₇ -C ₆₀ arylalkyl group, C ₁ -C ₆₀ heteroaryl groups, C ₁ - C ₆₀ hetero aryloxy group, C ₁ -C ₆₀ hetero arylthio group, C ₂ -C ₆₀ heteroarylalkyl, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic group, fused polycyclic; And

-C (= O) (Q ₁₁ ), -Si (Q ₁₁ ) (Q ₁₂ ) (Q ₁₃ ) and -N (Q ₁₁ ) (Q ₁₂ ); ;

Q ₁₁ to Q ₁₃ 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, the acid or its salt, a sulfonic acid or a salt thereof, phosphoric acid 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 ₆₀ A substituted or unsubstituted C ₁ -C ₁₀ 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 cycloalkyl group, -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 an unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₇ -C ₆₀ arylalkyl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group , A substituted or unsubstituted C ₁ -C ₆₀ heteroaryloxy group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylthio group, a substituted or unsubstituted C ₂ -C ₆₀ heteroarylalkyl group, a substituted or unsubstituted 1 may be selected from non-aromatic condensed polycyclic groups and substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic groups.

When a group containing a certain number of carbon atoms is replaced with any group listed in the preceding paragraph, the number of carbon atoms in the resulting substituted group is determined by the number of carbon atoms contained in the original (unsubstituted) ) Is defined as the sum of the number of carbon atoms contained in the substituent. For example, when the substituted C ₁ -C ₆₀ alkyl means a C ₁ -C ₆₀ alkyl group substituted with a C ₆ -C ₆₀ aryl group, the total number of carbon atoms of the obtained aryl substituted alkyl group is C ₇ -C ₁₂₀ .

Hereinafter, compounds and organic light emitting devices according to one embodiment of the present invention will be described in more detail with reference to the following 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]

In the following, "THP" means a tetrahydropyranyl group.

Synthesis Example 1: Synthesis of Compound 1

1) Synthesis of Compound A3

(10.9 g, 31.37 mmol), Pd (OAc) ₂ (0.29 g, 1.31 mmol), triphenylphosphine (0.69 g, 2.61 mmol) and K ₂ CO ₃ (7.23 g, 52.28 mmol) were mixed with 90 mL of acetonitrile and 45 mL of methanol. The mixture was stirred at 50 ° C. for 18 hours, Filtered. From this, the organic layer was extracted with dichloromethane, and anhydrous magnesium sulfate (MgSO ₄ ) was added to remove moisture. The filtrate obtained by filtration was reduced in pressure and the resulting residue was purified by column chromatography on ethyl acetate: Purification via chromatographic methods provided 2.43 g (24%) of compound A3. The obtained compound was confirmed by LCMS and ¹ H NMR.

_{1H-NMR (CDCl 3) δ8.61} (s, 1H), 7.36 (s, 1H), 6.79 (s, 1H), 6.30 (dd, 1H), 4.02 (d, 1H), 3.60 (t, 1H) , 2.51 (s, 3H), 2.09 (m, 2H), 1.71 (m, 2H), 1.54

MS: m / z 391.04 [(M + 1) ^&lt; ⁺ & gt ^; ] [

2) Synthesis of Compound A2

Compound A3 (2.43 g, 6.23 mmol) , phenylboronic acid (phenylboronic acid) (0.91 g, 7.47 mmol), Pd (PPh 3) 4 (0.50 g, 0.44 mmol), K 2 CO 3 (1.29 g, 9.34 mmol) Was mixed with 20 mL of tetrahydrofuran and 10 mL of distilled water, stirred at 75 DEG C for 12 hours, and cooled to room temperature. The organic layer was extracted with ethyl acetate, and anhydrous magnesium sulfate (MgSO ₄ ) was added to remove water. The filtrate was then filtered to remove the filtrate. The residue was purified by column chromatography on a column of ethyl acetate: hexane = Purification via chromatographic methods afforded 2.08 g (86%) of compound A2. The obtained compound was confirmed by LCMS and ¹ H NMR.

