KR20160064951A - Organometallic compound and organic light emitting device including the same - Google Patents

Abstract

An organic light-emitting device including an organic metal compound and the organic metal compound is disclosed.

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 multicolorization.

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}

(2)

M in the above formula (1) may be at least one selected from the group consisting of Ir, Ir, Pt, Os, Ti, Zr, And rhodium (Rh)

Wherein L ₁ is selected from the ligands represented by the above formula (2), n 1 is 1, 2 or 3, and when n ₁ is 2 or more, L ₁ is the same or different from each other,

Wherein L ₂ is selected from a monovalent organic ligand, a divalent organic ligand, a trivalent organic ligand and a tetravalent organic ligand, n 2 is 0, 1, 2, 3 or 4, L < _{2 &gt}; are the same or different from each other,

Chemical Formula ₁ L 1 and L ₂ are different from each other,

Formula 2 of CY ₁₁ is selected from C ₅ -C ₃₀ carbocyclic ring, C ₂ -C ₃₀ heterocyclic ring,

In Formula 2, R ₁ to R ₃ and R ₁₁ to R ₁₃ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , a hydroxyl group, a cyano group, A substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₃₀ alkyl group, a substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₃₀ alkenyl 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 ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C _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, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, 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 ah Group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic condensed polycyclic _{group, -Si (Q 1) (Q} 2) (Q 3), -N (Q ₄₎ is selected from _{(Q 5), -B (Q} 6) (Q 7) , and _{-P (= O) (Q 8} ) (Q 9),

B1 in Formula 2 is an integer selected from 0 to 3,

B2 in Formula 2 is an integer selected from 0 to 4,

B3 and b5 in the general formula (2) are independently an integer selected from 1 to 3,

At least one R ₃ of Formula 2 is linked to at least one R ₁₃ to form a substituted or unsubstituted saturated or unsaturated C ₂ -C ₃₀ cyclic ring,

* And * in the above formula (2) 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,

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

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ heterocycloalkyl group, 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, 1 is a non-condensed polycyclic aromatic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -Si (Q 11) (Q} 12) (Q 13), -N (Q 14) (Q 15), -B (Q ₁₆₎ (Q ₁₇₎ and _{-P (= O) (Q 18} ) (Q 19) from the at least one selected substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, 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;

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkenyl group, an amino group, an amidino group, a hydrazine group, 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 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 group condensed polycyclic _{, -Si (Q 21) (Q} 22) (Q 23), -N (Q 24) (Q 25), -B (Q 26) (Q 27) and _{-P (= O) (Q 28} ) (Q _A C ₃ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkenyl group substituted with at least one selected from the group consisting of a C ₁ -C ₁₀ cycloalkyl 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 A heterocyclic polycyclic group; And

_{-Si (Q 31) (Q 32} ) (Q 33), -N (Q 34) (Q 35), -B (Q 36) (Q 37) and _{-P (= O) (Q 38} ) (Q 39 );

;

Wherein Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ independently of one another are hydrogen, deuterium, -F, -Cl, -Br, -I, A nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, 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 ₃ -C ₁₀ cycloalkyl group, a substituted Or 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, a substituted or unsubstituted C ₆ -C ₁₀ heterocycloalkyl group, 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 ring Heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group.

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 included 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 has excellent driving voltage, current efficiency, power efficiency and color purity.

1 is a schematic cross-sectional view of an organic light emitting device according to an embodiment.

The organometallic compound is represented by the following Formula 1:

≪ Formula 1 >

M (L ₁ ) _{n 1} (L ₂ ) _{n 2}

M in the above formula (1) may be at least one selected from the group consisting of Ir, Ir, Pt, Os, Ti, Zr, And rhodium (Rh).

For example, in Formula 1, M may be selected from among iridium, platinum, osmium, and rhodium.

According to one embodiment, M in Formula 1 may be selected from iridium and platinum, but is not limited thereto.

L ₁ in the formula ( ₁₎ is selected from the ligands represented by the formula (2), n 1 is 1, 2 or 3, and when n ₁ is 2 or more, 2 or more L _{1 s} may be the same or different.

(2)

Wherein L ₂ is selected from a monovalent organic ligand, a divalent organic ligand, a trivalent organic ligand and a tetravalent organic ligand, n 2 is 0, 1, 2, 3 or 4, L < ₂ > may be the same or different from each other.

L ₁ and L ₂ in Formula 1 are different from each other.

For example, n1 in Formula 1 may be 1 or 2, but is not limited thereto.

As another example, the organometallic compound represented by the general formula (1) does not have a salt form composed of ion pairs and may be neutral.

According to one embodiment, M in the formula (1) is Ir, n1 + n2 is 3; Or M is Pt, n1 + n2 is 2, and the organometallic compound represented by Formula 1 may be neutral.

CY ₁₁ in the formula (2) may be selected from a C ₅ -C ₃₀ carbocyclic ring and a C ₂ -C ₃₀ heterocyclic ring.

For example, the general formula (2) of CY ₁₁ are benzene, indene, naphthalene, azulene, heptyl talren, indazol Sen, acenaphthylene, fluorene, a spy-fluorene, benzo fluorene, dibenzo fluorene, page nalren , Phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, pisene, perylene, pentacene, hexacene, pentacene, rubisene, , Benzoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinoline, phenanthridine, acridine, phenanthroline, phenazine, benzoimidazole, benzoin Wherein the compound is selected from the group consisting of furan, benzothiophene, dibenzofuran, dibenzothiophene, isobenzothiazole, benzoxazole, isobenzoxazole, carbazole, benzocarbazole, dibenzocarbazole, imidazopyridine and imidazopyrimidine ≪ / RTI >

As another example, CY ₁₁ in the above formula (2) may be a benzene, naphthalene, fluorene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, There is provided a process for the preparation of a compound represented by the general formula (1) or a pharmaceutically acceptable salt thereof selected from the group consisting of pyrene, klysene, naphthacene, picene, perylene, pentacene, hexacene, pentacene, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, , Acridine, phenanthroline, phenazine, dibenzofuran, dibenzothiophene, carbazole, benzocarbazole and dibenzocarbazole.

According to one embodiment, CY ₁₁ in the above formula (2) may be selected from benzene, naphthalene, phenanthrene, triphenylene, pyrene, fluorene, spiro-fluorene, dibenzofuran and dibenzothiophene.

According to another embodiment, CY ₁₁ in formula (2) may be benzene or naphthalene, but is not limited thereto.

In Formula 2, R ₁ to R ₃ and R ₁₁ to R ₁₃ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , a hydroxyl group, a cyano group, A substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₃₀ alkyl group, a substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₃₀ alkenyl 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 ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C _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, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, 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 ah Group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic condensed polycyclic _{group, -Si (Q 1) (Q} 2) (Q 3), -N (Q ₄ ) (Q ₅ ), -B (Q ₆ ) (Q ₇ ) and -P (= O) (Q ₈ ) (Q ₉ ).

For example, R ₁₁ to R ₁₃ in the general formula (2)

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof ₂₀ alkoxy group, a phosphoric acid group or a salt thereof, -SF _5, C ₁ -C ₂₀ alkyl group and C ₁ -C;

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, An amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a C ₁ -C ₁₀ alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, A cyclopentenyl group, a cyclopentenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group, each of which is optionally substituted with one or more groups selected from the group consisting of an alkyl group, an ethyl group, an ethyl group, an ethyl group, an octyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one selected;

A cyclopentyl group, a cyclohexyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a crycenyl group, a pyrrolyl group, a thiophenyl group, a furanyl 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, a quinolinyl group, an isoquinolinyl group, an isoxazolyl group, an isoxazolyl group, Benzoquinolyl groups, benzoquinolyl groups, benzoquinolyl groups, benzoquinolyl groups, quinoxalinyl groups, quinazolinyl groups, cinolinyl groups, carbazolyl groups, phenanthrolinyl groups, benzoimidazolyl groups, benzofuranyl groups, benzothiophenyl groups, A benzoxazolyl group, a triazolyl group An oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group;

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, Cyclohexyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, phenanthrenyl group, phenanthrenyl group, phenanthrenyl group, phenanthrenyl group, A thiophene group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, a thiophenol group, , Isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, A benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, an isoquinolinyl group, Benzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranoyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzoyl group A cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, a cyclohexyl group, a carbazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group, A cyclopentenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an imidazolyl 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 benzofuranyl 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 dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; And

_{-B (Q 6) (Q 7} ) , and _{-P (= O) (Q 8} ) (Q 9);

≪ / RTI >

Q ₆ to Q ₉ are, independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And

Deuterium, C ₁ -C ₁₀ alkyl group and the phenyl group selected from the at least one substituted, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, An isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;

≪ / RTI >

As another example, R ₁₁ to R ₁₃ in the general formula (2)

An alkyl group having 1 to 10 carbon atoms which may be substituted with at least one substituent selected from the group consisting of hydrogen, deuterium, -F, cyano, nitro, -SF ₅ , methyl, ethyl, n-propyl, isopropyl, An n-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, an isobutyl group, an isobutyl group, , a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, a n-nonyl group, an isononyl group, a secononyl group, A cyclohexyl group, a cyclohexyl group, an adamantanyl group, a norbornane group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, a cycloheptyl group, a cycloheptyl group, a cyclopentyl group, A norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group;

