KR20150068893A - Amine-based compounds and organic light-emitting device comprising the same - Google Patents

Abstract

Disclosed are amine-based compounds and an organic light emitting device comprising the same. The organic light emitting device comprises a first electrode; a second electrode; and an organic layer interposed between the first electrode and the second electrode.

Description

Amine-based compounds and organic light-emitting devices comprising same

Embodiments of the present invention relate to an amine compound and an organic light emitting device including the same.

An organic light-emitting device is a self-light-emitting device having a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed characteristics, and being able to have multiple colors .

A hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially formed on the first electrode in the organic light emitting device. Lt; / RTI > structure. The holes injected from the first electrode migrate to the light emitting layer via the hole transporting region and electrons injected from the second electrode migrate to the light emitting layer via the electron transporting region. The carriers such as holes and electrons recombine in the light emitting layer region to generate an exiton. This exciton changes from the excited state to the ground state and light is generated.

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

One embodiment of the present invention discloses an amine-based compound represented by the following Formula 1:

≪ Formula 1 >

In Formula 1,

X ₁₁ is an oxygen atom (-O-) or a sulfur atom (-S-);

L ₁₁ to L ₁₃ independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cyclo Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene groups, substituted or unsubstituted C ₆ -C ₆₀ arylene groups, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene groups, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene groups, Substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic group (substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic group) );

a11 to a13 are independently selected from 0, 1, 2 and 3;

R ₁₁ to R ₁₆ 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 , A substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent A non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group;

n11 to n13 are independently selected from 0, 1 and 2, and the sum of n11, n12 and n13 is selected from 2, 3, 4, 5 and 6;

R ₁₇ to R ₁₉ independently represent hydrogen, deuterium, F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, Or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ A substituted or unsubstituted C ₁ -C ₁₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-direction Condensed polycyclic group, a substituted or unsubstituted 1, a non-aromatic heterocyclic is selected from a condensed polycyclic group, and _{-Si (Q 1) (Q 2} ) (Q 3);

The substituted C ₃ -C ₁₀ cycloalkylene group, the substituted C ₁ -C ₁₀ heterocycloalkylene group, the substituted C ₃ -C ₁₀ cycloalkenylene group, the substituted C ₁ -C ₁₀ heterocycloalkenylene group, the substituted a C ₆ -C ₆₀ aryl group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted divalent non-aromatic condensed polycyclic group, a substituted bivalent non-condensed polycyclic aromatic heterocyclic group, a substituted C ₁ -C ₆₀ A substituted C ₂ -C ₆₀ alkenyl group, a substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₁ -C ₁₀ hetero A substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted C ₆ -C ₆₀ aryl group, a substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl groups, substituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic hydrocarbon ring, at least one condensed polycyclic group Substituents,

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

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

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

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

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

Q ₁ to Q _3, Q ₁₁ to Q _17, Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are, each independently, hydrogen, C ₁ -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ together An aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocyclic polycyclic group.

Another embodiment of the present invention is a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode and including a light emitting layer; And the organic layer includes at least one selected from amine-based compounds as described above.

In the present embodiment, the host may be an anthracene-based compound represented by the following general formula (2)

(2)

In Formula 2,

L ₂₁ represents a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene groups, substituted or unsubstituted C ₆ -C ₆₀ arylene groups, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene groups, substituted or unsubstituted divalent non-aromatic A condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic group;

a21 is selected from 0, 1, 2 and 3;

R ₂₁ to R ₂₃ independently represent hydrogen, deuterium, F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, hwandoen C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, A substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non- An aromatic heterocyclic polycyclic group, -N (Q ₁ ) (Q ₂ ), -Si (Q ₃ ) (Q ₄ ) (Q ₅ ) and -B (Q ₆ ) (Q ₇ );

b21 to b23 are independently of each other selected from 1, 2, 3, 4, 5 and 6;

n21 is selected from 1, 2, and 3;

The substituted C ₃ -C ₁₀ cycloalkylene group, the substituted C ₁ -C ₁₀ heterocycloalkylene group, the substituted C ₃ -C ₁₀ cycloalkenylene group, the substituted C ₁ -C ₁₀ heterocycloalkenylene group, the substituted a C ₆ -C ₆₀ aryl group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted divalent non-aromatic condensed polycyclic group, a substituted bivalent non-condensed polycyclic aromatic heterocyclic group, a substituted C ₁ -C ₆₀ Substituted C ₂ -C ₆₀ alkenyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₆ -C ₆₀ aryl group, a substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl groups, substituted monovalent non-aromatic condensed polycyclic groups, and substituted monovalent non-aromatic hydrocarbon ring condensed at least one substituent of the polycyclic group,

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

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

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

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

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

Q ₁ to Q _7, Q ₁₁ to Q _17, Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are, each independently, hydrogen, C ₁ -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ together An aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocyclic polycyclic group.

The organic light emitting device including the amine compound may have high efficiency, low driving voltage and long life.

1 is a cross-sectional view schematically showing a structure of an organic light emitting diode according to an embodiment.

The amine compound is represented by the following formula (1): < EMI ID =

≪ Formula 1 >

In the general formula (1), X ₁₁ may be an oxygen atom (-O-) or a sulfur atom (-S-).

For example, in Formula 1, X ₁₁ may be an oxygen atom, but is not limited thereto.

In Formula 1, L ₁₁ to L ₁₃ independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl alkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl, A substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic group;

The substituted C ₃ -C ₁₀ cycloalkylene group, the substituted C ₁ -C ₁₀ heterocycloalkylene group, the substituted C ₃ -C ₁₀ cycloalkenylene group, the substituted C ₁ -C ₁₀ heterocycloalkenylene group, the substituted At least _one substituent of the substituted C ₆ -C ₆₀ arylene group, the substituted C ₁ -C ₆₀ heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group and the substituted divalent non-aromatic heterocyclic polycyclic group,

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

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

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

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

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

Q ₁₁ to Q _17, Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are, each independently, hydrogen, C ₁ -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group, C ₁ to each other - C ₆₀ heteroaryl group, a monovalent non-aromatic heterocyclic group may be selected from a condensed polycyclic group, aromatic condensed polycyclic group, and 1 is non.

For example, in the above formula (1), L ₁₁ to L ₁₃ independently represent a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, A heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenyl group, a benzenesulfonyl group, A phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a phenanthrene group, a phenanthrene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, A pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexaethylene group, A hexacenylene group, a pentacenylene group, a rubicenylene group, a norbornene group, A pyrolylene group, a thiophenylene group, a furanylene group, an imidazolylene group, a pyrazolylene group, an imidazolylene group, a pyrazolylene group, A thiazolylene group, an isothiazolylene group, an oxazolylene group, an isooxazolylene group, a pyridinylene group, a pyrazinylene group, A pyrimidinylene group, a pyridazinylene group, an isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinoline group, A quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinolinylene group, A quinazolinylene group, a cinnolinylene group, a carbazolyl group, a phenanthridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzoimidazolylene group, a benzopyranylene group, a phenanthridinylene group, a phenanthridinylene group, benzofuranylene group, a benzothiophenylene group, an isobenzothiazolylene group, a benzooxazolylene group, an isobenzooxazolylene group, a triazolylene group, A tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group and a di Benzocarbazolylene group; And

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

As another example, in the above formula (1), L ₁₁ to L ₁₃ independently represent a phenyl group, a naphthylene group, a fluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, A phenylene group, a phenylene group, a furanylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, an indolylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a naphthyridinylene group, , A quinazolinylene group, a cinnolinylene group, a carbazolylene group, a phenanthridinylene group, a benzoimidazolylene group, a benzofuranylene group, a benzothiophenylene group, a triazolylene group, a dibenzofuranylene group and a dibenzothiophenyl group Rengi; And

A halogen atom, a hydroxyl group, a hydrogen atom, a deuterium atom, -F, -Cl, -Br, -I, or a salt thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spy-fluorenyl group, a fluorenyl group benzo, dibenzo-fluorenyl group, a phenanthrenyl group, An anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, A phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a pyrrolylene group, a thiophenylene group, a furanylene group, a pyridinyl group, a phenanthrenyl group, A phenylene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, A benzoimidazolyl group, a benzoimidazolyl group, a benzoimidazolyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, Furanylene group, benzothiophenylene group, triazolylene group, dibenzofuranylene group and dibenzothiophenylene group; , But is not limited thereto.

As another example, in the above formula (1), L ₁₁ to L ₁₃ may independently be represented by any one of the following formulas (3-1) to (3-31), but is not limited thereto:

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

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

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

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

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

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

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

a35 is selected from 1, 2 and 3;

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

As another example, in the above formula (1), L ₁₁ to L ₁₃ independently represent any one of the above formulas (3-1) to (3-31);

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

R ₃₁ to R ₃₄ each independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a methyl group, an ethyl group, a tert-butyl group, a methoxy group, an ethoxy group, , A fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klychenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group , A pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group, but is not limited thereto.

As another example, in the above formula (1), L ₁₁ to L ₁₃ may independently be represented by any one of the following formulas (4-1) to (4-56), but are not limited thereto:

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

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

As another example, in the above formula (1), L ₁₁ to L ₁₃ may be independently selected from the above-mentioned formulas 4-1 to 4-8, 4-12 to 4-26 and 4-39 to 4-56 , But is not limited thereto.

In formula (1), a11 represents the number of L ₁₁ , and may be selected from 0, 1, 2, and 3. For example, in Formula 1, a11 may be selected from 0 and 1, but is not limited thereto. When a11 is 0, L ₁₁ is a single bond. When a11 is 2 or more, 2 or more L < ₁₁ > may be the same or different from each other. The description of a12 and a13 can be understood with reference to the description of a11 and the structure of the formula (1).

For example, in the above formula (1), a12 and a13 may be independently selected from 0 and 1, but are not limited thereto.

As another example, in formula (1), the sum of a11, a12 and a13 may be selected from 0, 1 and 2, but is not limited thereto.

In the formula (1), R ₁₁ to R ₁₆ 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 cycloalkyl group, C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl groups, substituted or An unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group;

The substituted C ₃ -C ₁₀ cycloalkyl, substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted C ₆ - At least one substituent of a substituted or unsubstituted C ₁ -C ₆₀ aryl group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group,

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

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

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

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

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

Q ₁₁ to Q _17, Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are, each independently, hydrogen, C ₁ -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group, C ₁ to each other - C ₆₀ heteroaryl group, a monovalent non-aromatic heterocyclic group may be selected from a condensed polycyclic group, aromatic condensed polycyclic group, and 1 is non.

For example, in the general formula (1), R ₁₁ to R ₁₆ independently represent a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, an indacenyl group, an acenaphthyl group, , A spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, A thiophenyl group, an imidazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, , A thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, An isoquinolinyl group, a carbazolyl group, a benzoquinolinyl group, a phthalo A phenanthrolinyl group, a phenanthryl group, a benzimidazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzoquinazolinyl group, a phenanthridinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, A benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofurano group, A phenyl group, a dibenzoylsilyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group; And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an hethtalenyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a thienyl group, a thienyl group, a thienyl group, A thiophene group, a furanyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, A pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, A pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a benzoquinolinyl group, a phthalazinyl group, A benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, A thiazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzofuranyl group, a benzothiopyranyl group, a benzothiophenol group, Substituted with at least one of -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ), benzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and -Si A phenyl group, a pentenyl group, an indenyl group, a naphthyl group, A phenanthrenyl group, a phenanthrenyl group, anthracenyl group, fluororanyl group, anthracenyl group, anthracenyl group, anthracenyl group, an acenaphthyl group, a fluorenyl group, a spioro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, A perylene group, a pentenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a corenylenyl group, an ovalenyl group, a pivalenyl group, a pivalenyl group, , Pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl An isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, A quinazolinyl group, a benzoquinazolinyl group, a cyano group, a phenanthrene group, A benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, a tetrazolyl group, a tetrazolyl group, a tetrazolyl group, a tetrazolyl group, An oxadiazolyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyridinyl group, an imidazopyridinyl group, a thiadiazolyl group, a thiadiazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzothiazolyl group, A diazopyrimidinyl group; ;

Q ₃₃ to Q ₃₅ may be independently selected from a C ₁ -C ₆₀ alkyl group and a C ₆ -C ₆₀ aryl group, but are not limited thereto.

As another example, in the general formula (1), R ₁₁ to R ₁₆ independently represent a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrrolyl group, a thiophenyl group, A pyridinyl group, a pyrimidinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinolinyl group, a phenanthridinyl group, A phenanthrolinyl group, a phenazinyl group, a benzofuranyl group, a benzothiophenyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group and a dibenzoylsilyl group;

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, A pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, a pyrazinyl group, a pyrazinyl group, a pyridinyl group, possess group and a _{-Si (Q 33) (Q 34} ) (Q 35) of the at least one substituted phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylmethyl group LES, a pyrrolyl group, a thiophenyl group , A furanyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, A phenanthrolinyl group, a phenazinyl group, a benzofuranyl group, a benzothiophenyl group, a triazinyl group, a dibenzoyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, A furanyl group, a dibenzothiophenyl group and a dibenzoylsilyl group; And

A phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, or a phenanthrenyl group substituted with at least one of C ₁ -C ₂₀ alkyl groups substituted with at least one of deuterium, -F, -Cl, -Br, A thiophenyl group, a pyranyl group, a pyridinyl group, a pyranyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a naphthyridinyl group, a quinoxalinyl group A phenanthrolinyl group, a phenazinyl group, a benzofuranyl group, a benzothiophenyl group, a triazinyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, Silol diary; ;

Q ₃₃ to Q ₃₅ may be independently selected from a C ₁ -C ₂₀ alkyl group and a C ₆ -C ₆₀ aryl group, but are not limited thereto.

As another example, in the general formula (1), R ₁₁ to R ₁₆ independently represent a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, A quinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a sienolinyl group, a triazinyl group, a dibenzofuranyl group and a dibenzothiophenyl group; And

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, C ₁ -C ₂₀ alkyl group, -CCD ₃ , -CF ₃ , C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorene Anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinone A phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, a pyridinyl group, a pyrazinyl group which is substituted with at least one of -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ) Group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, , Triazinyl group, dibenzofuranyl group and dibenzothiophenyl group;

Q ₃₃ to Q ₃₅ independently represent a methyl group, an ethyl group, a ter-butyl group, a phenyl group, and a naphthyl group; , But is not limited thereto.

