KR20180094482A - Organometallic compound, organic light emitting device including the same and a composition for diagnosing including the same - Google Patents

Abstract

Disclosed are an organometallic compound, an organic light-emitting device containing the organometallic compound, and a diagnostic composition containing the organometallic compound. To this end, the organometallic compound is represented by chemical formula 1. According to the present invention, it is possible to provide the diagnostic composition having high diagnostic efficiency.

Description

TECHNICAL FIELD The present invention relates to an organic electroluminescent device, an organic electroluminescent device including the organic electroluminescent device,

Organic metal compounds, organic light emitting devices including the same, and diagnostic compositions including the organic light emitting devices are disclosed.

BACKGROUND ART An organic light emitting device is a self light emitting type device having excellent viewing angle, response time, luminance, driving voltage, and response speed, and can be multi-colored.

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.

On the other hand, a luminescent compound, for example, a phosphorescent luminescent compound can also be used for monitoring, sensing, and detecting biological materials such as various cells and proteins.

A novel organic metal compound, an organic light emitting device employing the same, and a diagnostic composition employing the same.

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

≪ Formula 1 >

In Formulas 1 and 2A to 2D,

M is palladium (Pd), platinum (Pt), or gold (Au)

X ₁ is O or S, the bond between M and X ₁ is a covalent bond,

X ₂ is N, X ₃ and X ₄ are independently of each other C or N,

The bond between M and X ₂ , the bond between M and X _3, and the bond between M and X ₄ are coordinate bond and the remaining one is a covalent bond,

Y ₁ to Y ₇ are independently of each other C or N,

Y ₈ and Y ₉ are independently of each other C, N, O or S,

A bond between Y ₁ and Y ₈ or an atomic group and a bond or an atomic group between Y ₁ and Y ₂ constitute CY ₁ and a bond or an atomic group between X ₂ and Y ₃ and a bond or an atomic group between X ₂ and Y ₄ CY ₂ , the bond between X ₃ and Y ₅ or the atomic group and the bond or atomic group between X ₃ and Y ₆ constitute CY ₃ , the bond or atomic group between X ₄ and Y _7, and the bond between X ₄ and Y ₉ Or the atomic group constitutes CY ₄ ,

CY ₁ to CY ₄ are independently selected from a C ₅ -C ₃₀ carbocyclic group and a C ₁ -C ₃₀ heterocyclic group,

T ₁ is _{* -N [(L 61) a61} - (R 61)] - * ', * -B (R 61) - *', * -P (R 61) - * ', * -C (R 61 _{) (R 62) - * '} , * -Si (R 61) (R 62) - *', * -Ge (R 61) (R 62) - * ', * -S- *', * -Se- * ', * -O- *', * -C (= O) - * ', * -S (= O) - *', * -S (= O) 2 - * ', * -C (R 61 ) = * ', * = C (R 61) - *', * -C (R 61) = C (R 62) - * ', * -C (= S) - *' and * -C≡C- * &Quot;,"

T ₂ is _{* -N [(L 63) a63} - (R 63)] - * ', * -B (R 63) - *', * -P (R 63) - * ', * -C (R 63 _{) (R 64) - * '} , * -Si (R 63) (R 64) - *', * -Ge (R 63) (R 64) - * ', * -S- *', * -Se- * ', * -O- *', * -C (= O) - * ', * -S (= O) - *', * -S (= O) 2 - * ', * -C (R 63 ) = * ', * = C (R 63) - *', * -C (R 63) = C (R 64) - * ', * -C (= S) - *' and * -C≡C- * &Quot;,"

T ₃ is _{* -N [(L 65) a65} - (R 65)] - * ', * -B (R 65) - *', * -P (R 65) - * ', * -C (R 65 _{) (R 66) - * '} , * -Si (R 65) (R 66) - *', * -Ge (R 65) (R 66) - * ', * -S- *', * -Se- * ', * -O- *', * -C (= O) - * ', * -S (= O) - *', * -S (= O) 2 - * ', * -C (R 65 ) = * ', * = C (R 65) - *', * -C (R 65) = C (R 66) - * ', * -C (= S) - *' and * -C≡C- * &Quot;,"

L ₆₁ , L ₆₃ and L ₆₅ are each independently selected from a single bond, a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

a61, a63, and a65 is selected from 1 to 3, independently of one another, a61 this case, 2 or more, two or more of L ₆₁ are to each other the same or different, and a63 in this case 2 or more, two or more of L ₆₃ may be the same or different, and a65 each other Is 2 or more, two or more L < ₆₅ > s are the same or different from each other,

R ₆₁ and R ₆₂ are, optionally, bonded to each other through a first connecting group to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group, or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group, You can,

R ₆₃ and R ₆₄ are optionally joined to one another through a first linking group to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group You can,

R ₆₅ and R ₆₆ are optionally joined to one another through a first linking group to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group You can,

b1 to b3 independently of one another are 0, 1, 2 or 3 and when b1 is 0, * - (T ₁ ) _b1 - * is a single bond, and when b2 is 0 * - (T ₂ ) _b2 - * is a single bond, and when b3 is 0, * - (T ₃ ) _{b 3} - * '

Z ₁ to Z ₄ are independently selected from the group consisting of the group represented by the formula (2A), the group represented by the formula (2B), the group represented by the formula (2C) and the group represented by the formula (2)

c1 to c4 are independently selected from the integers of 0 to 5, the sum of c1 to c4 is 1 or more,

R ₁ to R ₄ , R ₅₁ to R ₅₃ and R ₆₁ to R ₆₆ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , a hydroxyl group, A substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆ alkyl group, a substituted or unsubstituted C ₂ -C ₆ alkenyl group, a substituted or unsubstituted C ₂ -C ₆ 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 group, a substituted addition A condensed polycyclic aromatic group, a substituted or unsubstituted non-1-unsubstituted monovalent condensed polycyclic non-aromatic heterocyclic _{group, -N (Q 1) (Q} 2), -Si (Q 3) (Q 4) (Q _{5), -B (Q 6)} (Q 7) , and _{-P (= O) (Q 8} ) (Q 9) doedoe selected from, however, are each independently of the formula (2A) R ₅₁ and R _52, substituted or unsubstituted 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 heterocyclo A substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent heterocyclic group Is selected from non-aromatic heterocyclic polycyclic groups,

a1 to a4 are each independently selected from integers of 0 to 5,

two of a1 of R ₁ is optionally, be connected to each other, may form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group, or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

two of a2 of R ₂ is optionally, be connected to each other, may form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group, or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

two of a3 of R ₃ is optionally, be connected to each other, may form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group, or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

two of a4 of R ₄ is optionally, be connected to each other, may form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group, or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

Two or more of the neighboring R ₁ to R ₄ may optionally be bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group Can,

Two of R ₅₁ to R ₅₃ may optionally be bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group ,

* Is the binding site with neighboring atoms,

The substituted C ₅ -C ₃₀ carbocyclic group, a substituted C ₁ -C ₃₀ heterocyclic group, a substituted C ₁ -C ₆₀ alkyl group, a substituted C ₂ -C ₆₀ alkenyl, substituted C ₂ -C _A substituted C ₁ -C ₆ 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 cycloalkenyl group, a substituted C ₁ -C ₁₀ cycloalkenyl group, -C ₁₀ hetero 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, , The substituted monovalent non-aromatic condensed polycyclic group and the substituted 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 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, an amidino group, a hydrazine group, a hydrazone jongi, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, 1 (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, and C _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 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 condensed polycyclic group, - _{N (Q 21) (Q 22} ), -Si (Q 23) (Q 24) (Q 25), -B (Q 26) (Q 27) and _{-P (= O) (Q 28} ) (Q 29) at least one selected from the substituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ Group-, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic group, fused polycyclic; 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 );

≪ / 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, group, a nitro group, an amidino group, a hydrazine group, a hydrazone jongi, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ alkyl and C ₆ -C ₆₀ aryl group, at least one substituted C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group of, C ₆ -C ₆₀ aryl A C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a 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 and including a light emitting layer, wherein the organic layer includes at least one of the organometallic compounds.

The organometallic compound in the organic layer may serve as a dopant.

According to another aspect, there is provided a diagnostic composition comprising at least one organometallic compound represented by the above formula (1).

The organic metal compound has excellent electrical characteristics and thermal stability. The organic light emitting device employing the organic metal compound has excellent driving voltage, efficiency, power, color purity and lifetime characteristics. In addition, since the organometallic compound has excellent phosphorescent emission characteristics, it can provide a diagnostic composition having a high diagnostic efficiency.

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 >

In Formula 1, M may be palladium (Pd), platinum (Pt), or gold (Au). For example, the M may be platinum, but is not limited thereto.

The organometallic compound represented by the general formula (1) may be neutral not composed of an ion pair of a cation and an anion.

In Formula 1, X ₁ is O or S, and the bond between M and X ₁ may be a covalent bond.

X ₂ in Formula 1 is N, X ₃ and X ₄ are independently of each other C or N, a bond between M and X ₂ , a bond between M and X _3, and a bond between M and X ₄ The dog may be a coordination bond, and the remaining one may be a covalent bond.

Y ₁ to Y ₇ in Formula 1 are independently of each other C or N, and Y ₈ and Y ₉ are independently of each other C, N, O, or S.