_{1H-NMR (CDCl 3) δ8.50} (s, 1H), 7.61 (s, 1H), 7.53 (m, 3H), 7.39 (m, 2H), 7.03 (s, 1H), 6.30 (dd, 1H) , 4.02 (d, 1 H), 3.60 (t, 1 H), 2.42 (s, 3 H), 2.09 (m,

MS: m / z 388.16 [(M + 1) ^&lt; ⁺ & gt ^; ] [

3) Synthesis of Compound A1

Compound A2 (0.99 g, 2.58 mmol) was dissolved in 15 mL of 1,4-dioxane, and hydrochloric acid (6.44 mL, 12.88 mmol) dissolved in 2.0 N of diethyl ether was slowly added thereto and stirred at 65 ° C for 2 hours Respectively. After completion of the reaction, the reaction mixture was cooled to room temperature, and the resulting precipitate was filtered under reduced pressure, followed by washing with diethyl ether. The obtained solid was neutralized with an aqueous solution of sodium hydrogencarbonate, and then the organic layer was extracted with ethyl acetate. Anhydrous magnesium sulfate (MgSO ₄ ) was added to remove moisture, and the filtrate was filtered. The obtained residue was dissolved in ethyl The residue was purified by column chromatography over acetate: hexane = 1: 5 to give 0.55 g (71%) of compound A1. The obtained compound was confirmed by LCMS and ¹ H NMR.

_{1H-NMR (CDCl 3) δ12.1} (br. S, 1H), 8.49 (s, 1H), 7.59 (s, 1H), 7.51 (m, 3H), 7.37 (m, 3H), 7.00 (s, 1H), &lt; / RTI &gt; 2.41 (s, 3H)

MS: m / z 304.10 [(M + 1) ^&lt; ⁺ & gt ^; ] [

4) Synthesis of Compound 1

Compound A1 (0.55 g, 1.82 mmol) and triosmdodecanecarbonyl (0.27 g, 0.29 mmol) were dissolved in 15 mL of diethylene glycol monoethyl ether and refluxed at 180 ° C for 18 hours. After cooling to 110 DEG C, trimethylamine N-oxide (0.16 g, 2.11 mmol) dissolved in 5 mL of diethylene glycol monoethyl ether was slowly added. After the reaction was completed, diphenylmethylphosphine (0.79 mL, 4.25 mmol) was added thereto, and the mixture was heated to 180 ° C and refluxed for 18 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered under reduced pressure and washed with methanol. The obtained compound was confirmed by LCMS and ¹ H NMR.

_{1H-NMR (CDCl 3) δ9.85} (br. S, 2H), 7.52 (t, 4H), 7.43 (t, 2H), 7.31 (d, 4H), 6.98 (m, 12H), 6.80 (t, 4H), 6.36 (br.s, 2H), 2.14 (s, 6H), 0.993 (s, 6H)

MS: m / z 1197.29 [(M + 1) ^&lt; ⁺ & gt ^; ] [

Synthesis Example 2: Synthesis of Compound 3

1) Synthesis of Compound B2

Compound A2 (2.08 g, 5.37 mmol) was mixed with 30 mL of THF, cooled to -78 째 C, and lithium diisopropylamide (LDA, 13.42 mmol) was slowly added. Thereafter, the mixture was stirred at -78 ° C for 1 hour to conduct the reaction, and then the mixture was warmed to room temperature and further reacted for 1.5 hours. Subsequently, the temperature was lowered to -78 ° C, 2-bromopropane (1.26 mL, 13.42 mmol) was added slowly, the temperature was raised to room temperature, and the reaction was continued for 12 hours. The organic layer obtained was extracted with dichloromethane, and anhydrous magnesium sulfate was added to remove water. The filtrate obtained by filtration was reduced in pressure, and the resulting residue was purified by column chromatography on ethyl acetate: hexane = 1: 8 To give 0.92 g (40%) of compound B2. The obtained compound was confirmed by LCMS and ¹ H NMR.