As another example, in the above formula (1), R ₁₁ to R ₁₆ may be independently selected from the following formulas (5-1) to (5-33), but are not limited thereto:

Of the above formulas (5-1) to (5-33)

Y ₅₁ is selected from C (R ₅₃ ) (R ₅₄ ), N (R ₅₃ ), O and S;

R ₅₁ to R ₅₄ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, A sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, -CD ₃ , -CF ₃ , a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, A phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klychenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group , Quinoxalinyl group, quinazolinyl group, carbazolyl group, triazinyl group, -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ); And

Q ₃₃ to Q ₃₅ independently represent a methyl group, an ethyl group, a tert-butyl group, a phenyl group and a naphthyl group; ;

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

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

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

a54 is selected from 1, 2 and 3;

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

* Is the binding site with neighboring atoms.

As another example, in the above formula (1), R ₁₁ to R ₁₆ may be independently selected from the following formulas (6-1) to (6-155), but are not limited thereto:

Among the formulas (6-1) to (6-155)

t-Bu is a tert-butyl group;

Ph is a phenyl group;

* Is the binding site with neighboring atoms.

As another example, in the above formula (1), R ₁₁ to R ₁₆ may be independently selected from the above-mentioned formulas (6-1) to (6-42) and (6-140) to (6-155), but are not limited thereto.

로 표시되는 모이어티의 개수를 나타낸 것으로서, 0, 1 및 2 중에서 선택될 수 있다. n11이 2 이상일 경우 2 이상의

로 표시되는 모이어티는 서로 동일하거나 상이할 수 있다. n12 및 n13에 대한 설명은 n11에 대한 설명 및 화학식 1의 구조를 참조하여 이해될 수 있다.In the above formula (1), n11 is

And may be selected from 0, 1, and 2, respectively. When n11 is 2 or more, 2 or more

May be the same or different from each other. The description of n12 and n13 can be understood with reference to the description of n11 and the structure of the formula (1).

For example, in the above formula (1), n11 to n13 may be independently selected from 0 and 1, but are not limited thereto.

In Formula 1, the sum of n11, n12, and n13 may be selected from 2, 3, 4, 5, and 6.

For example, in Formula 1, the sum of n11, n12, and n13 may be selected from 2, 3, and 4, but is not limited thereto.

As another example, in Formula 1, the sum of n11, n12 and n13 may be selected from 1 and 2, but is not limited thereto.

As another example, in Formula 1, the sum of n11, n12 and n13 may be 2, but is not limited thereto.

As another example, in the above formula (1), n11 may be 1, n12 may be 0, and n13 may be 1, but is not limited thereto.

Wherein R ₁₇ to R ₁₉ independently represent hydrogen, deuterium, F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, A sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C 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 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, a substituted or unsubstituted C ₆ -C ₆₀ A substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, A substituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group, and -Si (Q ₁ ) (Q ₂ ) (Q ₃ );

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

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

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

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

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

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

Q ₁ to Q _3, Q ₁₁ to Q _17, Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are, each independently, hydrogen, C ₁ -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ together An aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocyclic polycyclic group.

For example, in Formula 1, R ₁₇ to R ₁₉ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, , 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 ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic hydrocarbon ring selected from a condensed polycyclic group, and _{-Si (Q 1) (Q 2} ) (Q 3) and;

Q ₁ to Q ₃ are, independently of each other, a C ₁ -C ₆₀ alkyl group and a C ₆ -C ₆₀ aryl group; , But is not limited thereto.

As another example, In the formula 1, R ₁₇ to R ₁₉ are independently, hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, cyano, nitro, C ₁ -C ₆₀ alkyl group, C ₁ to each other -C ₆₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, benzo fluorenyl group, an anthracenyl group, pie LES group, Cry hexenyl group, a pyridinyl group, the groups possess, pyrimidinyl group, pyridyl group pyrazinyl, quinolyl An isoquinolinyl group, a carbazolyl group, a triazinyl group, -Si (CH ₃ ) ₃ and -Si (Ph) ₃ , but is not limited thereto.

As another example, in the above formula (1), R ₁₇ to R ₁₉ may be hydrogen, but are not limited thereto.

In another embodiment, the amine compound represented by Formula 1 may be represented by the following Formula 1-1, but is not limited thereto:

≪ Formula 1-1 >

In Formula 1-1,

X ₁₁ , L ₁₁ , L ₁₃ , a11, a13, R ₁₁ , R ₁₂ , R ₁₅ and R ₁₆ refer to the foregoing.

For example, in Formula 1-1, L ₁₁ and L ₁₃ may be independently selected from the following Formulas 4-1 to 4-56, but are not limited thereto.

For example, in Formula 1-1, R ₁₁ , R ₁₂ , R _15, and R ₁₆ may be independently selected from the above Formulas 6-1 to 6-155, but are not limited thereto.

In another embodiment, the amine compound represented by Formula 1 may be represented by the following Formula 1-1A, but is not limited thereto:

≪ Formula (1-1A)

In the above formula (1-1A)

X ₁₁ , L ₁₁ , L ₁₃ , a11, a13, R ₁₁ , R ₁₂ , R ₁₅ and R ₁₆ refer to the foregoing.

For example, in Formula 1-1A, L ₁₁ and L ₁₃ may be independently selected from the following Formulas 4-1 to 4-56, but are not limited thereto.

For example, R ₁₁ , R ₁₂ , R ₁₅ and R ₁₆ in the formula (1-1A) may be independently selected from the above-mentioned formulas (6-1) to (6-155), but are not limited thereto.

For example, the amine compound represented by Formula 1 may be selected from the following compounds 1 to 162, but is not limited thereto:

The amine compound represented by Formula 1 includes a core (see Formula 1 below) in which benzene and crysene are connected through an oxygen atom or a sulfur atom.

≪ Formula (1) >

The amine compound represented by the above formula (1) is in a state in which? -Electrons are delocalized because benzene and crysene are connected to each other through X ₁₁ (wherein X ₁ is an oxygen atom or a sulfur atom). In addition, since the amine compound represented by Formula 1 includes two pairs of unshared electron pairs, X ₁₁ can provide extra electrons to the core.

Accordingly, the amine compound represented by the above formula (1) has a structure in which the π-electrons are abundant in the core, so that the probability of transition π → π * and transition of n → π * increases.

The amine compound represented by Formula 1 may be synthesized using a known organic synthesis method. The method of synthesizing the amine compound can be recognized by those skilled in the art with reference to the following examples.

The amine 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. 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 amine compound represented by Formula 1.

The organic light emitting device includes an organic layer including an amine compound represented by Formula 1, thereby having high efficiency, low driving voltage and long life.

The amine compound represented by Formula 1 may be used between a pair of electrodes of an organic light emitting device. For example, the amine compound may include a light emitting layer, a hole transporting region between the first electrode and the light emitting layer (including at least one of a hole injection layer, a hole transporting layer and an electron blocking layer) between the light emitting layer and the second electrode (For example, at least one of a hole blocking layer, an electron transporting layer, and an electron injection layer) of the electron transporting layer. For example, the amine compound represented by Formula 1 may be included in the light emitting layer. In this case, the light emitting layer may further include a host, and the amine compound included in the light emitting layer may serve as a dopant. The light emitting layer may be a green light emitting layer or a red light emitting layer emitting green light or red light, and the dopant may be a fluorescent dopant.

In the present specification, the phrase "(the organic layer) contains one or more amine-based compounds" means that one or more amine compounds belonging to the general formula (1) Or more of the amine-based compound ".

For example, the organic layer may include only the compound 1 as the amine compound. At this time, the compound 1 may exist in the light emitting layer of the organic light emitting device. Alternatively, the organic layer may include Compound 1 and Compound 2 as the amine compound. In this case, the compound 1 and the compound 2 are present in the same layer (for example, both the compound 1 and the compound 2 may be present in the light emitting layer) or exist in different layers (for example, And compound 2 may be present in the electron transport region).

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

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

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. The organic light emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.

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

A substrate may be further disposed below the first electrode 110 or over the second electrode 190 of FIG. The substrate may be a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness.

The first electrode 110 may be formed, for example, by providing a first electrode material on the substrate using a deposition method, a sputtering method, or the like. When the first electrode 110 is an anode, the first electrode material may be selected from materials having a high work function to facilitate hole injection. The first electrode 110 may be a reflective electrode, a transflective electrode, or a transmissive electrode. As the material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity can be used. (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), or the like is used as the first electrode material for forming the first electrode 110 which is a translucent electrode or a reflective electrode. ), Magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag).

The first electrode 110 may have a single layer or a multilayer structure having a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the present invention is not limited thereto.

An organic layer 150 is disposed on the first electrode 110. The organic layer 150 includes a light emitting layer.

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

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

The hole transporting region may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multi-layered structure having a plurality of layers made of a plurality of different materials.

For example, the hole transporting region may have a single layer structure composed of a plurality of different materials, or may have a structure of a hole injection layer / hole transporting layer, a hole injecting layer / hole transporting layer / buffer layer , A hole injection layer / a buffer layer, a hole transporting layer / a buffer layer, a hole injecting layer / a hole transporting layer / an electron blocking layer, but the present invention is not limited thereto.

When the hole transporting region includes a hole injection layer, a vacuum evaporation method, a spin coating method, a casting method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal imaging (LITI) The hole injection layer may be formed on the first electrode 110 by using various methods.

When the hole injection layer is formed by vacuum deposition, the deposition conditions may include, for example, a deposition temperature of about 100 to about 500 DEG C, a vacuum degree of about 10 ^-8 to about ^10-3 torr, and a deposition rate of about 0.01 to about 100 A / sec The hole injection layer structure to be formed and the hole injection layer structure to be formed within the deposition rate range of the hole injection layer to be formed.

When the hole injection layer is formed by the spin coating method, the coating conditions include a compound for a hole injection layer to be deposited and a hole for formation to be formed within a range of a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature range of about 80 [ Can be selected in consideration of the injection layer structure.

When the hole transporting region includes a hole transporting layer, the hole transporting layer may be formed by a vacuum evaporation method, a spin coating method, a casting method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal imaging The hole transport layer may be formed on the first electrode 110 or on the hole injection layer using various methods. When the hole transport layer is formed by the vacuum deposition method and the spin coating method, the deposition conditions and the coating conditions of the hole transport layer refer to the deposition conditions and the coating conditions of the hole injection layer.

The hole-transporting region may be at least one selected from the group consisting of m-MTDATA, TDATA, 2-TNATA, NPB, beta-NPB, TPD, Spiro- TPD, Spiro- NPB, alpha -NPB, TAPC, HMTPD, TCTA (N-carbazolyl) triphenylamine), Pani / DBSA (polyaniline / dodecylbenzenesulfonic acid), PEDOT / PSS Poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate) / poly (4-styrenesulfonate) / Pani / CSA (polyaniline / camphor sulfonicacid) Styrene sulfonate), PANI / PSS (polyaniline) / poly (4-styrenesulfonate) / poly (4-styrenesulfonate)), a compound represented by the following formula 201 and a compound represented by the following formula can do:

≪ Formula 201 >

≪ EMI ID =

Of the above formulas (201) and (202)

L ₂₀₁ to L ₂₀₅ independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cyclo Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene groups, substituted or unsubstituted C ₆ -C ₆₀ arylene groups, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene groups, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene groups, Aromatic dicarboxylic polycyclic group and substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic group,

The substituted C ₃ -C ₁₀ cycloalkylene group, the substituted C ₁ -C ₁₀ heterocycloalkylene group, the substituted C ₃ -C ₁₀ cycloalkenylene group, the substituted C ₁ -C ₁₀ heterocycloalkenylene group, the substituted At least _one substituent of the substituted C ₆ -C ₆₀ arylene group, the substituted C ₁ -C ₆₀ heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group and the substituted divalent non-aromatic heterocyclic polycyclic group,

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

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, salt, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, 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 ₂₀₁₎ (Q _{202), -Si (Q 203)} (Q 204) (Q 205) and _{-B (Q 206) (Q 207} ) of the at least one substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl groups and C ₁ -C ₆₀ alkoxy group;

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

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A C ₁ -C ₆ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ (Q ₂₁₁ ) (Q ₂₁₂ ), -Si (Q ₂₁₃ ) (Q ₂₁₄ ) (Q ₂₁₅ ), and -Si (Q ₂₁₅ ) _{B (Q 216) (Q 217} ) of the at least one substituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group , C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ A heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group; And

Q ₂₂₁ ( _Q222 ), -Si ( _Q223 ) ( _Q224 ) ( _Q225 ), and -B ( _Q226 ) ( _Q227 ); ;

xa1 to xa4 are independently selected from 0, 1, 2 and 3;

xa5 is selected from 1, 2, 3, 4 and 5;

R ₂₀₁ to R ₂₀₅ independently represent a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, salt, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, 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 ₂₃₁₎ (Q _{232), -Si (Q 233)} (Q 234) (Q 235) and _{-B (Q 236) (Q 237} ) of the at least one substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl groups and C ₁ -C ₆₀ alkoxy group;

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

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A C ₁ -C ₆ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 241) (Q} 242), -Si (Q 243) (Q 244) (Q 245) and - _{B (Q 246) (Q 247} ) of the at least one substituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group , C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ A heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group; ;

Q ₂₀₁ to Q ₂₀₇ , Q ₂₁₁ to Q ₂₁₇ , Q ₂₂₁ to Q ₂₂₇ , Q ₂₃₁ to Q ₂₃₇ and Q ₂₄₁ to Q ₂₄₇ independently of one another are hydrogen, deuterium, -F, -Cl, -Br, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone jongi, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ An alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, salt, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-substituted with at least one of the aromatic condensed polycyclic heterocyclic group, C ₁ - aromatic condensed polycyclic group, and 1 is non- C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl groups and C ₁ -C ₆₀ alkoxy group;

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

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A C ₁ -C ₆ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ C ₃ -C ₁₀ cycloalkyl groups, C ₁ -C ₁₀ heterocycloalkyl groups, C ₃ -C ₁₀ cycloalkyl groups substituted with at least one of a monovalent non-aromatic heterocyclic polycyclic group and a monovalent non-aromatic condensed polycyclic group, cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, 1 Is a non-aromatic condensed polycyclic group and a monovalent Non-aromatic heterocyclic polycyclic groups; .

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

L ₂₀₁ to L ₂₀₅ independently represent a group selected from the group consisting of a phenylene group, a naphthylrenylene group, a fluorenylene group, a spiro-fluorenrenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, A phenylene group, a pyrenylene group, a pyrenylene group, a pyrenylene group, a pyrenylene group, a pyrenylene group, a pyrenylene group, a pyrenylene group, a pyrenylene group, A carbazolylene group and a triazylene group; And

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

xa1 to xa4 are, independently of each other, 0, 1 or 2;

xa < 5 > is 1, 2 or 3;

R ₂₀₁ to R ₂₀₅ independently represent a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, A cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, And

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A halogen atom, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an azulenyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, Anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyranyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazole A phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, A pyridinyl group, a pyrazinyl group, a pyrimidinyl group, Florida possess group, a quinolinyl group, an isoquinolinium group, a quinoxalinyl group, a quinazolinyl group, a carbazole group and a triazole group possess; , But is not limited thereto.