According to one embodiment, X ₁ in the formula 1 is O, X ₂ and X ₄ are N, X ₃ is C, the bond between X ₂ and M and the bond between X ₄ and M is a coordinate bond , The bond between X ₃ and M is a covalent bond, and Y ₁ to Y ₇ may be C, but is not limited thereto.

The bond or atomic group between Y ₁ and Y ₈ and the bond or atomic group between Y ₁ and Y _{2 in} the formula 1 constitute CY ₁ and the bond or atomic group between X ₂ and Y ₃ and the bond between X ₂ and Y ₄ A bond or an atomic group constitutes CY ₂ , a bond or an atomic group between X ₃ and Y ₅ and a bond or an atomic group between X ₃ and Y ₆ constitute CY ₃ , a bond or atomic group between X ₄ and Y ₇ and X The bond or atomic group between ₄ and Y ₉ may constitute CY ₄ .

In the formula (1), CY ₁ to CY ₄ may be independently selected from a C ₅ -C ₃₀ carbocyclic group and a C ₁ -C ₃₀ heterocyclic group.

For example, CY ₁ to CY ₄ in the above formula (1) independently represent a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, , 2,3,4-tetrahydronaphthalene group, pyrrole group, thiophene group, furan group, indole group, benzo borole group, benzofospor group, indene group, Group, a benzothiophene group, a benzothienophene group, a benzofuran group, a carbazole group, a dibenzo borole group, a dibenzo phosphole group, a fluorene group, a dibenzoyl group, Benzothiophene group, dibenzothelenophene group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azacavazole group , Azadibenzo boro group, azadibenzo phosphole group, az Aza dibenzothiophene 5-oxide group, aza-9H group, azabenzothiophene group, azabenzothiophene-5-oxide group, azabenzothiophene group, A pyridazine group, a pyridazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinoline group, An oxazole group, an isothiazole group, an oxadiazole group, an oxadiazole group, a thiadiazole group, a thiadiazole group, an imidazole group, a thiazole group, A benzoimidazole group, a benzooxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline (5, 6,7,8-tetrahydroisoquinoline) group and 5,6,7,8-te La may be selected from dihydroquinoline (5,6,7,8-tetrahydroquinoline).

According to another embodiment, CY ₁ to CY ₄ in Formula 1 may be independently selected from 6-membered rings.

According to another embodiment, CY ₁ and CY ₃ in the above formula (1) independently of one another are a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group A carbazole group, a fluorene group, a dibenzoylsilyl group, a dibenzothiophene group, a dibenzofuran group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, CY ₂ and CY ₄ are independently selected from the group consisting of a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group and a quinoxaline group; Quinazoline group, but is not limited thereto.

According to another embodiment, CY ₁ and CY ₃ in the formula (1) may be the same, and CY ₂ and CY ₄ may be the same. However, the present invention is not limited thereto.

In the present specification, the terms "azacibazole group, azadibenzo borole group, azadibenzofospor group, azafluorene group, azadibenzosilyl group, azadibenzotomole group, azadibenzothiophene group, azadibenzosele Azaindibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group and azadibenzothiophene 5,5-dioxide group "are each referred to as" carbazole group , A dibenzoylborane group, a dibenzofurane group, a dibenzofurane group, a dibenzothiophene group, a dibenzothiophene group, a dibenzothiophene group, a dibenzothiophene group, a dibenzothiophene group, Group, " 9H-fluorene-9-one group and dibenzothiophene 5,5-dioxide group " means a heterocycle having at least one of the carbons forming the ring thereof substituted with nitrogen do.

In the formula _1, T 1 is _{* -N [(L 61) a61} - (R 61)] - * ', * -B (R 61) - *', * -P (R 61) - * ', * _{-C (R 61) (R 62} ) - * ', * -Si (R 61) (R 62) - *', * -Ge (R 61) (R 62) - * ', * -S- *' , * -Se- * ', * -O- *', * -C (= O) - * ', * -S (= O) - *', * -S (= O) 2 - * ', * _{-C (R 61) = * '} , * = C (R 61) - *', * -C (R 61) = C (R 62) - * ', * -C (= S) - *' - and -C≡C- * 'is selected from, T ₂ is _{* -N [(L 63) a63} - (R 63)] - *', * -B (R 63) - * ', * -P (R 63 ) - * ', * -C ( R 63) (R 64) - *', * -Si (R 63) (R 64) - * ', * -Ge (R 63) (R 64) - *', -S (= O) -, -S (= O) -, -S (= O) _{2 - * ', * -C (} R 63) = *', * = C (R 63) - * ', * -C (R 63) = C (R 64) - *', * -C (= S ) - * '- and -C≡C- *' is selected from, T ₃ is _{* -N [(L 65) a65} - (R 65)] - * ', * -B (R 65) - *', _{* -P (R 65) - *} ', * -C (R 65) (R 66) - *', * -Si (R 65) (R 66) - * ', * -Ge (R 65) (R _{66) - * ', * -S-} *', * -Se- * ', * -O- *', * -C (= O) - * ', * -S (= O) - *', * _{-S (= O) 2 - *} ', * -C (R 65) = *', * = C (R 65) - * ', * -C (R 65) = C (R 66) - *', * -C (= S) - * 'and * -C≡C- *'. The description of R ₆₁ to R ₆₆ will be described later.

L ₆₁ , L ₆₃ and L ₆₅ are each independently selected from a single bond, a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group, a61, a63 and a65 are independently selected from 1 to 3 from each other is (for example, a61, a63 and a65 are may 1 il), a61 is the case 2 or more, two or more of L ₆₁ may be the same or different, and a63 each other Two or more L < ₆₃ > s are the same as or different from each other, and when a > ₆₅ is 2 or more, L < ₆₅ >

According to one embodiment, L ₆₁ , L ₆₃ and L ₆₅ are, independently of each other,

A single bond, a phenylene group, a naphthylene group, a fluorenylene group, a pyridinylene group, a pyrimidinylene group and a carbazolylene group; And

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, An amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid 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 phenylene group, a naphthylene group, a fluorenylene group, a pyridinylene group, a pyrimidinylene group and a carbazolylene group which are substituted with at least one selected from a biphenyl group and a terphenyl group;

, But is not limited thereto.

R ₆₁ and R ₆₂ , R ₆₃ and R ₆₄ and R ₆₅ and R ₆₆ are each optionally bonded to one another via a first linking group (to be described later) to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group (for example, a 5-membered to 7-membered cyclic group of 5 or 6 carbon atoms, A 5- to 7-membered cyclic group of 5 or 6 carbon atoms substituted with at least one of a C ₁ -C ₁₀ alkyl group and a C ₆ -C ₁₄ aryl group).

According to one embodiment, in Formula 1 T ₁ is _{* -N [(L 61) a61} - (R 61)] - * ', * -B (R 61) - *', * -P (R 61) - * ', * -C (R 61) (R 62) - *', * -Si (R 61) (R 62) - * ', * -S- *' and * -O- * 'or selected from , T ₂ is _{* -N [(L 63) a63} - (R 63)] - * ', * -B (R 63) - *', * -P (R 63) - * ', * -C (R ₆₃ ) (R ₆₄ ) - *, -Si (R ₆₃ ) (R ₆₄ ) - *, * -S- * and * -O- *, or T ₃ is * -N [ _{L 65) a65 - (R 65} )] - * ', * -B (R 65) - *', * -P (R 65) - * ', * -C (R 65) (R 66) - *' , * -Si (R ₆₅ ) (R ₆₆ ) - * ', * -S- *' and * -O- * '.

According to another embodiment, T _1, of the formula (1) is _{* -C (R 61) (R} 62) - * ', * -Si (R 61) (R 62) - *' and * -Ge (R ₆₁₎ (R ₆₂₎ - * 'selected from or, T ₂ is _{* -C (R 63) (R} 64) - *', * -Si (R 63) (R 64) - * ' and * -Ge (R ₆₃ ) (R ₆₄₎ - * 'or selected from, T ₃ is _{* -C (R 65) (R} 66) - *', * -Si (R 65) (R 66) - * ' and * -Ge (R ₆₅ ) (R ₆₆ ) - *, wherein R ₆₁ and R ₆₂ , R ₆₃ and R ₆₄ and / or R ₆₅ and R ₆₆ are connected to each other through a first linking group,

The first connector is a single _{bond, * -N [(L 9)} a9 - (R 9)] - * ', * -B (R 9) - *', * -P (R 9) - * ', _{* -C (R 9) (R} 10) - * ', * -Si (R 9) (R 10) - *', * -Ge (R 9) (R 10) - * ', * -S- * ', * -Se- *', * -O- * ', * -C (= O) - *', * -S (= O) - * ', * -S (= O) 2 - *', * -C (R ₉ ) = C (R ₁₀ ) - *, -C (= S) - * and * -C≡C- *

The description of L ₉ and a ₉ above will be referred to the description of L ₆₁ and a _{61 in the} present specification,

A description of the R ₉ and R _10, refer to the description of R ₆₁ in each of the specification, and

* And * may be, independently of each other, a bonding site with neighboring atoms, but are not limited thereto.

