KR102291490B1 - Amine-based compounds and organic light-emitting device comprising the same - Google Patents

Abstract

An amine-based compound and an organic light emitting device including the same are disclosed.

Description

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

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

An organic light-emitting device is a self-luminous device, which has a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed characteristics, and multicolorization. .

In the organic light emitting device, a first electrode is disposed on a substrate, and a hole transport region, a light emitting layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. structure can have. Holes injected from the first electrode move to the emission layer via the hole transport region, and electrons injected from the second electrode move to the emission layer via the electron transport region. Carriers such as holes and electrons recombine in the emission layer region to generate excitons. Light is generated as this exciton changes from an excited state to a ground state.

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

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

<Formula 1>

In Formula 1,

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

L ₁₁ to L ₁₃ are each independently, 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 Alkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted A substituted or unsubstituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic group ) is selected from;

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

R ₁₁ to R ₁₆ are each independently, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group , substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent selected from a non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;

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

R ₁₇ to R ₁₉ are each independently hydrogen, deuterium, F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group Or a salt thereof, 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, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or an 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- selected from a condensed aromatic heteropolycyclic group and -Si(Q ₁ )(Q ₂ )(Q ₃ );

said substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ Alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ hetero Cycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C _{At least one} substituent of the 6 -C ₆₀ arylthio group, the substituted C 1 -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted or unsubstituted monovalent non-aromatic condensed polycyclic group is ,

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

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

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl an oxy group, 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 condensed heteropolycyclic group;

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B(Q ₂₆ )(Q _{27 ), C 3} -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocyclo, substituted with at least one of -B(Q 26 )(Q 27 ). alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is non- -Aromatic heterocondensed polycyclic group; and

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) and -B(Q ₃₆ )(Q ₃₇ ); is selected from;

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 group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ an aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

Another embodiment of the present invention is a first electrode; a second electrode opposite the first electrode; and an organic layer interposed between the first electrode and the second electrode and including a light emitting layer; Including, and the organic layer including at least one selected from the above-described amine-based compounds, discloses an organic light emitting device.

In this embodiment, the host may be an anthracene-based compound represented by the following Chemical Formula 2:

<Formula 2>

In Formula 2,

L ₂₁ is 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, a substituted or unsubstituted A substituted C ₁ -C ₁₀ heterocycloalkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ arylene group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic group selected from a condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group;

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

R ₂₁ to R ₂₃ are each independently 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, a substituted or unsubstituted A substituted 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 ratio -aromatic heterocondensed polycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ) and -B(Q ₆ )(Q ₇ );

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

n21 is selected from 1, 2 and 3;

said substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ Alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ At least one substituent of the arylthio group, the substituted C ₁ -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group is,

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

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

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl an oxy group, 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 condensed heteropolycyclic group;

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B(Q ₂₆ )(Q _{27 ), C 3} -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocyclo, substituted with at least one of -B(Q 26 )(Q 27 ). alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is non- -Aromatic heterocondensed polycyclic group; and

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) and -B(Q ₃₆ )(Q ₃₇ ); is selected from;

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 group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ an aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

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

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

The amine-based compound is represented by the following formula (1):

<Formula 1>

In 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 are each independently, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl a ren group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group;

said substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted _{At least one} substituent of the 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 condensed heteropolycyclic group is,

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

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

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl an oxy group, 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 condensed heteropolycyclic group;

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B(Q ₂₆ )(Q _{27 ), C 3} -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocyclo, substituted with at least one of -B(Q 26 )(Q 27 ). alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is non- -Aromatic heterocondensed polycyclic group; and

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) and -B(Q ₃₆ )(Q ₃₇ ); is selected from;

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 group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group, C ₁ - It may be selected from a C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formula 1, L ₁₁ to L ₁₃ are each independently a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azule Nylene group, heptalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-fluorenylene group, benzofluorenyl group Lene group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group , pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexa Cenylene group, pentacenylene group, rubicenylene group, coronenylene group, ovalenylene group, pyrrolylene group, thiophenylene ( thiophenylene group, furanylene group, imidazolylene group, pyrazolylene group, thiazolylene group, isothiazolylene group, oxazolylene group group, isoxazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, isoindolylene group , indolylene group, indazolylene (indaz) olylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene ( naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinnolinylene group, carbazolylene group, phenanthridinylene group, acridinylene group ) group, phenanthrolinylene group, phenazinylene group, benzoimidazolylene group, benzofuranylene group, benzothiophenylene group, isobenzothiazolylene group (isobenzothiazolylene) group, benzooxazolylene group, isobenzooxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, tria a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group and a dibenzocarbazolylene group; and

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, pentalenyl group, indenyl group, naph Tyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group , ovalenyl 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 group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group , cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, Isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group and imi phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro substituted with at least one of the dazopyridinyl groups -fluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, Naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene group, Pentacenylene group, rubysenylene group, coronenylene group, ovalenylene group, pyrrolylene group, thiophenylene group, furanylene group, imidazolylene group, pyrazolylene group, thiazolylene group, isothiazolylene group, oxazolyl Ren group, isoxazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, isoindolylene group, indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolyl Nylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinolinylene group, carbazolylene group, phenanthridinylene group, acridinylene group, phenanthroly Nylene group, phenazinylene group, benzoimidazolylene group, benzofuranylene group, benzothiophenylene group, isobenzothiazolylene group, benzoxazolylene group, isobenzoxazolylene group, triazolylene group, tetrazolylene group, oxadia a zolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, and a dibenzocarbazolylene group; may be selected from, but is not limited thereto.

As another example, in Formula 1, L ₁₁ to L ₁₃ may each independently represent a phenylene group, a naphthylene group, a fluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a pyrrolylene group, and a thio group. Phenylene group, furanylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, indolylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, naphthyridinylene group, quinoxalinylene group , quinazolinylene group, cinolinylene group, carbazolylene group, phenanthridinylene group, benzoimidazolylene group, benzofuranylene group, benzothiophenylene group, triazolylene group, dibenzofuranylene group and dibenzothiophenyl Rengi; and

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 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 ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, Anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and 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 furanylene group, a pyridinyl group substituted with at least one of a triazinyl group Ren group, pyrazinylene group, pyrimidinylene group, indolylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinolinyl group a ren group, a carbazolylene group, a phenanthridinylene group, a benzoimidazolylene group, a benzofuranylene group, a benzothiophenylene group, a triazolylene group, a dibenzofuranylene group and a dibenzothiophenylene group; may be selected from, but is not limited thereto.

As another example, in Formula 1, L ₁₁ to L ₁₃ may be each independently represented by any one of Formulas 3-1 to 3-31, but are not limited thereto:

In 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 are each independently 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 carboxyl group, or A salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, Dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoc selected from 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, independently of each other, binding sites with neighboring atoms.

As another example, in Formula 1, L ₁₁ to L ₁₃ are each independently represented by any one of 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 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, methyl group, ethyl group, tert-butyl group, methoxy group, ethoxy group, tert-butoxy group, phenyl group, naphthyl group , fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, 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 Formula 1, L ₁₁ to L ₁₃ may be each independently represented by any one of Formulas 4-1 to 4-56, but are not limited thereto:

In Formulas 4-1 to 4-56,

* and *' are, independently of each other, binding sites with neighboring atoms.

As another example, in Formula 1, L ₁₁ to L ₁₃ may be each independently selected from 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 becomes a single bond. When a11 is 2 or more, two or more L ₁₁ may be the same as or different from each other. Descriptions of a12 and a13 may be understood with reference to the description of a11 and the structure of Formula 1 .

For example, in Formula 1, a12 and a13 may be each 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 Formula 1, R ₁₁ to R ₁₆ are each independently selected from a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, or a substituted or unsubstituted C ₃ - C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or an unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;

said substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ - At least _{one substituent of the C 60} aryl group, the substituted C 1 -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted or unsubstituted monovalent non-aromatic condensed polycyclic group is,

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

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

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl an oxy group, 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 condensed heteropolycyclic group;

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B(Q ₂₆ )(Q _{27 ), C 3} -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocyclo, substituted with at least one of -B(Q 26 )(Q 27 ). alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is non- -Aromatic heterocondensed polycyclic group; and

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) and -B(Q ₃₆ )(Q ₃₇ ); is selected from;

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 group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group, C ₁ - It may be selected from a C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formula 1, R ₁₁ to R ₁₆ may each independently represent a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, or a fluorenyl group. , spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphtha Cenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl 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 group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, qui Nolinyl group, isoquinolinyl group, carbazolyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group, cinolinyl group, phenanthry Dinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetra Zolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group and imida dazopyrimidinyl group; and

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, Fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubysenyl group, coronenyl group, ovalenyl 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 group, isoindoleyl group, indolyl group, indazolyl group, furi Nyl group, quinolinyl group, isoquinolinyl group, carbazolyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group, cinolinyl group , carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzoxazole Diary, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group , imidazopyrimidinyl group and -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ) substituted with at least one of a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group , acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, phi Renyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexa Cenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, iso Saazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, carbazolyl group, benzoquinolinyl group Nyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group, cinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, Benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofura nyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group and imidazopyrimidinyl group; is selected from;

Q ₃₃ to Q ₃₅ may be each 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 Formula 1, R ₁₁ to R ₁₆ may each 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, pyridinyl group, pyrazinyl group, pyrimidinyl group, quinolinyl group, isoquinolinyl group, carbazolyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthridinyl group, acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzofuranyl group, a benzothiophenyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group and a dibenzosilolyl group;

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof Salt, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, tria A phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrrolyl group, a thiophenyl group, substituted with at least one of a zinyl group and -Si(Q ₃₃ )(Q ₃₄ )(Q _{35 )} , furanyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, quinolinyl group, isoquinolinyl group, carbazolyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzofuranyl group, benzothiophenyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group and dibenzosilolyl group; and

Deuterium, -F, -Cl, -Br, -I, substituted with at least one of a cyano group and a nitro group, substituted with at least one of a C ₁ -C ₂₀ alkyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl 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, quinoxalinyl group , quinazolinyl group, cinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzofuranyl group, benzothiophenyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group and dibenzo silolyl; is selected from;

Q ₃₃ to Q ₃₅ may be each 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 1, R ₁₁ to R ₁₆ may each 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, and an iso a quinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinolinyl group, a triazinyl group, a dibenzofuranyl group and a dibenzothiophenyl group; and

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof Salt, C ₁ -C ₂₀ alkyl group, -CD ₃ , -CF ₃ , C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorene Nyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quina A phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, a pyridinyl group, a pyrazinyl group, substituted with at least one of a zolinyl group, a carbazolyl group, a triazinyl group, and -Si(Q ₃₃ )(Q ₃₄ )(Q _{35 )} group, pyrimidinyl group, quinolinyl group, isoquinolinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, triazinyl group, dibenzofuranyl group and dibenzothiophenyl group;

Q ₃₃ to Q ₃₅ are each independently selected from a methyl group, an ethyl group, a ter-butyl group, a phenyl group and a naphthyl group; may be selected from, but is not limited thereto.

As another example, in Formula 1, R ₁₁ to R ₁₆ may be each independently selected from Formulas 5-1 to 5-33, but are not limited thereto:

In 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 are each independently 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 carboxyl group, or A salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, -CD ₃ , -CF ₃ , a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-flu Orenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group , isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, triazinyl group, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ); and

Q ₃₃ to Q ₃₅ are each independently selected from a methyl group, an ethyl group, a tert-butyl group, a phenyl group, and a naphthyl group; is selected from;

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 a binding site with a neighboring atom.

As another example, in Formula 1, R ₁₁ to R ₁₆ may be each independently selected from Formulas 6-1 to 6-155, but are not limited thereto:

In Formulas 6-1 to 6-155,

t-Bu is a tert-butyl group;

Ph is a phenyl group;

* is a binding site with a neighboring atom.

