KR20160012880A - Organometallic compound and organic light emitting device including the same - Google Patents

Abstract

Disclosed are an organometallic compound and an organic light-emitting device comprising the organometallic compound. The organometallic compound is represented by chemical formula 1. The organometallic compound has excellent electrical properties and thermal stability. The organic light-emitting device using the organometallic compound can have a low driving voltage, high efficiency, high luminance, and long lifespan properties.

Description

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

Organometallic compounds and organic light emitting devices containing them are disclosed.

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.

And to provide an organic electroluminescent device employing the same.

According to one aspect, there is provided an organometallic compound represented by the following formula:

≪ Formula 1 >

M (L ₁ ) _{n 1} (L ₂ ) _{n 2}

Wherein L ₁ is a divalent ligand represented by the following general formula (2), L ₂ is selected from a monovalent organic ligand, a divalent organic ligand and a trivalent organic ligand, L ₂ is a ligand represented by the following general formula Not;

(2)

In Formula 2,

M is iridium, platinum, osmium, titanium, zirconium, hafnium, europium, terbium or thorium;

Y ₁ and Y ₂ are independently of each other carbon (C) or nitrogen (N);

Y ₁ and N are connected by a single bond or a double bond, Y ₂ and C are connected by a single bond or a double bond;

CY ₁ is a C ₁ -C ₆₀ heterocyclic group;

CY ₂ is a C ₅ -C ₆₀ cyclic group or a C ₁ -C ₆₀ heterocyclic group;

CY ₁ CY ₂ and optionally (optionally), the coupled with each other additionally via the first connector (a first linking group);

Z ₁ is hydrogen, heavy hydrogen, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone jongi, carboxylic acid or a salt thereof, 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 alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C _A substituted or unsubstituted C ₁ -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 heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted 1, a non-condensed polycyclic aromatic group, a substituted or unsubstituted monovalent non-ring aromatic hete Selected from a condensed polycyclic _{group, -N (Q 1) (Q} 2), -Si (Q 3) (Q 4) (Q 5) and _{-B (Q 6) (Q 7} ) and;

a1 is selected from an integer of 1 to 5, if a1 is 2 or more, two or more of Z ₁ are the same or different from each other;

n1 is selected from an integer of 1 to 3, when n1 is 2 or more, two or more L ₁ are the same or different from each other;

n2 is selected from an integer of 0 to 4, and when n2 is 2 or more, L2 of ₂ or more are the same or different from each other;

* And * are binding sites for M in formula (1);

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 cycloalkyl group, substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C the aromatic heterocyclic group condensed _{polycyclic-60} aryloxy group, a substituted C ₆ -C ₆₀ aryl come tea, substituted C ₁ -C ₆₀ heteroaryl group, a substituted a non-aromatic condensed polycyclic group and a substituted monovalent non- At least one of the substituents is,

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 and a C ₁ -C ₆₀ alkoxy 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 salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ - C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -N (Q ₁₁₎ ( Q _12), -Si ₍₁₃ Q) (Q _{14) (15} Q) and -B ₍₁₆ Q) (Q ₁₇₎ of the at least one substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl group, A C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

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

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 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 ₁ -C _{of 60} heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 21) (Q} 22), -Si (Q 23) (Q 24) (Q 25) and _{-B (Q 26) (Q 27} ) of the at least one substituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl ah A monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group; And

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

Wherein Q ₁ to Q ₇ , Q ₁₁ to Q ₁₇ , Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, C ₁ -C ₆ alkenyl group, C ₁ -C ₆ alkenyl group, C ₁ -C ₆ alkenyl group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, C ₂ -C ₁₀ alkynyl 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 heterocycloalkenyl group , C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic Heterocyclic polycyclic groups.

According to another aspect, there is provided a liquid crystal display comprising: a first electrode; 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 organic metal compound may be included in the light emitting layer, the organic metal compound contained in the light emitting layer may serve as a dopant, and the light emitting layer may further include a host.

The organic metal compound has excellent electrical characteristics and thermal stability. The organic light emitting device employing the organic metal compound may have low driving voltage, high efficiency, high luminance, and long life.

1 is a schematic cross-sectional view of an organic light emitting device according to an embodiment.
2 is a PL (photoluminescent) spectrum of Compound 1. Fig.
3 is a PL spectrum of Compound 2. Fig.
4 is a PL spectrum of Compound 3. Fig.
5 is a PL spectrum of Compound 4. Fig.
Fig. 6 is TGA (Thermo Gravimetric Analysis) data of Compound 1. Fig.
7 is a graph of the luminance-efficiency / y of the OLEDs of Examples 1 to 5. Fig.
8 is a time-luminance graph of OLEDs of Examples 1 to 5. Fig.

The organometallic compound is represented by the following Formula 1:

≪ Formula 1 >

M (L ₁ ) _{n 1} (L ₂ ) _{n 2}

Wherein L ₁ is a divalent ligand represented by the following general formula (2), L ₂ is selected from a monovalent organic ligand, a divalent organic ligand and a trivalent organic ligand, L ₂ is a ligand represented by the following general formula Not;

(2)

In the above formula (2), * and * 'are binding sites for M in formula (1).

M in Formula 1 may be at least one selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Terbium, to be.

For example, M in Formula 1 may be Ir or Pt.

In Formula 2, Y ₁ and Y ₂ may independently be carbon (C) or nitrogen (N).

For example, Y ₁ and Y ₂ may all be carbon, but are not limited thereto.

Y ₁ and N in Formula 2 are connected to each other by a single bond or a double bond, and Y ₂ and C are connected to each other by a single bond or a double bond.

In the above formula (2), CY ₁ may be a C ₁ -C ₆₀ heterocyclic group, and CY ₂ may be a C ₅ -C ₆₀ cyclic group or a C ₁ -C ₆₀ heterocyclic group.

For example, CY ₁ in the above formula (2) may be a pyrrole, imidazole, pyrazole, thiazole, isothiazole, oxazole, isooxazole, triazole, pyridine, pyrazine, pyrimidine, pyridazine, quinoline, Isoquinoline, benzoquinoline, quinoxaline, quinazoline, benzoimidazole, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole or triazine,

CY < _{2 >} is selected from the group consisting of benzene, naphthalene, fluorene, spiro-fluorene, indene, pyrrole, thiophene, furan, imidazole, pyrazole, thiazole, isothiazole, oxazole, isooxazole, Benzoquinoline, quinoxaline, quinazoline, carbazole, benzoimidazole, benzofuran, benzothiophene, isobenzothiophene, benzoquinone, benzothiophene, benzothiophene, Oxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, dibenzofuran, or dibenzothiophene.

As another example, CY ₁ in the above formula (2) may be imidazole, triazole or pyridine, and CY ₂ may be benzene or pyridine, but is not limited thereto.

According to one embodiment, CY ₁ in the formula (2) may be imidazole or pyridine, and CY ₂ may be benzene.

CY ₁ and CY ₂ in Formula 2 may further be bonded to each other through a first linking group. The first linking group may be represented by the following formula (6).