Heavy _{hydrogen, -F, -CD 3, -CD 2} H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, cyano, nitro, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy A cyclohexyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridyl group, a cyclopentyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbonanyl group, N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl and iso Heptyl, sec-pentyl, n-hexyl, isohexyl, sec-hexyl, , n-octyl group, iso-octyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, secononyl group, tert- A tertiary-decyl group, a methoxy group, an ethoxy group, a propoxy group, A cyclopentyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbonanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group , A pyridinyl group and a pyrimidinyl group; And

_{-B (Q 6) (Q 7} ) , and _{-P (= O) (Q 8} ) (Q 9);

≪ / RTI >

Q ₆ to Q ₉ are, independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And

Deuterium, C ₁ -C ₁₀ alkyl group and the phenyl group selected from the at least one substituted, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, An isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;

≪ / RTI >

As another example, R ₁ to R ₃ in the above formula (2)

C ₁ -C ₁₀ alkyl group, a phenyl group and a _{-Si (Q 1) (Q 2} ) (Q 3); And

Heavy hydrogen and C ₁ -C _10, at least one a, C ₁ -C ₁₀ alkyl group and a substituted phenyl group selected from the group;

≪ / RTI >

Q ₁ to Q ₃ are, independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And

Deuterium, C ₁ -C ₁₀ alkyl group and the phenyl group selected from the at least one substituted, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, An isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;

≪ / RTI >

According to one embodiment, R ₁₁ to R ₁₃ in Formula 2 are independently selected from the group consisting of hydrogen, deuterium, -F, cyano, nitro, -SF ₅ , -CH ₃ , -CD ₃ , -CD ₂ H, _{-CDH 2, -CF 3, -CF 2} H, -CFH 2, to group and represented by the formula 9-1 to 9-19 is selected from the group represented by the formula 10-1 to 10-30,

In the formula (2), R ₁ to R ₃ are, independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;

butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and -Si (Q ₁ ) (Q ₂ ) (Q ₃ ); And

At least selected from the group consisting of heavy hydrogen and C ₁ -C ₁₀ alkyl group substituted with one, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, an isopentyl A sec-pentyl group, a tert-pentyl group and a phenyl group;

≪ / RTI >

Q ₁ to Q ₃ are, independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And

Deuterium, C ₁ -C ₁₀ alkyl group and the phenyl group selected from the at least one substituted, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, An isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;

, But are not limited to:

In Formulas (9-1) to (9-19) and (10-1) to (10-30), * denotes a binding site with neighboring atoms.

In formula (2), b1 represents the number of R < ₁₁ > and is an integer selected from 0 to 3. When b1 is 2 or more, two or more R < ₁₁ > s are the same as or different from each other.

B2 in the general formula (2) represents the number of R < ₁₂ > and is an integer selected from 0 to 4; When b2 is 2 or more, two or more R < ₁₂ > s are the same as or different from each other.

B3 in the general formula (2) represents the number of R < ₁₃ > and is an integer selected from 1 to 3. [ When b3 is 2 or more, two or more R < ₁₃ > s are the same as or different from each other. For example, b3 may be 1 or 2, or 1.

B5 in Formula 2 represents the number of * - [Si (R ₁ ) (R ₂ ) (R ₃ )], and is an integer selected from 1 to 3. When b5 is 2 or more, two or more * - [Si (R ₁ ) (R ₂ ) (R ₃ )] are the same or different from each other. For example, b5 can be 1 or 2, or 1.

At least one R ₃ of Formula 2 is linked to at least one R ₁₃ to form a substituted or unsubstituted saturated or unsaturated C ₂ -C ₃₀ cyclic ring. For a description of the substituted or unsubstituted saturated or unsaturated C ₂ -C ₃₀ cyclic ring, see below.

According to one embodiment, b3 and b5 in the general formula (2) are 1, and R ₃ is connected to R ₁₃ to form a substituted or unsubstituted saturated or unsaturated C ₂ -C ₃₀ cyclic ring.

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

In Formula 2, R ₁ to R ₃ are all the same or different;

R ₁ and R ₃ are the same as each other, R ₂ is different from R ₁ ; or

Each of R ₁ to R ₃ may be different from each other.

According to one embodiment, L ₁ in the above formula (1) may be selected from the ligands represented by the following formulas (2-1) to (2-6)

The description of CY ₁₁ , R ₁ , R ₂ , R ₁₁ , R ₁₂ , b 1 and b _{2 in the} above formulas 2-1 to 2-6 is the same as described in this specification,

CY ₂ is a saturated or unsaturated C ₂ -C ₃₀ cyclic ring formed by connecting R ₃ and R ₁₃ to each other,

The description of R ₂₁ is the same as that for R ₁₁ ,

b11 is selected from an integer of 0 to 10,

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

For example, CY ₂ in the general formulas (2-1) to (2-6) may be selected from silolane, 2,3-dihydro- 2,5-dihydro-1H-silole, 3,4-dihydro-2H-silole, silole, 2,3-dihydro- Dihydro-1H-benzo [b] silole, benzosiliole, silinane, tetrahydrosiline, dihydrosiline, May be selected from tetrahydrobenzosiline and dihydrobenzosiline.

For example, L ₁ in the above formula (1) may be selected from among the ligands represented by the above formulas (2-3), (2-4) and (2-6), but is not limited thereto.

According to another embodiment, L ₁ in Formula 1 may be selected from ligands represented by the formula (2) (1) to 2 (36) to:

Of the above-mentioned structural formulas (2A) to (36)

R ₁ , R ₂ , R ₁₁ , R ₁₂ , b 1 and b ₂ are the same as described herein,

The description of R ₂₁ is the same as that for R ₁₁ ,

b11 is selected from an integer of 0 to 6,

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

For example, during CY ₁₁ formula (2) (1) to 2 (36) may be selected from benzene, naphthalene, fluorene, triphenylene, fluorene, carbazole, dibenzofuran, and dibenzothiophene.

According to one embodiment,

L ₁ in the formula (1) is selected from the group represented by the formulas (3), (4), (6), (9), (12), (27) ,

Of the above formulas 2 (3), 2 (4), 2 (6), 2 (9), 2 (12), 2 (27)

CY < ₁₁ > is benzene or naphthalene,

R ₁₁ , R ₁₂ and R ₂₁ are, independently of each other,

An alkyl group having 1 to 10 carbon atoms which may be substituted with at least one substituent selected from the group consisting of hydrogen, deuterium, -F, cyano, nitro, -SF ₅ , methyl, ethyl, n-propyl, isopropyl, An n-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, an isobutyl group, an isobutyl group, , a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, a n-nonyl group, an isononyl group, a secononyl group, A cyclohexyl group, a cyclohexyl group, an adamantanyl group, a norbornane group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, a cycloheptyl group, a cycloheptyl group, a cyclopentyl group, A norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group;

Heavy _{hydrogen, -F, -CD 3, -CD 2} H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, cyano, nitro, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy A cyclohexyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridyl group, a cyclopentyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbonanyl group, N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl and iso Heptyl, sec-pentyl, n-hexyl, isohexyl, sec-hexyl, , n-octyl group, iso-octyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, secononyl group, tert- A tertiary-decyl group, a methoxy group, an ethoxy group, a propoxy group, A cyclopentyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbonanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group , A pyridinyl group and a pyrimidinyl group; And

_{-B (Q 6) (Q 7} ) , and _{-P (= O) (Q 8} ) (Q 9);

≪ / RTI >

Q ₆ to Q ₉ are, independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And

Deuterium, C ₁ -C ₁₀ alkyl group and the phenyl group selected from the at least one substituted, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, An isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;

≪ / RTI >

R ₁ and R ₂ are, independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And

Deuterium, C ₁ -C ₁₀ alkyl group and the phenyl group selected from the at least one substituted, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, An isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;

, But is not limited thereto.

According to another embodiment, the formula of L ₁ has the formula 2A-1 to 2A-10, 2B-1 to 2B-10, 2C-1 to 2C-10, 2D-1 to 2D-10, 2E-1 To 2E-10, 2F-1 to 2F-10, and 2G-1 to 2G-10.

2E-1 to 2E-10, 2F-1 to 2F-10 and 2F-1 to 2F-10 and 2C-1 to 2C-10, the description of the 2G-1 to 2G-10 of the R _1, R ₂ and R ₁₂ is the reference bar described herein, and * and * 'is a combination of M and of the general formula (1) site, R _12a to R _12d For a description of R ₁₂ , see R ₁₂ and R _12a to R _12d are not hydrogen.

For example, in the formulas 2A-1 to 2A-10, 2B-1 to 2B-10, 2C-1 to 2C-10, 2D-1 to 2D-10, 2E-1 to 2E- 2F-10 and 2G-1 to 2G-10,

R ₁₂ and R _12a to R _12d are each independently selected from the group consisting of deuterium, -F, cyano, nitro, -SF ₅ , -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , CF ₂ H, -CFH ₂ , the groups represented by the formulas (9-1) to (9-19), and the groups represented by the formulas (10-1) to

R ₁ and R ₂ are, independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;

butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and -Si (Q ₁ ) (Q ₂ ) (Q ₃ ); And

At least selected from the group consisting of heavy hydrogen and C ₁ -C ₁₀ alkyl group substituted with one, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, an isopentyl A sec-pentyl group, a tert-pentyl group and a phenyl group;

≪ / RTI >

Q ₁ to Q ₃ are, independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And

Deuterium, C ₁ -C ₁₀ alkyl group and the phenyl group selected from the at least one substituted, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, An isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;

, But is not limited thereto.