_{1H-NMR (CDCl 3) δ8.50} (s, 1H), 7.61 (s, 1H), 7.53 (m, 3H), 7.39 (m, 2H), 7.03 (s, 1H), 6.30 (dd, 1H) 2H), 1.99 (m, 2H), 1.99 (m, 2H), 1.71 (m, 1.07 (d, 6 H)

MS: m / z 430.20 [(M + 1) ^&lt; ⁺ & gt ^; ] [

2) Synthesis of Compound B1

Compound B2 (0.92 g, 2.37 mmol) was dissolved in 15 mL of 1,4-dioxane, and then hydrochloric acid (5.94 mL, 11.87 mmol) dissolved in 2.0 N of diethyl ether was slowly added thereto and stirred at 65 ° C for 2 hours Respectively. After completion of the reaction, the reaction mixture was cooled to room temperature, and the resulting precipitate was filtered under reduced pressure, followed by washing with diethyl ether. The obtained solid was neutralized with an aqueous solution of sodium hydrogencarbonate, and then the organic layer was extracted with ethyl acetate. Anhydrous magnesium sulfate (MgSO ₄ ) was added to remove moisture, and the filtrate was filtered. The resulting residue was dissolved in ethyl Ethyl acetate: hexane = 1: 5 to obtain 0.83 g (71%) of compound B1. The obtained compound was confirmed by LCMS and ¹ H NMR.

_{1H-NMR (CDCl 3) δ12.1} (br. S, 1H), 8.43 (s, 1H), 7.53 (s, 1H), 7.46 (m, 3H), 7.31 (m, 2H), 6.99 (s, 2H), 1.78 (m, IH), 0.79 (d, 6H)

MS: m / z 346.15 [(M + 1) ^&lt; ⁺ & gt ^; ] [

3) Synthesis of Compound 3

Compound B 1 (0.82 g, 2.38 mmol) and triosmdodecanecarbonyl (0.35 g, 0.39 mmol) were dissolved in 20 mL of diethylene glycol monoethyl ether and refluxed at 180 ° C for 18 hours. After cooling to 110 ° C, trimethylamine N-oxide (0.21 g, 2.81 mmol) dissolved in 5 mL of diethylene glycol monoethyl ether was slowly added. After the reaction was completed, diphenylmethylphosphine (1.05 mL, 5.67 mmol) was added thereto, and the mixture was heated to 180 DEG C and refluxed for 18 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered under reduced pressure and washed with methanol. The obtained compound was confirmed by LCMS and ¹ H NMR.

_{1H-NMR (CDCl 3) δ7.50} (m, 7H), 7.18 (m, 1H), 7.03 (m, 7H), 6.97 (m, 7H), 6.83 (t, 5H), 6.63 (m, 7H) , 6.39 (m, 2H), 2.36 (d, 4H), 1.90 (m, 2H), 0.65

MS: m / z 1281.39 [(M + 1) ^&lt; ⁺ & gt ^; ] [

Evaluation Example 1: PL spectrum evaluation

Compounds 1 and 3 were diluted in toluene to a concentration of 0.1 mM and PL (Photoluminecscence) spectra were measured at room temperature using an ISC PC1 Spectrofluorometer equipped with a Xenon lamp. The results are shown in Table 2 and FIG.

Compound No. λ _max
(nm) Compound 1 622 Compound 3 623

From Table 2, it can be seen that the compounds 1 and 3 emit red light.

Evaluation Example 2: Evaluation of thermal characteristics

The compound 3 was subjected to thermal analysis (N ₂ atmosphere, temperature range: room temperature to 800 ° C (10 ° C / min) - TGA, Pan Type: Pt Pan disposable Al Pan (TGA)) using TGA (Thermo Gravimetric Analysis) And the results are shown in Fig. According to Fig. 3, it can be confirmed that the compound 3 has excellent thermal stability.

Example 1

The glass substrate on which ITO / Ag / ITO was deposited to a thickness of 70 ANGSTROM / 1000 ANGSTROM / 70 ANGSTROM as the anode was cut into a size of 50 mm x 50 mm x 0.5 mm, ultrasonically washed with isopropyl alcohol and purified water for 5 minutes each, UV light was irradiated, exposed to ozone, cleaned, and installed in a vacuum deposition apparatus.

2-TNATA was deposited on the anode to form a hole injection layer having a thickness of 600 A, and 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl And a hole transporting layer having a thickness of 1350 A was formed.

