KR102429869B1 - Organic light emitting device including the same - Google Patents

Abstract

An organic light emitting device is disclosed.

Description

Organic light emitting device including the same

An organic light emitting device is provided.

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

According to an example, the organic light emitting device may include an anode, a cathode, and an organic layer interposed between the anode and the cathode and including a light emitting layer. A hole transport region may be provided between the anode and the emission layer, and an electron transport region may be provided between the emission layer and the cathode. Holes injected from the anode move to the emission layer via the hole transport region, and electrons injected from the cathode move to the emission layer via the electron transport region. The 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.

To provide an organic light emitting device employing a novel compound.

According to one aspect,

a first electrode;

a second electrode opposite to the first electrode; and

an organic layer disposed between the first electrode and the second electrode and including a light emitting layer;

The organic layer includes a first material and a second material,

The first material includes an organometallic compound represented by the following formula (1),

The second material has the following Chemical Formulas 11, 21A, 21B, 21C, 31A, 31B, 41, 51A, 51B, 61, 71-1 to 71-12, 81, 91A, 91B, 91C, 91D, 101, 111, 121 , 131A, 131B, and an organic light emitting device including at least one of the compounds represented by 141 is provided.

The organic light emitting diode may have low driving voltage, high efficiency and long lifespan, and excellent color purity.

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

1 is a schematic cross-sectional view of an organic light emitting device 10 according to an embodiment of the present invention. Hereinafter, a structure and a manufacturing method of an organic light emitting device according to an embodiment of the present invention will be described with reference to FIG. 1 . The organic light emitting device 10 has a structure in which a first electrode 11 , an organic layer 15 , and a second electrode 19 are sequentially stacked.

A substrate may be additionally disposed below the first electrode 11 or above the second electrode 19 . As the substrate, a substrate used in a conventional organic light emitting device may be used, and a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, handling easiness and waterproofness may be used.

The first electrode 11 may be formed by, for example, providing a material for the first electrode on a substrate using a deposition method or a sputtering method. The first electrode 11 may be 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 11 may be a reflective electrode, a transflective electrode, or a transmissive electrode. As a material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), or the like may be used. Alternatively, a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) may be used. .

The first electrode 11 may have a single layer or a multilayer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO/Ag/ITO, but is not limited thereto.

An organic layer 15 is disposed on the first electrode 11 . The organic layer 15 includes a light emitting layer.

The organic layer 15 includes a first material and a second material.

The first material includes an organometallic compound represented by the following formula (1),

The second material has the following Chemical Formulas 11, 21A, 21B, 21C, 31A, 31B, 41, 51A, 51B, 61, 71-1 to 71-12, 81, 91A, 91B, 91C, 91D, 101, 111, 121 , 131A, 131B, and at least one of the compounds represented by 141.

Formula 1

<Formula 1>

In Formula 1, R ₁₁ to R ₁₈ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, A hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, 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 monovalent non-aromatic condensed heteropolycyclic group, -X ₁ (R ₁ )(R ₂ )(R ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₃ )(Q ₄ ) and - P(=O)(Q ₅ )(Q ₆ ), wherein at least one of R ₁₁ to R ₁₈ may be represented by -X ₁ (R ₁ )(R ₂ )(R ₃ ).

For example, in Formula 1, R ₁₁ to R ₁₈ are each independently

Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof , phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, C ₃ -C ₁₀ cyclo Alkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₁₄ aryl group, C ₁ -C ₁₄ heteroaryl group, monovalent ratio - a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of a condensed aromatic polycyclic group and a monovalent non-aromatic condensed heteropolycyclic 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 ₁₄ aryl group, C ₁ -C ₁₄ hetero an aryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₁₀ cyclo Alkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₁₄ aryl group, C ₁ -C ₁₄ heteroaryl group, monovalent ratio -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 ₁₄ aryl group, C ₁ -C ₁₄ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group; and

-Si(R ₁ )(R ₂ )(R ₃ ), -Ge(R ₄ )(R ₅ )(R ₆ ), -N(Q ₁ )(Q ₂ ), -B(Q ₃ )(Q ₄ ) ) and -P(=O)(Q ₅ )(Q ₆ ); can be selected from

For example, in Formula 1, R ₁₁ to R ₁₈ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, -SF ₅ , a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₁₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cycloox substituted with at least one of a tyl group, an adamantanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group, C ₁ - C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorine group Nyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, iso Thiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolyl group Nyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl 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, imidazopyridinyl group and an imidazopyrimidinyl group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohex Sil group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, Anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group , quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzoxazolyl group , triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl group substituted with at least one of a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group (adamantanyl), a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group , naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl 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, fu Linyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl 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, di a benzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; and

-X ₁ (R ₁ )(R ₂ )(R ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₃ )(Q ₄ ), and -P(=O)(Q ₅ )(Q ₆ ); selected from among

At least one of R ₁₁ to R ₁₈ is represented by -X ₁ (R ₁ )(R ₂ )(R ₃ ),

Q ₁ to Q ₆ are each independently,

C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, triazinyl group and carbazolyl group;

a phenyl group and a naphthyl group substituted with at least one of a C ₁ -C ₂₀ alkyl group, a phenyl group, and a naphthyl group; can be selected from

According to another embodiment, in Formula 1, R ₁₁ to R ₁₈ are each independently

Hydrogen, deuterium, -F, cyano group, nitro group, -SF ₅ , methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n -pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group , tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isode Sil group, sec-decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl) , a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group;

Deuterium, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, nitro group, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group Tyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec- Decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group; and

-X ₁ (R ₁ )(R ₂ )(R ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₃ )(Q ₄ ), and -P(=O)(Q ₅ )(Q ₆ ); selected from among

At least one of R ₁₁ to R ₁₈ is represented by -X ₁ (R ₁ )(R ₂ )(R ₃ ),

Q ₁ to Q ₆ are each independently,

C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, phenyl group and naphthyl group;

a phenyl group and a naphthyl group substituted with at least one of a C ₁ -C ₁₀ alkyl group, a phenyl group, and a naphthyl group; can be selected from

According to another embodiment, in Formula 1, R ₁₁ to R ₁₈ are each independently hydrogen, deuterium, -F, cyano group, nitro group, -SF ₅ , -CH ₃ , -CD ₃ , -CD ₂ H , -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a group represented by the following formulas 9-1 to 9-17, a group represented by the following formulas 10-1 to 10-16, and -X ₁ ( R ₁ )(R ₂ )(R ₃ ), wherein at least one of R ₁₁ to R ₁₈ may be represented by -X ₁ (R ₁ )(R ₂ )(R ₃ ):

In Formula 1, X ₁ is silicon (Si) or germanium (Ge).

For example, X ₁ in Formula 1 may be silicon, but is not limited thereto.

In Formula 1, R ₁ to R ₃ and Q ₁ to Q ₆ are each independently hydrogen, deuterium, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, A substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ hetero Cycloalkyl 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 and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formula 1, R ₁ to R ₆ are each independently

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

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, C ₃ -C ₁₀ cyclo Alkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₁₄ aryl group, C ₁ -C ₁₄ heteroaryl group, monovalent ratio - a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of a condensed aromatic polycyclic group and a monovalent non-aromatic condensed heteropolycyclic 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 ₁₄ aryl group, C ₁ -C ₁₄ hetero an aryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group; and

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₁₀ cyclo Alkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₁₄ aryl group, C ₁ -C ₁₄ heteroaryl group, monovalent ratio -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 ₁₄ aryl group, C ₁ -C ₁₄ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group; can be selected from

As another example, in -X ₁ (R ₁ )(R ₂ )(R ₃ ) of Formula 1, R ₁ to R ₃ are each independently

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

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₁₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cycloox substituted with at least one of a tyl group, an adamantanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group, C ₁ - C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorine group Nyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, iso Thiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolyl group Nyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl 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, imidazopyridinyl group and an imidazopyrimidinyl group; and

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohex Sil group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, Anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group , quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzoxazolyl group , triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl group substituted with at least one of a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group (adamantanyl), a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group , naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl 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, fu Linyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl 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, di a benzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; can be selected from

According to one embodiment, in -X ₁ (R ₁ )(R ₂ )(R ₃ ) of Formula 1, R ₁ to R ₃ are each independently,

Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group , n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-ox Tyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec-decyl group, tert-decyl group, methoxy group, ethoxy group , propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group; and

Deuterium, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, nitro group, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group Tyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec- Decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group; may be selected from, but is not limited thereto.

According to another embodiment, in -X ₁ (R ₁ )(R ₂ )(R ₃ ) of Formula 1, R ₁ to R ₃ are each independently

a methyl group, an ethyl group, and a phenyl group; and

a phenyl group substituted with at least one of deuterium, a methyl group, an ethyl group, and a phenyl group; can be selected from

For example, in -X ₁ (R ₁ )(R ₂ )(R ₃ ) of Formula 1, R ₁ to R ₃ may be the same as each other.

According to one embodiment, the organometallic compound represented by Formula 1 may be represented by one of Formulas 1-1 to 1-77:

In Formulas 1-1 to 1-77, R ₁₀₀ to R ₁₀₂ are each independently represented by -X ₁ (R ₁ )(R ₂ )(R ₃ ), and R ₁₁ to R ₁₈ are described in Formula 1 See the description for

For example, in Formulas 1-1 to 1-77,

R ₁₀₀ to R ₁₀₂ are each independently represented by -X ₁ (R ₁ )(R ₂ )(R ₃ ),

R ₁ to R ₃ are independently of each other,

Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group , n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-ox Tyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec-decyl group, tert-decyl group, methoxy group, ethoxy group , propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group; and

Deuterium, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, nitro group, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group Tyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec- Decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group; is selected from

R ₁₁ to R ₁₈ are each independently,

Hydrogen, deuterium, -F, cyano group, nitro group, -SF ₅ , methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n -pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group , tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isode Sil group, sec-decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl) , a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group;

Deuterium, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, nitro group, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group Tyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec- Decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group; and

-N(Q ₁ )(Q ₂ ), -B(Q ₃ )(Q ₄ ) and -P(=O)(Q ₅ )(Q ₆ ); is selected from

Q ₁ to Q ₆ are each independently,

C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, phenyl group and naphthyl group;

a phenyl group and a naphthyl group substituted with at least one of a C ₁ -C ₁₀ alkyl group, a phenyl group and a naphthyl group; can be selected from

As another example, in Formulas 1-1 to 1-77,

R ₁₀₀ to R ₁₀₂ are each independently represented by -X ₁ (R ₁ )(R ₂ )(R ₃ ),

Wherein R ₁ To R ₃ Are independently of each other,

a methyl group, an ethyl group, and a phenyl group; and

a phenyl group substituted with at least one of deuterium, a methyl group, an ethyl group, and a phenyl group; is selected from

The R ₁₁ to R ₁₈ are each independently hydrogen, deuterium, -F, cyano group, nitro group, -SF ₅ , -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , - CF ₂ H, -CFH ₂ , may be selected from the group represented by Formulas 9-1 to 9-17 and the group represented by Formulas 10-1 to 10-16, but is not limited thereto.

As another example, in Formulas 1-1 to 1-77,

R ₁₀₀ to R ₁₀₂ are each independently represented by -X ₁ (R ₁ )(R ₂ )(R ₃ ),

Wherein X ₁ is Si, R ₁ to R ₃ may be the same as each other, but is not limited thereto.

For example, the organometallic compound may include at least one of the following compounds 1 to 327 and 401 to 727:

A method of synthesizing the organometallic compound represented by Chemical Formula 1 may be easily recognized by those skilled in the art with reference to Synthesis Examples to be described later.

Formula 11

<Formula 11>

In Formula 11, L ₁ to L ₅ are each independently, a substituted or unsubstituted C ₁ -C ₆₀ alkylene group, a substituted or unsubstituted C ₂ -C ₆₀ alkenylene group, or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, substituted or unsubstituted 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 condensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed) polycyclic group) and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group (substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group).

For example, in Formula 11, L ₁ to L ₅ are each independently

phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acetonitrile Naphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group (fluoranthrenylene), triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenyl pentaphenylene, hexacenylene, pyrrolylene, imidazolylene, pyrazolylene, pyridinylene, pyrazinylene, pyrimidi Nylene group (pyrimidinylene), pyridazinylene group (pyridazinylene), isoindolylene group (isoindolylene), indolylene group (indolylene), indazolylene group (indazolylene), purinylene group (purinylene), quinolinylene group (quinolinylene) , isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene , cinnolinylene, carbazolylene, phenanthridinylen e), acridinylene group, phenanthrolinylene group, phenazinylene group, benzooxazolylene group, benzoimidazolylene group, furanylene group, Benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group (isoxazolylene), oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzothiophenylene group ), a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene 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, C ₆ -C ₂₀ aryl group, phenyl group-substituted phenyl group, C ₁ -C ₂₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group , a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, substituted with at least one of a monovalent non-aromatic condensed heteropolycyclic group and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) , heptalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group, triphenylenylene group , pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pyrrolylene group, imidazolylene group, pyrazolylene group, pyridinylene group, pyrazinylene group , pyrimidinylene group, pyridazinylene group, isoindolylene group, indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, Naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinolinylene group, carbazolylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoxazolylene group, benzoimi Dazolylene group, furanylene group, benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group, oxazolylene group, triazolylene group, tetra a zolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene group; is selected from

Q ₃₃ to Q ₃₅ are each independently, hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazole Diary, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group phthalazinyl group, quinoxalinyl group , it may be selected from a cinolinyl group and a quinazolinyl group.

According to one embodiment, L ₁ to L ₅ in Formula 11 may be each independently one of Formulas 12-1 to 12-37:

In Formulas 12-1 to 12-37,

Y ₁ is O, S, S(=O), S(=O) ₂ , C(Z ₃ )(Z ₄ ), N(Z ₅ ), or Si(Z ₆ )(Z ₇ );

Z ₁ To Z ₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl group Acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, triphenylenyl group , pyrenyl group, phenanthrenyl group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, and -Si(Q ₃₃ )(Q ₃₄ )(Q ₄₅ );

wherein Q ₃₃ to Q ₄₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carba Zolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group phthalazinyl group, quinoxali group selected from a nyl group, a cinolinyl group, and a quinazolinyl group;

d1 is selected from an integer from 1 to 4;

d2 is selected from an integer from 1 to 3;

d3 is an integer from 1 to 6;

d4 is selected from an integer from 1 to 8;

d5 is 1 or 2;

d6 is selected from an integer from 1 to 5;

* is a binding site with a neighboring atom.

According to another embodiment, L ₁ to L ₅ in Formula 11 are each independently

Phenylene group, naphthylene group, phenanthrenylene group, anthracenylene group, triphenylenylene group, carbazolylene group, pyridinylene group, pyrimidinylene group, triazinylene group, quinazolinylene group, quinolinylene group, isoquinylene group a nolinylene group, a naphthyridinylene group, and an oxadiazolylene 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, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, and a phenylene group substituted with at least one of a phenanthrenyl group , naphthylene group, phenanthrenylene group, anthracenylene group, triphenylenylene group, carbazolylene group, pyridinylene group, pyrimidinylene group, triazinylene group, quinazolinylene group, quinolinylene group, isoquinolinyl group a ren group, a naphthyridinylene group and an oxadiazolylene group; may be selected from, but is not limited thereto.

According to another embodiment, L ₁ to L ₅ in Formula 1 may each independently represent one of Formulas 13-1 to 13-33, but are not limited thereto:

In Formulas 13-1 to 13-33, * and *' independently represent binding sites with neighboring atoms.

In Formula 11, a1 represents the number of L ₁ s and may be 0, 1, 2, 3, 4, or 5, for example, 0, 1, or 2, and as another example, may be 0 or 1. When a1 is 0, L ₁ is a single bond. When a1 is 2 or more, two or more L ₁ may be the same as or different from each other. Descriptions of a2 to a5 may be understood with reference to the description of a1 and the structure of Formula 11.

According to an embodiment, a1 to a5 in Formula 11 may each independently be 0, 1, or 2, for example, 0 or 1, but is not limited thereto.

In Formula 11, R ₁ to R ₄ , R ₁₁ and R ₁₂ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino A 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 , 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 a 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 ring group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ) and -B(Q ₆ )( Q ₇ );

At least one of R ₂ to R ₄ is, independently of each other, 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 unsubstituted It may be selected from a cyclic monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formula 11, R ₁ to R ₄ , R ₁₁ and R ₁₂ may each independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, An amino group, an amidino group, a hydrazine group, a hydrazone group, a 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 ₂₀ alkyl group, a substituted or unsubstituted C ₁ - C ₂₀ alkoxy group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C ₁ -C ₂₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and substituted or unsubstituted selected from the monovalent non-aromatic condensed heteropolycyclic group;

At least one of R ₂ to R ₄ is, independently of each other, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent ratio -It may be selected from a condensed aromatic polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

According to one embodiment, in Formula 11, R ₁ to R ₄ , R ₁₁ and R ₁₂ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of salts thereof;

A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group ), fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group (phenalenyl), phenanthrenyl group (phenanthrenyl), anthracenyl group, fluoran Tenyl group (fluoranthenyl), triphenylenyl group (triphenylenyl), pyrenyl group (pyrenyl), chrysenyl group (chrysenyl), naphthacenyl group (naphthacenyl), picenyl group (picenyl), perylenyl group (perylenyl), penta Phenyl group (pentaphenyl), hexacenyl group (hexacenyl), pentacenyl group (pentacenyl), rubicenyl group (rubicenyl), coronenyl group (coronenyl), ovalenyl group (ovalenyl), pyrrolyl group (pyrrolyl), thiophenyl group ), furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl , pyridinyl group, pyrazinyl group (pyrazinyl), pyrimidinyl group (pyrimidinyl), pyridazinyl group (pyridazinyl), isoindolyl group (isoindolyl), indolyl group (indolyl), indazolyl group (indazolyl), Purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl , quinazolinyl group, cinnolinyl group, carbazolyl group ( carbazolyl), phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl (benzothiophenyl), isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl ), triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, pyrido a benzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group and a pyrimidobenzothiophenyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, C ₁ -C ₂₀ alkyl group-substituted phenyl group, phenyl group-substituted 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, fluorante Nyl 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, isobenzoxazolyl group , triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl 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, an acenaphthyl group, a flu Orenyl 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 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, pyridi Nyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridi Nyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazole Diary, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group , imidazopyridinyl group, imidazopyrimidinyl group, imidazopyrimidinyl group, pyridobenzofuranyl group, pyrimidobenzofuranyl group, pyridobenzothiophenyl group and pyrimidobenzothiophenyl group; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ) ; is selected from;

The Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ are each independently, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, flu Orenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinyl group It may be selected from a nolinyl group, a quinazolinyl group, and a quinoxalinyl group.

According to another embodiment, at least one of R ₂ to R ₄ in Formula 11 is, independently of each other,

Triphenylenyl group, carbazolyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyri Dazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cy Nolinyl group, phenanthridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group, benzothiazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxa Diazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, imidazopyridinyl group, imidazopyrimidinyl group, pyridobenzofuranyl group, pyrimidobenzofuranyl group, pyridobenzothiophenyl group and pyrimido benzothiophenyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, C ₁ -C ₂₀ alkyl group-substituted phenyl group, phenyl group-substituted phenyl group, naphthyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl and -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ) substituted with at least one of a triphenylenyl group, a carbazolyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an 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, phenanthridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group, benzothiazolyl group, isobenzothiazolyl group, benzoxazolyl group, iso benzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, imidazopyridinyl group, imidazopyrimidinyl group, pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group and a pyrimidobenzothiophenyl group; can be selected from

According to another embodiment, at least one of R ₂ to R ₄ in Formula 11 is, independently of each other,

Pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, benzothiazolyl group, isobenzothiazolyl group, benzo Oxazolyl group, isobenzooxazolyl group, oxadiazolyl group, triazinyl group, imidazopyridinyl group, imidazopyrimidinyl group, pyridobenzofuranyl group, pyrimidobenzofuranyl group, pyridobenzothiophenyl group and pyrido midobenzothiophenyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, C ₁ -C ₂₀ alkyl group-substituted phenyl group, phenyl group-substituted phenyl group, naphthyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl and -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ) substituted with at least one of a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolyl group Nyl group, benzothiazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, oxadiazolyl group, triazinyl group, imidazopyridinyl group, imidazopyrimidinyl group, pyridobenzofuranyl group , a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group and a pyrimidobenzothiophenyl group; may be selected from, but is not limited thereto.

According to another embodiment, at least one of R ₂ to R ₄ in Formula 11 is each independently selected from the group consisting of:

thiophenyl group, furanyl group, carbazolyl group, acridinyl, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and dibenzocarbazolyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, C ₁ -C ₂₀ alkyl group-substituted phenyl group, phenyl group-substituted phenyl group, naphthyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group and -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ) substituted with at least one of a thiophenyl group, a furanyl group, a carbazolyl group, an acridinyl, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group; can be selected from

According to another embodiment, at least one of R ₂ to R ₄ in Formula 11 is each independently selected from the group consisting of:

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, penta a cenyl group, a rubysenyl group, a coronenyl group and an ovalenyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, C ₁ -C ₂₀ alkyl group-substituted phenyl group, phenyl group-substituted phenyl group, naphthyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl 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, an acenaphthyl group, a fluorenyl group, a spiro-flu Orenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group and ovalenyl group; can be selected from

According to another embodiment, at least one of R ₂ to R ₄ in Formula 11 is, independently of each other,

Thiophenyl group, furanyl group, carbazolyl group, acridinyl, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl 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, fluorante a nyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubysenyl group, a coronenyl group and an ovalenyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, C ₁ -C ₂₀ alkyl group-substituted phenyl group, phenyl group-substituted phenyl group, naphthyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group and -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ) substituted with at least one of a thiophenyl group, a furanyl group, a carbazolyl group, acridinyl, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a 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, phenyl group Nalenyl 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 group, rubysenyl group, coronenyl group and ovalenyl group; may be selected from, but is not limited thereto.

For example, in Formula 11, R ₁ to R ₄ , R ₁₁ and R ₁₂ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of salts thereof;

Formulas 14-1 to 14-48, 15-1 to 15-6, and 16-1 to 16-5; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ) ; is selected from;

Wherein Q ₃ To Q ₅ are each independently, C ₁ -C ₂₀ Alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, chrysenyl group , carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group and a quinoxalinyl group,

At least one of R ₂ to R ₄ may be each independently selected from Formulas 14-1 to 14-48, 15-1 to 15-6, and 16-1 to 16-5, but is not limited thereto. :

In Formulas 14-1 to 14-48, 15-1 to 15-6, and 16-1 to 16-5,

Y ₃₁ is O, S, C(Z ₃₃ )(Z ₃₄ ), N(Z ₃₅ ) or Si(Z ₃₆ )(Z ₃₇ );

Z ₃₁ to Z ₃₇ 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 an acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, Naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridi a nyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ );

wherein Q ₃₃ to Q ₃₅ are each independently, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, chrysenyl group , carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group and a quinoxalinyl group;

e2 is 1 or 2;

e3 is selected from an integer from 1 to 3;

e4 is selected from an integer from 1 to 4;

e5 is selected from an integer from 1 to 5;

e6 is selected from an integer from 1 to 6;

e7 is selected from an integer from 1 to 7;

* is a binding site with a neighboring atom.

In Formula 11, b1 represents the number of R ₁ , and may be 1, 2, 3, or 4, for example, 1 or 2, or as another example, 1. When b1 is 2 or more, two or more R ₁ may be the same as or different from each other. The description of b2 to b4 may be understood with reference to the description of b1 and the structure of Formula 1.

According to one embodiment, b1 to b4 in Formula 11 may each independently be 1 or 2, for example, 1, but is not limited thereto.

In Formula 11, c1 represents the number of -[(L ₁ ) _a1 -(R ₁ ) _b1 ], and may be 1, 2, 3, or 4, for example, 1 or 2, or as another example, 1. When c1 is 2 or more, two or more -[(L ₁ ) _a1 -(R ₁ ) _b1 ] may be the same as or different from each other.

According to one embodiment, in Formula 1, c1 may be 1, a1 may be 0, and R ₁ may be hydrogen.

According to another embodiment, both R ₁₁ and R ₁₂ in Formula 11 may be hydrogen.

According to another embodiment, in Formula 11, a1 is 0, c1, b11, and b12 are 1, and R ₁ , R ₁₁ and R ₁₂ 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group, It may be selected from a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group, but is not limited thereto.

According to another embodiment, in Formula 11, a2 and a3 may be 0, and R ₂ and R ₃ may be hydrogen.

According to another embodiment, in Formula 11, a3 and a4 may be 0, and R ₃ and R ₄ may be hydrogen.

According to another embodiment, in Formula 11, a2 and a4 may be 0, and R ₂ and R ₄ may be hydrogen.

According to another embodiment, the compound represented by Formula 11 may be represented by Formula 11A or 11B below:

<Formula 11A>

<Formula 11B>

Descriptions of X ₁ , L ₃ , L ₅ , a3, a5, b2, b3, R ₁₁ , R ₁₂ , b11 and b12 in Formula 11A are the same as those of Formula 11,

R ₂ and R ₃ are a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted Cyclic 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 non-aromatic condensation a polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formulas 11A and 11B,

L ₃ and L ₅ are independently of each other,

a phenylene group, a naphthylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, and a carbazolylene 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, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, and a phenylene group substituted with at least one of a phenanthrenyl group , a naphthylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, and a carbazolylene group;

a3 and a5 are each independently 0, 1 or 2;

R ₁₁ and R ₁₂ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl group an acid or a salt thereof, a sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group;

wherein R ₂ and R ₃ are each independently selected from Formulas 14-1 to 14-48, 15-1 to 15-6, and 16-1 to 16-5,

b11 and b12 may be 1, but is not limited thereto.

According to another embodiment, both R ₁₁ and R ₁₂ in Formulas 11A and 11B may be hydrogen, but the present invention is not limited thereto.

The compound represented by Formula 11 may be one of the following compounds (11)-1 to (11)-131, but is not limited thereto:

The carbazole-based compound represented by Chemical Formula 11 is 1) a “carbazole ring” is bonded to the “3rd carbon” of the “A ring”, optionally with -(L ₅ ) _a5 - interposed therebetween (the following formula 11'), 2) at least one of R ₂ to R ₄ is, independently of each other, 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 Selected from a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group (that is, at least one of R ₂ to R ₄ in Formula 11 is necessarily a "cyclic group"). Accordingly, the electron density of the “ring A” of Formula 11 can be effectively controlled, and the charge transport ability of the carbazole-based compound represented by Formula 11 can be easily controlled by controlling the substituents of R ₂ to R ₄ .

<Formula 11'>

For example, the results of simulation evaluation using Gaussian for HOMO, LUMO, T ₁ energy level and S ₁ energy level for some of the compounds (11)-1 to (11)-131 are shown in Table 1 below. same:

A method for synthesizing the compound represented by Formula 11 can be easily recognized by those skilled in the art with reference to the Synthesis Examples to be described later.

Formulas 21A to 21C

<Formula 21A>

<Formula 21B>

<Formula 21C>

<Formula 22A>

<Formula 22B>

<Formula 22C>

<Formula 22D>

<Formula 22E>

<Formula 22F>

The relationship between the group represented by Formulas 22A to 22F and the compound represented by one of Formulas 21A to 21C will be described later.

In Formula 21A, ring A is a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or an unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non- It may be an aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heterocondensed polycyclic group, a group represented by Formula 22A, or a group represented by Formula 22B.

According to one embodiment, ring A of Formula 21A is,

Phenyl group, naphthyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl 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, quinolinyl group, isoquinolinyl group, benzoquinyl group Nolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group, isobenzothiazolyl group, benzoxazolyl group , isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, imidazopyridinyl group, imidazopyrimidinyl group, benzofuropyrazinyl group, benzofuropyrazinyl group a midinyl group, a benzofuropyridinyl group, a benzothienopyrazinyl group, a benzothienopyrimidinyl group, a benzothienopyridinyl group, a group represented by Formula 22A or a group represented by Formula 22B; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or A salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a phenyl group substituted with a C ₁ -C ₂₀ alkyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group , pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, biphenyl group and -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ) substituted with at least one of a phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, an imidazolyl group, a pyrazole diary, thiazolyl 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, phenanthridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group , isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, imidazopyridinyl group, imidazopyrimidinyl group, benzofuro a pyrazinyl group (benzofuropyrazinyl), a benzofuropyrimidinyl group, a benzofuropyridinyl group, a benzothienopyrazinyl group, a benzothienopyrimidinyl group and a benzothienopyridinyl group; is selected from

wherein Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, triphenylenyl group, pyrenyl group, phenanthrenyl group, Fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, iso It may be a quinolinyl group, a quinazolinyl group or a quinoxalinyl group.

According to another embodiment, Ring A of Formula 21A may be selected from among the groups represented by Formulas 24-1 to 24-51, Formulas 26-1 to 26-5, Formula 22A and the group represented by Formula 22B. One may be represented, but not limited to:

In Formulas 24-1 to 24-51 and 26-1 to 26-5,

Y ₃₁ is O, S, C(Z ₃₃ )(Z ₃₄ ), N(Z ₃₅ ) or Si(Z ₃₆ )(Z ₃₇ );

Z ₃₁ to Z ₃₇ 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 An acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a C ₁ -C ₂₀ alkyl group substituted phenyl group, a phenyl group, a naphthyl group, an anthracenyl group , triphenylenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group , a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a biphenyl group, or -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ );

wherein Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, triphenylenyl group, pyrenyl group, phenanthrenyl group, Fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, iso a quinolinyl group, a quinazolinyl group, or a quinoxalinyl group;

e1 is an integer from 1 to 5, e2 is an integer from 1 to 7, e3 is an integer from 1 to 3, e4 is an integer from 1 to 4, e5 is 1 or 2, and e6 is an integer from 1 to 6 , and * is a binding site with a neighboring atom.

Ring B ₁ in Formula 21A may be a C ₅ -C ₂₀ cyclic group or a C ₁ -C ₂₀ heterocyclic group that does not include nitrogen as a ring-forming atom.

For example, ring B ₁ in Formula 21A may be benzene, naphthalene, anthracene, phenanthrene, benzofuran, or benzothiophene.

According to one embodiment, Ring B ₁ in Formula 21A may be benzene, naphthalene, phenanthrene, or benzofuran.

In Formulas 21B and 21C, Ring B ₂ , Ring B ₃ , Ring C ₁ , and Ring C ₂ are each independently a C ₅ -C ₂₀ cyclic group or a C ₁ -C ₂₀ heterocyclic group, wherein Ring B ₂ and at least one of Ring B ₃ is a C ₁ -C ₂₀ heterocyclic group containing nitrogen as a ring-forming atom, and at least one of Ring C ₁ and Ring C ₂ is a C ₁ -C containing nitrogen as a ring-forming atom. ₂₀ is a heterocyclic group.

According to one embodiment, in Formulas 21A to 21D and 22A to 22F, Ring B ₂ , Ring B ₃ , Ring C ₁ , and Ring C ₂ may be each independently selected from benzene, naphthalene, anthracene, phenanthrene, benzofuran, benzothi Opene, pyridine, pyrimidine, pyrazine, benzofuropyrazine, benzofuropyrimidine benzofuropyridine, benzothienopyrazine, benzothienopyrimidine or benzothienopyridine;

At least one of Ring B ₂ and Ring B ₃ is pyridine, pyrimidine, pyrazine, benzofuropyrazine, benzofuropyrimidine benzofuropyridine, benzothienopyrazine, benzothienopyrimidine or benzothienopyridine; ,

At least one of Ring C ₁ and Ring C ₂ is pyridine, pyrimidine, pyrazine, benzofuropyrazine, benzofuropyrimidine benzofuropyridine, benzothienopyrazine, benzothienopyrimidine or benzothienopyridinyl can

According to another embodiment, in Formulas 21A to 21D and 22A to 22F, Ring B ₂ , Ring B ₃ , Ring C ₁ and Ring C ₂ are each independently benzene, naphthalene pyridine, pyrimidine or pyrazine,

at least one of ring B ₂ and ring B ₃ is pyridine, pyrimidine or pyrazine,

At least one of ring C ₁ and ring C ₂ may be pyridine, pyrimidine or pyrazine.

In Formulas 21A and 21B, Pc ₁ and Pc ₂ may each independently represent a group represented by Formula 22A or a group represented by Formula 22B.

In Formula 21C, Cz ₁ , Cz ₂ and Cz ₃ are each independently a group represented by Formula 22C, a group represented by Formula 22D, a group represented by Formula 22E, or a group represented by Formula 22F.

In Formulas 21A to 21C, c1, c2, c11, c12, c13, p1, p2, p11, p12, and p13 are each independently selected from an integer of 0 to 3.

When c1 and c2 in Formulas 21A and 21B are both 0, ring A is a group represented by Formula 22A or a group represented by Formula 22B, and Ring A in Formulas 21A and 21B is represented by Formula 22A When it is not a group or a group represented by Formula 22B, c1 + c2 ≠ 0.

That is, Formulas 21A and 21B necessarily include one of the group represented by Formula 22A and the group represented by Formula 22B.

At least one of Ring A in Formula 21A, all R ₁ in Formula 21A, and R ₂ in Formula 21A is an electron transporting moiety.

The electron transporting moiety is a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, including at least one of the following moieties 1 as a ring-forming moiety. , a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group. Here, since the carbazole-based group not having the following moiety 1 does not have the following moiety 1, it is not included in the electron transporting moiety as described above.

<Moiety 1>

In moiety 1, ** and *** are binding sites with each neighboring ring-forming atom in the ring in which moiety 1 is included.

Specific examples of the electron transporting moiety may include groups represented by Formulas 24-1 to 24-51, but are not limited thereto.

In Formula 21C, c11 + c12 + c13 ≠ 0.

That is, Formula 21C necessarily includes at least one of the groups represented by Formulas 22C to 22F.

When all Cz ₁ , Cz ₂ and Cz ₃ in Formula 21C are a group represented by Formula 22C or a group represented by Formula 22D, all R ₁₁ in Formula 21C and all R in Formula 21C ₁₂ and at least one of all R ₁₃ in Formula 21C is an electron transporting moiety. Here, the description of the electron transporting moiety refers to the description herein.

According to one embodiment, in Formulas 21A and 21B,

c1 = 0, c2 = 0, and ring A is a group represented by Formula 22A or a group represented by Formula 22B;

c1 = 1 and c2 = 0;

c1 = 1, and c2 = 1.

According to another embodiment, in Formula 21C,

c11 = 1, c12 = 0, c13 = 0;

c11 = 0, c12 = 0, c13 = 1;

c11 = 1, c12 = 1, c13 = 0;

c11 = 1, c12 = 0, c13 = 1.

In Formulas 21A to 21C and 22A to 22F, L ₁ to L ₃ , L ₁₁ to L ₁₃ , L ₂₁ to L ₂₄ , and L ₃₁ to L ₃₃ are each independently, a substituted or unsubstituted C ₁ -C ₆₀ alkylene group , substituted or unsubstituted C ₂ -C ₆₀ alkenylene group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, 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 It may be selected from a ren group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.

For example, in Formulas 21A to 21C and 22A to 22F, L ₁ to L ₃ , L ₁₁ to L ₁₃ , L ₂₁ to L ₂₄ and L ₃₁ to L ₃₃ are each independently

phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acetonitrile Naphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group (fluoranthrenylene), triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenyl pentaphenylene, hexacenylene, pyrrolylene, imidazolylene, pyrazolylene, pyridinylene, pyrazinylene, pyrimidi Nylene group (pyrimidinylene), pyridazinylene group (pyridazinylene), isoindolylene group (isoindolylene), indolylene group (indolylene), indazolylene group (indazolylene), purinylene group (purinylene), quinolinylene group (quinolinylene) , isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene , cinnolinylene, carbazolylene, phenanthridinylen e), acridinylene group, phenanthrolinylene group, phenazinylene group, benzooxazolylene group, benzoimidazolylene group, furanylene group, Benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group (isoxazolylene), oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzothiophenylene group ), a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene 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, C ₆ -C ₂₀ aryl group, C ₁ -C ₂₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indium substituted with at least one of a condensed heterocyclic group and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) Cenylene group, acenaphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group, triphenylenylene group, pyrenylene group, cry Cenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pyrrolylene group, imidazolylene group, pyrazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, Pyridazinylene group, isoindolylene group, indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinox Salinylene group, quinazolinylene group, cinolinylene group, carbazolylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoxazolylene group, benzoimidazolylene group, furanyl Ren group, benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group, oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolyl a ren group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene group; is selected from

Q ₃₃ to Q ₃₅ are each independently, hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazole Diary, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, phthalazinyl group, quinoxali group It may be selected from a nyl group, a cinolinyl group, and a quinazolinyl group.

According to one embodiment, in Formulas 21A to 21C and 22A to 22F, L ₁ to L ₃ , L ₁₁ to L ₁₃ , L ₂₁ to L ₂₄ and L ₃₁ to L ₃₃ are each independently selected from Formulas 12-1 to 12-37 may be selected.

According to another embodiment, in Formulas 21A to 21C and 22A to 22F, L ₁ to L ₃ , L ₁₁ to L ₁₃ , L ₂₁ to L ₂₄ and L ₃₁ to L ₃₃ are each independently selected from the group consisting of:

a phenylene group, a naphthylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, and a carbazolylene 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, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a phenanthrenyl group and at least one of a biphenyl group substituted with a phenylene group, a naphthyl group a ren group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, and a carbazolylene group; may be selected from, but is not limited thereto.

According to another embodiment, L ₁ to L ₃ , L ₁₁ to L ₁₃ , L ₂₁ to L ₂₄ and L ₃₁ to L ₃₃ in Formulas 21A to 21C and 22A to 22F are each independently selected from Formulas 13-1 to 13-33, but is not limited thereto.

In Formulas 21A to 21C, a1 represents the number of L ₁ , and may be 0, 1, 2, 3, 4, 5, or 6, for example, 0, 1, or 2, and as another example, may be 0 or 1. When a1 is 0, L ₁ is a single bond. When a1 is 2 or more, two or more L ₁ may be the same as or different from each other. Descriptions of a2 to a3, a11 to a13, a21 to a24, and a31 to a33 may be understood with reference to the description of a1 and structures of Formulas 21A to 21C and 22A to 22F.

According to one embodiment, in Formula 21, a1 to a3, a11 to a13, a21 to a24, and a31 to a33 may each independently be 0, 1 or 2, for example, 0 or 1, but is limited thereto. it is not

In Formulas 21A to 21C and 22A to 22F, R ₁ , R ₂ , R ₁₁ to R ₁₃ , R ₂₁ to R ₂₃ , R ₃₁ to R ₃₃ may be each independently selected from 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, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, 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, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, a group represented by Formula 22A, a group represented by Formula 22B , -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), and -B(Q ₆ )(Q ₇ ).

For example, in Formulas 21A to 21C and 22A to 22F, R ₁ , R ₂ , R ₁₁ to R ₁₃ , R ₂₁ to R ₂₃ , R ₃₁ to R ₃₃ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of salts thereof;

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, penta Cenyl 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, pyri Dinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthi Ridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothia Zolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazole diary, imidazopyridinyl group and imidazopyrimidinyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group substituted with C ₁ -C ₂₀ alkyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, inda Cenyl 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, 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, indole group Diary, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrinyl group Dinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetra Zolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, biphenyl 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, an acenaphthyl group, a 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 group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubise Nyl 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 group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxali Nyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxa Zolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopi a ridinyl group and an imidazopyrimidinyl group; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ); is selected from

wherein Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group , fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, It may be selected from an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group.

According to another embodiment, in Formulas 21A to 21C and 22A to 22F, R ₁ , R ₂ , R ₁₁ to R ₁₃ , R ₂₁ to R ₂₃ , R ₃₁ to R ₃₃ are independently of each other,

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of salts thereof;

Formulas 24-1 to 24-51, Formulas 25-1 to 25-6, and 26-1 to 26-5; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ) ; is selected from

Wherein Q ₃ To Q ₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, cry Cenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quina It may be selected from a jolinyl group and a quinoxalinyl group, but is not limited thereto:

In Formulas 24-1 to 24-51, 25-1 to 25-6, and 26-1 to 26-5,

Y ₃₁ is O, S, C(Z ₃₃ )(Z ₃₄ ), N(Z ₃₅ ) or Si(Z ₃₆ )(Z ₃₇ );

Z ₃₁ to Z ₃₇ 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 An acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a C ₁ -C ₂₀ alkyl group substituted phenyl group, a phenyl group, a naphthyl group, an anthracenyl group , triphenylenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group , a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a biphenyl group and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ );

wherein Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, triphenylenyl group, pyrenyl group, phenanthrenyl group, Fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, iso selected from a quinolinyl group, a quinazolinyl group and a quinoxalinyl group;

e1 is an integer from 1 to 5, e2 is an integer from 1 to 7, e3 is an integer from 1 to 3, e4 is an integer from 1 to 4, e5 is 1 or 2, and e6 is an integer from 1 to 6 , and * is a binding site with a neighboring atom.

In Formulas 21A to 21C and 22A to 22F, b1, b2, b11 to b13, b21 to b23, and b31 to b33 are each independently selected from an integer of 0 to 4. For example, b1, b2, b11 to b13, b21 to b23, and b31 to b33 may each independently be 0 or 1, but are not limited thereto.

Formula 22A is represented by one of Formulas 22A(1) to 22A(5), Formula 22B is represented by Formula 22B(1) or 22B(2), and Formula 22D is represented by Formula 22D(1) to 22D(5), and the Chemical Formula 22F may be represented by one of the following Chemical Formulas 22F(1) and 22F(2).

<Formula 22A(1)>

<Formula 22A(2)>

<Formula 22A(3)>

<Formula 22A(4)>

<Formula 22A(5)>

<Formula 22B(1)>

<Formula 22B(2)>

<Formula 22E(1)>

<Formula 22E(2)>

<Formula 22E(3)>

<Formula 22E(4)>

<Formula 22E(5)>

<Formula 22F(1)>

<Formula 22F(2)>

In Formulas 22A(1) to 22A(5), 22B(1) and 22B(2), 22E(1) to 22E(5), 22F(1), and 22F(2), L ₂₁ to L ₂₄ , a21 to a24, R ₂₁ to R ₂₃ , b21 to b23 , L ₃₁ to L ₃₃ , a31 to a33 , R ₃₁ to R ₃₃ , b31 to b33 and c21 to c23 , c31 and c32 are described in Formulas 21A to 21C and 22A above. See the description of to 22F.

For example, in Formulas 22A(1) to 22A(5), 22B(1), and 22B(2), a24 is 0, 1, or 2, L ₂₄ is selected from Formulas 12-1 to 12-37, and , c11, c12 and c13 may be hydrogen, but are not limited thereto.