B1 to b3 in the above formula (1) represent the number of T ₁ to T ₃ , independently of each other, 0, 1, 2 or 3, and when b 1 is 0, * - (T ₁ ) _{b 1} - * ' is a bond, when b2 is 0, _{* - (T 2) b2 -} ' case is a single bond, b3 is 0, _{* - (T 3) b3 -} *' * may be a single bond. When b1 is 2 or more, 2 or more T _{1 s} are the same or different, and when b ₂ is 2 or more, 2 or more T _{2 s} are the same or different and when b ₃ is 2 or more, 2 or more T _{3 s} may be the same or different.

According to one embodiment, b1 to b3 in the above formula (1) independently of one another are 0 or 1, and b1 + b2 + b3 may be 0, 1 or 2.

According to another embodiment,

b1 = 0, b2 = 0 and b3 = 0;

b1 = 1, b2 = 0 and b3 = 0;

b1 = 0, b2 = 1 and b3 = 0;

b1 = 0, b2 = 0 and b3 = 1;

b1 = 1, b2 = 1 and b3 = 0; or

b1 = 1, b2 = 0 and b3 = 1;

b1 = 0, b2 = 1 and b3 = 1, but is not limited thereto.

Z ₁ to Z ₄ in the formula 1 may be independently selected from the group consisting of a group represented by the following formula (2A), a group represented by the following formula (2B), a group represented by the following formula (2C) :

In the above formulas (2A) to (2D), R ₅₁ to R ₅₃ are described below, and * is a bonding site with neighboring atoms.

For example, Z ₁ to Z ₄ in Formula 1 may be independently selected from the group consisting of Formula (2A) and Formula (2D), but is not limited thereto.

As showing a number of the above formula 1 c1 to c4 are Z ₁ to Z ₄ each, independently of one another, doedoe selected from an integer from 0 to 5, is more than the sum of c1 to c4 are 1. That is, the above-mentioned formula (1) includes at least one of Z ₁ to Z ₄ as a substituent. When c1 is 2 or more, 2 or more Z _{1 s} are the same or different and when c ₂ is 2 or more, 2 or more Z ₂ are the same or different and when c ₃ is 2 or more, 2 or more Z ₃ are the same or different from each other , And when c4 is 2 or more, 2 or more of Z ₄ may be the same or different from each other.

According to one embodiment, c1 + c2 + c3 + c4 in the above formula (1) may be 1, 2 or 3.

According to another embodiment, c4 in the above formula (1) may be 0.

According to another embodiment, c1 + c2 + c3 in the general formula (1) may be 1, 2 or 3 and c4 may be 0.

According to another embodiment, in Formula 1,

c1 = 1, c2 = 0, c3 = 0 and c4 = 0;

c1 = 0, c2 = 1, c3 = 0 and c4 = 0;

c1 = 0, c2 = 0, c3 = 1 and c4 = 0;

c1 = 0, c2 = 0, c3 = 0 and c4 = 1; or

c1 = 0, c2 = 2, c3 = 0 and c4 = 0, but is not limited thereto.

R ₁ to R ₄ , R ₅₁ to R ₅₃ and R ₆₁ to R ₆₆ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , a hydroxyl group, a nitro group, an amidino group, a hydrazine group, a hydrazone jongi, a carboxylic acid group or a salt thereof, a sulfonic acid group or the ring a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ 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 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 group, Chi Or unsubstituted monovalent non-ring - is an aromatic condensed polycyclic group, a substituted or unsubstituted 1, a non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 1) (Q} 2), -Si (Q 3) (Q 4) ( _{Q 5), -B (Q 6} ) (Q 7) , and _{-P (= O) (Q 8} ) (Q 9) doedoe selected from the of the formula (2A) R ₅₁ and R ₅₂ (or formula 2A to 2D of R ₅₁ to R ₅₃₎ are independently of one another, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl alkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted ring unsubstituted 1 may be selected from non-aromatic condensed polycyclic groups and substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic groups. Here, the descriptions of Q ₁ to Q ₉ are referred to in this specification.

For example, Q ₁ to Q ₉ may be, 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 one embodiment, R ₁ to R ₄ , R ₅₁ to R ₅₃ and R ₆₁ to R ₆₆ independently of one another are hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , A substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted or unsubstituted Substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic , Wherein R ₅₁ and R ₅₂ (or R ₅₁ to R ₅₃ in the formulas (2A) to (2D)) in Formula (2A) are independently selected from substituted or unsubstituted 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 heterocycloalkene A substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent Non-aromatic heterocyclic polycyclic groups.

For example, R ₁ to R ₄ , R ₅₁ to R ₅₃ and R ₆₁ to R ₆₆ independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group and C ₁ -C ₂₀ alkyl 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, 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, An adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo [2.2.2] octyl group, a phenyl group, a naphthyl group A C ₁ -C ₂₀ alkyl group substituted with at least one of a methyl group, an ethyl group, a t-butyl group, a pyridinyl group, and a pyrimidinyl group;

A cyclopentyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, Anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, klychenyl group, pyrrolyl group, thiophenyl group, thiophenyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, a pyrazolyl group, A benzoimidazolyl group, a benzoimidazolyl group, a benzoimidazolyl group, a benzoimidazolyl group, a benzoimidazolyl group, a benzoimidazolyl group, an imidazolyl group, an indolyl group, an indolyl group, A furanyl group, a benzothiophenyl group, an isobenzothiazolyl group , A benzooxazolyl 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 imidazolopyrimidinyl group; And

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, 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 cyclohexyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptyl group, a cycloheptyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, 2] octyl 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, a klychenyl group, a pyrrolyl group, a thiophenyl group, A thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrimidinyl group, A heterocyclic group, a phenanthroline group, a phenanthroline group, an imidazolyl group, an indolyl group, an indolyl group, an indazolyl group, a fluorenyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, A thiazolyl group, an oxadiazolyl group, a triazinyl group, a diazonaphthyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, A cyclohexyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, a cyclopentyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, A cyclohexyl group, a cycloheptenyl group, a bicyclo [2.2.2] octyl group, a phenyl group, a cyclohexyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, Naphthyl group, fluoro A pyranyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, an isothiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, A thiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, A benzoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, , Isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl And an imidazopyrimidinyl group;

, Wherein R ₅₁ and R ₅₂ (or R ₅₁ to R ₅₃ in the above formulas (2A) to (2D)) of the formula (2A)

A cyclopentyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, Anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, klychenyl group, pyrrolyl group, thiophenyl group, thiophenyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, a pyrazolyl group, A benzoimidazolyl group, a benzoimidazolyl group, a benzoimidazolyl group, a benzoimidazolyl group, a benzoimidazolyl group, a benzoimidazolyl group, an imidazolyl group, an indolyl group, an indolyl group, A furanyl group, a benzothiophenyl group, an isobenzothiazolyl group , A benzooxazolyl 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 imidazolopyrimidinyl group; And

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, 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 cyclohexyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptyl group, a cycloheptyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, 2] octyl 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, a klychenyl group, a pyrrolyl group, a thiophenyl group, A thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrimidinyl group, A heterocyclic group, a phenanthroline group, a phenanthroline group, an imidazolyl group, an indolyl group, an indolyl group, an indazolyl group, a fluorenyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, A thiazolyl group, an oxadiazolyl group, a triazinyl group, a diazonaphthyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, A cyclohexyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, a cyclopentyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, A cyclohexyl group, a cycloheptenyl group, a bicyclo [2.2.2] octyl group, a phenyl group, a cyclohexyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, Naphthyl group, fluoro A pyranyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, an isothiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, A thiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, A benzoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, , Isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl And an imidazopyrimidinyl group;

, But is not limited thereto.

According to one embodiment, R ₁ to R ₄ , R ₅₁ to R ₅₃ and R ₆₁ to R ₆₆ 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 norbornanyl group, a cyclopentyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclohexyl group, A cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo [2.2.2] octyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; And

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 cyclopentenyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a cyclopentyl group, a cycloheptyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, A methyl group, an ethyl group, an n-butyl group, a naphthyl group, a naphthyl group, a naphthyl group, a bicyclo [2.2.2] octyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group Propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, Heptyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, An n-nonyl group, an isononyl group, a sec- A cyclopentyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a nor-naphthyl group, a cyclopentyl group, a cyclopentyl group, A norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo [2.2.2] octyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, A divalent group, a dibenzofuranyl group and a dibenzothiophenyl group;

, Wherein R ₅₁ and R ₅₂ (or R ₅₁ to R ₅₃ in the formulas (2A) to (2D)) of the formula (2A)

A cyclopentyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, A bicyclo [2.2.2] octyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; And

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 cyclopentenyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a cyclopentyl group, a cycloheptyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, A cyclopentyl group substituted with at least one member selected from the group consisting of a phenyl group, a cyclohexyl group, a bicyclo [2.2.2] octyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group A cyclohexyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptyl group, a cycloheptyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, 2] octyl group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophene group Nil group;

≪ / RTI >

According to another embodiment, R ₁ to R ₄ , R ₅₁ to R ₅₃ and R ₆₁ to R ₆₆ 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 , groups represented by the following formulas 9-1 to 9-20 and the following formulas 10-1 to 10-142 Wherein R ₅₁ and R ₅₂ (or R ₅₁ to R ₅₃ in the formulas (2A) to (2D)) of the formula (2A) are independently selected from the group consisting of the following formulas (10-1) to (10-4) -10 and 10-13 to 10-141: < RTI ID = 0.0 >

In Formulas 9-1 to 9-20 and 10-1 to 10-142, * denotes a binding site with neighboring atoms, Ph denotes a phenyl group, and TMS denotes a trimethylsilyl group.