Meanwhile, L < ₂ > in the formula (1) may be selected from ligands represented by the following formulas (3A) to (3G)

In the above formulas (3A) to (3G)

Y ₁₁ to Y ₁₆ are independently of one another carbon (C) or nitrogen (N), Y ₁₁ and Y ₁₂ are connected to each other by a single bond or a double bond, Y ₁₃ and Y ₁₄ are a single bond or a double bond Y ₁₅ and Y ₁₆ are connected to each other by a single bond or a double bond,

CY CY ₃ to ₅ are independently selected from, C ₅ -C ₆₀ carbocyclic group, and C ₂ -C ₆₀ heterocyclic group upon each other,

a1 to a3 are each independently selected from an integer of 1 to 5,

A < ₁ > is P or As,

(R ₃₄ ), P (R ₃₅ ) (R ₃₆ ), and As (R ₃₇ ) (R ₃₈ ), X _11a , X _11b , X _12a , X _12b , X _13a and X _13b are, ), With the proviso that X _12a , X _12b , X _13a and X _13b are not N and O,

R _{33 "} and R _34" are, independently of each other, a single bond, a double bond, a substituted or unsubstituted C ₁ -C ₅ alkylene group, a substituted or unsubstituted C ₂ -C ₅ alkenylene group and a substituted or unsubstituted C ₆ -C ₁₀ arylene group,

Z ₁ to _{Z 3, R 31, R 32a} , R 32b, R 32c, R 33a, R 33b, R 34 to R ₃₈ and R _35a, R _35b, R _35c and R _35d are each independently hydrogen, deuterium, A sulfonyl group or a salt thereof, a phosphoric acid group or a phosphoric acid group or a salt thereof, or a salt thereof, 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 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 come 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 aryl tea, Substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic condensed polycyclic group, -Si (Q ₁₎ ( is selected from _{Q 2) (Q 3),} -N (Q 4) (Q 5), -B (Q 6) (Q 7) , and _{-P (= O) (Q 8} ) (Q 9),

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

The substituted C ₁ -C ₅ alkylene group, the substituted C ₂ -C ₅ alkenylene group, the substituted C ₆ -C ₁₀ arylene group, the substituted C ₁ -C ₆₀ alkyl group, the substituted C ₂ -C ₆₀ alkenyl group , A substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cyclo alkenyl group, a substituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl groups, substituted monovalent non-aromatic condensed polycyclic groups, and substituted monovalent non-aromatic hydrocarbon ring, at least one of the substituents of the fused polycyclic group,

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

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ heterocycloalkyl group, 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, 1 is a non-condensed polycyclic aromatic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -Si (Q 11) (Q} 12) (Q 13), -N (Q 14) (Q 15), -B (Q ₁₆₎ (Q ₁₇₎ and _{-P (= O) (Q 18} ) (Q 19) from the at least one selected substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, 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;

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkenyl group, an amino group, an amidino group, a hydrazine group, 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 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 group condensed polycyclic _{, -Si (Q 21) (Q} 22) (Q 23), -N (Q 24) (Q 25), -B (Q 26) (Q 27) and _{-P (= O) (Q 28} ) (Q _A C ₃ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkenyl group substituted with at least one selected from the group consisting of a C ₁ -C ₁₀ cycloalkyl 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 A heterocyclic polycyclic group; And

_{-Si (Q 31) (Q 32} ) (Q 33), -N (Q 34) (Q 35), -B (Q 36) (Q 37) and _{-P (= O) (Q 38} ) (Q 39 );

≪ / RTI >

Wherein Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ independently of one another are hydrogen, deuterium, -F, -Cl, -Br, -I, A nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, 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 ₃ -C ₁₀ cycloalkyl group, a substituted Or 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, a substituted or unsubstituted C ₆ -C ₁₀ heterocycloalkyl group, 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 ring Heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group.

CY ₃ to CY ₅ in the above-mentioned formulas (3A) and (3B) are independently selected from the group consisting of cyclopentadiene, benzene, indene, 1,2,3,4-tetrahydronaphthalene, And examples thereof include azulene, heptalene, indacene, acenaphthylene, fluorene, spirobifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, , Pyrazine, pyrazole, imidazole, triazole, oxazole, pyrazine, pyrazine, pyrazine, pyrazine, pyrazine, Thiazole, thiadiazole, purine, pyridine, pyrimidine, pyrazine, pyridazine, triazine, 5,6,7,8-tetrahydroquinoline (5,6 7,8-tetrahydroquinoline, 5,6,7,8-tetrahydroisoquinoline, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, But are not limited to, quinoline, quinoline, quinoxaline, quinazoline, cinnoline, phenanthridine, acridine, phenanthroline, phenazine, benzimidazole, benzofuran, benzothiophene, isobenzothiazole, benzoxazole, And examples thereof include carbazole, dibenzocarbazole, imidazopyridine, imidazopyrimidine, dibenzofuran, dibenzothiophene, dibenzothiophene sulfone, carbazole, dibenzosilole, benzofuropyridine ) And benzothienopyridine. ≪ / RTI >

According to one embodiment, L < ₂ > in the above formula (1) is selected from the ligands represented by the above formulas (3A), (3B)

Wherein Y ₁₁ is nitrogen,

Y ₁₂ to Y ₁₄ in the formula (3A) are carbon,

3A of the general formula CY ₃ is pyridine, 5,6,7,8-tetrahydro-quinoline (5,6,7,8-tetrahydroquinoline), 5,6,7,8-tetrahydroisoquinoline (5,6,7 , 8-tetrahydroisoquinoline), quinoline and isoquinoline,

CY ₄ in the above-mentioned formula (3A) is preferably selected from the group consisting of benzene, 1,2,3,4-tetrahydronaphthalene, naphthalene, fluorene, dibenzofuran, dibenzothiophene, benzofuropyridine, and benzothienopyridine,

In Formula 3B, Y < ₁₅ > is carbon,

And Y ₁₆ is a nitrogen of the Formula 3B,

CY < ₅ > in the above formula (3B) is pyridine or pyrimidine,

Z ₁ to Z ₃ in the above formulas (3A) and (3B)

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof ₂₀ alkoxy group, a phosphoric acid group or a salt thereof, -SF _5, C ₁ -C ₂₀ alkyl group and C ₁ -C;

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, An amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a C ₁ -C ₁₀ alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, octyl group, Ada manta group, Nord Bona group, Nord Bonnet group, a cyclopentenyl group, a cyclohexenyl group, a cycloalkyl heptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group with at least one substitution selected from the group consisting of C ₁ - A C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

A cyclopentyl group, a cyclohexyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a crycenyl group, a pyrrolyl group, a thiophenyl group, a furanyl 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, a quinolinyl group, an isoquinolinyl group, an isoxazolyl group, an isoxazolyl group, Benzoquinolyl groups, benzoquinolyl groups, benzoquinolyl groups, benzoquinolyl groups, quinoxalinyl groups, quinazolinyl groups, cinolinyl groups, carbazolyl groups, phenanthrolinyl groups, benzoimidazolyl groups, benzofuranyl groups, benzothiophenyl groups, A benzoxazolyl group, a triazolyl group An oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group;

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, A cyclopentenyl group, a cycloheptenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, a cyclopentenyl group, a cycloheptyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbonanyl group, A thiazolyl group, an isothiazolyl group, an isothiazolyl group, an isothiazolyl group, an isothiazolyl group, an isothiazolyl group, an isothiazolyl group, an isothiazolyl group, a thiazolyl group, a thiazolyl group, An isoindolyl group, an indolyl group, an indazolyl group, a furyl group, an isothiazolyl group, an imidazolyl group, an imidazolyl group, a pyridazinyl group, A benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, A thiazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranoyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a di-benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, A cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, an imidazopyrimidinyl group, an imidazopyrimidinyl group, a cyclopentyl group, , A cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an imidazolyl 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 benzofuranyl 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 dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; And

_{-Si (Q 1) (Q 2} ) (Q 3), -N (Q 4) (Q 5), -B (Q 6) (Q 7) , and _{-P (= O) (Q 8} ) (Q 9 );

≪ / RTI >

a1 to a3 are independently an integer selected from 0 to 4,

A1 of the Z _1, Z _2, a2 and a2 of the two Z 2 or ₃ of neighboring substituents optionally (optionally), combine with each other C ₅ -C ₃₀ carbocyclic group, or C ₂ -C ₃₀ heterocyclic group, Lt; RTI ID = 0.0 >

Wherein Q ₁ to Q ₉ are, independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And

At least selected from the group consisting of heavy hydrogen and C _1- C ₁₀ alkyl group substituted with one, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, an isopentyl A sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;

≪ / RTI >

X _12a and X _12b in Formula 3F are O,

In the above formula (3F), R _"

A C ₂ -C ₅ alkenylene group; And

A C ₂ -C ₅ alkenylene group substituted with at least one selected from deuterium, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group and a phenyl group;

, But is not limited thereto.