The compound represented by one of Formulas 21A to 21C may be represented by one of Formulas 21A(1) to 21A(8) below:

<Formula 21A(1)> <Formula 21A(2)>

<Formula 21A(3)> <Formula 21A(4)>

<Formula 21A(5)> <Formula 21A(6)>

<Formula 21A(7)> <Formula 21A(8)>

In Formulas 21A(1) to 21A(8),

Ring A is a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, comprising at least one moiety 1 above as a ring-forming moiety, a substituted or an unsubstituted C ₁ -C ₆₀ heteroaryl group or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group (eg, a group represented by one of Formulas 24-1 to 24-51);

Descriptions of Pc ₁ , Pc ₂ , L ₃ , a3, R ₁ , R ₂ , p1 and p2 are the same as those described in the descriptions for Formulas 21A to 21C and 22A to 22F,

The descriptions for R ₃ and R ₄ are the same as those described for the above formulas 21A to 21C and 22A to 22F.

According to another embodiment, the condensed cyclic compound represented by one of Formulas 21A to 21C may be represented by one of Formulas 21B(1) to 21B(10) below:

<Formula 21B(1)> <Formula 21B(2)>

<Formula 21B(3)> <Formula 21B(4)>

<Formula 21B(5)> <Formula 21B(6)>

<Formula 21B(7)> <Formula 21B(8)>

<Formula 21B(9)> <Formula 21B(10)>

Descriptions of rings A, Pc ₁ , Pc ₂ , L ₃ , a3 , R ₁ , R ₂ , p1 and p2 in Formulas 21B(1) to 21B(10) are given for Formulas 21A to 21C and 22A to 22F. See what is described in the description.

According to another embodiment, the condensed cyclic compound represented by one of Chemical Formulas 21A to 21C may be represented by the following Chemical Formula 21C(1) or 21C(2):

<Formula 21C(1)> <Formula 21C(2)>

The descriptions of Cz ₁ , Cz ₂ , Cz ₃ , R ₁₁ , R ₁₂ , R ₁₃ , p11 , p12 and p13 in Formulas 21C(1) and 21C(2) are for Formulas 21A to 21C and 22A to 22F. See description.

According to another embodiment, the condensed cyclic compound represented by one of Chemical Formulas 21A to 21C may be represented by the following Chemical Formula 21C(3):

<Formula 21C(3)>

In Formula 21C(3),

Cz ₃ , L ₁₁ and a11 refer to the description of Formulas 21A to 21C and 22A to 22F above,

R ₁₁ is a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, including at least one moiety 1 above as a ring-forming moiety, a substituted or an unsubstituted C ₁ -C ₆₀ heteroaryl group or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group (for example, a group represented by one of Formulas 4-1 to 4-51);

b11 is 1 or 2.

According to another embodiment, the compound represented by one of Formulas 21A to 21C may be represented by Formula 21C(4) or 21C(5).

<Formula 21C(4)> <Formula 21C(5)>

In Formulas 21C(4) and 21C(5), Cz ₁ and Cz ₃ are a group represented by Formula 22E or a group represented by Formula 22F.

The compound represented by Formulas 21A to 21C may be one of the following compounds (21)-1 to (21)-76, but is not limited thereto:

Formulas 21A and 21B necessarily include at least one group represented by one of Formulas 22A and 22B, and Formula 21C has a core substantially similar to Formulas 22A and 22B, and thus may have excellent thermal stability.

Meanwhile, Formula 21A necessarily includes an electron transporting moiety as described herein (eg, see Formulas 4-1 to 4-51), and at least one of rings B ₁ and B ₂ of Formula 21B must contain at least one nitrogen as a ring-forming atom, and formula 21C must have an electron transporting moiety as defined herein in the molecule, or must contain a group represented by at least one of formulas 22E and 22F in the molecule Thus, the compound represented by one of Formulas 21A to 21C may have excellent bipolar properties and high T ₁ energy level, and thus may be usefully used as a material for an electric device, for example, an organic light emitting device. For example, the compound represented by one of Formulas 21A to 21C may be usefully used as a host material for an organic light emitting device.

For example, HOMO, LUMO, T for the compounds (21)-2 to (21)-19 and (21)-21 to (21)-76 and the following compounds (21)-A and (21)-B The results of simulation evaluation using Gaussian for ₁ energy level and S ₁ energy level are shown in Table 2 below:

<Compound (21)-A> <Compound (21)-B>

From Table 2, compounds (21)-2 to (21)-19 and (21)-21 to (21)-76 have lower LUMO levels (i.e., compounds (21)-A and (21)-B compared to compounds (21)-A and (21)-B. , large absolute value of LUMO), the condensed cyclic compound represented by one of Formulas 21A to 21C in the following compounds (21)-A and (21)-B is an organic layer material of an organic light emitting device, for example , it can be confirmed that it is suitable for use as a material for an auxiliary layer or a light emitting layer.

A method for synthesizing the condensed cyclic compound represented by one of Formulas 21A to 21C may be readily recognized by those skilled in the art with reference to the following synthesis examples.

Formulas 31A and 31B

<Formula 31A> <Formula 31B>

ㅂ

hundred

Ring A in Formulas 31A and 31B is a C ₁ -C ₂₀ heterocyclic group containing at least two N as ring-forming atoms. The C ₁ -C ₂₀ heterocyclic group may be a 6-membered ring, a 6-membered ring to which a 6-membered ring is condensed, or a 6-membered ring to which a 5-membered ring is condensed.

For example, ring A in Formulas 31A and 31B may be a C ₁ -C ₂₀ heterocyclic group including at least 3 N as ring-forming atoms.

According to one embodiment, ring A in Formulas 31A and 31B may be selected from Formulas 32-1 to 32-8, but is not limited thereto:

For the description of R _9a to R _9e in Formulas 32-1 to 32-8, refer to the description of R ₉ described in Formulas 31A and 31B independently of each other, and * denotes a bonding site with a neighboring atom.

According to one embodiment, ring A in Formulas 31A and 31B may be represented by one of Formulas 32-1, 32-5, and 32-8, but is not limited thereto.

According to another embodiment, ring A in Formulas 31A and 31B may be represented by one of Formulas 32-1 to 32-4, but is not limited thereto.

In Formulas 31A and 31B, L ₁ , L ₂ , L ₁₁ and L ₁₂ may each independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group , 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 It may be selected from a C ₁ -C ₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.

For example, in Formulas 31A and 31B, L ₁ , L ₂ , L ₁₁ and L ₁₂ are each independently

phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acetonitrile Naphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group (fluoranthrenylene), triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenyl pentaphenylene, hexacenylene, pyrrolylene, imidazolylene, pyrazolylene, pyridinylene, pyrazinylene, pyrimidi Nylene group (pyrimidinylene), pyridazinylene group (pyridazinylene), isoindolylene group (isoindolylene), indolylene group (indolylene), indazolylene group (indazolylene), purinylene group (purinylene), quinolinylene group (quinolinylene) , isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene , cinnolinylene, carbazolylene, phenanthridinylen e), acridinylene group, phenanthrolinylene group, phenazinylene group, benzooxazolylene group, benzoimidazolylene group, furanylene group, Benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group (isoxazolylene), oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzothiophenylene group ), a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene 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, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a C ₆ -C ₂₀ aryl group, and a C ₁ -C ₆₀ heteroaryl group substituted with at least one of a phenylene group, a pentalenylene group, an indenyl group Rene group, naphthylene group, azulenylene group, heptalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, Fluoranthrenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pyrrolylene group, imidazolylene group, pyra Zolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, isoindolylene group, indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzo Quinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinolinylene group, carbazolylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phena Zinylene group, benzoxazolylene group, benzoimidazolylene group, furanylene group, benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group , oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group imidazopyrimidinylene group and an imidazopyridinylene group; and

Formulas 33-1 to 33-6; can be selected from

In Formulas 33-1 to 33-6, Z ₁₁ to Z ₁₆ , Q ₁ and Q ₂ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, 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, C ₆ - selected from a C ₂₀ aryl group and a C ₁ -C ₆₀ heteroaryl group; * and *' are, independently of each other, binding sites with neighboring atoms.

According to another embodiment, in Formulas 31A and 31B, L ₁ , L ₂ , L ₁₁ and L ₁₂ are each independently selected from the group consisting of:

Phenylene group, naphthylene group, phenalenylene group, phenanthrenylene group, triphenylenylene group, anthracenylene group, pyrrolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, isoindolyl a lene group, an indolylene group, a furanylene group, a benzofuranylene group, a thiophenylene group, a benzothiophenylene group, and a triazinylene 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 ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, fluorenyl group, carbazolyl group, benzo Carbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, phthalazinyl group, quinoxalinyl group, cy phenylene group, naphthylene group, phenalenylene group, phenanthrenylene group, triphenylenylene group, anthracenylene group, pyrrolylene group, pyridinylene group, pyrazinylene group, pyri midinylene group, pyridazinylene group, isoindolylene group, indolylene group, furanylene group, benzofuranylene group, thiophenylene group, benzothiophenylene group and triazinylene group; and

Formulas 33-1 to 33-6; may be selected from, but is not limited thereto. Here, in Formulas 33-1 to 33-6, Q ₁ and Q ₂ in Z ₁₁ to Z ₁₆ and -Si(Q ₁ )(Q ₂ )- 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, C ₁ -C ₂₀ Alkyl group, C ₁ -C ₂₀ Alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazole Diyl, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, phthalazinyl group, quinoxalinyl group, cinolinyl group and quinazolinyl group selected from can be

For example, in Formulas 31A to 31B, L ₁ , L ₂ , L ₁₁ and L ₁₂ may be each independently selected from Formulas 34-1 to 34-15 and Formulas 33-1 to 33-6, It is not limited to:

In Formula 31A, a1 represents the number of L ₁ , and may be selected from an integer of 0 to 3. For example, a1 may be 0, 1, or 2. When a1 is 0, R ₁ is directly connected to "N" of the carbazole. When a1 is 2 or more, two or more L ₁ may be the same as or different from each other. For the description of a2, a3 and a4, refer to the description of a1 and the structures of Formulas 31A and 31B.

In Formulas 31A and 31B, a1, a2, a3, and a4 may each independently be 0, 1, or 2, but is not limited thereto.

In Formulas 31A and 31B, R ₁ to R ₉ and R ₁₁ to R ₁₈ may each independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ Alkenyl group, 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 group It may be selected from a condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heterocondensed polycyclic group, and -Si(Q ₁ )(Q ₂ )(Q ₃ ).

For example, in Formulas 31A and 31B,

R ₁ and R ₁₁ are each independently, a substituted or unsubstituted C ₆ -C ₂₀ aryl group, a substituted or unsubstituted C ₁ -C ₂₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group , a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group and -Si(Q ₁ )(Q ₂ )(Q ₃ );

R ₂ to R ₉ and R ₁₂ to R ₁₈ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group , hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted substituted 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 heterocyclo Alkenyl group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C ₁ -C ₂₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted 1 is selected from a non-aromatic condensed heteropolycyclic group and -Si(Q ₁ )(Q ₂ )(Q ₃ ),

At least one of R ₅ to R ₈ is a substituted or unsubstituted C ₆ -C ₂₀ aryl group, a substituted or unsubstituted C ₁ -C ₂₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and It may be selected from a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

According to another embodiment, in Formulas 31A and 31B,

R ₁ to R ₉ and R ₁₁ to R ₁₈ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof , a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group ), fluorenyl group (fluorenyl), spiro-fluorenyl group, phenalenyl group (phenalenyl), phenanthrenyl group (phenanthrenyl), anthracenyl group (anthracenyl), fluoranthrenyl group (fluoranthrenyl), triphenylenyl group ( triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl , pyrrolyl group (pyrrolyl), imidazolyl group (imidazolyl), pyrazolyl group (pyrazolyl), pyridinyl group (pyridinyl), pyrazinyl group (pyrazinyl), pyrimidinyl group (pyrimidinyl), pyridazinyl group (pyridazinyl), isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, purinyl Thalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthridinyl group, Acridinyl, phenanthrolinyl, phenazinyl, benzooxazolyl, benzoimidazolyl, furanyl, benzofuranyl, thiophenyl group nyl), benzothiophenyl, thiazolyl, isothiazolyl, benzothiazolyl, isoxazolyl, oxazolyl, triazole Diyl, tetrazolyl group, oxadiazolylene, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imida a pyridimidinyl group and an imidazopyridinyl 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 ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthr Nyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group , phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, substituted with at least one of phthalazinyl group, quinoxalinyl group, cinolinyl group and quinazolinyl group , fluorenyl group, spiro-fluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pyrrolyl group, imidazolyl group, pyrazolyl 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, benzooxazolyl group, benzoimidazolyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazole diary, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, and imidazopyridinyl group; and

-Si(Q ₁ )(Q ₂ )(Q ₃ ); is selected from;

Wherein Q ₁ To Q ₃ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, Fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group phthala selected from a zinyl group, a quinoxalinyl group, a cinolinyl group, and a quinazolinyl group;

At least one of R ₅ to R ₈ is,

Phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group , fluoranthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, pyri Dinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthi Lidinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoxazolyl group, benzoimidazolyl group, furanyl group, benzo furanyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyrimidinyl group and an imidazopyridinyl 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 ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthr Nyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group , phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, substituted with at least one of phthalazinyl group, quinoxalinyl group, cinolinyl group and quinazolinyl group , fluorenyl group, spiro-fluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pyrrolyl group, imidazolyl group, pyrazolyl 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, benzooxazolyl group, benzoimidazolyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazole diary, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, and imidazopyridinyl group; is selected from;

R ₁ and R ₁₁ are, independently of each other,

Phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group , fluoranthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, pyri Dinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthi Lidinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoxazolyl group, benzoimidazolyl group, furanyl group, benzo furanyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyrimidinyl group and an imidazopyridinyl 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 ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthr Nyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group , phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, substituted with at least one of phthalazinyl group, quinoxalinyl group, cinolinyl group and quinazolinyl group , fluorenyl group, spiro-fluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pyrrolyl group, imidazolyl group, pyrazolyl 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, benzooxazolyl group, benzoimidazolyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazole diary, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, and imidazopyridinyl group; and

-Si(Q ₁ )(Q ₂ )(Q ₃ ); may be selected from, but is not limited thereto.]

According to another embodiment, in Formulas 31A and 31B,

R ₁ and R ₁₁ are each independently of the following formulas 35-1 to 35-40 and -Si(Q ₁ )(Q ₂ )(Q ₃ ) (wherein Q ₁ to Q ₃ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, Dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group phthalazinyl group, quinoxalinyl group, cinolinyl group and quinazolyl group nyl group);

R ₂ to R ₄ and R ₁₁ to R ₁₄ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine a group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

R ₅ to R ₉ and R ₁₅ to R ₁₈ 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, and Formulas 35-1 to 35-40;

At least one of R ₅ to R ₈ and at least one of R ₁₅ to R ₁₈ are each independently selected from the following formulas 35-1 to 35-40,

At least one of b2 R ₉ may be selected from the following Chemical Formulas 35-1 to 35-40, but is not limited thereto:

In Formulas 35-1 to 35-40,

Z ₁ to Z ₃ 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 Acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naph Tyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinolinyl group, and a quinazolinyl group;

d1 is 1 or 2, d2 is selected from an integer from 1 to 3, d3 is selected from an integer from 1 to 4, d4 is selected from an integer from 1 to 5, d5 is selected from an integer from 1 to 6, , d6 is selected from an integer from 1 to 7, d7 is selected from an integer from 1 to 8, and d8 is selected from an integer from 1 to 9;

* is a binding site with a neighboring atom.

According to another embodiment, in Formulas 31A and 31B,

R ₁ to R ₈ and R ₁₁ to R ₁₈ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof , a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

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, and a phosphoric acid group or a salt thereof, substituted with at least one selected from a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a phenylenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl 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 ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, phenylenyl group, fluorenyl group, carbazolyl group, dibenzo A phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a phenylenyl group, a fluorenyl group, a carbazolyl group, and a dibenzo a furanyl group and a dibenzothiophenyl group; and

-Si(Q ₁ )(Q ₂ )(Q ₃ ) (wherein Q ₁ to Q ₃ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, Anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyrida selected from a zinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinolinyl group, and a quinazolinyl group); is selected from;

At least one of R ₅ to R ₈ and at least one of R ₁₅ to R ₁₈ are, independently of each other,

a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a phenylenyl group, a fluorenyl group, a carbazolyl 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 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, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, phenylenyl group, fluorenyl group, carbazolyl group, dibenzo A phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a phenylenyl group, a fluorenyl group, a carbazolyl group, and a dibenzo a furanyl group and a dibenzothiophenyl group; may be selected from, but is not limited thereto.

In Formulas 31A and 31B, b1 represents the number of R ₁ , and may be selected from an integer of 1 to 5. For example, b1 may be 1 or 2.

In Formulas 31A and 31B, b2 represents the number of R ₉ and may be selected from an integer of 1 to 5. For example, b2 may be 1 or 2.

In Formula 31B, b3 represents the number of R ₁₁ and may be selected from an integer of 1 to 5. For example, b3 may be 1 or 2.

According to one embodiment, at least one of b2 R ₉ in Formulas 31A and 31B is a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or It may be selected from an unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

For example, at least one of R _9a and R _9b in Formula 32-1, at least one of R _9a to R _9c in Formulas 32-2 to 32-5 and 32-8, and Formula 32-6 and 32- At least one of R _9a to R _9e of 7 is a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensation It may be selected from a polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

For example, b1, b2, and b3 of Formulas 31A and 31B may be 1, but is not limited thereto.

In Formula 31B, L ₁ = L ₁₁ , L ₂ = L ₁₂ , a1 = a3, a2 = a4, R ₁ = R ₁₁ , R ₂ = R ₁₂ , R ₃ = R ₁₃ , R ₄ = R ₁₄ , R ₅ = R ₁₅ , R ₆ = R ₁₆ , R ₇ = R ₁₇ , R ₈ = R ₁₈ , b1 = b3 , but is not limited thereto.

According to one embodiment, the compound represented by Formula 31A or 31B is represented by Formula 31A, wherein in Formula 31A, a1 is 0; R ₁ is selected from Formulas 35-1 to 35-40 (eg, R ₁ may be represented by Formula 35-1); b1 is 1; R ₂ to R ₆ and R ₈ are hydrogen; R ₇ is selected from Formulas 35-1 to 35-40 (eg, R ₇ may be represented by Formula 35-40); a2 is 0 or 1; L ₂ is selected from Formulas 34-1 to 34-15 (eg, L ₂ may be represented by Formula 34-2); Ring A may be selected from Formula 32-1 (herein, R _9a and R _9b in Formula 32-1 may be each independently selected from Formulas 35-1 to 35-40, for example, Formula 32-1 Among them, R _9a and R _9b may be represented by Formula 35-1).

According to another embodiment, the compound represented by Formula 31A or 31B is represented by Formula 31A, wherein in Formula 31A, a1 is 0; R ₁ is represented by Formula 35-1; b1 is 1; R ₂ to R ₆ and R ₈ are hydrogen; R ₇ is represented by Formula 35-40; a2 is 0 or 1; L ₂ is represented by Formula 34-2; Ring A may be represented by Formula 32-1 (wherein R _9a and R _9b in Formula 32-1 are represented by Formula 35-1).

The compound represented by Formulas 31A and 31B may be one of the following compounds (31)-1 to (31)-130, but is not limited thereto:

At least one of R ₅ to R ₈ in Formulas 31A and 31B is “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 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, and a substituted or unsubstituted monovalent non- aromatic heterocondensed polycyclic group". Accordingly, the steric hindrance effect of the carbazole-based compound represented by Formula 31A or 31B may be increased, and aggregation of the carbazole-based compound may be inhibited. Accordingly, the luminous efficiency of the organic light emitting diode including the compound represented by Formula 31A or 31B may be improved.

In addition, the compound represented by Formula 31A or 31B includes a "carbazole-based ring" (for example, refer to Formula 31A' below), used as a material for an organic light emitting device (eg, a host material in the emission layer) It may have an energy band gap range suitable for:

<Formula 31A'>

On the other hand, the compound represented by Formula 31A or 31B does not include "amino group and derivatives thereof" in the molecule. "Amino group and its derivatives" may have poor thermal stability and electrical stability with respect to electron transfer, and may cause difficulty in controlling an energy level suitable for a host material of an organic light emitting device, thereby reducing luminous efficiency. However, the compound represented by Formula 31A or 31B is designed not to include an “amino group and derivatives thereof” in the molecule, and the compound represented by Formula 31A or 1B is a material for an organic light emitting device (eg, in the light emitting layer). host material) and have a suitable energy band gap range.

Furthermore, in the compound represented by Formula 31A or 31B, "Ring A" is connected to the "4th carbon" of the carbazole ring in Formulas 31A and 31B (see Formula 31A'), and is represented by Formula 31A or 31B. Separation of the HOMO region and the LUMO region among the displayed compounds may be effectively performed. Accordingly, the compound represented by Formula 31A or 31B may have a high T1 energy level.

A method for synthesizing the carbazole-based compound represented by Formula 31A or 31B may be readily recognized by those skilled in the art with reference to the following synthesis examples.

Formula 41

<Formula 41>

<Formula 42A> <Formula 42B>

<Formula 42C> <Formula 42D>

<Formula 42E> <Formula 42F>

<Formula 41A> <Formula 41B>

Ring A ₁₁ in Formula 41 is represented by Formula 41A. The ring A ₁₁ is fused to each other while sharing a carbon atom with each of the adjacent 5-membered ring and ring A ₁₂ in Formula 41.

Ring A ₁₂ in Formula 41 is represented by Formula 41B. The ring A ₁₂ is fused to each other while sharing a carbon atom with each of the ring A ₁₂ and the adjacent 6-membered ring in Formula 41.

In Formula 41, X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], S, O, S(=O), S(=O) ₂ , C(=O), C(R ₁₃ ) )(R ₁₄ ), Si(R ₁₃ )(R ₁₄ ), P(R ₁₃ ), P(=O)(R ₁₃ ), or C=N(R ₁₃ ), and in Formula 1B, X ₁₂ is N— [(L ₁₂ ) _a12 -(R ₁₂ ) _b12 ], S, O, S(=O), S(=O) ₂ , C(=O), C(R ₁₅ )(R ₁₆ ), Si(R ₁₅ )(R ₁₆ ), P(R ₁₅ ), P(=O)(R ₁₅ ), or C=N(R ₁₅ ), wherein X ₁ in Formulas 2A to 2F is N-[(L ₁ ) _a1- (R ₁ ) _b1 ], S, O, S(=O), S(=O) ₂ , C(=O), Si(R ₅ )(R ₆ ), P(R ₅ ), P(=O) )(R ₅ ) or C=N(R ₅ ).

The relationship between Formula 41 and Formulas 42A to 42F is as follows:

i) In Formula 41, when X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ] and X ₁₂ is not N-[(L ₁₂ ) _a12 -(R ₁₂ ) _b12 ], at least one of R ₁₁ and R ₂₁ to R ₃₀ in b11 of 41 is selected from the group represented by Formula 42A to the group represented by Formula 42F;

ii) In Formula 41, when X ₁₁ is not N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ] and X ₁₂ is N-[(L ₁₂ ) _a12 -(R ₁₂ ) _b12 ], at least one of R ₁₂ and R ₂₁ to R ₃₀ in b12 of 41 is selected from the group represented by Formula 42A to the group represented by Formula 42F;

iii) In Formula 41, when X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ] and X ₁₂ is N-[(L ₁₂ ) _a12 -(R ₁₂ ) _b12 ], Formula 41 At least one of b11 R ₁₁ , b12 R ₁₂ , and R ₂₁ to R ₃₀ is selected from the group represented by Formula 42A to the group represented by Formula 42F.

According to one embodiment, X ₁₁ in Formula 41 may be N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], S or O.

According to another embodiment, X ₁₂ in Formula 41B may be N-[(L ₁₂ ) _a12 -(R ₁₂ ) _b12 ], S or O.

According to another embodiment, in Formulas 42A to 42F, X ₁ may be N-[(L ₁ ) _a1- (R ₁ ) _b1 ], S or O.

In Formulas 41 and 41B, X ₁₁ and X ₁₂ may be the same as or different from each other.

In the above formulas, L ₁ to L ₄ , L ₁₁ and L ₁₂ 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 an unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ arylene group, a substituted or unsubstituted C ₁ It may be selected from a -C ₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.

For example, in Formulas 41, 41A, 41B, and 42A to 42F, L ₁ to L ₄ , L ₁₁ and L ₁₂ are independently of each other,

phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acetonitrile Naphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group (fluoranthrenylene), triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenyl pentaphenylene, hexacenylene, pyrrolylene, imidazolylene, pyrazolylene, pyridinylene, pyrazinylene, pyrimidi Nylene group (pyrimidinylene), pyridazinylene group (pyridazinylene), isoindolylene group (isoindolylene), indolylene group (indolylene), indazolylene group (indazolylene), purinylene group (purinylene), quinolinylene group (quinolinylene) , isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene , cinnolinylene, carbazolylene, phenanthridinylen e), acridinylene group, phenanthrolinylene group, phenazinylene group, benzooxazolylene group, benzoimidazolylene group, furanylene group, Benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group (isoxazolylene), oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzothiophenylene group ), a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene 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, C ₆ -C ₂₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, and inda, which is substituted with at least one of a heterocondensed ring group, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) Cenylene group, acenaphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group, triphenylenylene group, pyrenylene group, cry Cenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pyrrolylene group, imidazolylene group, pyrazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, Pyridazinylene group, isoindolylene group, indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinox Salinylene group, quinazolinylene group, cinolinylene group, carbazolylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoxazolylene group, benzoimidazolylene group, furanyl Ren group, benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group, oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolyl a ren group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene group; is selected from

Q ₃₃ to Q ₃₅ are each independently, hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazole Diary, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, phthalazinyl group, quinoxali group It may be selected from a nyl group, a cinolinyl group, and a quinazolinyl group.

According to one embodiment, L ₁ to L ₄ , L ₁₁ and L ₁₂ in Formulas 41, 41A, 41B, and 42A to 42F may be each independently represented by one of Formulas 42-1 to 42-13, Not limited to:

In Formulas 42-1 to 42-13,

Z ₁ to Z ₄ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl group Acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, triphenylenyl group, pyrenyl group, phenanthree Nyl group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group , an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a biphenyl group, and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ );

wherein Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, cry Cenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quina selected from a jolinyl group and a quinoxalinyl group;

d1 is an integer from 1 to 4, d2 is an integer from 1 to 3, d3 is an integer from 1 to 6, d4 is an integer from 1 to 8, d6 is from 1 to 5 It is selected from integers, and * and *' may be binding sites with neighboring atoms.

According to another embodiment, L ₁ to L ₄ , L ₁₁ and L ₁₂ in Formulas 41, 41A, 41B, and 42A to 42F may be each independently represented by one of Formulas 43-1 to 43-12, It is not limited to:

In Formulas 42A to 42F, a1 represents the number of L ₁ , and is selected from an integer of 0 to 3. For example, a1 may be 0 or 1. When a1 is 0, R ₁ is directly connected to N. When a1 is 2 or more, two or more L ₁ may be the same as or different from each other. For the description of a2 to a4, a11 and a12, refer to the description of a1 and the description of Chemical Formulas 41 and 42A to 42F.

According to an embodiment, in Formulas 41, 41A, 41B, and 42A to 42F, a1 to a4, a11 and a12 may each independently be 0 or 1.

In Formulas 41, 41A, 41B, and 42A to 42F, R ₁ to R ₆ , R ₁₁ to R ₁₆ and R ₂₁ to R ₃₀ are each independently selected from hydrogen, deuterium, -F (fluoro group), -Cl (chloro group) group), -Br (bromo group), -I (iodo group), hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof , phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, 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 monovalent non-aromatic condensed heteropolycyclic group, -N ( Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), and the group represented by Formula 42A to the group represented by Formula 42F Optionally, R ₁ to R ₆ are not the group represented by Formula 42A or the group represented by Formula 42F.

According to one embodiment, in Formulas 41, 41A, 41B, and 42A to 42F, R ₁ to R ₆ , R ₁₁ to R ₁₆ and R ₂₁ to R ₃₀ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of salts thereof;

A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group ), fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group (phenalenyl), phenanthrenyl group (phenanthrenyl), anthracenyl group, fluoran Tenyl group (fluoranthenyl), triphenylenyl group (triphenylenyl), pyrenyl group (pyrenyl), chrysenyl group (chrysenyl), naphthacenyl group (naphthacenyl), picenyl group (picenyl), perylenyl group (perylenyl), penta Phenyl group (pentaphenyl), hexacenyl group (hexacenyl), pentacenyl group (pentacenyl), rubicenyl group (rubicenyl), coronenyl group (coronenyl), ovalenyl group (ovalenyl), pyrrolyl group (pyrrolyl), thiophenyl group ), furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl , pyridinyl group, pyrazinyl group (pyrazinyl), pyrimidinyl group (pyrimidinyl), pyridazinyl group (pyridazinyl), isoindolyl group (isoindolyl), indolyl group (indolyl), indazolyl group (indazolyl), Purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl , quinazolinyl group, cinnolinyl group, carbazolyl group ( carbazolyl), phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl (benzothiophenyl), isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl ), triazinyl group, dibenzofuranyl group (dibenzofuranyl), dibenzothiophenyl group (dibenzothiophenyl), benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, hep Thalenyl 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, 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, iso Indolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazole Diary, phenantridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group , tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl and biphenyl group At least one substituted, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, di benzofluorenyl 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, thiazolyl 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, phenane Tridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazole diary, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl group;

-Si(Q ₃ )(Q ₄ )(Q ₅ ), provided that R ₁₃ to R ₁₆ and R ₅ and R ₆ are not -Si(Q ₃ )(Q ₄ )(Q ₅ ); and

a group represented by Formula 42A to a group represented by Formula 42F (provided that R ₁ to R ₆ are not the group represented by Formula 42A or a group represented by Formula 42F); is selected from;

wherein Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group , fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, It may be selected from an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group, but is not limited thereto.

According to another embodiment, in Formulas 41, 41A, 41B, and 42A to 42F, R ₁ to R ₆ , R ₁₁ to R ₁₆ and R ₂₁ to R ₃₀ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of salts thereof;

Formulas 44-1 to 44-31 below;

-Si(Q ₃ )(Q ₄ )(Q ₅ ), provided that R ₁₃ to R ₁₆ and R ₅ to R ₆ are not -Si(Q ₃ )(Q ₄ )(Q ₅ ); and

the group represented by Formula 42A to the group represented by Formula 42F (provided that R ₁ to R ₆ are not the group represented by Formula 42A or the group represented by Formula 42F); may be selected from, but not limited to:

In Formulas 44-1 to 44-31,

Y ₃₁ is O, S, C(Z ₃₃ )(Z ₃₄ ), N(Z ₃₅ ), or Si(Z ₃₆ )(Z ₃₇ ) (provided that Y ₃₁ in Formulas 44-23 is not NH);

Z ₃₁ to Z ₃₇ 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 Acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, triphenylenyl group, pyrenyl group, phenanthree Nyl group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group , an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a biphenyl group, and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ); is selected from

wherein Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, triphenylenyl group, pyrethane Nyl group, phenanthrenyl group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group , is selected from a quinolinyl group, an isoquinolinyl group, a quinazolinyl group and a quinoxalinyl group;

e1 is selected from an integer from 1 to 5, e2 is selected from an integer from 1 to 7, e3 is selected from an integer from 1 to 3, e4 is selected from an integer from 1 to 4, e5 is 1 or 2; , e6 is selected from an integer of 1 to 6, and * is a binding site with a neighboring atom.

According to another embodiment, in Formulas 41, 41A, 41B and 42A to 42F, R ₁ to R ₆ , R ₁₁ to R ₁₆ and R ₂₁ to R ₃₀ are each independently selected from the group consisting of:

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of salts thereof;

Formulas 45-1 to 45-63 below;

-Si(Q ₃ )(Q ₄ )(Q ₅ ) (provided that R ₁₃ to R ₁₆ , R ₅ and R ₆ are not -Si(Q ₃ )(Q ₄ )(Q ₅ ); and

a group represented by Formula 42A to a group represented by Formula 42F (provided that R ₁ to R ₆ are not a group represented by Formula 42A or a group represented by Formula 42F); may be selected from, but not limited to:

On the other hand, at least one of R ₂ of Formulas 42A and 42B, R ₃ of Formulas 42C and 42D, and R ₂ and R ₃ of Formulas 42E and 42F,

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, penta Cenyl 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, pyri Dinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthi Ridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, iso Benzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzo a carbazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, hep Thalenyl 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, 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, iso Indolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazole Diary, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, tria Zolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and non substituted with at least one of phenyl, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group , dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, penta Phenyl group, hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thi Ophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindole Diary, 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, triazole diary, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl group; is selected from

wherein Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, cry Cenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quina It may be selected from a jolinyl group and a quinoxalinyl group.

For example, at least one of R ₂ of Formulas 42A and 42B, R ₃ of Formulas 42C and 42D, and R ₂ and R ₃ of Formulas 42E and 42F,

a phenyl group, a naphthyl group, a triphenylenyl group, a phenanthrenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, and a triazinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), phenyl group, naphthyl group, triphenylenyl group, phenanthrenyl group, pyridinyl group , pyrimidinyl group, pyrazinyl group, pyridazinyl group and at least one of triazinyl substituted, phenyl group, naphthyl group, triphenylenyl group, phenanthrenyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyrida zinyl and triazinyl; is selected from

The Q ₃₃ to Q ₃₅ are each independently selected from hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, and a naphthyl group.

According to another embodiment, at least one of R ₂ of Formulas 42A and 42B, R ₃ of Formulas 42C and 42D, and R ₂ and R ₃ of Formulas 42E and 42F is selected from Formulas 45-1 to 45-63. may be selected from, but is not limited thereto.

According to another embodiment, R ₁ in X ₁ in Formulas 42A to 42F, R ₁₁ in X ₁₁ in Formula 41, and R ₁₂ in X ₁₂ in Formula 41B are each independently of each other, 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 A substituted C ₆ -C ₂₀ aryl group, a substituted or unsubstituted C ₁ -C ₂₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic hetero condensed group a polycyclic group, or one of the group represented by Formula 42A to the group represented by Formula 42F, wherein R ₁ is not the group represented by Formula 42A to the group represented by Formula 42F.

For example, R ₁ in X ₁ in Formulas 42A to 42F, R ₁₁ in X ₁₁ in Formula 1, and R ₁₂ in X ₁₂ in Formula 41B are each independently selected from each other;

a phenyl group, a naphthyl group, a triphenylenyl group, a phenanthrenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group and a triazinyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), phenyl group, naphthyl group, triphenylenyl group, phenanthrenyl group, pyridinyl group , pyrimidinyl group, pyrazinyl group, pyridazinyl group and triazinyl group substituted with at least one, phenyl group, naphthyl group, triphenylenyl group, phenanthrenyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyri a dazinyl group and a triazinyl group; and

a group represented by Formula 42A to a group represented by Formula 42F; may be selected from, but is not limited thereto. Here, R ₁ is not a group represented by Formula 42A or a group represented by Formula 42F.

According to another embodiment, R ₄ in Formulas 42A to 42F may be each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group, and a C ₁ -C ₂₀ alkoxy group, but is not limited thereto. .

In Formulas 41, 41A, 41B, and 42A to 42F, b1 represents the number of R ₁ , and may be selected from an integer of 1 to 3. When b1 is 2 or more, two or more R ₁ may be the same as or different from each other. For the description of b2 to b4, b11 and b12, refer to the description of b1 and the structures of Formulas 41 and 42A to 42F.

According to another embodiment, the condensed cyclic compound represented by Formula 41 may be represented by one of Formulas 41-1 to 41-6 below:

Descriptions of X ₁₁ , X ₁₂ , and R ₂₁ to R ₃₀ in Formulas 41-1 to 41-6 are the same as those of Formula 41.

For example, in Formulas 41-1 to 41-6,

X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], S or O;

X ₁₂ is N-[(L ₁₂ ) _a12 -(R ₁₂ ) _b12 ], S or O;

X ₁ is N-[(L ₁ ) _a1- (R ₁ ) _b1 ], S or O;

i) In Formulas 41-1 to 41-6, X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], and X ₁₂ is N-[(L ₁₂ ) _a12 -(R ₁₂ ) _b12 ] if not, at least one of b11 R ₁₁ and R ₂₁ to R ₃₀ in Formula 41 is selected from the group represented by Formula 42A to the group represented by Formula 42F;

ii) In Formulas 41-1 to 41-6, X ₁₁ is not N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], and X ₁₂ is N-[(L ₁₂ ) _a12 -(R ₁₂ ) _b12 ], at least one of b12 R ₁₂ and R ₂₁ to R ₃₀ in Formula 41 is selected from the group represented by Formula 42A to the group represented by Formula 42F;

iii) In Formulas 41-1 to 41-6, X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], and X ₁₂ is N-[(L ₁₂ ) _a12 -(R ₁₂ ) _b12 ] , at least one of b11 R ₁₁ , b12 R ₁₂ , and R ₂₁ to R ₃₀ in Formula 1 is selected from the group represented by Formula 42A to the group represented by Formula 42F;

wherein L ₁ to L ₄ , L ₁₁ and L ₁₂ are each independently selected from Formulas 42-1 to 42-13 (eg, Formulas 43-1 to 43-12);

a1 to a4, a11 and a12 are each independently 0 or 1;

The R ₁ , R ₁₁ and R ₁₂ are independently of each other,

a phenyl group, a naphthyl group, a triphenylenyl group, a phenanthrenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group and a triazinyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), phenyl group, naphthyl group, triphenylenyl group, phenanthrenyl group, pyridinyl group , pyrimidinyl group, pyrazinyl group, pyridazinyl group and at least one of triazinyl substituted, phenyl group, naphthyl group, triphenylenyl group, phenanthrenyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyrida a zinyl group and a triazinyl group; and

a group represented by Formula 42A to a group represented by Formula 42F; selected from (provided that R ₁ is not a group represented by Formula 42A to a group represented by Formula 42F);

At least one of R ₂ and R ₃ is,

a phenyl group, a naphthyl group, a triphenylenyl group, a phenanthrenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group and a triazinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), phenyl group, naphthyl group, triphenylenyl group, phenanthrenyl group, pyridinyl group , pyrimidinyl group, pyrazinyl group, pyridazinyl group and at least one of triazinyl substituted, phenyl group, naphthyl group, triphenylenyl group, phenanthrenyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyrida a zinyl group and a triazinyl group; is selected from;

R ₄ is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

R ₂₁ to R ₃₀ are each independently,

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of salts thereof;

Formulas 44-1 to 44-31 (eg, one of Formulas 5-1 to 5-63);

-Si(Q ₃ )(Q ₄ )(Q ₅ ) ; and

a group represented by Formula 42A to a group represented by Formula 42F (provided that R ₁ to R ₆ are not a group represented by Formula 42A or a group represented by Formula 42F); may be selected from, but is not limited thereto.

According to one embodiment, the condensed cyclic compound represented by Formula 41 is

i) represented by Formulas 41-1 or 41-2, and R ₂₁ in Formulas 41-1 and 41-2 is selected from the group represented by Formula 42A to the group represented by Formula 42F,

ii) represented by Formula 41-1 or 41-6, in Formulas 41-1 and 41-6, X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], and R ₁₁ is Formula 42A It may be selected from the group represented by to the group represented by Formula 42F.

According to another embodiment, the compound represented by Formula 41 is

i) In Formula 41, when X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ] and X ₁₂ is not N-[(L ₁₂ ) _a12 -(R ₁₂ ) _b12 ], At least one of R ₁₁ and R ₂₁ to R ₃₀ in b11 of 41 is a group represented by Formula 42A, a group represented by Formula 42B, a group represented by Formula 42D, and a group represented by Formula 42F-1 is selected from;

ii) In Formula 41, when X ₁₁ is not N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ] and X ₁₂ is N-[(L ₁₂ ) _a12 -(R ₁₂ ) _b12 ], At least one of R ₁₂ and R ₂₁ to R ₃₀ of b12 in 41 is a group represented by Formula 42A, a group represented by Formula 42B, a group represented by Formula 42D, and a group represented by Formula 42F-1 is selected from;

iii) In Formula 41, when X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ] and X ₁₂ is N-[(L ₁₂ ) _a12 -(R ₁₂ ) _b12 ], Formula 41 At least one of b11 R ₁₁ , b12 R ₁₂ , and R ₂₁ to R ₃₀ is selected from the group represented by Formula 42A, the group represented by Formula 42B, the group represented by Formula 42D, and Formula 42F-1 It may be a condensed cyclic compound selected from the group represented by:

<Formula 42F-1>

For the description of Formula 42F-1, refer to the description of Formula 42F described herein.

The compound represented by Formula 41 may be one of the following compounds (41)-1 to (41)-40, but is not limited thereto:

The compound represented by Formula 41 necessarily includes at least one selected from the group represented by Formula 42A to the group represented by Formula 42F. In the core of Formulas 42A to 42F, "pyrimidine" is fused to one side of a 5-membered ring, and by the "pyrimidine", which is an electron-withdrawing group, the compound represented by Formula 41 has electron injection and transport properties. can be improved

Table 3 below is data obtained by evaluating the HOMO energy level, LUMO energy level, and T1 energy level of some of the compounds and the following compound (41)-A using Gaussian. The following compound (41)-A has a group in which "pyridine" is fused to one side of a thiophene ring.

<Compound (41)-A>

From Table 3, the LUMO level of compound (41)-A is compound (41)-1, (41)-2, (41)-21, (41)-22, (41)-25, (41) higher than the LUMO levels of -4, (41)-3, (41)-24, (41)-23, (41)-27, (41)-28 and (41)-35 (i.e., the compound ( The absolute LUMO level of 41)-A is compound (41)-1, (41)-2, (41)-21, (41)-22, (41)-25, (41)-4, (41) -3, (41)-24, (41)-23, (41)-27, (41)-28 and (41)-35 are smaller than the absolute value of the LUMO level compared to ), the compound (41)- 1, (41)-2, (41)-21, (41)-22, (41)-25, (41)-4, (41)-3, (41)-24, (41)-23, It can be seen that the condensed cyclic compound represented by Chemical Formula 41, such as (41)-27, (41)-28, and (41)-35, has better electron transport properties than the compound (41)-A.

Therefore, when the condensed cyclic compound represented by Formula 41 is used as an organic layer material of an organic light emitting device, for example, a light emitting layer material of an organic light emitting device (eg, a host in the light emitting layer of an organic light emitting device), effective charge transport balance can be achieved, and an organic light emitting device having improved luminous efficiency can be realized.