A1 to a4 in the formula (1) represent the number of R ₁ to R ₄ , and may be independently 0, 1, 2, 3, 4 or 5. The a1 is 2, if greater, may be two or more of R ₁ are the same or different from each other, if the a2 is 2 or greater, it is possible to two or more of R ₂ are the same or different from each other, when the a3 is 2 or more, two or more of R ₃ may be the same as or different from each other, and when a4 is at least 2, at least two R ₄ may be the same or different, but are not limited thereto.

In Formula 1, two of the three a1 R ₁ is optionally, in combination with each other, a substituted or unsubstituted C ₅ -C ₃₀ carbonyl when the cyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group, may form, two of a2 of R ₂ is optionally, in combination with each other, a substituted or unsubstituted C ₅ -C ₃₀ carbonyl when the cyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group, may form, two of a3 of R ₃ is optionally, in combination with each other, a substituted or unsubstituted C ₅ -C ₃₀ carbonyl when the cyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group, may form, two of a4 of R ₄ is optionally, in combination with each other, a substituted or unsubstituted C ₅ -C ₃₀ carbonyl when the cyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group, It may form, R ₁ to R ₄ of the neighboring two or more optionally, in combination with each other, substituted or unsubstituted C ₅ -C ₃₀ when carbonyl may form a cyclic group, or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group, R 2 out of ₅₁ to R ₅₃ are optionally, in combination with each other, substituted or unsubstituted a C ₅ -C ₃₀ carbonyl when it is possible to form a cyclic group, or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group.

For example, the general formula (2) of i) a1 of R ₁ of 1, ii) two of a2 of R _2, iii) two of a3 of R _3, two of iv) a4 of R ₄ dogs, v) R ₁ to R ₄ of the above adjacent second and vi) two out of R ₅₁ to R ₅₃ are respectively bonded to each other, which can form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group, or a substituted or The unsubstituted C ₁ -C ₃₀ heterocyclic group may be,

A cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, a cyclopentadiene group, , Naphthalene group, anthracene group, tetracene group, phenanthrene group, dihydronaphthalene group, phenalene group, benzothiophene group, benzofuran group, indene group, indole group, benzoylol group, azabenzothiophene group, A benzofuran group, an azindene group, an azaindole group, and an azabenzoyl group;

A cyclohexane group, a cycloheptane group, an adamantane group, a bicycle-heptane group, a bicyclo-octane group, a benzene group, a pyridine group, a pyridine group substituted with at least one R _1a , A benzene ring, a benzene ring, a benzene ring, a benzene ring, a benzene ring, a benzene ring, an imine group, a pyrazine group, a pyridazine group, a naphthalene group, an anthracene group, a tetracene group, a phenanthrene group, a dihydronaphthalene group, Group, an azabenzothiophene group, an azabenzofuran group, an azindene group, an azaindole group, and an azabenzoyl group;

, But is not limited thereto.

For example, R ₅₁ and R ₅₂ in Formula 2A may optionally be bonded to each other through a single bond, and Formula (2A) may have a carbazole ring backbone.

For a description of R _1a , refer to the description of R ₁ in the present specification.

로 표시되는 모이어티는 하기 화학식 CY1-1 내지 CY1-26로 표시되는 그룹 중에서 선택될 수 있다:For example,

May be selected from the group represented by the following formulas CY1-1 to CY1-26:

Among the above-mentioned formulas CY1-1 to CY1-26

X ₁₉ is C (R ₁₈ ) (R ₁₉ ), N (R ₁₈ ), O, S or Si (R ₁₈ ) (R ₁₉ )

The description of Y ₁ , Z ₁ and R ₁ , respectively, as set forth herein,

R ₁₁ to R ₁₉ each refer to the description of R ₁ in the present specification,

d1 and e1 are independently selected from integers of from 0 to 2,

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

로 표시되는 모이어티는 하기 화학식 CY2-1 내지 CY2-8로 표시되는 그룹 중에서 선택될 수 있다:As another example,

May be selected from the group represented by the following formulas CY2-1 to CY2-8:

Among the above-mentioned formulas CY2-1 to CY2-8

X ₂ , Z ₂ and R ₂ are each as described herein,

d2 and e2 are each independently selected from an integer of 0 to 2,

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

로 표시되는 모이어티는 하기 화학식 CY3-1 내지 CY3-12로 표시되는 그룹 중에서 선택될 수 있다:As another example,

May be selected from the group represented by the following formulas CY3-1 to CY3-12:

Among the above-mentioned formulas CY3-1 to CY3-12

And X ₃₉ are _{C (R 38) (R 39} ), N (R 38), O, S , or _{Si (R 38) (R 39} ),

X ₃ , Z ₃ and R ₃ are each as described herein,

R ₃₈ and R ₃₉ each refer to the description of R ₃ in this specification,

d3 and e3 are each independently selected from an integer of 0 to 2,

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

로 표시되는 모이어티는 하기 화학식 CY4-1 내지 CY4-26으로 표시되는 그룹 중에서 선택될 수 있다:As another example,

May be selected from the group represented by the following formulas CY4-1 to CY4-26:

Among the above-mentioned formulas CY4-1 to CY4-26

X ₄₉ is C (R ₄₈ ) (R ₄₉ ), N (R ₄₈ ), O, S or Si (R ₄₈ ) (R ₄₉ )

X ₄ , Z ₄ and R ₄ are each as described herein,

R ₄₁ to R ₄₉ each refer to the description of R ₄ in the present specification,

d4 and e4 are each independently selected from an integer of 0 to 2,

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

According to one embodiment,

로 표시되는 모이어티는 상기 화학식 CY1-1 내지 CY1-26로 표시되는 그룹 중에서 선택되고,

Is selected from the group represented by the above formulas CY1-1 to CY1-26,

로 표시되는 모이어티는 상기 화학식 CY2-1 내지 CY2-8로 표시되는 그룹 중에서 선택되고,

Is selected from the group represented by the above formulas CY2-1 to CY2-8,

로 표시되는 모이어티는 상기 화학식 CY3-1 내지 CY3-12로 표시되는 그룹 중에서 선택되고,

Is selected from the group represented by the above formulas CY3-1 to CY3-12,

로 표시되는 모이어티는 상기 화학식 CY4-1 내지 CY4-26으로 표시되는 그룹 중에서 선택되되, i) e1 + e2 + e3 + e4는 1 이상(예를 들면, 1, 2 또는 3)이거나, ii) e2는 1 또는 2이거나, iii) e1 + e2 + e3는 1 이상(예를 들면, 1, 2 또는 3)이고 e4는 0이거나, 또는 iv) e1, e3 및 e4는 0이고, e2는 1 또는 2일 수 있다.

(I) e1 + e2 + e3 + e4 is at least 1 (e.g., 1, 2 or 3), or ii) the moiety represented by the formula e2 is 1 or 2, or iii) e1 + e2 + e3 is 1 or more (e.g., 1, 2 or 3) and e4 is 0, or iv) e1, e3 and e4 are 0, e2 is 1 or 2 < / RTI >

로 표시되는 모이어티는 하기 화학식 CY2(1) 내지 CY2(18)로 표시되는 그룹 중에서 선택될 수 있다:According to another embodiment,

May be selected from the group represented by the following formulas CY2 (1) to CY2 (18)

Among the above-mentioned formulas CY2 (1) to CY2 (18)

X ₂ and Z ₂ are each as described herein, and the description of Z _2a and Z _2b respectively refer to the description of Z ₂ in this specification,

Description of the R ₂ are, but see what described in the present specification and description of R _2a and R _2b, see the description of the R ₂ of each of the present specification, R _2, R _2a and R _2b are not hydrogen,

*, * 'And *' are binding sites with neighboring atoms, respectively.

According to one embodiment, the organometallic compound may be represented by the following formula 1-1:

≪ Formula 1-1 >

The description of M, X ₁ , X ₂ , Y ₃ , Y ₄ , CY ₂ , T ₁ to T ₃ , b ₁ to b ₃ , Z ₁ to Z ₄ c2, R ₁ to R ₄ and a2 in the formula D1, d3, d4, e1, e3 and e4 are each independently selected from the integers from 0 to 2, and e1 + c2 + e3 + e4 can be 1, 2 or 3, .

For example, i) e1 + c2 + e3 + e4 in Formula 1-1 is at least 1 (e.g., 1, 2 or 3), or ii) c2 is 1 or 2, or iii) e3 may be 1 or more (e.g., 1, 2 or 3) and e4 may be 0, or iv) e1, e3 and e4 may be 0 and c2 may be 1 or 2.