As another example, in Formula 1, R ₁₁ to R ₁₆ may be each independently selected from 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 Formula 1, n11 is

As an indication of the number of moieties represented by , it may be selected from 0, 1, and 2. 2 or more if n11 is 2 or more

The moieties represented by may be the same as or different from each other. The description of n12 and n13 may be understood with reference to the description of n11 and the structure of Chemical Formula 1.

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

As another example, in Formula 1, n11 may be 1, n12 may be 0, and n13 may be 1, but is not limited thereto.

In Formula 1, R ₁₇ to R ₁₉ are each independently hydrogen, deuterium, F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydra A group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a 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, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or Unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ Aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted selected from a monovalent non-aromatic condensed heteropolycyclic group and -Si(Q ₁ )(Q ₂ )(Q ₃ );

said substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, Substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio _{group, substituted C 1} -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic hetero condensed group At least one substituent of the polycyclic group is

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

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

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl an oxy group, 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 condensed heteropolycyclic group;

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B(Q ₂₆ )(Q _{27 ), C 3} -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocyclo, substituted with at least one of -B(Q 26 )(Q 27 ). alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is non- -Aromatic heterocondensed polycyclic group; and

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) and -B(Q ₃₆ )(Q ₃₇ ); is selected from;

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 group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ It may be selected from an aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formula 1, R ₁₇ to R ₁₉ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group , hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed hetero polycyclic group, and -Si(Q ₁ )(Q ₂ )(Q ₃ );

Q ₁ to Q ₃ are each independently selected from a C ₁ -C ₆₀ alkyl group and a C ₆ -C ₆₀ aryl group; may be selected from, but is not limited thereto.

As another example, in Formula 1, R ₁₇ to R ₁₉ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, nitro group, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ Alkoxy group, phenyl group, naphthyl group, fluorenyl group, benzofluorenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quin It may be selected from a nolinyl group, 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 Formula 1, R ₁₇ to R ₁₉ may be hydrogen, but the present invention is not limited thereto.

In another embodiment, the amine-based compound represented by Formula 1 may be represented by Formula 1-1 below, 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 above.

For example, in Formula 1-1, L ₁₁ and L ₁₃ may be each independently selected from 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 each independently selected from Formulas 6-1 to 6-155, but are not limited thereto.

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

<Formula 1-1A>

In Formula 1-1A,

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

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

For example, in Formula 1-1A, R ₁₁ , R ₁₂ , R ₁₅ and R ₁₆ may be each independently selected from Formulas 6-1 to 6-155, but are not limited thereto.

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

The amine-based compound represented by Formula 1 includes a core (refer to Formula 1' below) in which benzene and chrysene are connected through an oxygen atom or a sulfur atom.

<Formula 1'>

In the amine-based compound represented by Formula 1, _{π-electrons are delocalized because benzene and chrysene are connected through X 11} (here, X ₁ is an oxygen atom or a sulfur atom). In addition, in the amine-based compound represented by Formula 1, since X ₁₁ includes two pairs of unshared electrons, an extra electron may be provided to the core.

Therefore, since the amine-based compound represented by Formula 1 has a structure rich in π-electrons in its core, the probability of π→π* transition and n→π* transition increases.

The amine-based compound represented by Formula 1 may be synthesized using a known organic synthesis method. A method of synthesizing the amine-based compound may be recognized by those skilled in the art with reference to Examples to be described later.

The amine-based compound represented by Formula 1 may be suitable for use as a dopant in an organic layer of an organic light emitting device, for example, a light emitting layer among the organic layers. Another embodiment may include a first electrode; Disclosed is an organic light emitting device including a second electrode and an organic layer interposed between the first electrode and the second electrode, the organic layer including at least one amine compound represented by Formula 1 and including a light emitting layer.

The organic light emitting device may have characteristics of high efficiency, low driving voltage, and long life by having an organic layer including the amine compound represented by Formula 1 above.

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

In the present specification, "(organic layer) includes one or more amine compounds" means "(organic layer) 1 type of amine compound belonging to the category of Formula 1 or two different types belonging to the category of Formula 1 above. It may include more than one amine-based compound”.

For example, the organic layer may include only Compound 1 as the amine-based compound. In this case, the compound 1 may be present in the emission layer of the organic light emitting device. Alternatively, the organic layer may include Compound 1 and Compound 2 as the amine-based 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, the compound 1 is the light emitting layer) and the compound 2 may be present in the electron transport region).

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

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

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

1 is a schematic 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 method of manufacturing an organic light emitting diode according to an embodiment of the present invention will be described with reference to FIG. 1 .

A substrate may be additionally disposed on a lower portion of the first electrode 110 or an upper portion of the second electrode 190 of FIG. 1 . The substrate may be a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, handling and waterproofness.

The first electrode 110 may be formed, for example, by providing a material for the first electrode on the upper portion of the substrate using a deposition method or a sputtering method. When the first electrode 110 is an anode, the material for the first electrode 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), etc., which are transparent and have excellent conductivity, may be used. Alternatively, in order to form the first electrode 110 that is a transflective electrode or a reflective electrode, as a material for the first electrode, magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca) ), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) may be selected.

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 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 emission layer. The organic layer 150 may further include an electron transport region interposed between the emission layer and the second electrode.

The hole transport region may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a buffer layer, and an electron blocking layer (EBL), and the electron transport region may include a hole blocking layer (HBL) and an electron transport layer. It may include at least one of (ETL) and an electron injection layer (EIL), but is not limited thereto.

The hole transport region may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

For example, the hole transport region may have a single layer structure made of a plurality of different materials, or a hole injection layer/hole transport layer, a hole injection layer/hole transport layer/buffer layer that are sequentially stacked from the first electrode 110 . , a hole injection layer/buffer layer, a hole transport layer/buffer layer, or a hole injection layer/hole transport layer/electron blocking layer, but is not limited thereto.

When the hole transport region includes a hole injection layer, a vacuum deposition method, a spin coating method, a casting method, a LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser thermal imaging method (Laser Induced Thermal Imaging, LITI) The hole injection layer may be formed on the first electrode 110 by using various methods, such as.

When the hole injection layer is formed by vacuum deposition, deposition conditions are, for example, a deposition temperature of about 100 to about 500° C., ^{a vacuum degree of about 10 -8} to about 10 ^-3 torr, and about 0.01 to about 100 Å/sec. Within the deposition rate range of , the compound may be selected in consideration of a compound for a hole injection layer to be deposited and a structure of a hole injection layer to be formed.

When the hole injection layer is formed by spin coating, the coating conditions are within the range of a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature of about 80° C. to 200° C., the compound for the hole injection layer to be deposited and the hole to be formed. It may be selected in consideration of the injection layer structure.

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

The hole transport region is, m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, α-NPB, TAPC, HMTPD, TCTA (4,4',4"- Tris(N-carbazolyl)triphenylamine (4,4',4"-tris(N-carbazolyl)triphenylamine)), Pani/DBSA (Polyaniline/Dodecylbenzenesulfonic acid: polyaniline/dodecylbenzenesulfonic acid), PEDOT/PSS ( Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate):poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate)), Pani/CSA (Polyaniline/Camphor sulfonicacid:polyaniline/camphor) sulfonic acid), PANI/PSS (Polyaniline)/Poly(4-styrenesulfonate):polyaniline)/poly(4-styrenesulfonate)), a compound represented by the following Chemical Formula 201 and a compound represented by the following Chemical Formula 202. can do:

<Formula 201>

<Formula 202>

In Formulas 201 and 202,

L ₂₀₁ to L ₂₀₅ are each independently, 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 Alkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted It is selected from a cyclic divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

said substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted _{At least one} substituent of the 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 condensed polycyclic group is,

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof salts, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric 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 heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₂₀₁ )(Q ₂₀₂ ), -Si(Q ₂₀₃ )(Q ₂₀₄ )(Q _{205 ), C 1} -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C substituted with at least one of -B(Q ₂₀₆ )(Q _{207 ) 2} -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl an oxy group, 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 condensed heteropolycyclic group;

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof salt, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocondensed polycyclic group, -N(Q ₂₁₁ )(Q ₂₁₂ ), -Si(Q ₂₁₃ )(Q ₂₁₄ )(Q ₂₁₅ ) and - _{C 3} -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, substituted with at least one of B(Q ₂₁₆ )(Q _{217 )} , C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic Heterocondensed polycyclic group; and

-N(Q ₂₂₁ )(Q ₂₂₂ ), -Si(Q ₂₂₃ )(Q ₂₂₄ )(Q ₂₂₅ ) and -B(Q ₂₂₆ )(Q ₂₂₇ ); is selected from;

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

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

R ₂₀₁ to R ₂₀₅ are each independently selected from 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;

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric 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 heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, —N(Q ₂₃₁ )(Q) ₂₃₂ ), -Si(Q ₂₃₃ )(Q ₂₃₄ )(Q ₂₃₅ ) and -B(Q ₂₃₆ )(Q _{237 ), C 1} -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C substituted with at least one ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl an oxy group, 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 condensed heteropolycyclic group; and

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof salt, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₂₄₁ )(Q ₂₄₂ ), -Si(Q ₂₄₃ )(Q ₂₄₄ )(Q ₂₄₅ ) and - _{C 3} -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, substituted with at least one of B(Q ₂₄₆ )(Q _{247 )} , C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic Heterocondensed polycyclic group; is selected from;

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 are each independently 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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ an alkenyl group, a C ₂ -C ₆₀ alkynyl group, and a C ₁ -C ₆₀ alkoxy group;

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric 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 heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C _{substituted with at least one of a 60} aryloxy group, 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 condensed heteropolycyclic group, C ₁ - C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl an oxy group, 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 condensed heteropolycyclic group; and

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof salt, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C _{60 C 3} -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ substituted with at least one of a heteroaryl group, a monovalent non-aromatic condensed 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 a non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group; is selected from

For example, in Formulas 201 and 202,

L ₂₀₁ to L ₂₀₅ are each independently, a phenylene group, a naphthylenylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthra Cenylene group, pyrenylene group, chrysenylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, quinolinylene group, isoquinolinylene group, quinoxalinylene group, quinazolinylene group, a carbazolylene group and a triazinylene group; and

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof Salt, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazole a phenylene group, a naphthylenylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, Anthracenylene group, pyrenylene group, chrysenylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, quinolinylene group, isoquinolinylene group, quinoxalinylene group, quinazolinylene group , a carbazolylene group and a triazinylene group; is selected from;

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

xa5 is 1, 2 or 3;

R ₂₀₁ to R ₂₀₅ are each independently, 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 cry a cenyl 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; and

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof Salt, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, azulenyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthree Nyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl 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, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; may be selected from, but is not limited thereto.

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

<Formula 201A>

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

<Formula 201A-1>

The compound represented by Chemical Formula 202 may be represented by the following Chemical Formula 202A, but is not limited thereto:

<Formula 202A>

_{Descriptions of L 201} to L ₂₀₃ , xa1 to xa3 , xa5 and R ₂₀₂ to R ₂₀₄ in Formulas 201A, 201A-1 and 202A refer to those described herein, and R ₂₁₁ and R ₂₁₂ are the description of R ₂₀₃ Reference, R ₂₁₃ to R ₂₁₆ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydra Group, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ arylox group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group; can be selected from

For example, in Formulas 201A, 201A-1, and 202A, L ₂₀₁ to L ₂₀₃ may each independently represent a phenylene group, a naphthylenylene group, a fluorenylene group, a spiro-fluorenylene group, or a benzofluorenyl group. Ren group, dibenzofluoro grouprenylene group, phenanthrenylene group, anthracenylene group, pyrenylene group, chrysenylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, quinolinylene group, iso a quinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group and a triazinylene group; and

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof Salt, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group A phenylene group, a naphthylenylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorogirenylene group, a phenanthrenylene group, an anthracenylene group, substituted with at least one selected from the group , pyrenylene group, chrysenylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, quinolinylene group, isoquinolinylene group, quinoxalinylene group, quinazolinylene group, carbazolyl a ren group and a triazinylene group; is selected from;

xa1 to xa3 are each independently 0 or 1;

R ₂₀₃ , R ₂₁₁ and R ₂₁₂ are each independently selected from 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 pyrene group nyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; and

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof Salt, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl 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 chrysenyl group, substituted with at least one selected from the group , pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; is selected from;

R ₂₁₃ and R ₂₁₄ are each independently selected from a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof Salt, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyra _{A C 1} -C ₂₀ alkyl group substituted with at least one selected from a zinyl 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 C ₁ -C ₂₀ alkoxy group;

Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group , pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; and

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof Salt, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl 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 chrysenyl group, substituted with at least one selected from the group , pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; is selected from;

R ₂₁₅ and R ₂₁₆ are each independently 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 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 ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof Salt, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyra _{A C 1} -C ₂₀ alkyl group substituted with at least one selected from a zinyl 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 C ₁ -C ₂₀ alkoxy group;

Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group , pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group and triazinyl group; and

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof Salt, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl 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 chrysenyl group, substituted with at least one selected from the group , pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group and triazinyl group; is selected from;

xa5 is 1 or 2.