A method for synthesizing the condensed cyclic compound represented by Formula 41 can be easily recognized by those skilled in the art with reference to the following synthesis examples.

Formulas 51A and 51B

<Formula 51A>

<Formula 51B>

Ring A ₁ in Formulas 51A and 51B is represented by Formula 51C.

<Formula 51C>

Ring A ₁ in Formulas 51A and 51B is a fused ring while sharing a carbon atom with two adjacent 6-membered rings.

Ring B ₁ in Formulas 51A and 51B is a C ₆ -C ₂₀ aromatic ring. The ring B ₁ is a ring fused to the ring A ₁ while sharing a carbon atom with the adjacent ring A ₁ .

For example, Ring B ₁ in Formulas 51A and 51B may be benzene, naphthalene, anthracene, or pyrene.

According to one embodiment, Ring B ₁ in Formulas 51A and 51B may be benzene or naphthalene.

In Formula 51C, X ₂₁ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ], S, O, S(=O), S(=O) ₂ , C(R ₂₂ )(R ₂₃ ), and Si(R ₂₂ )(R ₂₃ ). For example, in Formula 51C, X ₂₁ may be selected from N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ], S, O, and Si(R ₂₂ )(R ₂₃ ), but is limited thereto. not. For the description of L ₂₁ , a21 , R ₂₁ to R ₂₃ and b21, refer to the bar below.

In Formulas 51A and 51B, X ₁₁ is N or C-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], X ₁₂ is N or C-[(L ₁₂ ) _a12 -(R ₁₂ ) _b12 ], X ₁₃ is N or C-[(L ₁₃ ) _a13 -(R ₁₃ ) _b13 ], X ₁₄ is N or C-[(L ₁₄ ) _a14 -(R ₁₄ ) _b14 ], and among X ₁₁ to X ₁₄ At least one is N. For example, at least one of X ₁₂ and X ₁₃ in Formulas 51A and 51B may be N. The descriptions of L ₁₁ to L ₁₄ , a11 to a14 , R ₁₁ to R ₁₄ , and b11 to b14 refer to the bar below.

In Formulas 51A, 51B, and 51C, L ₁ to L ₃ , L ₁₁ to L ₁₄ and L ₂₁ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, 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, A substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed polycyclic group), and a substituted or unsubstituted divalent non-aromatic group It may be selected from a substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic group.

For example, in Formulas 51A, 51B, and 51C, L ₁ to L ₃ , L ₁₁ to L ₁₄ and L ₂₁ are each independently

phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acetonitrile Naphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group (fluoranthrenylene), triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenyl pentaphenylene, hexacenylene, pyrrolylene, imidazolylene, pyrazolylene, pyridinylene, pyrazinylene, pyrimidi Nylene group (pyrimidinylene), pyridazinylene group (pyridazinylene), isoindolylene group (isoindolylene), indolylene group (indolylene), indazolylene group (indazolylene), purinylene group (purinylene), quinolinylene group (quinolinylene) , isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene , cinnolinylene, carbazolylene, phenanthridinylen e), acridinylene group, phenanthrolinylene group, phenazinylene group, benzooxazolylene group, benzoimidazolylene group, furanylene group, Benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group (isoxazolylene), oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzothiophenylene group ), a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene 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, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group , chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenyl group-substituted carbazolyl group , phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenyl group-substituted benzocarbazolyl group, phenyl group-substituted dibenzo A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, substituted with at least one of a carbazolyl group, an imidazopyrimidinyl group, an imidazopyridinyl group, and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) , azulenylene group, heptalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group , triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pyrrolylene group, imidazolylene group, pyrazolylene group, pyridinyl Ren group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, isoindolylene group, indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinolinylene group, carbazolylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoxa Zolylene group, benzoimidazolylene group, furanylene group, benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group, oxazolylene group, Triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofura a nylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene group; is selected from

The Q ₃₃ to Q ₃₅ 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 car Acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, tri Phenylenyl group, pyrenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group , a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group, but is not limited thereto.

For example, in Formulas 51A, 51B, and 51C, L ₁ to L ₃ , L ₁₁ to L ₁₄ and L ₂₁ may be each independently selected from Formulas 52-1 to 52-34:

In Formulas 52-1 to 52-34,

Y ₁ is O, S, S(=O), S(=O) ₂ , C(Z ₃ )(Z ₄ ), N(Z ₅ ), or Si(Z ₆ )(Z ₇ );

Z ₁ To Z ₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl group an acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, Phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group , carbazolyl group, phenyl group-substituted carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenyl group-substituted a benzocarbazolyl group, a phenyl group-substituted dibenzocarbazolyl group, an imidazopyrimidinyl group, an imidazopyridinyl group, and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ );

The Q ₃₃ to Q ₃₅ 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 car Acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, tri Phenylenyl group, pyrenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group , a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyrimidinyl group and an imidazopyridinyl group;

d1 is an integer from 1 to 4; d2 is an integer from 1 to 3; d3 is an integer from 1 to 6; d4 is an integer from 1 to 8; d5 is 1 or 2; d6 is an integer from 1 to 5; * and *' are binding sites with neighboring atoms.

For example, in Formulas 52-1 to 52-34, * is a binding site with a core or a binding site with each of adjacent L ₁ to L ₃ , L ₁₁ to L ₁₄ and L ₂₁ in Formulas 51A or 51B, In 52-1 to 52-34, *' represents a binding site with each of the adjacent L ₁ to L ₃ , L ₁₁ to L ₁₄ and L ₂₁ , or R ₁ to R ₃ , R ₁₁ to R ₁₄ and R ₂₁ , respectively. binding site.

According to one embodiment, in Formulas 51A, 51B, and 51C, L ₁ to L ₃ , L ₁₁ to L ₁₄ and L ₂₁ may be each independently selected from Formulas 53-1 to 53-39, but limited thereto. It doesn't happen:

In Formulas 51A and 51B, a1 represents the number of L ₁ , and may be 0, 1, 2, 3, 4, or 5, for example, 0, 1, or 2, and as another example, may be 0 or 1. When a1 is 0, -(L ₁ ) _a1 - becomes a single bond. When a1 is 2 or more, two or more L ₁ may be the same as or different from each other. Descriptions of a2, a3, a11, a12, a13, and a14 are the same as those of a1.

In Formulas 51A, 51B, and 51C, R ₁ to R ₃ , R ₁₁ to R ₁₄ and R ₂₁ to R ₂₃ may each independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, and a hydroxyl group , cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, 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, A substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, 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 monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ) and -B(Q ₆ )(Q ₇ ). Here, the description of Q ₁ to Q ₇ will be described later.

For example, in Formulas 51A, 51B and 51C, R ₁ to R ₃ , R ₁₁ to R ₁₄ and R ₂₁ to R ₂₃ are each independently selected from each other,

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of salts thereof;

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹;A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group ), fluorenyl group (fluorenyl), spiro-fluorenyl group, phenalenyl group (phenalenyl), phenanthrenyl group (phenanthrenyl), anthracenyl group (anthracenyl), fluoranthrenyl group (fluoranthrenyl), triphenylenyl group ( triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl , pyrrolyl group (pyrrolyl), imidazolyl group (imidazolyl), pyrazolyl group (pyrazolyl), pyridinyl group (pyridinyl), pyrazinyl group (pyrazinyl), pyrimidinyl group (pyrimidinyl), pyridazinyl group (pyridazinyl), isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, purinyl Thalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthridinyl group, Acridinyl, phenanthrolinyl, phenazinyl, benzooxazolyl, benzoimidazolyl, furanyl, benzofuranyl, thiophenyl group nyl), benzothiophenyl, thiazolyl, isothiazolyl, benzothiazolyl, isoxazolyl, oxazolyl, triazole Diyl, tetrazolyl group, oxadiazolylene, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imida Zopyridimidinyl group, imidazopyridinyl group, benzofuropyridinyl group (benzofuropyridinyl), benzothiophenopyridinyl group (benzothiophenopyridinyl), benzofuropyrimidinyl group (benzofuropyrimidinyl), benzothiophenopyrimidinyl group ( benzothiophenopyimidinyl),

group represented by

a group represented by , and

group represented by ;

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 및Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pi Renyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, A quinoxalinyl group, a carbazolyl group, a phenyl group-substituted carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, substituted with at least one of a phenyl group-substituted benzocarbazolyl group, a phenyl group-substituted dibenzocarbazolyl group, an imidazopyrimidinyl group, an imidazopyridinyl group, and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) , phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group group, fluoranthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pyrrolyl group, imidazolyl group, pyrazolyl 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, benzooxazolyl group, benzimidazolyl group, furanyl group, Benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, imidazopyridinyl group, benzofuropyridinyl group, benzothiophenopyridinyl group, benzofuropyrimidinyl group, benzothiophenopyrimidinyl group,

group represented by

a group represented by , and

group represented by ; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ); is selected from;

The Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ 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 A group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group , phenanthrenyl group, triphenylenyl group, pyrenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, carbazolyl group, phenanthroly It may be selected from a nyl group, a benzoimidazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group.

According to one embodiment, in Formulas 51A, 51B and 51C, R ₁ to R ₃ , R ₁₁ to R ₁₄ and R ₂₁ to R ₂₃ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of salts thereof;

Formulas 54-1 to 54-49 below; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ); can be selected from:

In Formulas 54-1 to 54-49,

Y ₃₁ is O, S, C(Z ₃₃ )(Z ₃₄ ), N(Z ₃₅ ) or Si(Z ₃₆ )(Z ₃₇ );

Z ₃₁ to Z ₃₇ 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 an acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, Phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group , carbazolyl group, phenyl group-substituted carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenyl group-substituted a benzocarbazolyl group, a phenyl group-substituted dibenzocarbazolyl group, an imidazopyrimidinyl group, an imidazopyridinyl group, and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ );

The Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ 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 A group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group , phenanthrenyl group, triphenylenyl group, pyrenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, carbazolyl group, phenanthroly a nyl group, a benzoimidazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group;

e1 is selected from an integer from 1 to 5, e2 is selected from an integer from 1 to 7, e3 is selected from an integer from 1 to 3, e4 is selected from an integer from 1 to 4, e5 is 1 or 2; , e6 is selected from an integer of 1 to 6, and * is a binding site with a neighboring atom.

According to another embodiment, in Formulas 51A, 51B and 51C, R ₁ to R ₃ , R ₁₁ to R ₁₄ and R ₂₁ to R ₂₃ are each independently selected from the group consisting of:

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of salts thereof; and

Formulas 55-1 to 55-77 below; may be selected from, but not limited to:

According to one embodiment, in Formulas 51A, 51B, and 51C, R ₁ , R ₂ , R ₁₁ to R ₁₄ , R ₂₂ and R ₂₃ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ Alkoxy group, phenyl group, naphthyl group, anthracenyl group, triphenylenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazole It may be selected from a diyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group and a quinoxalinyl group.

For example, in Formulas 51A, 51B, and 51C, R ₁ , R ₂ , R ₁₁ to R ₁₄ , R ₂₂ and R ₂₃ are each independently selected from hydrogen, a C ₁ -C ₂₀ alkyl group, a phenyl group, and a naphthyl group may be, but is not limited thereto.

According to another embodiment, in Formulas 51A, 51B, and 51C, R ₃ and R ₂₁ may be each independently selected from a substituted or unsubstituted C ₆ -C ₃₀ aryl group, or a substituted or unsubstituted C ₁ -C ₃₀ hetero It may be selected from an aryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

In Formulas 51A, 51B and 51C, R ₃ and R ₂₁ are each independently

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 및Phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyrida A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, substituted with at least one of a zinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinolinyl group, and a quinazolinyl group; Azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthrenyl group, triphenylenyl group, pi Renyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyri Dazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cy Nolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzooxazolyl group, benzoimidazolyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazole Diary, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarba Zolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, imidazopyridinyl group, benzofuropyridinyl group, benzothiophenopyridinyl group, benzofuropyrimidinyl group, benzothiophenopyrimidinyl group ,

group represented by

a group represented by , and

group represented by ; and

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 중에서 선택되고,Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pi Renyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, A quinoxalinyl group, a carbazolyl group, a phenyl group-substituted carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, substituted with at least one of a phenyl group-substituted benzocarbazolyl group, a phenyl group-substituted dibenzocarbazolyl group, an imidazopyrimidinyl group, an imidazopyridinyl group, and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) , phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group group, fluoranthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pyrrolyl group, imidazolyl group, pyrazolyl 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, benzooxazolyl group, benzimidazolyl group, furanyl group, Benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, imidazopyridinyl group, benzofuropyridinyl group, benzothiophenopyridinyl group, benzofuropyrimidinyl group, benzothiophenopyrimidinyl group,

group represented by

a group represented by , and

group represented by ; is selected from

The Q ₃₃ to Q ₃₅ 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 car Acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, tri Phenylenyl group, pyrenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group , a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group, but is not limited thereto.

For example, R ₃ and R ₂₁ in Formulas 51A, 51B, and 51C may be each independently selected from one of Formulas 54-1 to 54-49 (eg, one of Formulas 55-1 to 55-77) ), but is not limited thereto.

According to another embodiment, in Formulas 51A, 51B, and 51C, R ₃ is a substituted or unsubstituted C ₁ -C ₃₀ heteroaryl group containing at least one nitrogen as a ring-forming atom, and a substituted or unsubstituted It may be selected from a monovalent non-aromatic condensed heteropolycyclic group.

For example, R ₃ in Formulas 51A, 51B, and 51C may be selected from Formulas 54-7 to 54-25 and 54-32 to 54-49, but is not limited thereto.

As another example, R ₃ in Formulas 51A, 51B, and 51C may be selected from Formulas 55-27 to 55-77, but is not limited thereto.

In Formulas 51A and 51B, b1 represents the number of R ₁ , and may be selected from an integer of 1 to 5. For example, b1 may be 1 or 2. When b1 is 2 or more, two or more R ₁ may be the same as or different from each other. For the description of b2, b3, b11 to b14, and b21, refer to the description of b1. For example, b1 to b3, b11 to b41, and b21 may be 1 or 2, but are not limited thereto.

In Formulas 51A and 51B, c1 represents the number of -[(L ₁ ) _a1 -(R ₁ ) _b1 ] and may be selected from an integer of 1 to 4. For example, c1 is 1 or 2. When c1 is 2 or more, two or more -[(L ₁ ) _a1 -(R ₁ ) _b1 ] may be the same as or different from each other. For example, c1 and c2 may be 1 or 2, but is not limited thereto.

According to one embodiment, the compound represented by one of Formulas 51A and 51B may be represented by one of Formulas 51A-1 to 51A-16 and 51B-1 to 51B-3:

<Formula 51A-1> <Formula 51A-2>

<Formula 51A-3> <Formula 51A-4>

<Formula 51A-5> <Formula 51A-6>

<Formula 51A-7> <Formula 51A-8>

<Formula 51A-9> <Formula 51A-10>

<Formula 51A-11> <Formula 51A-12>

<Formula 51A-13> <Formula 51A-14>

<Formula 51A-15> <Formula 51A-16>

<Formula 51B-1> <Formula 51B-2>

<Formula 51B-3>

Rings A ₁ , L ₁ to L ₃ , a1 to a3, R in Formulas 51A-1 to 51A-16 and 51B-1 to 51B-3 (a1 and a2 are 0 and b1 and b2 are 1) For descriptions of ₁ to R ₃ , R ₁₁ to R ₁₄ , b1 to b3 , c1 and c2, refer to the descriptions of Formulas 51A, 51B and 51C.

As another example, the compound represented by one of Formulas 51A and 51B may be represented by one of Formulas 51A(1)-1 to 51A(1)-16, but is not limited thereto:

<Formula 51A(1)-1> <Formula 51A(1)-2>

<Formula 51A(1)-3> <Formula 51A(1)-4>

<Formula 51A(1)-5> <Formula 51A(1)-6>

<Formula 51A(1)-7> <Formula 51A(1)-8>

<Formula 51A(1)-9> <Formula 51A(1)-10>

<Formula 51A(1)-11> <Formula 51A(1)-12>

<Formula 51A(1)-13> <Formula 51A(1)-14>

<Formula 51A(1)-15> <Formula 51A(1)-16>

X ₂₁ , L ₁ to L ₃ , a1 to a3 , R ₁ to R in Formulas 51A(1)-1 to 51A(1)-16 (a1 and a2 are 0 and b1 and b2 are 1) For the description of ₃ , R ₁₁ to R ₁₄ , b1 to b3 , c1 and c2, refer to the description of Formulas 51A, 51B and 51C.

The compound represented by Formulas 51A and 51B may be one of the following compounds (51)-1 to (51)-200, but is not limited thereto:

In the compound represented by Formula 51A or 51B, at least one of X ₁₁ to X ₁₄ is necessarily N. Accordingly, the HOMO and LUMO energy levels of the compound represented by Formulas 51A or 51B can be easily controlled depending on the device structure, and the condensed ring according to the number and position of N in X ₁₁ to X ₁₄ in Formulas 51A and 51B The S ₁ energy level and the T ₁ energy level of the compound can be easily adjusted. The condensed cyclic compound may be variously applied as, for example, red, green, and blue dopants.

For example, compounds (51)-1, (51)-25, (51)-26, (51)-37, (51)-39, (51)-101 to (51)-104, (51) -113, (51)-114, (51)-132, (51)-133, (51)-134, (51)-146, (51)-148, (51)-156 to (51)-158 , (51)-170, (51)-171 and (51)-172 HOMO, LUMO, singlet (S1) energy level and triplet (T1) energy level using the DFT method of the Gaussian program (B3LYP, The results of evaluation using the method of structural optimization at the 6-31G(d,p) level are shown in Table 4 below:

From Table 4 above, compounds (51)-1, (51)-25, (51)-26, (51)-37, (51)-39, (51)-101 to (51)-104, (51) -113, (51)-114, (51)-132, (51)-133, (51)-134, (51)-146, (51)-148, (51)-156 to (51)-158 , (51)-170, (51)-171 and (51)-172, it can be confirmed that they have electrical properties suitable for use as a material for an organic light emitting device.

A method for synthesizing the condensed cyclic compound represented by Formula 51A or 51B can be easily recognized by those skilled in the art with reference to the following synthesis examples.

Formula 61

<Formula 61>

Ring A ₁ in Formula 61 is represented by Formula 61A.

<Formula 61A>

In Formula 61A, X ₁ is N-[(L ₁ ) _a1- (R ₁ ) _b1 ], S, O, S(=O), S(=O) ₂ , C(=O), Si(R ₄ ) )(R ₅ ), P(R ₄ ), P(=O)(R ₄ ) or C=N(R ₄ ). Here, the description of L ₁ , a1 , R ₁ , b1 , R ₄ , and R ₅ will be described later with reference to the bar.

According to an embodiment, in Formula 61A, X ₁ may be N-[(L ₁ ) _a1- (R ₁ ) _b1 ], S, O, or Si(R ₄ )(R ₅ ).

According to another embodiment, in Formula 61A, X ₁ may be S, O, or Si(R ₄ )(R ₅ ), but is not limited thereto.

According to another embodiment, X ₁ in Formula 61A may be S or O, but is not limited thereto.

Ring A ₁ in Formula 61 is fused to two adjacent 6-membered cyclic rings while sharing a carbon atom. Accordingly, Chemical Formula 61 may be represented by one of Chemical Formulas 61-1 and 61-2 below:

<Formula 61-1>

<Formula 61-2>

In Formulas 61-1 to 61-2, X ₁ , L ₁ to L ₃ , a1 to a3 , R ₁ to R ₅ , R ₁₁ to R ₁₄ , b1 to b3 and b11 to b14 are the same as for Formula 61. See description.

In Formulas 61 and 61A, L ₁ to L ₃ are each independently selected from a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or unsubstituted selected from a C ₆ -C ₆₀ arylene group and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed polycyclic group), L ₂ and L ₃ are substituted or unsubstituted carba It is not a zolylene group.

For example, in Formulas 61 and 61A, L ₁ to L ₃ are each independently

phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acetonitrile Naphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group (fluoranthrenylene), triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenyl pentaphenylene, hexacenylene, pyrrolylene, imidazolylene, pyrazolylene, pyridinylene, pyrazinylene, pyrimidi Nylene group (pyrimidinylene), pyridazinylene group (pyridazinylene), isoindolylene group (isoindolylene), indolylene group (indolylene), indazolylene group (indazolylene), purinylene group (purinylene), quinolinylene group (quinolinylene) , isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene , cinnolinylene, phenanthridinylene, acridinylen e), a phenanthrolinylene group, a phenazinylene group, a benzooxazolylene group, a benzoimidazolylene group, a furanylene group (furanylene), a benzofuranylene group, Thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group, oxazolylene group ( oxazolylene), triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzothiophenylene group (dibenzothiophenylene), benzocarbazolylene group, di a benzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene 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, C ₆ -C ₂₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, and inda, which is substituted with at least one of a heterocondensed ring group, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) Cenylene group, acenaphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group, triphenylenylene group, pyrenylene group, cry Cenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pyrrolylene group, imidazolylene group, pyrazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, Pyridazinylene group, isoindolylene group, indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinox Salinylene group, quinazolinylene group, cinolinylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoxazolylene group, benzoimidazolylene group, furanylene group, benzofura Nylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group, oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinyl Rene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, imidazopyrimidinylene group, and imidazopyridinylene group;

Q ₃₃ to Q ₃₅ are each independently, hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazole Diary, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group phthalazinyl group, quinoxalinyl group , a cinolinyl group and a quinazolinyl group, but L ₂ and L ₃ are not a substituted or unsubstituted carbazolylene group.

According to one embodiment, L ₁ to L ₃ in Formulas 61 and 61A may be each independently represented by one of Formulas 42-1 to 42-13:

According to another embodiment, L ₁ to L ₃ in Formulas 61 and 61A may be each independently represented by one of Formulas 43-1 to 43-12, but are not limited thereto:

In Formula 61, a1 represents the number of L ₁ s, and may be 0, 1, 2, 3, 4, or 5, for example, 0, 1, or 2, and as another example, may be 0 or 1. When a1 is 0, *-(L ₁ ) _a1 -*' becomes a single bond. When a1 is 2 or more, two or more L ₁ may be the same as or different from each other. Descriptions of a2 and a3 may be understood with reference to the description of a1 and the structure of Formula 61.

According to one embodiment, in Formulas 61 and 61A, a1, a2, and a3 may each independently be 0, 1, or 2.

In Formulas 61 and 61A, R ₁ to R ₅ are each independently selected from hydrogen, deuterium, -F (fluoro group), -Cl (chloro group), -Br (bromo group), -I (iodo group), and hydrogen A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, Substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, 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 cyclo Alkyl 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, A substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ ) (Q ₅ ) and -B(Q ₆ )(Q ₇ ). Here, at least one of R ₂ and R ₃ in Formula 61 is a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, or a substituted or unsubstituted monovalent It is selected from a non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formulas 61 and 61A, R ₁ to R ₅ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of salts thereof;

A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group ), fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group (phenalenyl), phenanthrenyl group (phenanthrenyl), anthracenyl group, fluoran Tenyl group (fluoranthenyl), triphenylenyl group (triphenylenyl), pyrenyl group (pyrenyl), chrysenyl group (chrysenyl), naphthacenyl group (naphthacenyl), picenyl group (picenyl), perylenyl group (perylenyl), penta Phenyl group (pentaphenyl), hexacenyl group (hexacenyl), pentacenyl group (pentacenyl), rubicenyl group (rubicenyl), coronenyl group (coronenyl), ovalenyl group (ovalenyl), pyrrolyl group (pyrrolyl), thiophenyl group ), furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl , pyridinyl group, pyrazinyl group (pyrazinyl), pyrimidinyl group (pyrimidinyl), pyridazinyl group (pyridazinyl), isoindolyl group (isoindolyl), indolyl group (indolyl), indazolyl group (indazolyl), Purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl , quinazolinyl group, cinnolinyl group, carbazolyl group ( carbazolyl), phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl (benzothiophenyl), isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl ), triazinyl group, dibenzofuranyl group (dibenzofuranyl), dibenzothiophenyl group (dibenzothiophenyl), benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, hep Thalenyl 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, 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, iso Indolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazole Diary, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, tria Zolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and bi A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group substituted with at least one of the phenyl groups , dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, penta Phenyl group, hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thi Ophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindole Diary, 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, isobenzoxazolyl group, triazole diyl, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl group; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ), provided that R ₄ and R ₅ are not -Si(Q ₃ )(Q ₄ )(Q ₅ ); is selected from

wherein Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group , fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, It is selected from an isoquinolinyl group, a quinazolinyl group and a quinoxalinyl group,

wherein i) at least one of R ₂ and R ₃ and ii) R ₁ are, independently of each other,

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, penta Cenyl 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, pyri Dinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthi Ridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, iso Benzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzo a carbazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, hep Thalenyl 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, 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, iso Indolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazole Diary, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, tria Zolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and bi A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group substituted with at least one of the phenyl groups , dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, penta Phenyl group, hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thi Ophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindole Diary, 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, triazole diary, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl group; can be selected from

According to one embodiment, in Formulas 61 and 61A, R ₁ to R ₅ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of salts thereof;

Phenyl group, naphthyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group , pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and dibenzocarbazole group diary;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), phenyl group, naphthyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, Fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxali group phenyl group, naphthyl group, phenalenyl group, phenyl group substituted with at least one of a nyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group Trenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and dibenzocarbazolyl group; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ), provided that R ₄ and R ₅ are not -Si(Q ₃ )(Q ₄ )(Q ₅ ); is selected from

wherein Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group , fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, It is selected from an isoquinolinyl group, a quinazolinyl group and a quinoxalinyl group,

wherein i) at least one of R ₂ and R ₃ and ii) R ₁ are, independently of each other,

Phenyl group, naphthyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group , pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and dibenzocarbazole group diary; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), phenyl group, naphthyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, Fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxali group phenyl group, naphthyl group, phenalenyl group, phenyl group substituted with at least one of a nyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group Trenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and dibenzocarbazolyl group; can be selected from

According to another embodiment, in Formulas 61 and 61A, R ₁ to R ₅ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of salts thereof;

Formulas 44-1 to 44-31; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ); (However, the R ₄ to R ₅ are -Si(Q ₃ )(Q ₄ )(Q ₅ ) is not selected from),

At least one of i) R ₂ and R ₃ and ii) R ₁ may be each independently represented by one of Formulas 44-1 to 44-31:

According to another embodiment, in Formulas 61 and 61A, R ₁ is,

a phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group and a perylenyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, cry A phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, and a peryle group substituted with at least one selected from a cenyl group and a perylenyl group nyl group; can be selected from

According to another embodiment, at least one of R ₂ and R ₃ of Formula 61 is,

a triphenylenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group and a benzocarbazolyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), phenyl group, naphthyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, Fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxali group substituted with at least one of a nyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group, a triphenylenyl group, a carbazolyl group, a di a benzofuranyl group, a dibenzothiophenyl group and a benzocarbazolyl group; can be selected from

According to another embodiment, at least one of R ₂ and R ₃ of Formula 61 is,

a triphenylenyl group and a carbazolyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), phenyl group, naphthyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, Fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxali group a triphenylenyl group and a carbazolyl group substituted with at least one of a nyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group; may be selected from, but is not limited thereto.

In Formula 61, R ₁₁ to R ₁₄ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydra Group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, Condensed monovalent non-aromatic heteropolycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ) and -B(Q ₆ )(Q ₇ ) may be selected from have.

For example, R ₁₁ to R ₁₄ in Formula 61 are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of salts thereof;

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, penta Cenyl 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, pyri Dinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthi Ridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, iso Benzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzo a carbazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ); is selected from;

Wherein Q ₃ To Q ₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, cry Cenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quina It may be selected from a jolinyl group and a quinoxalinyl group.

According to one embodiment, R ₁₁ to R ₁₄ in Formula 61 are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

Phenyl group, naphthyl 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, perylenyl group, thiophenyl group, furanyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group , benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and dibenzocarbazolyl group; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ); is selected from;

Wherein Q ₃ To Q ₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, cry Cenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quina It may be selected from a jolinyl group and a quinoxalinyl group.

According to another embodiment, in Formula 61, R ₁₁ to R ₁₄ may each independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, or an amino group. It may be selected from a dino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group, and a C ₁ -C ₂₀ alkoxy group, but is limited thereto not.

According to another embodiment, all of R ₁₁ to R ₁₄ in Formula 61 may be hydrogen.

According to another embodiment, in Formulas 61 and 61A, R ₁ to R ₅ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of salts thereof;

one of the following formulas 65-1 to 65-85; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ); (provided that R ₄ and R ₅ are -Si(Q ₃ )(Q ₄ )(Q ₅ ) is not selected from),

i) at least one of R ₂ and R ₃ and ii) R ₁ are each independently represented by one of the following formulas 65-1 to 65-85,

The R ₁₁ to R ₁₄ are each independently,

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

Formulas 65-1 to 65-4, 65-10 to 65-17, 65-26 to 65-31, 65-39, 65-40, 65-42, 65-44, 65-47 and 65-48; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ); is selected from

Wherein Q ₃ To Q ₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, cry Cenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quina It may be selected from a jolinyl group and a quinoxalinyl group, but is not limited thereto:

In Formula 611, R ₃ is not a substituted or unsubstituted morpholinyl group.

When R ₃ in Formula 61 is a pyridinyl group, a pyridazinyl group or a pyrimidinyl group, R ₂ is hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, or a nitro group , amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ - C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted di It may be selected from a benzothiophenyl group.

In Formula 61, when R ₂ is a substituted or unsubstituted phenyl group, R ₃ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted triphenyl Renyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted carbazolyl group, substituted or Unsubstituted benzocarbazolyl group, substituted or unsubstituted dibenzocarbazolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted pyridinyl group, substituted or Unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quina It may be selected from a jolinyl group and a substituted or unsubstituted quinoxalinyl group.

In Formulas 61 and 61A, b1 represents the number of R ₁ , and may be selected from an integer of 1 to 3. For example, b1 may be 1 or 2. As another example, b1 may be 1. When b1 is 2 or more, two or more R ₁ may be the same as or different from each other. The description of b2 and b3 may be understood with reference to the description of b1 and the structure of Formula 61.

According to one embodiment, the compound represented by Formula 61 is represented by Formula 61-1, wherein in Formula 61-1,

X ₁ is S or O,

L ₂ and L ₃ are independently of each other,

Phenylene group, naphthylene group, phenanthrenylene group, anthracenylene group, triphenylenylene group, carbazolylene group, pyridinylene group, pyrimidinylene group, triazinylene group, quinazolinylene group, quinolinylene group, isoquinylene group a nolinylene group, a naphthyridinylene group, and an oxadiazolylene 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, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, and a phenylene group substituted with at least one of a phenanthrenyl group , naphthylene group, phenanthrenylene group, anthracenylene group, triphenylenylene group, carbazolylene group, pyridinylene group, pyrimidinylene group, triazinylene group, quinazolinylene group, quinolinylene group, isoquinolinyl group a ren group, a naphthyridinylene group, and an oxadiazolylene group; is selected from

a2 and a3 are 0 or 1,

R ₂ and R ₃ are independently of each other,

Phenyl group, naphthyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group , pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and dibenzocarbazole group diary; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, cry Cenyl group, perylenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, triazinyl group, di A phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, triphenylle, substituted with at least one of a benzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group Nyl group, pyrenyl group, chrysenyl group, perylenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazole a diyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group; is selected from

b2 and b3 may be 1, but is not limited thereto.

The compound represented by Formula 61 may be one of the following compounds (61)-1 to (61)-424, but is not limited thereto:

At least one of R ₂ and R ₃ in Formula 61 is a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non- It is necessarily selected from a condensed aromatic polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group. Accordingly, the compound represented by Formula 61 is suitable as a material for an organic light emitting device, for example, a host material in the light emitting layer (for example, a host material in the light emitting layer including a host and a dopant) HOMO, LUMO T1 energy level and S1 It can have energy levels. In addition, since the compound represented by Formula 61 has excellent thermal stability and electrical stability, an organic light emitting device employing the compound represented by Formula 61 may have high efficiency and long lifespan characteristics.

<Formula 61'>

On the other hand, the compound represented by Formula 61 has a core (see Formula 61' below) in which a pyrimidine ring and a benzene ring are condensed on both sides of Ring A ₁ . Therefore, it can have a HOMO energy level, a LUMO energy level, a T1 energy level and an S1 energy level suitable for use as an organic layer material (eg, a light emitting layer material) between a pair of electrodes of an organic light emitting device, and has excellent thermal stability. and electrical stability. For example, when the compound represented by Formula 61 is used as a host in the light emitting layer of the organic light emitting device, high efficiency and long lifespan light emission is possible through the principle of an energy transfer mechanism between the host and the dopant.

Although not intended to be limited by a specific principle, the following compound (61)-B has an excessively strong electron transport ability, making it difficult to achieve a balance between hole transport and electron transport. Accordingly, the efficiency characteristics of the organic light emitting device employing the compound (61)-B may deteriorate. In addition, since the following compound (61)-C has a pyrazine ring instead of a pyrimidine ring having a condensed ring core, thermal stability and electrical stability may be poor.

<Compound (61)-B>

<Compound (61)-C>

<Compound (61)-D>

The above-mentioned compounds (61)-5, (61)-16, (61)-9, (61)-30, (61)-29, (61)-37, (61)-40, (61) )-21, (61)-27, (61)-12, (61)-13, (61)-18, (61)-11, (61)-45 and (61)-48 and the above compound (61) The HOMO, LUMO, and triplet (T1) energy levels of )-B, (61)-C and (61)-D can be confirmed from Table 5, which is the result of evaluation using a Gaussian simulation method.

From Table 5, the absolute LUMO values of the compounds (61)-B are the compounds (61)-5, (61)-16, (61)-9, (61)-30, (61)-29, (61) )-37, (61)-40, (61)-21, (61)-27, (61)-12, (61)-13, (61)-18, (61)-11, (61)- 45 and (61)-48 were higher than the absolute LUMO values, indicating that the electron transport properties were too strong, and the absolute LUMO values of compounds (61)-C and (61)-D were the compounds (61)-5, ( 61)-16, (61)-9, (61)-30, (61)-29, (61)-37, (61)-40, (61)-21, (61)-27, (61) It can be seen that the electron transport properties are too weak because the LUMO values of -12, (61)-13, (61)-18, (61)-11, (61)-45 and (61)-48 are lower than the absolute values. Accordingly, the compounds (61)-B, (61)-C and (61)-D are the compounds (61)-5, (61)-16, (61)-9, (61)-30, (61) )-29, (61)-37, (61)-40, (61)-21, (61)-27, (61)-12, (61)-13, (61)-18, (61)- 11, (61)-45 and (61)-48, it can be seen that it may be difficult to achieve a balance between hole transport and electron transport.

A method for synthesizing the condensed cyclic compound represented by Chemical Formula 61 can be easily recognized by those skilled in the art with reference to Synthesis Examples to be described later.

Formulas 71-1 to 71-12

<Formula 71-1>

<Formula 71-2>

<Formula 71-3>

<Formula 71-4>

<Formula 71-5>

<Formula 71-6>

<Formula 71-7>

<Formula 71-8>

<Formula 71-9>

<Formula 71-10>

<Formula 71-11>

<Formula 71-12>

In Formulas 71-1 to 71-12, X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], S, O, S(=O), S(=O) ₂ , C(= O), C(R ₁₂ )(R ₁₃ ), Si(R ₁₂ )(R ₁₃ ), P(R ₁₂ ), or P(=O)(R ₁₂ ); X ₂₁ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ], S, O, S(=O), S(=O) ₂ , C(=O), C(R ₂₂ )(R ₂₃ ), Si(R ₂₂ )(R ₂₃ ), P(R ₂₂ ) or P(=O)(R ₂₂ ).

According to one embodiment, in Formulas 71-1 to 71-12, X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], S, O, C(R ₁₂ )(R ₁₃ ) or Si(R ₁₂ )(R ₁₃ ); X ₂₁ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ], S, O, C(R ₂₂ )(R ₂₃ ) or Si(R ₂₂ )(R ₂₃ ), but is not limited thereto.

In Formulas 71-1 to 71-12, X ₃₁ to X ₃₄ may each independently represent N or C-[(L ₂ ) _a2 -(R ₂ ) _b2 ].

When two or more of X ₃₁ to X ₃₄ in Formulas 71-1 to 71-12 are C-[(L ₂ ) _a2 -(R ₂ ) _b2 ], they may be different from or the same as each other.

According to one embodiment, all of X ₃₁ to X ₃₄ in Formulas 71-1 to 71-12 may be C-[(L ₂ ) _a2 -(R ₂ ) _b2 ].

Accordingly, the compound represented by one of Chemical Formulas 71-1 to 71-12 may be represented by one of the following Chemical Formulas 71A-1 to 71A-12:

<Formula 71A-1>

<Formula 71A-2>

<Formula 71A-3>

<Formula 71A-4>

<Formula 71A-5>

<Formula 71A-6>

<Formula 71A-7>

<Formula 71A-8>

<Formula 71A-9>

<Formula 71A-10>

<Formula 71A-11>

<Formula 71A-12>

For the description of X ₁₁ , X ₂₁ , L ₁ to L ₃ , a1 to a3 , R ₁ to R ₇ and c1 in Formulas 71A-1 to 71A-12, see the description of Formulas 71-1 to 71-12. and c2 is selected from an integer of 1 to 4.

With respect to the compounds represented by the formulas 71-1 to 71-12,

i) In Formula 71-2, when X ₁₁ is C(R ₁₂ )(R ₁₃ ), X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ],

ii) In Formula 71-2, when X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], X ₂₁ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ] and C( R ₂₂ ) not (R ₂₃ ),

iii) In Formula 71-4, when X ₁₁ is C(R ₁₂ )(R ₁₃ ), X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ],

iv) In Formula 71-8, when X ₁₁ is C(R ₁₂ )(R ₁₃ ), X ₂₁ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ] and C(R ₂₂ )(R ₂₃ ) ), not

v) In Formula 71-8, when X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], X ₂₁ is not C(R ₂₂ )(R ₂₃ ),

vi) In Formula 71-8, when X ₁₁ is S, X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ],

vii) in Formula 71-8, when X ₁₁ is Si(R ₁₂ )(R ₁₃ ), X ₂₁ is not N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ],

viii) In Formula 71-11, when X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], X ₂₁ is not C(R ₂₂ )(R ₂₃ ).

Accordingly, when the compound represented by one of 71-1 to 71-12 is represented by Formula 71-2, it is represented by one of Formulas 71A-2-1 to 71A-2-22, and 71-1 to 71 When the compound represented by one of -12 is represented by Formula 71-4, the compound represented by one of the following Formulas 71A-4-1 to 71A-4-24, and the compound represented by one of 71-1 to 71-12 When represented by Formula 71-8, the compound represented by one of the following Formulas 71A-8-1 to 71A-8-20, and the compound represented by one of the following Formulas 71A-8-1 to 71A-12, may be represented by Formula 71A-11 case, it may be represented by one of the following Chemical Formulas 71A-11-1 to 71A-11-24, but is not limited thereto:

For example, Chemical Formula 71A-2-10 has a backbone of Chemical Formula 71A-2, wherein X ₁₁ is O, X ₁₂ is O, and Chemical Formula 71A-2-14 is a compound of Chemical Formula 71A-2 has a backbone, wherein X ₁₁ is S and X ₁₂ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ]:

<Formula 71A-2-10>

<Formula 71A-2-14>

Formulas 71A-2-1 to 71A-2-22, 71A-4-1 to 71A-4-24, 71A-8-1 to 71A-8-20, and 71A-11-1 to 71A-11-24 The structure can be understood with reference to the above.

According to one embodiment, the compounds represented by the formulas 71-1 to 71-12,

Represented by one of Formulas 71-1 to 71-7 and 71-9 to 71-12,

In Formulas 71-1 to 71-7 and 71-9 to 71-12

X ₁₁ and X ₁₂ are each independently O or S;

X ₁₁ is O or S and X ₁₂ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ] or C(R ₂₂ )(R ₂₃ );

X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ] or C(R ₁₂ )(R ₁₃ ), and X ₁₂ is O or S; or

X ₁₁ may be C(R ₁₂ )(R ₁₃ ), and X ₁₂ may be C(R ₂₂ )(R ₂₃ ).

According to another embodiment, the compound represented by Formulas 71-1 to 71-12 is,

represented by one of Formulas 71A-1 to 71A-7 and 71A-9 to 71A-12,

In Formulas 71A-1 to 71A-7 and 71A-9 to 71A-12,

X ₁₁ and X ₁₂ are each independently O or S;

X ₁₁ is O or S and X ₁₂ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ] or C(R ₂₂ )(R ₂₃ );

X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ] or C(R ₁₂ )(R ₁₃ ), and X ₁₂ is O or S; or

X ₁₁ may be C(R ₁₂ )(R ₁₃ ), and X ₁₂ may be C(R ₂₂ )(R ₂₃ ).

According to another embodiment, the compound represented by Formulas 71-1 to 71-12 is represented by one of Formulas 71-1, 71-3 to 71-7, and 71-9 to 71-11, and In 71-1, 71-3 to 71-7, and 71-9 to 71-11, X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], and X ₁₂ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ].

According to another embodiment, the compound represented by Formulas 71-1 to 71-12 is represented by one of Formulas 71A-1, 71A-3 to 71A-7, and 71A-9 to 71A-11, and In 71A-1, 71A-3 to 71A-7, and 71A-9 to 71A-11, X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], and X ₁₂ is N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ].

According to another embodiment, the compounds represented by Formulas 71-1 to 71-12 are represented by Formula 71-2, wherein in Formula 71-2, X ₁₁ is O or S, X ₁₂ is O, S or N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ].

According to another embodiment, the compound represented by Formulas 71-1 to 71-12 is represented by Formula 71A-2, wherein in Formula 71A-2, X ₁₁ is O or S, X ₁₂ is O, S or N-[(L ₂₁ ) _a21 -(R ₂₁ ) _b21 ].

According to one embodiment, the compound represented by Formulas 71-1 to 71-12 is represented by one of Formulas 71-1 to 71-7 and 71-9 to 71-12, wherein the compounds represented by Formulas 71-1 to 71-12 In -7 and 71-9 to 71-12, X ₁₁ may be O or S. The condensed cyclic compound in which X ₁₁ is O or S may have improved planarity, and may have excellent charge mobility due to one pair of electrons of O and S.

In Formulas 71-1 to 71-12, L ₁ to L ₃ , L ₁₁ and L ₁₂ may each independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ Heterocycloalkylene group, 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 an unsubstituted C ₁ -C ₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed polycyclic group), and a substituted or unsubstituted divalent non-aromatic hetero Condensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group) may be selected from.