According to another embodiment, L < ₂ > in the above formula (1) may be selected from the ligands represented by the following formulas (3-1) to

Of the above-mentioned formulas (3-1) to (3-111)

Z ₁ , Z ₂ , Z _1a , Z _1b , Z _2a , Z _2b , Z _2c , R _34a , R _34b and R _34c are,

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof ₂₀ alkoxy group, a phosphoric acid group or a salt thereof, -SF _5, C ₁ -C ₂₀ alkyl group and C ₁ -C;

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, An amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a C ₁ -C ₁₀ alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, octyl group, Ada manta group, Nord Bona group, Nord Bonnet group, a cyclopentenyl group, a cyclohexenyl group, a cycloalkyl heptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group with at least one substitution selected from the group consisting of C ₁ - A C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

A cyclopentyl group, a cyclohexyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a crycenyl group, a pyrrolyl group, a thiophenyl group, a furanyl 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, a quinolinyl group, an isoquinolinyl group, an isoxazolyl group, an isoxazolyl group, Benzoquinolyl groups, benzoquinolyl groups, benzoquinolyl groups, benzoquinolyl groups, quinoxalinyl groups, quinazolinyl groups, cinolinyl groups, carbazolyl groups, phenanthrolinyl groups, benzoimidazolyl groups, benzofuranyl groups, benzothiophenyl groups, A benzoxazolyl group, a triazolyl group An oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group;

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, Cyclohexyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, phenanthrenyl group, phenanthrenyl group, phenanthrenyl group, phenanthrenyl group, A thiophene group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, a thiophenol group, , Isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, A benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, an isoquinolinyl group, Benzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranoyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzoyl group A cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, a cyclohexyl group, a carbazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group, A cyclopentenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an imidazolyl 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 benzofuranyl 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 dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; And

_{-Si (Q 1) (Q 2} ) (Q 3), -N (Q 4) (Q 5), -B (Q 6) (Q 7) , and _{-P (= O) (Q 8} ) (Q 9 );

≪ / RTI >

Two or more adjacent substituents of Z ₁ , Z ₂ , Z _1a , Z _1b , Z _2a , Z _2b , Z _2c , R _34a , R _34b and R _34c may optionally be bonded to each other to form C ₅ -C ₃₀ carbocyclic group or a C ₂ -C ₃₀ heterocyclic group,

Wherein Q ₁ to Q ₉ are, independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And

At least selected from the group consisting of heavy hydrogen and C ₁ -C ₁₀ alkyl group substituted with one, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, an isopentyl A sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;

≪ / RTI >

aa2 and ab2 are, independently of each other, 1 or 2,

aa3 and ab3 are each independently selected from an integer of 1 to 3,

aa4 and ab4 are each independently selected from integers from 1 to 4,

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

According to another embodiment, the compounds represented by the following formulas (3-1) to (3-1) (60), 3-1 (61) 1 to (79), 3-1 (81) to 3-1 (88), 3-1 (91) to 3-1 (98), 3-111 and 3-112:

3-1 (61) to 3-1 (69), 3-1 (71) to 3-1 (79), 3-1 (81) To 3-1 (88), 3-1 (91) to 3-1 (98), 3-111 and 3-112,

_{Z 1, Z 2, Z 1a} , Z 1b, Z 1c, Z 1d, Z 2a, Z 2b, Z 2c, Z 2d, R 34a, R 34b and R _34c are independently of one another, deuterium, -F, a cyano group , a nitro _{group, -SF 5, -CH 3, -CD} 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, -Si (Q 1) (Q 2) (Q _3), a _{-N (Q 4) (Q 5} ), -B (Q 6) (Q 7), -P (= O) (Q 8) (Q 9), the formula 9-1 to 9-19 And a group represented by the above formulas (10-1) to (10-30)

X ₁ is O, S, C (Z ₂₁ ) (Z ₂₂ ) or N (Z ₂₃ )

Z ₃ , Z ₁₁ to Z ₁₃ and Z ₂₁ to Z ₂₃ independently of one another are hydrogen, deuterium, -F, cyano, nitro, -SF ₅ , -CH ₃ , -CD ₃ , -CD ₂ H, _{CDH 2, -CF 3, -CF 2} H, -CFH 2, -Si (Q 1) (Q 2) (Q 3), -N (Q 4) (Q 5), -B (Q 6) (Q _7), is selected from _{-P (= O) (Q 8} ) (Q 9), a group represented by the formula 9-1 to 9-19, and the group represented by the formula 10-1 to 10-30,

Wherein Q ₁ to Q ₉ are, independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And

At least selected from the group consisting of heavy hydrogen and C ₁ -C ₁₀ alkyl group substituted with one, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, an isopentyl A sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;

≪ / RTI >

d2 and e2 are, independently of each other, 0 or 2,

e3 is an integer selected from 0 to 3,

d4 and e4 are, independently of each other, an integer selected from 0 to 4,

d6 and e6 are, independently of each other, an integer selected from 0 to 6,

d8 and e8 are, independently of each other, an integer selected from 0 to 8,

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

According to one embodiment, L ₁ in the above formula (1) is selected from the ligands represented by the above-mentioned formulas (2-1) to (2-6) (for example, ligands represented by the above formulas (2) , L < ₂ > is a group represented by the formulas (3-1) to (3-1) 1 (81) to 3-1 (88), 3-1 (91) to 3-1 (98), 3-111 and 3-112.

According to another embodiment, in Formula 1 L ₁ has the formula 2A-1 to 2A-10, 2B-1 to 2B-10, 2C-1 to 2C-10, 2D-1 to 2D-10, 2E-1 1 to 2G-10, and L ₂ is selected from the ligands represented by the formulas (3-1) to (3-1) (60), (3-1 (71) to 3-1 (79), 3-1 (81) to 3-1 (88), 3-1 (91) to 3-1 98), 3-111 and 3-112, but is not limited thereto.

The organometallic compound represented by Formula 1 may be selected from the following compounds 1 to 270, but is not limited thereto:

Among the organometallic compounds represented by Formula 1, L ₁ is represented by Formula 2, and b 3 and b 5 in Formula 2 are independently 1 or more, and at least one R ₃ is bonded to at least one R ₁₃ To form a saturated or unsaturated C ₂ -C ₃₀ cyclic ring. As a result, the stability of the organometallic compound represented by Formula 1 can be improved, and the organic light emitting device employing the organometallic compound may have a long life.

For example, the HOMO, LUMO and triplet (T ₁ ) energy levels for some of the organometallic compounds are optimized using the DFT method of the Gaussian program (B3LYP, 6-31G (d, p) ) The evaluation results are shown in Table 1 below.

Compound No. HOMO (eV) LUMO (eV) T ₁ energy level (eV) One -4.768 -1.576 2.380 116 -4.752 -1.574 2.368 136 -4.707 -1.588 2.260 137 -4.798 -1.674 2.084 140 -4.729 -1.574 2.365 144 -4.638 -1.527 2.302 145 -4.804 -1.177 2.620

As can be seen from the above Table 1, the organometallic compound represented by Formula 1 has electrical characteristics suitable for use as an electric device material, for example, a material for an organic light emitting device (for example, a dopant) have.

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

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

The 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 a low driving voltage, a high efficiency, a high power, an elevator efficiency, a long life and an excellent color purity.

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, the organic layer may include a hole transporting region interposed between the first electrode and the light emitting layer, and a hole transporting region interposed between the light emitting layer and the second electrode, Wherein the hole transporting region includes at least one selected from a hole injecting layer, a hole transporting layer and an electron blocking layer, and the electron transporting region includes at least one selected from a hole blocking layer, an electron transporting layer and an electron injecting 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.

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

≪ Formula 201 >

≪ EMI ID =

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

A phenanthrenyl group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, 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

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₃ -C ₁₀ cycloalkene 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 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is non-inde at least one substitution selected from the group consisting of aromatic heterocyclic condensed polycyclic group, a phenylene group, penta alkylenyl group, a carbonyl group, a naphthyl group, an azulenyl group , A phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a triphenylenylene group, a pyrenylene group, a phenanthrenylene group, A perylene group, a perylene group, a perylene group, a perylene group, a perylene group, a perylene group, a perylene group and a perylene group;

≪ / RTI >

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

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

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof , phosphoric acid group or a salt 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 group, Ethoxy group, propoxy group, butoxy group, pentoxy group, etc.);

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group;

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

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, A phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group and a pyrenyl group which are substituted with at least one of a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group;

, But is not limited thereto.

In the above formula (201), R < ₁₀₉ &

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

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, A naphthyl group, an anthracenyl group and a pyridinyl group substituted with at least one of a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group, ;

≪ / RTI >

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

≪ Formula 201A >

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

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

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

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

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

<Compound HT-D1> <F4-TCNQ>

The hole transporting region may further include a buffer layer.

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

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

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

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

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

<mCP> <Compound H50> <Compound H51>

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

&Lt; Formula 301 >

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

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

A phenylene group, a naphthylene group, a phenanthrenylene group and a pyrenylene group 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 substituted with at least one of a phenyl group, a naphthyl group and an anthracenyl group, a naphthyl group, a phenanthrenyl group and a pyrenyl 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;

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

;

;

, But is not limited thereto.

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

&Lt; Formula 302 >

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

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

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

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

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

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

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

Next, an electron transporting region is disposed above the light emitting layer.

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

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

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

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

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

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

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

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

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

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

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

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

The thickness of the electron injection layer may be from about 1 A to about 100 A, and from about 3 A to about 90 A. When the thickness of the electron injection layer satisfies the above-described range, satisfactory electron injection characteristics can be obtained without substantially increasing the driving voltage.