In Formulas 201A and 201A-1, R ₂₁₃ and R ₂₁₄ may be bonded to each other to form a saturated or unsaturated ring.

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

The hole transport region may have a thickness of about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å. If the hole transport region includes both a hole injection layer and a hole transport layer, the thickness of the hole injection layer is about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å, and the thickness of the hole transport layer is about 50 Å to about 2000 Angstroms, for example about 100 Angstroms to about 1500 Angstroms. When the thickness of the hole transport region, the hole injection layer, and the hole transport layer satisfies the above-described ranges, satisfactory hole transport characteristics may be obtained without a substantial increase in driving voltage.

The hole transport region may further include a charge-generating material to improve conductivity in addition to the above-described material. The charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region.

The charge-generating 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 tetracyanoquinonedimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane quinone derivatives such as phosphorus (F4-TCNQ) and the like; metal oxides such as tungsten oxide and molybdenum oxide; and the following compound HT-D1, but is not limited thereto.

<Compound HT-D1> <F4-TCNQ>

The hole transport region may further include at least one of a buffer layer and an electron blocking layer in addition to the hole injection layer and the hole transport layer as described above. The buffer layer may serve to increase light emission efficiency by compensating for an optical resonance distance according to a wavelength of light emitted from the light emitting layer. As a material included in the buffer layer, a material capable of being included in the hole transport region may be used. The electron blocking layer is a layer that serves to prevent electron injection from the electron transport region.

A vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, or a laser induced thermal imaging (LITI) method on the upper portion of the first electrode 110 or on the hole transport region ) to form the light emitting layer using various methods such as When the light emitting layer is formed by vacuum deposition and spin coating, the deposition conditions and coating conditions of the light emitting layer refer to the deposition conditions and coating conditions 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 each sub-pixel. Alternatively, the light-emitting layer has a structure in which a red light-emitting layer, a green light-emitting layer, and a blue light-emitting layer are stacked, or a structure in which a red light-emitting material, a green light-emitting material, and a blue light-emitting material are mixed without layer distinction, so that white light can be emitted. Alternatively, the light emitting layer may be a white light emitting layer, and may further include a color converting layer for converting the white light into light of a desired color or a color filter.

The emission layer may include a host and a dopant.

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

<Formula 301>

Ar ₃₀₁ -[(L ₃₀₁ ) _xb1 -R ₃₀₁ ] _xb2

In Formula 301, Ar ₃₀₁ is naphthalene, heptalene, fluorene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, or phenanthrene. ), anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene and indenoanthracene;

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof salt, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C 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 condensed heteropolycyclic group, and -Si(Q ₃₀₁ )(Q ₃₀₂ )(Q ₃₀₃ ) (wherein Q ₃₀₁ to Q ₃₀₃ are independently of each other, hydrogen , C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group) substituted with at least one selected from), naphthalene, heptalene, fluorene, Spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphen and indeno anthracene; is selected from;

For the description of L ₃₀₁ , refer to the description _{of L 201 in the present specification;}

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

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof Salt, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyra _{A C 1} -C ₂₀ alkyl group substituted with at least one selected from a zinyl 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 C ₁ -C ₂₀ alkoxy group;

Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group , pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazole group and triazinyl group; and

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof Salt, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl 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 chrysenyl group, substituted with at least one selected from the group , pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; is selected from;

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 a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, and a phenanthrenylene group. , anthracenylene group, pyrenylene group and chrysenylene group; and

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof Salt, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a trenylene group, an anthracenylene group, a pyrenylene group and a chrysenylene group; is selected from;

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

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof substituted with at least one selected from a salt, 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 chrysenyl 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 chrysenyl group; and

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof Salt, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl 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, substituted with at least one selected from a group, a pyrenyl group and a chrysenyl group , a pyrenyl group and a chrysenyl group; may be selected from, 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 at least one of the following compounds H26 to H32, but is not limited thereto:

For example, the host may include an anthracene-based compound represented by the following Chemical Formula 2:

<Formula 2>

In Formula 2,

L ₂₁ is 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, a substituted or unsubstituted A substituted C ₁ -C ₁₀ heterocycloalkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ arylene group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic group selected from a condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group;

a21 is selected from 0, 1, 2 and 3; when a21 is 2 or more, a plurality of L ₂₁ are the same as or different from each other;

R ₂₁ to R ₂₃ are each independently 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, a substituted or unsubstituted A substituted 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 ratio -aromatic heterocondensed polycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ) and -B(Q ₆ )(Q ₇ );

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

n21 is selected from 1, 2 and 3;

said substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ Alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ At least one substituent of the arylthio group, the substituted C ₁ -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group is,

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

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

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl an oxy group, 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 condensed heteropolycyclic group;

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B(Q ₂₆ )(Q _{27 ), C 3} -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocyclo, substituted with at least one of -B(Q 26 )(Q 27 ). alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is non- -Aromatic heterocondensed polycyclic group; and

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) and -B(Q ₃₆ )(Q ₃₇ ); is selected from;

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 group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ an aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formula 2, L ₂₁ is a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, Spiro-fluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenyl group Ren group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, rubycenylene group, coronenylene group, ovalenylene group, pyrrolylene group, thiophenylene group, fury Ranylene group, imidazolylene group, pyrazolylene group, thiazolylene group, isothiazolylene group, oxazolylene group, isoxazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, isoindole Ilene group, indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinyl group Ren group, cinolinylene group, carbazolylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoimidazolylene group, benzofuranylene group, benzothiophenylene group, isobenzothiazolyl Rene group, benzoxazolylene group, isobenzooxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, and dibenzocarba zolylene group; and

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, pentalenyl group, indenyl group, naph Tyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group , ovalenyl 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 group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group , cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, Isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group and imi phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro substituted with at least one of the dazopyridinyl groups -fluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, Naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene group, Pentacenylene group, rubysenylene group, coronenylene group, ovalenylene group, pyrrolylene group, thiophenylene group, furanylene group, imidazolylene group, pyrazolylene group, thiazolylene group, isothiazolylene group, oxazolyl Ren group, isoxazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, isoindolylene group, indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolyl Nylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinolinylene group, carbazolylene group, phenanthridinylene group, acridinylene group, phenanthroly Nylene group, phenazinylene group, benzoimidazolylene group, benzofuranylene group, benzothiophenylene group, isobenzothiazolylene group, benzoxazolylene group, isobenzoxazolylene group, triazolylene group, tetrazolylene group, oxadia a zolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, and a dibenzocarbazolylene group; may be selected from, but is not limited thereto.

As another example, in Formula 2, L ₂₁ is a phenylene group, a naphthylene group, a fluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a carbazolylene group, a dibenzofunanylene group, and a dibenzo thiophenylene group; and

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 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 ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, Anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and a phenylene group, a naphthylene group, a fluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a carbazolylene group, a dibenzofunanylene group, and a dibenzothiophenyl group substituted with at least one of a triazinyl group Rengi; may be selected from, but is not limited thereto.

As another example, in Formula 2, L ₂₁ may be selected from Formulas 3-1 to 3-8 and 3-22 to 3-29, but is not limited thereto:

In 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 are each independently 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 carboxyl group, or A salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, Dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoc selected from 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, independently of each other, binding sites with 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 to In 3-29, R ₃₁ to R ₃₄ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, methyl group, ethyl group, tert-butyl group, methoxy group, ethoxy group, tert-butoxy group , phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group It may be selected from a 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 Formula 2, L ₂₁ may be selected from Formulas 4-1 to 4-11 and 4-31 to 4-54, but is not limited thereto:

In Formulas 4-1 to 4-11 and 4-31 to 4-54,

* and *' are, independently of each other, binding sites with 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 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, phenyl group, pentalenyl group, indenyl group, naphthyl group, Azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, Fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group, oh Valenyl 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, pyri Dazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, carbazolyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, benzo Quinoxalinyl group, quinazolinyl group, benzoquinazolinyl group, cinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothia Zolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazolyl group , dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, -N(Q ₁ )(Q ₂ ) and -Si(Q ₃ )(Q ₄ )(Q ₅ ); and

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, Fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubysenyl group, coronenyl group, ovalenyl 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 group, isoindoleyl group, indolyl group, indazolyl group, furi Nyl group, quinolinyl group, isoquinolinyl group, carbazolyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group, cinolinyl group , carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzoxazole Diary, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group , imidazopyrimidinyl group and -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ) substituted with at least one of a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group , acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, phi Renyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexa Cenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, iso Saazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, carbazolyl group, benzoquinolinyl group Nyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group, cinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, Benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofura nyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group and imidazopyrimidinyl group; is selected from;

Q ₁ to Q ₅ and Q ₃₃ to Q ₃₅ may be each 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 Formula 2, R ₂₁ and R ₂₂ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl 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, quinoxali Nyl group, quinazolinyl group, cinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzofuranyl group, benzothiophenyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, di benzosilolyl groups, —N(Q ₁ )(Q ₂ ) and —Si(Q ₃ )(Q ₄ )(Q ₅ ); and

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof Salt, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, tria A phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrrolyl group, a thiophenyl group, substituted with at least one of a zinyl group and -Si(Q ₃₃ )(Q ₃₄ )(Q _{35 )} , furanyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, quinolinyl group, isoquinolinyl group, carbazolyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzofuranyl group, benzothiophenyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group and dibenzosilolyl group; and

Deuterium, -F, -Cl, -Br, -I, substituted with at least one of a cyano group and a nitro group, substituted with at least one of a C ₁ -C ₂₀ alkyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl 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, quinoxalinyl group , quinazolinyl group, cinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzofuranyl group, benzothiophenyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group and dibenzo silolyl; is selected from;

Q ₁ to Q ₅ and Q ₃₃ to Q ₃₅ may be each 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 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, phenyl group, naphthyl group, fluorenyl group, phenanthrene Nyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, quinolinyl group, isoquinolinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, triazinyl group, dibenzofuranyl group, dibenzo thiophenyl groups, -N(Q ₁ )(Q ₂ ) and -Si(Q ₃ )(Q ₄ )(Q ₅ ); and

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof Salt, C ₁ -C ₂₀ alkyl group, -CD ₃ , -CF ₃ , C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorene Nyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quina A phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, a pyridinyl group, a pyrazinyl group, substituted with at least one of a zolinyl group, a carbazolyl group, a triazinyl group, and -Si(Q ₃₃ )(Q ₃₄ )(Q _{35 )} group, pyrimidinyl group, quinolinyl group, isoquinolinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, triazinyl group, dibenzofuranyl group and dibenzothiophenyl group;

Q ₁ to Q ₅ and Q ₃₃ to Q ₃₅ are each independently selected from a methyl group, an ethyl group, a tert-butyl group, a phenyl group and a naphthyl group; may be selected from, but is not limited thereto.