According to one embodiment, in Formulas 71-1 to 71-12, L ₁ to L ₃ , L ₁₁ and L ₁₂ are each independently

phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acetonitrile Naphthylene group (acenaphthylene), fluorenylene group (fluorenylene), spiro-fluorenylene group, phenalenylene group (phenalenylene), phenanthrenylene group (phenanthrenylene), anthracenylene group (anthracenylene), fluoranxenylene group ( fluoranthenylene), triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenylene (pentaphenylene), hexacenylene, pyrrolylene, imidazolylene, pyrazolylene, pyridinylene, pyrazinylene, pyrimidinyl Ren group (pyrimidinylene), pyridazinylene group (pyridazinylene), isoindolylene group (isoindolylene), indolylene group (indolylene), indazolylene group (indazolylene), purinylene group (purinylene), quinolinylene group (quinolinylene), isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, Cinnolinylene group, carbazolylene group, phenanthridinylene group , acridinylene group, phenanthrolinylene group, phenazinylene group, benzooxazolylene group, benzoimidazolylene group, furanylene group, benzofura Nylene group (benzofuranylene), thiophenylene group (thiophenylene), benzothiophenylene group (benzothiophenylene), thiazolylene group (thiazolylene), isothiazolylene group (isothiazolylene), benzothiazolylene group (benzothiazolylene), isoxazolylene group (isoxazolylene) ), oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene 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, C ₆ -C ₂₀ aryl group, C ₁ -C ₂₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indium substituted with at least one of a condensed heterocyclic group and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) Cenylene group, acenaphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group, triphenylenylene group, pyrenylene group, cry Cenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pyrrolylene group, imidazolylene group, pyrazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, Pyridazinylene group, isoindolylene group, indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinox Salinylene group, quinazolinylene group, cinolinylene group, carbazolylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoxazolylene group, benzoimidazolylene group, furanyl Ren group, benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group, oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolyl a ren group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene group; is selected from

Q ₃₃ to Q ₃₅ are each independently, hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazole Diary, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group phthalazinyl group, quinoxalinyl group , it may be selected from a cinolinyl group and a quinazolinyl group.

According to another embodiment, in Formulas 71-1 to 71-12, L ₁ to L ₃ , L ₁₁ and L ₁₂ are

a phenylene group, a naphthylene group, and a triphenylene 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, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, and a chrysenyl group substituted with at least one, a phenylene group, a naphthylene group, and a triphenylene group;

may be selected from, but is not limited thereto.

According to another embodiment, L ₁ to L ₃ , L ₁₁ and L ₁₂ in Formulas 71-1 to 71-12 may be each independently selected from Formulas 12-1 to 12-37.

According to another embodiment, L ₁ to L ₃ , L ₁₁ and L ₁₂ in Formulas 71-1 to 71-12 may be each independently selected from Formulas 13-1 to 13-21, but are limited thereto. It is not:

According to another embodiment, in Formulas 71-1 to 71-12, L ₁ to L ₃ , L ₁₁ and L ₁₂ are each independently

a phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, and a triazinylene 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 ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group and triazinyl group substituted with at least one of, phenylene group, naphthylene group, pyridinyl group a ren group, a pyrimidinylene group and a triazinylene group; may be selected from, but is not limited thereto.

In Formula 71-1, a1 represents the number of L ₁ , and may be 0, 1, 2, 3, 4, or 5, for example, 0, 1, or 2, and as another example, may be 0 or 1. When a1 is 0, *-(L ₁ ) _a1 -*' becomes a single bond. When a1 is 2 or more, two or more L ₁ may be the same as or different from each other. Descriptions of a2, a3, a11, and a12 may be understood with reference to the description of a1 and Formulas 71-1 to 71-12.

In Formulas 71-1 to 71-12, R ₁ to R ₇ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy Sil group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted Or an unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group , 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 an unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )( Q ₅ ) and -B(Q ₆ )(Q ₇ ) may be selected.

According to an embodiment, in Formulas 71-1 to 71-12, R ₁ to R ₇ , R ₁₁ to R ₁₃ , and R ₂₁ to R ₂₃ may each independently represent hydrogen, deuterium, -F, -Cl, -Br , -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C ₁ -C ₂₀ heteroaryl group, substituted or unsubstituted It may be selected from a monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed hetero condensed polycyclic group, and -Si(Q ₃ )(Q ₄ )(Q ₅ ).

According to another embodiment, when i) X ₁₁ in Formulas 71-1 to 71-12 is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ], at least one of R ₃ and R ₁₁ , ii ) when X ₁₂ is N-[(L ₂₁ ) _a11 -(R ₂₁ ) _b11 ], then at least one of R ₃ and R ₂₁ and iii) X ₁₁ is N-[(L ₁₁ ) _a11 -(R ₁₁ ) _b11 ] and X ₁₂ is N-[(L ₂₁ ) _a11 -(R ₂₁ ) _b11 ], at least one of R ₃ , R ₁₁ and R ₂₁ is, independently of each other, substituted or unsubstituted C ₆ -C ₂₀ It may be selected from an aryl group, a substituted or unsubstituted C ₁ -C ₂₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group. .

According to another embodiment, in Formulas 71-1 to 71-12, R ₃ is a substituted or unsubstituted C ₁ -C ₃₀ heteroaryl group including at least one nitrogen atom as a ring constituent atom, and a substituted or unsubstituted It may be selected from a cyclic monovalent non-aromatic condensed heteropolycyclic group, but is not limited thereto.

According to another embodiment, in Formulas 71-1 to 71-12, R ₁ to R ₇ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of salts thereof;

A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group ), fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group (phenalenyl), phenanthrenyl group (phenanthrenyl), anthracenyl group, fluoran Cenyl group (fluoranthenyl), triphenylenyl group (triphenylenyl), pyrenyl group (pyrenyl), chrysenyl group (chrysenyl), naphthacenyl group (naphthacenyl), picenyl group (picenyl), perylenyl group (perylenyl), penta Phenyl group (pentaphenyl), hexacenyl group (hexacenyl), pentacenyl group (pentacenyl), rubicenyl group (rubicenyl), coronenyl group (coronenyl), ovalenyl group (ovalenyl), pyrrolyl group (pyrrolyl), thiophenyl group ), furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl , pyridinyl group, pyrazinyl group (pyrazinyl), pyrimidinyl group (pyrimidinyl), pyridazinyl group (pyridazinyl), isoindolyl group (isoindolyl), indolyl group (indolyl), indazolyl group (indazolyl), Purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl , quinazolinyl group, cinnolinyl group, carbazolyl group ( carbazolyl), phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl (benzothiophenyl), isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl ), triazinyl group, dibenzofuranyl group (dibenzofuranyl), dibenzothiophenyl group (dibenzothiophenyl), benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, 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, Spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group 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, quinolyl group Nyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl, acridinyl, phenanthrolinyl, phena Zinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, di of a benzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a biphenyl group, and -Si( _Q33 )( _Q34 )( _Q35 ) At least one substituted, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, di benzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, Hexasenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group 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, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, Phenantridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetra a zolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ); is selected from

wherein Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group , fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, It may be selected from an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group, but is not limited thereto.

According to another embodiment, in Formulas 71-1 to 71-12,

R ₁ to R ₇ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, the formulas 44-1 to 44 -31 and -Si(Q ₃ )(Q ₄ )(Q ₅ );

Wherein Q ₃ To Q ₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, cry Cenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quina It may be selected from a jolinyl group and a quinoxalinyl group, but is not limited thereto.

According to another embodiment, in Formulas 71-1 to 71-12,

R ₁ to R ₇ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₃ 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, the formulas 65-1 to 65 -55 and -Si(Q ₃ )(Q ₄ )(Q ₅ );

Wherein Q ₃ To Q ₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, cry Cenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quina It may be selected from a jolinyl group and a quinoxalinyl group, but is not limited thereto.

According to another embodiment, in Formulas 71-1 to 71-12, R ₁ , R ₂ , and R ₄ to R ₇ may be hydrogen, but the present invention is not limited thereto.

In Formulas 71-1 to 71-12, b1 represents the number of R ₁ , and may be selected from an integer of 1 to 5. For example, b1 may be 1 or 2. As another example, b1 may be 1. When b1 is 2 or more, two or more R ₁ may be the same as or different from each other. Descriptions of b2 to b3, b11, and b12 may be understood with reference to the description of b1 and Chemical Formulas 71-1 to 71-12.

In Formulas 71-1 to 71-12, c1 represents the number of -[(L ₁ ) _a1 -(R ₁ ) _b1 ] and may be selected from an integer of 1 to 4. For example, c1 is 1 or 2. When c1 is 2 or more, two or more -[(L ₁ ) _a1 -(R ₁ ) _b1 ] may be the same as or different from each other.

When X ₁₁ in Formulas 71-1 to 71-12 is C(R ₁₂ )(R ₁₃ ) or Si(R ₁₂ )(R ₁₃ ), R ₁₂ and R ₁₃ may be the same as or different from each other. For example, when X ₁₁ is C(R ₁₂ )(R ₁₃ ), various modifications are possible, for example, R ₁₂ may be a methyl group and R ₁₃ may be a phenyl group.

In Formulas 71-1 to 71-12, when X ₂₁ is C(R ₂₂ )(R ₂₃ ) or Si(R ₂₂ )(R ₂₃ ), R ₂₂ and R ₂₃ may be the same or different from each other. For example, when X ₂₁ is C(R ₂₂ )(R ₂₃ ), various modifications are possible, such as R ₂₂ may be a methyl group and R ₂₃ may be a phenyl group.

In Formulas 71-1 to 71-12, L ₃ is selected from a substituted or unsubstituted C ₆ -C ₆₀ arylene group and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and R ₃ is a substituted or unsubstituted It may be selected from a C ₆ -C ₆₀ aryl group and a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group.

For example, in Formulas 71-1 to 71-12, L ₃ is,

a phenylene group, a naphthylene group, and a triphenylene 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, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, and a chrysenyl group substituted with at least one, a phenylene group, a naphthylene group, and a triphenylene group;

is selected from, and R ₃ may be selected from Formulas 44-1 to 44-5.

L ₃ is selected from a substituted or unsubstituted C ₆ -C ₆₀ arylene group and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and R ₃ is a substituted or unsubstituted C ₆ -C ₆₀ aryl group and a substituted Alternatively, the compound represented by one of Formulas 71-1 to 71-12 selected from an unsubstituted monovalent non-aromatic condensed polycyclic group may be included in, for example, a hole transport region of an organic light emitting device to be described later.

According to another embodiment, R ₃ in Formulas 71-1 to 71-12 may be an electron transporting moiety. For example, R ₃ in Formulas 71-1 to 71-12 may be selected from a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group. .

For example, R ₃ in Formulas 71-1 to 71-12 may be represented by one of Formulas 44-6 to 44-25, but is not limited thereto.

The compound represented by one of Formulas 71-1 to 71-12 in which R ₃ is a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group is, for example, , may be included in a light emitting layer of an organic light emitting device to be described later.

The compound represented by Formulas 71-1 to 71-12 may be one of the following compounds (71)-1 to (71)-157, but is not limited thereto:

A method for synthesizing a compound represented by one of Chemical Formulas 71-1 to 71-12 may be readily recognized by those skilled in the art with reference to Synthesis Examples to be described later.

Formula 81

<Formula 81>

In Formula 81, X ₁₁ is S, O, N, C-[(L ₁₁ ) _a11 -(E ₁₁ ) _b11 -(R ₁₁ ) _c11 ] or Si-[(L ₁₁ ) _a11 -(E ₁₁ ) _b11 -(R ₁₁ ) _c11 ], and X ₁₂ is S, O, N, C-[(L ₁₂ ) _a12 -(E ₁₂ ) _b12 -(R ₁₂ ) _c12 ] or Si-[(L ₁₂ ) _a12 -( E ₁₂ ) _b12 -(R ₁₂ ) _c12 ], and X ₁₃ is S, O, N, C-[(L ₁₃ ) _a13 -(E ₁₃ ) _b13 -(R ₁₃ ) _c13 ] or Si-[(L ₁₃ ) ) _a13 -(E ₁₃ ) _b13 -(R ₁₃ ) _c13 ]; X ₂₁ is N or C-[(L ₂₁ ) _a21 -(E ₂₁ ) _b21 -(R ₂₁ ) _c21 ], and X ₂₂ is N or C-[(L ₂₂ ) _a22 -(E ₂₂ ) _b22 -(R ₂₂ ) _c22 ], X ₂₃ is N or C-[(L ₂₃ ) _a23 -(E ₂₃ ) _b23 -(R ₂₃ ) _c23 ], and X ₂₄ is N or C-[(L ₂₄ ) _a24 -(E ₂₄ ) _b24 -(R ₂₄ ) _c24 ], X ₂₅ is N or C-[(L ₂₅ ) _a25 -(E ₂₅ ) _b25 -(R ₂₅ ) _c25 ], and X ₂₆ is N or C-[(L ₂₆ ) _a26 -(E ₂₆ ) _b26 -(R ₂₆ ) _c26 ].

According to one embodiment, in Formula 81, X ₁₁ may be S or O, and X ₁₃ may be N.

According to another embodiment, in Formula 81, X ₁₁ may be S or O, and X ₁₃ may be C-[(L ₁₃ ) _a13 -(E ₁₃ ) _b13 -(R ₁₃ ) _c13 ].

In Formula 81, L ₁ , L ₁₁ to L ₁₃ and L ₂₁ to L ₂₆ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl Rene group, 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 A C ₁ -C ₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed polycyclic group) and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group (substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic group).

According to one embodiment, in Formula 81, L ₁ , L ₁₁ to L ₁₃ and L ₂₁ to L ₂₆ are each independently

phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acetonitrile Naphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group (fluoranthrenylene), triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenyl pentaphenylene, hexacenylene, pyrrolylene, imidazolylene, pyrazolylene, pyridinylene, pyrazinylene, pyrimidi Nylene group (pyrimidinylene), pyridazinylene group (pyridazinylene), isoindolylene group (isoindolylene), indolylene group (indolylene), indazolylene group (indazolylene), purinylene group (purinylene), quinolinylene group (quinolinylene) , isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene , cinnolinylene, carbazolylene, phenanthridinylen e), acridinylene group, phenanthrolinylene group, phenazinylene group, benzooxazolylene group, benzoimidazolylene group, furanylene group, Benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group (isoxazolylene), oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzothiophenylene group ), a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene 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, C ₆ -C ₂₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, and inda, which is substituted with at least one of a heterocondensed ring group, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) Cenylene group, acenaphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group, triphenylenylene group, pyrenylene group, cry Cenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pyrrolylene group, imidazolylene group, pyrazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, Pyridazinylene group, isoindolylene group, indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinox Salinylene group, quinazolinylene group, cinolinylene group, carbazolylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoxazolylene group, benzoimidazolylene group, furanyl Ren group, benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group, oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolyl a ren group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene group; is selected from

Q ₃₃ to Q ₃₅ are each independently, hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazole Diary, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group phthalazinyl group, quinoxalinyl group , but may be selected from a cinolinyl group and a quinazolinyl group, but is not limited thereto.

According to another embodiment, L ₁ , L ₁₁ to L ₁₃ , and L ₂₁ to L ₂₆ in Formula 81 may be each independently selected from Formulas 12-1 to 12-37.

According to another embodiment, L ₁ , L ₁₁ to L ₁₃ and L ₂₁ to L ₂₆ in Formula 81 may be each independently selected from Formulas 13-1 to 13-21, but are not limited thereto. .

In Formulas 13-1 to 13-21, * is a binding site with a core or a binding site with each of neighboring L ₁ , L ₁₁ to L ₁₃ and L ₂₁ to L ₂₆ in Formula 81, and *' is a neighboring L ₁ , a binding site with each of L ₁₁ to L ₁₃ and L ₂₁ to L ₂₆ , a binding site with each of neighboring E ₁ , E ₁₁ to E ₁₃ and E ₂₁ to E ₂₆ or R ₁ , R ₁₁ to R ₁₃ and It is a binding site with each of R ₂₁ to R ₂₆ .

In Formula 81, a1 represents the number of L ₁ s, and may be 0, 1, 2, 3, 4, or 5, for example, 0, 1, or 2, and as another example, may be 0 or 1. When a1 is 0, L ₁ is a single bond. When a1 is 2 or more, two or more L ₁ may be the same as or different from each other. Descriptions of L ₁₁ to L ₁₃ and L ₂₁ to L ₂₆ may be understood with reference to the description of L ₁ and the structure of Formula 81.

According to one embodiment, in Formula 81, a1, a11 to a13, and a21 to a26 may each independently be 0, 1, or 2.

In Formula 81, E ₁ , E ₁₁ to E ₁₃ , and E ₂₁ to E ₂₆ are each independently a substituted or unsubstituted nitrogen-containing electron transporting moiety. The substituted or unsubstituted nitrogen-containing electron transporting moiety may be a cyclic moiety, and nitrogen may be a ring constituent atom of the cyclic moiety. For example, the substituted or unsubstituted nitrogen-containing electron-transporting moiety may include 1, 2, or 3 nitrogen as ring constituent atoms.

For example, in Formula 81, E ₁ , E ₁₁ to E ₁₃ and E ₂₁ to E ₂₆ are each independently a substituted or unsubstituted nitrogen-containing C ₁ -C ₁₀ heterocycloalkylene group, substituted or unsubstituted It is selected from a nitrogen C ₁ -C ₁₀ heterocycloalkenylene group, a substituted or unsubstituted nitrogen-containing C ₁ -C ₆₀ heteroarylene group, and a substituted or unsubstituted nitrogen-containing divalent non-aromatic condensed heteropolycyclic group, wherein A substituted or unsubstituted carbazolylene group is excluded from E ₁ , E ₁₁ to E ₁₃ and E ₂₁ to E ₂₆ .

According to one embodiment, in Formula 81, E ₁ , E ₁₁ to E ₁₃ , and E ₂₁ to E ₂₆ are each independently a substituted or unsubstituted pyrrolylene group, a substituted or unsubstituted imidazolylene group (imidazolylene), a substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted thiazolylene group, a substituted or unsubstituted isothiazolylene group, a substituted or unsubstituted oxazolylene group ( oxazolylene), a substituted or unsubstituted isoxazolylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyrimidinylene group ( pyrimidinylene), a substituted or unsubstituted pyridazinylene group, a substituted or unsubstituted isoindolylene group, a substituted or unsubstituted indolylene group, a substituted or unsubstituted indazolylene group ( indazolylene), a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted isoquinolinylene group, a substituted or unsubstituted benzoquinolinylene group, a substituted or unsubstituted quinol Salinylene group (quinoxalinylene), substituted or unsubstituted quinazolinylene group (quinazolinylene), substituted or unsubstituted phenanthridinylene group (phenanthridinylene), substituted or unsubstituted acridinylene group (acridinylene), substituted or unsubstituted a phenanthrolinylene group, a substituted or unsubstituted phenazinylene group, a substituted or unsubstituted benzoimidazolylene group, a substituted or unsubstituted isobenzothiazolylene group, a substituted Or an unsubstituted benzooxazolylene group (benzooxazol ylene), a substituted or unsubstituted isobenzooxazolylene group, a substituted or unsubstituted triazolylene group, a substituted or unsubstituted oxadiazolylene group, a substituted or unsubstituted thiadiazolyl a lene group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted imidazopyridinylene group, and a substituted or unsubstituted imidazopyrimidinylene group;

The substituted pyrrolylene group, substituted imidazolylene group, substituted pyrazolylene group, substituted thiazolylene group, substituted isothiazolylene group, substituted oxazolylene group, substituted isoxazolylene group, substituted pyridinyl Ren group, substituted pyrazinylene group, substituted pyrimidinylene group, substituted pyridazinylene group, substituted isoindolylene group, substituted indolylene group, substituted indazolylene group, substituted quinolinylene group, substituted Isoquinolinylene group, substituted benzoquinolinylene group, substituted quinoxalinylene group, substituted quinazolinylene group, substituted phenanthridinylene group, substituted acridinylene group, substituted phenanthrolinylene group, substituted substituted phenazinylene group, substituted benzoimidazolylene group, substituted isobenzothiazolylene group, substituted benzoxazolylene group, substituted isobenzoxazolylene group, substituted triazolylene group, substituted oxadiazolylene group, substituted At least one of at least one of the substituents of the thiadiazolylene group, the substituted triazinylene group, the substituted imidazopyridinylene group, and the substituted imidazopyrimidinylene group,

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy 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, penta Cenyl 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, pyri Dinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthi Ridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothia Zolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazole diary, imidazopyridinyl group and imidazopyrimidinyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, 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, Spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group 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, quinolyl group Nyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl, acridinyl, phenanthrolinyl, phena Zinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, di substituted with at least one of a benzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorene Nyl 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, rubysenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group 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, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl , acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group; and

-Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ); is selected from

wherein Q ₂₃ to Q ₂₅ and Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group , fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group It may be selected from a talazinyl group, a quinoxalinyl group, a cinolinyl group, and a quinazolinyl group, but is not limited thereto.

According to another embodiment, in Formula 81, E ₁ , E ₁₁ to E ₁₃ and E ₂₁ to E ₂₆ may each independently represent a substituted or unsubstituted imidazolylene group, a substituted or unsubstituted pyridinylene group, or a substituted or an unsubstituted pyrimidinylene group, a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted isoquinolinylene group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted phenanthrolinylene group, A substituted or unsubstituted benzoimidazolylene group, a substituted or unsubstituted triazolylene group, a substituted or unsubstituted oxadiazolylene group, a substituted or unsubstituted thiadiazolylene group, a substituted or unsubstituted triazinylene group, substituted or an unsubstituted imidazopyridinylene group, and a substituted or unsubstituted imidazopyrimidinylene group;

The substituted imidazolylene group, substituted pyridinylene group, substituted pyrimidinylene group, substituted quinolinylene group, substituted isoquinolinylene group, substituted quinazolinylene group, substituted phenanthrolinylene group, Substituted benzimidazolylene group, substituted triazolylene group, substituted oxadiazolylene group, substituted thiadiazolylene group, substituted triazinylene group, substituted imidazopyridinylene group and substituted imidazopyrimidinyl group At least one substituent of the ren group is

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

Phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyrida a zinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinolinyl group, and a quinazolinyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzo A carbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinolinyl group, a quinazolinyl group, and -Si (Q ₂₃ ) (Q ₂₄ ) (Q ₂₅ ) substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, Dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group phthalazinyl group, quinoxalinyl group, cinolinyl group and quinazolyl group nyl group; and

-Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ); is selected from;

wherein Q ₂₃ to Q ₂₅ and Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group , fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group It may be selected from a talazinyl group, a quinoxalinyl group, a cinolinyl group, and a quinazolinyl group, but is not limited thereto.

According to another embodiment, in Formula 81, E ₁ , E ₁₁ to E ₁₃ , and E ₂₁ to E ₂₆ may be each independently one of the following Formulas 80-1 to 80-27:

In Formulas 80-1 to 80-27,

Z ₁₁ and Z ₁₂ are independently of each other,

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy groups;

Phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyrida a zinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinolinyl group, and a quinazolinyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzo A carbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinolinyl group, a quinazolinyl group, and -Si (Q ₂₃ ) (Q ₂₄ ) (Q ₂₅ ) substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, Dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group phthalazinyl group, quinoxalinyl group, cinolinyl group and quinazolyl group nyl group; and

-Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ); is selected from;

wherein Q ₂₃ to Q ₂₅ and Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group , fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group a thalazinyl group, a quinoxalinyl group, a cinolinyl group, and a quinazolinyl group;

f1 is an integer selected from 1 to 3, f2 is 1 or 2, f3 is an integer from 1 to 4, f4 is an integer from 1 to 5, and * is a binding site to the core in Formula 81 , is a binding site with each of neighboring L ₁ , L ₁₁ to L ₁₃ and L ₂₁ to L ₂₆ or a binding site with each of neighboring E ₁ , E ₁₁ to E ₁₃ and E ₂₁ to E ₂₆ , and *' is a neighboring a binding site with each of E ₁ , E ₁₁ to E ₁₃ and E ₂₁ to E ₂₆ or a binding site with each of R ₁ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₆ .

In Formula 81, b1 in Formula 81 represents the number of E ₁ , and may be 0, 1, 2, 3, 4, or 5, for example, 1 or 2. When b1 is 2 or more, two or more E ₁ may be the same as or different from each other.

In Formula 81, b11 represents the number of E ₁₁ , and may be 0, 1, 2, 3, 4, or 5, for example, 0, 1, or 2, or as another example, 0 or 1. When b11 is 0, E ₁₁ is a single bond. When b11 is 2 or more, two or more E ₁₁ may be the same as or different from each other. Descriptions of b12, b13, and b21 to b26 may be understood with reference to the description of b11 and the structure of Formula 81.

In Formula 81, b1, b11 to b13, and b21 to b26 are each independently selected from an integer of 0 to 5, except when all of b1, b11 to b13 and b21 to b26 are 0. That is, at least one of E ₁ , E ₁₁ to E ₁₃ and E ₂₁ to E ₂₆ is necessarily present in Formula 81.

According to one embodiment, b1 in Formula 81 may be selected from an integer of 1 to 5. That is, b1 in Formula 81 is not 0, and E ₁ in Formula 81 may necessarily exist, but is not limited thereto.

As another example, in Formula 81, X ₂₂ is C-[(L ₂₂ ) _a22 -(E ₂₂ ) _b22 -(R ₂₂ ) _c22 ], and b22 is selected from an integer of 1 to 5 (eg, 1) can be

As another example, in Formula 81, X ₂₃ is C-[(L ₂₃ ) _a23 -(E ₂₃ ) _b23 -(R ₂₃ ) _c23 ], and b23 is selected from an integer of 1 to 5 (eg, 1) can be

In Formula 81, R ₁ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₆ are each independently selected from 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, 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 ratio -Aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heterocondensed polycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ) and -B( Q ₆ ) (Q ₇ ) may be selected.

According to one embodiment, in Formula 81, R ₁ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₆ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of salts thereof;

A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group ), fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group (phenalenyl), phenanthrenyl group (phenanthrenyl), anthracenyl group, fluoran Tenyl group (fluoranthenyl), triphenylenyl group (triphenylenyl), pyrenyl group (pyrenyl), chrysenyl group (chrysenyl), naphthacenyl group (naphthacenyl), picenyl group (picenyl), perylenyl group (perylenyl), penta Phenyl group (pentaphenyl), hexacenyl group (hexacenyl), pentacenyl group (pentacenyl), rubicenyl group (rubicenyl), coronenyl group (coronenyl), ovalenyl group (ovalenyl), pyrrolyl group (pyrrolyl), thiophenyl group ), furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl , pyridinyl group, pyrazinyl group (pyrazinyl), pyrimidinyl group (pyrimidinyl), pyridazinyl group (pyridazinyl), isoindolyl group (isoindolyl), indolyl group (indolyl), indazolyl group (indazolyl), Purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl , quinazolinyl group, cinnolinyl group, carbazolyl group ( carbazolyl), phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl (benzothiophenyl), isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl ), triazinyl group, dibenzofuranyl group (dibenzofuranyl), dibenzothiophenyl group (dibenzothiophenyl), benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, 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, Spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group 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, quinolyl group Nyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl, acridinyl, phenanthrolinyl, phena Zinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, di of a benzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a biphenyl group, and -Si( _Q33 )( _Q34 )( _Q35 ) At least one substituted, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, di benzofluorenyl 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, thiazolyl 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, phenane Tridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazole diary, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl group; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ) (provided that R ₁₁ to R ₁₃ are not -Si(Q ₃ )(Q ₄ )(Q ₅ ); is selected from;

wherein Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group , fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, It may be selected from an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group, but is not limited thereto.

According to another embodiment, in Formula 81,

R ₁ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₆ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group , a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, the formulas 44-1 to 44-31 and -Si(Q ₃ )(Q ₄ )(Q ₅ );

Wherein Q ₃ To Q ₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, cry Cenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quina It may be selected from a jolinyl group and a quinoxalinyl group, but is not limited thereto.

According to another embodiment, in Formula 81, R ₁ , R ₁₁ to R ₁₃ and R ₂₁ to R ₂₆ may be each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, and a hydroxyl group , cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy a group selected from the following formulas 85-1 to 85-27 and -Si(Q ₃ )(Q ₄ )(Q ₅ );

The Q ₃ to Q ₅ may be each independently selected from hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, and a naphthyl group, but are not limited thereto:

In Formulas 85-1 to 85-27, * is a binding site with a core in Formula 81, adjacent L ₁ , L ₁₁ to L ₁₃ and L ₂₁ to L ₂₆ or adjacent E ₁ , E ₁₁ to E ₁₃ and E ₂₁ to E ₂₆ , respectively.

According to another embodiment, in Formula 81,

X ₂₁ is C-[(L ₂₁ ) _a21 -(E ₂₁ ) _b21 -(R ₂₁ ) _c21 ], and X ₂₂ is C-[(L ₂₂ ) _a22 -(E ₂₂ ) _b22 -(R ₂₂ ) _c22 ] and X ₂₃ is C-[(L ₂₃ ) _a23 -(E ₂₃ ) _b23 -(R ₂₃ ) _c23 ], and X ₂₄ is C-[(L ₂₄ ) _a24 -(E ₂₄ ) _b24 -(R ₂₄ ) _c24 ], X ₂₅ is C-[(L ₂₅ ) _a25 -(E ₂₅ ) _b25 -(R ₂₅ ) _c25 ], and X ₂₆ is C-[(L ₂₆ ) _a26 -(E ₂₆ ) _b26 -(R ₂₆ ) _c26 ];

a21 to a26 and b21 to b26 are 0;

R ₂₁ to R ₂₆ 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 An acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, and —Si(Q ₃ )(Q ₄ )(Q ₅ ) is selected from;

c21 to c26 are 1;

The Q ₃ to Q ₅ may be each independently selected from hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, and a naphthyl group.

According to another embodiment, in Formula 81, b1 is 1, and at least one of c1 R _1s (eg, at least 2 of c1 R _1s ) is a substituted or unsubstituted C ₆ -C ₂₀ Can be selected from an aryl group, a substituted or unsubstituted C ₁ -C ₂₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group However, the present invention is not limited thereto.

For example, in Formula 81, b1 is 1, and at least one of c1 R _1s (eg, at least 2 of c1 R1s) is one of Formulas 44-1 to 44-31, for example For example, it may be one of Formulas 85-1 to 85-27, but is not limited thereto.

In Formula 81, c1 represents the number of R ₁ , and may be an integer of 1 to 5, for example, 1 to 3. The c1 may be 1, 2, or 1. When c1 is 2 or more, two or more R ₁ may be the same as or different from each other. Descriptions of c11 to c13 and c21 to c26 may be understood with reference to the description of c1 and the structure of Formula 81.

Meanwhile, the compound represented by Formula 81 may be represented by one of the following Formulas 81A to 81D:

<Formula 81A> <Formula 81B>

<Formula 81C> <Formula 81D>

For the description of L ₁ , a1 , E ₁ , R ₁ , R ₁₂ , R ₁₃ , R ₂₁ to R ₂₆ and c1 in Formulas 81A to 81D, refer to the description of Formula 81, and b1 is an integer of 1 to 5 is selected from That is, in Formulas 81A to 81D, E ₁ as defined in Formula 81 is necessarily present.

According to one embodiment, the compound represented by Formula 81 may be represented by Formula 81C or 81D, but is not limited thereto.

For example, the compound represented by Formula 81 is represented by one of Formulas 81A to 81D,

wherein L ₁ is selected from Formulas 12-1 to 12-33;

wherein a1 is 0, 1 or 2;

E ₁ is a substituted or unsubstituted imidazolylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted isoquinolyl group Nylene group, substituted or unsubstituted quinazolinylene group, substituted or unsubstituted phenanthrolinylene group, substituted or unsubstituted benzoimidazolylene group, substituted or unsubstituted triazolylene group, substituted or unsubstituted oxadia a zolylene group, a substituted or unsubstituted thiadiazolylene group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted imidazopyridinylene group, and a substituted or unsubstituted imidazopyrimidinylene group;

The substituted imidazolylene group, substituted pyridinylene group, substituted pyrimidinylene group, substituted quinolinylene group, substituted isoquinolinylene group, substituted quinazolinylene group, substituted phenanthrolinylene group, Substituted benzimidazolylene group, substituted triazolylene group, substituted oxadiazolylene group, substituted thiadiazolylene group, substituted triazinylene group, substituted imidazopyridinylene group and substituted imidazopyrimidinyl group At least one substituent of the ren group is

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

Phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyrida a zinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinolinyl group, and a quinazolinyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzo A carbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinolinyl group, a quinazolinyl group, and -Si (Q ₂₃ ) (Q ₂₄ ) (Q ₂₅ ) substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, Dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group phthalazinyl group, quinoxalinyl group, cinolinyl group and quinazolyl group nyl group; and

-Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ); is selected from;

wherein Q ₂₃ to Q ₂₅ and Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group , fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group a thalazinyl group, a quinoxalinyl group, a cinolinyl group, and a quinazolinyl group;

b1 is 1 or 2;

R ₁ , R ₁₂ , R ₁₃ and R ₂₁ to R ₂₆ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group , a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, the formulas 44-1 to 44-31 and -Si(Q ₃ )(Q ₄ )(Q ₅ );

Wherein Q ₃ To Q ₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, cry Cenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quina selected from a jolinyl group and a quinoxalinyl group;

c1 may be 1 or 2.

According to one embodiment, the condensed cyclic compound represented by Formula 81 is represented by one of Formulas 81A to 81D,

wherein L ₁ is one of Formulas 13-1 to 13-21;

wherein a1 is 0, 1 or 2;

E ₁ is one of Formulas 80-1 to 80-27;

R ₁ , R ₁₂ , R ₁₃ and R ₂₁ to R ₂₆ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group , a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, the formulas 85-1 to 85-27, and -Si(Q ₃ )(Q ₄ )(Q ₅ ), wherein at least one of c1 R ₁ is represented by one of Formulas 85-1 to 85-27;

wherein Q ₃ to Q ₅ are each independently selected from hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group and a naphthyl group;

c1 may be 1 or 2.

The compound represented by Formula 81 may be one of the following compounds (81)-1 to (81)-504, but is not limited thereto:

The compound represented by Chemical Formula 81 has a core in which a 5-membered ring is fused to a carbazole-based ring (see Chemical Formula 81' below). In addition, the case where all of b1, b11 to b13, and b21 to b26 in the compound represented by Formula 81 is 0 is excluded. That is, the compound represented by Formula 81 necessarily includes at least one of E ₁ , E ₁₁ to E ₁₃ and E ₂₁ to E ₂₆ , which are substituted or unsubstituted nitrogen-containing electron transport moieties. Accordingly, the compound represented by Chemical Formula 81 has excellent bipolar properties and HOMO and LUMO can be effectively controlled, and thus the efficiency of an organic light emitting device including the compound represented by Chemical Formula 81 can be improved.

<Formula 81'>

For example, the results of simulation evaluation using Gaussian for HOMO, LUMO and T ₁ energy levels for the following compounds (81)-A and (81)-B are shown in Table 7 below:

<Compound (81)-A>

<Compound (81)-B>

According to Table 7, the compound (81)-B has a high LUMO energy level of -0.642 eV due to the absence of an electron transporting moiety. This causes electron injection interference. For example, when the compound (81)-B is used alone as a host material in the light emitting layer, an imbalance between holes and electrons in the light emitting layer occurs, resulting in luminous efficiency of the organic light emitting device. may cause a decrease.

On the other hand, as can be seen from Table 7, the compound (81)-A has a very low T ₁ energy level of 2.124 eV, and is used as a material for an organic light emitting device, for example, a green host or a red host. difficult to do

However, in the condensed cyclic compound represented by Formula 81, as described above, a core in which a 5-membered ring is fused to a carbazole-based ring and a substituted or unsubstituted nitrogen-containing electron transporting moiety E ₁ , E ₁₁ to E ₁₃ and E ₂₁ to E ₂₆ are necessarily included, and thus the LUMO energy level value and the T1 energy level value suitable as a material for an organic light emitting device may be simultaneously included.

A method for synthesizing the condensed cyclic compound represented by Formula 81 can be easily recognized by those skilled in the art with reference to the following synthesis examples.

Formulas 91A to 91D

<Formula 91A>

<Formula 91B>

<Formula 91C>

<Formula 91D>

In Formulas 91A to 91D, A ₁ to A ₉ may be each independently selected from benzene, naphthalene, pyrene, fluorene, pyridine, pyrimidine, pyrazine, and carbazole.

According to an embodiment, A ₁ to A ₉ in Formulas 91A to 91D may each independently represent benzene, naphthalene, or carbazole, but is not limited thereto.

According to another embodiment, A ₁ to A ₉ in Formulas 91A to 91D may each independently represent benzene or carbazole, but is not limited thereto.

In Formulas 91A to 91D, A ₁ to A ₉ each represents a 7-membered ring adjacent to the core of Formulas 91A to 91D and a ring condensed while sharing carbon.

In Formulas 91A to 91D, A ₁ is substituted with c11 -(L ₁₁ ) _a11 -(R ₁₁ ) _b11 . The substituents of A ₂ to A ₉ may also be understood in the same manner.

In Formulas 91A to 91D,

X ₁ is N-[(L ₁ ) _a1 -(R ₁ ) _b1 ], C[(L ₂ ) _a2 -(R ₂ ) _b2 ][(L ₃ ) _a3 -(R ₃ ) _b3 ], Si[( L ₂ ) _a2 -(R ₂ ) _b2 ][(L ₃ ) _a3 -(R ₂ ) _b3 ], S, O, S(=O) or S(=O) ₂ ; X ₄ is N-[(L ₄ ) _a4 -(R ₄ ) _b4 ], C[(L ₅ ) _a5 -(R ₅ ) _b5 ][(L ₆ ) _a6 -(R ₆ ) _b6 ], Si[( L ₅ ) _a5 -(R ₅ ) _b5 ][(L ₆ ) _a6 -(R ₆ ) _b6 ], S, O, S(=O) or S(=O) ₂ ; X ₇ is N-[(L ₇ ) _a7 -(R ₇ ) _b7 ], C[(L ₈ ) _a8 -(R ₈ ) _b8 ][(L ₉ ) _a9 -(R ₉ ) _b9 ], Si[( L ₈ ) _a8 -(R ₈ ) _b8 ][(L ₉ ) _a9 -(R ₉ ) _b9 ], S, O, S(=O) or S(=O) ₂ .

According to an embodiment, in Formulas 91A to 91D, X ₁ is N-[(L ₁ ) _a1- (R ₁ ) _b1 ], and X ₄ is N-[(L ₄ ) _a4- (R ₄ ) _b4 ], and X ₇ may be N-[(L ₇ ) _a7 -(R ₇ ) _b7 ], but is not limited thereto.

According to one embodiment, in Formulas 91A to 91D, L ₁ to L ₉ and L ₁₁ to L ₁₉ are each independently

phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acetonitrile Naphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group (fluoranthrenylene), triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenyl pentaphenylene, hexacenylene, pyrrolylene, imidazolylene, pyrazolylene, pyridinylene, pyrazinylene, pyrimidi Nylene group (pyrimidinylene), pyridazinylene group (pyridazinylene), isoindolylene group (isoindolylene), indolylene group (indolylene), indazolylene group (indazolylene), purinylene group (purinylene), quinolinylene group (quinolinylene) , isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene , cinnolinylene, carbazolylene, phenanthridinylen e), acridinylene group, phenanthrolinylene group, phenazinylene group, benzooxazolylene group, benzoimidazolylene group, furanylene group, Benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group (isoxazolylene), oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzothiophenylene group ), a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene 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, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group , chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenyl group-substituted carbazolyl group , phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenyl group-substituted benzocarbazolyl group, phenyl group-substituted dibenzo A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, substituted with at least one of a carbazolyl group, an imidazopyrimidinyl group, an imidazopyridinyl group, and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) , azulenylene group, heptalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group , triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pyrrolylene group, imidazolylene group, pyrazolylene group, pyridinyl Ren group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, isoindolylene group, indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinolinylene group, carbazolylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoxa Zolylene group, benzoimidazolylene group, furanylene group, benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, isothiazolylene group, benzothiazolylene group, isoxazolylene group, oxazolylene group, Triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofura a nylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene group; is selected from

The Q ₃₃ to Q ₃₅ 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 car Acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, tri Phenylenyl group, pyrenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group , a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group.

According to another embodiment, L ₁ to L ₉ and L ₁₁ to L ₁₉ in Formulas 91A to 91D may be each independently selected from Formulas 92-1 to 92-34 below:

In Formulas 92-1 to 92-34,

Y ₁ is O, S, S(=O), S(=O) ₂ , C(Z ₃ )(Z ₄ ), N(Z ₅ ), or Si(Z ₆ )(Z ₇ );

Z ₁ To Z ₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl group an acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, Phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group , carbazolyl group, phenyl group-substituted carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenyl group-substituted a benzocarbazolyl group, a phenyl group-substituted dibenzocarbazolyl group, an imidazopyrimidinyl group, an imidazopyridinyl group, and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ );

The Q ₃₃ to Q ₃₅ 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 car Acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, tri Phenylenyl group, pyrenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group , a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyrimidinyl group and an imidazopyridinyl group;

d1 is an integer from 1 to 4; d2 is an integer from 1 to 3; d3 is an integer from 1 to 6; d4 is an integer from 1 to 8; d5 is 1 or 2; d6 is an integer from 1 to 5; * and *' may be binding sites with neighboring atoms.

For example, in Formulas 92-1 to 92-32, * represents a binding site with a core in Formulas 91A to 91D or a binding site with each of adjacent L ₁ to L ₉ and L ₁₁ to L ₁₉ in Formulas 91A to 91D, and Formula 92-1 In to 92-32, *' is a binding site with each of adjacent L ₁ to L ₉ and L ₁₁ to L ₁₉ or a binding site with each of R ₁ to R ₉ and R ₁₁ to R ₁₉ .

According to another embodiment, L ₁ to L ₉ and L ₁₁ to L ₁₉ in Formulas 91A to 91D may be each independently represented by one of Formulas 93-1 to 93-39, but are not limited thereto. :

In Formulas 93-1 to 93-39, * and *' are binding sites with neighboring atoms.

In Formula 91A, a1 represents the number of L ₁ s, and may be 0, 1, 2, 3, 4, or 5, for example, 0, 1, or 2, and as another example, may be 0 or 1. When a1 is 0, *-(L ₁ ) _a1 -*' becomes a single bond. When a1 is 2 or more, two or more L ₁ may be the same as or different from each other. Descriptions of a4 and a7 in Formulas 91B to 91D may be understood with reference to the description of a1 and Formulas 91B to 91D.