(Host) and compound 1 (dopant) were co-deposited on the hole transport layer at a weight ratio of 94: 6 to form a light emitting layer having a thickness of 400 Å. Then, BCP was deposited on the light emitting layer to form a 50 Å thick hole blocking layer . Subsequently, Alq ₃ was deposited on the hole blocking layer to form an electron transporting layer having a thickness of 350 A, LiF was deposited on the electron transporting layer to form an electron injection layer having a thickness of 10 A, and MgAg Was deposited at a weight ratio of 90:10 to form a cathode having a thickness of 120 Å. Thus, an organic light emitting device (red light emission) was produced.

Example 2

An organic light emitting device (red light emission) was fabricated using the same method as in Example 1 except that Compound 3 was used instead of Compound 1 in forming the light emitting layer.

Comparative Example 1

An organic light emitting device was manufactured using the same method as in Example 1, except that Compound B was used instead of Compound 1 in forming the light emitting layer.

Comparative Example 2

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

Evaluation Example 3: Evaluation of characteristics of organic light emitting device

Current density, luminance, efficiency, external quantum efficiency, PL decay time, roll-off, color coordinates and lifetime (T ₉₇ ) were evaluated for the organic luminescent devices of Examples 1 to 3 and Comparative Examples 1 and 2 The results are shown in Table 3. A current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as the evaluation device, and the life time (T ₉₇ ) was estimated to be 97% of the initial luminance 100%.

Dopant Driving voltage
(V) Current density
(MA / cm2) efficiency
(cd / A) External quantum efficiency
(%) Decay time
(μs) Roll-off
(%) λ _max
(nm) CIEx LT ₉₇
(time) Example 1 Compound 1 4.7 7.9 19.1 18.7 0.89 11 622 0.66 125 Example 2 Compound 3 4.5 6.5 23.1 23.3 0.79 9 623 0.67 200 Comparative Example 1 B 4.9 8.0 18.9 15.1 0.87 15 616 0.64 65 Comparative Example 2 PtOEP 7.3 10.1 4.5 4.0 24 43 645 0.69 40

It can be seen from Table 3 that the organic light emitting devices of Examples 1 and 2 are more efficient than the organic light emitting devices of Comparative Examples 1 and 2.

The organometallic compound of Formula 1 has improved lifetime and efficiency of an organic light emitting device including an aryl group such as a phenyl group at a specific position of the pyridine ring by comparing the results of Examples 1, 2, Example 2 &lt; tb &gt; &lt; / TABLE &gt;

In addition, by introducing a substituent having a large steric hindrance at the? -Position of an aryl group substituted with pyridine, the triplet-triplet extinction can be reduced and the efficiency of the organic light emitting device including the same can be improved. Examples 1 and 2 .

Since the compounds included in the organic light emitting devices of Examples 1 and 2 have a relatively short decay time, it is confirmed that the organic light emitting devices of Examples 1 and 2 can have a high efficiency at the same time with a small roll-off I could.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. . Accordingly, the true scope of the present invention should be determined by the technical idea of the appended claims.

10: Organic light emitting device
11: first electrode
15: Organic layer
19: Second electrode

Claims (20)

An organometallic compound represented by the following formula (1):
&Lt; Formula 1 >