(6)

* - (Z ₃₁ ) _{b 1} - * '

중에서 선택되고; The formula (6) are of Z _31, * -O- * ', * -S- *', * -N (Q 41) - * ', * -C (Q 44) = C (Q 45) - *' and

;

Q ₄₁ and Q ₄₄ to Q ₄₉ 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 a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

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, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ - C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-at least one of the substituted aromatic heterocyclic condensed polycyclic group, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl groups and C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryl A C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group; 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 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 ₁ -C ₆₀ hetero aryl group, 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 heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, 1 is a non-aromatic condensed polycyclic group and a monovalent non- Hyangjok condensed polycyclic heteroaryl group; ;

b1 is selected from an integer of 1 to 10, and when b1 is 2 or more, a plurality of Z _31s may be the same as or different from each other.

For example, in Formula 6, Q ₄₁ to Q ₄₉ 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 a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy 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 ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of a salt thereof, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group; And

A phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group; , But is not limited thereto.

로 표시되고(즉, 화학식 6 중 b1 = 1), 상기 Q₄₄ 내지 Q₄₉는 서로 독립적으로, 수소, C₁-C₁₀알킬기 또는 C₁-C₁₀알콕시기일 수 있으나, 이에 한정되는 것은 아니다. For example, CY ₁ and CY ₂ in Formula 2 are bonded to each other through a single linking group, and the first linking group is -C (Q ₄₄ ) = C (Q ₄₅ )-*' or

(I.e., b1 = 1 in Formula 6), Q ₄₄ to Q ₄₉ may independently be hydrogen, a C ₁ -C ₁₀ alkyl group, or a C ₁ -C ₁₀ alkoxy group, but the present invention is not limited thereto.

Wherein Z ₁ is selected from the group consisting of hydrogen, deuterium, 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, A substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted Or 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 heterocycloalkyl alkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted a C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted 1, a non-condensed polycyclic aromatic group, a substituted or unsubstituted 1 Non-aromatic heterocyclic group may be selected from a condensed polycyclic _{group, -N (Q 1) (Q} 2), -Si (Q 3) (Q 4) (Q 5) and _{-B (Q 6) (Q 7} ). Here, the description of Q ₁ to Q ₇ will be described later.

For example, Z ₁ in the formula (2)

Hydrogen, heavy hydrogen, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone jongi, carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₂₀ alkyl group and a C ₁ - A C ₂₀ alkoxy 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 ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of a salt thereof, 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, imidazopyridinyl, and imida Pyrimidinyl 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 salt thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoran te group, a triphenylmethyl group les, pie LES group, Cry An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, A heterocyclic group, a phenanthroline group, a phenanthroline group, an imidazolyl group, an indolyl group, an indolyl group, an indazolyl group, a fluorenyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, A benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, A thiazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothiazolyl group, an imidazolyl group, A naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthrone group substituted with at least one of -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ), a diazopyridinyl group, an imidazopyrimidinyl group, A thiophene group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, an isoxazolyl group, an isoxazolyl group, A pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, A sulfonyl group, a phenanthrolinyl group, a benzoimidazole 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 dibenzofuranyl group, A benzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; And

_{-Si (Q 3) (Q 4} ) (Q 5); ≪ / RTI >

Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ independently represent hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, A thiazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazole group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, A pyridinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group , A quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, , A tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, Benzoin thiophenyl group, benzo carbazole group, a dibenzo carbazole group, a piperidinyl group, and although already jopi already be selected from imidazo pyrimidinyl group, and the like.

According to one embodiment, Z < ₁ > in the above formula (2)

A halogen atom, a cyano group, a cyano group, a cyano group, a nitro group, a nitro group, a methyl group, an ethyl group, a propyl group, a n-butyl group, an isobutyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, , a tert-octyl group, an n-nonyl group, an isononyl group, a secononyl group, a tert-nonyl group, an n-decanyl group, an isodecanyl group, Propoxy, butoxy and pentoxy;

An isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec Heptyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, Decyl group, iso-octyl group, sec-octyl group, tert-octyl group, tert-octyl group, iso-nonyl group, sec- A decanyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group and a pentoxy group;

A phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group and a dibenzofuranyl group;

(Q ₃₃ ) (Q ₃₄ ), which is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, ) ( _Q35 ), each of which is substituted with at least one group selected from the group consisting of a halogen atom, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, And

_{-Si (Q 3) (Q 4} ) (Q 5); ≪ / RTI >

Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ are each independently selected from the group consisting of hydrogen, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group But is not limited thereto.

According to another embodiment, in Formula 1 L ₁ can be selected from ligands represented by the formula 2G to ligand represented by the formula (2A) below.

The description of Z &_lt; _1a > to Z &_lt; _1d > in the above formulas 2A to 2H independently of each other, refer to the description of Z ₁ in the present specification.

For example, Z _1a to Z _1d in the above formulas (2A) to (2H)

A halogen atom, a cyano group, a cyano group, a cyano group, a nitro group, a nitro group, a methyl group, an ethyl group, a propyl group, a n-butyl group, an isobutyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, , a tert-octyl group, an n-nonyl group, an isononyl group, a secononyl group, a tert-nonyl group, an n-decanyl group, an isodecanyl group, Propoxy, butoxy and pentoxy;

An isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec Heptyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, Decyl group, iso-octyl group, sec-octyl group, tert-octyl group, tert-octyl group, iso-nonyl group, sec- A decanyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group and a pentoxy group;

A phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group and a dibenzofuranyl group;

(Q ₃₃ ) (Q ₃₄ ), which is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, ) ( _Q35 ), each of which is substituted with at least one group selected from the group consisting of a halogen atom, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, And

_{-Si (Q 3) (Q 4} ) (Q 5); ≪ / RTI >

Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ are each independently selected from the group consisting of hydrogen, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group But is not limited thereto.

According to another embodiment, L ₁ in the above formula (1) is selected from a ligand represented by the following formula (2A-1) to a ligand represented by the formula (2C-1) and a ligand represented by the formula Can be:

≪ Formula 2A-1 > ≪ Formula 2A-2 >

≪ Formula (2B-1) > ≪ Formula 2B-2 &

≪ Formula 2C-1 & ≪ Formula 2C-2 &

In the above formulas 2A-1 to 2C-1 and 2A-2 to 2C-2

Z _1a , Z _1b and Z ₁₁ to Z ₁₅ independently represent a hydrogen atom, a nitro group, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, is selected from the group and possess _{-Si (Q 33) (Q 34} ) (Q 35),

Q ₃₃ to Q ₃₅ may be independently selected from among hydrogen, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group, But is not limited thereto.

According to another embodiment, L ₁ in the above formula ( ₁₎ is selected from the ligands represented by the above formula (2A-1) to the ligands represented by the formula (2C-1), and Z ₁₁ and Z ₁₂ are, each independently, a nitro group, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, pyridinium group and a -Si (Q ₃₃₎ MIDI group, possess triazole (Q ₃₄ each ) ≪ / _RTI > ( _Q35 ).