In Formula 91A, a2 represents the number of L ₂ , and may be 0, 1, 2, 3, 4, or 5, for example, 0, 1, or 2, and as another example, may be 0 or 1. When a2 is 0, *-(L ₂ ) _a2 -*' becomes a single bond. When a2 is 2 or more, two or more L ₂ may be the same as or different from each other. Descriptions of a3, a5, a6, a8, and a9 in Formulas 91A to 91D may be understood with reference to description of a2 and Formulas 91A to 91D.

In Formula 91A, a11 represents the number of L ₁₁ and may be 0, 1, 2, 3, 4, or 5, for example, 0, 1, or 2. When a11 is 0, *-(L ₁₁ ) _a11 -*' 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 to a19 in Formulas 91A to 91D may be understood with reference to the description of a11 above.

According to one embodiment, in Formulas 91A to 91D, L ₁ to L ₉ and L ₁₁ to L ₁₉ are each independently selected from a phenylene group and a phenyl group-substituted phenylene group, and a1 to a9 and a11 to a19 are each other Independently, it may be 0, 1 or 2.

According to another embodiment, in Formulas 91A to 91D, *-(L ₁ ) _a1 -*', *-(L ₂ ) _a2 -*', *-(L ₃ ) _a3 -*', *-(L ₄ ) ) _a4 -*', *-(L ₅ ) _a5 -*', *-(L ₆ ) _a6 -*', *-(L ₇ ) _a7 -*', *-(L ₈ ) _a8 -*', *-(L ₉ ) _a9 -*', *-(L ₁₁ ) _a11 -*', *-(L ₁₂ ) _a12 -*', *-(L ₁₃ ) _a13 -*', *-(L ₁₄ ) _a14 -*', *-(L ₁₅ ) _a15 -*', *-(L ₁₆ ) _a16 -*', *-(L ₁₇ ) _a17 -*', *-(L ₁₈ ) _a18 -*' and * -(L ₁₉ ) _a19 -*' may be each independently selected from a single bond and the following structural formulas, but is not limited thereto.

In Formulas 91A to 91D, R _{1 ,} R ₄ and R ₇ are each independently

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 및A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group ), fluorenyl group (fluorenyl), spiro-fluorenyl group, phenalenyl group (phenalenyl), phenanthrenyl group (phenanthrenyl), anthracenyl group (anthracenyl), fluoranthrenyl group (fluoranthrenyl), triphenylenyl group ( triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl , pyrrolyl group (pyrrolyl), imidazolyl group (imidazolyl), pyrazolyl group (pyrazolyl), pyridinyl group (pyridinyl), pyrazinyl group (pyrazinyl), pyrimidinyl group (pyrimidinyl), pyridazinyl group (pyridazinyl), isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, purinyl Thalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthridinyl group, Acridinyl, phenanthrolinyl, phenazinyl, benzooxazolyl, benzoimidazolyl, furanyl, benzofuranyl, thiophenyl group nyl), benzothiophenyl, thiazolyl, isothiazolyl, benzothiazolyl, isoxazolyl, oxazolyl, triazole Diary, tetrazolyl group, oxadiazolylene, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imida Zopyridimidinyl group, imidazopyridinyl group

group represented by

a group represented by , and

group represented by ; and

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 중에서 선택될 수 있으나, 이에 한정되는 것은 아니다. Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pi Renyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, A quinoxalinyl group, a carbazolyl group, a phenyl group-substituted carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, phenyl group-substituted with at least one of a substituted benzocarbazolyl group, a phenyl group-substituted dibenzocarbazolyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenane Threnyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolyl group phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaph Tyl group, fluorenyl group, spiro-fluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group , perylenyl group, pentaphenyl group, hexacenyl group, pyrrolyl group, imidazolyl group, pyrazolyl 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, acridi nyl group, phenanthrolinyl group, phenazinyl group, benzooxazolyl group, benzoimidazolyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, Triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, imidazopyridinyl group,

group represented by

a group represented by , and

group represented by ; may be selected from, but is not limited thereto.

According to another embodiment, in Formulas 91A to 91D, R ₂ , R ₃ , R ₅ , R ₆ , R ₈ , R ₉ , R ₁₁ to R ₁₉ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹;Phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyrida A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, substituted with at least one of a zinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinolinyl group, and a quinazolinyl group; Azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthrenyl group, triphenylenyl group, pi Renyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyri Dazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cy Nolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzooxazolyl group, benzoimidazolyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazole Diary, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarba Zolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, imidazopyridinyl group,

group represented by

a group represented by , and

group represented by ;

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 및Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pi Renyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, A quinoxalinyl group, a carbazolyl group, a phenyl group-substituted carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, phenyl group-substituted with at least one of a substituted benzocarbazolyl group, a phenyl group-substituted dibenzocarbazolyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenane Threnyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolyl group phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaph Tyl group, fluorenyl group, spiro-fluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group , perylenyl group, pentaphenyl group, hexacenyl group, pyrrolyl group, imidazolyl group, pyrazolyl 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, acridi nyl group, phenanthrolinyl group, phenazinyl group, benzooxazolyl group, benzoimidazolyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, Triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, imidazopyridinyl group,

group represented by

a group represented by , and

group represented by ; and

-N(Q ₁ )(Q ₂ ) or -Si(Q ₃ )(Q ₄ )(Q ₅ ) (Wherein, Q ₁ to Q ₅ are independently of each other, hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ - C ₂₀ Alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinolinyl group, and a quinazolinyl group); is selected from

In Formulas 91A to 91D, when A ₁ to A ₃ are all benzene, at least one of R ₁₁ to R ₁₃ is,

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 및Pyrrolyl group, imidazolyl group, pyrazolyl 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, benzoxa Zolyl group, benzoimidazolyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetra Zolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, imidazopyridinyl group,

group represented by

a group represented by , and

group represented by ; and

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 중에서 선택될 수 있다. Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pi Renyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, A quinoxalinyl group, a carbazolyl group, a phenyl group-substituted carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, A phenyl group-substituted benzocarbazolyl group, a phenyl group-substituted dibenzocarbazolyl group, an imidazopyrimidinyl group and at least one of an imidazopyridinyl group substituted with a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a 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, benzooxazolyl group, benzoimidazolyl group, furanyl group, benzofuranyl group , thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzo furanyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, imidazopyridinyl group,

group represented by

a group represented by , and

group represented by ; can be selected from

When all of A ₁ to A ₃ in Formula 91A are benzene, at least one of R ₁₁ to R ₁₃ is a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ hetero a cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

According to another embodiment, regardless of A ₁ to A ₃ in Formula 91A, at least one of R ₁₁ to R ₁₃ is a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₁ It may be selected from a -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

According to another embodiment, in Formulas 91A to 91D,

R ₁ , R ₄ and R ₇ are each independently represented by one of the following Chemical Formulas 94-1 to 94-32;

R ₂ , R ₃ , R ₅ , R ₆ , R ₈ , R ₉ , R ₁₁ to R ₁₉ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

Formulas 94-1 to 94-32; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ) (wherein Q ₃ to Q ₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthra Cenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group group, triazinyl group, quinolinyl group, isoquinolinyl group, phthalazinyl group, quinoxalinyl group, cinolinyl group and quinazolinyl group); selected from among

In Formulas 91A to 91D, when A ₁ to A ₃ are all benzene, at least one of R ₁₁ to R ₁₃ is selected from the following Formulas 94-5 to 94-32 (provided that one of R ₁₁ to R ₁₃ is selected from Formula 94- 5 to 94-8, Y ₃₁ in Formulas 94-5 to 94-8 may be represented by one of O, S, or N(Z ₃₅ ):

In Formulas 94-1 to 94-32,

Y ₃₁ is O, S, C(Z ₃₃ )(Z ₃₄ ), N(Z ₃₅ ) or Si(Z ₃₆ )(Z ₃₇ );

Z ₃₁ to Z ₃₇ 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 Acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenane Trenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, Carbazolyl group, phenyl group-substituted carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenyl group-substituted a benzocarbazolyl group, a phenyl group-substituted dibenzocarbazolyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group;

e1 is an integer from 1 to 5; e2 is an integer from 1 to 7; e3 is an integer from 1 to 3; e4 is an integer from 1 to 4; e5 is 1 or 2; e6 is an integer from 1 to 6; * is a binding site with a neighboring atom.

For example, e1, e2, e3, e4, e5, and e6 in Formulas 94-1 to 94-29 may each independently be 1 or 2.

According to another embodiment, in Formulas 91A to 91D,

R ₁ , R ₄ and R ₇ are each independently represented by one of the following Chemical Formulas 95-1 to 95-60;

R ₂ , R ₃ , R ₅ , R ₆ , R ₈ , R ₉ , R ₁₁ to R ₁₉ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

Formulas 95-1 and 95-60; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ) (wherein Q ₃ to Q ₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthra Cenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group group, triazinyl group, quinolinyl group, isoquinolinyl group, phthalazinyl group, quinoxalinyl group, cinolinyl group and quinazolinyl group); selected from among

When A ₁ to A ₃ in Formulas 91A to 91D are all benzene, at least one of R ₁₁ to R ₁₃ may be represented by one of Formulas 95-10 to 95-17 and 95-22 to 95-60 :

In Formula 91A, b1 represents the number of R ₁ , and may be selected from an integer of 1 to 5, for example, an integer of 1 to 3. The b1 may be 1, 2, or 1. When b1 is 2 or more, two or more R ₁ may be the same as or different from each other. Descriptions of b2 to b9 in Formulas 91A to 91D may be understood with reference to the description of b1 and Formulas 91A to 91D.

In Formula 91A, b11 represents the number of R ₁₁ , and may be an integer of 1 to 5, for example, 1 to 3. The b11 may be 1, 2, or 1. When b11 is 2 or more, two or more R ₁₁ may be the same as or different from each other. Descriptions of b12 to b19 in Formulas 91A to 1D may be understood with reference to the description of b11 and Formulas 91A to 91D.

In Formula 91A, c11 represents the number of moieties represented by *-(L ₁₁ ) _a11 -(R ₁₁ ) _b11 , and is selected from an integer of 1 to 4. c11 may be 1 or 2. When c11 is 2 or more, two or more *-(L ₁₁ ) _a11 -(R ₁₁ ) _b11 are the same as or different from each other. Descriptions of c12 to c19 in Formulas 91A to 91D may be understood with reference to the description of c11 and Formulas 91A to 91D.

According to one embodiment, in Formulas 91A to 91D, c11 to c19 may all be 1.

For example, in Formula 91A

A ₁ to A ₃ are each independently benzene or carbazole;

X ₁ is N-[(L ₁ ) _a1- (R ₁ ) _b1 ], S or O;

L ₁ and L ₁₁ to L ₁₃ are independently of each other,

a phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, and a triazinylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, Chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenyl group-substituted carbazolyl group, Phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenyl group-substituted benzocarbazolyl group, phenyl group-substituted dibenzocarba a phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, and a triazinylene group substituted with at least one of a zolyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group; is selected from;

a1 and a11 to a13 are each independently 0, 1 or 2;

R ₁ and R ₁₁ to R ₁₃ are independently of each other,

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 및Phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group , isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazole group Diary, imidazopyrimidinyl group, imidazopyridinyl group,

group represented by

a group represented by , and

group represented by ; and

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 중에서 선택되고;Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, Chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenyl group-substituted carbazolyl group, Phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenyl group-substituted benzocarbazolyl group, phenyl group-substituted dibenzocarba A phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, Pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, imidazopyridinyl group,

group represented by

a group represented by , and

group represented by ; is selected from;

When A ₁ to A ₃ are all benzene, at least one of R ₁₁ to R ₁₃ is,

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 및Pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, imidazopyridinyl group,

group represented by

a group represented by , and

group represented by ; and

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 중에서 선택되고; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, Chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenyl group-substituted carbazolyl group, Phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenyl group-substituted benzocarbazolyl group, phenyl group-substituted dibenzocarba a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, Quinoxalinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, imida zopyridinyl group,

group represented by

a group represented by , and

group represented by ; is selected from;

b1 and b11 to b13 are each independently 1 or 2,

c11 to c13 may be 1 or 2, but is not limited thereto.

On the other hand, in Formulas 91B to 91D,

A ₄ to A ₉ are each independently benzene or carbazole;

X ₄ is N-[(L ₄ ) _a4 -(R ₄ ) _b4 ], S or O, X ₄ is N-[(L ₇ ) _a7 -(R ₇ ) _b7 ], S or O;

L ₄ , L ₉ , L ₁₄ to L ₁₉ are each independently,

a phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, and a triazinylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, Chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenyl group-substituted carbazolyl group, Phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenyl group-substituted benzocarbazolyl group, phenyl group-substituted dibenzocarba a phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, and a triazinylene group substituted with at least one of a zolyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group; is selected from;

a4, a7, a14 to a19 are each independently 0, 1 or 2;

R ₄ and R ₇ are independently of each other,

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 및Phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group , isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazole group Diary, imidazopyrimidinyl group, imidazopyridinyl group,

group represented by

a group represented by , and

group represented by ; and

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 중에서 선택되고;Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, Chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenyl group-substituted carbazolyl group, Phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenyl group-substituted benzocarbazolyl group, phenyl group-substituted dibenzocarba A phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, Pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, imidazopyridinyl group,

group represented by

a group represented by , and

group represented by ; is selected from;

R ₁₄ to R ₁₉ are each independently,

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 및Phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group , isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazole group Diary, imidazopyrimidinyl group, imidazopyridinyl group,

group represented by

a group represented by , and

group represented by ; and

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 중에서 선택되고; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, Chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenyl group-substituted carbazolyl group, Phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenyl group-substituted benzocarbazolyl group, phenyl group-substituted dibenzocarba A phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, Pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, imidazopyridinyl group,

group represented by

a group represented by , and

group represented by ; is selected from;

b4, b7, b14 to b19 are each independently 1 or 2;

c11 to c19 may each independently be 1 or 2, but is not limited thereto.

According to one embodiment, the compound represented by one of 91A to 91D is represented by Formula 91A,

At least one of R ₁₁ to R ₁₃ in Formula 91A is a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₁ It may be selected from a -C ₆₀ heteroaryl group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

According to another embodiment, the condensed cyclic compound is represented by one of Formulas 91B to 91D,

In Formulas 91B to _91D , X ₄ is N-[(L ₄ ) a4-(R ₄ ) _b4 ],

At least one of R ₄ and R ₁₄ to R ₁₉ in Formulas 91B to 91D is a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or It may be selected from an unsubstituted C ₁ -C ₆₀ heteroaryl group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

According to another embodiment, the compound represented by one of 91A to 91D is represented by one of Formulas 91B to 91D,

In Formulas 91B to _91D , X ₄ is N-[(L ₄ ) a4-(R ₄ ) _b4 ], and X ₇ is N-[(L ₇ ) _a7 -(R ₇ ) _b7 ],

In Formulas 91B to 91D, R ₄ , R ₇ and R ₁₄ to R ₁₉ are,

hydrogen, 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, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or A salt thereof, a C ₃ -C ₁₀ cycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₆ -C ₆₀ aryl group, and a monovalent non-aromatic condensed polycyclic group substituted with at least one of a 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 ₃ -C ₁₀ cycloalkenyl group, C ₆ -C ₆₀ aryl group and monovalent non-aromatic condensed polycyclic group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts 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 ₃ -C ₁₀ cycloalkenyl group , C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₆ -C ₆₀ aryl group and monovalent substituted with at least one of a C ₆ -C ₆₀ aryl group and a monovalent non-aromatic condensed polycyclic group a non-aromatic condensed polycyclic group; can be selected from

According to one embodiment, the compound represented by one of 91A to 91D may be represented by one of the following Chemical Formulas 91A(1) to 91A(4):

<Formula 91A(1)>

<Formula 91A(2)>

<Formula 91A(3)> <Formula 91A(4)>

For the description of the substituents in Formulas 91A(1) to 91A(4), refer to the descriptions for 91A to 91D, and at least among R ₁₂ of Formula 91A(1), R ₁₁ and R ₁₂ of 91A(2) One, R ₁₂ of Formula 91A(3) and R ₁₃ of Formula 91A(4) are a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalke It may be selected from a nyl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formulas 91A(1) to 91A(4),

L ₁ and L ₁₁ to L ₁₃ are independently of each other,

a phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, and a triazinylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, Chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenyl group-substituted carbazolyl group, Phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenyl group-substituted benzocarbazolyl group, phenyl group-substituted dibenzocarba a phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, and a triazinylene group substituted with at least one of a zolyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group; is selected from;

a1 and a11 to a13 are each independently 0, 1 or 2;

R ₁ and R ₁₁ are independently of each other,

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 및Phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group , isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazole group Diary, imidazopyrimidinyl group, imidazopyridinyl group,

group represented by

a group represented by , and

group represented by ; and

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 중에서 선택되고; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, Chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenyl group-substituted carbazolyl group, Phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenyl group-substituted benzocarbazolyl group, phenyl group-substituted dibenzocarba A phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, Pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, imidazopyridinyl group,

group represented by

a group represented by , and

group represented by ; is selected from;

R ₁₂ and R ₁₃ are independently of each other,

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 및Pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, imidazopyridinyl group,

group represented by

a group represented by , and

group represented by ; and

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 중에서 선택되고; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, Chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenyl group-substituted carbazolyl group, Phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenyl group-substituted benzocarbazolyl group, phenyl group-substituted dibenzocarba a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, Quinoxalinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, imida zopyridinyl group,

group represented by

a group represented by , and

group represented by ; is selected from;

b1 and b11 to b13 may each independently be 1 or 2.

According to another embodiment, the condensed cyclic compound is represented by one of Chemical Formulas 91A(1) to 91A(4), wherein in Chemical Formulas 91A(1) to 91A(4),

L ₁ and L ₁₁ to L ₁₃ are each independently represented by one of Formulas 92-1 to 92-34 (eg, one of Formulas 93-1 to 93-39);

a1 and a11 to a13 are each independently 0, 1 or 2;

R ₁ and R ₁₁ are each independently represented by one of Formulas 94-1 to 94-32 (eg, one of Formulas 5-1 to 5-60);

R ₁₂ and R ₁₃ are each independently selected from Formulas 94-5 to 94-32 (provided that when R ₁₂ and R ₁₃ are represented by Formulas 94-5 to 94-8, in Formulas 94-5 to 4-8 Y ₃₁ is O, S, or N(Z ₃₅ ));

b1 and b11 to b13 may each independently be 1 or 2.

Alternatively, the condensed cyclic compound may be represented by the following Chemical Formulas 91A(5), 91A(6) or 91B(1):

<Formula 91A(5)>

<Formula 91A(6)>

<Formula 91B(1)>

For the description of the substituents in Formulas 91A(5), 91A(6), and 91B(1), refer to the descriptions of 91A to 91D.

For example, in Formulas 91A(5), 91A(6), and 91B(1),

L ₁ , L ₄ , L ₇ , L ₁₁ , L ₁₂ , L ₁₄ and L ₁₉ are independently of each other,

a phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, and a triazinylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, Chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenyl group-substituted carbazolyl group, Phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenyl group-substituted benzocarbazolyl group, phenyl group-substituted dibenzocarba a phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, and a triazinylene group substituted with at least one of a zolyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group; is selected from;

a1, a4, a7, a11, a12, a14 and a19 are each independently 0, 1 or 2;

R ₁ , R ₄ , R ₇ and R ₁₂ are independently of each other,

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 및Phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group , isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazole group Diary, imidazopyrimidinyl group, imidazopyridinyl group,

group represented by

a group represented by , and

group represented by ; and

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 중에서 선택되고;Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, Chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenyl group-substituted carbazolyl group, Phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenyl group-substituted benzocarbazolyl group, phenyl group-substituted dibenzocarba A phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, Pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, imidazopyridinyl group,

group represented by

a group represented by , and

group represented by ; is selected from;

R ₁₁ , R ₁₄ and R ₁₉ are independently of each other,

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 및Phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group , isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazole group Diary, imidazopyrimidinyl group, imidazopyridinyl group,

group represented by

a group represented by , and

group represented by ; and

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 중에서 선택되고; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, Chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenyl group-substituted carbazolyl group, Phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenyl group-substituted benzocarbazolyl group, phenyl group-substituted dibenzocarba A phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, Pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, imidazopyridinyl group,

group represented by

a group represented by , and

group represented by ; is selected from;

b1, b4, b7, b11, b12, b14 and b19 may each independently be 1 or 2.

As another example, in Formulas 91A(5), 91A(6) and 91B(1),

L ₁ , L ₄ , L ₇ , L ₁₁ , L ₁₂ , L ₁₄ and L ₁₉ are each independently one of Formulas 92-1 to 92-34 (eg, Formulas 93-1 to 93-39 above) one of them);

a1, a4, a7, a11, a12, a14 and a19 are each independently 0, 1 or 2;

R ₁ , R ₄ , R ₇ and R ₁₂ are each independently represented by one of Formulas 94-1 to 94-32 (eg, one of Formulas 95-1 to 95-60);

R ₁₁ , R ₁₄ and R ₁₉ are independently of each other,

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group; and

represented by one of Formulas 94-1 to 94-32 (eg, one of Formulas 95-1 to 95-60);

b1, b4, b7, b11, b12, b14 and b19 may each independently be 1 or 2.

According to another embodiment, at least one of R ₁₁ and R ₁₂ of Formulas 91A(5) and 91A(6) and at least one of R ₁₄ and R ₁₉ of Formula 91B(1) are, independently of each other, the Formulas 94-5 to 94-32 (provided that when R ₁₂ and R ₁₃ are in Formulas 94-5 to 94-8, Y ₃₁ in Formulas 94-5 to 94-8 is O, S or N (Z ₃₅ )) (for example, one of Chemical Formulas 95-10 to 95-17 and 95-22 to 95-60), but is not limited thereto.

As another example, the compound represented by one of Formulas 91A to 91D is represented by Formula 91B-1(1), wherein in Formula 91B(1),

L ₄ , L ₇ , L ₁₄ and L ₁₉ are independently of each other,

a phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, and a triazinylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, Chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenyl group-substituted carbazolyl group, Phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenyl group-substituted benzocarbazolyl group, phenyl group-substituted dibenzocarba a phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, and a triazinylene group substituted with at least one of a zolyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group; is selected from;

a4, a7, a14 and a19 are each independently 0, 1 or 2;

R ₄ and R ₇ are independently of each other,

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 및Phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group , isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazole group Diary, imidazopyrimidinyl group, imidazopyridinyl group,

group represented by

a group represented by , and

group represented by ; and

로 표시되는 그룹,

로 표시되는 그룹, 및

로 표시되는 그룹; 중에서 선택되고;Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, Chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenyl group-substituted carbazolyl group, Phenanthrolinyl group, benzoimidazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenyl group-substituted benzocarbazolyl group, phenyl group-substituted dibenzocarba A phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, Pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, triazinyl group , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyrimidinyl group, imidazopyridinyl group,

group represented by

a group represented by , and

group represented by ; is selected from;

R ₁₄ and 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 carboxyl group an acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group and a naphthyl group,

b4 and b19 may each independently be 1 or 2.

The compound represented by Formulas 91A to 91D may be one of the following compounds (91)-1 to (91)-121, but is not limited thereto:

When all of A ₁ to A ₃ in Formula 91A are benzene, at least one of R ₁₁ to R ₁₃ is a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, or a substituted or unsubstituted C ₁ -C ₁₀ heterocyclo an alkenyl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, an electron transporting moiety.

According to another embodiment, regardless of A ₁ to A ₃ in Formula 91A, at least one of R ₁₁ to R ₁₃ is a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₁ a -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, an electron transporting moiety.

Accordingly, the electron-transporting moiety is not "central N" in the core of Formula 91A (when X ₁ = N-[(L ₁ ) _a1- (R ₁ ) _b1 ]), Formula 91A Since it is necessarily bound to one of A ₁ to A ₃ among the cores, it may have excellent chemical and electrical stability (see Chemical Formula 91A' below).

<Formula 91A'>

The compounds (91)-3, (91)-5, (91)-8, (91)-10, (91)-11, (91)-13, (91)-14, (91)-59, (91)-82, (91)-84, (91)-88, (91)-91, (91)-96, (91)-116, (91)-120 and (91)-121 and the following compounds HOMO, LUMO, singlet (S1) energy level and triplet (T1) energy level for (91)-A were optimized for structure at (B3LYP, 6-31G(d,p) level using the DFT method of Gaussian program. ) The evaluation results are shown in Table 8 below.

<Compound (91)-A>

From Table 8, the compounds (91)-3, (91)-5, (91)-8, (91)-10, (91)-11, (91)-13, (91)-14, ( 91)-59, (91)-82, (91)-84, (91)-88, (91)-91, (91)-96, (91)-116, (91)-120 and (91) It can be seen that the HOMO energy level of -121 is higher than the HOMO energy level of the compound (91)-A. That is, the compounds (91)-3, (91)-5, (91)-8, (91)-10, (91)-11, (91)-13, (91)-14, (91)- 59, (91)-82, (91)-84, (91)-88, (91)-91, (91)-96, (91)-116, (91)-120 and (91)-121 of The absolute value of the HOMO energy level is smaller than the absolute value of the HOMO energy level of the compound (91)-A. Thus, the compounds (91)-3, (91)-5, (91)-8, (91)-10, (91)-11, (91)-13, (91)-14, (91)- 59, (91)-82, (91)-84, (91)-88, (91)-91, (91)-96, (91)-116, (91)-120 and (91)-121; The organic light emitting device employing the same condensed cyclic compound may have a low driving voltage, and thus improved efficiency and lifespan characteristics.

In addition, from Table 8, the compounds (91)-3, (91)-5, (91)-8, (91)-10, (91)-11, (91)-13, (91)-14 , (91)-59, (91)-82, (91)-84, (91)-88, (91)-91, (91)-96, (91)-116, (91)-120 and ( It can be seen that the LUMO energy level of 91)-121 is lower than the HOMO energy level of the compound (91)-A. That is, the compounds (91)-3, (91)-5, (91)-8, (91)-10, (91)-11, (91)-13, (91)-14, (91)- 59, (91)-82, (91)-84, (91)-88, (91)-91, (91)-96, (91)-116, (91)-120 and (91)-121 of The absolute value of the LUMO energy level is greater than the absolute value of the HOMO energy level of the compound (91)-A. Thus, the compounds (91)-3, (91)-5, (91)-8, (91)-10, (91)-11, (91)-13, (91)-14, (91)- 59, (91)-82, (91)-84, (91)-88, (91)-91, (91)-96, (91)-116, (91)-120 and (91)-121 and Since the same condensed cyclic compound can achieve a balance between hole and electron transport, it can be usefully used as a material for an organic light emitting device, for example, a host material in a light emitting layer.

On the other hand, from Table 8, it can be seen that the compounds (91)-82, (91)-84 and (91)-88 have very high LUMO energy levels. That is, the absolute values of the LUMO energy levels of the compounds (91)-82, (91)-84, and (91)-88 are relatively small compared to the absolute values of the LUMO energy levels of the other compounds. Accordingly, the condensed cyclic compounds such as compounds (91)-82, (91)-84 and (91)-88 may have excellent hole transport ability, and thus materials for an organic light emitting device, for example, an anode and a light emitting layer It can be usefully used as a material for a hole transport region between the layers, or as a co-host material in the light emitting layer.

From Table 8, it can be seen that the compounds represented by one of Chemical Formulas 91A to 91D have electrical properties suitable for use as a material for an organic light emitting device.

Formula 101

<Formula 101>

In Formula 101, X ₁ is N[(L ₁ ) _a1- (R ₁ ) _b1 ], C[(L ₂ ) _a2- (R ₂ ) _b2 ][(L ₃ ) _a3- (R ₃ ) _b3 ] , Si[(L ₂ ) _a2- (R ₂ ) _b2 ][(L ₃ ) _a3- (R ₃ ) _b3 ], S and O; X ₂ is N[(L ₄ ) _a4 -(R ₄ ) _b4 ], C[(L ₅ ) _a5 -(R ₅ ) _b5 ][(L ₆ ) _a6 -(R ₆ ) _b6 ], Si[(L) ₅ ) _a5 -(R ₅ ) _b5 ][(L ₆ ) _a6 -(R ₆ ) _b6 ], S and O; X ₃ is N[(L ₇ ) _a7 -(R ₇ ) _b7 ], C[(L ₈ ) _a8 -(R ₈ ) _b8 ][(L ₉ ) _a9 -(R ₉ ) _b9 ], Si[(L) ₈ ) _a8 -(R ₈ ) _b8 ][(L ₉ ) _a9 -(R ₉ ) _b9 ], S and O.

However, in Formula 101, when X ₂ is N[(L ₄ ) _a4- (R ₄ ) _b4 ], i) X ₁ is C[(L ₂ ) _a2- (R ₂ ) _b2 ][(L ₃ ) ) _a3 -(R ₃ ) _b3 ] or Si[(L ₂ ) _a2 -(R ₂ ) _b2 ][(L ₃ ) _a3 -(R ₃ ) _b3 ], and X ₃ is N[(L ₇ ) _a7 - (R ₇ ) _b7 ], C[(L ₈ ) _a8 -(R ₈ ) _b8 ][(L ₉ ) _a9 -(R ₉ ) _b9 ], Si[(L ₈ ) _a8 -(R ₈ ) _b8 ][ (L ₉ ) _a9 -(R ₉ ) _b9 ], S and O, or ii) X ₁ is selected from N[(L ₁ ) _a1- (R ₁ ) _b1 ], S and O, and X ₃ is C[(L ₈ ) _a8 -(R ₈ ) _b8 ][(L ₉ ) _a9 -(R ₉ ) _b9 ] or Si[(L ₈ ) _a8 -(R ₈ ) _b8 ][(L ₉ ) _a9 - (R ₉ ) _b9 ]. That is, in Formula 101, when X ₂ is N[(L ₄ ) _a4- (R ₄ ) _b4 ], at least one of X ₁ and X ₃ must include C or Si.

Meanwhile, in Formula 101, X ₁ is C[(L ₂ ) _a2 -(R ₂ ) _b2 ][(L ₃ ) _a3 -(R ₃ ) _b3 ], X ₂ is S, and X ₃ is C[ (L ₈ ) _a8 -(R ₈ ) _b8 ][(L ₉ ) _a9 -(R ₉ ) _b9 ] is excluded.

Accordingly, the compound represented by Chemical Formula 101 may be represented by one of Chemical Formulas 101(1) to 101(115) in which X ₁ , X ₂ and X ₃ are each defined as follows:

According to one embodiment, in Formula 101, X ₂ is C[(L ₅ ) _a5 -(R ₅ ) _b5 ][(L ₆ ) _a6 -(R ₆ ) _b6 ], Si[(L ₅ ) _a5 - (R ₅ ) _b5 ][(L ₆ ) _a6 -(R ₆ ) _b6 ], S and O (refer to Formulas 101(17) to 101(115)).

According to another embodiment, in Formula 101, X ₁ = X ₂ = X ₃ ; X ₁ = X ₂ and X ₂ ≠ X ₃ ; X ₁ ≠ X ₂ and X ₂ = X ₃ ; or X ₁ ≠ X ₂ ≠ X ₃ .

For example, in Formula 101, X ₁ = X ₂ and X ₂ ≠ X ₃ ; X ₁ ≠ X ₂ and X ₂ = X ₃ ; Alternatively, it may be X ₁ ≠ X ₂ ≠ X ₃ , but is not limited thereto.

According to another embodiment, in Formula 101, X ₁ is N[(L ₁ ) _a1- (R ₁ ) _b1 ]; X ₂ is N[(L ₄ ) _a4- (R ₄ ) _b4 ]; Alternatively, X ₃ may be N[(L ₇ ) _a7 -(R ₇ ) _b7 ]. That is, in Formula 101, at least one of X ₁ , X ₂ , and X ₃ may include N.

According to another embodiment, in Formula 101, X ₁ may be N[(L ₁ ) _a1- (R ₁ ) _b1 ], and X ₃ may be N[(L ₇ ) _a7 -(R ₇ ) _b7 ]. (See, for example, Chemical Formula 101(91) above).

According to another embodiment, the compound represented by Formula 101 may be represented by Formula 101(81), 101(70), 101(15), 101(92), or 101(106), but is limited thereto. it is not

In Formula 101, L ₁ to L ₉ , L ₁₁ and L ₁₂ may each independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, or a substituted Or an unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or unsubstituted 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 condensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed polycyclic group) and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group (substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic group).

According to one embodiment, in Formula 101, L ₁ to L ₉ , L ₁₁ and L ₁₂ are each independently

phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acetonitrile Naphthylene group (acenaphthylene), fluorenylene group (fluorenylene), spiro-fluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group (phenanthrenylene) , anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene ), perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, rubicenylene group, coronenylene group, ovalenylene group (ovalenylene), pyrrolylene group, thiophenylene, furanylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolyl Ren group (isothiazolylene), oxazolylene group (oxazolylene), isoxazolylene group (isooxazolylene), pyridinylene group (pyridinylene), pyrazinylene group (pyrazinylene), pyrimidinylene group (pyrimidinylene), pyridazinylene group, isoindolylene, indolylene, indazolylene, purinylene, quinolinylene nylene), isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene ( quinazolinylene, cinnolinylene, carbazolylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzo An imidazolylene group, a benzofuranylene group, a benzothiophenylene group, an isobenzothiazolylene group, a benzooxazolylene group, an isobenzooxazolylene group, Triazolylene, tetrazolylene, oxadiazolylene, triazinylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolyl a ren group, a dibenzocarbazolylene group, an imidazopyridinylene group, and an imidazopyrimidinylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, 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, Spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thio groupphenyl 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, 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, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) At least one substituted, phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-fluorenylene group , benzofluorenylene group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenyl groupylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylenyl group, pentaphenylene group, hexacenylene group, pentacenylene group, rubysenylene group group, coronenylene group, ovalenylene group, pyrrolylene group, thiophenylene group, furanyl group, imidazolylene group, pyrazolylene group, thiazolylene group, isothiazolylene group, oxazolylene group, isoxazolyl Ren group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, isoindolylene group, indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzoqui Nolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinolinylene group, carbazolylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinyl group Rene group, benzoimidazolylene group, benzofuranylene group, benzothiophenylene group, isobenzothiazolylene group, benzoxazolylene group, isobenzoxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinyl a ren group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyridinylene group and an imidazopyrimidinylene group; may be selected from, but is not limited thereto. Here, Q ₃₃ to Q ₃₅ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group , carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, Fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, iso It may be selected from a quinolinyl group, a quinazolinyl group, and a quinoxalinyl group.

According to another embodiment, L ₁ to L ₉ , L ₁₁ and L ₁₂ in Formula 101 may be each independently selected from Formulas 12-1 to 12-37:

For example, * in Formulas 12-1 to 12-37 represents a binding site with a core in Formula 101 or a binding site with each of adjacent L ₁ to L ₉ , L ₁₁ and L ₁₂ in Formulas 12-1 to 2 In -37, *' is a binding site with each of adjacent L ₁ to L ₉ , L ₁₁ and L ₁₂ , or a binding site with each of R ₁ to R ₉ , R ₁₁ and R ₁₂ .

According to another embodiment, L ₁ to L ₉ , L ₁₁ and L ₁₂ in Formula 101 may be each independently selected from Formulas 103-1 to 103-59, but are not limited thereto:

In Formula 101, a1 represents the number of L ₁ s, and may be 0, 1, 2, 3, 4, or 5, for example, 0, 1, or 2, and as another example, may be 0 or 1. When a1 is 0, R ₁ is directly bonded to N. When a1 is 2 or more, two or more L ₁ may be the same as or different from each other. Descriptions of a4 and a7 may be understood with reference to the description of a1 and Chemical Formula 101.

In Formula 101, a2 represents the number of L ₂ , and may be 0, 1, 2, 3, 4, or 5, for example, 0, 1, or 2, and as another example, may be 0 or 1. When a2 is 0, R ₂ is directly bonded to C or Si. When a2 is 2 or more, two or more L ₂ may be the same as or different from each other. Descriptions of a3, a5, a6, a8, and a9 may be understood with reference to the description of a2 and Chemical Formula 101.

In Formula 101, a11 represents the number of L ₁₁ s, and may be 0, 1, 2, 3, 4, or 5, for example, 0, 1, or 2, or as another example, 0 or 1. When a11 is 0, R ₁₁ is directly bonded to C of the core of Formula 101. When a11 is 2 or more, two or more L ₁₁ may be the same as or different from each other.

In Formula 101, a12 represents the number of L ₁₂ s, and may be 0, 1, 2, 3, 4, or 5, for example, 0, 1, or 2, or as another example, 0 or 1. When a12 is 0, R ₁₂ is directly bonded to C of the core of Formula 101. When a12 is two or more, two or more L ₁₂ may be the same as or different from each other.

In Formula 101, R _{1 ,} R ₄ , and R ₇ may each independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, or a hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted A substituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, A substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a 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 and substituted or may be selected from an unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and in Formula 101, R ₂ , R ₃ , R ₅ , R ₆ , R ₈ , R ₉ , R ₁₁ and R ₁₂ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, Phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, 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 cyclic 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 an unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )( Q ₅ ) and -B(Q ₆ )(Q ₇ ); can be selected from

According to one embodiment, in Formula 101, R _{1 ,} R ₄ and R ₇ are each independently

로 표시되는 그룹; 및A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group ), fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group (phenalenyl), phenanthrenyl group (phenanthrenyl), anthracenyl group, fluoran Tenyl group (fluoranthenyl), triphenylenyl group (triphenylenyl), pyrenyl group (pyrenyl), chrysenyl group (chrysenyl), naphthacenyl group (naphthacenyl), picenyl group (picenyl), perylenyl group (perylenyl), penta Phenyl group (pentaphenyl), hexacenyl group (hexacenyl), pentacenyl group (pentacenyl), rubicenyl group (rubicenyl), coronenyl group (coronenyl), ovalenyl group (ovalenyl), pyrrolyl group (pyrrolyl), thiophenyl group ), furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl , pyridinyl group, pyrazinyl group (pyrazinyl), pyrimidinyl group (pyrimidinyl), pyridazinyl group (pyridazinyl), isoindolyl group (isoindolyl), indolyl group (indolyl), indazolyl group (indazolyl), Purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl , quinazolinyl group, cinnolinyl group, carbazolyl group ( carbazolyl), phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl (benzothiophenyl), isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl ), a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and

group represented by ; and

로 표시되는 그룹; 중에서 선택되고;Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, hep Thalenyl 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, 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, iso Indolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazole Diary, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, tria At least one of a zolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group. One substituted, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzo Fluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl 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, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indole group Diary, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrinyl group Dinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetra Zolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and

group represented by ; is selected from;

The Q ₃₃ to Q ₃₅ 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 car Acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorine Nyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolyl group a nyl group, a quinazolinyl group and a quinoxalinyl group; may be selected from, but is not limited thereto.

According to another embodiment, in Formula 101, R ₂ , R ₃ , R ₅ , R ₆ , R ₈ , R ₉ , R ₁₁ and R ₁₂ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group; C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

로 표시되는 그룹; 및A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group ), fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group (phenalenyl), phenanthrenyl group (phenanthrenyl), anthracenyl group, fluoran Tenyl group (fluoranthenyl), triphenylenyl group (triphenylenyl), pyrenyl group (pyrenyl), chrysenyl group (chrysenyl), naphthacenyl group (naphthacenyl), picenyl group (picenyl), perylenyl group (perylenyl), penta Phenyl group (pentaphenyl), hexacenyl group (hexacenyl), pentacenyl group (pentacenyl), rubicenyl group (rubicenyl), coronenyl group (coronenyl), ovalenyl group (ovalenyl), pyrrolyl group (pyrrolyl), thiophenyl group ), furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl , pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, puri Nyl group (purinyl), quinolinyl group (quinolinyl), isoquinolinyl group (isoquinolinyl), benzoquinolinyl group (benzoquinolinyl), phthalazinyl group (phthalazinyl), naphthyridinyl group (naphthyridinyl), quinoxalinyl group (quinoxalinyl), Quinazolinyl group (quinazolinyl), cinnolinyl group (cinnolinyl), carbazolyl group (c arbazolyl), phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group (benzothiophenyl), isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl ), a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and

group represented by ; and

로 표시되는 그룹; 중에서 선택되고;Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, hep Thalenyl 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, 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, iso Indolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazole Diary, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothio group phenyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzoxazolyl group, Among the triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl group At least one substituted, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, di benzofluorenyl 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, thiazolyl 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, phenane Tridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, A tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and

group represented by ; is selected from;

The Q ₃₃ to Q ₃₅ 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 car Acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorine Nyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolyl group It may be selected from a nyl group, a quinazolinyl group, and a quinoxalinyl group, but is not limited thereto.

According to another embodiment, in Formula 101, R ₁ , R ₄ and R ₇ may be each independently selected from Formulas 104-1 to 104-27; R ₂ , R ₃ , R ₅ , R ₆ , R ₈ , R ₉ , R ₁₁ and R ₁₂ are independently of each other,

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group; C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group; and

Formulas 104-1 and 104-27 below; may be selected from, but not limited to:

In Formulas 104-1 to 104-27,

Y ₃₁ is O, S, C(Z ₃₃ )(Z ₃₄ ), N(Z ₃₅ ) or Si(Z ₃₆ )(Z ₃₇ );

Z ₃₁ to Z ₃₇ 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 Acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group , chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group , is selected from a quinazolinyl group and a quinoxalinyl group;

e1 is an integer from 1 to 5;

e2 is an integer from 1 to 7;

e3 is an integer from 1 to 3;

e4 is an integer from 1 to 4;

e5 is 1 or 2;

e6 is an integer from 1 to 6;

* is a binding site with a neighboring atom.

For example, e1, e2, e3, e4, e5, and e6 in Formulas 104-1 to 104-27 may each independently be 1 or 2.

According to another embodiment, in Formula 101, R ₁ , R ₄ , and R ₇ may be each independently selected from Formulas 105-1 to 105-51;

R ₂ , R ₃ , R ₅ , R ₆ , R ₈ , R ₉ , R ₁₁ and R ₁₂ are independently of each other,

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group; C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group; and

Formulas 5-1 to 5-48 below; may be selected from, but not limited to:

In Formula 101, b1 represents the number of R ₁ , and may be an integer of 1 to 10, for example, 1 to 3. The b1 may be 1, 2, or 1. When b1 is 2 or more, two or more R ₁ may be the same as or different from each other. The description of b2 to b9 may be understood with reference to the description of b1 and Chemical Formula 101.

In Formula 101, b11 represents the number of R ₁₁ , and may be an integer of 1 to 10, for example, 1 to 3. The b11 may be 1, 2, or 1. When b11 is 2 or more, two or more R ₁₁ may be the same as or different from each other.