In Formula 1,
M is Os or Ru;
R ₁₁ to R ₁₃ and R ₁₆ independently of each other represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl 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 1, a non-condensed polycyclic aromatic group and a substituted or At least one of R ₁₁ to R ₁₃ and R ₁₆ is selected from the group consisting of a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₇ -C ₁₂ aryl group, Substituted or unsubstituted C ₁ -C ₆₀ arylalkyl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryloxy group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylthio group, unsubstituted C ₂ -C ₆₀ heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic Selected from the interrogating condensed polycyclic group, and;
R ₁₄ and R ₁₅ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group and is selected from substituted or unsubstituted C ₆ -C ₆₀ aryl group;
n is selected from 1, 2, and 3;
L ₁₁ is selected from a monodentate ligand and a bidentate ligand;
m is selected from 0, 1, 2, 3 and 4. The method according to claim 1,
R ₁₁ , R ₁₂ , R ₁₃ or R ₁₆ is 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 condensation A polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group;
Two substituents of R ₁₁ , R ₁₂ , R ₁₃ and R ₁₆ are, independently of each other, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, Aromatic monocyclic non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group;
The three substituents of R ₁₁ , R ₁₂ , R ₁₃ and R ₁₆ are, independently of each other, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, Aromatic monocyclic non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group;
R ₁₁ , R ₁₂ , R ₁₃ and R ₁₆ independently represent 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 Aromatic condensed polycyclic groups, and substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic groups. The method according to claim 1,
R ₁₁ to R ₁₃ and R ₁₆ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, n-pentyl group, iso-pentyl group, sec-pentyl group, tert-pentyl group, neo-pentyl group, cyclopentyl group, cyclohexyl group and cyclo A heptyl group;
An isopropyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, an isopropyl group, a n-butyl group, , tert-butyl group, n-pentyl group, iso-pentyl group, sec-pentyl group, tert-pentyl group and neo-pentyl group; And
Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, , a cyclopentyl group, a cyclohexyl group and a cycloheptyl group substituted with at least one of n-pentyl group, iso-pentyl group, sec-pentyl group, tert-pentyl group and neo-pentyl group;
A thiazolyl group, a thiazolyl group, an oxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, A benzothiophenyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophene group such as a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a naphthyridinyl group, A phenyl group; And
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, An amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or its salt, a sulfonic acid or its salt, a phosphoric acid or its salt, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, di group, pyrazinyl group, pyrimidinyl group, triazinyl group and a _{-Si (Q 1) (Q 2} ) (Q 3) of the at least one substituted phenyl group, a naphthyl group, phenanthrenyl group, anthracenyl group, pie les A thiophene group, a thiazolyl group, an oxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolyl group, A thienyl group, a norbornyl group, a quinoxalinyl group, a quinazolinyl group, a naphthyridinyl group, a benzofuranyl group, a benzothiophenyl group, a triazinyl group, a dibenzofuranyl group and a dibenzothiophenyl group; At least one of R ₁₁ to R ₁₃ and R ₁₆ is selected from the group consisting of a phenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a crycenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, A pyridinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a naphthyridinyl group, a benzofuranyl group, a thiazolyl group, A benzothiophenyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; And
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, An amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or its salt, a sulfonic acid or its salt, a phosphoric acid or its salt, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, di group, pyrazinyl group, pyrimidinyl group, triazinyl group and a _{-Si (Q 1) (Q 2} ) (Q 3) of the at least one substituted phenyl group, a naphthyl group, phenanthrenyl group, anthracenyl group, pie les A thiophene group, a thiazolyl group, an oxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolyl group, A thienyl group, a norbornyl group, a quinoxalinyl group, a quinazolinyl group, a naphthyridinyl group, a benzofuranyl group, a benzothiophenyl group, a triazinyl group, a dibenzofuranyl group and a dibenzothiophenyl group; &Lt; / RTI &gt;
Q ₁ to Q ₃ are each independently selected from a C ₁ -C ₂₀ alkyl group and a C ₆ -C ₆₀ aryl group. The method according to claim 1,
R ₁₁ to R ₁₃ and R ₁₆ are each independently selected from the group consisting of hydrogen, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, A pentyl group and a cyclohexyl group;
An isopropyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, an isopropyl group, a n-butyl group, And tert-butyl groups;
A cyclopentyl group and a cyclohexyl group substituted with at least one of deuterium, -F, -Cl, -Br, -I, cyano group, methyl group and ethyl group;
A phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; And
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a cyano group, a methyl group, ethyl group, n- propyl Propyl group, n-butyl group, isopropyl group, n-butyl group, iso-butyl group, sec- a phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group which are substituted with at least one of -Si (CH ₃ ) ₃ , a tert-butoxy group, a phenyl group and -Si (CH ₃ ) ₃ ; At least one of R ₁₁ to R ₁₃ and R ₁₆ is selected from the group consisting of a phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; And
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a cyano group, a methyl group, ethyl group, n- propyl Propyl group, n-butyl group, isopropyl group, n-butyl group, iso-butyl group, sec- a phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group which are substituted with at least one of -Si (CH ₃ ) ₃ , a tert-butoxy group, a phenyl group and -Si (CH ₃ ) ₃ ; &Lt; / RTI &gt; The method according to claim 1,
R ₁₁ to R ₁₃ independently represent a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec- A cyclohexyl group;
An isopropyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, an isopropyl group, a n-butyl group, And tert-butyl groups;
A cyclopentyl group and a cyclohexyl group substituted with at least one of deuterium, -F, -Cl, -Br, -I, cyano group, methyl group and ethyl group;
A phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; And
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a cyano group, a methyl group, ethyl group, n- propyl Propyl group, n-butyl group, isopropyl group, n-butyl group, iso-butyl group, sec- a phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group which are substituted with at least one of -Si (CH ₃ ) ₃ , a tert-butoxy group, a phenyl group and -Si (CH ₃ ) ₃ ; &Lt; / RTI &gt;
R ₁₆ represents a phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; And
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a cyano group, a methyl group, ethyl group, n- propyl Propyl group, n-butyl group, isopropyl group, n-butyl group, iso-butyl group, sec- a phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group which are substituted with at least one of -Si (CH ₃ ) ₃ , a tert-butoxy group, a phenyl group and -Si (CH ₃ ) ₃ ; &Lt; / RTI &gt; The method according to claim 1,
R ₁₁ , R ₁₃ and R ₁₆ are independently selected from the group consisting of hydrogen, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, A pentyl group and a cyclohexyl group;
An isopropyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, an isopropyl group, a n-butyl group, And tert-butyl groups;
A cyclopentyl group and a cyclohexyl group substituted with at least one of deuterium, -F, -Cl, -Br, -I, cyano group, methyl group and ethyl group;
A phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; And
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a cyano group, a methyl group, ethyl group, n- propyl Propyl group, n-butyl group, isopropyl group, n-butyl group, iso-butyl group, sec- a phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group which are substituted with at least one of -Si (CH ₃ ) ₃ , a tert-butoxy group, a phenyl group and -Si (CH ₃ ) ₃ ; &Lt; / RTI &gt;
R ₁₂ represents a phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; And
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a cyano group, a methyl group, ethyl group, n- propyl Propyl group, n-butyl group, isopropyl group, n-butyl group, iso-butyl group, sec- a phenyl group, a thiophenyl group, a furanyl group, a thiazolyl group, an oxazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group which are substituted with at least one of -Si (CH ₃ ) ₃ , a tert-butoxy group, a phenyl group and -Si (CH ₃ ) ₃ ; &Lt; / RTI &gt; The method according to claim 1,
R ₁₄ and R ₁₅ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, A cyclohexyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, a cyclopentyl group, A phenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a klycenyl group;
An isopropyl group, an n-butyl group, an iso-butyl group, a sec-butyl group and a tert-butyl group substituted with at least one of hydrogen, deuterium, -F, -Cl, -Br and -I, Butyl group, n-pentyl group, iso-pentyl group, sec-pentyl group, tert-pentyl group and neo-pentyl group; And
Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, , a cyclohexyl group, a cycloheptyl group, a phenyl group, a naphthyl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, Anthracenyl group, pyrenyl group, and chrysenyl group; &Lt; / RTI &gt; The method according to claim 1,
R ₁₄ and R ₁₅ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, Butyl group, sec-butyl group, tert-butyl group, cyclopentyl group, cyclohexyl group, phenyl group and naphthyl group; And
N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl groups substituted with at least one of hydrogen, &Lt; / RTI &gt; The method according to claim 1,
R ₁₄ and R ₁₅ independently represent hydrogen, deuterium, -F, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, -Butyl group, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ and phenyl groups. The method according to claim 1,
and n is 2, an organometallic compound. The method according to claim 1,
L &lt; ₁₁ &gt; is a ligand represented by any one of the following formulas (2-1) to (2-12)