As another example, in Formula 2, R ₂₁ and R ₂₂ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, -N(Ph) ₂ , -Si(CH) ₃ ) ₃ , -Si(Ph) ₃ and may be selected from the following Chemical Formulas 5-1 to 5-9 and 5-33, but is not limited thereto:

In 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 are each independently 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 carboxyl group, or A salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, -CD ₃ , -CF ₃ , a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-flu Orenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group , isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, triazinyl group and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ); is selected from;

Q ₃₃ to Q ₃₅ are each independently selected from a methyl group, an ethyl group, a ter-butyl group, a phenyl group and a naphthyl group; is selected from;

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 a binding site with a neighboring atom.

As another example, in Formula 2, R ₂₁ and R ₂₂ may be each independently selected from Formulas 6-1 to 6-42 and 6-140 to 6-155, but are not limited thereto:

In 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 a binding site with a neighboring atom.

For example, in Formula 2, R ₂₃ is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group , a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group , a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heterocondensed polycyclic group, and -Si(Q ₃ )(Q ₄ )(Q ₅ );

Q ₃ to Q ₅ may be each independently selected from a C ₁ -C ₆₀ alkyl group and a C ₆ -C ₆₀ aryl group; may be selected from, but is not limited thereto.

As another example, in Formula 2, R ₂₃ is hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, nitro group, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, Phenyl group, naphthyl group, fluorenyl group, benzofluorenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolyl group It may be selected from a nyl group, a carbazolyl group, a triazinyl group, -Si(CH ₃ ) ₃ and -Si(Ph) ₃ , but is not limited thereto.

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

For example, in Formula 2, b21 to b23 may be each 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-based compound represented by Chemical Formula 2 may be selected from the following Chemical Formulas 2-1 and 2-2, but is not limited thereto:

<Formula 2-1>

<Formula 2-2>

In Formulas 2-1 and 2-2,

L ₂₁ , a21 , R ₂₁ to R _{23 ,} and b21 to b23 refer to the above.

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

<Formula 2-1A>

<Formula 2-2A>

In Formulas 2-1A and 2-2A,

L ₂₁ , a21 , R ₂₁ to R ₂₃ and b21 and b22 refer to the above.

For example, the anthracene-based 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 an embodiment, the emission layer of the organic light emitting device includes the amine compound represented by Formula 1 as a dopant.

The emission 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-based compound represented by Formula 1 above.

The phosphorescent dopant may include an organometallic complex represented by the following Chemical Formula 401:

<Formula 401>

In 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 are each independently a nitrogen atom or a carbon atom;

A ₄₀₁ and A ₄₀₂ rings independently of each other, substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted spiro-fluorene, substituted or unsubstituted indene , substituted or unsubstituted pyrrole, substituted or unsubstituted thiophene, substituted or unsubstituted furan, substituted or unsubstituted imidazole, substituted or unsubstituted pyrazole, substituted or unsubstituted thiazole, substituted or unsubstituted isothiazole, substituted or unsubstituted oxazole, substituted or unsubstituted isoxazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridazine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted benzoquinoline, substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazoline, substituted or unsubstituted substituted or unsubstituted benzoimidazole, substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophene, substituted or unsubstituted isobenzothiophene, substituted or unsubstituted benzo oxazole, substituted or unsubstituted isobenzoxazole, substituted or unsubstituted triazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted triazine, substituted or unsubstituted dibenzofuran and selected from substituted or unsubstituted dibenzothiophenes;

substituted benzene, substituted naphthalene, substituted fluorene, substituted spiro-fluorene, substituted indene, substituted pyrrole, substituted thiophene, substituted furan, substituted imidazole, substituted pyrazole, substituted substituted thiazole, substituted isothiazole, substituted oxazole, substituted isoxazole, substituted pyridine, substituted pyrazine, substituted pyrimidine, substituted pyridazine, substituted quinoline, substituted isoquinoline, substituted benzo Quinoline, substituted quinoxaline, substituted quinazoline, substituted carbazole, substituted benzoimidazole, substituted benzofuran, substituted benzothiophene, substituted isobenzothiophene, substituted benzoxazole, substituted iso At least one substituent of benzoxazole, substituted triazole, substituted oxadiazole, substituted triazine, substituted dibenzofuran and substituted dibenzothiophene is

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof salts, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric 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 heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N (Q ₄₀₁ )(Q ₄₀₂ ), -Si(Q ₄₀₃ )(Q ₄₀₄ )(Q ₄₀₅ ) and -B(Q ₄₀₆ )(Q ₄₀₇ ), C ₁ -C ₆₀ alkyl group, C ₂ - C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl an oxy group, 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 condensed heteropolycyclic group;

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof salt, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic 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 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic Heterocondensed polycyclic group; and

-N(Q ₄₂₁ )(Q ₄₂₂ ), -Si(Q ₄₂₃ )(Q ₄₂₄ )(Q ₄₂₅ ) and -B(Q ₄₂₆ )(Q ₄₂₇ ); is selected from;

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 each independently, independently of each other, hydrogen, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₆ -C ₆₀ aryl group and a C ₁ -C ₆₀ heteroaryl group;

L ₄₀₁ may be any monovalent, divalent, or trivalent organic ligand. For example, L ₄₀₁ is a halogen ligand (eg Cl, F), a diketone ligand (eg acetylacetonate, 1,3-diphenyl-1,3-propanedionate, 2,2, 6,6-tetramethyl-3,5-heptanedionate, hexafluoroacetonate), carboxylic acid ligands (eg picolinate, dimethyl-3-pyrazolecarboxylate, benzoate), carbon It may be selected from a monoxide ligand, an isonitrile ligand, a cyano ligand, and a phosphorus ligand (eg, phosphine, phosphaite), but is not limited thereto.

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 in Formula 401

may be the same as or different from each other. In Formula 401, when xc1 is 2 or more, A ₄₀₁ and A ₄₀₂ are each directly or a linking group (eg, C ₁ -C ₅ alkylene group, C _{2 ) with A 401} and A ₄₀₂ of another ligand, respectively. -C ₅ alkenylene group, -N(R')- (wherein R' is a C ₁ -C ₁₀ alkyl group or C ₆ -C ₂₀ aryl group) or -C(=O)-) may be connected therebetween. have.

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

Alternatively, the phosphorescent dopant may include the following PtOEP:

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

Alternatively, the fluorescent dopant may include a compound represented by the following Chemical Formula 501:

<Formula 501>

In Formula 501,

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

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof salt, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group and -Si(Q ₅₀₁ )(Q ₅₀₂ )(Q ₅₀₃ ) (wherein Q ₅₀₁ to Q ₅₀₃ are independently of each other, hydrogen , C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group) substituted with at least one selected from), naphthalene, heptalene, fluorene, Spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphen and indeno anthracene; is selected from;

For the description of L ₅₀₁ to L ₅₀₃ , refer to the description _{of L 201 in the present specification, respectively;}

R ₅₀₁ and R ₅₀₂ are each independently, 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 cry cenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, triazinyl group, dibenzofuranyl group, and dibenzothiophenyl group; and

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof Salt, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, triazinyl group a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, anthra Cenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, tria a zinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; is selected from;

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

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

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

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

The light emitting layer may have a thickness of 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 range, excellent light emitting characteristics may be exhibited without a substantial increase in driving voltage.

Next, an electron transport region may be disposed on the emission 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 transport region may have a structure of an electron transport layer/electron injection layer or a hole blocking layer/electron transport layer/electron injection layer sequentially stacked from the emission layer, but is not limited thereto.

The electron transport region may include a hole blocking layer. The hole blocking layer may be formed in order to prevent the diffusion of triplet excitons or holes into the electron transport layer when the light emitting layer uses a phosphorescent dopant.

When the electron transport region includes a hole blocking layer, a vacuum deposition method, a spin coating method, a cast method, a LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser thermal imaging method (Laser Induced Thermal Imaging, LITI) The hole blocking layer may be formed on the light emitting layer by using various methods, such as. When the hole blocking layer is formed by vacuum deposition and spin coating, the deposition conditions and coating conditions of the hole blocking layer refer to the deposition conditions and coating conditions 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 hole blocking layer may have a thickness of 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 range, excellent hole blocking characteristics can be obtained without a substantial increase in driving voltage.

The electron transport region may include an electron transport layer. The electron transport layer is formed by using various methods such as a vacuum deposition method, a spin coating method, a casting method, a LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, and a laser thermal imaging method (Laser Induced Thermal Imaging, LITI). It may be formed on the light emitting layer or on the hole blocking layer. When the electron transport layer is formed by vacuum deposition and spin coating, the deposition conditions and 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 BCP, Bphen, and Alq ₃ , Balq, TAZ, and NTAZ.

Alternatively, the electron transport layer may include at least one of the compounds represented by the following Chemical Formula 601:

<Formula 601>

Ar ₆₀₁ -[(L ₆₀₁ ) _xe1 -E ₆₀₁ ] _xe2

In Formula 601, Ar ₆₀₁ is naphthalene, heptalene, fluorene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, or phenanthrene. ), anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene and indenoanthracene;

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof salt, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C 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 condensed heteropolycyclic group, and -Si(Q ₃₀₁ )(Q ₃₀₂ )(Q ₃₀₃ ) (wherein Q ₃₀₁ to Q ₃₀₃ are independently of each other, hydrogen , C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group) substituted with at least one selected from), naphthalene, heptalene, fluorene, Spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphen and indeno anthracene; is selected from;

For the description of L ₆₀₁ , refer to the description _{of L 201 in the present specification;}

E ₆₀₁ is a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group (isothiazolyl) group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group (benzoquinolinyl) group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, Benzothiophenyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadia Zolyl (oxadiazolyl) group, triazinyl (triazinyl) group, dibenzofuranyl (dibenzofuranyl) group, dibenzothiophenyl (dibenzothiophenyl) group, benzocarbazolyl group and dibenzocarbazolyl group; and

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof Salt, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spy Rho-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group , picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thia Zolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group , isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phena Zinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, A pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, and isothiazole substituted with at least one of a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group Diary, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, Benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazole Diary, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and dibenzocarbazolyl group; is selected from;

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

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

Alternatively, the electron transport layer may include at least one of compounds represented by the following Chemical Formula 602:

<Formula 602>

In Formula 602,

X ₆₁₁ 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 the present specification;}

R ₆₁₁ to R ₆₁₆ are each independently, 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 cry a cenyl 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; and

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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof Salt, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, azulenyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthree Nyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl 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, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; is selected from;

xe611 to xe616 are each 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 electron transport layer may have a thickness of about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer satisfies the above range, a satisfactory electron transport characteristic may be obtained without a substantial increase in driving voltage.

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

The metal-containing material may include 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 injection layer is formed using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB), inkjet printing, laser printing, and laser induced thermal imaging (LITI). , may be formed on the electron transport layer. When the electron injection layer is formed by the vacuum deposition method or the spin coating method, the deposition conditions and coating conditions of the electron injection layer refer to the deposition conditions and 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 electron injection layer may have a thickness of about 1 Å to about 100 Å, and about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the above range, a satisfactory level of electron injection characteristics may be obtained without a substantial increase in driving voltage.

The second electrode 190 is disposed on the organic layer 150 as described above. The second electrode 190 may be a cathode that is an electron injection electrode. In this case, as a material for the second electrode 190 , a metal, an alloy, an electrically conductive compound, and a mixture thereof having a low work function. can be used Specific examples of the material for the second electrode 190 include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In). , magnesium-silver (Mg-Ag) and the like may be included. 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.

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

In the present specification, the C ₁ -C ₆₀ alkyl group refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples thereof include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, pentyl group, iso-amyl group, hexyl group and the like are included. In the present specification, the C ₁ -C ₆₀ alkylene group refers to a divalent group having the same structure as _{the C 1} -C _{60 alkyl group.}

In the present specification, the C ₁ -C ₆₀ alkoxy group refers to a _{monovalent group having the formula of -OA 101} (here, A _{101 is the C 1} -C ₆₀ alkyl group), and specific examples thereof include a methoxy group, an ethoxy group , an isopropyloxy group, and the like.