In formula (2), a1 represents the number of Z1, and may be selected from an integer of 1 to 5. For example, a1 can be 1, 2, or 3. When a ₁ is 2 or more, Z ₁ of 2 or more may be the same as or different from each other.

L ₂ in the above formula (1) is selected from any of monovalent organic ligands, bivalent organic ligands and trivalent organic ligands, and L ₂ is not a ligand represented by the above formula (2). Therefore, the ligands included in the category of the formula (2) defined in the present specification in the following formulas (3-1) and (4-1) to (4-72) are excluded. For example, L < ₂ > in the above formula (1) may be different from L < ₁ >.

According to one embodiment, L < ₂ > in the above formula (1) may be selected from a ligand represented by the following formula (3-1) to a ligand represented by the following formula (3-7)

In the formulas (3-1) to (3-7)

Y ₁₁ to Y ₁₆ independently of one another are carbon (C) or nitrogen (N);

CY ₃ to CY ₅ are, independently of each other, a C ₅ -C ₆₀ cyclic group or a C ₁ -C ₆₀ heterocyclic group,

Z ₂₁ to _{Z 26, R 31, R 32a} , R 32b, R 32c, R 33a, R 33b and R ₃₄ to R ₃₈ are independently of each other, hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, A sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, -SF ₅ , a substituted or unsubstituted C ₁ -C ₆ alkyl group, a substituted or unsubstituted C ₁ -C ₆ alkyl group, a substituted or unsubstituted C ₁ -C ₆ alkoxy group, -C ₆₀ alkyl, substituted or unsubstituted C ₂ -C ₆₀ alkenyl, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ or unsubstituted alkoxy groups, substituted or unsubstituted ring C _A substituted or unsubstituted C ₁ -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 heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ hetero aryl group, a substituted or unsubstituted monovalent non-aromatic hydrocarbon ring selected from a condensed polycyclic group, and _{-Si (Q 41) (Q 42} ) (Q 43) - an aromatic condensed polycyclic group, a non-substituted or unsubstituted 1 Being;

c1 to c3 are each independently selected from integers from 1 to 5;

A ₁ is P or As;

X _11a and X _11b are independently of each other N, O, N (R ₃₄ ), P (R ₃₅ ) (R ₃₆ ) or As (R ₃₇ ) (R ₃₈ );

R _{33 "} is a single bond, a double bond, a substituted or unsubstituted C ₁ -C ₅ alkylene group or a substituted or unsubstituted C ₂ -C ₅ alkenylene group;

Q ₄₁ to Q ₄₃ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, acid or its salt, a sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 non-aromatic heterocyclic is selected from the condensed polycyclic group;

* And * are the binding sites for M in formula (1).

For example, the CY ₃ to CY ₅ may be independently selected from the group consisting of benzene, naphthalene, fluorene, spiro-fluorene, indene, pyrrole, thiophene, furan, imidazole, pyrazole, thiazole, Isooxazole, triazole, pyridine, pyrazine, pyrimidine, pyridazine, quinoline, isoquinoline, benzoquinoline, quinoxaline, quinazoline, carbazole, benzoimidazole, benzofuran benzofuran, benzothiophene, isobenzothiophene, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, dibenzofuran or dibenzothiophene;

Z ₂₁ to Z ₂₆ , R ₃₁ , R _32a , R _32b , R _32c , R _33a , R _33b and R ₃₄ to R ₃₈ independently of one another,

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 a salt thereof, -SF ₅ , a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy 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 ₂₀ alkyl group and a C ₁ -C ₆₀ alkoxy group substituted with at least one of a salt thereof, 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, imidazopyridinyl, and imida Pyrimidinyl 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 salt thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoran te group, a triphenylmethyl group les, pie LES group, Cry An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, A heterocyclic group, a phenanthroline group, a phenanthroline group, an imidazolyl group, an indolyl group, an indolyl group, an indazolyl group, a fluorenyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, A benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, A thiazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothiazolyl group, an imidazolyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a crylan group, an imidazopyrimidinyl group substituted with at least one of a pyridyl group, , Pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl A quinolinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a phenanthrolinyl group, an isoindolyl group, an indolyl group, an indolyl group, a pyrrolyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, A benzimidazolyl group, a benzofuranyl group, Benzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, A divalent group, a dibenzocarbazolyl group, an imidazopyridinyl group, or an imidazopyrimidinyl group; And

_{-Si (Q 41) (Q 42} ) (Q 43); ;

c1 to c3 are, independently of each other, 1, 2 or 3;

X _11a and X _11b are independently of each other O, P (R ₃₅ ) (R ₃₆ ) or As (R ₃₇ ) (R ₃₈ );

R _{33 "} is a single bond, a double bond, a substituted or unsubstituted C ₁ -C ₂ alkylene group or a substituted or unsubstituted C ₂ alkenylene group;

Q ₄₁ to Q ₄₃ may independently be selected from among hydrogen, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group, But is not limited thereto.

According to another embodiment, L < ₂ > in the general formula (1) is selected from the ligands represented by the general formulas (3-1) to (3-4)

CY < ₃ > is pyridine, imidazole, pyrazole, triazole or tetrazole,

CY < ₄ > is benzene, pyridine, pyrimidine, or triazine,

CY < ₅ > is benzene or pyridine;

Y ₁₁ is N;

Y ₁₂ , Y ₁₃ and Y ₁₅ are C;

Y ₁₄ and Y ₁₆ are independently of each other N or C;

Z &_lt; ₂₁ > to Z < ₂₆ >

A halogen atom, a cyano group, a cyano group, a cyano group, a nitro group, -SF ₅ , a methyl group, an ethyl group, a propyl group, a n-butyl group, an isobutyl group, heptyl, sec-heptyl, tert-heptyl, n-hexyl, isohexyl, A tert-octyl group, a tert-octyl group, a tert-octyl group, a tert-octyl group, an isononyl group, a sec-nonyl group, - decanyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, phenyl, naphthyl, pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl and dibenzothiophenyl groups; And

An isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec Heptyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, Decyl group, iso-octyl group, sec-octyl group, tert-octyl group, tert-octyl group, iso-nonyl group, sec- A decanyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group and a dibenzothiophenyl group; ;

c1 to c3 may independently be 1, 2 or 3, but are not limited thereto.

According to another embodiment, L < ₂ > in the general formula (1) may be selected from a ligand represented by the following general formula (4-1) to a ligand represented by 4-106, but is not limited thereto:

The description of Z ₂₇ in the above formulas 4-1 to 4-104 refers to the description of Z ₂₁ in the present specification.

For example, Z ₂₁ to Z ₂₃ and Z ₂₇ in the general formulas (4-1) to (4-104)

A halogen atom, a cyano group, a cyano group, a cyano group, a nitro group, -SF ₅ , a methyl group, an ethyl group, a propyl group, a n-butyl group, an isobutyl group, heptyl, sec-heptyl, tert-heptyl, n-hexyl, isohexyl, A tert-octyl group, a tert-octyl group, a tert-octyl group, a tert-octyl group, an isononyl group, a sec-nonyl group, - decanyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, phenyl, naphthyl, pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl and dibenzothiophenyl groups; And

An isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec Heptyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, Decyl group, iso-octyl group, sec-octyl group, tert-octyl group, tert-octyl group, iso-nonyl group, sec- A decanyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group and a dibenzothiophenyl group; ;

c12 and c22 are independently of each other 1 or 2, c13 and c23 are independently of each other 1, 2 or 3, c14 and c24 are independently of each other 1, 2, 3 or 4;

* And * 'may be binding sites for M in formula (1), but are not limited thereto.