In Formula 101, b12 represents the number of R ₁₂ , and may be an integer of 1 to 10, for example, 1 to 3. b12 may be 1, 2, or 1. When b12 is 2 or more, two or more R ₁₂ may be the same as or different from each other.

In Formula 101, c11 represents the number of moieties represented by *-(L ₁₁ ) _a11 -(R ₂₁ ) _b11 , and is selected from an integer of 1 to 4. c11 may be 1 or 2. When c11 is 2 or more, two or more *-(L ₁₁ ) _a11 -(R ₁₁ ) _b11 are the same as or different from each other.

In Formula 101, c12 represents the number of moieties represented by *-(L ₁₂ ) _a12 -(R ₁₂ ) _b12 , and is selected from an integer of 1 to 4. c12 may be 1 or 2. When c12 is 2 or more, two or more *-(L ₁₂ ) _a12 -(R ₁₂ ) _b12 are the same as or different from each other.

According to one embodiment, in Formula 101, both c11 and c12 may be 1.

In Formula 101, *-(L ₁₁ ) _a11 -(R ₁₁ ) _b11 is bonded to at least one of 1 ^st , 2 ^nd , 3 ^rd and 4 ^th carbons of Ring A (refer to Formula 1' below), and *- (L ₁₂ ) _a12 -(R ₁₂ ) _b12 may be bonded to at least one of the 1 ^st , 2 ^nd , 3 ^rd and 4 ^th carbons of Ring B.

<Formula 101'>

According to one embodiment, in Formula 101, *-(L ₁₁ ) _a11 -(R ₁₁ ) _b11 is bonded to at least one of the 2 ^nd and 3 ^rd carbons of Ring A, and *-(L ₁₂ ) _a12 -( R ₁₂ ) _b12 may be bonded to at least one of the 2 ^nd and 3 ^rd carbons of ring B.

For example, the compound represented by Formula 101 may be represented by Formula 101A:

<Formula 101A>

For a description of each of the substituents in Formula 101A, refer to the description of Formula 101.

According to another embodiment, the compound represented by Formula 101 may be represented by Formula 101-1A, 101-2A, 101-3A, or 101A':

<Formula 101-1A>

<Formula 101-2A>

<Formula 101-3A>

<Formula 101A'>

In Formulas 101-1A, 101-2A, 101-3A, and 101A', X ₁ is C[(L ₂ ) _a2 -(R ₂ ) _b2 ][(L ₃ ) _a3 -(R ₃ ) _b3 ], Si[ (L ₂ ) _a2 -(R ₂ ) _b2 ][(L ₃ ) _a3- (R ₃ ) _b3 ], S or O, and X ₂ is C[(L ₅ ) _a5- (R ₅ ) _b5 ][( L ₆ ) _a6 -(R ₆ ) _b6 ], Si[(L ₅ ) _a5 -(R ₅ ) _b5 ][(L ₆ ) _a6 -(R ₆ ) _b6 ], S or O; X ₃ is C[(L ₈ ) _a8 -(R ₈ ) _b8 ][(L ₉ ) _a9 -(R ₉ ) _b9 ], Si[(L ₈ ) _a8 -(R ₈ ) _b8 ][(L ₉ ) _a9 -(R ₉ ) _b9 ], S or O (ie, in Formula 1A′, X ₁ is not N[(L ₁ ) _a1- (R ₁ ) _b1 ], and X ₂ is N[(L ₄ ) _a4- (R ₄ ) _b4 ], and X ₃ is not N[(L ₇ ) _a7 -(R ₇ ) _b7 ]), except that the above formulas 101A′, 101-1A, 101-2A and 101 For a description of the substituent of -3A, refer to the description of Formula 101 above. Of course, in Formula 101A', X ₁ is C[(L ₂ ) _a2 -(R ₂ ) _b2 ][(L ₃ ) _a3 -(R ₃ ) _b3 ], X ₂ is S, and X ₃ is C[ (L ₈ ) _a8 -(R ₈ ) _b8 ][(L ₉ ) _a9 -(R ₉ ) _b9 ] is excluded.

For example, at least one of R ₇ , R ₁₁ and R ₁₂ of Formula 101-1A, at least one of R ₁ , R ₁₁ and R ₁₂ of Formula 101-2A, R ₄ , R of Formula 101-3A At least one of ₁₁ and R ₁₂ and at least one of R ₁₁ and R ₁₂ in Formula 101A' are each independently a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, or a C ₃ -C ₁₀ cyclo Alkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl group oxy group, C ₆ -C ₆₀ aryl group thio group, C ₁ -C ₆₀ heteroaryl group, monovalent a non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts 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 aryl groupoxy group, C ₆ -C ₆₀ aryl group thio group, C ₁ -C C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C substituted with at least one of a ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed polycyclic group ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl groupoxy group, C ₆ -C ₆₀ aryl group thio group, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group; can be selected from

For example, at least one of R ₇ , R ₁₁ and R ₁₂ of Formula 101-1A, at least one of R ₁ , R ₁₁ and R ₁₂ of Formula 101-2A, R ₄ , R of Formula 101-3A At least one of ₁₁ and R ₁₂ and at least one of R ₁₁ and R ₁₂ in Formula 101A' are each independently selected from the group consisting of:

로 표시되는 그룹; 및pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl (oxazolyl), isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl ( indolyl), indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl (naphthyridinyl), quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl (phenanthrolinyl), phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, Isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl (dibenzothiophenyl), a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and

group represented by ; and

로 표시되는 그룹; 중에서 선택될 수 있다.Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group and naphthyl group substituted with at least one, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, iso Thiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolyl group Nyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzo imidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group , a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and

group represented by ; can be selected from

According to another example, at least one of R ₇ , R ₁₁ and R ₁₂ of Formula 101-1A, at least one of R ₁ , R ₁₁ and R ₁₂ of Formula 101-2A, and R ₄ of Formula 101-3A , at least one of R ₁₁ and R ₁₂ and at least one of R ₁₁ and R ₁₂ in Formula 101A′ are each independently selected from Formulas 104-4 to 104-27 (provided that Formulas 104-4 to 104- Y ₃₁ among 7 may be represented by one of O, S, or N(Z ₃₅ ), but is not limited thereto.

For example, the compound represented by Formula 101 may be represented by Formula 101-1A, 101-2A, 101-3A, or 101A', and selected from Formulas 101-1A, 101-2A, 101-3A or 101A'. ,

L ₁ , L ₄ , L ₇ , L ₁₁ and L ₁₂ are each independently represented by one of Formulas 12-1 to 12-37;

a1, a4, a7, a11 and a12 are each independently 0, 1 or 2;

R ₁ , R ₄ , R ₇ , R ₁₁ and R ₁₂ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group , a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group, or one of Formulas 104-1 to 104-27;

b1, b4, b7, b11 and b12 may be 1.

Here, at least one of R ₇ , R ₁₁ and R ₁₂ of Formula 101-1A, at least one of R ₁ , R ₁₁ and R ₁₂ of Formula 101-2A, R ₄ , R ₁₁ of Formula 101-3A, and At least one of R ₁₂ and at least one of R ₁₁ and R ₁₂ in Formula 101A' are each independently selected from Formulas 104-4 to 104-27 (provided that Y ₃₁ in Formulas 104-4 to 104-7) may be represented by one of O, S, or N(Z ₃₅ ), but is not limited thereto.

As another example, the condensed cyclic compound is represented by Formula 101-1A, 101-2A, 101-3A, or 101A', and in Formula 101-1A, 101-2A, 101-3A or 101A',

L ₁ , L ₄ , L ₇ , L ₁₁ and L ₁₂ are each independently represented by one of Formulas 103-1 to 103-59;

a1, a4, a7, a11 and a12 are each independently 0 or 1;

R ₁ , R ₄ , R ₇ , R ₁₁ and R ₁₂ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group , a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group, and one of Formulas 105-1 to 105-51;

b1, b4, b7, b11 and b12 may be 1.

In another embodiment, the compound represented by Chemical Formula 101 is represented by Chemical Formula 101(81), 101(70), 101(15), 101(92) or 101(106), and Chemical Formula 101(81) ), 101 (70), 101 (15), 101 (92) or 101 (106),

L ₁ , L ₄ , L ₇ to L ₉ , L ₁₁ and L ₁₂ are each independently represented by one of Formulas 12-1 to 12-37;

a1, a4, a7 to a9, a11 and a12 are each independently 0, 1 or 2;

R ₁ , R ₄ , R ₇ to R ₉ , R ₁₁ and R ₁₂ 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group, or one of Formulas 104-1 to 104-27;

b1, b4, b7 to b9, b11 and b12, c11 and c12 may be 1:

<Formula 101(81)>

<Formula 101(70)>

<Formula 101(15)>

<Formula 101(92)>

<Formula 101 (106)>

As another example, the compound represented by Chemical Formula 101 is represented by Chemical Formula 101(81), 101(70), 101(15), 101(92) and 101(106), and Chemical Formula 101(81) , of 101 (70), 101 (15), 101 (92) and 101 (106),

L ₁ , L ₄ , L ₇ to L ₉ , L ₁₁ and L ₁₂ are each independently represented by one of Formulas 103-1 to 103-59;

a1, a4, a7 to a9, a11 and a12 are each independently 0 or 1;

R ₁ , R ₄ , R ₇ to R ₉ , R ₁₁ and R ₁₂ 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group, or one of Formulas 105-1 to 105-51;

b1, b4, b7 to b9, b11 and b12, c11 and c12 may be 1, but is not limited thereto.

The compound represented by Formula 101 may be one of the following compounds (101)-1 to (101)-208, but is not limited thereto:

In Formula 101, when X ₂ is N[(L ₄ ) _a4 -(R ₄ ) _b4 ], i) X ₁ is C[(L ₂ ) _a2 -(R ₂ ) _b2 ][(L ₃ ) _a3 - (R ₃ ) _b3 ] or Si[(L ₂ ) _a2 -(R ₂ ) _b2 ][(L ₃ ) _a3 -(R ₃ ) _b3 ], and X ₃ is N[(L ₇ ) _a7 -(R ₇ ) ) _b7 ], C[(L ₈ ) _a8 -(R ₈ ) _b8 ][(L ₉ ) _a9 -(R ₉ ) _b9 ], Si[(L ₈ ) _a8 -(R ₈ ) _b8 ][(L ₉ ) ) _a9 -(R ₉ ) _b9 ], S or O, or ii) X ₁ is N[(L ₁ ) _a1- (R ₁ ) _b1 ], S or O, and X ₃ is C[(L ₈ ) _a8 -(R ₈ ) _b8 ][(L ₉ ) _a9 -(R ₉ ) _b9 ] or Si[(L ₈ ) _a8 -(R ₈ ) _b8 ][(L ₉ ) _a9 -(R ₉ ) _b9 ] . That is, in Formula 101, when X ₂ is N[(L ₄ ) _a4- (R ₄ ) _b4 ], at least one of X ₁ and X ₃ includes C or Si. Accordingly, since the compound represented by Chemical Formula 101 can introduce various substituents, it is easy to control the energy level.

On the other hand, since ring C and ring E in Formula 101 are condensed with ring D at an anti-syn position with respect to ring D (see Formula 101" below), they have an asymmetric molecular structure, and thus have low crystallinity. Therefore, it can have excellent film-forming properties.

<Formula 101">

A method for synthesizing the compound represented by Chemical Formula 101 can be easily recognized by those skilled in the art with reference to Synthesis Examples to be described later.

Formula 111

<Formula 111>

In Formula 111, Ring A ₁ and Ring A ₂ may be each independently selected from benzene, naphthalene, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, cinoline, quinazoline, quinoxaline, and naphthyridine. can be selected.

In Formula 111, Y ₁ is N-[(L ₃ ) _a3 -(R ₃ ) _b3 ], C(R ₅ )(R ₆ ), Si(R ₅ )(R ₆ ), O, S, or S(= O) can be ₂ .

In Formula 111, Y ₂ is N-[(L ₄ ) _a4- (R ₄ ) _b4 ], C(R ₇ )(R ₈ ), Si(R ₇ )(R ₈ ), O, S, or S(= O) can be ₂ .

In Formula 111, L ₁ to L ₄ are each independently selected from 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 heteroarylene group , a substituted or unsubstituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.

In Formula 111, a1 to a4 may be each independently selected from an integer of 0 to 4.

In Formula 111, R ₁ to R ₈ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydra Group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, 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 A substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl Oxy 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 Condensed monovalent non-aromatic heteropolycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ) and -B(Q ₆ )(Q ₇ ) may be selected from have.

In Formula 111, b1 to b4 may be each independently selected from an integer of 1 to 4.

In Formula 111, c1 and c2 may be each independently 1 or 2.

i) Y ₁ in Formula 111 is N-[(L ₃ ) _a3- (R ₃ ) _b3 ], C(R ₇ )(R ₈ ), Si(R ₇ )(R ₈ ), O, S, or When S(=O) ₂ , at least one of R ₁ to R ₃ is a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group including at least one nitrogen as a ring-forming atom, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, selected from a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

ii) In Formula 111, Y ₁ is C(R ₅ )(R ₆ ), Si(R ₅ )(R ₆ ), O, S, or S(=O) ₂ , and Y ₂ is N-[(L ₄ ) ) _a4- (R ₄ ) _b4 ], at least one of R ₁ , R ₂ and R ₄ is a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group including at least one nitrogen as a ring-forming atom, substituted or an unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

iii) In Formula 111, when Y ₁ is N-[(L ₃ ) _a3 -(R ₃ ) _b3 ], and Y ₂ is N-[(L ₄ ) _a4- (R ₄ ) _b4 ], R ₁ to At least one of R ₄ is a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group containing at least one nitrogen as a ring-forming atom, a substituted or unsubstituted selected from a C ₁ -C ₆₀ heteroaryl group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

When the film is formed using the compound represented by Chemical Formula 111, excellent processability can be secured, and when the compound represented by Chemical Formula 111 is employed in an organic light emitting device, the organic light emitting device can have high efficiency.

In addition, the molecular weight of the compound represented by Formula 111 may be 900 or less. When the molecular weight of the compound represented by Formula 111 is 900 or less, it is possible to secure a low deposition temperature during deposition of the compound represented by Formula 111. can be obtained

For example, the molecular weight of the compound represented by Formula 111 may be 450 to 810 level. More specifically, the molecular weight of the compound represented by Formula 111 may be in the range of 530 to 682. More specifically, the molecular weight of the compound represented by Formula 111 may be 600 or less.

In Formula 111, R ₁ to R ₈ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydra Group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C ₁ -C ₁₀ alkyl group, substituted or unsubstituted C ₁ -C ₁₀ alkoxy group, substituted or unsubstituted phenyl group , substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted bi A phenylyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perylenyl group , substituted or unsubstituted indenyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted pyrrolyl group, substituted or unsubstituted pyrazolyl group, substituted or unsubstituted imidazolyl group , substituted or unsubstituted triazolyl group, substituted or unsubstituted oxazolyl group, substituted or unsubstituted thiazolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted thiadiazolyl group, substituted or Unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted benzothiophenyl group , substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted A substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzthiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phena It may be a diyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, or a combination thereof, It is not limited thereto.

For example, R ₅ to R ₈ in Formula 111 may be each independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, and the following substituents:

In Chemical Formula 111, L ₁ and L ₂ may be selectively controlled to determine the total conjugation length of the compound, and a triplet energy bandgap may be adjusted therefrom. Through this, properties of materials required for the organic light emitting device can be realized.

In Formula 111, L ₁ and L ₂ are each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or an unsubstituted anthracenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted It may be selected from a m-terphenyl group and a substituted or unsubstituted perylenyl group.

According to one embodiment, L ₁ and L ₂ in Formula 111 may be a phenylene group. When L ₁ and L ₂ in Formula 111 are phenylene groups, both core portions based on the phenylene group may be ortho, meta, or para-bonded.

In Formula 111, Ring A ₁ and Ring A ₂ may each independently be benzene or naphthalene. When Ring A ₁ and Ring A ₂ in Formula 111 are each independently benzene or naphthalene, thermal stability of the compound represented by Formula 111 may be improved.

According to another embodiment, at least one of Ring A ₁ and Ring A ₂ in Formula 111 is pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, cinoline, quinazoline, quinoxaline, and naphthy It may be selected from ridine. When at least one of Ring A ₁ and Ring A ₂ in Formula 111 is pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, cinoline, quinazoline, quinoxaline and naphthyridine, Formula 111 The electron transport characteristics of the compound represented by , may be finely adjusted, and the efficiency of the organic light emitting device employing the compound represented by the formula 111 may be improved.

In Formula 111, Y ₁ may be N-[(L ₃ ) _a3- (R ₃ ) _b3 ] or S, and Y ₂ may be N-[(L ₄ ) _a4- (R ₄ ) _b4 ]. In Formula 111, when Y ₁ is N-[(L ₃ ) _a3 -(R ₃ ) _b3 ] or S, and Y ₂ is N-[(L ₄ ) _a4- (R ₄ ) _b4 ], Formula 111 The compound represented by may have an appropriate level of energy, so that the organic light emitting device employing the compound represented by Chemical Formula 111 may have high efficiency.

In Formula 111, Y ₁ may be N-[(L ₃ ) _a3 -(R ₃ ) _b3 ], and Y ₂ may be N-[(L ₄ ) _a4- (R ₄ ) _b4 ]. In Formula 111, Y ₁ is N-[(L ₃ ) _a3 -(R ₃ ) _b3 ], and Y ₂ is N-[(L ₄ ) _a4- (R ₄ ) _b4 ], represented by Formula 111 When the sublimation property of the compound to be used is improved, and a thin film is formed with the compound represented by Chemical Formula 111, improved processability can be secured.

In another embodiment, in Formula 111, Y ₁ is C(R ₅ )(R ₆ ) or Si(R ₅ )(R ₆ ), and Y ₂ is N-[(L ₄ ) _a4- (R ₄ ) _b4 ].

In another embodiment, in Formula 111, Y ₁ may be Si(R ₅ )(R ₆ ), and Y ₂ may be C(R ₇ )(R ₈ ).

i) Y ₁ in Formula 111 is N-[(L ₃ ) _a3- (R ₃ ) _b3 ], C(R ₇ )(R ₈ ), Si(R ₇ )(R ₈ ), O, S, or When S(=O) ₂ , at least one of R ₁ to R ₃ is, independently of each other, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, or a substituted or unsubstituted pyridinyl group , is selected from a substituted or unsubstituted pyrimidinyl group and a substituted or unsubstituted triazinyl group,

ii) In Formula 111, Y ₁ is C(R ₅ )(R ₆ ), Si(R ₅ )(R ₆ ), O, S, or S(=O) ₂ , and Y ₂ is N-[(L ₄ ) ) _a4- (R ₄ ) _b4 ], at least one of R ₁ , R ₂ and R ₄ is, independently of each other, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or selected from an unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, and a substituted or unsubstituted triazinyl group,

iii) In Formula 111, when Y ₁ is N-[(L ₃ ) _a3 -(R ₃ ) _b3 ], and Y ₂ is N-[(L ₄ ) _a4- (R ₄ ) _b4 ], R ₁ to At least one of R ₄ is, independently of each other, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, and a substituted or It may be selected from unsubstituted triazinyl groups.

According to another embodiment,

i) Y ₁ in Formula 111 is N-[(L ₃ ) _a3- (R ₃ ) _b3 ], C(R ₇ )(R ₈ ), Si(R ₇ )(R ₈ ), O, S, or When S(=O) ₂ , at least one of R ₁ to R ₃ is, independently of each other, selected from Formulas X-1 to X-15,

ii) In Formula 111, Y ₁ is C(R ₅ )(R ₆ ), Si(R ₅ )(R ₆ ), O, S, or S(=O) ₂ , and Y ₂ is N-[(L ₄ ) ) _a4- (R ₄ ) _b4 ], at least one of R ₁ , R ₂ and R ₄ is independently selected from Formulas X-1 to X-15,

iii) In Formula 111, when Y ₁ is N-[(L ₃ ) _a3 -(R ₃ ) _b3 ], and Y ₂ is N-[(L ₄ ) _a4- (R ₄ ) _b4 ], R ₁ to At least one of R ₄ may be each independently selected from Formulas (111)X-1 to (111)X-15.

[Formula (111)X-1] [Formula (111)X-2]

[Formula (111)X-3] [Formula (111)X-4]

[Formula (111)X-5] [Formula (111)X-6]

[Formula (111)X-7] [Formula (111)X-8] [Formula (111)X-9] [Formula (111)X-10]

[Formula (111)X-11] [Formula (111)X-12] [Formula (111)X-13]

[Formula (111)X-14] [Formula (111)X-15]

The compound represented by Chemical Formula 111 may be represented by one of the following Chemical Formulas 112 to 115:

<Formula 112>

<Formula 113>

<Formula 114>

<Formula 115>

Ring A ₁ , Ring A ₂ , Y ₁ , Y ₂ , L ₁ , L ₂ , a1 , a2 , R ₁ , R ₂ , b1 , b2, c1 and c2 in Formulas 112 to 115 are described in Formula 111 See the description for

As shown in Chemical Formulas 112 and 113, when R ₁ and R ₂ are bonded to the para position based on a phenylene group, the organic light emitting device employing the compound represented by Chemical Formulas 112 or 113 may have high efficiency.

As shown in Chemical Formulas 114 and 115, when R ₁ and R ₂ are bonded to the meta position based on the phenylene group, the sublimation temperature of the compound is relatively decreased to form a film using the compounds represented by Chemical Formulas 114 and 115. Fairness can be improved.

The compound represented by Formula 111 may be one of the following compounds (111)A-1 to (111)A-145, but is not limited thereto:

[(111)A-1] [(111)A-2] [(111)A-3]

[(111)A-4] [(111)A-5] [(111)A-6]

[(111)A-7] [(111)A-8] [(111)A-9]

[(111)A-10] [(111)A-11] [(111)A-12]

[(111)A-13] [(111)A-14]

[(111)A-15] [(111)A-16]

[(111)A-17] [(111)A-18]

[(111)A-19] [(111)A-20]

[(111)A-21] [(111)A-22]

[(111)A-23] [(111)A-24] [(111)A-25]

[(111)A-26] [(111)A-27] [(111)A-28]

[(111)A-29] [(111)A-30] [(111)A-31]

[(111)A-32] [(111)A-33] [(111)A-34]

[(111)A-35] [(111)A-36]

[(111)A-37] [(111)A-38]

[(111)A-39] [(111)A-40] [(111)A-41]

[(111)A-41] [(111)A-42] [(111)A-43]

[(111)A-44] [(111)A-45] [(111)A-46]

[(111)A-47] [(111)A-48] [(111)A-49]

[(111)A-50] [(111)A-51] [(111)A-52]

[(111)A-53] [(111)A-54] [(111)A-55]

[(111)A-56] [(111)A-57] [(111)A-58]

[(111)A-59] [(111)A-60] [(111)A-61]

[(111)A-62] [(111)A-63] [(111)A-64]

[(111)A-65] [(111)A-66] [(111)A-67]

[(111)A-68] [(111)A-69]

[(111)A-70] [(111)A-71]

[(111)A-72] [(111)A-73]

[(111)A-74] [(111)A-75] [(111)A-76]

[(111)A-77] [(111)A-78] [(111)A-79]

[(111)A-80] [(111)A-81]

[(111)A-82] [(111)A-83]

[(111)A-84] [(111)A-85]

[(111)A-86] [(111)A-87]

[(111)A-88] [(111)A-89]

[(111)A-90] [(111)A-91] [(111)A-92] [(111)A-93]

[(111)A-94] [(111)A-95] [(111)A-96]

[(111)A-97] [(111)A-98] [(111)A-99] [(111)A-100]

[(111)A-101] [(111)A-102] [(111)A-103]

[(111)A-104]

[(111)A-105] [(111)A-106] [(111)A-107]

[(111)A-108] [(111)A-109] [(111)A-110]

[(111)A-111] [(111)A-112] [(111)A-113] [(111)A-114]

[(111)A-115] [(111)A-116]

[(111)A-117] [(111)A-118] [(111)A-119]

[(111)A-120] [(111)A-121] [(111)A-122]

[(111)A-123] [(111)A-124]

[(111)A-125] [(111)A-126] [(111)A-127]

[(111)A-128] [(111)A-129] [(111)A-130]

[(111)A-131] [(111)A-132] [(111)A-133]

[(111)A-134] [(111)A-135] [(111)A-136]

[(111)A-137] [(111)A-138] [(111)A-139]

[(111)A-140] [(111)A-141] [(111)A-142]

[(111)A-143] [(111)A-144] [(111)A-145]

According to another embodiment, the compound represented by Formula 111 may be one of the following compounds (111)B-1 to (111)B-72, but is not limited thereto:

[(111)B-1] [(111)B-2] [(111)B-3]

[(111)B-4] [(111)B-5] [(111)B-6]

[(111)B-7] [(111)B-8] [(111)B-9]

[(111)B-10] [(111)B-11] [(111)B-12]

[(111)B-13] [(111)B-14] [(111)B-15]

[(111)B-16] [(111)B-17] [(111)B-18]

[(111)B-19] [(111)B-20] [(111)B-21]

[(111)B-22] [(111)B-23] [(111)B-24]

[(111)B-25] [(111)B-26] [(111)B-27]

[(111)B-28] [(111)B-29] [(111)B-30]

[(111)B-31] [(111)B-32] [(111)B-33]

[(111)B-34] [(111)B-35] [(111)B-36]

[(111)B-37] [(111)B-38] [(111)B-39]

[(111)B-40] [(111)B-41] [(111)B-42]

[(111)B-43] [(111)B-44] [(111)B-45]

[(111)B-46] [(111)B-47] [(111)B-48]

[(111)B-49] [(111)B-50] [(111)B-51]

[(111)B-52] [(111)B-53] [(111)B-54]

[(111)B-55] [(111)B-56] [(111)B-57]

[(111)B-58] [(111)B-59] [(111)B-60]

[(111)B-61] [(111)B-62] [(111)B-63]

[(111)B-64] [(111)B-65] [(111)B-66]

[(111)B-67] [(111)B-68] [(111)B-69]

[(111)B-70] [(111)B-71] [(111)B-72]

Formula 121

<Formula 121>

Ring A ₁ in Formula 121 is a heterocyclic group having 2 to 40 carbon atoms and having at least one nitrogen as a ring forming atom.

For example, ring A ₁ in Formula 121 may be selected from pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, cinoline, quinazoline, quinoxaline, and naphthyridine, but is not limited thereto. .

Ring A ₂ in Formula 121 may be selected from benzene, naphthalene, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, cinoline, quinazoline, quinoxaline, and naphthyridine.

In Formula 121, X ₁ is C(R ₅ )(R ₆ ), Si(R ₅ )(R ₆ ), O, S, N(R ₅ ), S(=O) ₂ , C(=O), or -P(=O) ₂ .

In Formula 121, m is selected from an integer of 0 to 2.

For example, m in Formula 121 may be 0, and -(X ₁ ) _m - in Formula 121 may be a single bond.

In Formula 121, X ₂ is N-[(L ₂ ) _a2 -Ar ₂ ], C(R ₇ )(R ₈ ), Si(R ₇ )(R ₈ ), O, S or S(=O) ₂ can be

In Formula 121, L ₁ to L ₃ 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 heteroarylene group , a substituted or unsubstituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.

For example, in Formula 121, L ₁ to L ₃ are each independently

a phenylene group, a naphthylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, and a carbazolylene 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, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a phenanthrenyl group and at least one of a biphenyl group substituted with a phenylene group, a naphthyl group a ren group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, and a carbazolylene group; may be selected from, but is not limited thereto.

In Formula 121, a1 to a3 may be each independently selected from an integer of 0 to 4.

For example, in Formula 121, a1 to a3 may be 0 or 1.

In Formula 121, Ar ₁ and Ar ₂ are each independently 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 unsubstituted It may be selected from a cyclic monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

In Formula 121, R ₁ to R ₈ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydra Group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, 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 A substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl Oxy 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 Condensed monovalent non-aromatic heteropolycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ) and -B(Q ₆ )(Q ₇ ) may be selected from have.

For example, in Formula 121, R ₁ to R ₄ may each independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, A hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group.

As another example, in Formula 121, R ₅ to R ₈ are each independently a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group can be selected from

In Formula 121, b1 to b4 are each independently selected from an integer of 1 to 3.

In the compound represented by Formula 121, a ring A ₁ condensed core having electron transport properties and a carbazole-based core are connected to each other via -(L ₃ ) _a3 -, which has excellent charge transfer properties and thermal stability. can have

According to another embodiment, Ar ₁ of Formula 121 is a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₁ - It may be selected from a C ₆₀ heteroaryl group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group. Accordingly, the compound represented by Chemical Formula 121 may have excellent electron transport properties.

According to another embodiment, in Formula 121, X ₂ is N-[(L ₂ ) _a2 -Ar ₂ ], and Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C ₆ -C ₆₀ aryl group. can Accordingly, the compound represented by Chemical Formula 121 may have a high thermal decomposition temperature, and when a film is formed with the compound represented by Chemical Formula 121, excellent processability may be secured.

For example, Ar ₁ and Ar ₂ in Formula 121 may each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted phenanthryl group , substituted or unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenylyl group, substituted or unsubstituted p-terphenyl group, substituted or unsubstituted m-terphenyl group, substituted or unsubstituted A substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted Or an unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazole a diyl, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or Unsubstituted triazinyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted quinoli Nyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted benzoxazinyl group, substituted or an unsubstituted benzthiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, and a substituted or unsubstituted phenoxazine group, However, the present invention is not limited thereto.

For example, Ar ₁ and Ar ₂ in Formula 121 may be selected from Formulas (121)W-1 to (121)W-8, but are not limited thereto:

[(121)W-1] [(121)W-2] [(121)W-3] [(121)W-4]

[(121)W-5] [(121)W-6] [(121)W-7] [(121)W-8]

In Chemical Formula 121, L ₁ to L ₃ may be selectively controlled to determine the total length of the conjugation of the compound, and the triplet energy bandgap may be adjusted therefrom.

According to one embodiment, the compound represented by Formula 121 may be represented by one of Formulas 121-1 to 121-11 below.

<Formula 121-1>

<Formula 121-2>

<Formula 121-3>

<Formula 121-4>

<Formula 121-5>

<Formula 121-6>

<Formula 121-7>

<Formula 121-8>

<Formula 121-9>

<Formula 121-10>

<Formula 121-11>

X ₁ , m, X ₂ , L ₁ , L ₃ , a1 , a3 , Ar ₁ , R ₁ , R ₂ , b1 and b2 in Formulas 121-1 to 121-11 are the same as those of Formula 121. see

For example, in Formulas 121-1 to 121-11, when X ₂ is N-[(L ₂ ) _a2 -Ar ₂ ], Ar ₁ is a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or an unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non- selected from a condensed aromatic polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, Ar ₂ is a substituted or unsubstituted C ₆ -C ₆₀ aryl group and a substituted or unsubstituted monovalent condensed non-aromatic group polycyclic groups and may be selected from

In Formulas 121-1 to 121-11, X ₁₁ is N or C(R ₁₁ ), X ₁₂ is N or C(R ₁₂ ), X ₁₃ is N or C(R ₁₃ ), and X ₁₄ is N or C(R ₁₄ ), X ₁₅ is N or C(R ₁₅ ), X ₁₆ is N or C(R ₁₆ ), and the descriptions of R ₁₁ to R ₁₆ are the descriptions of R ₃ in Formula 121, respectively. see

At least one of X ₁₁ to X ₁₄ in Formulas 121-1 and 121-2 is N. For example, one or two of X ₁₁ to X ₁₄ in Formulas 121-1 and 121-2 is N.

At least one of X ₁₁ to X ₁₆ in Formulas 121-3 to 121-11 is N. For example, one or two of X ₁₁ to X ₁₆ in Formulas 121-3 to 121-11 is N.

In Formulas 121-1 to 121-11, X ₂₁ is N or C(R ₂₁ ), X ₂₂ is N or C(R ₂₂ ), X ₂₃ is N or C(R ₂₃ ), and X ₂₄ is N or C(R ₂₄ ), X ₂₅ is N or C(R ₂₅ ), X ₂₆ is N or C(R ₂₆ ), and the descriptions of R ₂₁ to R ₂₆ are the descriptions of R ₄ in Formula 121, respectively. see

As shown in Formulas 121-1 and 121-2, when both cores are carbazole-based cores, the compounds represented by Formulas 121-1 and 121-2 may have improved thermal stability.

When a carbazole-based core in which a benzo or azobenzo ring is additionally condensed as shown in Formulas 121-3 to 121-11 is included, the triplet energy state (T1) of the compounds represented by Formulas 121-3 to 121-11 is Since it can be easily adjusted, it can be effectively applied to an organic light emitting device. In addition, since the compound represented by one of Formulas 121-1 to 121-11 has a high glass transition temperature, an organic light emitting device employing the compound may have excellent stability.

In Formulas 121 and 121-1 to 121-11, a3 may be 0, and -(L ₃ ) _a3 - may be a single bond. Accordingly, the compounds represented by Chemical Formulas 121 and 121-1 to 121-11 may have a relatively low molecular weight, and thus the sublimation temperature of the compound may be lowered to provide excellent processability. In addition, the compounds represented by Formulas 121 to 132 in which a3 is 0 can easily form intermolecular packing, and when the compounds represented by Formulas 121 and 121-1 to 121-11 in which a3 is 0 are used, a uniform film formation is possible.

For example, when X ₂ in Formulas 121-1 to 121-11 is N-[(L ₂ ) _a2 -Ar ₂ ], Ar ₁ is represented by Formulas (121)W-1 to (121)W-8 and Formulas (121)X-1 to (121)X-22, and Ar ₂ may be selected from Formulas (121)W-1 to (121)W-8.

[Formula (121)X-1] [Formula (121)X-2]

[Formula (121)X-3] [Formula (121)X-4]

[Formula (121)X-5] [Formula (121)X-6] [Formula (121)X-7]

[Formula (121)X-8] [Formula (121)X-9] [Formula (121)X-10] [Formula (121)X-11]

[Formula (121)X-12] [Formula (121)X-13] [Formula (121)X-14] [Formula (121)X-15]

[Formula (121)X-16] [Formula (121)X-17] [Formula (121)X-18] [Formula (121)X-19]

[Formula (121)X-20] [Formula (121)X-21] [Formula (121)X-22]

The compound represented by Formula 121 may be one of the following compounds (121)-1 to (121)-168, but is not limited thereto.

(121)- 1 (121)-2 (121)-3

(121)-4 (121)-5 (121)-6

(121)-7 (121)-8 (121)-9

(121)-10 (121)-11 (121)-12

(121)-13 (121)-14 (121)-15

(121)-16 (121)-17 (121)-18

(121)-19 (121)-20 (121)-21

(121)-22 (121)-23 (121)-24

(121)-25 (121)-26 (121)-27

(121)-28 (121)-29 (121)-30

(121)-31 (121)-32 (121)-33

(121)-34 (121)-35 (121)-36

(121)-37 (121)-38 (121)-39

(121)-40 (121)-41 (121)-42

(121)-43 (121)-44 (121)-45

(121)-46 (121)-47 (121)-48

(121)-49 (121)-50 (121)-51

(121)-52 (121)-53 (121)-54

(121)-55 (121)-56 (121)-57

(121)-58 (121)-59 (121)-60

(121)-61 (121)-62 (121)-63

(121)-64 (121)-65 (121)-66

(121)-67 (121)-68 (121)-69

(121)-70 (121)-71 (121)-72

(121)-73 (121)-74 (121)-75

(121)-76 (121)-77 (121)-78

(121)-79 (121)-80 (121)-81

(121)-82 (121)-83 (121)-84

(121)-85 (121)-86 (121)-87

(121)-88 (121)-89 (121)-90

(121)-91 (121)-92 (121)-93

(121)-94 (121)-95 (121)-96

(121)-97 (121)-98 (121)-99

(121)-100 (121)-101 (121)-102

(121)-103 (121)-104 (121)-105

(121)-106 (121)-107 (121)-108

(121)-109 (121)-110 (121)-111

(121)-112 (121)-113 (121)-114

(121)-115 (121)-116 (121)-117

(121)-118 (121)-119 (121)-120

(121)-121 (121)-122 (121)-123

(121)-124 (121)-125 (121)-126

(121)-127 (121)-128 (121)-129

(121)-130 (121)-131 (121)-132

(121)-133 (121)-134 (121)-135

(121)-136 (121)-137 (121)-138

(121)-139 (121)-140 (121)-141

(121)-142 (121)-143 (121)-144

(121)-145 (121)-146 (121)-147

(121)-148 (121)-149 (121)-150

(121)-151 (121)-152 (121)-153

(121)-154 (121)-155 (121)-156

(121)-157 (121)-158 (121)-159

(121)-160 (121)-161 (121)-162

(121)-163 (121)-164 (121)-165

(121)-166 (121)-167 (121)-168

Formulas 131A and 131B

<Formula 131A>

In Formula 131A, each Z is independently N or CR ^a , and at least one of Z is N;

In Formula 131A, R ¹ to R ¹⁰ and R ^a are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C ₁ -C ₁₀ alkyl group, and a substituted or unsubstituted C ₆ -C ₁₂ aryl group,

The total number of 6-membered rings substituted on the triphenylene core in Formula 131A is 6 or less,

In Formula 131A, L is selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, and a substituted or unsubstituted terphenylene group,

In Formula 131A, n1 to n3 are each independently 0 or 1,

In Formula 131A, n1+n2+n3≥1.

The 6-membered ring substituted to the triphenylene core in Formula 131A refers to all 6-membered rings directly or indirectly connected to the triphenylene core, and includes a 6-membered ring composed of a carbon atom, a nitrogen atom, or a combination thereof.

The compound represented by Formula 131A may be represented by Formula 131A-1 or 131A-2, but is not limited thereto:

<Formula 131A-1> <Formula 131A-2>

For descriptions of Z, R ¹ to R ¹⁰ , L and n1 to n3 in Formulas 131A-1 and 131A-2, refer to the description of Formula 131A.

Since at least one of the plurality of Zs in Formula 131A is N, electrons may be easily accommodated when an electric field is applied. Accordingly, an electric device employing the compound represented by Formula 131A, for example, an organic light emitting diode, may have a low driving voltage.

In addition, in Chemical Formula 131A, at least one of the plurality of Zs in Chemical Formula 131A is N, so that it can easily accommodate electrons when an electric field is applied, and also includes a triphenylene core that easily accommodates holes, so that in Chemical Formula 131A The compound represented by may have a bipolar structure. Thereby, the balance of the flow of holes and electrons in an electric device employing the compound represented by Formula 131A, for example, in an organic light emitting device can be balanced, and an organic light emitting device employing the compound represented by Formula 131A may have high efficiency.

The compound represented by Formula 131A has at least one kink structure centered on the ring included in Formula 131A.

The bent structure refers to a structure in which two connecting portions connecting the three rings do not form a linear structure with each other. For example, in the case of a phenylene group, an ortho-phenylene group (o-phenylene) and a meta-phenylene group (m-phenylene) in which the connecting portions do not form a straight structure have the above-mentioned bent structure, and the para-phenylene group (p-) in which the connecting portions form a straight structure. phenylene) does not have the above folded structure.

The bent structure in Formula 131A may be formed around a linking group (L) and/or an arylene group/heteroarylene group.

For example, when n1 of Formula 131A is 0, that is, when -(L) _n1 - is a single bond, a bent structure may be formed around an arylene group/heteroarylene group. For example, when n1 of Formula 131A is 0, that is, when -(L) _n1 - is a single bond, the compound represented by Formula 131A may be represented by Formula 131Aa or 131Ab:

<Formula 131Aa> <Formula 131Ab>

In Formulas 131Aa and 131Ab, for descriptions of Z, R ¹ to R ¹⁰ and L, refer to the description of Formula 131A.

For example, when n1 of Formula 131A is 1, a bent structure may be formed around the linking group (L) in Formula 131A. For example, L in Formula 131A may be a substituted or unsubstituted phenylene group having a bent structure, a substituted or unsubstituted biphenylene group having a bent structure, or a substituted or unsubstituted terphenylene group having a bent structure. For example, L in Formula 131A may be selected from the following group 1:

<Group 1>

In Group 1, R ¹⁵ to R ⁴² are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group , carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, 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 arylox 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 1 may be selected from a non-aromatic condensed heteropolycyclic group and -N(Q ₃₁ )(Q ₃₂ ).

Formula 131A may have at least two bent structures. For example, Chemical Formula 131A may have at least 2 to 4 bent structures.

The compound represented by 131A has a bent structure as described above, thereby appropriately localizing charges and effectively controlling the flow of the conjugated system. The organic light emitting device employing the compound represented by the formula 131A is can have a long life.

In addition, since the compound represented by Formula 131A can effectively prevent intermolecular stacking, when a film is formed using the compound represented by Formula 131A, process stability is improved and the deposition temperature can be lowered. . Such a stacking prevention effect may be further improved when n1 in Formula 131A is 1.

According to one embodiment, the compound represented by Chemical Formula 131A may be represented by one of the following Chemical Formulas 131Ac to 131At:

<Formula 131Ac> <Formula 131Ad>

<Formula 131Ae> <Formula 131Af>

<Formula 131Ag> <Formula 131Ah>

<Formula 131Ai> <Formula 131Aj>

<Formula 131Ak> <Formula 131Al>

<Formula 131Am> <Formula 131An>

<Formula 131Ao> <Formula 131Ap>

<Formula 131Aq> <Formula 131Ar>

<Formula 131As> <Formula 131At>

For the description of Z and R ¹ to R ¹⁰ in Formulas 131Ac to 131at, refer to the description of Formula 131A,

In Formulas 131Ac to 131at, R ⁶⁰ to R ⁷⁷ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, A hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, 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 It may be selected from a monovalent non-aromatic condensed heteropolycyclic group and -N(Q ₃₁ )(Q ₃₂ ).

For example, in Formulas 131Ac to 131Ah, R ¹ to R ¹⁰ and R ⁶⁰ to R ⁷⁷ are each independently selected from hydrogen, deuterium, a C ₁ -C ₁₀ alkyl group, and a phenyl group, and at least one of the plurality of Z is It may be N, but is not limited thereto.

For example, the compound represented by Formula 131A may be one of the compounds of Group 2 below, but is not limited thereto:

<Group 2>

<Formula 131B>

In Formula 131B, Y ¹ is a single bond, a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₂ -C ₂₀ alkenylene group, or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group , substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted A substituted C ₆ -C ₆₀ arylene group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic hetero condensed group selected from the polycyclic group,

Ar ¹ in Formula 131B is a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or Unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic group It is selected from a condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group,

In Formula 131B, R ¹¹ to R ¹⁴ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group , carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, 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 arylox 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 and substituted or unsubstituted 1 is selected from a non-aromatic condensed heterocyclic polycyclic group,

At least one of R ¹¹ to R ¹⁴ and Ar ¹ in Formula 131B includes a substituted or unsubstituted triphenylene group or a substituted or unsubstituted carbazole group.