로 표시되는 모이어티는 상기 화학식 CY2-1 내지 CY2-8로 표시되는 그룹 중에서 선택되고, 상기 화학식 1-1 중 i) e1 + e2 + e3 + e4는 1 이상(예를 들면, 1, 2 또는 3)이거나, ii) e2는 1 또는 2이거나, iii) e1 + e2 + e3는 1 이상(예를 들면, 1, 2 또는 3)이고 e4는 0이거나, 또는 iv) e1, e3 및 e4는 0이고, e2는 1 또는 2일 수 있으나, 이에 한정되는 것은 아니다. 또 다른 예로서, 상기 화학식 1-1 중As another example,

(I) e1 + e2 + e3 + e4 in the formula (1-1) is at least 1 (for example, 1, 2 or 3) 3) or ii) e2 is 1 or 2, or iii) e1 + e2 + e3 is at least 1 (e.g., 1, 2 or 3) and e4 is 0 or iv) e1, e3 and e4 are 0 And e2 may be 1 or 2, but is not limited thereto. As another example,

로 표시되는 모이어티는 상기 화학식 CY2(1) 내지 CY2(18)로 표시되는 그룹 중에서 선택되고,

Is selected from the group consisting of the above-mentioned formulas CY2 (1) to CY2 (18)

T ₁ is _{* -N [(L 61) a61} - (R 61)] - * ', * -B (R 61) - *', * -P (R 61) - * ', * -C (R 61 ) (R ₆₂₎ - is selected from, * -S- * 'and * -O- *', - * ' *, * -Si (R 61) (R 62)'

T ₂ is _{* -N [(L 63) a63} - (R 63)] - * ', * -B (R 63) - *', * -P (R 63) - * ', * -C (R 63 * -S- (R ₆₃ ) - (R ₆₄ ) -, -Si (R ₆₃ ) (R ₆₄ )

T ₃ is _{* -N [(L 65) a65} - (R 65)] - * ', * -B (R 65) - *', * -P (R 65) - * ', * -C (R 65 (R ₆₆ ) -, -Si (R ₆₅ ) (R ₆₆ ) -, -S- * and -O- *

b1 = 0, b2 = 0 and b3 = 0;

b1 = 1, b2 = 0 and b3 = 0;

b1 = 0, b2 = 1 and b3 = 0;

b1 = 0, b2 = 0 and b3 = 1;

b1 = 1, b2 = 1 and b3 = 0; or

b1 = 1, b2 = 0 and b3 = 1;

b1 = 0, b2 = 1 and b3 = 1, but is not limited thereto.

For example, the organometallic compound may be one of the following compounds 1 to 24, but is not limited thereto:

Wherein X ₁ is O or S, the bond between M and X ₁ is a covalent bond, X ₂ is N, X ₃ and X ₄ are independently of each other C or N, and between M and X ₂ The bond between M and X ₃ and the bond between M and X ₄ are coordinate bond and the remaining one is a covalent bond. As a result, the electron-donating ability of the organometallic compound increases due to the strong electron-donating ability of X ₁ , and the efficiency of the electronic device, for example, an organic light-emitting device employing the organometallic compound can be increased.

Z ₁ to Z ₄ in the general formula (1) are independently selected from the group represented by the formula (2A), the group represented by the formula (2B), the group represented by the formula (2C), and the group represented by the formula , and c1 to c4 are independently selected from integers of 0 to 5, and the sum of c1 to c4 is 1 or more. Groups represented by the group, and the formula 2D represented by the group, the formula 2C represented by the group, the formula 2B is represented by the formula (2A) are electron-donating group (electron donating group), provided in formula (2A) R _51, and R ₅₂ each independently represent 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, Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensation A polycyclic group, and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group, the formula (1) necessarily includes at least one electron donor group that is chemically and electrically stable. As a result, the HOMO energy level of the organic metal compound can be increased and the hole transporting ability of the organic metal compound can be improved, so that the efficiency of the electronic device using the organic metal compound, for example, have.

For example, the HOMO, LUMO, singlet (S ₁ ) and triplet (T ₁ ) energy levels for the compounds 1, 2, 14-19 and 21-24 are determined using the DFT method of the Gaussian program (B3LYP, The structure is optimized at the level of 6-31G (d, p). The evaluation results are shown in Table 1 below.

Compound No. HOMO (eV) LUMO (eV) S ₁ Energy level (eV) T ₁ energy level (eV) One -4.520 -1.307 2.618 2.407 2 -4.510 -1.306 2.610 2.404 14 -4.610 -1.375 2.623 2.428 15 -4.665 -1.503 2.551 2.712 16 -4.476 -1.247 3.229 2.435 17 -4.472 -1.336 2.587 2.392 18 -4.542 -1,620 2.612 2.406 19 -4.724 -1.306 2.610 2.404 21 -4.459 -1.562 2.344 2.190 22 -4.605 -1.506 2.531 2.389 23 -4.419 -1.013 2.814 2.674 24 -4.749 -1.358 2.818 2.647

It can be seen from the above Table 1 that the organometallic compound represented by Formula 1 has electrical characteristics suitable for use as an electron device, for example, as a dopant of an organic light emitting device.

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 can have a low driving voltage, a high efficiency, a high power, an elevator efficiency, a long lifetime, a low roll-off ratio, and excellent color purity by providing an organic layer containing an organometallic compound represented by the general formula .

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).

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 of the organic light emitting device may be an anode, the second electrode may be a cathode, and the organic layer may include a hole transporting region interposed between the first electrode and the light emitting layer, Wherein the hole transporting region comprises a hole injecting layer, a hole transporting layer, an electron blocking layer, or any combination thereof, wherein the electron transporting region comprises a hole blocking layer, an electron transporting layer, An electron injection layer, or any combination thereof.

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 a hole injecting layer, a hole transporting layer, an electron blocking layer, a buffer layer, or any combination thereof.

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

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group , C ₁ -C ₁₀ heterocycloalkyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ hetero aryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is non-inde aromatic heterocyclic condensed polycyclic group with at least one substituted phenyl group, a penta-alkylenyl group wherein carbonyl group, a naphthyl group, an azulenyl group, a heptal A phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a cyano group, a phenanthrene group, Carbonyl alkylenyl group, a hexenyl group naphtha, blood hexenyl group, a perylenyl group and a carbonyl penta hexenyl groups;

≪ / RTI >

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

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

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

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

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

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group substituted with at least one of a salt thereof, a C ₁ -C ₁₀ alkyl group, and a C ₁ -C ₁₀ alkoxy group;

, But is not limited thereto.

In the above formula (201), R < ₁₀₉ &

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

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

≪ / RTI >

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

≪ Formula 201A >

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

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

The thickness of the hole transporting region may be from about 100 A to about 10,000 A, for example, from about 100 A to about 1000 A. When the hole transporting region includes at least one of a hole injection layer and a hole transporting layer, the thickness of the hole injection 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 To about 2000 Angstroms, for example from about 100 Angstroms to about 1500 Angstroms. 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.

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,

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

≪ Formula 301 >

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

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

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

≪ / RTI >

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

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

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

≪ / RTI >

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

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

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

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

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group A phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group and a fluorenyl group which are substituted with at least one of a fluorenyl group and a fluorenyl group; And

;

;

, But is not limited thereto.

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

≪ 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 transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

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, e.g., 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.

According to another aspect, there is provided a diagnostic composition comprising at least one organometallic compound represented by the above formula (1).

Since the organometallic compound represented by Formula 1 can provide high luminous efficiency, the diagnostic composition containing the organometallic compound can have a high diagnostic efficiency.

The diagnostic composition can be applied to a variety of diagnostic kits, diagnostic reagents, biosensors, biomarkers, and the like.

In the present specification, the C ₁ -C ₆₀ alkyl group means a linear or branched saturated 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 tert-butyl group, a pentyl group, an iso-amyl group, a hexyl group, and the like. In the present specification, a C ₁ -C ₆₀ alkylene group means a divalent group having the same structure as the above C ₁ -C ₆₀ alkyl group.

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

In the present specification, the C ₂ -C ₆₀ alkenyl group has a structure containing at least one carbon-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, a butenyl group, . 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 at least one carbon-carbon triple bond at the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include ethynyl, propynyl 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 heteroatom selected from N, O, P, Si and S as a ring-forming atom, Specific examples thereof include a tetrahydrofuranyl group, a tetrahydrothiophenyl group, 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 means a monovalent monocyclic group having 3 to 10 carbon atoms, which has at least one carbon-carbon double bond in the ring, but does not have aromaticity , And specific examples thereof 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, a 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, Si and S as a ring-forming atom, Lt; RTI ID = 0.0 > a < / RTI > Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl group include a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and the like. In the present specification, the C ₁ -C ₁₀ heterocycloalkenylene group means a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkenyl group.

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

In the present specification, the C ₁ -C ₆₀ heteroaryl group is a monovalent group having at least one hetero atom selected from N, O, P, Si and S as a ring-forming atom and having a cyclic aromatic system having 1 to 60 carbon atoms C ₁ -C ₆₀ heteroarylene group means a bivalent 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 it means. 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 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 a non-aromaticity. (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 condensed heteropolycyclic group in which two or more rings are condensed with each other and a hetero atom selected from N, O, P, Si and S (For example, having from 1 to 60 carbon atoms) having a non-aromaticity throughout the molecule. 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 C ₅ -C ₃₀ carbocyclic group refers to a saturated or unsaturated cyclic group having only 5 to 30 carbons as a ring forming atom. The C ₅ -C ₃₀ carbocyclic group may be a monocyclic group or a polycyclic group.

In the present specification, a C ₁ -C ₃₀ heterocyclic group refers to a saturated or unsaturated cyclic group having at least one heteroatom selected from N, O, P, Si and S in addition to 1 to 30 carbons as a ring forming atom. The C ₁ -C ₃₀ heterocyclic group may be a monocyclic group or a polycyclic group.