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

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

In the present specification, the C ₁ -C ₆₀ alkyl group means a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms. Specific examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group , 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, a substituted C ₁ -C ₆₀ alkyl group, a substituted C ₂ -C ₆₀ alkenyl group, a substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cyclo alkyl group, a substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted a non-aromatic condensed polycyclic groups, and substituted monovalent non-aromatic heterocyclic fused polycyclic At least one of the substituents of the group is,

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

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ heterocycloalkyl group, 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, 1 is a non-condensed polycyclic aromatic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 11) (Q} 12), -Si (Q 13) (Q 14) (Q 15), -B (Q ₁₆₎ (Q ₁₇₎ and _{-P (= O) (Q 18} ) (Q 19) from the at least one selected substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, 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;

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkenyl group, an amino group, an amidino group, a hydrazine group, 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 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 group condensed polycyclic _{, -N (Q 21) (Q} 22), -Si (Q 23) (Q 24) (Q 25), -B (Q 26) (Q 27) and _{-P (= O) (Q 28} ) (Q _A C ₃ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkenyl group substituted with at least one selected from the group consisting of a C ₁ -C ₁₀ cycloalkyl 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 A heterocyclic polycyclic group; And

_{-N (Q 31) (Q 32} ), -Si (Q 33) (Q 34) (Q 35), -B (Q 36) (Q 37) and _{-P (= O) (Q 38} ) (Q 39 ); ;

Wherein Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ independently of one another are hydrogen, deuterium, -F, -Cl, -Br, -I, A nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, 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 ₃ -C ₁₀ cycloalkyl group, a substituted Or 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, a substituted or unsubstituted C ₆ -C ₁₀ heterocycloalkyl group, 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 ring Heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group.

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 Compound M2A

210 mL of ethoxyethanol and 70 mL of distilled water were mixed with 2-phenylpyridine (7.82 g, 50.37 mmol) and iridium chloride (7.89 g, 22.39 mmol) After refluxing and stirring for 24 hours, the temperature was lowered to room temperature. The resulting solid was separated by filtration, washed thoroughly in the order of water / methanol / hexane, and the obtained solid was dried in a vacuum oven to obtain 11.20 g (93%) of compound M2A.

Synthesis of Compound M1A

To the compound M2A (4.51 g, 4.20 mmol) was added 45 mL of MC and then AgOTf (2.16 g, 8.41 mmol) was dissolved in 15 mL of methanol and added. Thereafter, the mixture was stirred at room temperature for 18 hours while blocking the light with aluminum foil, and then the reaction was allowed to proceed. The resulting solid was removed by filtration through Celite, and the filtrate was reduced in pressure to obtain a solid (Compound M1A) And used for the next reaction.

Synthesis of Compound 1

90 mL of ethanol was mixed with Compound M1A (6 g, 8.41 mmol) and Compound A (3.02 g, 10.51 mmol), and the mixture was stirred at reflux for 18 hours to lower the temperature. The resulting mixture was filtered, and the obtained solid was sufficiently washed with ethanol and hexane, and subjected to column chromatography under MC: hexane to obtain 1.76 g (27%) of Compound 1. [ Mass and HPLC analysis confirmed the material.

HRMS (MALDI) calcd for C ₄₁ H ₃₂ IrN ₃ Si: m / z 787.1995, Found: 787.1999

Synthesis Example 2: Synthesis of Compound 11

Synthesis of Compound M2B

4-methyl (D ₃₎ -2- phenylpyridine _{(4-methyl (D 3)} -2-phenylpyridine) 120 mL of a (6.80 g, 39.46 mmol) and iridium chloride (iridium chloride) (6.19 g, 17.54 mmol) Ethoxyethanol and 40 mL of distilled water were mixed and refluxed for 24 hours. After the reaction was completed, the temperature was lowered to room temperature. The resulting solid was separated by filtration, washed thoroughly in the order of water / methanol / hexane, and the obtained solid was dried in a vacuum oven to obtain 8.90 g (89%) of compound M2B.

Synthesis of Compound M1B

To the compound M2B (5.50 g, 4.83 mmol) was added 45 mL of MC and AgOTf (2.48 g, 9.65 mmol) was dissolved in 15 mL of methanol and added. Thereafter, the mixture was stirred at room temperature for 18 hours while blocking the light with aluminum foil, and then the reaction was allowed to proceed. The resulting solid was removed by filtration through Celite, and the filtrate was reduced in pressure to obtain a solid (Compound M1B) And used for the next reaction.

Synthesis of Compound 11

80 mL of ethanol was mixed with Compound M1B (7.2 g, 9.66 mmol) and Compound A (3.33 g, 11.59 mmol), and the mixture was stirred at reflux for 18 hours to lower the temperature. The resulting mixture was filtered, and the obtained solid was sufficiently washed with ethanol and hexane, and subjected to column chromatography under MC: hexane to obtain 1.1 g (14%) of Compound 11. Mass and HPLC analysis confirmed the material.

HRMS (MALDI) calcd for C ₄₃ H ₃₀ D ₆ IrN ₃ Si: m / z 821.2684, Found: 821.2685

Synthesis Example 3: Synthesis of Compound 97

Synthesis of Compound M2C

120 mL of ethoxyethanol and 40 mL of distilled water were mixed with Compound A (9.70 g, 33.73 mmol) and iridium chloride (5.29 g, 14.99 mmol), and the mixture was refluxed for 24 hours, After the operation, the temperature was lowered to room temperature. The resulting solid was separated by filtration, washed thoroughly in the order of water / methanol / hexane, and the resulting solid was dried in a vacuum oven to obtain 9.2 g (77%) of compound M2C.

Synthesis of Compound M1C

To the compound M2C (4.91 g, 3.07 mmol) was added 45 mL of MC and then AgOTf (1.58 g, 6.13 mmol) was dissolved in 15 mL of methanol and added. Thereafter, the mixture was stirred at room temperature for 18 hours while blocking the light with aluminum foil, and the reaction was allowed to proceed. Then, the resulting solid was removed by filtration through Celite, and the filtrate was reduced in pressure to obtain a solid (Compound M1C) And used for the next reaction.

Synthesis of Compound 97

80 mL of ethanol was mixed with compound M1C (6 g, 6.14 mmol) and 2-phenylpyridine (1.14 g, 7.36 mmol), and the mixture was stirred at reflux for 18 hours to lower the temperature. The resulting mixture was filtered, and the obtained solid was sufficiently washed with ethanol and hexane, and subjected to column chromatography under MC: hexane to obtain 0.96 g (15%) of Compound 97. Mass and HPLC analysis confirmed the material.

HRMS (MALDI) calcd for C ₄₉ H ₄₀ IrN ₃ Si ₂ : m / z 919.2390, Found: 919.2385

Synthesis Example 4: Synthesis of Compound 116

70 mL of ethanol was mixed with Compound M1C (6 g, 6.14 mmol) and Compound B (1.67 g, 7.36 mmol), and the mixture was stirred at reflux for 18 hours to lower the temperature. The resulting mixture was filtered, and the obtained solid was sufficiently washed with ethanol and hexane, and subjected to column chromatography under MC: hexane to obtain 1.39 g (23%) of Compound 116. Mass and HPLC analysis confirmed the material.

HRMS (MALDI) calcd C ₅₂ H ₄₈ IrN ₃ Si ₃ : m / z 991.2785, Found: 991.2781

Synthesis Example 5: Synthesis of Compound 120

70 mL of ethanol was mixed with Compound M1C (6 g, 6.14 mmol) and Compound C (2.09 g, 7.36 mmol), and the mixture was refluxed with stirring for 18 hours. The resulting mixture was filtered, and the obtained solid was sufficiently washed with ethanol and hexane, and subjected to column chromatography under MC: hexane to obtain 0.92 g (14%) of Compound 120. Mass and HPLC analysis confirmed the material.

HRMS (MALDI) calcd for C ₅₆ H ₅₆ IrN ₃ Si ₃ : m / z 1047.3411, Found: 1047.3414

Synthesis Example 6: Synthesis of Compound 138

50 mL of ethoxyethanol was mixed with 4.00 g of compound M1C and 2.00 g of acetylacetone (2.90 g, 28.93 mmol) and K ₂ CO ₃ (4.00 g, 28.93) The reaction was allowed to proceed with stirring at &lt; RTI ID = 0.0 &gt; 0 C &lt; / RTI &gt; The resulting mixture was filtered, and the resulting solid was sufficiently washed with ethanol and hexane, and subjected to column chromatography under MC conditions to obtain 0.90 g (11%) of Compound 138. Mass and HPLC analysis confirmed the material.

HRMS (MALDI) calcd for C ₄₃ H ₃₉ IrN ₂ O ₂ Si ₂ : m / z 864.2179, Found: 864.2177

Synthesis Example 7: Synthesis of Compound 140

50 mL of 2-ethoxyethanol was mixed with Compound A (4.51 g, 15.69 mmol) and Ir (COD) ₂ BF ₄ (2.36 g, 4.76 mmol) and the reaction was stirred at 120 ° C for 18 hours. Lower the temperature and filter to obtain a solid. Column chromatography was carried out under MC: hexane to obtain 0.4 g (8%) of compound 140. Mass and HPLC analysis confirmed the material.

HRMS (MALDI) calcd for C ₅₇ H ₄₈ IrN ₃ Si ₃ : m / z 1051.2785, Found: 1051.2779

Example 1

The ITO glass substrate was cut into a size of 50 mm x 50 mm x 0.5 mm, ultrasonically cleaned in acetone isopropyl alcohol and pure water for 15 minutes each, and then subjected to UV ozone cleaning for 30 minutes.