According to another embodiment, L ₁ in the formula (1) is selected from a ligand represented by the following formula (1) to a ligand represented by the formula (2), L ₂ is selected from the following formula A ligand to be represented, or a ligand represented by the general formula (3-1) (68), but is not limited thereto:

In the above formula (1), n1 represents the number of L1, and is selected from an integer of 1 to 3. When n1 is 2 or more, two or more of L < ₁ > may be the same or different from each other.

N2 in the general formula (1) is selected from an integer of 0 to 4. When n2 is 2 or more, 2 or L ₂ may be the same or different from each other. For example, n2 may be 0, 1 or 2, but is not limited thereto.

According to one embodiment, n1 = 3, n2 = 0; n1 = 2, n2 = 1; n1 = 1 and n2 = 2 in the above formula (1).

According to another embodiment, in formula (1), n1 is 3 and all three L ₁ are the same or different; n2 is 2, and two L < ₁ >

The organometallic compound represented by Formula 1 may be one of the following compounds 1 to 4.

The organometallic compound represented by Formula 1 includes at least one L ₁ represented by Formula 2, and the following Formula 2 has one cyano group and one -F as a substituent of CY ₂ . -F has a very high reactivity, and -F contained in the molecule as a substituent can be obtained when the compound is exposed to a relatively high temperature (for example, a deposition temperature when the compound is deposited on a predetermined substrate) And this may cause a reduction in the lifetime of the organic light emitting device employing the compound. However, since the following formula (2) has one cyano group and one -F as a substituent of CY ₂ , it is possible to ensure the thermal stability of the organometallic compound owing to the minimum number of -F, HOMO level (for example, color purity and HOMO level suitable for deep blue light emission).

(2)

In addition, since the organic metal compound represented by Formula 1 including the ligand represented by Formula 2 has excellent dispersion characteristics, when the organic metal compound represented by Formula 1 is used as a dopant of an organic light emitting device, Can be expected.

For example, the organometallic compound represented by Formula 1 has a maximum emission wavelength in a range of 435 nm to 500 nm, a x-color coordinate in a range of 0.14 to 0.20 (for example, in a range of 0.14 to 0.18) Is in the range of 0.10 to 0.35 (for example, in the range of 0.10 to 0.25).

Further, the results of evaluating the HOMO, LUMO and triplet (T1) energy levels for the compounds 1 and A using the DFT method of the Gaussian program (structure optimization at the level of B3LYP, 6-31G (d, p) Table 1 shows the results.

Compound No. HOMO (eV) LUMO (eV) T ₁ energy level (eV) One -5.28 -1.18 2.91 A -4.56 -0.76 2.85

<Compound A>

According to Table 1, it can be confirmed that Compound 1 has HOMO, LUMO and T ₁ energy levels suitable for use as a material for an organic light emitting device, as compared with Compound A. Accordingly, the organometallic compound represented by Formula 1 has electrical characteristics suitable for use as a material for an organic light emitting device.

The method for synthesizing the organometallic compound represented by the above formula (1) can be easily 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 organic light-emitting device has an organic layer containing an organic metal compound represented by the general formula (1) as described above, so that it can have low driving voltage, high efficiency, high luminance and long life. The organic light emitting device employing the organometallic compound represented by Chemical Formula 1 has a maximum emission wavelength in the range of 435 nm to 500 nm and an x-color coordinate in the range of 0.14 to 0.20 (for example, in the range of 0.14 to 0.18) , And a deep blue light emission having a y color coordinate in the range of 0.10 to 0.35 (for example, in the range of 0.10 to 0.25) is possible.

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, "(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 two different types 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.

In the present specification, the term "organic layer" refers to a single layer and / or a plurality of layers interposed between the first and second electrodes of the organic light emitting device. The "organic layer" may include not only an organic compound but also an organic metal complex including a metal.

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.

TPO, Spiro-NPB, methylated NPB, TAPC, HMTPD, TCTA (4,4 ', 3'- 4,4 ', 4 "-tris (N-carbazolyl) triphenylamine), Pani / DBSA (Polyaniline / Dodecylbenzenesulfonic acid), PEDOT / PSS (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)), a compound represented by Chemical Formula 201 and a compound represented by Chemical Formula One can include:

&Lt; Formula 201 >

&Lt; 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, an acenaphthylene 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; &Lt; / RTI &gt;

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 &lt; 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; &Lt; / RTI &gt;

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

&Lt; 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 a cyano group-containing compound such as the following compound 200, but are not limited thereto.

<Compound 200> <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 for 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 hole 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 hole 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, for example, at least one of the following BCP and Bphen, but is not limited thereto.

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

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

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, C ₂ -C ₆₀ alkenyl 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, a 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, 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 ₁ -C ₆₀ heteroaryl groups, substituted monovalent non-aromatic condensed polycyclic groups, and substituted monovalent non-aromatic heterocyclic condensed At least one of the substituents in the polycyclic group is,

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 and a C ₁ -C ₆₀ alkoxy 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 salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ - C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -N (Q ₁₁₎ ( Q _12), -Si ₍₁₃ Q) (Q _{14) (15} Q) and -B ₍₁₆ Q) (Q ₁₇₎ of the at least one substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl group, A C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

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

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 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 ₁ -C _{of 60} heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 21) (Q} 22), -Si (Q 23) (Q 24) (Q 25) and _{-B (Q 26) (Q 27} ) of the at least one substituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl ah A monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group; And

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

Wherein Q ₁ to Q ₇ , Q ₁₁ to Q ₁₇ , Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, C ₁ -C ₆ alkenyl group, C ₁ -C ₆ alkenyl group, C ₁ -C ₆ alkenyl group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, C ₂ -C ₁₀ alkynyl 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 heterocycloalkenyl group , C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic Heterocyclic polycyclic groups.

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]

Synthesis Example 1: Synthesis of Compound 1

Synthesis of Ligand A

To a solution of 30 mmol (9.21 g) of 2-bromo-1- (2,6-diisopropylphenyl) -1H-imidazole in 90 mL of THF -imidazole, 45 mmol (7.43 g) of 3-cyano-4-fluorophenyl) boronic acid and 0.9 mmol (1.04 g) of tetrakis- (tri 90 mmol (12.42 g) of potassium carbonate were mixed with 90 mL of toluene and 60 mL of water, and the mixture was refluxed for 72 hours Respectively. The reaction product obtained from this was cooled and a mixture of ethyl acetate and water in an organic layer was extracted. The resulting organic layer was washed with water three times, dried over magnesium sulfate, and the solvent was removed under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent: ethyl acetate and hexane) to obtain ligand A : 60%).