The substituted C ₅ -C ₃₀ carbocyclic group, the substituted C ₂ -C ₃₀ heterocyclic group, the substituted C ₁ -C ₆₀ alkyl group, the substituted C ₂ -C ₆₀ alkenyl group, the substituted C ₂ -C _A substituted C ₁ -C ₆ 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 cycloalkenyl group, a substituted C ₁ -C ₁₀ cycloalkenyl group, -C ₁₀ hetero 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, , The substituted monovalent non-aromatic condensed polycyclic group and the substituted 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, 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 );

≪ / 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 a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or its salt, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ 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 ₁ -C ₆₀ alkyl and C ₆ -C ₆₀ aryl group substituted by at least one of C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, 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.

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 2

Synthesis of Ligand 2

9.82 g (26.8 mmol) of (3 - ([1,1'-biphenyl] -2-yl (pyridi- 2-yl) amino) phenyl) boronic acid, 89 ml of toluene and 29 ml of ethanol were added to the reactor. Here, 2- (2- (oxy carry) phenyl) -6-chloro -N, N- diphenyl-pyridin-4-amine 10.0g (26.82mmol), Pd (PPh 3) 4 1.5g (1.34 mmol) and 40 ml of 2.0 M sodium carbonate solution was added and the mixture was heated to reflux at 110 캜 for 18 hours. When the reaction was completed, the mixture was concentrated under reduced pressure, dissolved in 400 ml of dichloromethane, filtered through diatomaceous earth. The organic layer thus obtained was dried over magnesium sulfate, distilled under reduced pressure, and purified by liquid chromatography to obtain 14.3 g (21.72 mmol, yield 81%) of ligand 2. LC / MS m / z = 659 (M + H) +

Synthesis of Compound 2

After 10 g (15.18 mmol) of the ligand 2 and 100 ml of benzonitrile were mixed, 7.17 g (15.18 mmol) of PtCl ₂ (NCPh) ₂ was added, and the mixture was refluxed for 4 hours. After completion of the reaction, the mixture was concentrated under reduced pressure and purified by liquid chromatography to obtain 9.05 g (10.6 mmol, yield 70%) of Compound 2. [ The resulting compound was confirmed by LC / MS and < ¹ > H NMR. LC-MS m / z = 852 (M + H) < ⁺ & gt ^;

¹ H NMR (300 mHz, CDCl ₃ )? 7.21 (d, IH), 7.80 (d, IH), 7.71 , 7.42 (m, 9H), 7.25 (m, 11H), 6.99 (d, IH), 6.82

Synthetic example  2: Synthesis of Compound 14

Synthesis of ligand 14

To the reactor was added 12.3 g (33.7 mmol) of (3 - ([1,1'-biphenyl] -2-yl (pyridi- 2-yl) amino) phenyl) boronic acid, 112 ml of toluene and 37 ml of ethanol. Here, the 2- (2- (oxy carry) phenyl) -6-chloro-4-phenoxy-pyridin 10.0g (33.7mmol), Pd (PPh 3) 4 1.95g (1.69 mmol) and 2.0M sodium carbonate solution, 50ml After the addition, the mixture was heated to reflux at 110 < 0 > C for 18 hours. When the reaction was completed, the mixture was concentrated under reduced pressure, dissolved in 400 ml of dichloromethane, filtered through diatomaceous earth. The organic layer thus obtained was dried over magnesium sulfate, distilled under reduced pressure, and purified by liquid chromatography to obtain 14.9 g (25.61 mmol, yield 76%) of the ligand 14. LC / MS < RTI ID = 0.0 > m / z = 584 (M ⁺

Synthesis of Compound 14

After 10 g (17.13 mmol) of the ligand 14 and 100 ml of benzonitrile were mixed, 8.09 g (17.13 mmol) of PtCl ₂ (NCPh) ₂ was added, and the mixture was refluxed for 4 hours. After completion of the reaction, the mixture was concentrated under reduced pressure and purified by liquid chromatography to obtain 9.05 g (11.65 mmol, yield 68%) of Compound 14. The resulting compound was confirmed by LC / MS and < ¹ > H NMR. LC-MS m / z = 777 (M + H) < ⁺ & gt ^;

¹ H NMR (300 mHz, CDCl ₃ ) 10.20 (d, IH), 7.79 (d, IH), 7.69 (t, IH), 7.63 (d, 2H), 7.59 , 7.37 (m, 7H), 7.18 (m, 7H), 6.87 (d, 2H), 6.79 (s,

Evaluation Example 1: Measurement of decay time

A quartz substrate cleaned with chloroform and pure water was prepared and then a predetermined material described in the following Table 2 was vacuum-deposited at a degree of vacuum of 10 ^-7 torr to deposit 50 nm thick films 1, 2, A, and B Prepared.

Film name Compound used in film production Film 1 CBP: Compound 2 (weight ratio of 9: 1) Film 2 CBP: Compound 14 (weight ratio of 9: 1) Film A CBP: Compound A (weight ratio of 9: 1) Film B CBP: Compound B (weight ratio of 9: 1)

Subsequently, FluoTime 300, a TRPL measurement system of PicoQuant, and PLS340 (excitation wavelength = 340 nm, spectral width = 20 nm), which is a pumping source of PicoQuant, were used for the films 1, 2, A and B prepared as described above The PL spectra were evaluated at room temperature and the wavelengths of the main peaks of the spectrum were determined to determine the main peak of each spectrum from the respective films by a photon pulse (pulse width = 500 picoseconds) The number of photons emitted from the wavelength was measured over time based on Time-Correlated Single Photon Counting (TCSPC), and a TRPL curve with sufficient fitting was obtained. Two or more exponential decay functions were fitted to the obtained results to obtain T _decay (Ex), i.e., decay time, of each of films 1, 2, A and B, and the results are shown in Table 3 . Function used in Fitting is the same as for <Equation 1>, and takes the largest value of T obtained from the respective _decay exponential decay function used in the fitting in T _decay (Ex). At this time, the same measurement is repeated in the dark state (the state where the pumping signal incident on the predetermined film is cut off) is repeated one more time during the measurement time same as the measurement time for obtaining the TRPL curve to obtain a baseline or background signal curve As a baseline.

&Lt; Formula 1 >

Film name Decay time
(㎲) Film 1 4.04 Film 2 4.82 Film A 5.76 Film B 5.23

From Table 3, it can be seen that Compounds 2 and 14 have shorter decay times than Compounds A and B.

Example  One

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.

Then, 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 2 (dopant) and CBP (host) were co-deposited on the hole transport 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) Alq ₃ / LiF (10 Å) / Al (1200 Å) structure was fabricated using the same method as described above.

Example 2 and Comparative Examples A and B

An organic light emitting device was fabricated in the same manner as in Example 1 except that the compound described in Table 4 was used instead of Compound 2 as a dopant in forming the light emitting layer.

Evaluation Example 2: Characteristic evaluation of organic light emitting device

The driving voltage, efficiency, maximum emission wavelength, quantum efficiency and lifetime (T ₉₅ ) were evaluated for each of the organic light emitting devices manufactured in Examples 1 and 2 and Comparative Examples A and B, and the results are shown in Table 4 . A current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as the evaluation device and the life time (T ₉₅ ) (at 6000 nit) .

Dopant Driving
Voltage
(V) efficiency
(cd / A) Maximum emission wavelength
(nm) quantum
efficiency
(%) life span
(hr)
(T ₉₅ ) Example 1 Compound 2 4.07 78.4 529 22.2 40 Example 2 Compound 14 4.15 72.0 532 19.9 25 Comparative Example A Compound A 4.16 71.1 531 19.6 20 Comparative Example B Compound B 4.17 64.3 545 18.7 15

It can be seen from Table 4 that the organic light emitting devices of Examples 1 and 2 have excellent driving voltage, efficiency, quantum efficiency and lifetime characteristics as compared with the organic light emitting devices of Comparative Examples A and B.