In the present specification, the C ₂ -C ₆₀ alkenyl group refers to a hydrocarbon group including one or more carbon double bonds in the middle or at the terminal of _{the C 2} -C _{60 alkyl group, and specific examples thereof include an ethenyl group, a propenyl group, a butenyl group.} etc. are included. In the present specification, the C ₂ -C ₆₀ alkenylene group refers to 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 refers to a hydrocarbon group including one or more carbon triple bonds in the middle or at the terminal of the C ₂ -C _{60 alkyl group, and specific examples thereof include an ethynyl group, propy} nyl (propynyl) group and the like. In the present specification, the C ₂ -C ₆₀ alkynylene group refers to 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 refers to 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, and a cyclo a 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 refers to 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, and its Specific examples include a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and the like. In the present specification, the C ₁ -C ₁₀ heterocycloalkylene group refers to a divalent group having the same structure as the 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, and refers to a group having at least one double bond in the ring, but not having aromaticity, and a specific 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 refers to 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, and is at least in the ring. has one double bond. Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl include a 2,3-hydrofuranyl group, a 2,3-hydrothiophenyl group, and the like. In the present specification, the C ₁ -C ₁₀ heterocycloalkenylene group refers to a divalent group having the same structure as the C ₁ -C _{10 heterocycloalkenyl group.}

In the specification C ₆ -C ₆₀ aryl group refers to a monovalent (monovalent) group with the carbon atom between the aromatic system of 6 to 60, and carbonyl, C ₆ -C ₆₀ arylene group of 6 to 60 carbon atoms, carbonyl It refers to 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, and a chrysenyl group. When the C ₆ -C ₆₀ aryl group and the C ₆ -C ₆₀ arylene group include two or more rings, the two or more rings may be fused to each other.

In the present specification, the C ₁ -C ₆₀ heteroaryl group refers to a monovalent group including at least one hetero atom selected from N, O, P and S as a ring-forming atom and having a carbocyclic aromatic system having 1 to 60 carbon atoms. and C ₁ -C ₆₀ heteroarylene group means a divalent group including at least one hetero atom 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, the two or more rings may be fused to each other.

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, A ₁₀₃ represents the above C ₆ -C ₆₀ aryl group).

In the present specification, a monovalent non-aromatic condensed polycyclic group has two or more rings condensed with each other, contains only carbon as a ring-forming atom, and the entire molecule is non-aromatic. means a monovalent group having Specific 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 refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

In the present specification, the monovalent non-aromatic condensed heteropolycyclic group includes two or more rings condensed with each other, and a hetero atom selected from N, O, P and S in addition to carbon as a ring forming atom, and , refers to a monovalent group in which the entire molecule has non-aromaticity. The monovalent non-aromatic condensed heteropolycyclic group includes carbazolyl and the like. In the present specification, the condensed divalent non-aromatic heteropolycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

In the present specification, "Ph" means phenyl, "Me" means methyl, "Et" means ethyl, and "ter-Bu" or "But ^t " means tert-butyl.

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

[Example]

Synthesis example 1: Synthesis of compound 9

Synthesis of Intermediate 9-1

After dissolving 5.2 g (23.6 mmol) of 2-bromo-5-chloroanisole in 100 ml of THF, 10 mL of n-BuLi (25.0 mmol, 2.5M in Hexane) was slowly added dropwise at -78°C. After stirring at the same temperature for 1 hour, 2-isoproxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2-isoproxy-4,4,5,5- 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 stirred at room temperature for an additional 24 hours. After completion of the reaction, 50 mL of a 10% aqueous HCl solution and 50 mL of H ₂ O were added, and the mixture was extracted three times with 80 mL of diethyl ether. The collected organic layers were dried over magnesium sulfate, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 5.83 g of Intermediate 9-1 (yield 92%). The produced compound was confirmed through LC-MS.

C ₁₃ H ₁₈ BClO ₃ : M ⁺ 268.1

Synthesis of Intermediate 9-2

Intermediate 9-1 5.90 g (22.0 mmol), 1,4-dibromochrysene 16.9 g (44.0 mmol), Pd(PPh ₃ ) ₄ (tetrakis(triphenylphosphine)palladium) 1.27g (1.1 mmol) and K ₂ CO ₃ 4.50 g (33 mmol) _{was dissolved in 200 ml of a THF/H 2} O (2/1 volume ratio) mixed solution, 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 the mixture was extracted three times with 60 ml of ethyl ether. The collected organic layers were dried over magnesium sulfate, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 6.30 g (yield 64%) of Intermediate 9-2. The produced compound was confirmed through 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 stirred at 85° C. for 12 hours. After the reaction solution was cooled to room temperature, it was extracted three times with 50 mL of water and 50 mL of diethyl ether. The collected organic layers were dried over magnesium sulfate, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 13.5 g of Intermediate 9-3 (yield 83%). The produced compound was confirmed through LC-MS.

C ₅₅ H ₅₂ N ₂ OSi ₂ M ⁺ 812.4

Synthesis of Intermediate 9-4

After dissolving 1.62 g (2.00 mmol) of Intermediate 9-3 in 10 ml of dichloromethane, 0.33 mL (3.5 mmol) of _{BBr 3 was slowly added dropwise at -78°C.} The reaction solution was raised to room temperature and stirred at room temperature for 24 hours. After the reaction was completed, 5 mL of MeOH and _{10 mL of H 2} O were added, and the mixture was extracted three times with 10 mL of dichloromethane. The collected organic layers were dried over magnesium sulfate, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 1.20 g of Intermediate 9-4 (yield 75%). The produced compound was confirmed through LC-MS.

C ₅₄ H ₅₀ N ₂ OSi ₂ : M ⁺ 798.3

Synthesis of compound 9

After dissolving 1.60 g (2.00 mmol) of Intermediate 9-4 in 10 ml of DMF, 0.48 g (6.0 mmol) of CuO was added dropwise at room temperature. The reaction solution was stirred at 140° C. for 48 hours. _{After completion of the reaction, 10 mL of H 2} O was added to the collected organic layer after filtering using Celite, and the mixture was extracted three times with 10 mL of ethyl acetate. The collected organic layers were dried over magnesium sulfate, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 1.39 g of compound 9 (yield 87%). The resulting compound was ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.31-8.29 (m, 1H), 8.20-8.18 (m, 1H), 7.96-7.94 (m, 1H), 7.84-7.74 (m, 5H), 7.65-7.56 (m, 4H), 7.32-7.24 (m, 5H), 6.96-6.94 (m, 1H), 6.90-6.81 (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 ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.23-8.21 (m, 1H), 8.09 (d, 1H), 8.02 (d, 1H), 7.81-7.77 (m, 1H), 7.63-7.48 (m, 5H), 7.12-7.02 (m, 9H) ), 6.76-6.74 (m, 1H), 6.66-6.61 (m, 4H), 6.50 (dd, 1H), 6.30-6.25 (m, 4H), 6.15-6.10 (m, 4H)

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 ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.62-8.60 (m, 1H), 8.51-8.47 (m, 3H), 8.38 (d, 1H), 8.20-8.16 (m, 2H), 7.97-7.85 (m, 1H), 7.82-7.79 (m , 1H), 7.71-7.49 (m, 14H), 7.43-7.39 (m, 2H), 7.16-7.01 (m, 6H), 6.85-6.77 (m, 4H), 6.66 (dd, 1H), 6.52-6.49 (m, 2H), 6.45-6.41 (m, 2H)

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 ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.31-8.29 (m, 1H), 8.20-8.18 (m, 1H), 7.94-7.90 (m, 2H), 7.84-7.79 (m, 2H), 7.72-7.67 (m, 3H), 7.63-7.54 (m, 5H), 7.48-7.40 (m, 4H), 7.32-7.30 (m, 1H), 7.23-7.14 (m, 4H), 6.92-6.90 (m, 1H) , 6.71 (dd, 1H)

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 ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.31-8.29 (m, 1H), 8.20-8.18 (m, 1H), 7.94-7.90 (m, 1H), 7.84-7.79 (m, 2H), 7.72-7.68 (m, 3H), 7.63-7.54 (m, 6H), 7.48-7.40 (m, 4H), 7.32-7.14 (m, 9H), 6.92-6.90 (m, 1H), 6.85-6.80 (m, 2H) , 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 ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.31-8.29 (m, 1H), 8.20-8.18 (m, 1H), 7.92-7.88 (m, 3H), 7.84-7.70 (m, 21H), 7.64-7.60 (m, 4H), 7.34-7.22 (m, 7H), 6.93-6.88 (m, 2H), 6.80-6.78 (m, 1H), 6.67 (dd, 1H), 6.55-6.52 (m, 2H), 6.45 -6.42 (m, 2H)

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 ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.47-8.42 (m, 2H), 8.30-8.28 (m, 1H), 8.20-8.15 (m, 2H), 7.94-7.89 (m, 1H), 7.72-7.65 (m, 4H), 7.55-7.50 (m, 2H), 7.38-7.30 (m, 5H), 7.25-7.20 (m, 2H), 7.08-7.05 (m, 1H), 6.99-6.92 (m, 2H) , 6.89-6.81 (m, 4H), 6.76 (dd, 1H), 6.67-6.63 (m, 2H)

M ⁺ calc. 654.24 found 654.25

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 ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.30-8.26 (m, 2H), 8.20-8.18 (m, 1H), 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 (dd, 1H), 6.92-6.86 (m, 4H), 6.75-6.65 (m, 5H), 1.61 (m, 12H), 0.21 (m , 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 ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.31-8.29 (m, 1H), 8.20-8.18 (m, 1H), 7.94-7.90 (m, 1H), 7.84-7.80 (m, 2H), 7.72-7.66 (m, 3H), 7.61-7.54 (m, 6H), 7.48-7.34 (m, 8H), 7.21 (dd, 1H), 7.13-7.04 (m, 4H), 6.93-6.86 (m, 3H), 6.73 -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 ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.31-8.29 (m, 1H), 8.20-8.18 (m, 1H), 7.84-7.80 (m, 2H), 7.73-7.70 (m, 4H), 7.64-7.40 (m, 22H), 7.32-7.20 (m, 5H), 7.11-7.06 (m, 2H), 6.87-6.81 (m, 3H), 6.73-6.70 (m, 1H), 6.62-6.56 (m, 2H)

M ⁺ calc. 984.34 found 984.35

Synthesis Example 11: Synthesis of compound 31

Compound 31 was synthesized using the same method as for the synthesis of compound 9, except that in the synthesis of intermediate 9-3, intermediate 11-A and then intermediate 31-A were used instead of intermediate 9-A. did. The resulting compound was ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.31-8.29 (m, 1H), 8.20-8.18 (m, 1H), 7.94-7.90 (m, 1H), 7.84-7.82 (m, 1H), 7.73-7.71 (m, 1H), 7.63-7.40 (m, 13H), 7.21-6.94 (m, 10H), 6.82-6.80 (m, 1H), 6.75-6.71 (m, 3H), 6.51 (dd, 1H), 6.43 -6.35 (m, 4H)

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 using the same method as for the synthesis of compound 9, except that in the synthesis of intermediate 9-3, intermediate 32-A and then intermediate 31-A were used instead of intermediate 9-A. did. The resulting compound was ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.32-8.30 (m, 1H), 8.20-8.18 (m, 1H), 7.72-7.70 (m, 2H), 7.66-7.40 (m, 20H), 7.21-6.96 (m, 9H), 6.92-6.90 (m, 1H), 6.85-6.78 (m, 3H), 6.61 (dd, 1H), 6.49-6.46 (m, 2H), 6.40-6.36 (m, 2H)

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 using the same method as for the synthesis of compound 9, except that in the synthesis of intermediate 9-3, intermediate 11-A and then intermediate 9-A were used instead of intermediate 9-A. did. The resulting compound was ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.31-8.29 (m, 1H), 8.20-8.18 (m, 1H), 7.94-7.90 (m, 1H), 7.84-7.82 (m, 1H), 7.72-7.70 (m, 1H), 7.63-7.52 (m, 6H), 7.48-7.36 (m, 4H), 7.21-7.14 (m, 7H), 6.96-6.94 (m, 1H), 6.90-6.82 (m, 4H) , 6.73 (dd, 1H), 6.67-6.62 (m, 2H), 6.53-6.50 (m, 2H), 0.24 (m, 9H)