The compound represented by Formula 201 may be represented by the following Formula 201A:

≪ Formula 201A >

For example, the compound represented by Formula 201 may be represented by the following Formula 201A-1, but is not limited thereto:

<Formula 201A-1>

The compound represented by the formula (202) may be represented by the following formula (202A), but is not limited thereto:

&Lt; Formula 202A >

The description of L ₂₀₁ to L ₂₀₃ , xa 1 to xa 3, xa 5 and R ₂₀₂ to R ₂₀₄ in the above formulas 201A, 201A-1 and 202A is the same as that described in this specification, and R ₂₁₁ and R ₂₁₂ are the same as R ₂₀₃ R ₂₁₃ to R ₂₁₆ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, jongi, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C _A C ₁ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkenyl group, a C ₆ -C ₆₀ aryl group, a C ₆ -C ₆₀ arylox A C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocyclic polycyclic group; &Lt; / RTI &gt;

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

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

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

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

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

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

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

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

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

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

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

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

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

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

xa5 is 1 or 2;

In the above formulas 201A and 201A-1, R ₂₁₃ and R ₂₁₄ may combine with each other to form a saturated or unsaturated ring.

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

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

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

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

<Compound HT-D1> <F4-TCNQ>

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

A vacuum deposition method, a spin coating method, a casting method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal imaging (LITI) method, or the like is performed on the first electrode 110 or the hole transporting region. ) And the like are used to form a light emitting layer. When the light emitting layer is formed by the vacuum deposition method and the spin coating method, the deposition condition and the coating condition of the light emitting layer refer to the deposition condition and the coating condition of the hole injection layer.

When the organic light emitting device 10 is a full color organic light emitting device, it may be patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer for each light emitting layer and individual sub-pixels. Alternatively, the light emitting layer may have a structure in which a red light emitting layer, a green light emitting layer, and a blue light emitting layer are laminated or a structure in which a red light emitting material, a green light emitting material and a blue light emitting material are mixed without layering, and emits white light. Alternatively, the light emitting layer may be a white light emitting layer, and may further include a color converting layer or a color filter that converts the white light into light of a desired color.

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

Alternatively, the host may include a compound represented by Formula 301 below.

&Lt; Formula 301 >

Ar ₃₀₁ - [(L ₃₀₁ ) _{xb 1} -R ₃₀₁ ] _{xb 2}

In the above formula (301), Ar ₃₀₁ is preferably selected from the group consisting of naphthalene, heptalene, fluorenene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene An anthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, a naphthacene, a picene, a perylene, Pentaphene and indenoanthracene;

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A C ₁ -C ₆ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic group and the condensed polycyclic _{-Si (Q 301) (Q 302} ) (Q 303) ( Q ₃₀₁ to Q ₃₀₃ are the independently from each other, hydrogen , A C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₆ -C ₆₀ aryl group and a C ₁ -C ₆₀ heteroaryl group), naphthalene, heptalene, fluorene, Spiro-fluorene, Ben Fluorene, dibenzo fluorene, page nalren, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, Cry Sen, naphthacene, pisen, perylene, penta pen and indeno anthracene; ;

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

R ₃₀₁ is a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

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

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

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

xb1 is selected from 0, 1, 2 and 3;

xb2 is selected from 1, 2, 3 and 4.

For example, in Formula 301, L ₃₀₁ is preferably a group selected from the group consisting of a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group , Anthracenylene group, pyrenylene group and chrysenylene group; And

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, Naphthylene group, fluorenylene group, spiro-fluorenylene group, benzofluorenylene group, dibenzofluorenylene group, dibenzofluorenylene group, phenanthrene group, and phenanthrene group, which are substituted with at least one member selected from the group consisting of a phenylene group, A threonylene group, an anthracenylene group, a pyrenylene group and a chrysenylene group; ;

R ₃₀₁ is a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

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

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

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, A phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group which is substituted with at least one member selected from the group consisting of a pyridyl group, , A pyrenyl group and a klycenyl group; , But is not limited thereto.

The compound represented by Formula 301 may be represented by the following compounds H1 to H25, but is not limited thereto:

Alternatively, the host may include, but is not limited to, at least one of the following compounds H26 to H32:

For example, the host may comprise an anthracene-based compound represented by the following formula 2:

(2)

In Formula 2,

L ₂₁ represents a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene groups, substituted or unsubstituted C ₆ -C ₆₀ arylene groups, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene groups, substituted or unsubstituted divalent non-aromatic A condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic group;

a21 is selected from 0, 1, 2 and 3; a21 is 2 or more, the plurality of L &lt; ₂₁ &gt; are the same or different from each other;

R ₂₁ to R ₂₃ independently represent hydrogen, deuterium, F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, hwandoen C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, A substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non- An aromatic heterocyclic polycyclic group, -N (Q ₁ ) (Q ₂ ), -Si (Q ₃ ) (Q ₄ ) (Q ₅ ) and -B (Q ₆ ) (Q ₇ );

b21 to b23 are independently of each other selected from 1, 2, 3, 4, 5 and 6;

n21 is selected from 1, 2, and 3;

The substituted C ₃ -C ₁₀ cycloalkylene group, the substituted C ₁ -C ₁₀ heterocycloalkylene group, the substituted C ₃ -C ₁₀ cycloalkenylene group, the substituted C ₁ -C ₁₀ heterocycloalkenylene group, the substituted a C ₆ -C ₆₀ aryl group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted divalent non-aromatic condensed polycyclic group, a substituted bivalent non-condensed polycyclic aromatic heterocyclic group, a substituted C ₁ -C ₆₀ Substituted C ₂ -C ₆₀ alkenyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₆ -C ₆₀ aryl group, a substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl groups, substituted monovalent non-aromatic condensed polycyclic groups, and substituted monovalent non-aromatic hydrocarbon ring condensed at least one substituent of the polycyclic group,

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

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

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

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

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

Q ₁ to Q _7, Q ₁₁ to Q _17, Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are, each independently, hydrogen, C ₁ -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ together An aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocyclic polycyclic group.

For example, in the general formula (2), L ₂₁ represents a group selected from the group consisting of a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptarenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, A phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a cyanecylene group, a phenanthrene group, A phenylene group, a naphthalene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentachenylene group, a rubicecylene group, a coronenylene group, an ovalenylene group, a pyrrolylene group, A pyrimidinyl group, a pyridazinyl group, an isoindole group, an imidazolyl group, an imidazolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, Indolylene, Indolylene, Indazolinyl, Puri A phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, A benzoimidazolyl group, a benzoimidazolyl group, a benzimidazolyl group, a benzimidazolyl group, a benzimidazolyl group, a benzimidazolyl group, a benzimidazolyl group, a benzimidazolyl group, a benzimidazolyl group, Triazolylene group, tetrazolylene group, oxadiazolene group, triazylene group, dibenzofuranyl group, dibenzothiophenylene group, benzocarbazolylene group and dibenzocarbazolylene group; And

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

As another example, in the general formula (2), L ₂₁ is preferably selected from the group consisting of a phenylene group, a naphthylene group, a fluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a carbazolylene group, a dibenzophenanylene group, Thiophenylene group; And

A halogen atom, a hydroxyl group, a hydrogen atom, a deuterium atom, -F, -Cl, -Br, -I, or a salt thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spy-fluorenyl group, a fluorenyl group benzo, dibenzo-fluorenyl group, a phenanthrenyl group, An anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, A phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a carbazolylene group, a dibenzophenanylene group, and a dibenzothiophenyl group, which are substituted with at least one of a phenanthrene group, Rengi; , But is not limited thereto.

As another example, in the above formula (2), L ₂₁ may be selected from the following formulas (3-1) to (3-8) and (3-22) to (3-29)

Of the above formulas (3-1) to (3-8) and (3-22) to (3-29)

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

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

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

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

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

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

a35 is selected from 1, 2 and 3;

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

As another example, in Formula 2, L ₂₁ is represented by any one of Formulas 3-1 to 3-8 and 3-22 to 3-29, and Formulas 3-1 to 3-8 and 3-22, 3-29, R ₃₁ to R ₃₄ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a methyl group, an ethyl group, a tert-butyl group, a methoxy group, an ethoxy group, , A phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klychenyl group, a pyridinyl group, But are not limited to, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group.

As another example, in the above formula (2), L ₂₁ may be selected from among the following formulas (4-1) to (4-11) and (4-31) to (4-54)

Of the above-mentioned formulas 4-1 to 4-11 and 4-31 to 4-54,

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

For example, in Formula 2, a21 may be selected from 0 and 1, but is not limited thereto.

For example, in Formula 2, R ₂₁ and R ₂₂ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, phenyl, pentalenyl, A phenanthrenyl group, an anthracenyl group, a phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a phenanthryl group, an anthracenyl group, a phenanthryl group, A perylene group, a pentacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, a perfluorenyl group, a perfluorenyl group, A thiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, An isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, A benzoquinazolinyl group, a cyano group, a phenanthridinyl group, an acridinyl group, a phenanthroline group, a benzoquinolinyl group, a benzoquinolyl group, a phenanthridinyl group, an acridinyl group, a phenanthroline group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, A benzothiazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, an oxadiazolyl group, an oxadiazolyl group, an oxadiazolyl group, an oxadiazolyl group, An imidazopyrimidinyl group, an -N (Q) -alkyl group, an imidazopyrimidinyl group, an imidazopyrimidinyl group, a benzothiophenyl group, a dibenzothiophenyl group, a dibenzosilyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, ₁ ) (Q ₂ ) and -Si (Q ₃ ) (Q ₄ ) (Q ₅ ); And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an hethtalenyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a thienyl group, a thienyl group, a thienyl group, A thiophene group, a furanyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, A pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, A pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a benzoquinolinyl group, a phthalazinyl group, A benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, A thiazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzofuranyl group, a benzothiopyranyl group, a benzothiophenol group, Substituted with at least one of -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ), benzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and -Si A phenyl group, a pentenyl group, an indenyl group, a naphthyl group, A phenanthrenyl group, a phenanthrenyl group, anthracenyl group, fluororanyl group, anthracenyl group, anthracenyl group, anthracenyl group, an acenaphthyl group, a fluorenyl group, a spioro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, A perylene group, a pentenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a corenylenyl group, an ovalenyl group, a pivalenyl group, a pivalenyl group, , Pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl An isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, A quinazolinyl group, a benzoquinazolinyl group, a cyano group, a phenanthrene group, A benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, a tetrazolyl group, a tetrazolyl group, a tetrazolyl group, a tetrazolyl group, An oxadiazolyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyridinyl group, an imidazopyridinyl group, a thiadiazolyl group, a thiadiazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzothiazolyl group, A diazopyrimidinyl group; ;

Q ₁ to Q ₅ and Q ₃₃ to Q ₃₅ may be independently selected from a C ₁ -C ₆₀ alkyl group and a C ₆ -C ₆₀ aryl group, but are not limited thereto.

As another example, in the general formula (2), R ₂₁ and R ₂₂ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, phenyl group, , Anthracenyl group, triphenylenyl group, pyrrolyl group, thiophenyl group, furanyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, quinolinyl group, isoquinolinyl group, carbazolyl group, naphthyridinyl group, A phenanthrolinyl group, a phenanthryl group, a benzofuranyl group, a benzothiophenyl group, a triazinyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, A benzoylolyl group, -N (Q ₁ ) (Q ₂ ) and -Si (Q ₃ ) (Q ₄ ) (Q ₅ ); And

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, A pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, a pyrazinyl group, a pyrazinyl group, a pyridinyl group, possess group and a _{-Si (Q 33) (Q 34} ) (Q 35) of the at least one substituted phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylmethyl group LES, a pyrrolyl group, a thiophenyl group , A furanyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, A phenanthrolinyl group, a phenazinyl group, a benzofuranyl group, a benzothiophenyl group, a triazinyl group, a dibenzoyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, A furanyl group, a dibenzothiophenyl group and a dibenzoylsilyl group; And

A phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, or a phenanthrenyl group substituted with at least one of C ₁ -C ₂₀ alkyl groups substituted with at least one of deuterium, -F, -Cl, -Br, A thiophenyl group, a pyranyl group, a pyridinyl group, a pyranyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a naphthyridinyl group, a quinoxalinyl group A phenanthrolinyl group, a phenazinyl group, a benzofuranyl group, a benzothiophenyl group, a triazinyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, Silol diary; ;

Q ₁ to Q ₅ and Q ₃₃ to Q ₃₅ may be independently selected from a C ₁ -C ₂₀ alkyl group and a C ₆ -C ₆₀ aryl group, but are not limited thereto.

As another example, in Formula 2, R ₂₁ and R ₂₂ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, phenyl, naphthyl, fluorenyl, phenanthryl A pyridinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzo A thiophenyl group, -N (Q ₁ ) (Q ₂ ) and -Si (Q ₃ ) (Q ₄ ) (Q ₅ ); And

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, C ₁ -C ₂₀ alkyl group, -CCD ₃ , -CF ₃ , C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorene Anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinone A phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, a pyridinyl group, a pyrazinyl group which is substituted with at least one of -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ) Group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, , Triazinyl group, dibenzofuranyl group and dibenzothiophenyl group;

Q ₁ to Q ₅ and Q ₃₃ to Q ₃₅ independently represent a methyl group, an ethyl group, a tert-butyl group, a phenyl group and a naphthyl group; , But is not limited thereto.

As yet another example, In the formula 2, R ₂₁ and R ₂₂ are, each independently, hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, _{cyano, -N (Ph) 2, -Si} (CH another ₃ ) ₃ , -Si (Ph) ₃ and the following formulas (5-1) to (5-9) and (5-33)

Among the above-mentioned formulas (5-1) to (5-9) and (5-33)

Y ₅₁ is selected from C (R ₅₃ ) (R ₅₄ ), N (R ₅₃ ), O and S;

R ₅₁ to R ₅₄ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, A sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, -CD ₃ , -CF ₃ , a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, A phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klychenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group , Isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, triazinyl group and -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ); ;

Q ₃₃ to Q ₃₅ independently represent a methyl group, an ethyl group, a ter-butyl group, a phenyl group, and a naphthyl group; ;

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

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

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

a54 is selected from 1, 2 and 3;

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

* Is the binding site with neighboring atoms.