Synthesis of Intermediate 1

3 mmol (1.056) of IrCl ₃ .3H ₂ O and 6 mmol (2.09 g) of ligand A were added to a mixture of 90 mL of ethoxyethanol and 30 mL of water, refluxed for 24 hours, A precipitate was obtained. The precipitate was washed with water and methanol and dried at 80 &lt; 0 &gt; C under vacuum to give intermediate 1.

Synthesis of Compound 1

A solution of 2 mmol (3.682 g) of intermediate 1, 4 mmol (1.4 g) of ligand A, 2 mmol (0.512 g) of silver triflate in 20 mL of diglyme was refluxed for 24 hours and then cooled to room temperature Poured into excess water and extracted with ethyl acetate. The resulting organic layer was washed with water three times, dried over magnesium sulfate, and the solvent was removed under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent: ethyl acetate and hexane) to obtain Compound 1 %). The resulting compound was identified by MALDI-TOF.

MALDI-TOF: 1231 M / Z

Synthesis Example 2: Synthesis of Compound 2

Synthesis of ligand B

(2-bromo-1- (methyl) -1H-imidazole instead of 2-bromo-1- (2,6-diisopropylphenyl) (yield: 60%) was obtained in the same manner as in the synthesis of the ligand A of Synthesis Example 1, except that -imidazole was used as the ligand A-1.

Synthesis of intermediate 2

Intermediate 2 was obtained in the same manner as in the synthesis of intermediate 1 of Preparation Example 1 except that ligand B was used instead of ligand A. [

Synthesis of Compound 2

To a solution of 2 mol (2.512 g) of Intermediate 2, 2.5 mmol (0.673 g) of 4- (tert-butyl) -2- (3- (trifluoromethyl) pyrazol-5-yl) pyridine) and 20 mmol (2.12 g) of sodium carbonate were refluxed at 45 DEG C for 2 days, and then the solvent was removed under reduced pressure, followed by extraction with methylene chloride. The crude product thus obtained was subjected to silica gel column chromatography (eluent: methylene chloride) to give Compound 2 (yield: 50%). The resulting compound was identified by MALDI-TOF.

MALDI-TOF: 860 M / Z

Synthesis Example 3: Synthesis of Compound 3

Synthesis of intermediate 3

Intermediate 3 was obtained in the same manner as in Synthesis Example 1, except that ligand 2 was used instead of ligand A.

Synthesis of Compound 3

A silver triplet of 2 mol (2.44 g) of intermediate 3, 4 mmol (1.4 g) of ligand A and 2 mmol (0.512 g) in 50 mL of ethoxy ethanol was refluxed at 150 ° C for 2 days, The solvent was removed and then extracted with methylene chloride. The crude product thus obtained was subjected to silica gel column chromatography (eluent: methylene chloride) to obtain Compound 3 (yield: 20%). The resulting compound was identified by MALDI-TOF.

MALDI-TOF: 921 M / Z

Synthesis Example 4: Synthesis of Compound 4

Synthesis of Intermediate 4

Intermediate 4 was obtained in the same manner as in the synthesis of intermediate 1 of Preparation Example 1 except that ligand 3 was used instead of ligand A.

Synthesis of Compound 4

A silver triplate of 2 mol (2.65 g) of intermediate 4, 4 mmol (1.4 g) of ligand A and 2 mmol (0.512 g) in 50 mL of ethoxy ethanol was refluxed at 150 ° C for 2 days, The solvent was removed and then extracted with methylene chloride. The crude product thus obtained was subjected to silica gel column chromatography (eluent: methylene chloride) to obtain Compound 4 (yield: 20%). The resulting compound was identified by MALDI-TOF.

MALDI-TOF: 969 M / Z

Evaluation Example 1: PL spectral evaluation, color purity and quantum efficiency evaluation

The PL spectra, color purity and quantum efficiency of the compounds 1 to 4 were evaluated according to the methods shown in Table 2 below. The results are shown in Table 3, FIG. 2 (PL spectrum of compound 1), FIG. 3 (PL spectrum of compound 2) 4 (PL spectrum of compound 3) and FIG. 5 (PL spectrum of compound 4).

PL spectrum The compound was diluted in CH ₂ Cl ₂ to a concentration of 10 mM and the PL (Photoluminecscence) spectrum of the compound in solution was measured using an ISC PC1 Spectrofluorometer equipped with a Xenon lamp Is evaluated Quantum efficiency (PLQY) and color purity The mixed solution of CH ₂ Cl ₂ of PMMA and the corresponding compound of 8 wt% was coated on a quartz substrate using a spin coater and then heat-treated in an oven at 80 ° C. and then cooled to room temperature The obtained film was used to evaluate the luminescence quantum yields in film and the color coordination in film of the film of the compound (xenon light source, monochromator, A Hamamatsu Photonics absolute PL quantum yield measurement system equipped with a photonic multichannel analyzer and an integrating sphere and employing PLQY measurement software (Hamamatsu Photonics, Ltd., Shizuoka, Japan) Evaluated)

Compound No. Maximum emission wavelength (nm) PLQY (%) Color coordinates One 463 90 (0.139, 0.249) 2 457 - (0.14, 0.24) 3 468 - (0.14, 0.18) 4 464 - (0.146, 0.257)

From Table 3 and FIGS. 2 to 5, it was confirmed that the compounds 1 to 4 had excellent luminescent properties.

Evaluation Example 2: Evaluation of thermal stability

Compound 1 was analyzed by TGA (Thermo Gravimetric Analysis) and DSC (Differential Scanning Calorimetry) using N ₂ atmosphere, temperature range: room temperature to 700 ° C or 800 ° C (10 ° C / min) - TGA, 6 (the temperature at which 1% of the weight of the compound 1 is lost is 377 ° C, and the concentration of the compound 1 in the case of the compound 1) And the temperature at which the weight is lost to 5% is 400.9 [deg.] C). From Fig. 6, it was confirmed that Compound 1 had excellent thermal stability.

Evaluation Example 3: Evaluation of HOMO, LUMO and T1 energy levels

The HOMO, LUMO and T1 energy levels of compounds 1 and A were evaluated according to the method of Table 4, and the results are shown in Table 5.

HOMO energy level evaluation method Pt electrode (1 mm diameter), reference electrode: Pt wire, auxiliary electrode: Pt wire (1 mm diameter), Cyclic voltammetry (CV) (electrolyte: 0.1 M Bu ₄ NPF ₆ / solvent: CH ₂ Cl ₂ / ) To obtain a graph of the potential (V) -current (A) of each compound, and then the HOMO energy level of each compound was calculated from the reduction onset of the graph LUMO energy level evaluation method Each compound was diluted with CHCl ₃ to a concentration of 1 x 10 ^-5 M and the UV absorption spectrum was measured at room temperature using a Shimadzu UV-350 Spectrometer. The edge of the absorption spectrum ) And the HOMO energy level from the optical band gap (Eg) from the LUMO energy level T ₁ Energy level evaluation method A mixture of toluene and each compound (1 mg of each compound dissolved in 3 ml of toluene) was placed in a quartz cell, and the mixture was placed in liquid nitrogen (77 K). The photoluminescence spectrum was measured using a photoluminescence measuring instrument, Calculate the T1 energy level by analyzing only peaks observed at low temperatures compared to the luminescence spectrum

Compound No. HOMO (eV)
(Measured value) LUMO (eV)
(Measured value) T ₁ energy level (eV) One -5.42 -2.75 2.68 A -5.02 -2.34 2.63

From Table 5, it can be confirmed that the compound 1 has excellent electrical properties compared to the compound A.