Subsequently, m-MTDATA was deposited on the ITO electrode (anode) on the glass substrate at a deposition rate of 1 Å / sec to form a hole injection layer having a thickness of 600 Å, and α-NPD was deposited on the hole injection layer at a deposition rate of 1 Å / sec To form a hole transporting layer having a thickness of 250 ANGSTROM.

Compound 1 (dopant) and CBP (host) were co-deposited on the hole transporting layer at deposition rates of 0.1 Å / sec and 1 Å / sec, respectively, to form a 400 Å thick light emitting layer.

Alq ₃ was deposited on the hole blocking layer to form an electron transporting layer having a thickness of 300 A, and then an electron transport layer having a thickness of 50 Å was formed on the electron transporting layer by depositing LiF M-MTDATA (600 Å) / α-NPD (600 Å) was formed by vacuum evaporation of Al on the electron injection layer to form a second electrode (cathode) (250 Å) / CBP + 10% (Compound 1) (400 Å) / Balq (50 Å) / Alq ₃ (300 Å) / LiF (10 Å) / Al (1200 Å).

Examples 2 to 7 and Comparative Example 1

An organic light emitting device was fabricated in the same manner as in Example 1 except that the compound shown in Table 2 was used instead of Compound 1 as a dopant in the light emitting layer formation.

Evaluation Example 1: Characteristic evaluation of organic light emitting device

The driving voltage, current efficiency, power efficiency, color coordinates, and external quantum efficiency were evaluated for each of the organic light emitting devices manufactured in Examples 1 to 7 and Comparative Example 1 at a required luminance of 6000 cd / m ² , Respectively. A current-voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as evaluation devices.

Dopant Driving
Voltage
(V) efficiency
(cd / A) power
(Im / W) CIEx CIEy quantum
efficiency
(%) Example 1 One 6.2 55.0 27.9 0.59 0.36 18 Example 2 11 6.3 56.5 28.2 0.60 0.36 19 Example 3 97 6.3 57.0 28.4 0.61 0.36 19 Example 4 116 6.2 57.0 28.9 0.61 0.35 19 Example 5 120 6.2 55.0 27.9 0.59 0.36 18 Example 6 138 6.2 54.0 27.3 0.58 0.36 19 Example 7 140 6.2 57.0 28.9 0.61 0.36 18 Comparative Example 1 Ir (ppy) ₃ 6.5 40.2 19.4 0.330 0.604 18

From Table 2, it can be seen that the organic light emitting devices of Examples 1 to 7 have excellent driving voltage, current efficiency, power efficiency and color coordinates as compared with the organic light emitting device of Comparative Example 1. [

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}
(2)

M in the above formula (1) may be at least one selected from the group consisting of Ir, Ir, Pt, Os, Ti, Zr, And rhodium (Rh)
Wherein L ₁ is selected from the ligands represented by the above formula (2), n 1 is 1, 2 or 3, and when n ₁ is 2 or more, L ₁ is the same or different from each other,
Wherein L ₂ is selected from a monovalent organic ligand, a divalent organic ligand, a trivalent organic ligand and a tetravalent organic ligand, n 2 is 0, 1, 2, 3 or 4, L < _{2 &gt}; are the same or different from each other,
Chemical Formula ₁ L 1 and L ₂ are different from each other,
Formula 2 of CY ₁₁ is selected from C ₅ -C ₃₀ carbocyclic ring, C ₂ -C ₃₀ heterocyclic ring,
In Formula 2, R ₁ to R ₃ and R ₁₁ to R ₁₃ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , a hydroxyl group, a cyano group, A substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₃₀ alkyl group, a substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₃₀ alkenyl 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 ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C _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, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, 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 ah Group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic condensed polycyclic _{group, -Si (Q 1) (Q} 2) (Q 3), -N (Q ₄₎ is selected from _{(Q 5), -B (Q} 6) (Q 7) , and _{-P (= O) (Q 8} ) (Q 9),
B1 in Formula 2 is an integer selected from 0 to 3,
B2 in Formula 2 is an integer selected from 0 to 4,
B3 and b5 in the general formula (2) are independently an integer selected from 1 to 3,
At least one R ₃ of Formula 2 is linked to at least one R ₁₃ to form a substituted or unsubstituted saturated or unsaturated C ₂ -C ₃₀ cyclic ring,
* And * in the above formula (2) 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,
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkenyl group, an amino group, an amidino group, a hydrazine group, An alkynyl group and a C ₁ -C ₆₀ alkoxy group;
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ heterocycloalkyl group, 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, 1 is a non-condensed polycyclic aromatic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -Si (Q 11) (Q} 12) (Q 13), -N (Q 14) (Q 15), -B (Q ₁₆₎ (Q ₁₇₎ and _{-P (= O) (Q 18} ) (Q 19) from the at least one selected substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, 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;
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkenyl group, an amino group, an amidino group, a hydrazine group, 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 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 group condensed polycyclic _{, -Si (Q 21) (Q} 22) (Q 23), -N (Q 24) (Q 25), -B (Q 26) (Q 27) and _{-P (= O) (Q 28} ) (Q _A C ₃ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkenyl group substituted with at least one selected from the group consisting of a C ₁ -C ₁₀ cycloalkyl 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 A heterocyclic polycyclic group; And
_{-Si (Q 31) (Q 32} ) (Q 33), -N (Q 34) (Q 35), -B (Q 36) (Q 37) and _{-P (= O) (Q 38} ) (Q 39 );
;
Wherein Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ independently of one another are hydrogen, deuterium, -F, -Cl, -Br, -I, A nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, 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 ₃ -C ₁₀ cycloalkyl group, a substituted Or 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, a substituted or unsubstituted C ₆ -C ₁₀ heterocycloalkyl group, 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 ring Heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group. The method according to claim 1,
Wherein M is Ir and n1 + n2 is 3; or
M is Pt, and n1 + n2 is 2. 2. The organometallic compound according to claim 1, The method according to claim 1,
CY ₁₁ in the above-mentioned formula (2) is at least one selected from the group consisting of benzene, indene, naphthalene, azulene, hethalene, indacene, acenaphthylene, fluorene, spiro- fluorene, benzofluorene, dibenzofluorene, phenalene, Anthracene, indolene, indolene, indolene, anthracene, fluoranthene, triphenylene, pyrene, klysene, naphthacene, pisene, perylene, pentacene, hexacene, pentacene, rubisene, Benzothiazole, benzofuran, benzothiophene, benzothiophene, benzothiophene, benzothiophene, benzothiophene, benzothiophene, benzothiophene, benzothiophene, benzothiophene, Which is selected from the group consisting of benzene, benzene, benzene, benzene, benzene, benzene, benzene, benzene, Metal compound. The method according to claim 1,
R ₁₁ to R ₁₃ in the general formula (2)
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof ₂₀ alkoxy group, a phosphoric acid group or a salt thereof, -SF _5, C ₁ -C ₂₀ alkyl group and C ₁ -C;
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, An amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a C ₁ -C ₁₀ alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, A cyclopentenyl group, a cyclopentenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group, each of which is optionally substituted with one or more groups selected from the group consisting of an alkyl group, an ethyl group, an ethyl group, an ethyl group, an octyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one selected;
A cyclopentyl group, a cyclohexyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a crycenyl group, a pyrrolyl group, a thiophenyl group, a furanyl 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, a quinolinyl group, an isoquinolinyl group, an isoxazolyl group, an isoxazolyl group, Benzoquinolyl groups, benzoquinolyl groups, benzoquinolyl groups, benzoquinolyl groups, quinoxalinyl groups, quinazolinyl groups, cinolinyl groups, carbazolyl groups, phenanthrolinyl groups, benzoimidazolyl groups, benzofuranyl groups, benzothiophenyl groups, A benzoxazolyl group, a triazolyl group An oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group;
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, Cyclohexyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, phenanthrenyl group, phenanthrenyl group, phenanthrenyl group, phenanthrenyl group, A thiophene group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, a thiophenol group, , Isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, A benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, an isoquinolinyl group, Benzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranoyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzoyl group A cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, a cyclohexyl group, a carbazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group, A cyclopentenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an imidazolyl 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 benzofuranyl 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 dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; And
_{-B (Q 6) (Q 7} ) , and _{-P (= O) (Q 8} ) (Q 9);
&Lt; / RTI &gt;
Q ₆ to Q ₉ are, independently of each other,
-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;
n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And
Deuterium, C ₁ -C ₁₀ alkyl group and the phenyl group selected from the at least one substituted, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, An isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;
&Lt; / RTI &gt; The method according to claim 1,
R ₁₁ to R ₁₃ in the general formula (2)
An alkyl group having 1 to 10 carbon atoms which may be substituted with at least one substituent selected from the group consisting of hydrogen, deuterium, -F, cyano, nitro, -SF ₅ , methyl, ethyl, n-propyl, isopropyl, An n-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, an isobutyl group, an isobutyl group, , a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, a n-nonyl group, an isononyl group, a secononyl group, A cyclohexyl group, a cyclohexyl group, an adamantanyl group, a norbornane group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, a cycloheptyl group, a cycloheptyl group, a cyclopentyl group, A norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group;
Heavy _{hydrogen, -F, -CD 3, -CD 2} H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, cyano, nitro, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy A cyclohexyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridyl group, a cyclopentyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbonanyl group, N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl and iso Heptyl, sec-pentyl, n-hexyl, isohexyl, sec-hexyl, , n-octyl group, iso-octyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, secononyl group, tert- A tertiary-decyl group, a methoxy group, an ethoxy group, a propoxy group, A cyclopentyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbonanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group , A pyridinyl group and a pyrimidinyl group; And
_{-B (Q 6) (Q 7} ) , and _{-P (= O) (Q 8} ) (Q 9);
&Lt; / RTI &gt;
Q ₆ to Q ₉ are, independently of each other,
-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;
n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And
Deuterium, C ₁ -C ₁₀ alkyl group and the phenyl group selected from the at least one substituted, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, An isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;
&Lt; / RTI &gt; The method according to claim 1,
In the formula (2), R ₁ to R ₃ are, independently of each other,
C ₁ -C ₁₀ alkyl group, a phenyl group and a _{-Si (Q 1) (Q 2} ) (Q 3); And
Heavy hydrogen and C ₁ -C _10, at least one a, C ₁ -C ₁₀ alkyl group and a substituted phenyl group selected from the group;
&Lt; / RTI &gt;
Q ₁ to Q ₃ are, independently of each other,
-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;
n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And
Deuterium, C ₁ -C ₁₀ alkyl group and the phenyl group selected from the at least one substituted, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, An isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;
&Lt; / RTI &gt; The method according to claim 1,
R ₁₁ to R ₁₃ in Formula 2 are independently selected from the group consisting of hydrogen, deuterium, -F, cyano, nitro, -SF ₅ , -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , groups represented by the following formulas (9-1) to (9-19), and groups represented by the following formulas (10-1)
In the formula (2), R ₁ to R ₃ are, independently of each other,
-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;
butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and -Si (Q ₁ ) (Q ₂ ) (Q ₃ ); And
At least selected from the group consisting of heavy hydrogen and C ₁ -C ₁₀ alkyl group substituted with one, n- propyl, isopropyl, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, an isopentyl A sec-pentyl group, a tert-pentyl group and a phenyl group;
&Lt; / RTI &gt;
Q ₁ to Q ₃ are, independently of each other,
-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;
n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And
Deuterium, C ₁ -C ₁₀ alkyl group and the phenyl group selected from the at least one substituted, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, An isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;
&Lt; / RTI &gt;