As another example, in the above formula (2), R ₂₁ and R ₂₂ may be independently selected from the following formulas (6-1) to (6-42) and (6-140) to (6-155)

Among the formulas (6-1) to (6-42) and (6-140) to (6-155)

t-Bu is a tert-butyl group;

Ph is a phenyl group;

* Is the binding site with neighboring atoms.

For example, in the general formula (2), R ₂₃ represents a group selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, , 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 ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group is selected from the aromatic heterocyclic groups and fused polycyclic _{-Si (Q 3) (Q 4} ) (Q 5), 1 is a non-aromatic condensed polycyclic group, a monovalent non;

Q ₃ to Q ₅ are, independently of each other, a C ₁ -C ₆₀ alkyl group and a C ₆ -C ₆₀ aryl group; , But is not limited thereto.

As another example, in the above formula (2), R ₂₃ represents a group selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, nitro, C ₁ -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy, And examples thereof include a phenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, group, a carbazole group, a triazinyl group, -Si (CH _{3) 3} and -Si (Ph) ₃ may be selected from, but is not limited to such.

As another example, in Formula 2, R ₂₃ is selected from among hydrogen, a methyl group, an ethyl group, a tert-butyl group, a methoxy group, an ethoxy group, a terbutoxy group, -Si (CH ₃ ) ₃ , a phenyl group and a naphthyl group But is not limited thereto.

For example, in the above formula (2), b21 to b23 may be independently selected from 1 and 2, but are not limited thereto.

For example, in Formula 2, n21 may be 1, but is not limited thereto.

In another embodiment, the anthracene compound represented by Formula 2 may be selected from the following Formulas 2-1 and 2-2, but is not limited thereto:

&Lt; Formula (2-1)

&Lt; Formula (2-2)

Among the formulas (2-1) and (2-2)

L _21, a21, R ₂₁ to R _23, and b21 to b23, see the foregoing.

In still another embodiment, the anthracene-based compound represented by Formula 2 may be selected from the following Formulas 2-1A and 2-2A, but is not limited thereto:

<Formula 2-1A>

(2-2A)

Of the above formulas (2-1A) and (2-2A)

L _21, a21, R ₂₁ to R _23, and b21 and b22 will see the foregoing.

For example, the anthracene compound represented by Formula 2 may be selected from the following compounds H101 to H188 and H201 to H218, but is not limited thereto:

According to one embodiment, the light emitting layer of the organic light emitting device includes the amine compound represented by Formula 1 as a dopant.

The light emitting layer of the organic light emitting device may further include at least one of a fluorescent dopant and a phosphorescent dopant in addition to the amine compound represented by Formula 1.

The phosphorescent dopant may include an organometallic complex represented by the following formula (401): &lt; EMI ID =

&Lt; Formula 401 >

In the above formula (401)

M is selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thorium (TM);

X ₄₀₁ to X ₄₀₄ independently represent a nitrogen atom or a carbon atom;

The A ₄₀₁ and A ₄₀₂ rings may be, independently of one another, substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted spirofluorene, substituted or unsubstituted indene Substituted or unsubstituted thiophenes, substituted or unsubstituted thiophenes, substituted or unsubstituted furan, substituted or unsubstituted imidazoles, substituted or unsubstituted pyrazoles, substituted or unsubstituted thiols, substituted or unsubstituted thiophenes, Substituted or unsubstituted thiazoles, substituted or unsubstituted isothiazoles, substituted or unsubstituted oxazoles, substituted or unsubstituted isoxazoles, substituted or unsubstituted pyridines, substituted or unsubstituted pyrazines, substituted or unsubstituted pyrimidines, Substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazoline, substituted or unsubstituted quinazoline, substituted or unsubstituted quinazoline, substituted or unsubstituted quinazoline, substituted or unsubstituted quinazoline, substituted or unsubstituted quinazoline, Substituted or unsubstituted benzoimidazoles, substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophenes, substituted or unsubstituted isobenzothiophenes, substituted or unsubstituted benzothiophenes, substituted or unsubstituted benzothiophenes, Substituted or unsubstituted benzoxazole, substituted or unsubstituted benzoxazole, substituted or unsubstituted isobenzoxazole, substituted or unsubstituted triazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted triazine, substituted or unsubstituted dibenzofuran, And substituted or unsubstituted dibenzothiophene;

The substituted benzene, substituted naphthalene, substituted fluorene, substituted spiro-fluorene, substituted indene, substituted pyrrole, substituted thiophene, substituted furan, substituted imidazole, substituted pyrazole, Substituted thiazoles, substituted thiazoles, substituted isothiazoles, substituted oxazoles, substituted isoxazoles, substituted pyridines, substituted pyrazines, substituted pyrimidines, substituted pyridazines, substituted quinolines, substituted isoquinolines, Substituted quinoxaline, substituted quinazoline, substituted carbazole, substituted benzoimidazole, substituted benzofuran, substituted benzothiophene, substituted isobenzothiophene, substituted benzoxazole, substituted iso At least one substituent of the benzooxazole, the substituted triazole, the substituted oxadiazole, the substituted triazine, the substituted dibenzofuran and the substituted dibenzothiophene,

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

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

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

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A C ₁ -C ₆ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 411) (Q} 412), -Si (Q 413) (Q 414) (Q 415) and - _{B (Q 416) (Q 417} ) of the at least one substituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group , C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ Interrogating an aryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic group, fused polycyclic; And

Q ₄₂₁ , Q ₄₂₂ , Q ₄₂₃ , Q ₄₂₄ , Q ₄₂₅ , and -B Q ₄₂₆ , Q ₄₂₇ ; ;

L ₄₀₁ is an organic ligand;

xc1 is 1, 2 or 3;

xc2 is 0, 1, 2 or 3;

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

The L ₄₀₁ may be any monovalent, divalent or trivalent organic ligand. For example, L ₄₀₁ may be a halogen ligand (e.g. Cl, F), a diketone ligand (e.g., acetylacetonate, 1,3-diphenyl-l, 3- propanedionate, 6,6-tetramethyl-3,5-heptanedionate, hexafluoroacetonate), carboxylic acid ligands (e.g., picolinate, dimethyl-3-pyrazolecarboxylate, benzoate), carbon But are not limited to, monooxide ligands, isonitrile ligands, cyano ligands, and phosphorus ligands (e.g., phosphine, phosphaite).

If the formula of A 401 ₄₀₁ is to have two or more substituents, bonded to each other at least two substituents of A ₄₀₁ can form a saturated or unsaturated ring.

If the formula of A 401 ₄₀₂ is to have two or more substituents, bonded to each other at least two substituents of A ₄₀₂ can form a saturated or unsaturated ring.

는 서로 동일하거나 상이할 수 있다. 상기 화학식 401 중 xc1이 2 이상일 경우, A₄₀₁ 및 A₄₀₂는 각각 이웃하는 다른 리간드의 A₄₀₁ 및 A₄₀₂와 각각 직접(directly) 또는 연결기(예를 들면, C₁-C₅알킬렌기, C₂-C₅알케닐렌기, -N(R')-(여기서, R'은 C₁-C₁₀알킬기 또는 C₆-C₂₀아릴기임) 또는 -C(=O)-)를 사이에 두고 연결될 수 있다.When xc1 in Formula 401 is 2 or more, a plurality of ligands of Formula 401

May be the same or different from each other. If the formula xc1 401 is 2 or more of, A ₄₀₁ and A ₄₀₂ may be, for each of the other ligands neighboring A and ₄₀₁ respectively direct and A ₄₀₂ (directly) or linking group (e.g., C ₁ -C ₅ alkylene group, C ₂ -C ₅ alkenylene, -N (R ') - (wherein, R' - can be connected across a) is C ₁ -C ₁₀ alkyl or C ₆ -C ₂₀ aryl group), or -C (= O) have.

The phosphorescent dopant may include, but is not limited to, at least one of the following compounds PD1 to PD74:

Alternatively, the phosphorescent dopant may comprise the following PtOEP:

The fluorescent dopant may include DPAVBi, BDAVBi, TBPe, DCM, DCJTB, Coumarin 6 or C545T.

Alternatively, the fluorescent dopant may include a compound represented by the following formula (501):

<Formula 501>

In the above formula (501)

Ar ₅₀₁ is a naphthalene, heptalene, fluorenene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene ), Fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, And indenoanthracene;

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

The descriptions of L ₅₀₁ to L ₅₀₃ refer to the description of L ₂₀₁ in the present specification, respectively;

R ₅₀₁ and R ₅₀₂ independently represent a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, A benzyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, A dibenzothiophenyl group; And

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

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

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

The fluorescent dopant may comprise at least one of the following compounds FD1 to FD8:

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

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

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

The electron transport region may include at least one of a hole blocking layer, an electron transport layer (ETL), and an electron injection layer, but is not limited thereto.

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

The electron transporting region may include a hole blocking layer. The hole blocking layer may be formed to prevent the triplet excitons or holes from diffusing into the electron transporting layer when the light emitting layer is a phosphorescent dopant.

When the electron transporting region includes a hole blocking layer, a vacuum evaporation method, a spin coating method, a casting method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal imaging (LITI) The hole blocking layer may be formed on the light emitting layer. When the hole blocking layer is formed by the vacuum deposition method and the spin coating method, the deposition condition and the coating condition of the hole blocking layer refer to the deposition condition and the coating condition of the hole injection layer.

The hole blocking layer may include, for example, at least one of the following BCP and Bphen, but is not limited thereto.

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

The electron transporting region may include an electron transporting layer. The electron transport layer may be formed using various methods such as vacuum deposition, spin coating, casting, LB method, inkjet printing, laser printing, and laser induced thermal imaging (LITI) And may be formed on the light emitting layer or on the hole blocking layer. When the electron transport layer is formed by the vacuum deposition method and the spin coating method, the deposition conditions and the coating conditions of the electron transport layer refer to the deposition conditions and coating conditions of the hole injection layer.

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

Alternatively, the electron transporting layer may include at least one of the compounds represented by the following formula (601):

<Formula 601>

Ar ₆₀₁ - [(L ₆₀₁ ) _{xe 1} -E ₆₀₁ ] _{xe 2}

In the above formula (601), Ar ₆₀₁ is at least one selected from the group consisting of naphthalene, heptalene, fluorenene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene An anthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, a naphthacene, a picene, a perylene, Pentaphene and indenoanthracene;

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A C ₁ -C ₆ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic group and the condensed polycyclic _{-Si (Q 301) (Q 302} ) (Q 303) ( Q ₃₀₁ to Q ₃₀₃ are the independently from each other, hydrogen , A C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₆ -C ₆₀ aryl group and a C ₁ -C ₆₀ heteroaryl group), naphthalene, heptalene, fluorene, Spiro-fluorene, Ben Fluorene, dibenzo fluorene, page nalren, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, Cry Sen, naphthacene, pisen, perylene, penta pen and indeno anthracene; ;

For a description of L ₆₀₁ , see the discussion of L ₂₀₁ herein;

E ₆₀₁ is a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, An isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, an imidazolinyl group, A phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzopyranyl group, A benzofuranyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and dibenzocarbazolyl group; And

A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, salts, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a pen Frontale group, an indenyl group, a naphthyl group, an azulenyl group, a heptyl group Frontale, indazol hexenyl group, an acetoxy-naphthyl group, a fluorenyl group, a spy A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a klychenyl group, a naphthacenyl group, a phenanthryl group, a phenanthryl group, A thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, An isothiazolyl 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, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, A phenanthrolinyl group, a phenanthryl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzothiazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzothiazolyl group, Substituted with at least one of a halogen atom, an azo group, an iso-benzooxazole group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, An isoindolyl group, an indolyl group , An indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, A benzothiophene group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, a thiazolyl group, a thiazolyl group, an imidazolyl group, An oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group; ;

xe1 is selected from 0, 1, 2 and 3;

xe2 is selected from 1, 2, 3 and 4.

Alternatively, the electron transporting layer may include at least one of compounds represented by the following formula (602):

<Formula 602>

In the above formula (602)

₆₁₁ X is N or _{C- (L 611) xe611 -R 611} , X 612 is N or _{C- (L 612) xe612 -R 612} , X 613 is N or C- (L _{613) xe613} -R _613, and , At least one of X ₆₁₁ to X ₆₁₃ is N;

For a description of each of L ₆₁₁ to L ₆₁₆ , refer to the description of L ₂₀₁ in this specification;

R ₆₁₁ to R ₆₁₆ independently represent a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, A cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, a cyclohexyl group, And

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

xe611 to xe616 are independently selected from 0, 1, 2 and 3;

The compound represented by Formula 601 and the compound represented by Formula 602 may include at least one of the following compounds ET1 to ET15.

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 include an electron injection layer that facilitates electron injection from the second electrode 190.

The electron injecting layer may be formed using various methods such as vacuum deposition, spin coating, casting, LB method, inkjet printing, laser printing, and laser induced thermal imaging (LITI) , And on the electron transport layer. When the electron injection layer is formed by the vacuum deposition method and the spin coating method, the deposition conditions and the coating conditions of the electron injection layer refer to the deposition conditions and the coating conditions of the hole injection layer.

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

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

The second electrode 190 is disposed on the organic layer 150 as described above. The second electrode 190 may be a cathode, which is an electron injection electrode. At this time, the material for the second electrode 190 may be a metal, an alloy, an electrically conductive compound having a low work function, Can be used. Specific examples of the material for the second electrode 190 include Li, Mg, Al, Al-Li, Ca, Mg-In, , Magnesium-silver (Mg-Ag), and the like. Alternatively, ITO or IZO may be used as the material for the second electrode 190. The second electrode 190 may be a reflective electrode, a transflective electrode, or a transmissive electrode.

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

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

The C ₁ -C ₆₀ alkoxy group in the present specification 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 methoxy group, ethoxy group , Isopropyloxy group, and the like.

In the present specification, the C ₂ -C ₆₀ alkenyl group means a hydrocarbon group having at least one carbon double bond at the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethenyl group, a propenyl group, a butenyl group And the like. 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 means a hydrocarbon group containing one or more carbon triple bonds at the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include ethynyl group, Propynyl group 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, a cyclo Heptyl 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, the C ₁ -C ₁₀ heterocycloalkyl group means a monovalent monocyclic group having 1 to 10 carbon atoms including at least one hetero atom selected from N, O, P and S as a ring-forming atom, Specific examples include tetrahydrofuranyl group, 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 is a monovalent monocyclic group having 3 to 10 carbon atoms, which has at least one double bond in the ring, but does not have aromatics, Examples include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group and the like. In the present specification, the C ₃ -C ₁₀ cycloalkenylene group means a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkenyl group.