Of the above-mentioned formulas (2-1) to (2-12)
A ₂₁ and A ₂₂ are independently from each other selected from the group consisting of C ₅ -C ₂₀ cyclic groups and C ₁ -C ₂₀ heterocyclic groups;
X ₂₁ , X ₂₂ , X ₂₈ and X ₂₉ are independently of each other selected from C and N;
X ₂₃ is N or C (Q ₂₃ ); X ₂₄ is N or C (Q ₂₄ ); X ₂₅ is N or C (Q ₂₅ ); X ₂₆ is N or C (Q ₂₆ ); X ₂₇ is N or C (Q ₂₇ );
X ₂₈ is O, S or N (Q ₂₈ ); X ₂₉ is O, S or N (Q ₂₉ );
Y ₂₁ and Y ₂₂ are, independently of each other, a single bond, a double bond, a substituted or unsubstituted C ₁ -C ₅ alkylene group, a substituted or unsubstituted C ₂ -C ₅ alkenylene group and a substituted or unsubstituted C ₆ It is selected from -C ₁₀ arylene group;
Z ₂₁ and Z ₂₂ are independently from each other selected from N, O, N (R ₂₅ ), P (R ₂₅ ) (R ₂₆ ) and As (R ₂₅ ) (R ₂₆ );
Z ₂₃ is selected from P and As;
Z ₂₄ is selected from CO and CH ₂ ;
R ₂₁ to R ₃₀ and Q ₂₃ to Q ₂₉ are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, , Substituted or unsubstituted C ₁ -C ₆₀ alkyl groups, substituted or unsubstituted C ₂ -C ₆₀ alkenyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted aryl groups, 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 aryl come tea, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent A non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group; ; R ₂₁ and R ₂₂ may be optionally combined to form a ring; R ₂₇ and R ₂₈ may be optionally combined to form a ring; R ₂₈ and R ₂₉ may be optionally combined to form a ring; R ₂₉ and R ₃₀ may be optionally combined to form a ring;
b21 and b22 are independently of each other selected from 1, 2 and 3;
* And * are independent sites of bonding to neighboring atoms. The method of claim 1, wherein
L &lt; ₁₁ &gt; is a ligand represented by any one of the following formulas (3-1) to (3-25)