M ⁺ calc. 814.30 found 814.31

Synthesis Example 14: Synthesis of compound 38

Compound 38 was synthesized using the same method as for the synthesis of compound 9, except that in the synthesis of intermediate 9-3, intermediate 38-A and then intermediate 9-A were used instead of intermediate 9-A. did. The resulting compound was ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.30-8.28 (m, 1H), 8.23-8.21 (m, 1H), 8.20-8.18 (m, 1H), 7.96-7.89 (m, 2H), 7.82-7.80 (m, 1H), 7.72-7.70 (m, 1H), 7.65-7.40 (m, 9H), 7.40-7.36 (m, 2H), 7.22-7.13 (m, 5H), 7.01-6.95 (m, 2H) , 6.91-6.81 (m, 4H), 6.73 (dd, 1H), 6.57-6.54 (m, 2H), 6.45-6.41 (m, 2H), 0.24 (m, 9H)

M ⁺ calc. 824.32 found 824.33

Synthesis Example 15: Synthesis of compound 48

Compound 48 was synthesized using the same method as for the synthesis of compound 9, except that in the synthesis of intermediate 9-3, intermediate 48-A and then intermediate 11-A were used instead of intermediate 9-A. did. The resulting compound was ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.31-8.29 (m, 1H), 8.20-8.18 (m, 1H), 7.84-7.82 (m, 1H), 7.72-7.53 (m, 11H), 7.48-7.40 (m, 4H), 7.28-7.04 (m, 10H), 6.96-6.94 (m, 1H), 6.82-6.80 (m, 1H), 6.75-6.70 (m, 2H), 6.61 (dd, 1H), 6.48 -6.44 (m, 2H), 6.27-6.25 (m, 2H)

M ⁺ calc. 818.29 found 818.30

Synthesis Example 16: Synthesis of compound 49

Compound 49 was synthesized using the same method as for the synthesis of compound 9, except that in the synthesis of intermediate 9-3, intermediate 14-A and then intermediate 11-A were used instead of intermediate 9-A. did. The resulting compound was ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.32-8.30 (m, 1H), 8.20-8.18 (m, 1H), 7.84-7.82 (m, 1H), 7.70-7.40 (m, 21H), 7.22-7.04 (m, 8H), 6.92-6.90 (m, 1H), 6.85-6.78 (m, 2H), 6.70 (dd, 1H), 6.56-6.53 (m, 2H), 6.35-6.32 (m, 2H)

M ⁺ calc. 912.32 found 912.33

Synthesis Example 17: Synthesis of compound 50

Compound 50 was synthesized using the same method as for the synthesis of compound 9, except that in the synthesis of intermediate 9-3, intermediate 50-A and then intermediate 11-A were used instead of intermediate 9-A. did. The resulting compound was confirmed by 1H NMR (CDCl3, 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.32-8.30 (m, 1H), 8.20-8.18 (m, 1H), 7.84-7.75 (m, 3H), 7.72-7.67 (m, 3H), 7.61-7.54 (m, 10H), 7.49-7.40 (m, 5H), 7.29-7.00 (m, 11H), 6.92-6.90 (m, 1H), 6.83 (t, 1H), 6.71 (dd, 1H), 6.66-6.63 (m, 2H)

M ⁺ calc. 908.30 found 908.31

Synthesis Example 18: Synthesis of compound 57

Compound 57 was synthesized using the same method as for the synthesis of compound 9, except that in the synthesis of intermediate 9-3, intermediate 1-A and then intermediate 50-A were used instead of intermediate 9-A. did. The resulting compound was ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.30-8.28 (m, 1H), 8.10-8.08 (m, 1H), 7.84-7.79 (m, 2H), 7.72-7.70 (m, 3H), 7.63-7.54 (m, 9H), 7.49-7.40 (m, 4H), 7.20-6.92 (m, 11H), 6.85-6.81 (m, 2H), 6.74-6.72 (m, 1H), 6.61 (t, 1H), 6.52 -6.48 (m, 2H)

M ⁺ calc. 818.29 found 818.30

Synthesis Example 19: Synthesis of compound 60

Compound 60 was synthesized using the same method as for the synthesis of compound 9, except that in the synthesis of intermediate 9-3, intermediate 48-A and then intermediate 50-A were used instead of intermediate 9-A. did. The resulting compound was confirmed by 1H NMR (CDCl3, 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.33-8.29 (m, 1H), 8.10-8.08 (m, 1H), 7.84-7.82 (m, 1H), 7.72-7.70 (m, 1H), 7.65-7.50 (m, 14H), 7.47-7.40 (m, 5H), 7.20-7.10 (m, 5H), 7.05-6.90 (m, 7H), 6.78-6.76 (m, 1H), 6.72 (t, 1H), 6.64 -6.62 (m, 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 using the same method as for the synthesis of compound 9, except that in the synthesis of Intermediate 9-3, Intermediate 38-A and then Intermediate 50-A were used instead of Intermediate 9-A. did. The resulting compound was confirmed by 1H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.30-8.28 (m, 1H), 8.23-8.21 (m, 1H), 8.10-8.08 (m, 1H), 7.99-7.89 (m, 2H), 7.84-7.76 (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, 1H), 6.80 (t, 1H), 6.52 -6.48 (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 using the same method as for the synthesis of compound 9, except that in the synthesis of intermediate 9-3, instead of intermediate 9-A, intermediate 14-A and then intermediate 1-A were used. did. The resulting compound was confirmed by 1H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.32-8.30 (m, 1H), 8.22-8.20 (m, 1H), 7.72-7.49 (m, 16H), 7.43-7.40 (m, 1H), 7.32-7.22 (m, 8H), 7.16-7.14 (m, 1H), 7.06-6.98 (m, 3H), 6.82-6.80 (m, 1H), 6.70-6.62 (m, 4H), 6.52-6.48 (m, 2H)

M ⁺ calc. 822.30 found 822.31

Synthesis Example 22: Synthesis of compound 73

In the synthesis method of Intermediate 9-3 of Synthesis Example 1, instead of Intermediate 9-A, Intermediate 32-A was first used, and then Intermediate 73-A was used. The same method as for the synthesis of Compound 9 was followed. Compound 73 was synthesized using The resulting compound was ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.32-8.30 (m, 1H), 8.20-8.18 (m, 1H), 7.72-7.49 (m, 16H), 7.43-7.40 (m, 1H), 7.31-7.29 (m, 2H), 7.22-7.20 (m, 6H), 7.13-7.08 (m, 2H), 6.96-6.94 (m, 1H), 6.85 (dd, 1H), 6.72-6.68 (m, 2H), 6.62 -6.58 (m, 2H), 2.25 (s, 6H)

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

Synthesis Example 23: Synthesis of compound 75

In the synthesis method of Intermediate 9-3 of Synthesis Example 1, instead of Intermediate 9-A, Intermediate 48-A was first used and then Intermediate 75-A was used, except that the same method as for the synthesis of Compound 9 was used. Compound 75 was synthesized using The resulting compound was ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.33-8.30 (m, 1H), 8.20-8.18 (m, 1H), 7.78-7.76 (m, 1H), 7.68-7.52 (m, 10H), 7.47-7.44 (m, 2H), 7.35-7.30 (m, 1H), 7.19-6.98 (m, 10H), 6.87-6.84 (m, 2H), 6.72 -6.60 (m, 3H), 6.53-6.51 (m, 2H) , 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

In the synthesis method of Intermediate 9-3 of Synthesis Example 1, instead of Intermediate 9-A, Intermediate 11-A was first used and then Intermediate 75-A was used, except that the same method as the synthesis of Compound 9 was used. Compound 77 was synthesized using The resulting compound was ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.31-8.29 (m, 1H), 8.20-8.18 (m, 1H), 7.94-7.90 (m, 1H), 7.84-7.54 (m, 10H), 7.45-7.40 (m, 2H), 7.35-7.30 (m, 1H), 7.24-7.04 (m, 9H), 6.97 (dd, 1H), 6.91 -6.89 (m, 1H), 6.76-6.70 (m, 2H), 6.63 -6.61 (m, 2H), 6.43-6.41 (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

In the synthesis method of Intermediate 9-3 of Synthesis Example 1, instead of Intermediate 9-A, Intermediate 79-A was first used, and then Intermediate 75-A was used, except that the same method as the synthesis of Compound 9 was used. Compound 79 was synthesized using The resulting compound was ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.30-8.28 (m, 1H), 8.20-8.18 (m, 1H), 7.81-7.77 (m, 2H), 7.65 (dd, 1H), 7.63-754 (m , 5H), 7.36-7.33 (m, 1H), 7.25-7.21 (m, 2H), 7.14-7.02 (m, 7H), 6.86 (dd, 1H), 6.77-6.75 (m, 1H), 6.65-6.62 (m, 2H), 6.53-6.50 (m, 2H), 6.46-6.42 (m, 2H), 6.33-6.31 (m, 2H), 6.22-6.19 (m, 2H), 1.63 (s, 6H), 1.50 (s, 9H)

M ⁺ calc. 824.38 found 824.39

Synthesis Example 26: Synthesis of compound 84

In the synthesis method of Intermediate 9-3 of Synthesis Example 1, instead of Intermediate 9-A, Intermediate 11-A was first used, and then Intermediate 84-A was used, except that the same method as for the synthesis of Compound 9 was used. Compound 84 was synthesized using The resulting compound was confirmed by 1H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.31-8.29 (m, 1H), 8.20-8.18 (m, 1H), 8.07-8.05 (m, 1H), 7.94-7.92 (m, 1H), 7.84-7.82 (m, 1H), 7.72-7.70 (m, 1H), 7.63-7.40 (m, 14H), 7.31-7.26 (m, 2H), 7.16 -6.94 (m, 7H), 6.81-6.75 (m, 2H) , 6.63-6.57 (m, 2H), 6.49-6.47 (m, 1H), 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

In the synthesis of Intermediate 9-2 of Synthesis Example 1, the same method as for the synthesis of Intermediate 9-2 was used except that Intermediate 86-A was used instead of Intermediate 9-1 and Intermediate 9-2 was used instead of dibromonaphthalene. Intermediate 86-1 was synthesized using The produced compound was confirmed through LC-MS.

C ₄₃ H ₃₀ ClNO: M ⁺ 611.2

Synthesis of Intermediate 86-2

In the synthesis of Intermediate 9-3 of Synthesis Example 1, 1-A instead of Compound 9-A and Intermediate 86-1 instead of Intermediate 9-2 were used in the same manner as in the synthesis of Intermediate 9-3. Thus, intermediate 86-2 was synthesized. The produced compound was confirmed through LC-MS.

C ₅₅ H ₄₀ N ₂ O: M ⁺ 744.3

Synthesis of Intermediate 86-3

Intermediate 86-3 was synthesized using the same method as the synthesis method of Intermediate 9-4, except that Intermediate 86-2 was used instead of Intermediate 9-3 in the synthesis of Intermediate 9-4 of Synthesis Example 1. . The produced compound was confirmed through LC-MS.