In the present specification, the C ₁ -C ₁₀ heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms including at least one hetero atom selected from N, O, P and S as a ring-forming atom, It has one double bond. Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl include a 2,3-hyrofuranyl group, a 2,3-hydrothiophenyl group, and the like. In the present specification, the C ₁ -C ₁₀ heterocycloalkenylene group means a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkenyl group.

In the present specification, a C ₆ -C ₆₀ aryl group means a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and a C ₆ -C ₆₀ arylene group means a carbamoyl group having 6 to 60 carbon atoms Quot; means a divalent group having a cyclic aromatic system. Specific examples of the C ₆ -C ₆₀ aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a klycenyl group and the like. The C ₆ -C ₆₀ aryl groups and C ₆ -C ₆₀ arylene If the group contains two or more rings, the 2 or more rings may be fused to each other.

As used herein, a C ₁ -C ₆₀ heteroaryl group means a monovalent group having at least one heteroatom selected from N, O, P and S as a ring-forming atom and having a carbocyclic aromatic system having from 1 to 60 carbon atoms And a C ₁ -C ₆₀ heteroarylene group means a divalent group having at least one heteroatom selected from N, O, P and S as a ring-forming atom and having a carbocyclic aromatic system having 1 to 60 carbon atoms do. Specific examples of the C ₁ -C ₆₀ heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group and the like. When the C ₁ -C ₆₀ heteroaryl group and the C ₁ -C ₆₀ heteroarylene group include two or more rings, two or more rings may be fused together.

The specification of the C ₆ -C ₆₀ aryloxy group -OA group -SA _{102 103} points to a (where A ₁₀₂ is the C ₆ -C ₆₀ aryl group), a C ₆ -C ₆₀ arylthio (arylthio) (wherein, And A ₁₀₃ is the above C ₆ -C ₆₀ aryl group.

In the present specification, a monovalent non-aromatic condensed polycyclic group is a monovalent aromatic condensed polycyclic group in which two or more rings are condensed with each other and contain only carbon as a ring-forming atom and the whole molecule is non-aromatic. &Lt; / RTI &gt; Examples of the monovalent non-aromatic condensed polycyclic group include fluorenyl and the like. In the present specification, the divalent non-aromatic condensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

In the present specification, a monovalent non-aromatic condensed heteropolycyclic group is a monovalent aromatic condensed heteropolycyclic group in which two or more rings are condensed with each other and contain heteroatoms selected from N, O, P and S in addition to carbon as a ring- , And mono-valent groups in which the whole molecule has non-aromacity. The monovalent non-aromatic heterocyclic polycyclic group includes carbazolyl 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, "Ph" means phenyl, "Me" means methyl, "Et" means ethyl, and "ter-Bu" or "Bu ^t " means tert-butyl.

Hereinafter, the organic light-emitting device according to one embodiment of the present invention will be described in more detail with reference to synthesis examples and examples. In the following Synthesis Examples, the molar equivalent of A and the molar equivalent of B in the expression "B was used instead of A"

 [Example]

Synthetic example  1: Synthesis of Compound (9)

Synthesis of intermediate 9-1

5.2 g (23.6 mmol) of 2-bromo-5-chloroanisole are dissolved in 100 ml of THF, and 10 ml of n-BuLi (25.0 mmol, 2.5 M in Hexane) is slowly added dropwise at -78 ° C. After stirring at the same temperature for 1 hour, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2-isoproxy- 9.3 mL (50.0 mmol) of tetramethyl-1,3,2-dioxaborolane was slowly added dropwise, and the reaction solution was stirred at -78 ° C for 1 hour and then at room temperature for additional 24 hours. After the reaction was completed, 50 mL of 10% HCl aqueous solution and 50 mL of H ₂ O were added and extracted three times with 80 mL of diethyl ether. The combined organic layer was dried over magnesium sulfate and the solvent was evaporated. The obtained residue was separated and purified by silica gel column chromatography to obtain 5.83 g (yield 92%) of intermediate 9-1. The resulting compound was identified via LC-MS.

C ₁₃ H ₁₈ BClO ₃ : M ⁺ 268.1

Synthesis of intermediate 9-2

Intermediate 9-1 5.90g (22.0 mmol), 1,4- di-bromo Mock license 16.9g (44.0 mmol), Pd ( PPh 3) 4 ( tetrakis (triphenylphosphine) palladium) 1.27g (1.1 mmol) and 4.50 g (33 mmol) of K ₂ CO ₃ was dissolved in 200 ml of a mixed solution of THF / H ₂ O (2/1 by volume), followed by stirring at 70 ° C for 5 hours. After the reaction solution was cooled to room temperature, 60 ml of water was added and extracted three times with 60 ml of ethyl ether. The combined organic layer was dried over magnesium sulfate and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography to obtain 6.30 g (yield: 64%) of intermediate 9-2. The resulting compound was identified via LC-MS.

C ₂₅ H ₁₆ BrClO: M ⁺ 446.0

Synthesis of intermediate 9-3

Intermediate 9-2 8.92 g (20.0 mmol), intermediate 9-A 9.65 g (40.0 mmol ), Pd 2 (dba) 3 0.37 g (0.4 mmol), P (t -Bu) 3 0.08 g (0.4 mmol) and t -BuOK 5.76 g (60.0 mmol) was dissolved in 90 ml of toluene, and the mixture was stirred at 85 ° C for 12 hours. The reaction mixture was cooled to room temperature, and extracted three times with 50 mL of water and 50 mL of diethyl ether. The combined organic layer was dried over magnesium sulfate and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography to obtain 13.5 g (83% yield) of intermediate 9-3. The resulting compound was identified via LC-MS.

C ₅₅ H ₅₂ N ₂ OSi ₂ M ⁺ 812.4

Synthesis of Intermediate 9-4

1.62 g (2.00 mmol) of Intermediate 9-3 is dissolved in 10 ml of dichloromethane, and then 0.33 ml (3.5 mmol) of BBr ₃ is slowly added dropwise at -78 ° C. The reaction solution was warmed to room temperature and stirred at room temperature for 24 hours. After the reaction was complete, 5 mL of MeOH and 10 mL of H ₂ O were added and extracted three times with 10 mL of dichloromethane. The combined organic layer was dried over magnesium sulfate and the solvent was evaporated. The obtained residue was separated and purified by silica gel column chromatography to obtain 1.20 g (yield 75%) of intermediate 9-4. The resulting compound was identified via LC-MS.

C ₅₄ H ₅₀ N ₂ OSi ₂ : M ⁺ 798.3

Synthesis of Compound 9

Intermediate 9-4 1.60 g (2.00 mmol) is dissolved in DMF (10 ml), and then 0.48 g (6.0 mmol) of CuO is added dropwise at room temperature. The reaction solution was stirred at 140 占 폚 for 48 hours. After the reaction was completed, the reaction mixture was filtered through celite, and 10 mL of H ₂ O was added to the collected organic layer, followed by extraction three times with 10 mL of ethyl acetate. The combined organic layer was dried over magnesium sulfate and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography to obtain 1.39 g (yield 87%) of Compound 9. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

[delta] = 8.60-8.58 (m, IH), 8.31-8.29 (m, IH), 8.20-8.18 (m, IH), 7.96-7.94 (m, IH), 7.84-7.74 (m, 4H), 6.74-6.70 (m, 3H), 6.65-6.60 (m, 2H) , 6.51-6.45 (m, 2H), 0.24 (s, 18H)

C ₅₄ H ₄₈ N ₂ OSi ₂ : M ⁺ calc. 796.33 found 796.34

Synthesis Example 2: Synthesis of Compound 1

Compound 1 was synthesized in the same manner as in the synthesis of Compound 9, except that Intermediate 1-A was used instead of Intermediate 9-A. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

1H), 7.63-7.48 (m, 5H), 7.12-7.02 (m, 9H), 8.09 (d, ), 6.76-6.74 (m, IH), 6.66-6.61 (m, 4H), 6.50 (dd,

M ⁺ calc. 652.25 found 652.26

Synthesis Example 3: Synthesis of Compound 3

Compound 3 was synthesized in the same manner as in the synthesis of Compound 9, except that Intermediate 3-A was used instead of Intermediate 9-A. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

(m, 2H), 7.97-7.85 (m, 1H), 7.82-7.79 (m, 1H), 8.51-8.47 2H), 7.16-7.01 (m, 6H), 6.85-6.77 (m, 4H), 6.66 (dd, 1H), 6.52-6.49 (m, 2 H), 6.45 - 6.41 (m, 2 H)

M ⁺ calc. 852.31 found 852.32

Synthesis Example 4: Synthesis of Compound 8

Compound 8 was synthesized in the same manner as in the synthesis of Compound 9, except that Intermediate 8-A was used instead of Intermediate 9-A. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

2H), 7.84-7.79 (m, 2H), 7.72-7.67 (m, IH) (m, 3H), 7.63-7.54 (m, 5H), 7.48-7.40 (m, 4H), 7.32-7.30 , 6.71 (dd, 1 H)

M ⁺ calc. 842.34 found 842.34

Synthesis Example 5: Synthesis of Compound 11

Compound 11 was synthesized in the same manner as in the synthesis of Compound 9, except that Intermediate 11-A was used instead of Intermediate 9-A. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

1H), 7.84-7.79 (m, 2H), 7.72-7.68 (m, IH) (m, 3H), 7.63-7.54 (m, 6H), 7.48-7.40 (m, 4H), 7.32-7.14 (m, 9H), 6.92-6.90 , 6.72 (dd, 1H), 6.56-6.53 (m, 2H), 6.53-6.50 (m, 2H)

C ₆₀ H ₃₆ N ₂ O ₃ : M ⁺ calc. 832.27 found 832.28

Synthesis Example 6: Synthesis of Compound 14

Compound 14 was synthesized in the same manner as in the synthesis of Compound 9, except that Intermediate 14-A was used instead of Intermediate 9-A. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

[delta] = 8.60-8.58 (m, IH), 8.31-8.29 (m, IH), 8.20-8.18 (m, IH), 7.92-7.88 (m, 3H), 7.84-7.70 (m, 4H), 7.34-7.22 (m, 7H), 6.93-6.88 (m, 2H), 6.80-6.78 -6.42 (m, 2 H)

M ⁺ calc. 992.36 found 992.37

Synthesis Example 7: Synthesis of Compound 18

Compound 18 was synthesized in the same manner as in the synthesis of Compound 9, except that Intermediate 18-A was used instead of Intermediate 9-A. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

2H), 7.94-7.89 (m, 1H), 7.72-7.65 (m, 2H), 8.30-8.28 (m, 4H), 7.55-7.50 (m, 2H), 7.38-7.30 (m, 5H), 7.25-7.20 (m, 2H), 7.08-7.05 , 6.89-6.81 (m, 4H), 6.76 (dd, 1H), 6.67-6.63 (m, 2H)

M ⁺ calc. 654.24 found

Synthesis Example 8: Synthesis of Compound 21

Compound 21 was synthesized in the same manner as in the synthesis of Compound 9, except that Intermediate 21-A was used instead of Intermediate 9-A. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

[delta] = 8.60-8.58 (m, IH), 8.30-8.26 (m, 2H), 8.20-8.18 (m, IH), 7.82-7.76 (m, 3H), 7.68-7.54 (m, 6H), 7.41-7.30 (m, 6H), 7.22-7.16 (m, 5H), 6.99 (md, 1H), 6.92-6.86 , 18H)

M ⁺ calc. 1028.46 found 1028.46

Synthesis Example 9: Synthesis of Compound 23

Compound 23 was synthesized in the same manner as in the synthesis of Compound 9, except that Intermediate 23-A was used instead of Intermediate 9-A. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

1H), 7.84-7.80 (m, 2H), 7.72-7.66 (m, IH), 8.41-8.28 (m, 3H), 6.93-7.54 (m, 6H), 7.48-7.34 (m, 8H), 7.21 (dd, -6.70 (m, 3H), 0.24 (m, 18H)

M ⁺ calc. 976.35 found 976.36

Synthesis Example 10: Synthesis of Compound 26

Compound 26 was synthesized in the same manner as in the synthesis of Compound 9, except that Intermediate 26-A was used instead of Intermediate 9-A. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

2H), 7.73-7.70 (m, 4H), 7.64-7.40 (m, IH) (m, 2H), 7.32-7.20 (m, 5H), 7.11-7.06 (m, 2H), 6.87-6.81 (m, 3H), 6.73-6.70

M ⁺ calc. 984.34 found 984.35

Synthesis Example 11: Synthesis of Compound 31

Compound 31 was synthesized by the same method as in the synthesis of Compound 9, except that Intermediate 9-A was used instead of Intermediate 9-A, and Intermediate 11-A was used first, followed by Intermediate 31-A. Respectively. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

(m, IH), 7.73-7.71 (m, IH), 7.30-7.28 (m, 1H), 7.63-7.40 (m, 13H), 7.21-6.94 (m, 10H), 6.82-6.80 -6.35 (m, 4 H)

C ₆₀ H ₃₈ N ₂ O ₂ : M ⁺ calc. 818.29 found 818.30

Synthesis Example 12: Synthesis of Compound 32

Compound 32 was synthesized in the same manner as in the synthesis of Compound 9, except that Intermediate 9-A was replaced with Intermediate 32-A first, and Intermediate 31-A was next used in the synthesis of Intermediate 9-3. Respectively. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

2H), 7.66-7.40 (m, 20H), 7.21-6.96 (m, IH) 2H), 6.40-6.36 (m, 2H), 6.92-6.60 (m, 3H)

C ₆₆ H ₄₃ FN ₂ O: M ⁺ calc. 898.34 found 898.35

Synthesis Example 13: Synthesis of Compound 35

Compound 35 was synthesized in the same manner as in the synthesis of Compound 9 except that Intermediate 9-A was used instead of Intermediate 9-A, and Intermediate 9-A was used first, followed by Intermediate 9-A. Respectively. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

(m, IH), 7.72-7.70 (m, IH), 7.20-8.18 (m, 1H), 7.63-7.52 (m, 6H), 7.48-7.36 (m, 4H), 7.21-7.14 , 6.73 (dd, 1H), 6.67-6.62 (m, 2H), 6.53-6.50 (m, 2H), 0.24

M ⁺ calc. 814.30 found 814.31

Synthesis Example 14: Synthesis of Compound 38

Compound 38 was synthesized in the same manner as in the synthesis of Compound 9, except that Intermediate 9-A was used instead of Intermediate 9-A, and Intermediate 9-A was used first, followed by Intermediate 38-A. Respectively. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

(m, 2H), 7.82-7.80 (m, IH), 8.30-8.28 (m, 1H), 7.72-7.70 (m, 1H), 7.65-7.40 (m, 9H), 7.40-7.36 (m, 2H), 7.22-7.13 , 6.91-6.81 (m, 4H), 6.73 (m, 2H), 6.54-6.54

M ⁺ calc. 824.32 found 824.33

Synthesis Example 15: Synthesis of Compound 48

Compound 48 was synthesized in the same manner as in the synthesis of Intermediate 9-3 except that Intermediate 48-A was used instead of Intermediate 9-A, and then Intermediate 11-A was used. Respectively. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

1H), 7.72-7.53 (m, 1H), 7.48-7.40 (m, 1H) (m, 4H), 7.28-7.04 (m, IH), 6.96-6.94 (m, IH), 6.82-6.80 (m, IH), 6.75-6.70 -6.44 (m, 2 H), 6.27 - 6.25 (m, 2 H)

M ⁺ calc. 818.29 found 818.30

Synthesis Example 16: Synthesis of Compound 49

Compound 49 was synthesized in the same manner as in the synthesis of Compound 9, except that Intermediate 9-A was used instead of Intermediate 9-A, and Intermediate 14-A was used first, followed by Intermediate 11-A. Respectively. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

1H), 7.70-7.40 (m, 21H), 7.22-7.04 (m, &lt; RTI ID = (m, 2H), 6.92-6.90 (m, 2H), 6.85-6.78 (m, 2H)

M ⁺ calc. 912.32 found 912.33

Synthesis Example 17: Synthesis of Compound 50

Compound 50 was synthesized in the same manner as in the synthesis of Compound 9 except that Intermediate 9-A was replaced with Intermediate 50-A first, and then Intermediate 11-A was used instead of Intermediate 9-A in Synthesis of Intermediate 9-3. Respectively. The resulting compound was identified by &lt; 1 &gt; H NMR (CDCl3, 400 MHz) and MS / FAB.