<Compound A>

Example 1

A glass substrate on which an ITO (Indium Tin Oxide) electrode (first electrode, anode) having a thickness of 1500 Å was formed was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a plasma cleaner, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transferred to a vacuum deposition machine.

HAT-CN was deposited on the ITO electrode of the glass substrate to form a hole injection layer (HIL) with a thickness of 20 nm, a compound HT3 was deposited on the hole injection layer to form a hole transport layer having a thickness of 10 nm, MCP was deposited on the transport layer to form a 30 nm thick electron blocking layer to form a hole transporting region.

Compound H50 (host) and Compound 1 (dopant, 10 wt%) were co-deposited on the hole transporting region to form a light emitting layer with a thickness of 40 nm.

A TmPyPB layer was deposited on the light emitting layer to form an electron transport layer (ETL) having a thickness of 20 nm, and then LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 0.5 nm. On the electron injection layer, (Cathode, thickness of 100 nm) was formed to prepare an organic light emitting device.

<Compound 200>

<mCP> <Compound H50>

Example 2

An organic light emitting device was fabricated in the same manner as in Example 1 except that Compound H51 was used in place of Compound H50 as a host in forming the light emitting layer.

<Compound H51>

Example 3

An organic light emitting device was fabricated in the same manner as in Example 1 except that a compound H50 and a compound H51 (a weight ratio of 1: 9) were used as a host in forming the light emitting layer instead of the compound H50.

Example 4

An organic light emitting device was fabricated in the same manner as in Example 1 except that a compound H50 and a compound H51 (a weight ratio of 3: 7) were used as a host in forming the light emitting layer instead of the compound H50.

Example 5

An organic light emitting device was fabricated in the same manner as in Example 1 except that Compound H50 and Compound H51 (a weight ratio of 5: 5) were used as a host in forming the light emitting layer.

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

The driving voltage, efficiency, power, color purity, quantum efficiency and lifetime (T ₉₅ ) were evaluated for each of the organic light emitting devices manufactured in Examples 1 to 5, and the results are shown in Tables 6, 7, Efficiency / y graph) and Fig. 8 (time-luminance graph). A current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as an evaluation device, and the lifetime (T95) was evaluated to be 95% of the initial luminance 100%.

Host Dopant Driving
Voltage
(V) efficiency
(cd / A) power
(Im / W) Efficiency / y Example 1 Compound H50 Compound 1 6.86 14.19 6.51 66.1 Example 2 Compound H51 Compound 1 5.10 39.45 24.34 156.8 Example 3 Compounds H50 and H51 (1: 9) Compound 1 5.03 35.37 22.12 155.3 Example 4 Compounds H50 and H51 (3: 7) Compound 1 5.55 32.29 18.31 138.8 Example 5 Compounds H50 and H51 (5: 5) Compound 1 5.67 27.83 15.49 119.5

Host Dopant CIEx CIEy quantum
efficiency
(%) life span
(hr)
(T95) Example 1 Compound H50 Compound 1 0.152 0.215 9.2 0.74 Example 2 Compound H51 Compound 1 0.156 0.252 22.8 0.25 Example 3 Compounds H50 and H51 (1: 9) Compound 1 0.155 0.228 21.7 0.64 Example 4 Compounds H50 and H51 (3: 7) Compound 1 0.158 0.233 19.4 1.36 Example 5 Compounds H50 and H51 (5: 5) Compound 1 0.154 0.233 17.0 4.27

It can be seen from Tables 6 and 7 and FIGS. 7 and 8 that the organic light emitting devices of Examples 1 to 5 have a low driving voltage, a high luminance, a high power, a high efficiency, a lifting efficiency and a long life time (T ₉₅ ).

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 >
M (L ₁ ) _{n 1} (L ₂ ) _{n 2}
Wherein L ₁ is a divalent ligand represented by the following general formula (2), L ₂ is selected from a monovalent organic ligand, a divalent organic ligand and a trivalent organic ligand, L ₂ is a ligand represented by the following general formula Not;
(2)