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

Claims (20)

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

In Formulas 1 and 2A to 2D,
M is palladium (Pd), platinum (Pt), or gold (Au)
X ₁ is O or S, the bond between M and X ₁ is a covalent bond,
X ₂ is N, X ₃ and X ₄ are independently of each other C or N,
The bond between M and X ₂ , the bond between M and X _3, and the bond between M and X ₄ are coordinate bond and the remaining one is a covalent bond,
Y ₁ to Y ₇ are independently of each other C or N,
Y ₈ and Y ₉ are independently of each other C, N, O or S,
A bond between Y ₁ and Y ₈ or an atomic group and a bond or an atomic group between Y ₁ and Y ₂ constitute CY ₁ and a bond or an atomic group between X ₂ and Y ₃ and a bond or an atomic group between X ₂ and Y ₄ CY ₂ , the bond between X ₃ and Y ₅ or the atomic group and the bond or atomic group between X ₃ and Y ₆ constitute CY ₃ , the bond or atomic group between X ₄ and Y _7, and the bond between X ₄ and Y ₉ Or the atomic group constitutes CY ₄ ,
CY ₁ to CY ₄ are independently selected from a C ₅ -C ₃₀ carbocyclic group and a C ₁ -C ₃₀ heterocyclic group,
T ₁ is _{* -N [(L 61) a61} - (R 61)] - * ', * -B (R 61) - *', * -P (R 61) - * ', * -C (R 61 _{) (R 62) - * '} , * -Si (R 61) (R 62) - *', * -Ge (R 61) (R 62) - * ', * -S- *', * -Se- * ', * -O- *', * -C (= O) - * ', * -S (= O) - *', * -S (= O) 2 - * ', * -C (R 61 ) = * ', * = C (R 61) - *', * -C (R 61) = C (R 62) - * ', * -C (= S) - *' and * -C≡C- * &Quot;,&quot;
T ₂ is _{* -N [(L 63) a63} - (R 63)] - * ', * -B (R 63) - *', * -P (R 63) - * ', * -C (R 63 _{) (R 64) - * '} , * -Si (R 63) (R 64) - *', * -Ge (R 63) (R 64) - * ', * -S- *', * -Se- * ', * -O- *', * -C (= O) - * ', * -S (= O) - *', * -S (= O) 2 - * ', * -C (R 63 ) = * ', * = C (R 63) - *', * -C (R 63) = C (R 64) - * ', * -C (= S) - *' and * -C≡C- * &Quot;,&quot;
T ₃ is _{* -N [(L 65) a65} - (R 65)] - * ', * -B (R 65) - *', * -P (R 65) - * ', * -C (R 65 _{) (R 66) - * '} , * -Si (R 65) (R 66) - *', * -Ge (R 65) (R 66) - * ', * -S- *', * -Se- * ', * -O- *', * -C (= O) - * ', * -S (= O) - *', * -S (= O) 2 - * ', * -C (R 65 ) = * ', * = C (R 65) - *', * -C (R 65) = C (R 66) - * ', * -C (= S) - *' and * -C≡C- * &Quot;,&quot;
L ₆₁ , L ₆₃ and L ₆₅ are each independently selected from a single bond, a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
a61, a63, and a65 is selected from 1 to 3, independently of one another, a61 this case, 2 or more, two or more of L ₆₁ are to each other the same or different, and a63 in this case 2 or more, two or more of L ₆₃ may be the same or different, and a65 each other Is 2 or more, two or more L &lt; ₆₅ &gt; s are the same or different from each other,
R ₆₁ and R ₆₂ are optionally linked to one another through a first linking group to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group Can,
R ₆₃ and R ₆₄ are optionally joined to one another through a first linking group to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group Can,
R ₆₅ and R ₆₆ are optionally joined to one another through a first linking group to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group Can,
b1 to b3 independently of one another are 0, 1, 2 or 3 and when b1 is 0, * - (T ₁ ) _b1 - * is a single bond, and when b2 is 0 * - (T ₂ ) _b2 - * is a single bond, and when b3 is 0, * - (T ₃ ) _{b 3} - * '
Z ₁ to Z ₄ are independently selected from the group consisting of the group represented by the formula (2A), the group represented by the formula (2B), the group represented by the formula (2C) and the group represented by the formula (2)
c1 to c4 are independently selected from the integers of 0 to 5, the sum of c1 to c4 is 1 or more,
R ₁ to R ₄ , R ₅₁ to R ₅₃ and R ₆₁ to R ₆₆ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , a hydroxyl group, A substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆ alkyl group, a substituted or unsubstituted C ₂ -C ₆ alkenyl group, a substituted or unsubstituted C ₂ -C ₆ 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 group, a substituted addition A condensed polycyclic aromatic group, a substituted or unsubstituted non-1-unsubstituted monovalent condensed polycyclic non-aromatic heterocyclic _{group, -N (Q 1) (Q} 2), -Si (Q 3) (Q 4) (Q _{5), -B (Q 6)} (Q 7) , and _{-P (= O) (Q 8} ) (Q 9) doedoe choose from, provided independently of each other R ₅₁ and R ₅₂ of formula 2A, a substituted or unsubstituted 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 heterocyclo A substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent heterocyclic group Is selected from non-aromatic heterocyclic polycyclic groups,
a1 to a4 are each independently selected from integers of 0 to 5,
two of a1 of R ₁ is optionally, be connected to each other, may form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group, or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
two of a2 of R ₂ is optionally, be connected to each other, may form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group, or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
two of a3 of R ₃ is optionally, be connected to each other, may form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group, or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
two of a4 of R ₄ is optionally, be connected to each other, may form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group, or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
Two or more of the neighboring R ₁ to R ₄ may optionally be bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group Can,
Two of R ₅₁ to R ₅₃ may optionally be bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group ,
* Is the binding site with neighboring atoms,
The substituted C ₅ -C ₃₀ carbocyclic group, a substituted C ₁ -C ₃₀ heterocyclic group, a substituted C ₁ -C ₆₀ alkyl group, a substituted C ₂ -C ₆₀ alkenyl, substituted C ₂ -C _A substituted C ₁ -C ₆ 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 cycloalkenyl group, a substituted C ₁ -C ₁₀ cycloalkenyl group, -C ₁₀ hetero 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, , The substituted monovalent non-aromatic condensed polycyclic group and the substituted 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 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, an amidino group, a hydrazine group, a hydrazone jongi, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, 1 (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, and C _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 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 condensed polycyclic group, - _{N (Q 21) (Q 22} ), -Si (Q 23) (Q 24) (Q 25), -B (Q 26) (Q 27) and _{-P (= O) (Q 28} ) (Q 29) at least one selected from the substituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ Group-, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic group, fused polycyclic; 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 );
&Lt; / RTI &gt;
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, group, a nitro group, an amidino group, a hydrazine group, a hydrazone jongi, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ alkyl and C ₆ -C ₆₀ aryl group, at least one substituted C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group of, C ₆ -C ₆₀ aryl A C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocyclic polycyclic group. The method according to claim 1,
X &lt; ₁ &gt; is O,
X ₂ and X ₄ are N, X ₃ is C,
And the bond between X ₂ and X ₄ and M and M bond between the coordinate bond, and the bond is a covalent bond between X and M _3,
And Y ₁ to Y ₇ are C. . The method according to claim 1,
CY ₁ to CY ₄ are independently selected from the group consisting of a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, 1,2,3,4- A thiophene group, a furane group, an indole group, a benzophenol group, a benzophorpol group, an indene group, a benzoylol group, a benzoylmol group, a benzothiophene group, A dibenzothiophene group, a dibenzothiophene group, a dibenzothiophene group, a dibenzothiophene group, a dibenzothiophene group, a dibenzothiophene group, a dibenzothiophene group, a dibenzothiophene group, Naphthene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azacavazole group, azadibenzo borole group, Dibenzo phosphole group, azafluorene group, azadivene group, Azaindibenzothiophene group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group , Azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group , An imidazole group, an imidazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, Benzoimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline (5,6,7,8-tetrahydroisoquinoline) Group and 5,6,7,8-tetrahydroquinoline (5,6,7,8-tetrah ydroquinoline. &lt; / RTI &gt; The method according to claim 1,
T ₁ is _{* -N [(L 61) a61} - (R 61)] - * ', * -B (R 61) - *', * -P (R 61) - * ', * -C (R 61 ) (R ₆₂₎ - is selected from, * -S- * 'and * -O- *', - * ' *, * -Si (R 61) (R 62)'
T ₂ is _{* -N [(L 63) a63} - (R 63)] - * ', * -B (R 63) - *', * -P (R 63) - * ', * -C (R 63 * -S- (R ₆₃ ) - (R ₆₄ ) -, -Si (R ₆₃ ) (R ₆₄ )
T ₃ is _{* -N [(L 65) a65} - (R 65)] - * ', * -B (R 65) - *', * -P (R 65) - * ', * -C (R 65 (R ₆₆ ) -, -Si (R ₆₅ ) (R ₆₆ ) -, -S- * and -O- *
b1 to b3 are, independently of each other, 0 or 1,
b1 + b2 + b3 is 0, 1 or 2. &lt; / RTI &gt; The method according to claim 1,
b1 = 0, b2 = 0 and b3 = 0;
b1 = 1, b2 = 0 and b3 = 0;
b1 = 0, b2 = 1 and b3 = 0;
b1 = 0, b2 = 0 and b3 = 1;
b1 = 1, b2 = 1 and b3 = 0; or
b1 = 1, b2 = 0 and b3 = 1;
b1 = 0, b2 = 1 and b3 = 1. The method according to claim 1,
c1 = 1, c2 = 0, c3 = 0 and c4 = 0;
c1 = 0, c2 = 1, c3 = 0 and c4 = 0;
c1 = 0, c2 = 0, c3 = 1 and c4 = 0;
c1 = 0, c2 = 0, c3 = 0 and c4 = 1; or
c1 = 0, c2 = 2, c3 = 0 and c4 = 0. The method according to claim 1,
R ₁ to R ₄ , R ₅₁ to R ₅₃ and R ₆₁ to R ₆₆ 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 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, An adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo [2.2.2] octyl group, a phenyl group, a naphthyl group A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of a methyl group, an ethyl group, a t-butyl group, a pyridinyl group, and a pyrimidinyl group;
A cyclopentyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, Anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, klychenyl group, pyrrolyl group, thiophenyl group, thiophenyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, a pyrazolyl group, A benzoimidazolyl group, a benzoimidazolyl group, a benzoimidazolyl group, a benzoimidazolyl group, a benzoimidazolyl group, a benzoimidazolyl group, an imidazolyl group, an indolyl group, an indolyl group, A furanyl group, a benzothiophenyl group, an isobenzothiazolyl group , A benzooxazolyl 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 imidazolopyrimidinyl 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 cyclohexyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptyl group, a cycloheptyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, 2] octyl 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, a klychenyl group, a pyrrolyl group, a thiophenyl group, A thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrimidinyl group, A heterocyclic group, a phenanthroline group, a phenanthroline group, an imidazolyl group, an indolyl group, an indolyl group, an indazolyl group, a fluorenyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, A thiazolyl group, an oxadiazolyl group, a triazinyl group, a diazonaphthyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, A cyclohexyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, a cyclopentyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, A cyclohexyl group, a cycloheptenyl group, a bicyclo [2.2.2] octyl group, a phenyl group, a cyclohexyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, Naphthyl group, fluoro A pyranyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, an isothiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, A thiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, A benzoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, , Isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl And an imidazopyrimidinyl group; And
_{-N (Q 1) (Q 2} ), -Si (Q 3) (Q 4) (Q 5), -B (Q 6) (Q 7) , and _{-P (= O) (Q 8} ) (Q 9 );
, Provided that R ₅₁ and R ₅₂ in the formula (2A) are, independently of each other,
A cyclopentyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, Anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, klychenyl group, pyrrolyl group, thiophenyl group, thiophenyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, a pyrazolyl group, A benzoimidazolyl group, a benzoimidazolyl group, a benzoimidazolyl group, a benzoimidazolyl group, a benzoimidazolyl group, a benzoimidazolyl group, an imidazolyl group, an indolyl group, an indolyl group, A furanyl group, a benzothiophenyl group, an isobenzothiazolyl group , A benzooxazolyl 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 imidazolopyrimidinyl group; And
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, 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 cyclohexyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptenyl group, a cycloheptyl group, a cycloheptyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, 2] octyl 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, a klychenyl group, a pyrrolyl group, a thiophenyl group, A thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrimidinyl group, A heterocyclic group, a phenanthroline group, a phenanthroline group, an imidazolyl group, an indolyl group, an indolyl group, an indazolyl group, a fluorenyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, A thiazolyl group, an oxadiazolyl group, a triazinyl group, a diazonaphthyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, A cyclohexyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, a cyclopentyl group, a cycloheptyl group, a cycloheptyl group, a cycloheptyl group, A cyclohexyl group, a cycloheptenyl group, a bicyclo [2.2.2] octyl group, a phenyl group, a cyclohexyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, Naphthyl group, fluoro A pyranyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, an isothiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, A thiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, A benzoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, , Isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl And an imidazopyrimidinyl group;
, 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
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 ₁ to R ₄ , R ₅₁ to R ₅₃ and R ₆₁ to R ₆₆ 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 , groups represented by the following formulas (9-1) to (9-20), and groups represented by the following formulas , Provided that R ₅₁ and R ₅₂ in the formula (2A) are selected from the group consisting of the following chemical formulas 10-1 to 10-4, 10-9, 10-10 and 10-13 to 10-141,