3H), 7.72-7.67 (m, 3H), 7.61-7.54 (m, IH), 8.42-8. (d, IH), 6.66-6.63 (m, IH), 7.49-7.40 (m, 5H), 7.29-7.00 (m, 2H)

M ⁺ calc. 908.30 found 908.31

Synthesis Example 18: Synthesis of Compound 57

Synthesis of Intermediate 9-3 Compound 57 was synthesized in the same manner as in the synthesis of Compound 9, except that Intermediate 1-A was used in place of Intermediate 9-A, and then Intermediate 50-A was used next. Respectively. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

2H), 7.72-7.70 (m, 3H), 7.63-7.54 (m, IH), 8.30-8.28 (m, 2H), 6.74-6.72 (m, 1H), 6.61 (t, 1H), 6.52 (m, 1H), 7.49-7.40 -6.48 (m, 2 H)

M ⁺ calc. 818.29 found 818.30

Synthesis Example 19: Synthesis of Compound 60

Compound 60 was synthesized in the same manner as in the synthesis of Compound 9 except that Intermediate 9-A was replaced with Intermediate 48-A first, and then Intermediate 50-A was used in the synthesis of Intermediate 9-3. Respectively. The resulting compound was identified by &lt; 1 &gt; H NMR (CDCl3, 400 MHz) and MS / FAB.

1H), 7.72-7.70 (m, 1H), 7.65-7.50 (m, 1H), 8.43-8.28 (m, 1H), 6.72 (t, 1H), 6.64 (m, 1H), 7.47-7.40 1H), 6.41 (dd, 1H), 6.34-6.32 (m, 2H)

M ⁺ calc. 894.32 found 894.33

Synthesis Example 20: Synthesis of Compound 63

Compound 63 was synthesized in the same manner as in the synthesis of Intermediate 9-3 except that Intermediate 38-A was used instead of Intermediate 9-A, and then Intermediate 50-A was used. Respectively. The resulting compound was confirmed by _{1H NMR (CDCl 3, 400 MHz} ) and MS / FAB.

(m, 2H), 7.84-7.76 (m, IH), 8.30-8.28 (m, 2H), 7.72-7.69 (m, 2H), 7.65-7.40 (m, 17H), 7.30-7.02 (m, 9H), 6.91-6.89 (M, 2H), 6.40-6.38 (m, 1H), 6.35 (dd, 1H)

M ⁺ calc. 918.32 found 918.33

Synthesis Example 21: Synthesis of Compound 70

Compound 70 was synthesized in the same manner as in the synthesis of Compound 9, except that Intermediate 9-A was replaced with Intermediate 14-A first, and then Intermediate 1-A was used in the synthesis of Intermediate 9-3. Respectively. The resulting compound was confirmed by _{1H NMR (CDCl 3, 400 MHz} ) and MS / FAB.

(m, 1H), 7.32-7.22 (m, 1H), 8.22-8.20 (m, (m, 2H), 7.16-7.14 (m, 1H), 7.06-6.98 (m, 3H), 6.82-6.80

M ⁺ calc. 822.30 found 822.31

Synthesis Example 22: Synthesis of Compound 73

In the same manner as in the synthesis of Intermediate 9-3 in Synthesis Example 1 except that Intermediate 32-A was used first and Intermediate 73-A was used in place of Intermediate 9-A, Compound 73 was synthesized. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

(m, 1H), 7.31-7.29 (m, IH), 7.20-8.18 (m, 2H), 7.22-7.20 (m, 6H), 7.13-7.08 (m, 2H), 6.96-6.94 -6.58 (m, 2 H), 2.25 (s, 6 H)

C ₆₃ H ₄₂ FN ₃ O: M ⁺ calc. 875.33 found 875.34

Synthesis Example 23: Synthesis of Compound 75

The same method as in the synthesis of Compound 9 was performed except that Intermediate 48-A was used first in place of Intermediate 9-A in the synthesis of Intermediate 9-3 in Synthesis Example 1, and Intermediate 75-A was used in the next place Compound 75 was synthesized. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

1H), 7.68-7. 62 (m, 1H), 7.68-7.52 (m, 10H), 7.47-7.44 (m, 1H), 8.33-8.30 (m, 2H), 7.35-7.30 (m, 1H), 7.19-6.98 (m, 10H), 6.87-6.84 (m, 2H), 6.72-6.60 , 6.44-6.41 (m, 2H), 6.35-6.30 (m, 2H), 1.61 (s, 6H)

M ⁺ calc. 843.35 found 843.35

Synthesis Example 24: Synthesis of Compound 77

The same procedure as in the synthesis of the compound 9 was carried out except that Intermediate 9-A was used in place of Intermediate 9-A in Synthesis Example 1 of Synthesis Example 1, and Intermediate 75-A was used in the next place To thereby synthesize Compound 77. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

1H), 7.84-7.54 (m, 10H), 7.45-7.40 (m, IH) (m, 2H), 7.35-7.30 (m, 1H), 7.24-7.04 (m, 9H), 6.97 (dd, 2H), 6.63-6.41 (m, 2H), 6.33-6.30 (m, 2H), 1.63 (s, 6H)

M ⁺ calc. 858.32 found 858.33

Synthesis Example 25: Synthesis of Compound 79

The same method as that for the synthesis of the compound 9 was performed except that Intermediate 79-A was used in place of Intermediate 9-A, and Intermediate 75-A was used in the synthesis of Intermediate 9-3 in Synthesis Example 1 To synthesize Compound 79. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

2H), 7.65 (dd, IH), 7.63-7.54 (m, IH), 7.30-8. (M, 2H), 7.15-7.02 (m, 7H), 6.86 (dd, (m, 2H), 6.53-6.50 (m, 2H), 6.46-6.42 (m, 2H), 6.33-6.31 (s, 9 H)

M ⁺ calc. 824.38 found 824.39

Synthesis Example 26: Synthesis of Compound 84

Synthesis of Intermediate 9-3 in Synthesis Example 1 was repeated except that Intermediate 11-A was used in place of Intermediate 9-A, and Intermediate 84-A was used in the next place. Compound 84 was synthesized. The resulting compound was confirmed by _{1H NMR (CDCl 3, 400 MHz} ) and MS / FAB.

1H), 7.94-7.92 (m, IH), 7.84-7.82 (m, IH), 8.31-8.29 (m, 2H), 7.16-6.94 (m, 7H), 6.81-6.75 (m, 2H), 7.72-7.70 , 6.63-6.57 (m, 2H), 6.49-6.47 (m, IH), 6.43-6.40 (m, 2H)

M ⁺ calc. 819.29 found 819.30

Synthesis Example 27: Synthesis of Compound 86

Synthesis of Intermediate 86-1

Synthesis of intermediate 9-2 was carried out in the same manner as in the synthesis of intermediate 9-2 except that intermediate 86-A was used instead of intermediate 9-1 and intermediate 9-2 was used instead of dibromonaphthalene in the synthesis of intermediate 9-2 in Synthesis Example 1 To obtain Intermediate 86-1. The resulting compound was identified via LC-MS.

C ₄₃ H ₃₀ ClNO: M ⁺ 611.2

Synthesis of Intermediate 86-2

In the synthesis of Intermediate 9-3 in Synthesis Example 1, except that Intermediate 86-1 was used instead of 1-A and Intermediate 9-2 instead of Compound 9-A, the same method as Synthesis of Intermediate 9-3 was used Intermediate 86-2 was synthesized. The resulting compound was identified via LC-MS.

C ₅₅ H ₄₀ N ₂ O: M ⁺ 744.3

Synthesis of Intermediate 86-3

Intermediate 86-3 was synthesized in the same manner as in the synthesis of Intermediate 9-4 except that Intermediate 86-2 was used instead of Intermediate 9-3 in Synthesis Example 9-4 of Synthesis Example 1 . The resulting compound was identified via LC-MS.

C ₅₄ H ₃₈ N ₂ O: M ⁺ 730.3

Synthesis of Compound 86

Compound 86 was synthesized in the same manner as in the synthesis of Compound 9, except that Intermediate 86-3 was used instead of Intermediate 9-4 in Synthesis Example 9 of Synthesis Example 1. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

1H), 7.79-7.77 (m, 1H), 7.67-7.27 (m, 1H) 2H), 7.56-7.49 (m, 2H), 7.18-7.03 (m, 10H), 6.96-6.93 (m, 2H), 6.86-6.84 ), 6.62-6.59 (m, 1H), 6.50-6.47 (m, 4H), 6.36-6.32 (m, 4H)

C ₅₄ H ₃₆ N ₂ O: M ⁺ calc. 728.28 found 728.29

Synthesis Example 28: Synthesis of Compound 92

Compound 92 was synthesized in the same manner as in the synthesis of Compound 86 except that Intermediate 11-A was used in place of Intermediate 1-A in the synthesis of Intermediate 86-2 in Synthesis Example 27. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

1H), 7.84-7.77 (m, 2H), 7.72-7.62 (m, IH), 8.39-8. (m, 4H), 7.53-7.40 (m, 5H), 7.28-7.13 (m, 12H), 6.92-6.90 , 6.56 - 6.52 (m, 2H), 6.40 - 6.35 (m, 4H)

M ⁺ calc. 818.29 found 818.30

Synthesis Example 29: Synthesis of Compound 94

Using Intermediate 86 instead of Intermediate A-94-A, and except that using 11-A instead of Intermediate 1-A, using the same method for the synthesis of compound 86 was synthesized from compound 94. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

1H), 7.84-7.79 (m, 2H), 7.72-7.40 (m, IH), 8.39-8. 2H), 6.69 (d, 1H), 6.56-6.54 (m, 2H), 6.39 (m, 1H), 7.30-7.02 -6.37 (m, 2 H)

M ⁺ calc. 894.32 found

Synthesis Example 30: Synthesis of Compound 98

Compound 98 was synthesized in the same manner as in the synthesis of Compound 86 except that Intermediate 98-A was used in place of Intermediate 86-A. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

1H), 7.79-7.77 (m, 1H), 7.72-7.50 (m, 1H), 8.24-8.22 (m, 1H), 7.44-7.42 (m, 1H), 7.28-7.14 (m, 9H), 7.10-7.05 (m, 2H), 6.97-6.95 , 6.72 (dd, 1H), 6.50-6.45 (m, 4H), 6.40-6.41 (m, 2H)

M ⁺ calc. 898.34 found 898.35

Synthesis Example 31: Synthesis of Compound 103

Compound 103 was synthesized in the same manner as in the synthesis of Compound 86, except that Intermediate 1-A was replaced by Intermediate 50-A. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

1H), 7.84-7.79 (m, 2H), 7.72-7.40 (m, IH), 8.39-8. (m, 14H), 7.30-7.02 (m, 14H), 6.88-7.82 (m, 2H), 6.74-6.72

M ⁺ calc. 894.32 found 894.33

Synthesis Example 32: Synthesis of Compound 107

Compound 107 was synthesized in the same manner as in the synthesis of compound 86 except that Intermediate 107-A was used instead of Intermediate 86-A. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

1H), 7.79-7.77 (m, 1H), 7.67-7.56 (m, 1H), 8.16-8.14 (m, 3H), 7.53-7.49 (m, 2H), 7.40-7.36 (m, 2H), 7.29-7. 13 (m, 7H), 7.06-7.02 , 6.84-6. 75 (m, 4H), 6.66-6.59 (m, 3H), 6.40-6.34

M ⁺ calc. 800.32 found 800.33

Synthesis Example 33: Synthesis of Compound 113

Compound 113 was synthesized in the same manner as in the synthesis of Compound 86 except that Intermediate 113-A was used in place of Intermediate 86-A and Intermediate 31-A was used in place of Intermediate 1-A. _{^{1 H NMR (CDCl 3, 400}} MHz) , and were confirmed by MS / FAB.

1H), 7.79-7.77 (m, 1H), 7.67-7.44 (m, 1H), 8.16-8.14 (d, 1H), 6.58-6.54 (m, 2H), 6.50 (m, 1H), 7.31-7.09 -6.46 (m, 2H)

C ₅₄ H ₃₆ N ₂ O: M ⁺ calc. 880.35 found 880.36

Synthesis Example 34: Synthesis of Compound 121

Compound 121 was synthesized in the same manner as in the synthesis of Compound 86 except that Intermediate 121-A was used in place of Intermediate 86-A and Intermediate 121-B was used in place of Intermediate 1-A. _{^{1 H NMR (CDCl 3, 400}} MHz) , and were confirmed by MS / FAB.

1H), 7.79-7.77 (m, 1H), 7.67-7.58 (m, 1H), 8.16-8.14 (m, 3H), 7.53-7.49 (m, 2H), 7.38-7.30 (m, 2H), 7.17-7.13

M ⁺ calc. 748.31 found 748.31

Synthesis Example 35: Synthesis of Compound 124

Compound 124 was synthesized in the same manner as in the synthesis of Compound 86 except that Intermediate 124-A was used in place of Intermediate 86-A and Intermediate 17-A was used in place of Intermediate 1-A. _{^{1 H NMR (CDCl 3, 400}} MHz) , and were confirmed by MS / FAB.