The compound represented by Formula 131B may be represented by one of the following Formulas 131B-I to 131B-III:

<Formula 131B-I> <Formula 131B-II>

<Formula 131B-III>

In Formulas 131B-I to 131B-III, Y ¹ to Y ³ are each independently a single bond, a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₂ -C ₂₀ alkenylene group, or a substituted or an 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 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 divalent non-aromatic condensed polycyclic group and It is selected from a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

In Formulas 131B-I to 131B-III, Ar ¹ and Ar ² are each independently 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 selected from a group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

In Formulas 131B-I to 131B-III, R ¹¹ to R ¹⁴ and R ⁴³ to R ⁵⁴ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or A salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted a C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, A substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ - Selected from a C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group can be

The compound represented by Formula 131B-I has a structure in which two carbazole groups having a substituent are connected.

In Formula 131B-I, Ar ¹ and Ar ² are substituents having hole or electron properties, and each independently, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or Unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted fluorenyl group , substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted It may be selected from a dibenzofuranyl group and a substituted or unsubstituted dibenzothiophenyl group.

At least one of Ar ¹ and Ar ² in Formula 131B-I may be, for example, a substituent having electronic properties, and may be, for example, a substituent represented by Formula (131)A below.

[Formula (131)A]

In Formula (131)A, each Z is independently N or CR ^b ,

A1 and A2 in Formula (131)A are each independently 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 unsubstituted selected from a cyclic monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

At least one of Z, A1 and A2 in Formula (131)A contains N,

In Formula (131)A, a and b are each independently 0 or 1.

The substituent represented by Formula (131) A may be, for example, one of the substituents of Group 3 below.

[Group 3]

In addition, at least one of Ar ¹ and Ar ² in Formula 131B-I may be, for example, a substituent having hole characteristics, for example, a substituent listed in Group 4 below.

[Group 4]

For example, in Formula 131B-I,

R ¹¹ to R ¹³ and R ⁴³ to R ⁴⁴ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group , a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group and a naphthyl group,

Y ¹ and Y ² are independently of each other,

Single bond, phenylene group, naphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group, triphenylenylene group, pyrenylene group and a chrysenylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or A salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a phenyl group substituted with a phenyl group (biphenyl group), a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, phenanthree phenyl group, naphthylene group, fluorenylene group, spiro-fluorenylene group, phenyl group substituted with at least one of nyl group, anthracenyl group, fluoranthrenyl group, triphenylenyl group, pyrenyl group and chrysenyl group a renylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group and a chrysenylene group; is selected from

Ar ¹ and Ar ² are each independently,

Phenyl group, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, di Benzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, cinolinyl group, quinazolinyl group, quinoxalinyl group, imidazopyridinyl group and imidazo pyrimidinyl 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, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, Phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, carbazolyl group, benzofuranyl group, benzo Thiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, cy phenyl group, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzoflu, substituted with at least one of nolinyl group, quinazolinyl group, quinoxalinyl group, imidazopyridinyl group and imidazopyrimidinyl group Orenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, Carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, quin a nolinyl group, an isoquinolinyl group, a cinolinyl group, a quinazolinyl group, a quinoxalinyl group, an imidazopyridinyl group and an imidazopyrimidinyl group; can be selected from

According to one embodiment, in Formula 131B-I,

R ¹¹ to R ¹³ and R ⁴³ to R ⁴⁴ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group , a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group and a naphthyl group,

Y ¹ and Y ² are independently of each other,

Single bond, phenylene group, naphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group, triphenylenylene group, pyrenylene group and a chrysenylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group substituted with a phenyl group (biphenyl group), naphthyl group, fluorenyl group, spiro-fluorenyl group, phenalenyl group, phenanthree phenyl group, naphthylene group, fluorenylene group, spiro-fluorenylene group, phenyl group substituted with at least one of nyl group, anthracenyl group, fluoranthrenyl group, triphenylenyl group, pyrenyl group and chrysenyl group a renylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group and a chrysenylene group; is selected from

Ar ¹ and Ar ² are each independently,

Phenyl group, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and di benzocarbazolyl 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, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, Phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, carbazolyl group, benzofuranyl group, benzo A phenyl group, a pentalenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, benzo which is substituted with at least one of a thiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group Fluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group , a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group; may be selected from, but is not limited thereto.

According to another embodiment, in Formula 131B-I,

R ¹¹ to R ¹³ and R ⁴³ to R ⁴⁴ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group , a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group and a naphthyl group,

Y ¹ and Y ² are independently of each other,

Single bond, phenylene group, naphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group, triphenylenylene group, pyrenylene group and a chrysenylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or A salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a phenyl group substituted with a phenyl group (biphenyl group), a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, phenanthree phenyl group, naphthylene group, fluorenylene group, spiro-fluorenylene group, phenyl group substituted with at least one of nyl group, anthracenyl group, fluoranthrenyl group, triphenylenyl group, pyrenyl group and chrysenyl group a renylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, and a chrysenylene group; is selected from

Ar ¹ and Ar ² are each independently,

Phenyl group, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, di Benzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, cinolinyl group, quinazolinyl group, quinoxalinyl group, imidazopyridinyl group and imidazo pyrimidinyl 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, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, Phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, carbazolyl group, benzofuranyl group, benzo Thiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, cy phenyl group, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzoflu, substituted with at least one of nolinyl group, quinazolinyl group, quinoxalinyl group, imidazopyridinyl group and imidazopyrimidinyl group Orenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, Carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, quin a nolinyl group, an isoquinolinyl group, a cinolinyl group, a quinazolinyl group, a quinoxalinyl group, an imidazopyridinyl group and an imidazopyrimidinyl group; selected from among

At least one of Ar ¹ and Ar ² is,

a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a cinolinyl group, a quinazolinyl group, a quinoxalinyl group, an imidazopyridinyl group and an imidazopyrimidinyl 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, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, Phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, carbazolyl group, benzofuranyl group, benzo Thiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, cy A pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a quinolinyl group, an isoquinyl group substituted with at least one of a nolinyl group, a quinazolinyl group, a quinoxalinyl group, an imidazopyridinyl group and an imidazopyrimidinyl group a nolinyl group, a cinolinyl group, a quinazolinyl group, a quinoxalinyl group, an imidazopyridinyl group and an imidazopyrimidinyl group; may be selected from, but is not limited thereto.

According to another embodiment, in Formula 131B-I,

R ¹¹ to R ¹³ and R ⁴³ to R ⁴⁴ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group , a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group and a naphthyl group,

Y ¹ and Y ² are independently of each other,

Single bond, phenylene group, naphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group, triphenylenylene group, pyrenylene group and a chrysenylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or A salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a phenyl group substituted with a phenyl group (biphenyl group), a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, phenanthree phenyl group, naphthylene group, fluorenylene group, spiro-fluorenylene group, phenyl group substituted with at least one of nyl group, anthracenyl group, fluoranthrenyl group, triphenylenyl group, pyrenyl group and chrysenyl group a renylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, and a chrysenylene group; is selected from

Ar ¹ and Ar ² are each independently,

Phenyl group, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, di Benzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, cinolinyl group, quinazolinyl group, quinoxalinyl group, imidazopyridinyl group and imidazo pyrimidinyl 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, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, Phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, carbazolyl group, benzofuranyl group, benzo Thiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, cy phenyl group, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzoflu, substituted with at least one of nolinyl group, quinazolinyl group, quinoxalinyl group, imidazopyridinyl group and imidazopyrimidinyl group Orenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, Carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, quin a nolinyl group, an isoquinolinyl group, a cinolinyl group, a quinazolinyl group, a quinoxalinyl group, an imidazopyridinyl group and an imidazopyrimidinyl group; selected from among

At least one of Ar ¹ and Ar ² is,

Phenyl group, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and di benzocarbazolyl 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, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, Phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, carbazolyl group, benzofuranyl group, benzo A phenyl group, a pentalenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, benzo which is substituted with at least one of a thiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group Fluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group , a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group; can be selected from

The compound represented by Formula 131B-I may be represented by one of the following Formulas 131B-I(1) to 131B-I(4):

<Formula 131B-I(1)> <Formula 131B-I(2)>

<Formula 131B-I(3)> <Formula 131B-I(4)>

For the description of Chemical Formulas 131B-I(1) to 131B-I(4), refer to the description of Chemical Formula 131B-I.

The compound represented by Formula 131B-I may be, for example, selected from compounds listed in Group 5, but is not limited thereto.

[Group 5]

The compound represented by Formula 131B-II or 131B-III has a structure in which a substituted or unsubstituted carbazole group and a substituted or unsubstituted triphenylene group are bonded.

Ar ¹ of Formula 131B-II is a substituent having hole or electron properties, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, A substituted or unsubstituted anthracenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted A pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzothiophene group, and It may be selected from a substituted or unsubstituted dibenzofuranyl group.

The compound represented by Formula 131B-II may be, for example, selected from compounds listed in Group 6 below, but is not limited thereto.

[Group 6]

The compound represented by Formula 131B-III may be, for example, selected from compounds listed in Group 7 below, but is not limited thereto.

[Group 7]

Formula 141

<Formula 141>

In Formula 141, X ₁₁ may be selected from O and S.

In Formula 141, L ₁₁ to L ₁₄ are each independently a substituted or unsubstituted C ₁ -C ₆₀ alkylene group, a substituted or unsubstituted C ₂ -C ₆₀ alkenylene group, or a substituted or unsubstituted C ₃ - C ₁₀ cycloalkylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl selected from a ene group, a substituted or unsubstituted C ₆ -C ₆₀ arylene group, and a substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group;

said substituted C ₁ -C ₆₀ alkylene group, substituted C ₂ -C ₆₀ alkenylene group, substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ - At least one substituent of the C ₁₀ cycloalkenylene group, the substituted C ₁ -C ₁₀ heterocycloalkenylene group, the substituted C ₆ -C ₆₀ arylene group and the substituted C ₁ -C ₆₀ heteroarylene 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 ) and -B(Q ₁₆ )(Q ₁₇ ), C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, substituted with at least one , 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 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 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 group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, _monovalent non-aromatic condensed polycyclic group and monovalent ratio -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;

The 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 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 It may be selected from a -C ₆₀ 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 141, L ₁₁ to L ₁₄ are each independently a phenylene group, a naphthylene group, a phenanthrenylene group, an anthracenylene group, and a triphenylenyl group. Triphenylenylene, pyrenylene, chrysenylene, perylenylene, pyrrolylene, imidazolylene, pyridinylene, pyra pyrazinylene, pyrimidinylene, indolylene, quinolinylene, isoquinolinylene, benzoquinolinylene, quinoxalinyl Ren group (quinoxalinylene), quinazolinylene group (quinazolinylene), phenanthridinylene group (phenanthridinylene), acridinylene group (acridinylene), phenanthrolinylene group (phenanthrolinylene), phenazinylene group, furanylene group (furanylene) , benzofuranylene, thiophenylene, benzothiophenylene, triazolylene, imidazopyridinylene and imidazopyrimidinylene ; 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, C ₆ -C ₂₀ aryl group, phenyl group-substituted phenyl group, C ₁ -C ₂₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group , a phenylene group, a naphthylene group, a phenanthrenylene group, an anthracenylene group, triphenylenyl, which is substituted with at least one of a monovalent non-aromatic condensed heteropolycyclic group and -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) Ren group, pyrenylene group, chrysenylene group, perylenylene group, pyrrolylene group, imidazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, indolylene group, quinolinylene group, isoquinolinyl group Ren group, benzoquinolinylene group, quinoxalinylene group, quinazolinylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, furanylene group, benzofuranylene group, thiophenylene group, a benzothiophenylene group, a triazolylene group, an imidazopyridinylene group, and an imidazopyrimidinylene group; is selected from

Q ₃₃ to Q ₃₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazole Diary, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group phthalazinyl group, quinoxalinyl group , but may be selected from a cinolinyl group and a quinazolinyl group, but is not limited thereto.

As another example, in Formula 141, L ₁₁ to L ₁₄ may each independently represent any one of Formulas 142-1 to 142-28, but are not limited thereto:

In Formulas 142-1 to 142-28,

X ₂₁ is selected from O and S;

R ₂₁ to R ₂₃ 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 Acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, phenyl group-substituted phenyl group, naphthyl group, anthracenyl group, triphenylenyl group , pyrenyl group, phenanthrenyl group, fluorenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, and -Si(Q ₃₃ )(Q ₃₄ )(Q ₄₅ );

wherein Q ₃₃ to Q ₄₅ are each independently hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carba Zolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group phthalazinyl group, quinoxali group selected from a nyl group, a cinolinyl group, and a quinazolinyl group;

a21 is selected from 1, 2, 3 and 4;

a22 is selected from 1, 2, 3, 4, 5 and 6;

a23 is selected from 1, 2, 3, 4, 5, 6, 7 and 8;

a24 is selected from 1, 2 and 3;

a25 is selected from 1, 2, 3, 4 and 5;

a26 is selected from 1 and 2;

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

As another example, in Formula 141, L ₁₁ to L ₁₄ may each independently represent a phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, a triazinylene group, a quinazolinylene group, a quinolinylene group, and isoquinolinylene 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, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, and a phenanthrenyl group substituted with at least one of a phenylene group , naphthylene group, pyridinylene group, pyrimidinylene group, triazinylene group, quinazolinylene group, quinolinylene group and isoquinolinylene group; may be selected from, but is not limited thereto.

As another example, in Formula 141, L ₁₁ to L ₁₄ may be each independently selected from Formulas 143-1 to 143-14, but are not limited thereto:

In Formulas 143-1 to 143-14,

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

In Formula 141, a11 represents the number of L ₁₁ , and may be selected from 0, 1, 2, 3, 4, and 5. For example, in Formula 1, a11 may be selected from 0, 1, and 2, but is not limited thereto. When a11 is 0, L ₁₁ is a single bond. When a11 is 2 or more, two or more L ₁₁ may be the same as or different from each other. The description of a12 to a15 may be understood with reference to the description of a11 and the structure of Formula 141.

For example, in Formula 141, a12 to a15 may be each independently selected from 0, 1, and 2, but is not limited thereto.

As another example, in Formula 141, a11 to a13 may be each independently selected from 0 and 1, but are not limited thereto.

As another example, in Formula 141, a14 may be 0, but is not limited thereto.

In Formula 141, R ₁₁ to R ₁₃ are each independently R _ET , hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, 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 an unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocyclo Alkyl 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 monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ) and -B(Q ₆ )(Q ₇ ) ) is selected from;

At least one of R ₁₁ to R ₁₃ is R _ET ;

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 monovalent non-aromatic condensed polycyclic group At least one substituent 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 ) and -B(Q ₁₆ )(Q ₁₇ ), C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, substituted with at least one , 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 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 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 group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, _monovalent non-aromatic condensed polycyclic group and monovalent ratio -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;

The 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 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 It may be selected from a -C ₆₀ 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 the description of R _ET , see below. .

For example, in Formula 141, R ₁₁ to R ₁₃ are each independently R _ET , hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ Alkoxy group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C ₁ -C ₂₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and substituted and unsubstituted 1 is selected from a non-aromatic condensed heteropolycyclic group;

At least one of R ₁₁ to R ₁₃ may be R _ET , but is not limited thereto.

As another example, in Formula 141, R ₁₁ to R ₁₃ are each independently R _ET , 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of salts thereof;

nanthridinyl), acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazole Isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl , dibenzofuranyl group (dibenzofuranyl), dibenzothiophenyl group (dibenzothiophenyl), benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, pyridobenzofuranyl group, pyrimidobenzofura a nyl group, a pyridobenzothiophenyl group and a pyrimidobenzothiophenyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, C ₁ -C ₂₀ alkyl group-substituted phenyl group, phenyl group-substituted 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, fluorante Nyl 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, isobenzoxazolyl group , triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl 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, an acenaphthyl group, a flu Orenyl 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 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, pyridi Nyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridi Nyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazole Diary, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group , imidazopyridinyl group, imidazopyrimidinyl group, pyridobenzofuranyl group, pyrimidobenzofuranyl group, pyridobenzothiophenyl group and pyrimidobenzothiophenyl group; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ); is selected from;

The Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ are each independently, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, flu Orenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinyl group selected from a nolinyl group, a quinazolinyl group and a quinoxalinyl group;

At least one of R ₁₁ to R ₁₃ may be R _ET , but is not limited thereto.

As another example, in Formula 141, R ₁₁ to R ₁₃ are each independently R _ET , hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, or an amino group , amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of salts thereof; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ); is selected from;

The Q ₃ to Q ₅ are each independently, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, chrysenyl group , carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group and a quinoxalinyl group,

At least one of R ₁₁ to R ₁₃ may be R _ET , but is not limited thereto.

In Formula 141, b11 represents the number of R ₁₁ , and may be selected from 1, 2, 3, and 4. When b11 is 2 or more, two or more R ₁₁ may be the same as or different from each other. The description of b12 to b13 may be understood with reference to the description of b11 and the structure of Formula 141.

In Formula 1, b12 to b13 may be each independently selected from 1, 2, 3, and 4.

In Formula 141, R _ET may be selected from Formulas 149-1 to 149-52 below:

In Formulas 149-1 to 149-52,

X ₉₁ is selected from O and S;

R ₉₁ and R ₉₂ 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 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 ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group and C ₁ -C ₆₀ heteroaryl group;

a91 is selected from 1, 2, 3 and 4;

a92 is selected from 1, 2 and 3;

a93 is selected from 1 and 2;

a94 is selected from 1, 2, 3, 4, 5 and 6;

a95 is selected from 1, 2, 3, 4 and 5;

* is a binding site with a neighboring atom.

For example, in Formula 141, at least one of R ₁₁ to R ₁₃ may be R _ET , and R _ET may be selected from Formulas 149-1 to 149-52, but is not limited thereto.

For example, in Formulas 149-1 to 149-52,

X ₉₁ is selected from O and S;

R ₉₁ and R ₉₂ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, nitro group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, non a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group and a quinazolinyl group;

a91 is selected from 1, 2, 3 and 4;

a92 is selected from 1, 2 and 3;

a93 is selected from 1 and 2;

a94 is selected from 1, 2, 3, 4, 5 and 6;

a95 is selected from 1, 2, 3, 4 and 5;

* is a binding site with a neighboring atom.

As another example, in Formula 141, at least one of R ₁₁ to R ₁₃ may be R _ET , and R _ET may be selected from Formulas 141-4 to 141-8, 141-51 and 141-52, It is not limited to:

For example, in Formulas 141-4 to 141-8, 141-51 and 141-52,

X ₉₁ is selected from O and S;

R ₉₁ and R ₉₂ are each independently hydrogen, deuterium, F, -Cl, -Br, -I, cyano group, nitro group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group , naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group and quinazolinyl group;

a91 is selected from 1, 2, 3 and 4;

a92 is selected from 1, 2 and 3;

a93 is selected from 1 and 2;

* is a binding site with a neighboring atom.

As another example, in Formula 101, at least one of R ₁₁ to R ₁₃ may be R _ET , and R _ET may be selected from the following Formulas 145-1 to 145-7, but is not limited thereto:

In Formulas 145-1 to 145-7,

* is a binding site with a neighboring atom.

In another embodiment, the compound represented by Formula 141 may be represented by any one of Formulas 141-1 to 141-3 below:

<Compound 141-1>

<Compound 141-2>

<Compound 141-3>

In Formulas 141-1 to 141-3, X ₁₁ , L ₁₁ to L ₁₄ , a11 to a14 , R ₁₁ to R ₁₃ , and b11 to b13 are the same as those described for Formula 141 and ;

R ₁₁ in Formula 141-1, R ₁₂ in Formula 141-2, and R ₁₃ in Formula 141-3 are R _ET .

For example, in Formulas 141-1 to 141-3,

X ₁₁ is selected from O and S;

L ₁₁ to L ₁₄ are each independently any one of Formulas 142-1 to 142-28;

a11 to a14 are each independently selected from 0 and 1;

_{R 11} to R ₁₅ are each independently , carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of its salts; and

-Si(Q ₃ )(Q ₄ )(Q ₅ ); is selected from;

Wherein Q ₃ To Q ₅ are each independently, C ₁ -C ₂₀ Alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, chrysenyl group , carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group and a quinoxalinyl group,

At least one of R ₁₁ to R ₁₃ is R _ET ;

b11 to b13 are each independently selected from 1, 2, 3 and 4;

R _ET may be selected from Formulas 149-1 to 149-52, but is not limited thereto.

In another embodiment, the compound represented by Formula 141 may be represented by any one of Formulas 141-1A, 141-2A, and 141-3A:

<Compound 141-1A>

<Compound 141-2A>

<Compound 141-3A>

In Formulas 141-1A, 141-2A, and 141-3A, X ₁₁ , L ₁₁ to L ₁₃ , a11 to a13, R ₁₁ to R ₁₃ and b11 to b13 refer to the description of Formula 141,

R ₁₁ in Formula 141-1A, R ₁₂ in Formula 141-2A, and R ₁₃ in Formula 141-3A are each independently R _ET .

In another embodiment, the compound represented by Chemical Formula 141 may be represented by the following Chemical Formula 141-1B:

<Formula 141-1B>

In Formula 141-1B,

X ₁₁ , L ₁₁ and a11 refer to the description for Formula 141,

R _ET may be selected from Formulas 145-1 to 145-7.

The compound represented by Formula 141 may be one of the following compounds (141)-1 to (141)-20, but is not limited thereto:

According to one embodiment, the second material may include a compound represented by Formula 21A(1).

According to another embodiment, the second material may include the compound represented by Formula 31A.

According to another embodiment, the second material may include the compound represented by Formula 141-1A.

According to another embodiment, the second material may include a compound represented by Chemical Formula 61-1.

According to another embodiment, the second material may include a compound represented by one of Chemical Formulas 131Ac to 131Ah.

According to another embodiment, the second material,

i) a compound represented by one of Formulas 21A to 21C, 31A, 31B, 61, 131A, and 141, and

ii) a compound represented by one of Formulas 91A to 91D and 131B.

According to another embodiment, the second material is

i) a compound represented by one of Formula 21A(1) 31A, 61-1, 131Ac to 131Ah, and 141-1A; and

ii) a compound represented by one of Formulas 91B(1) and 131B.

According to another embodiment, both the first material and the second material may be included in the emission layer of the organic layer 15 of the organic light emitting device 10 .

According to another embodiment, both the first material and the second material are included in the emission layer of the organic layer 15 of the organic light emitting device 10 , the first material is a dopant, and the second material is a host. can Here, the content of the first material may be less than the content of the second material.

According to another embodiment, the first material and the second material are included in the light emitting layer,

The first material is a dopant, the second material is a host,

The host may include a compound represented by one of Formulas 21A to 21C, 31A, 31B, 61, 131A, and 141.

According to another embodiment, the first material and the second material are included in the light emitting layer,

The first material is a dopant, the second material is a host,

The host includes a first host and a second host,

The first host includes a compound represented by one of Formulas 21A to 21C, 31A, 31B, 61, 131A and 141,

The second host may include a compound represented by one of Formulas 91A to 91D and 131B, but is not limited thereto.

The weight ratio of the first host and the second host may be selected from the range of 1:9 to 9:1, for example, 3:7 to 7:3. For example, the weight ratio of the first host to the second host may be selected from the range of 4:6 to 6:4, but is not limited thereto. According to one embodiment, the weight ratio of the first host to the second host may be 5:5.

The organic layer 15 may further include a hole transport region and an electron transport region in addition to the light emitting layer as described above.

For example, the first electrode 11 is an anode, the second electrode 19 is a cathode, and the organic layer 15 is i) interposed between the first electrode and the light emitting layer, and a hole injection layer , a hole transport region comprising at least one of a hole transport layer and an electron blocking layer; 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.

In the present specification, the term “organic layer” refers to a single and/or a plurality of layers interposed between the first electrode 11 and the second electrode 19 among organic light emitting devices. The "organic layer" may include not only an organic compound, but also an organometallic complex including a metal.

The organic layer 15 may include a hole transport region; an emission layer; and an electron transport region.

The hole transport region may be disposed between the first electrode 11 and the emission layer.

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

The hole transport region may include only a hole injection layer or only a hole transport layer. Alternatively, the hole transport region may have a structure of a hole injection layer/hole transport layer or a hole injection layer/hole transport layer/electron blocking layer sequentially stacked from the first electrode 11 .

When the hole transport region includes the hole injection layer, the hole injection layer (HIL) may be formed on the first electrode 11 by using various methods such as vacuum deposition, spin coating, casting, LB, and the like. have.

In the case of forming the hole injection layer by the vacuum deposition method, the deposition conditions vary depending on the compound used as the hole injection layer material, the structure and thermal characteristics of the target hole injection layer, etc., but for example, the deposition temperature of about 100 to about 500° C., a vacuum degree of about 10 ⁻⁸ to about 10 ⁻³ torr, and a deposition rate of about 0.01 to about 100 Å/sec may be selected, but not limited thereto.

In the case of forming the hole injection layer by the spin coating method, the coating conditions vary depending on the compound used as the hole injection layer material, the structure and thermal properties of the desired hole injection layer, but a coating speed of about 2000 rpm to about 5000 rpm, The heat treatment temperature for removing the solvent after coating may be selected from a temperature range of about 80° C. to 200° C., but is not limited thereto.

For the conditions for forming the hole transport layer and the electron blocking layer, refer to the conditions for forming the hole injection layer.

The hole transport region is, for example, m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-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/camphorsulfonic acid), PANI/PSS (Polyaniline)/Poly(4-styrenesulfonate):polyaniline)/poly(4-styrenesulfonate)), a compound represented by the following formula 201 and a compound represented by the following formula 202 It may include at least one:

<Formula 201>

<Formula 202>

In Formula 201, Ar ₁₀₁ and Ar ₁₀₂ are each independently

Phenylene group, pentarenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluoranthenyl a lene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, and a pentacenylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts 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 ₃ -C ₁₀ cycloalkenyl group , C ₁ -C ₁₀ heterocycloalkyl 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 A phenylene group, a pentarenylene group, an indenylene group, a naphthylene group, an azulenylene group, heptal substituted with at least one of a 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed polycyclic group. Renylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylenylene group, naphthacenylene group, p a cenylene group, a perylenylene group, and a pentacenylene group; can be selected from

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

In Formulas 201 and 202, R ₁₀₁ to R ₁₀₈ , R ₁₁₁ to R ₁₁₉ and R ₁₂₁ to R ₁₂₄ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, Phosphoric acid or a salt thereof, a C ₁ -C ₁₀ alkyl group (eg, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, etc.) and a C ₁ -C ₁₀ alkoxy group (eg, a methoxy group, an ethoxy group) period, propoxy group, butoxy group, pentoxy group, etc.);

deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group, substituted with one or more salts thereof;

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

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or salts thereof, a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group and a pyrenyl group, substituted with one or more of a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group; may be selected from, but is not limited thereto.

In Formula 201, R ₁₀₉ is a phenyl group, a naphthyl group, an anthracenyl group and a pyridinyl group; and deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid Or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group and a pyridinyl group ; can be selected from

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

<Formula 201A>

For a detailed description of R ₁₀₁ , R ₁₁₁ , R ₁₁₂ and R ₁₀₉ in Formula 201A, refer to the above description.

For example, 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, a satisfactory level of 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 a cyano group-containing compound such as the following compound HT-D1, but is not limited thereto.

<Compound HT-D1> <F4-TCNQ>

The hole transport region may further include a buffer layer.

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

The emission layer EML may be formed on the hole transport region by using a method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. In the case of forming the light emitting layer by vacuum deposition or spin coating, the deposition conditions and coating conditions vary depending on the compound used, but in general, they may be selected from within the same range of conditions as those for forming the hole injection layer.

Meanwhile, when the hole transport region includes an electron blocking layer, the electron blocking layer material may be selected from materials that can be used for the hole transport region as described above and a host material to be described later, but is not limited thereto. . For example, when the hole transport region includes an electron blocking layer, mCP, which will be described later, may be used as the electron blocking layer material.

The emission layer may include a host and a dopant, and the dopant may include an organometallic compound represented by Formula 1 above. The host may be selected from one of Formulas 11, 21A to 21C, 31A, 31B, 41, 51A, 51B, 61, 71-1 to 71-12, 81, 91A to 91D, 101, 111, 121, 131A, 131B and 141. It may include at least one of the indicated compounds.

When the organic light emitting device is a full color organic light emitting device, the light emitting layer may be patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer. Alternatively, the light emitting layer may have a structure in which a red light emitting layer, a green light emitting layer, and/or a blue light emitting layer are stacked, and thus various modifications such as emitting white light are possible.

When the emission layer includes a host and a dopant, the content of the dopant may be generally selected from about 0.01 to about 15 parts by weight based on about 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-described range, excellent light emitting characteristics may be exhibited without a substantial increase in driving voltage.

Next, an electron transport region is disposed on the light emitting layer.

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

For example, the electron transport region may have a structure of a hole blocking layer/electron transport layer/electron injection layer or an electron transport layer/electron injection layer, but is not limited thereto. The electron transport layer may have a single layer or a multilayer structure including two or more different materials.

For the conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer in the electron transport region, refer to the formation conditions of the hole injection layer.

When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP, Bphen, and Balq, 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 layer may further include at least one of BCP, Bphen, and Alq ₃ , Balq, TAZ, and NTAZ.

Alternatively, the electron transport layer may include a compound represented by the following Chemical Formula 440 or 441:

<Formula 440>

<Formula 441>

In Formulas 440 and 441, L ₄₁ and L ₄₂ are each independently

C ₆ -C ₆₀ arylene group, C ₁ -C ₆₀ heteroarylene group, divalent non-aromatic condensed polycyclic group and divalent 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 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, naphthyl group, fluorenyl group, pyrenyl group, chrysenyl group, phenanthrenyl group, pyridinyl group, pyrimidinyl group and triazinyl group a C ₆ -C ₆₀ arylene group, a C ₁ -C ₆₀ heteroarylene group, a divalent non-aromatic condensed polycyclic group and a divalent non-aromatic condensed polycyclic group, substituted with at least one of the groups; is selected from

In Formulas 440 and 441, a41 and a42 are each independently selected from an integer of 0 to 5;

In Formulas 440 and 441, Ar ₄₁ and Ar ₄₂ are each independently

C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and 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 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, naphthyl group, fluorenyl group, pyrenyl group, chrysenyl group, phenanthrenyl group, pyridinyl group, pyrimidinyl group and triazinyl group a C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed polycyclic group, substituted with at least one of the groups; is selected from

In Formulas 440 and 441, R ₄₁ and R ₄₂ are each independently

Benzoimidazolyl group, benzoxazolyl group, benzothiazolyl group, benzopyrimidinyl group, imidazopyridinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group , a phenyl group, a naphthyl group, a pyrenyl group, a chrysenyl group, a fluorenyl group and a phenanthrenyl 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, benzoimidazolyl group, benzooxazolyl group, benzothiazolyl group, benzopyrimidinyl group, imidazopyridinyl group, quinolinyl group, iso A benzoimidazolyl group substituted with at least one of a quinolinyl group, a quinazolinyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a phenyl group, a naphthyl group, a pyrenyl group, a chrysenyl group, a fluorenyl group, and a phenanthrenyl group , benzoxazolyl group, benzothiazolyl group, benzopyrimidinyl group, imidazopyridinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, phenyl group, naph a tyl group, a pyrenyl group, a chrysenyl group, a fluorenyl group and a phenanthrenyl group; is selected from

For a detailed description of L ₄₁ and L ₄₂ in Formulas 440 and 441, refer to the description of L ₂ in the present specification.

Alternatively, the electron transport layer may include a compound represented by the following Chemical Formula 442:

<Formula 442>

In Formula 42, T ₁ is N or C(R ₂₀₁ ), T ₂ is N or C(R ₂₀₂ ), and T ₃ is N or C(R ₂₀₃ ), but at least one of T ₁ to T ₃ is N ego,

In Formulas 440 and 441, R ₂₀₁ to R ₂₀₃ are each independently

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or a salt thereof, 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 C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent ratio -Aromatic heterocondensed polycyclic 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, naphthyl group, fluorenyl group, pyrenyl group, chrysenyl group, phenanthrenyl group, pyridinyl group, pyrimidinyl group and triazinyl group a C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed polycyclic group, substituted with at least one of the groups; is selected from

Ar ₂₀₁ to Ar ₂₀₃ in Formulas 440 and 441 are each independently

C ₆ -C ₆₀ arylene group, C ₁ -C ₆₀ heteroarylene group, divalent non-aromatic condensed polycyclic group and divalent 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 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, naphthyl group, fluorenyl group, pyrenyl group, chrysenyl group, phenanthrenyl group, pyridinyl group, pyrimidinyl group and triazinyl group a C ₆ -C ₆₀ arylene group, a C ₁ -C ₆₀ heteroarylene group, a divalent non-aromatic condensed polycyclic group and a divalent non-aromatic condensed polycyclic group, substituted with at least one of the groups; is selected from

In Formulas 440 and 441, p, q and r are each independently 0, 1, or 2;

Ar ₂₁₁ and Ar ₂₁₃ in Formulas 440 and 441 are each independently

C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and 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 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, naphthyl group, fluorenyl group, pyrenyl group, chrysenyl group, phenanthrenyl group, pyridinyl group, pyrimidinyl group and triazinyl group a C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed polycyclic group, substituted with at least one of the groups; is selected from

According to one embodiment, at least two of T ₁ to T ₃ in Formula 442 may be N.

According to another embodiment, all of T ₁ to T ₃ in Formula 442 may be N.

In Formula 442, Ar ₂₀₁ to Ar ₂₀₃ are each independently

a phenylene group, a naphthylene group, an anthrylene group, a pyrenylene group, a fluorenylene group, a triphenylenyl group, a pyridinylene group, and a pyrimidinylene group; and

A phenyl group, a naphthyl group, an anthryl group, a pyrenyl group, a fluorenyl group, a triphenylenyl group, a pyridinyl group, and a pyrimidinyl group substituted with at least one, a phenylene group, a naphthylene group, an anthrylene group, a pyrenylene group, a fluorenylene group, a triphenylenyl group, a pyridinylene group and a pyrimidinylene group; may be selected from, but is not limited thereto.

In Formula 442, p, q, and r may each independently be 0, 1, or 2. For example, in Formula 442, p, q, and r may each independently be 0 or 1, but is not limited thereto.

Ar ₂₁₁ to Ar ₂₁₃ in Formula 442 are each independently

Phenyl group, naphthyl group, pyrenyl group, chrysenyl group, fluorenyl group, phenanthrenyl group, benzoimidazolyl group, benzoxazolyl group, benzothiazolyl group, benzopyrimidinyl group, imidazopyrimidinyl group, quinolinyl group , isoquinolinyl group, quinazolinyl group, pyridinyl group, pyrimidinyl group, pyrazinyl 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 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, naphthyl group, fluorenyl group, pyrenyl group, chrysenyl group, phenanthrenyl group, pyridinyl group, pyrimidinyl group and triazinyl group substituted with at least one of the groups, a phenyl group, a naphthyl group, a pyrenyl group, a chrysenyl group, a fluorenyl group, a phenanthrenyl group, a benzoimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzopyrimidinyl group, an imidazo a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group and a triazinyl group; may be selected from, but is not limited thereto.

According to one embodiment, at least one of Ar ₂₁₁ to Ar ₂₁₃ in Formula 442 is each independently selected from the group consisting of:

Benzoimidazolyl group, benzooxazolyl group, benzothiazolyl group, benzopyrimidinyl group, imidazopyrimidinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, pyridinyl group, pyrimidinyl group, pyrazinyl 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 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, naphthyl group, fluorenyl group, pyrenyl group, chrysenyl group, phenanthrenyl group, pyridinyl group, pyrimidinyl group and triazinyl group substituted with at least one of the groups, a benzoimidazolyl group, a benzooxazolyl group, a benzothiazolyl group, a benzopyrimidinyl group, an imidazopyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group and a triazinyl group; may be selected from, but is not limited thereto.

According to another embodiment, at least one of Ar ₂₁₁ to Ar ₂₁₃ in Formula 442 may be a substituted or unsubstituted phenanthrenyl group.

For example, the electron transport region may include at least one of the following compounds ET1 to ET16, but is not limited thereto:

<Compound ET1> <Compound ET2>

<Compound ET3> <Compound ET4>

<Compound ET5> <Compound ET6>

<Compound ET7> <Compound ET8>

<Compound ET8> <Compound ET10>

<Compound ET11> <Compound ET12>

<Compound ET13> <Compound ET14>

<Compound ET15> <Compound ET16>

According to an embodiment, the electron transport region may include an electron transport layer, and the electron transport layer may include a compound represented by at least one of Chemical Formulas 440, 441, and 442, but is not limited thereto.

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.

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

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

The electron injection layer may have a thickness of about 1 Å to about 100 Å, or 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.

A second electrode 19 is provided on the organic layer 15 . The second electrode 19 may be a cathode. As the material for the second electrode 19 , a metal, an alloy, an electrically conductive compound, and a combination thereof having a relatively low work function may be used. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. It can be used as a material for forming the second electrode 19 . Alternatively, various modifications are possible, such as forming the transmissive second electrode 19 using ITO or IZO in order to obtain a top light emitting device.

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 include a methyl group, an ethyl group, a propyl group, an isobutyl group, a 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, isopropyloxy group and the like.

In the present specification, the C ₂ -C ₆₀ alkenyl value has a structure 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. do. 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 has a structure including at least one carbon triple bond in the middle or at the terminal of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethynyl group, a propynyl group (propynyl) , etc. are included. 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 means a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cyclohep group. til groups, and the like. In the present specification, the C ₃ -C ₁₀ cycloalkylene group refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkyl 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 a 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, a 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 group 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 present specification, the C ₆ -C ₆₀ aryl group means a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the C ₆ -C ₆₀ arylene group is a carbo group having 6 to 60 carbon atoms. 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, a chrysenyl group, and the like. 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, a 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.

In the present specification, the C ₆ -C ₆₀ aryloxy group refers to -OA ₁₀₂ (here, A ₁₀₂ is the C ₆ -C ₆₀ aryl group), and the C ₆ -C ₆₀ arylthio group is -SA ₁₀₃ (here , 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 (eg, having 8 to 60 carbon atoms). Specific examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group and the like. In the present specification, the divalent non-aromatic condensed polycyclic group 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 (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 (eg, having 1 to 60 carbon atoms) in which the entire molecule has non-aromaticity. The monovalent non-aromatic condensed heteropolycyclic group includes a carbazolyl group 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, the substituted nitrogen-containing electron transporting moiety, substituted phenylene group, substituted biphenylene group, substituted terphenylene group, substituted triphenylene group, substituted carbazolyl group, substituted C ₃ -C ₁₀ cyclo alkylene 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 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 at least one of the substituents of the C ₁ -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed polycyclic group,

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkyl a nyl group and a C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cyclo Alkyl 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 ) C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C substituted with at least one of )(Q ₁₄ )(Q ₁₅ ) and -B(Q ₁₆ )(Q ₁₇ ) 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, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkyl nyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy 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, a C ₃ -C ₁₀ cycloalkyl group substituted with at least one of —N(Q ₂₁ )(Q ₂₂ ), —Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and —B(Q ₂₆ )(Q ₂₇ ), 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 an 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

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

The Q ₁ to Q ₉ , Q ₁₁ to Q ₁₇ , Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are each independently,

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

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts 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 1 substituted with at least one of a C 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 a group oxy group, a C ₆ -C ₆₀ aryl group thio 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, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts 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 aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C substituted with at least one of a ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed polycyclic group 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, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group; is selected from

Hereinafter, a compound and an organic light emitting device according to an embodiment of the present invention will be described in more detail with reference to Synthesis Examples and Examples, but the present invention is not limited to the following Synthesis Examples and Examples. In the following Synthesis Example, in the expression "'B' was used instead of 'A'", the amount of 'B' and the amount of 'A' used were the same on a molar equivalent basis.

[Example]

Synthesis Example 1: Synthesis of compound 2

Synthesis of compound 2-A

2,5-dibromopyridine (12 g, 51.0 mmol), phenylboronic acid (7.0 g, 61.0 mmol), Pd(OAc) ₂ (1.10 g, 2.5 mmol) , PPh ₃ (2.6 g, 5.0 mmol) and K ₂ CO ₃ (14.0 g, 127 mmol) was mixed with 400 mL of acetonitrile and 200 mL of methanol, and then stirred at 50 ° C. for 18 hours, Cool to room temperature and filter. From this, the organic layer was extracted using methylene chloride (methylenechloride (MC)), anhydrous magnesium sulfate (MgSO ₄ ) was added to remove moisture, and then the filtrate obtained by filtration was pressure-reduced to ethylacetate (EA): Hexane = 8.3 g (70%) of Compound 2-A was obtained by purification through column chromatography under the condition of 1:20.

Synthesis of compound 2-B

120 mL of diethyl ether was added to compound 2-A (14.2 g, 61 mmol)

2-A 14.2 g (60.6 mmol) was dissolved in diethyl ether, cooled to -78 °C, n-BuLi (39.4 mL, 67 mmol) was slowly added, and then stirred at -78 °C for 1 hour. Thereafter, TMSCl (8.74 mL, 79 mmol) was added, and the reaction proceeded at -78° C. for 1 hour, followed by heating to room temperature to proceed with the reaction for 12 hours. The organic layer obtained therefrom was extracted using MC, anhydrous magnesium sulfate was added to remove moisture, and the filtrate obtained by filtration was subjected to column chromatography with respect to the residue obtained under reduced pressure under EA:Hexane = 20:1 condition. was carried out to obtain 10.7 g (78%) of compound 2-B.

Synthesis of compound 2-C

Compound 2-B (5.9 g, 26.0 mmol) and iridium chloride (4.1 g, 12.0 mmol) were mixed with 100 mL of ethoxyethanol and 30 mL of distilled water, and then stirred under reflux for 24 hours to proceed with the reaction , and lowered the temperature to room temperature. The resulting solid was separated by filtration, washed sufficiently in the order of water/methanol/hexane, and the obtained solid was dried in a vacuum oven to obtain 6.0 g (76%) of Compound 2-C.

Synthesis of compound 2-D

Compound 2-C (6 g, 49 mmol) was mixed with 60 mL of MC, and then AgOTf (2.69 g, 10 mmol) was dissolved in 20 mL of methanol and added. After that, the reaction proceeds by stirring at room temperature for 18 hours in a state of blocking light with aluminum foil, and then filtering the celite to remove the resulting solid and reducing the filtrate to a solid obtained (Compound 2-D (6.2 g, 82%) was used in the next reaction without further purification.