C ₅₄ H ₃₈ N ₂ O: M ⁺ 730.3

Synthesis of compound 86

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

■■■8.60-8.58 (m, 1H), 8.39-8.37 (m, 1H), 8.32-8.30 (m, 1H), 8.26-8.24 (m, 1H), 7.79-7.77 (m, 1H), 7.67- 7.56 (m, 3H), 7.53-7.49 (m, 2H), 7.18-7.03 (m, 10H), 6.96-6.93 (m, 2H), 6.86 -6.84 (m, 1H), 6.76-6.72 (m, 4H) ), 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 instead of Intermediate 1-A in the synthesis of Intermediate 86-2 of Synthesis Example 27. The resulting compound was ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.39-8.37 (m, 1H), 8.32-8.30 (m, 1H), 8.26-8.24 (m, 1H), 7.84-7.77 (m, 2H), 7.72-7.62 (m, 4H), 7.53-7.40 (m, 5H), 7.28-7.13 (m, 12H), 6.92-6.90 (m, 1H), 6.85-6.81 (m, 3H), 6.71-6.69 (m, 1H) , 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 ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.39-8.37 (m, 1H), 8.34-8.32 (m, 1H), 8.26-8.24 (m, 1H), 7.84-7.79 (m, 2H), 7.72-7.40 (m, 14H), 7.30-7.02 (m, 14H), 6.95-6.93 (m, 1H), 6.82-6.79 (m, 2H), 6.69 (dd, 1H), 6.56-6.54 (m, 2H), 6.39 -6.37 (m, 2H)

M ⁺ calc. 894.32 found 894.32

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 instead of Intermediate 86-A. The resulting compound was ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.37-8.35 (m, 1H), 8.24-8.22 (m, 1H), 8.16-8.12 (m, 1H), 7.79-7.77 (m, 1H), 7.72-7.50 (m, 15H), 7.44-7.42 (m, 1H), 7.28-7.14 (m, 9H), 7.10-7.05 (m, 2H), 6.97 -6.95 (m, 1H), 6.86-6.82 (m, 3H) , 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 50-A was used instead of Intermediate 1-A. The resulting compound was ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.39-8.37 (m, 1H), 8.24-8.22 (m, 1H), 8.16-8.12 (m, 1H), 7.84-7.79 (m, 2H), 7.72-7.40 (m, 14H), 7.30-7.02 (m, 14H), 6.88-7.82 (m, 2H), 6.74-6.72 (m, 1H), 6.62 (dd, 1H), 6.54-6.50 (m, 4H)

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 ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.39-8.37 (m, 1H), 8.24-8.22 (m, 1H), 8.16-8.14 (m, 1H), 7.79-7.77 (m, 1H), 7.67-7.56 (m, 3H), 7.53-7.49 (m, 2H), 7.40-7.36 (m, 2H), 7.29-7.13 (m, 7H), 7.06-7.02 (m, 2H), 6.96-6.94 (m, 1H) , 6.84-6.75 (m, 4H), 6.66-6.59 (m, 3H), 6.40-6.34 (m, 4H), 6.30-6.26 (m, 2H), 0.25 (m, 9H)

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 instead of Intermediate 86-A and Intermediate 31-A was used instead of Intermediate 1-A. ^It was confirmed through 1 H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.39-8.37 (m, 1H), 8.24-8.22 (m, 1H), 8.16-8.14 (m, 1H), 7.79-7.77 (m, 1H), 7.67-7.44 (m, 15H), 7.31-7.09 (m, 14H), 6.95-6.90 (m, 2H), 6.85-6.80 (m, 3H), 6.71 (dd, 1H), 6.58-6.54 (m, 2H), 6.50 -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 instead of Intermediate 86-A and Intermediate 121-B was used instead of Intermediate 1-A. ^It was confirmed through 1 H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.39-8.37 (m, 1H), 8.24-8.22 (m, 1H), 8.16-8.14 (m, 1H), 7.79-7.77 (m, 1H), 7.67-7.58 (m, 3H), 7.53-7.49 (m, 2H), 7.38-7.30 (m, 2H), 7.17-7.13 (m, 2H), 6.99-6.97 (m, 1H), 6.82-6.80 (m, 1H)

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 instead of Intermediate 86-A and Intermediate 17-A was used instead of Intermediate 1-A. ^It was confirmed through 1 H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.60-8.58 (m, 1H), 8.39-8.37 (m, 1H), 8.24-8.22 (m, 1H), 8.16-8.14 (m, 1H), 7.84-7.40 (m, 11H), 7.28-7.08 (m, 9H), 6.90 -6.88 (m, 1H), 6.85-6.80 (m, 2H), 6.66-6.62 (m, 3H), 6.42 (dd, 1H), 6.35-6.32 (m, 2H), 6.25 -6.22 (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 in the synthesis of Intermediate 9-3, except that Intermediate 35-A was used instead of Intermediate 9-A in the synthesis of Intermediate 9-3 of Synthesis Example 1. The produced compound was confirmed through LC-MS.

C ₄₂ H ₂₄ ClNO ₂ : M+ 609.2

Synthesis of Intermediate 141-2

In the synthesis of Intermediate 9-2 of Synthesis Example 1, the same method as the synthesis of Intermediate 9-2 except that Intermediate 94-A was used instead of Intermediate 9-1 and Intermediate 141-1 was used instead of dibromonaphthalene. Intermediate 141-2 was synthesized using The produced compound was confirmed through LC-MS.

C67H46 N2O2: M+ 910.3

Synthesis of intermediate 141-3

Intermediate 141-3 was synthesized using the same method as the synthesis method of Intermediate 9-4, except that Intermediate 141-2 was used instead of Intermediate 9-3 in the synthesis of Intermediate 9-4 of Synthesis Example 1. . The produced compound was confirmed through LC-MS.

C66H44 N ₂ O ₂ : M+ 896.3

Synthesis of compound 141

Compound 141 was synthesized using the same method as in the synthesis of Compound 9, except that Intermediate 141-3 was used instead of Intermediate 9-4 in the synthesis of Compound 9 of Synthesis Example 1. The resulting compound was _{confirmed by 1H NMR (CDCl3} , 400 MHz) and MS/FAB.

δ=8.65-8.62 (m, 1H), 8.39-8.37 (m, 1H), 8.20-8.18 (m, 1H), 8.01-7.90 (m, 2H), 7.84-7.82 (m, 1H), 7.72-7.70 (m, 1H), 7.63 7.48 (m, 16H), 7.30-7.26 (m, 2H), 7.16-7.04 (m, 8H), 6.95-6.92 (m, 1H), 6.85-6.80 (m, 2H), 6.67-6.62 (m, 2H), 6.53-6.49 (m, 2H), 6.37-6.34 (m, 2H)

M+ calc. 894.32 found 894.33

Synthesis Example 37: Synthesis of compound 154

Compound 154 was synthesized in the same manner as in the synthesis of compound 86, except that Intermediate 154-A was used instead of Intermediate 86-A. ^It was confirmed through 1 H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.66-8.64 (m, 1H), 8.36-8.34 (m, 1H), 8.24-8.22 (m, 1H), 8.12-8.02 (m, 2H), 7.97-7.90 (m, 2H), 7.80-7.78 (m, 1H), 7.66 7.56 (m, 4H), 7.45-7.41 (m, 1H), 7.32-7.24 (m, 9H), 7.13-7.11 (m, 1H), 6.97 (dd, 1H), 6.87- 6.85 (m, 1H), 6.76-6.72 (m, 4H), 6.63 (dd, 1H), 6.50-6.42 (m, 8H)

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 instead of Intermediate 86-A. ^It was confirmed through 1 H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.66-8.64 (m, 1H), 8.32-8.30 (m, 1H), 8.15-8.13 (m, 1H), 8.06-8.04 (m, 1H), 7.94-7.91 (m, 1H), 7.88 (dd , 1H), 7.82 7.80 (m, 1H), 7.67-7.56 (m, 3H), 7.40-7.30 (m, 5H), 7.22-7.14 (m, 5H), 7.05-6.95 (m, 3H), 6.87- 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 instead of Intermediate 35-A and 157-A was used instead of Intermediate 94-A.

δ=8.60-8.58 (m, 1H), 8.30-8.28 (m, 1H), 8.20-8.18 (m, 1H), 7.97-7.86 (m, 2H), 7.82-7.78 (m, 2H), 7.65-7.54 (m, 5H), 7.48-7.44 (m, 2H), 7.35 (t, 1H), 7.26-7.19 (m, 10H), 7.08 (t, 1H), 6.85-6.81 (m, 4H), 6.70-6.62 (m, 4H), 6.52-6.46 (m, 4H)

M ⁺ calc. 818.29 found 818.29

Synthesis Example 40: Synthesis of compound 160

In the synthesis of Intermediate 9-2 of Synthesis Example 1, the same method as for the synthesis of Intermediate 9-2 was used, except that Intermediate 107-A was used instead of Intermediate 9-1 and Intermediate 9-2 was used instead of dibromonaphthalene. Intermediate 160-1 was synthesized using The produced compound was confirmed through LC-MS.

C ₆₇ H ₆₀ N ₂ OSi ₂ : M ⁺ 964.4

Synthesis of Intermediate 160-3

Intermediate 160-3 was synthesized using the same method as the synthesis method of Intermediate 9-4, except that Intermediate 160-1 was used instead of Intermediate 9-3 in the synthesis of Intermediate 9-4 of Synthesis Example 1. . The produced compound was confirmed through LC-MS.

C ₆₆ H ₅₈ N ₂ OSi ₂ : M ⁺ 950.4

Synthesis of compound 160

Compound 160 was synthesized using the same method as in the synthesis of Compound 9, except that Intermediate 160-3 was used instead of Intermediate 9-4 in the synthesis of Compound 9 of Synthesis Example 1. The resulting compound was ^{confirmed by 1} H NMR (CDCl ₃ , 400 MHz) and MS/FAB.

δ=8.56-8.54 (m, 1H), 8.39-8.37 (m, 1H), 8.24-8.22 (m, 1H), 8.16-8.14 (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 (m, 1H), 7.27-7.05 (m, 9H) , 6.85-6.82 (m, 2H), 6.76-6.65 (m, 4H), 6.52-6.46 (m, 4H), 0.24 (s, 18H)

M ⁺ calc. 948.39 found 948.40

Example 1

A 1200Å thick ITO glass substrate (made by Corning) was cut into a size of 50mm x 50mm x 0.7mm, ultrasonically cleaned using isopropyl alcohol and pure water for 5 minutes each, then irradiated with ultraviolet rays for 30 minutes and exposed to ozone. After exposure and cleaning, the ITO glass substrate was installed in a vacuum deposition apparatus.

After depositing HT13 on the anode to form a hole injection layer having a thickness of 600 Å, depositing HT3 on the hole injection layer to form a hole transport layer having a thickness of 300 Å, ADN and the compound 9 on the hole transport layer A light emitting layer having a thickness of 300 Å was formed by co-deposition at a weight ratio of 98:2.

_{Alq 3} was deposited on the light emitting layer to form an electron transport layer of 300 Å. An organic light emitting device was manufactured by depositing LiF on the electron transport layer to form an electron injection layer with a thickness of 10 Å, and then vacuum-depositing Al on the electron injection layer to form a cathode with a thickness of 3000 Å.

Example 2

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 11 was used instead of Compound 9 when forming the emission layer.

Example 3

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 31 was used instead of Compound 9 when forming the emission layer.

Example 4

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 32 was used instead of Compound 9 when the emission layer was formed.

Example 5

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 73 was used instead of Compound 9 when forming the emission layer.

Example 6

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 86 was used instead of Compound 9 when forming the emission layer.

Example 7

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 113 was used instead of Compound 9 when forming the emission layer.

Example 8

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 156 was used instead of Compound 9 when forming the emission layer.

Comparative Example 1

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound A was used instead of Compound 9 when the emission layer was formed.

<Compound A>

Comparative Example 2

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound B was used instead of Compound 9 when the emission layer was formed.

<Compound B>

Example 9

An organic light emitting diode was manufactured in the same manner as in Example 1, except that compound H109 was used instead of ADN when forming the light emitting layer.

Example 10

An organic light emitting diode was manufactured in the same manner as in Example 9, except that Compound 11 was used instead of Compound 9 when the emission layer was formed.

Example 11

An organic light emitting diode was manufactured in the same manner as in Example 9, except that Compound 31 was used instead of Compound 9 when the emission layer was formed.

Example 12

An organic light emitting diode was manufactured in the same manner as in Example 9, except that Compound 50 was used instead of Compound 9 when the emission layer was formed.

Example 13

An organic light emitting diode was manufactured in the same manner as in Example 9, except that Compound 86 was used instead of Compound 9 when the emission layer was formed.

Example 14

An organic light emitting diode was manufactured in the same manner as in Example 9, except that Compound 156 was used instead of Compound 9 when forming the emission layer.