1H), 8.24-8.22 (m, 1H), 8.16-8.14 (m, 1H), 7.84-7.40 (m, 11H), 7.28-7.08 (m, 2H), 6.25 (m, 1H), 6.90-6.88 (m, 2H), 2.28 (s, 3H), 2.26 (s, 6H)

M ⁺ calc. 860.34 found 860.35

Synthesis Example 36: Synthesis of Compound 141

Synthesis of intermediate 141-1

Intermediate 141-1 was synthesized in the same manner as Intermediate 9-3 except that Intermediate 9-A was used in place of Intermediate 9-A in Synthesis Example 1, except that Intermediate 35-A was used instead of Intermediate 9-A. The resulting compound was identified via LC-MS.

C ₄₂ H ₂₄ ClNO ₂ : M + 609.2

Synthesis of Intermediate 141-2

Synthesis of Intermediate 9-2 was carried out in the same manner as Intermediate 9-2 except that Intermediate 94-A was used instead of Intermediate 9-1 and Intermediate 141-1 was used instead of Dibromonaphthalene in Synthesis Example 1 To obtain Intermediate 141-2. The resulting compound was identified via LC-MS.

C67H46N2O2: M + 910.3

Synthesis of intermediate 141-3

Intermediate 141-3 was synthesized in the same manner as in the synthesis of Intermediate 9-4 except that Intermediate 141-2 was used instead of Intermediate 9-3 in Synthesis Example 9-4 of Synthesis Example 1 . The resulting compound was identified via LC-MS.

C 66 H 44 N ₂ O ₂ : M + 896.3

Synthesis of Compound 141

Compound 141 was synthesized in the same manner as in the synthesis of Compound 9, except that Intermediate 141-3 was used instead of Intermediate 9-4 in Synthesis Example 9 of Synthesis Example 1. The resulting compound was identified by &lt; 1 &gt; H NMR ( _CDCl3 , 400 MHz) and MS / FAB.

2H), 7.84-7.82 (m, IH), 7.72-7.70 (m, IH), 8.39-8. 2H), 7.16-7.04 (m, 8H), 6.95-6.92 (m, 1H), 6.85-6.80 (m, 2H), 7.63-7.26 2H), 6.63-6.62 (m, 2H), 6.53-6.49 (m, 2H), 6.37-6.34

M + calc. 894.32 found 894.33

Synthesis Example 37: Synthesis of Compound 154

Compound 154 was synthesized using the same method as the synthesis of compound 86, except that Intermediate 154-A was used instead of Intermediate 86-A. _{^{1 H NMR (CDCl 3, 400}} MHz) , and were confirmed by MS / FAB.

2H), 7.97-7.90 (m, 2H), 7.80-7.78 (m, IH), 8.24-8.22 (m, 1H), 6.97 (dd, 1H), 6.87-7.41 (m, 1H) (D, 1H), 6.50-6.42 (m, 8H), 6.85 (m,

M ⁺ calc. 818.29 found 818.30

Synthesis Example 38: Synthesis of Compound 156

Compound 156 was synthesized in the same manner as in the synthesis of compound 86 except that Intermediate 156-A was used in place of Intermediate 86-A. _{^{1 H NMR (CDCl 3, 400}} MHz) , and were confirmed by MS / FAB.

(m, 1H), 7.94-7.91 (m, 1H), 7.88 (d, 1H), 8.06-8.04 (M, 1H), 7.82-7.80 (m, 1H), 7.67-7.56 (m, 3H), 7.40-7.30 6.85 (m, 1H), 6.78-6.59 (m, 7H), 6.40-6.35 (m, 4H)

C ₅₃ H ₃₅ N ₃ O: M ⁺ calc. 729.28 found 729.29

Synthesis Example 39: Synthesis of Compound 157

Compound 157 was synthesized in the same manner as in the synthesis of compound 141 except that Intermediate 1-A was used in place of Intermediate 35-A and 157-A was used in place of Intermediate 94-A.

2H), 7.82-7.78 (m, 2H), 7.65-7.54 (m, IH), 7.30-7.28 (m, 2H), 7.35 (t, 1H), 7.26-7.19 (m, (m, 4 H), 6.52 - 6.46 (m, 4 H)

M ⁺ calc. 818.29 found 818.29

Synthesis Example 40: Synthesis of Compound 160

Synthesis of intermediate 9-2 was carried out in the same manner as in the synthesis of intermediate 9-2 except that in the synthesis of intermediate 9-2 in Synthesis Example 1, Intermediate 107-A was used instead of Intermediate 9-1, and Intermediate 9-2 was used instead of dibromonaphthalene To obtain intermediate 160-1. The resulting compound was identified via LC-MS.

C ₆₇ H ₆₀ N ₂ OSi ₂ : M ⁺ 964.4

Synthesis of intermediate 160-3

Intermediate 160-3 was synthesized in the same manner as in the synthesis of Intermediate 9-4 except that Intermediate 160-1 was used instead of Intermediate 9-3 in Synthesis Example 9-4 of Synthesis Example 1 . The resulting compound was identified via LC-MS.

C ₆₆ H ₅₈ N ₂ OSi ₂ : M ⁺ 950.4

Synthesis of Compound 160

Compound 160 was synthesized in the same manner as in the synthesis of Compound 9 except that Intermediate 160-3 was used in place of Intermediate 9-4 in Synthesis Example 9 of Synthesis Example 1. The resulting compound was identified by ¹ H NMR (CDCl ₃ , 400 MHz) and MS / FAB.

1H), 8.14-8.14 (m, 1H), 8.01-7.99 (m, 1H), 7.89-7.87 (m, 1H), 7.77-7.72 (m, 2H), 7.66-7.59 (m, 4H), 7.52-7.45 (m, 6H), 7.38-7.35 , 6.85-6.82 (m, 2H), 6.76-6.65 (m, 4H), 6.52-6.46 (m, 4H)

M ⁺ calc. 948.39 found 948.40

Example 1

An ITO glass substrate (manufactured by Corning) having a thickness of 1200 Å was cut into a size of 50 mm × 50 mm × 0.7 mm, ultrasonically washed with isopropyl alcohol and pure water for 5 minutes, irradiated with ultraviolet rays for 30 minutes, And the ITO glass substrate was placed in a vacuum deposition apparatus.

HT3 was deposited on the anode to form a hole injection layer having a thickness of 600 A and HT3 was deposited on the hole injection layer to form a hole transport layer having a thickness of 300 ANGSTROM. Then, ADN and the compound 9 were deposited on the hole transport layer 98: 2 to form a 300 Å thick light emitting layer.

Alq ₃ was deposited on the light emitting layer to form an electron transporting layer of 300 ANGSTROM. LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 A, and Al was vacuum deposited on the electron injection layer to form a cathode having a thickness of 3000 A to form an organic light emitting device.

Example 2

An organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 11 was used instead of Compound 9 in forming the light emitting layer.

Example 3

An organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 31 was used instead of Compound 9 in forming the light emitting layer.

Example 4

An organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 32 was used instead of Compound 9 in forming the light emitting layer.

Example 5

An organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 73 was used instead of Compound 9 in forming the light emitting layer.

Example 6

An organic light emitting device was fabricated in the same manner as in Example 1 except that the compound 86 was used instead of the compound 9 in forming the light emitting layer.

Example 7

An organic light emitting device was fabricated using the same method as in Example 1, except that Compound 113 was used instead of Compound 9 in forming the light emitting layer.

Example 8

An organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 156 was used instead of Compound 9 in forming the light emitting layer.

Comparative Example 1

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound A was used instead of Compound 9 in forming the light emitting layer.

<Compound A>

Comparative Example 2

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound B was used instead of Compound 9 in forming the light emitting layer.

<Compound B>

Example 9

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound H109 was used instead of ADN in forming the light emitting layer.

Example 10

An organic light emitting device was fabricated in the same manner as in Example 9 except that Compound 11 was used instead of Compound 9 in forming the light emitting layer.

Example 11

An organic light emitting device was fabricated in the same manner as in Example 9 except that Compound 31 was used instead of Compound 9 in forming the light emitting layer.

Example 12

An organic light emitting device was fabricated in the same manner as in Example 9 except that Compound 50 was used instead of Compound 9 in forming the light emitting layer.

Example 13

An organic light emitting device was fabricated in the same manner as in Example 9 except that Compound 86 was used instead of Compound 9 in forming the light emitting layer.

Example 14

An organic light emitting device was fabricated in the same manner as in Example 9 except that Compound 156 was used instead of Compound 9 in forming the light emitting layer.

Example 15

An organic light emitting device was fabricated using the same method as in Example 1 except that Compound H152 was used instead of ADN in forming the light emitting layer.

Example 16

An organic light emitting device was fabricated in the same manner as in Example 15 except that Compound 11 was used instead of Compound 9 in forming the light emitting layer.

Example 17

An organic light emitting device was fabricated in the same manner as in Example 15 except that Compound 31 was used instead of Compound 9 in forming the light emitting layer.

Example 18

An organic light emitting device was fabricated in the same manner as in Example 15 except that Compound 50 was used instead of Compound 9 in forming the light emitting layer.

Example 19

An organic light emitting device was fabricated in the same manner as in Example 15 except that Compound 73 was used instead of Compound 9 in forming the light emitting layer.

Example 20

An organic light emitting device was fabricated in the same manner as in Example 15 except that Compound 86 was used instead of Compound 9 in forming the light emitting layer.

Example 21

An organic light emitting device was fabricated in the same manner as in Example 15 except that Compound 113 was used instead of Compound 9 in forming the light emitting layer.

Example 22

An organic light emitting device was fabricated using the same method as in Example 1, except that Compound H167 was used instead of ADN in forming the light emitting layer.

Example 23

An organic light emitting device was fabricated in the same manner as in Example 22 except that Compound 11 was used instead of Compound 9 in forming the light emitting layer.

Example 24

An organic light emitting device was fabricated using the same method as in Example 22 except that Compound 31 was used instead of Compound 9 in forming the light emitting layer.

Example 25

An organic light emitting device was fabricated in the same manner as in Example 22 except that Compound 50 was used instead of Compound 9 in forming the light emitting layer.

Example 26

An organic light emitting device was fabricated in the same manner as in Example 22 except that Compound 73 was used instead of Compound 9 in forming the light emitting layer.

Example 27

An organic light emitting device was fabricated in the same manner as in Example 22 except that Compound 86 was used instead of Compound 9 in forming the light emitting layer.

Example 28

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound H204 was used instead of ADN in forming the light emitting layer.

Example 29

An organic light emitting device was fabricated using the same method as in Example 28 except that Compound 11 was used instead of Compound 9 in forming the light emitting layer.

Example 30

An organic light emitting device was fabricated in the same manner as in Example 28 except that Compound 56 was used instead of Compound 9 in forming the light emitting layer.

Example 31

An organic light emitting device was fabricated in the same manner as in Example 1 except that Compound H208 was used instead of ADN in forming the light emitting layer.

Example 32

An organic light emitting device was fabricated in the same manner as in Example 31 except that Compound 11 was used instead of Compound 9 in forming the light emitting layer.

Example 33

An organic light emitting device was fabricated in the same manner as in Example 31 except that Compound 56 was used instead of Compound 9 in forming the light emitting layer.

Comparative Example 3

An organic light emitting device was fabricated in the same manner as in Example 1 except that Compound H109 was used instead of ADN and Compound A was used in place of Compound 9 in forming the light emitting layer.

Evaluation example 1

The driving voltage, current density, luminance, efficiency, and half-life of the organic light-emitting devices fabricated in Examples 1 to 27 and Comparative Examples 1 and 3 were measured using Kethley SMU 236 and luminance meter PR650, . The half life time is the time taken for the luminance to become 50% of the initial luminance after driving the organic light emitting element.

Emitting layer dopant Driving voltage
(V) electric current
density
(mA / cm ² ) Luminance
(cd / m ² ) efficiency
(cd / A) Luminous color Half-life
(hr @
100 mA / cm ² ) Example 1 Compound 9 6.34 50 3,255 6.51 blue 353hr Example 2 Compound 11 6.36 50 3,315 6.63 blue 372hr Example 3 Compound 31 6.30 50 3,370 6.74 blue 363hr Example 4 Compound 32 6.29 50 3,410 6.82 blue 367hr Example 5 Compound 73 6.31 50 3,300 6.60 blue 378hr Example 6 Compound 86 6.27 50 3,365 6.73 blue 351 hr Example 7 Compound 113 6.21 50 3,355 6.71 blue 366hr Example 8 Compound 156 6.13 50 3.275 6.55 blue 342 hr Comparative Example 1 Compound A 6.92 50 2.645 5.29 blue 253hr Comparative Example 2 Compound B 6.96 50 2,730 5.46 blue 248hr

Host Dopant Driving voltage
(V) Current density
(MA / cm2) Luminance
(cd / m 2) efficiency
(cd / A) Luminous color Half-life
(hr @ 100 mA / cm 2) Example 9 Compound H109 Compound 9 6.63 50 3.225 6.75 blue 434hr Example 10 Compound H109 Compound 11 6.64 50 3.225 6.77 blue 442hr Example 11 Compound H109 Compound 31 6.64 50 3,310 6.82 blue 435hr Example 12 Compound H109 Compound 50 6.63 50 3,365 6.84 blue 461 hr Example 13 Compound H109 Compound 86 6.62 50 3,335 6.87 blue 458 hr Example 14 Compound H109 Compound 156 6.61 50 3,375 6.90 blue 438hr Example 15 Compound H152 Compound 9 6.62 50 3,295 6.79 blue 462hr Example 16 Compound H152 Compound 11 6.62 50 3,350 6.90 blue 495hr Example 17 Compound H152 Compound 31 6.63 50 3,325 6.85 blue 463hr Example 18 Compound H152 Compound 50 6.62 50 3,360 6.92 blue 486 hr Example 19 Compound H152 Compound 73 6.61 50 3,320 6.84 blue 484hr Example 20 Compound H152 Compound 86 6.63 50 3,395 7.01 blue 469hr Example 21 Compound H152 Compound 113 6.61 50 3,345 6.95 blue 476hr Example 22 Compound H167 Compound 9 6.62 50 3,310 6.72 blue 413 hr Example 23 Compound H167 Compound 11 6.63 50 3,355 6.91 blue 409hr Example 24 Compound H167 Compound 31 6.64 50 3,380 6.86 blue 425hr Example 25 Compound H167 Compound 50 6.63 50 3,400 6.90 blue 448hr Example 26 Compound H167 Compound 73 6.64 50 3,350 6.83 blue 443hr Example 27 Compound H167 Compound 86 6.61 50 3,360 6.92 blue 433hr Example 28 Compound H204 Compound 9 6.65 50 3,290 6.58 blue 410hr Example 29 Compound H204 Compound 11 6.66 50 3,310 6.62 blue 420hr Example 30 Compound H204 Compound 56 6.62 50 3,315 6.63 blue 408hr Example 31 Compound H208 Compound 9 6.59 50 3,360 6.72 blue 411hr Example 32 Compound H208 Compound 11 6.58 50 3,362 6.72 blue 416 hr Example 33 Compound H208 Compound 56 6.60 50 3,380 6.76 blue 405hr Comparative Example 1 ADN Compound A 6.92 50 2,645 5.29 blue 253hr Comparative Example 3 H109 Compound A 6.73 50 2,835 5.67 blue 372hr

From Table 1 and Table 2, it can be confirmed that the driving voltage, luminance, efficiency, and half life of the organic light emitting devices of Examples 1 to 33 are superior to the driving voltage, efficiency, and half life of the organic light emitting devices of Comparative Examples 1 to 3 .