In Formula 2,
M is iridium, platinum, osmium, titanium, zirconium, hafnium, europium, terbium or thorium;
Y ₁ and Y ₂ are independently of each other carbon (C) or nitrogen (N);
Y ₁ and N are connected by a single bond or a double bond, Y ₂ and C are connected by a single bond or a double bond;
CY ₁ is a C ₁ -C ₆₀ heterocyclic group;
CY ₂ is a C ₅ -C ₆₀ cyclic group or a C ₁ -C ₆₀ heterocyclic group;
CY ₁ CY ₂ and optionally (optionally), the coupled with each other additionally via the first connector (a first linking group);
Z ₁ is hydrogen, heavy hydrogen, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone jongi, carboxylic acid or a salt thereof, 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 alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C _A substituted or unsubstituted C ₁ -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 heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted 1, a non-condensed polycyclic aromatic group, a substituted or unsubstituted monovalent non-ring aromatic hete Selected from a condensed polycyclic _{group, -N (Q 1) (Q} 2), -Si (Q 3) (Q 4) (Q 5) and _{-B (Q 6) (Q 7} ) and;
a1 is selected from an integer of 1 to 5, in this case a1 al least 22 or more Z ₁ are the same or different from each other;
n1 is selected from an integer of 1 to 3, when n1 is 2 or more, two or more L ₁ are the same or different from each other;
n2 is selected from an integer of 0 to 4, and when n2 is 2 or more, L2 of ₂ or more are the same or different from each other;
* And * are binding sites for M in formula (1);
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 cycloalkyl group, substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C the aromatic heterocyclic group condensed _{polycyclic-60} aryloxy group, a substituted C ₆ -C ₆₀ aryl come tea, substituted C ₁ -C ₆₀ heteroaryl group, a substituted a non-aromatic condensed polycyclic group and a substituted monovalent non- At least one of the substituents is,
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 and a C ₁ -C ₆₀ alkoxy 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 salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ - C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -N (Q ₁₁₎ ( Q _12), -Si ₍₁₃ Q) (Q _{14) (15} Q) and -B ₍₁₆ Q) (Q ₁₇₎ of the at least one substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl group, A C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;
C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryl A C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group;
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 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 ₁ -C _{of 60} heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 21) (Q} 22), -Si (Q 23) (Q 24) (Q 25) and _{-B (Q 26) (Q 27} ) of the at least one substituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl ah A monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group; And
_{-N (Q 31) (Q 32} ), -Si (Q 33) (Q 34) (Q 35) and _{-B (Q 36) (Q 37} ); ;
Wherein Q ₁ to Q ₇ , Q ₁₁ to Q ₁₇ , Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, C ₁ -C ₆ alkenyl group, C ₁ -C ₆ alkenyl group, C ₁ -C ₆ alkenyl group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, C ₂ -C ₁₀ alkynyl 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 heterocycloalkenyl group , C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic Heterocyclic polycyclic groups. The method according to claim 1,
Y &lt; ₁ &gt; and Y &lt; ₂ &gt; The method according to claim 1,
CY ₁ is selected from the group consisting of pyrrole, imidazole, pyrazole, thiazole, isothiazole, oxazole, isooxazole, triazole, pyridine, pyrazine, pyrimidine, pyridazine, quinoline, isoquinoline, benzoquinoline, quinoxaline , Quinazoline, benzoimidazole, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole or triazine,
CY &lt; _{2 &gt;} is selected from the group consisting of benzene, naphthalene, fluorene, spiro-fluorene, indene, pyrrole, thiophene, furan, imidazole, pyrazole, thiazole, isothiazole, oxazole, isooxazole, Benzoquinoline, quinoxaline, quinazoline, carbazole, benzoimidazole, benzofuran, benzothiophene, isobenzothiophene, benzoin, benzothiophene, quinoline, An organometallic compound, such as oxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, dibenzofuran or dibenzothiophene. The method according to claim 1,
CY ₁ is imidazole, triazole or pyridine, and CY ₂ is benzene or pyridine. The method according to claim 1,
Z &lt; ₁ &
Hydrogen, heavy hydrogen, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone jongi, carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₂₀ alkyl group and a C ₁ - A C ₂₀ alkoxy 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 ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of a salt thereof, 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, imidazopyridinyl, and imida Pyrimidinyl 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 salt thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoran te group, a triphenylmethyl group les, pie LES group, Cry An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, A heterocyclic group, a phenanthroline group, a phenanthroline group, an imidazolyl group, an indolyl group, an indolyl group, an indazolyl group, a fluorenyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, A benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, A thiazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothiazolyl group, an imidazolyl group, A naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthrone group substituted with at least one of -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ), a diazopyridinyl group, an imidazopyrimidinyl group, A thiophene group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, an isoxazolyl group, an isoxazolyl group, A pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, A sulfonyl group, a phenanthrolinyl group, a benzoimidazole 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 dibenzofuranyl group, A benzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; And
_{-Si (Q 3) (Q 4} ) (Q 5); &Lt; / RTI &gt;
Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ independently represent hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, A thiazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazole group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, A pyridinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group , A quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, , A tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, Benzoin thiophenyl group, benzo carbazole group, a dibenzo carbazole group, a piperidinyl group, and already jopi imidazo flutes, the organometallic compound is selected from the group MIDI. The method according to claim 1,
Wherein Z &lt; ₁ &
A halogen atom, a cyano group, a cyano group, a cyano group, a nitro group, a nitro group, a methyl group, an ethyl group, a propyl group, a n-butyl group, an isobutyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, , a tert-octyl group, an n-nonyl group, an isononyl group, a secononyl group, a tert-nonyl group, an n-decanyl group, an isodecanyl group, Propoxy, butoxy and pentoxy;
An isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec Heptyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, Decyl group, iso-octyl group, sec-octyl group, tert-octyl group, tert-octyl group, iso-nonyl group, sec- A decanyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group and a pentoxy group;
A phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group and a dibenzofuranyl group;
(Q ₃₃ ) (Q ₃₄ ), which is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, ) ( _Q35 ), each of which is substituted with at least one group selected from the group consisting of a halogen atom, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, And
_{-Si (Q 3) (Q 4} ) (Q 5); &Lt; / RTI &gt;
Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ are each independently selected from the group consisting of hydrogen, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group Selected organometallic compound. The method according to claim 1,
Wherein L &lt; ₁ &gt; is selected from a ligand represented by the following formula (2A) to a ligand represented by the formula (2H):

In the above formulas (2A) to (2H)
Z _1a to Z _1d are, independently of each other,
A halogen atom, a cyano group, a cyano group, a cyano group, a nitro group, a nitro group, a methyl group, an ethyl group, a propyl group, a n-butyl group, an isobutyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, , a tert-octyl group, an n-nonyl group, an isononyl group, a secononyl group, a tert-nonyl group, an n-decanyl group, an isodecanyl group, Propoxy, butoxy and pentoxy;
An isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec Heptyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, Decyl group, iso-octyl group, sec-octyl group, tert-octyl group, tert-octyl group, iso-nonyl group, sec- A decanyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group and a pentoxy group;
A phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group and a dibenzofuranyl group;
(Q ₃₃ ) (Q ₃₄ ), which is optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, ) ( _Q35 ), each of which is substituted with at least one group selected from the group consisting of a halogen atom, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, And
_{-Si (Q 3) (Q 4} ) (Q 5); &Lt; / RTI &gt;
Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ are each independently selected from the group consisting of hydrogen, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group Is selected. The method according to claim 1,
Wherein L ₁ is selected from a ligand represented by the following formula (2A-1) to a ligand represented by the formula (2C-1) and a ligand represented by the formula (2A-2)
&Lt; Formula 2A-1 >< Formula 2A-2 &

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

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

In the above formulas 2A-1 to 2C-1 and 2A-2 to 2C-2
Z _1a , Z _1b and Z ₁₁ to Z ₁₅ independently represent a hydrogen atom, a nitro group, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, is selected from the group and possess _{-Si (Q 33) (Q 34} ) (Q 35),
Q ₃₃ to Q ₃₅ are independently selected from among hydrogen, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group. 9. The method of claim 8,
Z ₁₁ and Z ₁₂ in the above formulas 2A-1, 2B-1 and 2C-1 are independently selected from the group consisting of a nitro group, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group , pyrimidinyl group, triazinyl group and a _{-Si (Q 33) (Q 34} ) (Q 35) is selected from an organic metal compound. The method according to claim 1,
Wherein L &lt; ₂ &gt; in the formula (1) is selected from a ligand represented by the following formula (3-1) to a ligand represented by the following formula (3-7)