Of the above formulas (3-1) to (3-25)
Ph is a phenyl group;
Ph-d &lt; ₅ &gt; is a phenyl group in which all hydrogen is substituted with deuterium;
* And * are binding sites with neighboring atoms. The method of claim 1, wherein
and m is selected from 1 and 2. The method according to claim 1,
n is 2 and m is 2;
n is 2, and m is 1. The method of claim 1, wherein
M is Os or Ru;
R ₁₁ to R ₁₃ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₃ -C _A substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted 2 is selected from non-aromatic heterocyclic polycyclic groups,
R ₁₆ is a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted 2 Is selected from non-aromatic heterocyclic polycyclic groups;
R ₁₄ and R ₁₅ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group and is selected from substituted or unsubstituted C ₆ -C ₆₀ aryl group;
n is selected from 1, 2, and 3;
L ₁₁ is selected from a monodentate ligand and a bidentate ligand;
and m is selected from 0, 1, 2, 3 and 4. The method of claim 1, wherein
Wherein the organometallic compound represented by Formula 1 is represented by any one of Chemical Formulas 1-1 to 1-9,

Among the above formulas 1-1 to 1-9,
M, R ₁₂ to R ₁₅ , n, L ₁₁ and m are as defined in Formula 1,
Ar ₁₁ is a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted 2 Is selected from non-aromatic heterocyclic polycyclic groups,
Provided that R ₁₂ to R ₁₅ are not each hydrogen. The method of claim 1, wherein
Wherein the organometallic compound represented by Formula 1 is represented by any one of Chemical Formulas 1-11 to 1-19 and 1-21 to 1-29,

Of the above formulas 1-11 to 1-19 and 1-21 to 1-29,
L &lt; ₁₁ &gt; and m are as defined in formula (1) above;
Ar _11a and Ar _11b independently represent a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group And a substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic group;
and;
R _12a and R _12b independently of one another refer to the definition of R _{12 in} the above formula (1);
R _13a and R _13b independently of one another refer to the definition of R _{13 in} the above formula (1);
R _14a and R _14b independently of one another refer to the definition of R ₁₄ in Formula 1 above;
R _15a and R _15b independently of one another refer to the definition of R ₁₅ in Formula 1 above;
L &lt; ₁₂ &gt; refers to the definition of L &lt; ₁₁ &gt; in the above formula (1)
Provided that R ₁₂ to R ₁₅ are not each hydrogen. The method of claim 1, wherein
Wherein the organometallic compound represented by Formula 1 is selected from the following compounds 1 to 176:

A first electrode; A second electrode; And an organic layer including a light emitting layer interposed between the first electrode and the second electrode, wherein the organic layer comprises at least one organometallic compound of claim 1. 20. The method of claim 19,
Wherein the organic metal compound is contained in the light emitting layer.

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