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

Claims (20)

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

In Formula 1,
X ₁₁ is an oxygen atom (-O-) or a sulfur atom (-S-);
L ₁₁ to L ₁₃ independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cyclo Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene groups, substituted or unsubstituted C ₆ -C ₆₀ arylene groups, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene groups, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene groups, Substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic group (substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic group) );
a11 to a13 are independently selected from 0, 1, 2 and 3;
R ₁₁ to R ₁₆ 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 , A substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent A non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group;
n11 to n13 are independently selected from 0, 1 and 2, and the sum of n11, n12 and n13 is selected from 2, 3, 4, 5 and 6;
R ₁₇ to R ₁₉ independently represent hydrogen, deuterium, F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, Or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ A substituted or unsubstituted C ₁ -C ₁₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-direction Condensed polycyclic group, a substituted or unsubstituted 1, a non-aromatic heterocyclic is selected from a condensed polycyclic group, and _{-Si (Q 1) (Q 2} ) (Q 3);
The substituted C ₃ -C ₁₀ cycloalkylene group, the substituted C ₁ -C ₁₀ heterocycloalkylene group, the substituted C ₃ -C ₁₀ cycloalkenylene group, the substituted C ₁ -C ₁₀ heterocycloalkenylene group, the substituted a C ₆ -C ₆₀ aryl group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted divalent non-aromatic condensed polycyclic group, a substituted bivalent non-condensed polycyclic aromatic heterocyclic group, a substituted C ₁ -C ₆₀ A substituted C ₂ -C ₆₀ alkenyl group, a substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₁ -C ₁₀ hetero A substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted C ₆ -C ₆₀ aryl group, a substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl groups, substituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic hydrocarbon ring, at least one condensed polycyclic group Substituents,
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -N (Q _{11) (Q 12), -Si (Q} 13) (Q 14) (Q 15) and _{-B (Q 16) (Q 17} ) of the at least one substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl , A C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;
C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryl A C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group;
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocyclo alkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ - C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 21) (Q} 22), -Si (Q 23) (Q 24) (Q 25) and _{-B (Q 26) (Q 27} ) of the at least one substituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkyl alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ H. Heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic heterocyclic polycyclic group; And
_{-N (Q 31) (Q 32} ), -Si (Q 33) (Q 34) (Q 35) and _{-B (Q 36) (Q 37} ); ;
Q ₁ to Q _3, Q ₁₁ to Q _17, Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are, each independently, hydrogen, C ₁ -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ together An aryl group, 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,
L ₁₁ to L ₁₃ independently represent a group selected from the group consisting of a phenylene group, a naphthylene group, a fluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a pyrrolylene group, a thiophenylene group, A thiophenylene group, a thienylthio group, a thienylthio group, a thienylthio group, a thienylthio group, a thienylthio group, a thiomorpholinyl group, a thiomorpholinyl group, A benzoimidazolylene group, a benzopyranylene group, a benzothiophenylene group, a triazolylene group, a dibenzofuranylene group, and a dibenzothiophenylene group; And
A halogen atom, a hydroxyl group, a hydrogen atom, a deuterium atom, -F, -Cl, -Br, -I, or a salt thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spy-fluorenyl group, a fluorenyl group benzo, dibenzo-fluorenyl group, a phenanthrenyl group, An anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, A phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a pyrrolylene group, a thiophenylene group, a furanylene group, a pyridinyl group, a phenanthrenyl group, A phenylene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, A benzoimidazolyl group, a benzoimidazolyl group, a benzoimidazolyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, Furanylene group, benzothiophenylene group, triazolylene group, dibenzofuranylene group and dibenzothiophenylene group; &Lt; / RTI &gt; The method according to claim 1,
L ₁₁ to L ₁₃ independently represent an amine compound represented by any one of the following formulas (3-1) to (3-31)

Among the above-mentioned formulas (3-1) to (3-31)
Y ₃₁ is selected from C (R ₃₃ ) (R ₃₄ ), N (R ₃₃ ), O, S, and Si (R ₃₃ ) (R ₃₄ );
R ₃₁ to R ₃₄ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, A sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spioro-fluorenyl group, Anthracenyl group, pyranyl group, pyridinyl group, pyridinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinolyl group, A thiazolyl group, a salinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group;
a31 is selected from 1, 2, 3 and 4;
a32 is selected from 1, 2, 3, 4, 5 and 6;
a33 is selected from 1, 2, 3, 4, 5, 6, 7 and 8;
a34 is selected from 1, 2, 3, 4 and 5;
a35 is selected from 1, 2 and 3;
* And * are independent sites of bonding to neighboring atoms. The method according to claim 1,
and a11 to a13 are each independently selected from 0 and 1. The method according to claim 1,
R ₁₁ to R ₁₆ independently represent a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a pyridinyl group, A phenanthrolinyl group, a phenanthryl group, a benzothiazolyl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, an imidazolyl group, A furanyl group, a benzothiophenyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group and a dibenzoylsilyl group;
A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, A pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, a pyrazinyl group, a pyrazinyl group, a pyridinyl group, possess group and a _{-Si (Q 33) (Q 34} ) (Q 35) of the at least one substituted phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylmethyl group LES, a pyrrolyl group, a thiophenyl group , A furanyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, A phenanthrolinyl group, a phenazinyl group, a benzofuranyl group, a benzothiophenyl group, a triazinyl group, a dibenzoyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, A furanyl group, a dibenzothiophenyl group and a dibenzoylsilyl group; And
A phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, or a phenanthrenyl group substituted with at least one of C ₁ -C ₂₀ alkyl groups substituted with at least one of deuterium, -F, -Cl, -Br, A thiophenyl group, a pyranyl group, a pyridinyl group, a pyranyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a naphthyridinyl group, a quinoxalinyl group A phenanthrolinyl group, a phenazinyl group, a benzofuranyl group, a benzothiophenyl group, a triazinyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, Silol diary; ;
Q ₃₃ to Q ₃₅ are each independently selected from a C ₁ -C ₂₀ alkyl group and a C ₆ -C ₆₀ aryl group. The method according to claim 1,
R ₁₁ to R ₁₆ independently represent an amine compound selected from the following formulas (5-1) to (5-33):

Of the above formulas (5-1) to (5-33)
Y ₅₁ is selected from C (R ₅₃ ) (R ₅₄ ), N (R ₅₃ ), O and S;
R ₅₁ to R ₅₄ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, A sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, -CD ₃ , -CF ₃ , a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, A phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klychenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group , Isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, triazinyl group and -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ); ;
Q ₃₃ to Q ₃₅ independently represent a methyl group, an ethyl group, a tert-butyl group, a phenyl group and a naphthyl group; ;
a51 is selected from 1, 2, 3, 4 and 5;
a52 is selected from 1, 2, 3, 4, 5, 6 and 7;
a53 is selected from 1, 2, 3, 4, 5 and 6;
a54 is selected from 1, 2 and 3;
a55 is selected from 1, 2, 3 and 4;
* Is the binding site with neighboring atoms. The method according to claim 1,
and n11 to n13 are each independently selected from 0 and 1. The method according to claim 1,
And R ₁₇ to R ₁₉ are hydrogen. The method according to claim 1,
An amine compound represented by the following formula (1-1):
&Lt; Formula 1-1 >

In Formula 1-1,
X ₁₁ , L ₁₁ , L ₁₃ , a11, a13, R ₁₁ , R ₁₂ , R ₁₅ and R ₁₆ are as defined in claim 1. The method according to claim 1,
An amine compound represented by the following formula (1-1A):
&Lt; Formula (1-1A)

In the above formula (1-1A)
X ₁₁ , L ₁₁ , L ₁₃ , a11, a13, R ₁₁ , R ₁₂ , R ₁₅ and R ₁₆ are as defined in claim 1. The method according to claim 1,
Wherein the amine compound is any one of the following compounds 1 to 162:

A first electrode; A second electrode; And an organic layer including a light emitting layer interposed between the first electrode and the second electrode, wherein the organic layer contains at least one amine compound of any one of claims 1 to 11. 13. The method of claim 12,
Wherein the light emitting layer further comprises a host, and the amine compound is a dopant. 14. The method of claim 13,
Wherein the host is an anthracene-based compound represented by the following Formula 2:
(2)

In Formula 2,
L ₂₁ represents a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene groups, substituted or unsubstituted C ₆ -C ₆₀ arylene groups, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene groups, substituted or unsubstituted divalent non-aromatic A condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic group;
a21 is selected from 0, 1, 2 and 3;
R ₂₁ to R ₂₃ independently represent hydrogen, deuterium, F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, hwandoen C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, A substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non- An aromatic heterocyclic polycyclic group, -N (Q ₁ ) (Q ₂ ), -Si (Q ₃ ) (Q ₄ ) (Q ₅ ) and -B (Q ₆ ) (Q ₇ );
b21 to b23 are independently of each other selected from 1, 2, 3, 4, 5 and 6;
n21 is selected from 1, 2, and 3;
The substituted C ₃ -C ₁₀ cycloalkylene group, the substituted C ₁ -C ₁₀ heterocycloalkylene group, the substituted C ₃ -C ₁₀ cycloalkenylene group, the substituted C ₁ -C ₁₀ heterocycloalkenylene group, the substituted a C ₆ -C ₆₀ aryl group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted divalent non-aromatic condensed polycyclic group, a substituted bivalent non-condensed polycyclic aromatic heterocyclic group, a substituted C ₁ -C ₆₀ Substituted C ₂ -C ₆₀ alkenyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₆ -C ₆₀ aryl group, a substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl groups, substituted monovalent non-aromatic condensed polycyclic groups, and substituted monovalent non-aromatic hydrocarbon ring condensed at least one substituent of the polycyclic group,
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -N (Q _{11) (Q 12), -Si (Q} 13) (Q 14) (Q 15) and _{-B (Q 16) (Q 17} ) of the at least one substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl , A C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;
C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryl A C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group;
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocyclo alkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ - C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 21) (Q} 22), -Si (Q 23) (Q 24) (Q 25) and _{-B (Q 26) (Q 27} ) of the at least one substituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkyl alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ H. Heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic heterocyclic polycyclic group; And
_{-N (Q 31) (Q 32} ), -Si (Q 33) (Q 34) (Q 35) and _{-B (Q 36) (Q 37} ); ;
Q ₁ to Q _7, Q ₁₁ to Q _17, Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are, each independently, hydrogen, C ₁ -C ₆₀ alkyl, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ together An aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocyclic polycyclic group. 15. The method of claim 14,
L ₂₁ is selected from the following formulas (3-1) to (3-8) and (3-22) to (3-29)

Of the above formulas (3-1) to (3-8) and (3-22) to (3-29)
Y ₃₁ is selected from C (R ₃₃ ) (R ₃₄ ), N (R ₃₃ ), O, S, and Si (R ₃₃ ) (R ₃₄ );
R ₃₁ to R ₃₄ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, A sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spioro-fluorenyl group, Anthracenyl group, pyranyl group, pyridinyl group, pyridinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinolyl group, A thiazolyl group, a salinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group;
a31 is selected from 1, 2, 3 and 4;
a32 is selected from 1, 2, 3, 4, 5 and 6;
a33 is selected from 1, 2, 3, 4, 5, 6, 7 and 8;
a34 is selected from 1, 2, 3, 4 and 5;
a35 is selected from 1, 2 and 3;
* And * are independent sites of bonding to neighboring atoms. 15. The method of claim 14,
R ₂₁ and R ₂₂ are, each independently, hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, _{cyano, -N (Ph) 2, -Si} (CH 3) 3, -Si (Ph) 3 to each other And organic light-emitting elements selected from the following formulas (5-1) to (5-9) and (5-33)

Among the above-mentioned formulas (5-1) to (5-9) and (5-33)
Y ₅₁ is selected from C (R ₅₃ ) (R ₅₄ ), N (R ₅₃ ), O and S;
R ₅₁ to R ₅₄ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, A sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, -CD ₃ , -CF ₃ , a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, A phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klychenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group , Quinoxalinyl group, quinazolinyl group, carbazolyl group, triazinyl group, -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ); And
Q ₃₃ to Q ₃₅ independently represent a methyl group, an ethyl group, a ter-butyl group, a phenyl group, and a naphthyl group; ;
a51 is selected from 1, 2, 3, 4 and 5;
a52 is selected from 1, 2, 3, 4, 5, 6 and 7;
a53 is selected from 1, 2, 3, 4, 5 and 6;
a54 is selected from 1, 2 and 3;
a55 is selected from 1, 2, 3 and 4;
* Is the binding site with neighboring atoms. 15. The method of claim 14,
R ₂₃ is selected from the group consisting of hydrogen, methyl, ethyl, tert-butyl, methoxy, ethoxy, ter-butoxy, -Si (CH ₃ ) ₃ , phenyl and naphthyl. 15. The method of claim 14,
and n21 is 1. 15. The method of claim 14,
Wherein the anthracene compound is represented by any one of the following formulas (2-1) and (2-2):
&Lt; Formula (2-1)

&Lt; Formula (2-2)

Among the formulas (2-1) and (2-2)
L ₂₁ , a ₂₁ , R ₂₁ to R _23, and b ₂₁ to b ₂₃ are as defined in claim 25. 15. The method of claim 14,
Wherein the anthracene-based compound is selected from the following compounds H101 to H188 and H201 to H218:

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