In the formulas (3-1) to (3-7)
Y ₁₁ to Y ₁₆ independently of one another are carbon (C) or nitrogen (N);
CY ₃ to CY ₅ are, independently of each other, a C ₅ -C ₆₀ cyclic group or a C ₁ -C ₆₀ heterocyclic group,
Z ₂₁ to _{Z 26, R 31, R 32a} , R 32b, R 32c, R 33a, R 33b and R ₃₄ to R ₃₈ are independently of each other, hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, A sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, -SF ₅ , a substituted or unsubstituted C ₁ -C ₆ alkyl group, a substituted or unsubstituted C ₁ -C ₆ alkyl group, a substituted or unsubstituted C ₁ -C ₆ alkoxy group, -C ₆₀ alkyl, substituted or unsubstituted C ₂ -C ₆₀ alkenyl, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ or unsubstituted alkoxy groups, substituted or unsubstituted ring C _A substituted or unsubstituted C ₁ -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 heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ hetero aryl group, a substituted or unsubstituted monovalent non-aromatic hydrocarbon ring selected from a condensed polycyclic group, and _{-Si (Q 41) (Q 42} ) (Q 43) - an aromatic condensed polycyclic group, a non-substituted or unsubstituted 1 Being;
c1 to c3 are each independently selected from integers from 1 to 5;
A ₁ is P or As;
X _11a and X _11b are independently of each other N, O, N (R ₃₄ ), P (R ₃₅ ) (R ₃₆ ) or As (R ₃₇ ) (R ₃₈ );
R _{33 "} is a single bond, a double bond, a substituted or unsubstituted C ₁ -C ₅ alkylene group or a substituted or unsubstituted C ₂ -C ₅ alkenylene group;
Q ₄₁ to Q ₄₃ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, acid or its salt, a sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic groups, or a monovalent non-aromatic heterocyclic condensed polycyclic group;
* And * are the binding sites for M in formula (1). 11. The method of claim 10,
CY ₃ to CY ₅ are independently selected from the group consisting of benzene, naphthalene, fluorene, spiro-fluorene, indene, pyrrole, thiophene, furan, imidazole, pyrazole, thiazole, isothiazole, Benzoquinone, benzoquinoline, quinoxaline, quinazoline, carbazole, benzoimidazole, benzofuran, benzoquinoline, isooxazole, isoxazole, triazole, pyridine, pyrazine, pyrimidine, pyridazine, quinoline, Thiophene, isobenzothiophene, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, dibenzofuran or dibenzothiophene;
Z ₂₁ to Z ₂₆ , R ₃₁ , R _32a , R _32b , R _32c , R _33a , R _33b and R ₃₄ to R ₃₈ independently of one another,
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 a salt thereof, -SF ₅ , a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy 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 ₂₀ alkyl group and a C ₁ -C ₆₀ alkoxy group substituted with at least one of a salt thereof, 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, imidazopyridinyl, and imida Pyrimidinyl 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 salt thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoran te group, a triphenylmethyl group les, pie LES group, Cry An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, A heterocyclic group, a phenanthroline group, a phenanthroline group, an imidazolyl group, an indolyl group, an indolyl group, an indazolyl group, a fluorenyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, A benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, A thiazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothiazolyl group, an imidazolyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a crylan group, an imidazopyrimidinyl group substituted with at least one of a pyridyl group, , Pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl A quinolinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a phenanthrolinyl group, an isoindolyl group, an indolyl group, an indolyl group, a pyrrolyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, A benzimidazolyl group, a benzofuranyl group, Benzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, A divalent group, a dibenzocarbazolyl group, an imidazopyridinyl group, or an imidazopyrimidinyl group; And
_{-Si (Q 41) (Q 42} ) (Q 43); ;
c1 to c3 are, independently of each other, 1, 2 or 3;
X _11a and X _11b are each independently selected from O, P (R ₃₅ ) (R ₃₆ ) and As (R ₃₇ ) (R ₃₈ );
R _{33 "} is a single bond, a double bond, a substituted or unsubstituted C ₁ -C ₂ alkylene group or a substituted or unsubstituted C ₂ alkenylene group;
Q ₄₁ to Q ₄₃ are each independently selected from the group consisting of hydrogen, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group. 11. The method of claim 10,
L &lt; ₂ &gt; is selected from ligands represented by the above formula (3-1) to ligands represented by 3-4,
CY &lt; ₃ &gt; is pyridine, imidazole, pyrazole, triazole or tetrazole,
CY &lt; ₄ &gt; is benzene, pyridine, pyrimidine,
CY &lt; ₅ &gt; is benzene or pyridine;
Y ₁₁ is N;
Y ₁₂ , Y ₁₃ and Y ₁₅ are C;
Y ₁₄ and Y ₁₆ are independently of each other N or C;
Z &_lt; ₂₁ &gt; to Z &lt; ₂₆ &gt;
A halogen atom, a cyano group, a cyano group, a cyano group, a nitro group, -SF ₅ , a methyl group, an ethyl group, a propyl group, a n-butyl group, an isobutyl group, heptyl, sec-heptyl, tert-heptyl, n-hexyl, isohexyl, A tert-octyl group, a tert-octyl group, a tert-octyl group, a tert-octyl group, an isononyl group, a sec-nonyl group, - decanyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, phenyl, naphthyl, pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl and dibenzothiophenyl groups; And
An isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec Heptyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, Decyl group, iso-octyl group, sec-octyl group, tert-octyl group, tert-octyl group, iso-nonyl group, sec- A decanyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group and a dibenzothiophenyl group; ;
and c1 to c3 are, independently of each other, 1, 2 or 3; The method according to claim 1,
L &lt; ₂ &gt; is selected from a ligand represented by the following formula (4-1) to a ligand represented by 4-106:

In the above formulas 4-1 to 4-106
Z ₂₁ to Z ₂₃ and Z ₂₇ are independently of each other,
A halogen atom, a cyano group, a cyano group, a cyano group, a nitro group, -SF ₅ , a methyl group, an ethyl group, a propyl group, a n-butyl group, an isobutyl group, heptyl, sec-heptyl, tert-heptyl, n-hexyl, isohexyl, A tert-octyl group, a tert-octyl group, a tert-octyl group, a tert-octyl group, an isononyl group, a sec-nonyl group, - decanyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, phenyl, naphthyl, pyridinyl, pyrimidinyl, triazinyl, dibenzofuranyl and dibenzothiophenyl; And
An isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec Heptyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, Decyl group, iso-octyl group, sec-octyl group, tert-octyl group, tert-octyl group, iso-nonyl group, sec- A decanyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group and a dibenzothiophenyl group; ;
c12 and c22 are independently of each other 1 or 2, c13 and c23 are independently of each other 1, 2 or 3, c14 and c24 are independently of each other 1, 2, 3 or 4;
* And * 'are binding sites for M in formula (1). The method according to claim 1,
To which the L ₁ ligand is selected from ligands represented by the formula (2) to (10) represented by the formula (2) (1),
Wherein L &lt; ₂ &gt; is selected from the group consisting of a ligand represented by the following general formula (3-1) and a ligand represented by the general formula (3-1)

The method according to claim 1,
n1 is 3, and all three L &_lt; ₁ &gt; are the same or different;
n2 is 2, and two L &lt; ₁ &gt; are equal to each other. The method according to claim 1,
An organometallic compound, which is one of the following compounds 1 to 4:

A first electrode; 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 organometallic compound. 18. The method of claim 17,
Wherein the first electrode is an anode, the second electrode is a cathode, and the organic layer includes i) a hole, which is interposed between the first electrode and the light emitting layer, and includes at least one of a hole injecting layer, a hole transporting layer, Transportation area; 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. 18. The method of claim 17,
Wherein the organic metal compound is contained in the light emitting layer, the light emitting layer further comprises a host, and the content of the organic metal compound is less than the content of the host. 18. The method of claim 17,
And emits deep blue light having a maximum emission wavelength in the range of 435 nm to 500 nm, an x color coordinate in the range of 0.14 to 0.20, and a y color coordinate in the range of 0.10 to 0.35.

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