In Formulas (9-1) to (9-17) and (10-1) to (10-30), * denotes a bonding site with neighboring atoms. The method according to claim 1,
Chemical Formula 1 L ₁ of this ligand selected from represented by the formula 2-1 to 2-6, the organic metal compound:

The description of CY ₁₁ , R ₁ , R ₂ , R ₁₁ , R ₁₂ , b 1 and b _{2 in} the general formulas (2-1) to (2-6)
CY ₂ is a saturated or unsaturated C ₂ -C ₃₀ cyclic ring formed by connecting R ₃ and R ₁₃ to each other,
The description of R ₂₁ is the same as that for R ₁₁ ,
b11 is selected from an integer of 0 to 10,
* And * 'are binding sites for M in formula (1). 9. The method of claim 8,
CY ₂ is selected from the group consisting of silolane, 2,3-dihydro-1H-silole, 2,5-dihydro-1H- silole, 3,4-dihydro-2H-silole, silole, 2,3-dihydro-1H-benzo [b] 1-H-benzo [b] silole, benzosiliole, silinane, tetrahydrosiline, dihydrosiline, tetrahydrobenzosiline and dihydrobenzosiline. ). &Lt; / RTI &gt; The method according to claim 1,
The following general formula (1) is of L ₁ selected from the group consisting of ligands represented by formula (2) (1) to 2 (36), an organometallic compound:

Among the above-mentioned structural formulas (2A) to (36)
R ₁ , R ₂ , R ₁₁ , R ₁₂ , b 1 and b 2 are as defined in claim 1,
The description of R ₂₁ is the same as that for R ₁₁ ,
b11 is selected from an integer of 0 to 6,
* And * 'are binding sites for M in formula (1). 11. The method of claim 10,
L ₁ in the above formula (1) is selected from the group represented by the formulas (2), (3), (4), 2 (6), 2 (9), 2 (12), 2 (27) ,
Of the above formulas 2 (3), 2 (4), 2 (6), 2 (9), 2 (12), 2 (27)
CY &lt; ₁₁ &gt; is benzene or naphthalene,
R ₁₁ , R ₁₂ and R ₂₁ are, independently of each other,
An alkyl group having 1 to 10 carbon atoms which may be substituted with at least one substituent selected from the group consisting of hydrogen, deuterium, -F, cyano, nitro, -SF ₅ , methyl, ethyl, n-propyl, isopropyl, An n-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, an isobutyl group, an isobutyl group, , a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, a n-nonyl group, an isononyl group, a secononyl group, A cyclohexyl group, a cyclohexyl group, an adamantanyl group, a norbornane group, a cyclopentyl group, a cyclopentyl group, a cyclopentyl group, a cycloheptyl group, a cycloheptyl group, a cyclopentyl group, A norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group;
Heavy _{hydrogen, -F, -CD 3, -CD 2} H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, cyano, nitro, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy A cyclohexyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridyl group, a cyclopentyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbonanyl group, N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl and iso Heptyl, sec-pentyl, n-hexyl, isohexyl, sec-hexyl, , n-octyl group, iso-octyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, secononyl group, tert- A tertiary-decyl group, a methoxy group, an ethoxy group, a propoxy group, A cyclopentyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbonanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group , A pyridinyl group and a pyrimidinyl group; And
_{-B (Q 6) (Q 7} ) , and _{-P (= O) (Q 8} ) (Q 9);
&Lt; / RTI &gt;
Q ₆ to Q ₉ are, independently of each other,
-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;
n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And
Deuterium, C ₁ -C ₁₀ alkyl group and the phenyl group selected from the at least one substituted, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, An isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;
&Lt; / RTI &gt;
R ₁ and R ₂ are, independently of each other,
-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;
n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And
Deuterium, C ₁ -C ₁₀ alkyl group and the phenyl group selected from the at least one substituted, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, An isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;
&Lt; / RTI &gt; The method according to claim 1,
The formula to the L ₁ of the first formula 2A-1 to 2A-10, 2B-1 to 2B-10, 2C-1 to 2C-10, 2D-1 to 2D-10, 2E-1 to 2E-10, 2F -1 to 2F-10, and 2G-1 to 2G-10.

2E-1 to 2E-10, 2F-1 to 2F-10 and 2F-1 to 2F-10 and 2C-1 to 2C-10, Among 2G-1 to 2G-10
R ₁₂ and R _12a to R _12d are each independently selected from the group consisting of deuterium, -F, cyano, nitro, -SF ₅ , -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , CF ₂ H, -CFH ₂ , groups represented by the following formulas (9-1) to (9-19), and groups represented by the following formulas (10-1) to
R ₁ and R ₂ are, independently of each other,
-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;
butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and -Si (Q ₁ ) (Q ₂ ) (Q ₃ ); And
At least selected from the group consisting of heavy hydrogen and C ₁ -C ₁₀ alkyl group substituted with one, n- propyl, isopropyl, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, an isopentyl A sec-pentyl group, a tert-pentyl group and a phenyl group;
&Lt; / RTI &gt;
Q ₁ to Q ₃ are, independently of each other,
-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;
n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And
Deuterium, C ₁ -C ₁₀ alkyl group and the phenyl group selected from the at least one substituted, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, An isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;
&Lt; / RTI &gt;
* And * 'are binding sites for M in formula (1)

The method according to claim 1,
Wherein L &lt; ₂ &gt; in the general formula (1) is selected from ligands represented by the following general formulas (3A) to (3G)