In Formulas 9-1 to 9-20 and 10-1 to 10-142, * denotes a binding site with neighboring atoms, Ph denotes a phenyl group, and TMS denotes a trimethylsilyl group. The method according to claim 1,
In the above formula

Is an organometallic compound selected from the group consisting of the following chemical formulas CY1-1 to CY1-26:

Among the above-mentioned formulas CY1-1 to CY1-26
X ₁₉ is C (R ₁₈ ) (R ₁₉ ), N (R ₁₈ ), O, S or Si (R ₁₈ ) (R ₁₉ )
Y ₁ , Z ₁ and R ₁ are each as defined in claim 1,
R ₁₁ to R ₁₉ each refer to the description of R ₁ in the first paragraph,
d1 and e1 are independently selected from integers of from 0 to 2,
* And * are independent sites of bonding to neighboring atoms. The method according to claim 1,
In the above formula

Is an organic metal compound selected from the group consisting of the following chemical formulas CY2-1 to CY2-8:

Among the above-mentioned formulas CY2-1 to CY2-8
X ₂ , Z ₂ and R ₂ are each as defined in claim 1,
d2 and e2 are each independently selected from an integer of 0 to 2,
* * 'And *' are independent sites of bonding to neighboring atoms. The method according to claim 1,
In the above formula

Is an organometallic compound selected from the group consisting of the following chemical formulas CY3-1 to CY3-12:

Among the above-mentioned formulas CY3-1 to CY3-12
And X ₃₉ are _{C (R 38) (R 39} ), N (R 38), O, S , or _{Si (R 38) (R 39} ),
X ₃ , Z ₃ and R ₃ are each as defined in claim 1,
R ₃₈ and R ₃₉ each refer to the description of R ₃ in the first paragraph,
d3 and e3 are each independently selected from an integer of 0 to 2,
* * 'And *' are independent sites of bonding to neighboring atoms. The method according to claim 1,
In the above formula

Is selected from the group consisting of the groups represented by the following formulas CY4-1 to CY4-26,

Among the above-mentioned formulas CY4-1 to CY4-26
X ₄₉ is C (R ₄₈ ) (R ₄₉ ), N (R ₄₈ ), O, S or Si (R ₄₈ ) (R ₄₉ )
X ₄ , Z ₄ and R ₄ are each as defined in claim 1,
R ₄₁ to R ₄₉ each refer to the description of R ₄ in the first paragraph,
d4 and e4 are each independently selected from an integer of 0 to 2,
* And * are independent sites of bonding to neighboring atoms. The method according to claim 1,
In the above formula

Is an organometallic compound selected from the group consisting of the following chemical formulas CY2 (1) to CY2 (18)

Among the above-mentioned formulas CY2 (1) to CY2 (18)
X ₂ and Z ₂ are as defined in claim 1, and the description of Z _2a and Z _2b respectively refers to the description of Z ₂ in the first paragraph,
Description of the R _2, see what described in claim 1 and, R _2a, and a description of the R _2b are, but see the description of the R ₂ of each of the 1, R _2, R _2a and R _2b is other than hydrogen ,
*, * 'And *' are binding sites with neighboring atoms, respectively. The method according to claim 1,
An organometallic compound represented by the following formula (1-1):
&Lt; Formula 1-1 >

In Formula 1-1,

Is selected from the group consisting of the following formulas CY2 (1) to CY2 (18)
T ₁ is _{* -N [(L 61) a61} - (R 61)] - * ', * -B (R 61) - *', * -P (R 61) - * ', * -C (R 61 ) (R ₆₂₎ - is selected from, * -S- * 'and * -O- *', - * ' *, * -Si (R 61) (R 62)'
T ₂ is _{* -N [(L 63) a63} - (R 63)] - * ', * -B (R 63) - *', * -P (R 63) - * ', * -C (R 63 * -S- (R ₆₃ ) - (R ₆₄ ) -, -Si (R ₆₃ ) (R ₆₄ )
T ₃ is _{* -N [(L 65) a65} - (R 65)] - * ', * -B (R 65) - *', * -P (R 65) - * ', * -C (R 65 (R ₆₆ ) -, -Si (R ₆₅ ) (R ₆₆ ) -, -S- * and -O- *
b1 = 0, b2 = 0 and b3 = 0;
b1 = 1, b2 = 0 and b3 = 0;
b1 = 0, b2 = 1 and b3 = 0;
b1 = 0, b2 = 0 and b3 = 1;
b1 = 1, b2 = 1 and b3 = 0; or
b1 = 1, b2 = 0 and b3 = 1;
b1 = 0, b2 = 1 and b3 = 1,
_{M, X 1, Z 1,} Z 3, Z 4, R 1, R 3, R 4, L 61, L 63, L 65, a61, a63, a65, a description of the R ₆₁ to R ₆₆ are each the first &Lt; / RTI &gt;
d1, d3, d4, e1, e3 and e4 are each independently selected from integers from 0 to 2:

Among the above-mentioned formulas CY2 (1) to CY2 (18)
X ₂ and Z ₂ are each as defined in claim 1, and the description of Z _2a and Z _2b respectively refer to the description of Z ₂ in the first paragraph,
Description of the R _2, see what described in claim 1 and, R _2a, and a description of the R _2b are, but see the description of the R ₂ of each of the 1, R _2, R _2a and R _2b is other than hydrogen ,
*, * 'And *' are binding sites with neighboring atoms, respectively. The method according to claim 1,
An organometallic compound selected from the following compounds 1 to 24:

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;
/ RTI &gt;
Wherein the organic layer contains at least one organometallic compound of any one of claims 1 to 15. 17. The method of claim 16,
Wherein the first electrode is an anode,
The second electrode is a cathode,
Wherein the organic layer further comprises 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 comprises a hole injecting layer, a hole transporting layer, an electron blocking layer or any combination thereof,
Wherein the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. 17. The method of claim 16,
Wherein the organic metal compound is contained in the light emitting layer. 19. The method of claim 18,
Wherein the light emitting layer further comprises a host, and the content of the host in the light emitting layer is larger than the content of the organic metal compound in the light emitting layer. A diagnostic composition comprising at least one organometallic compound according to any one of claims 1 to 15.

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