Example 15

An organic light emitting diode was manufactured in the same manner as in Example 1, except that compound H152 was used instead of ADN when forming the light emitting layer.

Example 16

An organic light emitting diode was manufactured in the same manner as in Example 15, except that Compound 11 was used instead of Compound 9 when the emission layer was formed.

Example 17

An organic light emitting diode was manufactured in the same manner as in Example 15, except that Compound 31 was used instead of Compound 9 when the emission layer was formed.

Example 18

An organic light emitting diode was manufactured in the same manner as in Example 15, except that Compound 50 was used instead of Compound 9 when forming the emission layer.

Example 19

An organic light emitting diode was manufactured in the same manner as in Example 15, except that Compound 73 was used instead of Compound 9 when the emission layer was formed.

Example 20

An organic light emitting diode was manufactured in the same manner as in Example 15, except that Compound 86 was used instead of Compound 9 when the emission layer was formed.

Example 21

An organic light emitting diode was manufactured in the same manner as in Example 15, except that Compound 113 was used instead of Compound 9 when forming the emission layer.

Example 22

An organic light emitting diode was manufactured in the same manner as in Example 1, except that compound H167 was used instead of ADN when forming the emission layer.

Example 23

An organic light emitting diode was manufactured in the same manner as in Example 22, except that Compound 11 was used instead of Compound 9 when the emission layer was formed.

Example 24

An organic light emitting diode was manufactured in the same manner as in Example 22, except that Compound 31 was used instead of Compound 9 when forming the emission layer.

Example 25

An organic light emitting diode was manufactured in the same manner as in Example 22, except that Compound 50 was used instead of Compound 9 when the emission layer was formed.

Example 26

An organic light emitting diode was manufactured in the same manner as in Example 22, except that Compound 73 was used instead of Compound 9 when the emission layer was formed.

Example 27

An organic light emitting diode was manufactured in the same manner as in Example 22, except that Compound 86 was used instead of Compound 9 when the emission layer was formed.

Example 28

An organic light emitting diode was manufactured in the same manner as in Example 1, except that compound H204 was used instead of ADN when forming the light emitting layer.

Example 29

An organic light emitting diode was manufactured in the same manner as in Example 28, except that Compound 11 was used instead of Compound 9 when the emission layer was formed.

Example 30

An organic light emitting diode was manufactured in the same manner as in Example 28, except that Compound 56 was used instead of Compound 9 when the emission layer was formed.

Example 31

An organic light emitting device was manufactured in the same manner as in Example 1, except that compound H208 was used instead of ADN when forming the light emitting layer.

Example 32

An organic light emitting diode was manufactured in the same manner as in Example 31, except that Compound 11 was used instead of Compound 9 when the emission layer was formed.

Example 33

An organic light emitting diode was manufactured in the same manner as in Example 31, except that Compound 56 was used instead of Compound 9 when the emission layer was formed.

Comparative Example 3

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound H109 was used instead of ADN and Compound A was used instead of Compound 9 when the light emitting layer was formed.

Evaluation Example 1

The driving voltage, current density, luminance, efficiency, and half-life of the organic light emitting diodes manufactured in Examples 1 to 27 and Comparative Examples 1 and 3 were measured using a Kethley SMU 236 and a luminance meter PR650, and are shown in Tables 1 and 2 It was. The half-life is a measure of the time it takes for the luminance to reach 50% of the initial luminance after driving the organic light emitting diode.

Emissive layer dopant drive voltage
(V) electric current
density
(mA/cm ² ) luminance
(cd/m ² ) efficiency
(cd/A) luminous color half life
(hr@
100mA/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 351hr 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 342hr 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 drive voltage
(V) current density
(㎃/㎠) luminance
(cd/m2) efficiency
(cd/A) luminous color half life
(hr @100㎃/㎠) 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 461hr Example 13 compound H109 compound 86 6.62 50 3,335 6.87 blue 458hr 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 495hrs 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 486hr 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 413hr 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 416hr 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 Tables 1 and 2, it can be seen 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-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 are each independently, 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 Alkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted A substituted or unsubstituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic group ) is selected from;
a11 to a13 are each independently selected from 0, 1, 2 and 3;
R ₁₁ to R ₁₆ are each independently, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group , substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent selected from a non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;
n11 to n13 are each independently selected from 0, 1 and 2, wherein the sum of n11, n12 and n13 is selected from 2, 3, 4, 5 and 6;
R ₁₇ to R ₁₉ are each independently hydrogen, deuterium, F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group Or a salt thereof, 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, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or an 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- selected from a condensed aromatic heteropolycyclic group and -Si(Q ₁ )(Q ₂ )(Q ₃ );
said substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ Alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ hetero Cycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C _{At least one} substituent of the 6 -C ₆₀ arylthio group, the substituted C 1 -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted or unsubstituted monovalent non-aromatic condensed polycyclic group is ,
Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁₁ ) (Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q _{15 ), C 1} -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, substituted with at least one of -B(Q ₁₆ )(Q _{17 )} , C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;
C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl an oxy group, 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 condensed heteropolycyclic group;
Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B(Q ₂₆ )(Q _{27 ), C 3} -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocyclo, substituted with at least one of -B(Q 26 )(Q 27 ). alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is non- -Aromatic heterocondensed polycyclic group; and
-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) and -B(Q ₃₆ )(Q ₃₇ ); is selected from;
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 group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ an aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group. According to claim 1,
L ₁₁ to L ₁₃ are each independently, phenylene group, naphthylene group, fluorenylene group, phenanthrenylene group, anthracenylene group, triphenylenylene group, pyrrolylene group, thiophenylene group, furanylene group, pyridinyl Ren group, pyrazinylene group, pyrimidinylene group, indolylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinolinyl group a ren group, a carbazolylene group, a phenanthridinylene group, a benzoimidazolylene group, a benzofuranylene group, a benzothiophenylene group, a triazolylene group, a dibenzofuranylene group and a dibenzothiophenylene group; and
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 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 ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, Anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and 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 furanylene group, a pyridinyl group substituted with at least one of a triazinyl group Ren group, pyrazinylene group, pyrimidinylene group, indolylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinolinyl group a ren group, a carbazolylene group, a phenanthridinylene group, a benzoimidazolylene group, a benzofuranylene group, a benzothiophenylene group, a triazolylene group, a dibenzofuranylene group and a dibenzothiophenylene group; selected from among, amine-based compounds. According to claim 1,
L ₁₁ to L ₁₃ are each independently an amine compound represented by any one of the following Chemical Formulas 3-1 to 3-31:

In 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 are each independently 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 carboxyl group, or A salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, Dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoc selected from 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, independently of each other, binding sites with neighboring atoms. According to claim 1,
a11 to a13 are each independently selected from 0 and 1, an amine compound. According to claim 1,
R ₁₁ to R ₁₆ are each independently, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrrolyl group, thiophenyl group, furanyl group, pyridinyl group, pyrazinyl group, pyri Midinyl group, quinolinyl group, isoquinolinyl group, carbazolyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzo a furanyl group, a benzothiophenyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group and a dibenzosilolyl group;
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 carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof Salt, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, tria A phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrrolyl group, a thiophenyl group, substituted with at least one of a zinyl group and -Si(Q ₃₃ )(Q ₃₄ )(Q _{35 )} , furanyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, quinolinyl group, isoquinolinyl group, carbazolyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzofuranyl group, benzothiophenyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group and dibenzosilolyl group; and
Deuterium, -F, -Cl, -Br, -I, substituted with at least one of a cyano group and a nitro group, substituted with at least one of a C ₁ -C ₂₀ alkyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl 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, quinoxalinyl group , quinazolinyl group, cinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzofuranyl group, benzothiophenyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group and dibenzo silolyl; is selected from;
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, an amine-based compound. According to claim 1,
R ₁₁ to R ₁₆ are each independently selected from the following formulas 5-1 to 5-33:

In 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 are each independently 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 carboxyl group, or A salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, -CD ₃ , -CF ₃ , a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-flu Orenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group , isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, triazinyl group and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ); is selected from;
Q ₃₃ to Q ₃₅ are each independently selected from a methyl group, an ethyl group, a tert-butyl group, a phenyl group, and a naphthyl group; is selected from;
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 a binding site with a neighboring atom. According to claim 1,
n11 to n13 are each independently selected from 0 and 1, an amine compound. According to claim 1,
R ₁₇ to R ₁₉ are hydrogen, an amine compound. According to claim 1,
An amine-based compound represented by the following formula 1-1:
<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. According to claim 1,
An amine-based compound represented by the following formula 1-1A:
<Formula 1-1A>

In 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. According to claim 1,
The amine-based compound is any one of the following compounds 1 to 162, an amine-based compound:

a first electrode; a second electrode; and an organic layer including a light emitting layer interposed between the first electrode and the second electrode, wherein the organic layer includes at least one amine-based compound according to any one of claims 1 to 11. 13. The method of claim 12,
An organic light emitting device in which the light emitting layer further includes a host, and the amine-based compound is a dopant. 14. The method of claim 13,
The host is an anthracene-based compound represented by the following formula (2), an organic light emitting device:
<Formula 2>

In Formula 2,
L ₂₁ is 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, a substituted or unsubstituted A substituted C ₁ -C ₁₀ heterocycloalkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ arylene group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic group selected from a condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group;
a21 is selected from 0, 1, 2 and 3;
R ₂₁ to R ₂₃ are each independently 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, a substituted or unsubstituted A substituted 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 ratio -aromatic heterocondensed polycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ) and -B(Q ₆ )(Q ₇ );
b21 to b23 are each independently selected from 1, 2, 3, 4, 5 and 6;
n21 is selected from 1, 2 and 3;
said substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ Alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ At least one substituent of the arylthio group, the substituted C ₁ -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group is,
Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁₁ ) (Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q _{15 ), C 1} -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, substituted with at least one of -B(Q ₁₆ )(Q _{17 )} , C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;
C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl an oxy group, 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 condensed heteropolycyclic group;
Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B(Q ₂₆ )(Q _{27 ), C 3} -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocyclo, substituted with at least one of -B(Q 26 )(Q 27 ). alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is non- -Aromatic heterocondensed polycyclic group; and
-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) and -B(Q ₃₆ )(Q ₃₇ ); is selected from;
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 group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ an aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group. 15. The method of claim 14,
L ₂₁ is selected from Formulas 3-1 to 3-8 and 3-22 to 3-29, an organic light emitting device:

In 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 are each independently 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 carboxyl group, or A salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, Dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoc selected from 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, independently of each other, binding sites with neighboring atoms. 15. The method of claim 14,
R ₂₁ and R ₂₂ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, -N(Ph) ₂ , -Si(CH ₃ ) ₃ , -Si(Ph) ₃ and an organic light emitting device selected from the following Chemical Formulas 5-1 to 5-9 and 5-33:

In 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 are each independently 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 carboxyl group, or A salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, -CD ₃ , -CF ₃ , a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-flu Orenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group , isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, triazinyl group, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ); and
Q ₃₃ to Q ₃₅ are each independently selected from a methyl group, an ethyl group, a ter-butyl group, a phenyl group and a naphthyl group; is selected from;
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 a binding site with a neighboring atom. 15. The method of claim 14,
R ₂₃ is selected from hydrogen, a methyl group, an ethyl group, a tert-butyl group, a methoxy group, an ethoxy group, a ter-butoxy group, -Si(CH ₃ ) ₃ , a phenyl group, and a naphthyl group. 15. The method of claim 14,
n21 is 1; an organic light emitting device. 15. The method of claim 14,
The anthracene-based compound is an organic light emitting device represented by any one of the following Chemical Formulas 2-1 and 2-2:
<Formula 2-1>

<Formula 2-2>

In Formulas 2-1 and 2-2,
L ₂₁ , a21 , R ₂₁ to R ₂₃ and b21 to b23 are as defined in claim 14 . 15. The method of claim 14,
The anthracene-based compound is an organic light emitting device selected from the following compounds H101 to H188 and H201 to H218:

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