In the above formulas (3A) to (3G)
Y ₁₁ to Y ₁₆ are independently of one another carbon (C) or nitrogen (N), Y ₁₁ and Y ₁₂ are connected to each other by a single bond or a double bond, Y ₁₃ and Y ₁₄ are a single bond or a double bond Y ₁₅ and Y ₁₆ are connected to each other by a single bond or a double bond,
CY CY ₃ to ₅ are independently selected from, C ₅ -C ₆₀ carbocyclic group, and C ₂ -C ₆₀ heterocyclic group upon each other,
a1 to a3 are each independently selected from an integer of 1 to 5,
A &lt; ₁ &gt; is P or As,
(R ₃₄ ), P (R ₃₅ ) (R ₃₆ ), and As (R ₃₇ ) (R ₃₈ ), X _11a , X _11b , X _12a , X _12b , X _13a and X _13b are, ), With the proviso that X _12a , X _12b , X _13a and X _13b are not N and O,
R _{33 "} and R _34" are, independently of each other, a single bond, a double bond, a substituted or unsubstituted C ₁ -C ₅ alkylene group, a substituted or unsubstituted C ₂ -C ₅ alkenylene group and a substituted or unsubstituted C ₆ -C ₁₀ arylene group,
Z ₁ to _{Z 3, R 31, R 32a} , R 32b, R 32c, R 33a, R 33b, R 34 to R ₃₈ and R _35a, R _35b, R _35c and R _35d are each independently hydrogen, deuterium, A sulfonyl group or a salt thereof, a phosphoric acid group or a phosphoric acid group or a salt thereof, or a salt thereof, 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 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 come 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 aryl tea, Substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic condensed polycyclic group, -Si (Q ₁₎ ( is selected from _{Q 2) (Q 3),} -N (Q 4) (Q 5), -B (Q 6) (Q 7) , and _{-P (= O) (Q 8} ) (Q 9),
* And * 'are binding sites for M in formula (1)
The substituted C ₁ -C ₅ alkylene group, the substituted C ₂ -C ₅ alkenylene group, the substituted C ₆ -C ₁₀ arylene group, the substituted C ₁ -C ₆₀ alkyl group, the substituted C ₂ -C ₆₀ alkenyl group , A substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cyclo alkenyl group, a substituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl groups, substituted monovalent non-aromatic condensed polycyclic groups, and substituted monovalent non-aromatic hydrocarbon ring, at least one of the substituents of the fused polycyclic group,
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkenyl group, an amino group, an amidino group, a hydrazine group, An alkynyl group and a C ₁ -C ₆₀ alkoxy group;
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ heterocycloalkyl group, 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, 1 is a non-condensed polycyclic aromatic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -Si (Q 11) (Q} 12) (Q 13), -N (Q 14) (Q 15), -B (Q ₁₆₎ (Q ₁₇₎ and _{-P (= O) (Q 18} ) (Q 19) from the at least one selected substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, 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;
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkenyl group, an amino group, an amidino group, a hydrazine group, 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 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 group condensed polycyclic _{, -Si (Q 21) (Q} 22) (Q 23), -N (Q 24) (Q 25), -B (Q 26) (Q 27) and _{-P (= O) (Q 28} ) (Q _A C ₃ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkenyl group substituted with at least one selected from the group consisting of a C ₁ -C ₁₀ cycloalkyl 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 A heterocyclic polycyclic group; And
_{-Si (Q 31) (Q 32} ) (Q 33), -N (Q 34) (Q 35), -B (Q 36) (Q 37) and _{-P (= O) (Q 38} ) (Q 39 );
;
Wherein Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ independently of one another are hydrogen, deuterium, -F, -Cl, -Br, -I, A nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, 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 ₃ -C ₁₀ cycloalkyl group, a substituted Or 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, a substituted or unsubstituted C ₆ -C ₁₀ heterocycloalkyl group, 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 ring Heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group. 14. The method of claim 13,
Wherein L &lt; ₂ &gt; is selected from the ligands represented by the above formulas (3A), (3B) and (3F)
Wherein Y ₁₁ is nitrogen,
Y ₁₂ to Y ₁₄ in the formula (3A) are carbon,
3A of the general formula CY ₃ is pyridine, 5,6,7,8-tetrahydro-quinoline (5,6,7,8-tetrahydroquinoline), 5,6,7,8-tetrahydroisoquinoline (5,6,7 , 8-tetrahydroisoquinoline), quinoline and isoquinoline,
CY ₄ in the above-mentioned formula (3A) is preferably selected from the group consisting of benzene, 1,2,3,4-tetrahydronaphthalene, naphthalene, fluorene, dibenzofuran, dibenzothiophene, benzofuropyridine, and benzothienopyridine,
In Formula 3B, Y &lt; ₁₅ &gt; is carbon,
And Y ₁₆ is a nitrogen of the Formula 3B,
CY &lt; ₅ &gt; in the above formula (3B) is pyridine or pyrimidine,
Z ₁ to Z ₃ in the above formulas (3A) and (3B)
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof ₂₀ alkoxy group, a phosphoric acid group or a salt thereof, -SF _5, C ₁ -C ₂₀ alkyl group and C ₁ -C;
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, An amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a C ₁ -C ₁₀ alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, octyl group, Ada manta group, Nord Bona group, Nord Bonnet group, a cyclopentenyl group, a cyclohexenyl group, a cycloalkyl heptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group with at least one substitution selected from the group consisting of C ₁ - A C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;
A cyclopentyl group, a cyclohexyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a crycenyl group, a pyrrolyl group, a thiophenyl group, a furanyl 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, a quinolinyl group, an isoquinolinyl group, an isoxazolyl group, an isoxazolyl group, Benzoquinolyl groups, benzoquinolyl groups, benzoquinolyl groups, benzoquinolyl groups, quinoxalinyl groups, quinazolinyl groups, cinolinyl groups, carbazolyl groups, phenanthrolinyl groups, benzoimidazolyl groups, benzofuranyl groups, benzothiophenyl groups, A benzoxazolyl group, a triazolyl group An oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group;
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, A cyclopentenyl group, a cycloheptenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, a cyclopentenyl group, a cycloheptyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbonanyl group, A thiazolyl group, an isothiazolyl group, an isothiazolyl group, an isothiazolyl group, an isothiazolyl group, an isothiazolyl group, an isothiazolyl group, an isothiazolyl group, a thiazolyl group, a thiazolyl group, An isoindolyl group, an indolyl group, an indazolyl group, a furyl group, an isothiazolyl group, an imidazolyl group, an imidazolyl group, a pyridazinyl group, A benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, A thiazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranoyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a di-benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, A cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, an imidazopyrimidinyl group, an imidazopyrimidinyl group, a cyclopentyl group, , A cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an imidazolyl 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 benzofuranyl 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 dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; And
_{-Si (Q 1) (Q 2} ) (Q 3), -N (Q 4) (Q 5), -B (Q 6) (Q 7) , and _{-P (= O) (Q 8} ) (Q 9 );
&Lt; / RTI &gt;
a1 to a3 are independently an integer selected from 0 to 4,
A1 of the Z _1, Z _2, a2 and a2 of the two Z 2 or ₃ of neighboring substituents optionally (optionally), combine with each other C ₅ -C ₃₀ carbocyclic group, or C ₂ -C ₃₀ heterocyclic group, Lt; / RTI &gt;
Wherein Q ₁ to Q ₉ are, independently of each other,
-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;
n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And
At least selected from the group consisting of heavy hydrogen and C ₁ -C ₁₀ alkyl group substituted with one, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, an isopentyl A sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;
&Lt; / RTI &gt;
X _12a and X _12b in Formula 3F are O,
In the above formula (3F), R _"
A C ₂ -C ₅ alkenylene group; And
A C ₂ -C ₅ alkenylene group substituted with at least one selected from deuterium, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group and a phenyl group;
&Lt; / RTI &gt; The method according to claim 1,
Formula 1 L ₂ of the following Formula 3-1 (1) to 3-1 (60) 3-1 (61) to 3-1 (69) 3-1 (71) to 3-1 (79) , 3-1 (81) to 3-1 (88), 3-1 (91) to 3-1 (98), 3-111 and 3-112,

3-1 (61) to 3-1 (69), 3-1 (71) to 3-1 (79), 3-1 (81) To 3-1 (88), 3-1 (91) to 3-1 (98), 3-111 and 3-112,
_{Z 1, Z 2, Z 1a} , Z 1b, Z 1c, Z 1d, Z 2a, Z 2b, Z 2c, Z 2d, R 34a, R 34b and R _34c are independently of one another, deuterium, -F, a cyano group , a nitro _{group, -SF 5, -CH 3, -CD} 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, -Si (Q 1) (Q 2) (Q _3), a _{-N (Q 4) (Q 5} ), -B (Q 6) (Q 7), -P (= O) (Q 8) (Q 9), the following formulas 9-1 to 9-19 A group to be displayed and a group represented by the following general formulas (10-1) to (10-30)
X ₁ is O, S, C (Z ₂₁ ) (Z ₂₂ ) or N (Z ₂₃ )
Z ₃ , Z ₁₁ to Z ₁₃ and Z ₂₁ to Z ₂₃ independently of one another are hydrogen, deuterium, -F, cyano, nitro, -SF ₅ , -CH ₃ , -CD ₃ , -CD ₂ H, _{CDH 2, -CF 3, -CF 2} H, -CFH 2, -Si (Q 1) (Q 2) (Q 3), -N (Q 4) (Q 5), -B (Q 6) (Q _{7), -P (= O)} (Q 8) (Q 9), to a group and represented by the formula 9-1 to 9-19 is selected from the group represented by the formula 10-1 to 10-30,
Wherein Q ₁ to Q ₉ are, independently of each other,
-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H _{, -CHDCDH 2, -CHDCD 3, -CD} 2 CD 3, -CD 2 CD 2 H , and -CD ₂ CDH _2;
n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Tilyl group; And
At least selected from the group consisting of heavy hydrogen and C ₁ -C ₁₀ alkyl group substituted with one, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n- pentyl group, an isopentyl A sec-pentyl group, a tert-pentyl group, a phenyl group and a naphthyl group;
&Lt; / RTI &gt;
d2 and e2 are, independently of each other, 0 or 2,
e3 is an integer selected from 0 to 3,
d4 and e4 are, independently of each other, an integer selected from 0 to 4,
d6 and e6 are, independently of each other, an integer selected from 0 to 6,
d8 and e8 are, independently of each other, an integer selected from 0 to 8,
* And * 'are binding sites for M in formula (1)

The method according to claim 1,
An organometallic compound, which is one of the following compounds 1 to 270:

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 of the organometallic compounds of any one of claims 1 to 16. 18. The method of claim 17,
Wherein the first electrode is an anode,
The second electrode is a cathode,
Wherein the organic layer includes a hole transporting region interposed between the first electrode and the light emitting layer, and an electron transporting region interposed between the light emitting layer and the second electrode,
Wherein the hole transporting region includes at least one selected from a hole injecting layer, a hole transporting layer, and an electron blocking layer,
Wherein the electron transporting region includes at least one selected from a hole blocking layer, an electron transporting layer, and an electron injecting layer. 18. The method of claim 17,
Wherein the organic metal compound is contained in the light emitting layer. 18. The organic light emitting device according to claim 17, wherein the light emitting layer further comprises a host, and the content of the host is larger than the content of the organic metal compound.

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