Synthesis of compound 2

Compound 2-D (6.2 g, 7 mmol) and compound 2-B (1.91 g, 8.4 mmol) were mixed with 90 mL of ethanol, and the mixture was stirred under reflux for 18 hours, followed by lowering the temperature. The obtained mixture was filtered, and the obtained solid was sufficiently washed with ethanol and hexane, and column chromatography was performed under MC: hexane=35:65 to obtain 1.95 g (32%) of Compound 2. The material was identified through mass and HPLC analysis.

HRMS(MALDI) calcd for C ₄₂ H ₄₈ IrN ₃ Si ₃ : m/z 871.28, Found: 871.1823

Synthesis Example 11: Synthesis of compound (11)-2

Synthesis of intermediate (11)-A

In a 1L round-bottom flask, 3-amino-2-methoxydibenzofuran (11.1 g, 52 mmol) was dissolved in Et ₂ O (130 mL), and then BF ₃ ㅇEt ₂ O (26.4 mL, 208 mmol) was added at -20°C under 5 It was added dropwise slowly over a minute. To the resulting mixture, a mixture of tert -Butyl nitrile (21.7 mL, 64 mL) in Et ₂ O (64 mL) was slowly added for 30 minutes, stirred for 30 minutes, and then Et ₂ O (300 mL) After adding, stirred for 10 minutes under 0 ℃. After concentrating the reaction product obtained therefrom, a solution of NaI (9.4 g, 62.4 mmol) and I ₂ (1.2 g, 4.7 mmol) in dry CH ₃ CN (340 mL) was slowly added dropwise at room temperature and stirred for 1 hour. Then, 20% aqueous solution Na ₂ S ₂ O ₃ (200 mL) was added and stirred, and then the organic layer obtained by adding chloroform (300 mL X 3) was dried using MgSO ₄ , and the residue obtained by evaporating the solvent was placed on silica gel. Separation and purification by column chromatography gave intermediate (11)-A (12.1 g, yield 72%). The resulting compound was confirmed by LC-MS.

LC-MS ( m/z ) = C ₁₃ H ₁₁ NO ₂ (M ⁺ ) 213.

Synthesis of intermediate (11)-B

Intermediate (11)-A (8.92 g, 27.5 mmol), carbazole (5.06 g, 30.3 mmol), CuI (0.52 g, 2.75 mmol), K ₃ PO ₄ (8.76 g, 41.3 mmol), (ㅁ)-trans - After mixing 1,2-cyclohexanediamine (74 g L, 0.07 mmol) with 1,4-dioxane (140 mL), the temperature was raised to 110° C. under nitrogen and stirred under reflux for 48 hours, then cooled to room temperature, It was extracted with 200 mL of water and 200 mL of methylene chloride. The obtained organic layer was dried over MgSO ₄ , and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain an intermediate (11)-B (3.5 g, 35%). The resulting compound was confirmed by LC-MS.

LC-MS ( m/z ) = C ₂₅ H ₁₇ NO ₂ (M ⁺ ) 363.

Synthesis of intermediate (11)-C

Intermediate (11)-B (3.64 g, 10.0 mmol) was dissolved in methylene chloride (100 mL) under nitrogen condition in a mixture of boron tribromide (15.0 mL, 15.0 mmol; 1.0 M in dichloromethane) at 0 ° C. for 10 minutes. It was slowly added dropwise and stirred at 0° C. for 10 hours. Then, 30 mL of water was added to the mixture under a temperature of 0° C. and stirred, and the organic layer obtained by adding methylene chloride (60 mL X 3) was dried using MgSO ₄ , and the solvent was evaporated to obtain an intermediate (11)-C. did.

Synthesis of intermediate (11)-D

Intermediate (11)-C and triethylamine (12.8 mL, 91.6 mmol) were mixed in methylene chloride (100 mL) under nitrogen condition, and then trifruoromethansulfonic anhydride (5.14 mL, 30.5 mmol) was slowly added dropwise under a temperature of 0 ° C, 7 hours while stirring at a temperature of 0 °C. Then, 15 mL of 1.0 M aqueous HCl was added to the mixture under a temperature of 0° C. and stirred, and the organic layer obtained by adding methylene chloride (60 mL X 3) was dried using MgSO ₄ , and the residue obtained by evaporating the solvent was placed on silica gel. Separation and purification by column chromatography gave intermediate (11)-D (3.2 g, 65%). The resulting compound was confirmed by LC-MS.

LC-MS ( m/z ) = C ₂₅ H ₁₄ F ₃ NO ₄ S (M ⁺ ) 481.

Synthesis of compound (11)-2

Intermediate (11)-D (7.0 g, 14.5 mmol), 2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine (6.31 g, 14.5 mmol), Pd(Pph ₃ ) ₄ (0.84 g, 0.725 mmol), K ₂ CO ₃ (5.01 g, 36.3 mmol) was mixed with 50 mL of THF and 25 mL of distilled water The mixed mixture was heated to 80° C. and stirred under reflux for 18 hours. The resulting mixture was cooled to room temperature, the resulting solid was filtered, and the obtained solid was dissolved in toluene, dried over MgSO ₄ , the solvent was removed, and the obtained residue was recrystallized from Toluene:MeO to compound (11) -2 (6.25 g, 67%) was obtained. The resulting compound was confirmed by LC-MS.

LC-MS ( m/z ) = C ₄₅ H ₂₈ N ₄ O (M ⁺ ) 640.

Synthesis Example 12: Synthesis of compound (11)-3

Instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine, 4,6- Except that diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (6.17 g, 14.5 mmol) was used, Compound (11)-3 (8.5 g, 91%) was obtained by using the same method as for the synthesis of compound (11)-2 of Synthesis Example 11. The resulting compound was confirmed by LC-MS.

LC-MS ( m/z ) = C ₄₅ H ₂₈ N ₄ O (M ⁺ ) 639.

Synthesis Example 13: Synthesis of compound 27

Intermediate (11)-D (7.88 g, 16.4 mmol), 9-(quinolin-5-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- A mixture of 9H-carbazole (8.95 g, 21.3 mmol), Pd(Pph ₃ ) ₄ (0.94 g, 0.82 mmol), K ₂ CO ₃ (5.66 g, 40.9 mmol) with 100 mL of THF and 50 mL of distilled water was mixed with 80 The temperature was raised to ℃ and stirred for 18 hours under reflux. After cooling the mixture obtained therefrom to room temperature, 100 mL of distilled water was added to the mixture, stirred, and the organic layer obtained by adding methylene chloride (150 mL X 3) was dried using MgSO ₄ and the solvent was removed. Separation and purification by silica gel column chromatography gave compound (11)-27 (7.57 g, 74 %). The resulting compound was confirmed by LC-MS.

LC-MS ( m/z ) = C ₄₅ H ₂₈ N ₄ O (M ⁺ ) 625.

Synthesis Example 21: Synthesis of compound (21)-3

Synthesis of intermediate (21)3-5

Intermediate (21)3-6 (10g, 59.8mmol) and Intermediate (21)-A (8.44g, 59.8mmol) were dissolved in 200mL of DMSO, and Cs ₂ CO ₃ (23.4g, 71.8mmol) was added to the solution for 15 hours. stirred for a while. After adding 500 mL of water to the reaction mixture, the solid obtained by filtration was collected, dissolved in 300 mL of methylene chloride, and extracted by adding 300 mL of water. The organic layer obtained therefrom was dried using MgSO ₄ , and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain an intermediate (21)3-5 (12.93 g, yield 75%). The resulting compound was confirmed by LC-MS.

C ₁₈ H ₁₂ N ₂ O ₂ : M+ 288.09

Synthesis of intermediate (21)3-4

Intermediate (21)3-5 (10g, 34.7mmol) SnCl ₂ o 2H ₂ O (25.16g, 111mmol) was added to EtOH and stirred for 8 hours or more while heating to 70 ℃. When the reaction was completed, after cooling to room temperature, the reaction product was concentrated, and the organic layer obtained by adding 300 mL of methylene chloride and 300 mL of NaHCO ₃ (aq) was dried using MgSO ₄ and the residue obtained by evaporating the solvent. Water was separated and purified by silica gel column chromatography to obtain an intermediate (21)3-4 (6.27 g, yield 70%). The resulting compound was confirmed by LC-MS.

C ₁₈ H ₁₄ N ₂ : M+ 258.12

Synthesis of intermediate (21)3-3

Intermediate (21)3-4 (6g, 23.23mmol), acetic acid (acetic acid) 60mL, conc H ₂ SO ₄ 5mL was added, immersed in an ice bath (ice bath), and cooled to 10 ℃. Then, a solution of NaNO ₂ (1.6 g, 1eq) in 150 mL of water was added dropwise over 20 min and stirred for 10 min. Then, the temperature of the mixture was raised to 130° C. and stirred for 20 min. After completion of the reaction, it was cooled to room temperature, 300 mL of water was poured, and the precipitated solid was obtained by filtration. The residue was separated and purified by silica gel column chromatography to obtain an intermediate (21)3-3 (4.03 g, 72%). The resulting compound was confirmed by LC-MS.

C ₁₈ H ₁₁ N : M+ 241.09

Synthesis of intermediate (21)3-2

Intermediate (21)3-3 (3g, 12.43mmol) and NBS (2.21g, 12.43mmol) were dissolved in 100 mL of methylene chloride and stirred at room temperature for 15 hours. After completion of the reaction, the reaction was cooled to room temperature, 200 mL of methylene chloride was poured, 200 mL of water was added dropwise, and the obtained organic layer was dried over MgSO ₄ , and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography. Thus, intermediate (21)3-2 (2.03 g, 51%) was obtained. The resulting compound was confirmed by LC-MS.

C ₁₈ H ₁₀ BrN: M+ 319.00

Synthesis of intermediate (21)3-1

Intermediate (21)3-2 (1.5 g, 4.68 mmol), Intermediate B (1.19 g, 5.62 mmol), Pd(PPh ₃ ) ₄ (0.27 g, 0.234 mmol), K ₂ CO ₃ (3.24 g, 23.4 mmol) was mixed with 100 mL of THF and 30 mL of distilled water. The temperature was raised to 120 °C and stirred for 24 hours under reflux, the mixture was cooled to room temperature, and extracted with 200 mL of water and 200 mL of methylene chloride. The obtained organic layer was dried over MgSO ₄ , and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain an intermediate (21)3-1 (1.5 g, 79%). The resulting compound was confirmed by LC-MS.

C ₃₀ H ₁₈ N ₂ : M+ 406.15

Synthesis of compound (21)-3

Intermediate (21)3-1 (1g, 2.46mmol) is dissolved in 30mL of DMF, then sodium hydride is added and stirred for 1 hour. Intermediate C (0.8 g, 2.95 mmol) was dissolved in 10 mL of DMF, put into the reaction solution, and stirred at room temperature for 12 hours. The resulting precipitate was washed with methylene chloride, put in dichlorobenzene, heated, cooled to room temperature, recrystallized and separated to obtain compound (21)-3 (1.14 g, 65%). The resulting compound was confirmed by LC-MS and NMR.

C ₅₁ H ₃₁ N ₅ : M+ 713.26

1H NMR (CDCl3, 300MHz) δ(ppm) 8.36-8.19(m, 11H), 7.89(s, 1H), 7.68-7.50(m, 16H), 7.20(m, 3H)

Synthesis Example 22: Synthesis of compound (21)-2

Compound (21)-2 (68%) was used in the same manner as in Synthesis Example 21, except that Intermediate (21)-D was used instead of Intermediate (21)-C during the synthesis of Compound (21)-3. ) was synthesized. The resulting compound was confirmed by LC-MS and NMR.

C ₄₅ H ₂₇ N ₅ : M+ 637.75

1H NMR (CDCl3, 300MHz) δ(ppm) 7.36-8.30(m, 5H), 8.19-8.13(m, 4H), 7.89(s, 1H), 7.65-7.50(m, 14H), 7.20(m, 3H) )

Synthesis Example 23: Synthesis of compound (21)-4

Compound (21)-4 (70% by using the same method as in Synthesis Example 21 above, except that Intermediate (21)-E was used instead of Intermediate (21)-C during the synthesis of Compound (21)-3. ) was synthesized. The resulting compound was confirmed by LC-MS and NMR.

C ₄₆ H ₂₈ N4 : M+ 636.23

1H NMR (CDCl3, 300MHz) δ(ppm) 8.9(s, 1H), 8.30-8.13(m, 5H), 7.94-7.89(m, 5H), 7.65-7.50(m, 14H), 7.20(m, 3H) )

Synthesis Example 24: Synthesis of compound (21)-7

Compound (21)-7 (62%) using the same method as in Synthesis Example 21, except that Intermediate (21)-F was used instead of Intermediate (21)-C during the synthesis of Compound (21)-3. ) was synthesized. The resulting compound was confirmed by LC-MS and NMR.

C ₄₄ H ₂₆ N ₄ : M+ 610.22

1H NMR (CDCl3, 300MHz) δ(ppm) 8.30-8.13(m, 6H), 7.89-7.80(m, 5H), 7.65-7.50(m, 12H), 7.20(m, 3H)

Synthesis Example 25: Synthesis of compound (21)-8

Compound (21)-8 (62%) using the same method as in Synthesis Example 21, except that Intermediate (21)-G was used instead of Intermediate (21)-C during the synthesis of Compound (21)-3. ) was synthesized. The resulting compound was confirmed by LC-MS and NMR.

C ₅₀ H ₃₀ N ₄ : M+ 686.25

1H NMR (CDCl3, 300MHz) δ(ppm) 8.30-8.13(m, 8H), 7.89-7.75(m, 7H), 7.65-7.41(m, 12H), 7.20(m, 3H)

Synthesis Example 26: Synthesis of compound (21)-76

Synthesis of intermediate (21)76-1

Intermediate (21) of Synthesis Example 21 above, except that Intermediate (21)76-2 and Intermediate (21)76-3 were used instead of Intermediate (21)3-2 and Intermediate (21)-B, respectively. Intermediate (21)76-1 was synthesized using the same method as in the synthesis method of 3-1.

Synthesis of compound (21)-76

The compound of Synthesis Example 21, except that Intermediate (21)76-1 and Intermediate (21)-D were respectively used instead of Intermediate (21)3-1 and Intermediate (21)-C in synthesizing Compound 23 Compound (21)-76 (yield of 74%) was synthesized using the same method as that of (21)-3. The resulting compound was confirmed by LC-MS and NMR.

C ₄₅ H ₂₇ N ₅ : M+ 686.25

1H NMR (CDCl3, 300MHz) δ(ppm) 8.62(d, 1H), 8.36(m, 4H), 8.22-8.19(m, 4H), 7.74(s, 1H), 7.65-7.50(m, 14H), 7.20 (m, 3H)

Synthesis Example 27: Synthesis of compound (21)-60

Synthesis of intermediate (21)60-2

Intermediate (21) using the same method as for the synthesis of Intermediate (21)3-2 of Synthesis Example 21, except that Intermediate (21)60-3 was used instead of Intermediate (21)3-3 60-2 was synthesized.

Synthesis of intermediate (21)60-1

Intermediate (21)3 of Synthesis Example 21 above, except that Intermediate (21)60-2 and Intermediate (21)-H were used instead of Intermediate (21)3-2 and Intermediate (21)-B, respectively. Intermediate (21)60-1 was synthesized using the same method as for -1 synthesis.

Synthesis of compound (21)-60

Compound (21)- of Synthesis Example 21 above, except that Intermediate (21)60-1 and Intermediate (21)-I were used instead of Intermediate (21)3-1 and Intermediate (21)-C, respectively. Compound (21)-60 (yield of 51%) was synthesized using the same method as in the synthesis method of 3.

C ₃₈ H ₂₂ N ₄ : M+ 534.18

1H NMR (CDCl3, 300MHz) δ(ppm) 8.87(d, 1H), 8.51-8.01(m, 8H), 7.89(s, 1H), 7.70-7.43(m, 8H), 7.20-7.15(m, 4H) )

Synthesis Example 31: Synthesis of compound (31)-1

Synthesis of Intermediate (31)A

3-iodo-4-nitro-1,1'-biphenyl (3-iodo-4-nitro-1,1'-biphenyl) (20.1 g, 61.8 mmol), (2-bromophenyl) in a 2-neck flask ) Boronic acid ((2-bromophenyl) boronic acid) (18.6 g, 92.7 mmol), triphenylphosphine (PPh _3, 2.4 g, 9.2 mmol), tetrakis (triphenylphosphine) palladium (0) (Tetrakis(triphenylphosphine)palladium(0)) (Pd(PPh ₃ ) ₄ , 0.7 g, 3.1 mmol) and potassium carbonate (K ₂ CO ₃ ,17.1 g, 123.7 mmol) were added, toluene 800 ml and H ₂ O 80 ml After adding, argon substitution was performed and refluxed for 12 hours. Thereafter, the organic layer was cooled to room temperature and extracted with ethyl acetate (Ethyl Acetate, EA) to remove moisture using magnesium sulfate (MgSO ₄ ), then concentrated and column chromatography (hexane/EA = 10/1)) to obtain 47 g of intermediate (31)A (yield = 75%).

¹ H NMR (CDCl ₃ , 300 MHz): 8.22 (d, 1H), 7.78 (dd, 1H), 7.70 to 7.64 (m, 3H), 7.56 (d, 1H), 7.52 to 7.39 (m, 4H), 7.33 ~7.26 (m, 2H).

Synthesis of Intermediate (31)B

Intermediate (31)A (25.8 g, 72.9 mmol) and PPh ₃ (57.4 g, 218.8 mmol) were placed in a 1-neck flask, 80 ml of 1,2-dichlorobenzene (DCB) was added, followed by argon substitution for 12 hours was stirred at 150 °C. DCB was distilled off, cooled to room temperature, dissolved in a small amount of toluene, and purified by column chromatography (Hexane) to obtain 15 g of intermediate (31)B (yield = 64%).

¹ H NMR (CDCl ₃ , 300 MHz): 8.99 (s, 1H), 8.20 (b, 1H), 7.75-7.72 (m, 3H), 7.51-7.46 (m, 3H), 7.43-7.27 (m, 4H) .

Synthesis of intermediate (31)C

Intermediate (31)B (32.0g, 99.3 mmol), Cu (0.63g, 9.9 mmole) and K ₂ CO ₃ (27.1 g, 198.6 mmol) were put in a two-neck flask, and 320 ml of dimethylformamide (DMF) was added. , argon was substituted, and iodobenzene (22.5ml, 198.6 mmol) was added. Thereafter, after refluxing for 12 hours, cooling to room temperature, and extracting with EA to remove moisture using MgSO ₄ from the obtained organic layer, and then concentration, column chromatography (Hexane) was performed to perform column chromatography (Hexane), and 25 g of intermediate C as a white solid (yield = 64%) was obtained. Intermediate (31)C was identified through 1H-NMR and LC/MS (liquid chromatography mass spectrometry).

1H NMR (CDCl3, 300MHz): 9.07 (d, 1H), 7.75~7.71 (m, 3H), 7.69~7.61 (m, 2H), 7.55~7.40 (m, 7H), 7.37~7.31 (m, 2H) , 7.26~7.22 (dd, 1H)

LC/MS, calculated: C ₂₄ H ₁₆ BrN = 398.29, found: m/z = 398.1 (M+, 100 %)

Synthesis of intermediate (31)D

Intermediate (31)C (33 g, 83 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3, 2-dioxaborolane) (25 g, 100 mmol), potassium acetate (KOAc, 21 g, 210 mmol) and 1,1'-Bis(diphenylphosphino)ferrocene-palladium( II )dichloride (PdCl2(dppf)2, 3.4g, 4.2 mmol) was added to THF (200 mL), followed by stirring at 70° C. for 24 hours. After completion of the reaction, the reaction solution was extracted with water and EA, and water was removed from the organic layer obtained by using MgSO ₄ , concentrated, and purified by column chromatography (methylene chloride/n-hexane=3/2, silica gel). Intermediate (31)D was obtained as a white solid (26 g, yield=60%).

¹ H NMR (CDCl ₃ , 300 MHz): 9.52 (s, 1H), 7.79~7.32 (m, 15H), 1.50 (s, 12H).

Synthesis of compound (31)-1

Intermediate (31)D (13.3 g, 30 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (7.3 g, 27 mmol), K ₂ CO ₃ (11 g, 81 mmol) and After adding Pd(PPh ₃ ) ₄ (1.5 g, 1.3 mmol) to toluene (50 mL), the mixture was stirred at 120° C. for 24 hours. After completion of the reaction, water was added, stirred, and filtered. A dark gray solid obtained by filtration was dissolved in hot toluene and filtered. The obtained toluene solution was precipitated using methanol, and the solid obtained by filtration was recrystallized from 1-chlorobenzene to obtain compound (31)-1 as yellow crystals (11.0 g, yield = 73%). The structure of the obtained compound (31)-1 was confirmed through LC/MS.

LC/MS, calculated: C39H26N4 = 550.65, found: m/z = 550.2 (M+, 100 %)

Synthesis Example 32: Synthesis of compound (31)-2

2-chloro-4,6-diphenylpyri instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Compound (31)-2 (yellow crystals) using the same method as the synthesis method of compound (31)-1 of Synthesis Example 31, except that midine (2-chloro-4,6-diphenylpyrimidine) was used , yield = 67%) was synthesized. The synthesized compound (31)-2 was confirmed through LC/MS.

LC/MS, calculated: C ₄₀ H ₂₇ N ₃ = 549.66, found: m/z = 549.2 (M+, 100 %)

Synthesis Example 33: Synthesis of compound (31)-3

Intermediate (31)C (17.5 g, 42 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)- 1,3,5-triazine (20.0 g, 46 mmol), K ₂ CO ₃ (14 g, 104 mmol) and Pd(PPh ₃ ) ₄ (2.4 g, 2.1 mmol) were placed in toluene (80 mL), Stirred at 120° C. for 48 hours. After completion of the reaction, water was added, stirred, and filtered. A dark gray solid obtained by filtration was dissolved in hot toluene and filtered. The obtained toluene solution was precipitated using methanol, filtered, and the obtained solid was recrystallized from 1-chlorobenzene to obtain compound (31)-3 as a white powder (18.0 g, yield = 70%). The synthesized compound (31)-3 was confirmed through 1H-NMR and LC/MS.

¹ H NMR (CDCl ₃ , 300 MHz): 9.17 (s, 1H), 8.92 (d, 1H), 8.77 (dd, 4H), 7.95-7.68 (m, 7H), 7.66-7.40 (m, 14H), 7.27 ~7.19 (m, 3H).

LC/MS, calculated: C ₄₅ H ₃₀ N ₄ = 626.75, found: m/z = 626.2 (M+, 100 %)

Synthesis Example 34: Synthesis of compound (31)-18

2-(3'-bromo-[1, instead of 2-chloro-4,6-diphenyl-1,3,5-triazine) Except that 1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used, the same method as the synthesis method of compound (31)-1 of Synthesis Example 31 After the synthesis was carried out using , the obtained solid was recrystallized from 1-chlorobenzene to obtain compound (31)-18 as a white solid (yield = 76%). The synthesized compound (31)-18 was confirmed through LC/MS.

LC/MS, calculated: C ₅₁ H ₃₄ N ₄ = 702.84, found: m/z = 702.2 (M+, 100 %)

Synthesis Example 35: Synthesis of compound (31)-32

Synthesis of Intermediate (31)E

(2-bromophenyl) boronic acid instead of 3-bromo (1,1'-biphenyl) -4-boronic acid ((3-bromo- [1,1'-biphenyl) ]-4-yl) boronic acid) using the same method as the synthesis method of Intermediate (31)A of Synthesis Example 31, except that Intermediate (31)E (white solid, yield = 66) %) was synthesized. The synthesized intermediate (31)E was identified through LC/MS.

LC/MS, calculated: C ₂₄ H ₁₆ BrNO ₂ = 430.29, found: m/z = 429.04 (M+, 100 %)

Synthesis of intermediate (31)F

Intermediate F (white solid, yield = 57%) using the same method as for the synthesis of Intermediate (31)B of Synthesis Example 31, except that Intermediate (31)E was used instead of Intermediate (31)A ) was synthesized. The synthesized intermediate F was confirmed through LC/MS.

LC/MS, calculated: C ₂₄ H ₁₆ BrN = 398.29, found: m/z = 397.05 (M+, 100 %)

Synthesis of intermediate (31)G

Intermediate (31)G (white solid, yield) using the same method as for the synthesis of Intermediate (31)C of Synthesis Example 31, except that Intermediate (31)F was used instead of Intermediate (31)B. = 61%) was synthesized. The synthesized intermediate (31)G was identified through LC/MS.

LC/MS, calculated: C ₃₀ H ₂₀ BrN = 474.39 found: m/z = 475.08 (M+, 100 %)

Synthesis of compound (31)-32

The synthesis was carried out using the same method as for the synthesis of compound (31)-3 of Synthesis Example 33, except that Intermediate (31)G was used instead of Intermediate (31)C, and the obtained The solid was recrystallized from 1-chlorobenzene to synthesize compound (31)-32 (white solid, yield = 70%). The synthesized compound (31)-32 was confirmed through LC/MS.

LC/MS, calculated: C ₅₁ H ₃₄ N ₄ = 702.84 found: m/z = 702.28 (M+, 100 %)

Synthesis Example 36: Synthesis of compound (31)-36

Synthesis of intermediate (31)H

Except that 2-bromotriphenylene was used instead of iodobenzene, the intermediate (31)C of Synthesis Example 31 was synthesized using the same method as the synthesis method 31)H (white solid, yield = 50%) was synthesized. The synthesized intermediate (31)H was identified through LC/MS.

LC/MS, calculated: C ₃₆ H ₂₂ BrN = 548.47 found: m/z = 547.09 (M+, 100 %)

Synthesis of compound (31)-36

The synthesis was carried out using the same method as for the synthesis of compound (31)-3 of Synthesis Example 33, except that Intermediate (31)H was used instead of Intermediate (31)C, and the obtained The solid was recrystallized from 1,2-dichlorobenzene to synthesize compound (31)-36 (white solid, yield = 52%). The synthesized compound (31)-36 was confirmed through LC/MS.

LC/MS, calculated: C ₅₇ H ₃₆ N ₄ = 776.92 found: m/z = 776.29 (M+, 100 %)

Synthesis Example 37: Synthesis of compound (31)-39

Synthesis of intermediate (31)I

3-iodo-4-nitro-1,1'-biphenyl (3-iodo-4-nitro-1,1'-biphenyl) instead of 2- (3-iodo-4-nitrophenyl) -triphenylene Except that (2-(3-iodo-4-nitrophenyl)triphenylene) was used, intermediate (31)I (yellow solid, yield = 54 %) was synthesized. The synthesized intermediate (31)L was confirmed through LC/MS.

LC/MS, calculated: C ₃₀ H ₁₈ BrNO ₂ = 504.37, found: m/z = 503.05 (M+, 100 %)

Synthesis of intermediate (31)J

Intermediate (31)J (white solid, yield) using the same method as for the synthesis of Intermediate (31)B of Synthesis Example 31, except that Intermediate (31)I was used instead of Intermediate (31)A = 48%) was synthesized. The synthesized intermediate (31)J was identified through LC/MS.

LC/MS, calculated: C ₃₀ H ₁₈ BrN = 472.37, found: m/z = 471.06 (M+, 100 %)

Synthesis of intermediate (31)K

Intermediate (31)K (white solid, yield) using the same method as for the synthesis of Intermediate (31)C of Synthesis Example 31, except that Intermediate (31)J was used instead of Intermediate (31)B. = 45%) was synthesized. The synthesized intermediate (31)K was confirmed through LC/MS.

LC/MS, calculated: C ₃₆ H ₂₂ BrN = 548.47 found: m/z = 547.09 (M+, 100 %)

Synthesis of compound (31)-39

The synthesis was carried out using the same method as for the synthesis of compound (31)-3 of Synthesis Example 33, except that Intermediate (31)K was used instead of Intermediate (31)C, and the obtained The solid was recrystallized from 1,2-dichlorobenzene to synthesize compound (31)-39 (white solid, yield = 63%). The synthesized compound (31)-39 was confirmed through LC/MS.

LC/MS, calculated: C ₅₇ H ₃₆ N ₄ = 779.92, found: m/z = 776.29 (M+, 100 %)

Synthesis Example 38: Synthesis of compound (31)-96

Synthesis of intermediate (31)L

9-(3-iodo-4-nitrophenyl)-9H-carba instead of 3-iodo-4-nitro-1,1'-biphenyl (3-iodo-4-nitro-1,1'-biphenyl) Except that the sol (9- (3-iodo-4-nitrophenyl) -9H-carbazole) was used, the intermediate (31) using the same method as the synthesis method of the intermediate (31) A of Synthesis Example 31 )L (white solid, yield = 60%) was synthesized. The synthesized intermediate (31)L was confirmed through LC/MS.

LC/MS, calculated: C ₂₄ H ₁₅ N ₂ O ₂ = 443.29, found: m/z = 442.0 (M+, 100 %)

Synthesis of intermediate (31)M

Intermediate (31)M (white solid, yield) using the same method as for the synthesis of Intermediate (31)B of Synthesis Example 31, except that Intermediate (31)L was used instead of Intermediate (31)A = 55%) was synthesized. The synthesized intermediate (31)M was identified through LC/MS.

LC/MS, calculated: C ₂₄ H ₁₅ BrN ₂ = 411.29, found: m/z = 410.0 (M+, 100 %)

Synthesis of intermediate (31)N

Intermediate (31)N (white solid, yield) using the same method as for the synthesis of Intermediate (31)C of Synthesis Example 31, except that Intermediate (31)M was used instead of Intermediate (31)B. = 62%) was synthesized. The synthesized intermediate (31)N was identified through LC/MS.

LC/MS, calculated: C ₃₀ H ₁₉ BrN ₂ = 487.39 found: m/z = 486.0 (M+, 100 %)

Synthesis of compound (31)-96

The synthesis was carried out using the same method as for the synthesis of compound (31)-3 of Synthesis Example 33, except that Intermediate (31)N was used instead of Intermediate (31)C, and the obtained The solid was recrystallized from N-methyl-2-pyrrolidone (NMP, n-methyl-2-pyrrolidone) to synthesize compound (31)-96 (white solid, yield = 68%). The synthesized compound (31)-96 was confirmed through LC/MS.

LC/MS, calculated: C ₅₁ H ₃₃ N ₅ = 715.84, found: m/z = 715.2 (M+, 100 %)

Synthesis Example 41: Synthesis of compound (41)-1

Synthesis of intermediate (41)A(1) (benzo-1H-thieno[3,2-d]pyrimidine-2,4-dione)

In a 2000 mL round flask, a mixture of benzo-methyl 3-amino-2-thiophenecarboxylate (47.5 g, 0.23 mol) and urea (79.4 g, 1.15 mol) was stirred at 200° C. for 2 hours. After cooling the hot reaction mixture to room temperature, it was poured into sodium hydroxide solution, impurities were removed by filtration, and the reaction product was acidified (HCl, 2N), and the obtained precipitate was dried to obtain an intermediate (41)A(1). (35 g, 75%).

Synthesis of intermediate (41)A(2)(benzo-2,4-dichloro-thieno[3,2-d]pyrimidine)

Intermediate (41)A(1)(benzo-1H-thieno[3,2-d]pyrimidine-2,4-dione) (35 g, 0.16 mol) and phosphorus oxychloride (600 mL) in a 1000 mL round flask The mixture was stirred under reflux for 6 hours. The reaction mixture was cooled to room temperature and poured into ice/water with vigorous stirring to form a precipitate. The resulting reaction product was filtered to give the intermediate (41)A(2)(benzo-2,4-dichloro-thieno[3,2-d]pyrimidine) (35 g, 85%, white solid). .

Synthesis of Intermediate (41)A

In a 1000 mL flask, 20.0 g (78.4 mmol) of intermediate (41)A(2), 11.0 g (90.15 mmol) of phenylboronic acid, 27.09 g (195.99 mmol) of potassium carbonate Pd(PPh ₃ ) ₄ (Tetrakis- (triphenylphosphine)? 4.53 g (3.9 mmol) of palladium(0)) was added to 300 mL of 1,4-dioxane and 150 mL of water, and then heated to 60° C. under a nitrogen stream for 12 hours. The resulting mixture was added to 1000 mL of methanol, the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, and an appropriate amount of organic solvent was removed, followed by recrystallization with methanol to obtain an intermediate (41)A (13.9). g, yield of 60%).

Synthesis of Intermediate (41)B(1)

In a 1L flask, 5H-benzofuro [3,2-c] carbazole (40 g, 155.47 mmol), bromobenzene (293.3 g, 186.56 mmol), trisdibenzyl Lidenacetone diphilladium (4.27 g, 4.66 mmol) and sodium-t-butoxide (19.4 g, 202.11 mmol) were added, and 750 ml of xylene was added, followed by stirring. Tri-t-butylphosphine (3.4 ml, 50% solution (toluene)) was added and then heated to 130° C. under a nitrogen stream for 12 hours. The obtained reactant was cooled to room temperature, and the reactant was poured into 1 L of methanol to filter the resulting solid, and then recrystallized using dichloromethane and methanol to obtain an intermediate (41)B(1) (25g, 48%). .

Synthesis of Intermediate (41)B

In a reactor, the intermediate (41)B(1) (25g, 74.99 mmol) was dissolved in 250 ml of tetrahydrofuran, and then the reactor was cooled using liquid nitrogen, n-butyllithium (35.99 ml, 89.99 mmol) was added dropwise using a syringe, stirred at room temperature for 6 hours, and then the reactor was cooled again. Here, trimethyl borate (10.03 ml, 89.99) was slowly added dropwise, and the resulting reaction product was stirred for 8 hours, poured into 900 ml of 1N-HCl aqueous solution, stirred, extracted with dichloromethane, and recrystallized using dichloromethane and hexane. Intermediate (41)B (20 g, 71%) was obtained.

Synthesis of compound (41)-1

In a flask of 500 ml, the above intermediate (41)A (13g, 43.80mmol), intermediate (41)B (16.52g, 43.80mmol), potassium carbonate (12.1g, 87.61mmol) and tetrakistriphenylphosphine (2.53g) , 2.19 mmol), 40 ml of water and 175 ml of 1,4-dioxane were added and heated at 100° C. for 12 hours. The reaction product obtained therefrom was poured into 500 ml of methanol, the resulting solid was filtered, and the obtained solid was recrystallized using 1,2-dichlorobenzene to obtain compound (41)-1 (20 g, 77%).

300 MHz (CDCl ₃ , ppm): 7.27~7.31 (m, 1H), 7.42~7.79 (m, 14H), 8.00~8.03 (m, 2H), 8.14~8.17 (d, 1H), 8.61~8.64 (m) , 2H), 8.69~8.74 (t, 2H), 8.97~8.99 (d, 1H)

Synthesis Example 42: Synthesis of compound (41)-4

Synthesis of intermediate (41)C(1)(benzo-methyl 3-ureidofuran-2-carboxylate)

To a solution of benzo-methyl 3-aminofuran-2-carboxylate (49.0 g, 0.25 mol) in dichloromethane (1000 ml) at -78 °C in a 1000 mL round flask was added chlorosulfonyl isocyanate (33.4 ml, 0.38 mol) was added dropwise. The reaction was slowly warmed to room temperature and stirred for 2 h. After concentration of the reaction, the residue was added to Conc. HCl (100 ml) was added and the mixture was stirred at 100° C. for 1 h. The reaction mixture was cooled to room temperature and neutralized with saturated aqueous NaHCO ₃ solution. The resulting solid was filtered to give intermediate (41)C(1) (benzo-ethyl 3-ureidofuran-2-carboxylate) (52.1 g, 87%) as a beige solid.

Synthesis of intermediate (41)C(2)(benzo-furo[3,2-d]pyrimidine-2,4-diol)

Intermediate (41)C(1) (benzo-ethyl 3-ureidofuran-2-carboxylate) (50.0 g, 0.21 mol) was suspended in 1000 ml of methanol in a 2000 mL round flask, and 2 M NaOH (300 ml) was added was added dropwise. The reaction mixture was stirred at reflux for 3 hours. The reaction mixture was cooled to room temperature, and Conc. Acidified to pH 3 with HCl. After concentration of the mixture, methanol is slowly added dropwise to the residue to precipitate a solid. The resulting solid was filtered and dried to obtain an intermediate (41)C(2)(benzo-furo[3,2-d]pyrimidine-2,4-diol) (38.0 g, 88%).

Synthesis of intermediate (41)C(3)(benzo-2,4-dichlorofuro[3,2-d]pyrimidine)

Dissolve intermediate (41)C(2)(benzo-furo[3,2-d]pyrimidine-2,4-diol) (37.2 g, 0.18 mol) in phosphorus oxychloride (500 ml) in a 1000 mL round flask did it The mixture was cooled to -30°C and N,N-diisopropylethylamine (52 ml, 0.36 mol) was added slowly. The reaction was stirred at reflux for 36 h, then cooled to room temperature. Then the reaction was poured into ice/water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous NaHCO3 solution, and then dried using Na ₂ SO ₄ . The organic layer obtained therefrom was concentrated to give the intermediate (41)C(3)(benzo-2,4-dichlorofuro[3,2-d]pyrimidine) (20.4 g, 46%).

Synthesis of intermediate (41)C

In a 2000 mL flask, 40.0 g (167.3 mmol) of intermediate (41)C(3), 22.4 g (184.1 mmol) of phenylboronic acid, 57.8 g (418.3 mmol) of potassium carbonate, Pd(PPh ₃ ) ₄ (Tetrakis (triphenylphosphine) )??palladium(0)) 9.7 g (8.4 mmol) was added to 500 mL of 1,4-dioxane and 250 mL of water, and then heated to 40° C. for 8 hours under a nitrogen stream. The resulting mixture was added to 1500 mL of methanol, the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, and an appropriate amount of organic solvent was removed, followed by recrystallization with methanol to intermediate (41)C (31.0). g, yield of 66%).

Synthesis of compound (41)-4

Instead of intermediate (41)A (13g, 43.80mmol), intermediate (41)B (16.52g, 43.80mmol), potassium carbonate (12.1g, 87.61mmol) and tetrakistriphenylphosphine (2.53g, 2.19mmol), Intermediate (41)C (15g, 53.44mmol), Intermediate (41)B (20.16g, 53.44mmol), potasumcarbonate (14.7g, 106.8mmol) and tetrakistriphenylphosphine (3.09g, 2.67mmol) were prepared Compound (41)-4 (21 g, 68%) was obtained by using the same method as for the synthesis of compound (41)-1 of Synthesis Example 41, except that it was used.

300 MHz (CDCl ₃ , ppm): 7.26~7.32 (m, 1H), 7.41~7.82 (m, 15H), 7.98~8.04 (d, 1H), 8.10~8.15 (d, 1H), 8.53~8.55 (d , 1H), 8.61~8.64 (d, 1H), 8.71~8.75 (d, 1H), 9.00~9.05 (d, 2H)

Synthesis Example 43: Synthesis of compound (41)-25

5H-benzofuro[3,2-c]carbazole (40 g, 155.47 mmol) and bromobenzene (293.3 g, 186.56 mmol) instead of 5H-benzofurano Intermediate (41)B(1) of Synthesis Example 41, except that [3,2-c]carbazole (14g, 54.41mmol) and Intermediate (41)A (19.38g, 65.30mmol) were used. Compound (41)-25 (21 g, 75%) was obtained by using the same method as the synthesis method of

calcd. C ₃₄ H ₁₉ N ₃ OS: C, 78.90; H, 3.70; N, 8.12; O, 3.09; S, 6.19; found: C, 78.84; H, 3.71; N, 8.15

Synthesis Example 44: Synthesis of compound (41)-26

5H-benzofuro[3,2-c]carbazole (40 g, 155.47 mmol) and bromobenzene (293.3 g, 186.56 mmol) instead of 5H-benzothiano Intermediate (41)B(1) of Synthesis Example 41, except that [3,2-c]carbazole (15g, 54.48mmol), Intermediate (41)C (19.40g, 65.37mmol) was used. Compound (41)-26 (22g, 76%) was obtained by using the same method as the synthesis method of

calcd. C ₃₄ H ₁₉ N ₃ S ₂ : C, 76.52; H, 3.59; N, 7.87; S, 12.02; found: C, 76.54; H, 3.60; N, 7.88

Synthesis Example 45: Synthesis of compound (41)-27

Synthesis of Intermediate (41)F(1)

In a 500 ml flask, put 7-bromobenzo [b] thiophen-3 (2H) -one (18.1 g, 78.81 mmol) and benzaldehyde (5.1 g, 78.81 mmol) and sodium hydroxide (4.729 g, 118.22 mmol) After adding 160 ml of ethanol, the mixture was stirred at room temperature for 12 hours. The obtained solid was filtered and washed with ethanol to obtain an intermediate (41)F(1) (12 g, 48%).

Synthesis of intermediate (41)F

Intermediate (41)F(1) (7.6g, 23.96mmol), benzamidine hydrochloride (2.3g, 23.93mmol), and sodium hydroxide (2.875g, 71.89mmol) were added to 100 ml of ethanol and heated to 12 at room temperature. stirred for hours. The obtained solid was filtered and purified by column chromatography using dichloromethane and hexane as solvents to obtain an intermediate (41)F (5.3 g, 53%).

Synthesis of compound (41)-27

Instead of 5H-benzofuro[3,2-c]carbazole (40 g, 155.47 mmol) and bromobenzene (293.3 g, 186.56 mmol), 11,12-di Intermediate of Synthesis Example 41, except that hydro-11-phenylindolo[2,3-a]carbazole (3g, 9.03 mmol) and Intermediate (41)F (4.52g, 10.83 mmol) were used. Compound (41)-27 (3.5 g, 58%) was obtained by using the same method as for the synthesis of (41) B(1).

calcd. C ₄₆ H ₂₈ N ₄ S: C, 82.61; H, 4.22; N, 8.38; S, 4.79; found: C, 82.60; H, 4.25; N, 8.39

Synthesis Example 51: Synthesis of compound (51)-103

Intermediate (51)A 15g (39.12 mmol) and Intermediate (51)B 18.18g (46.94 mol) with Pd ₂ (dba) ₃ (Tris(dibenzylideneacetone) dipalladium(0)) 1.075 g (1.17 mmol), P( t-Bu) ₃ (Tri-tert-butylphosphine) 1.716 g (3.52 mmol) and NaO(t-Bu) 4.887 g (50.86 mmol) were placed in a flask, and then 200 mL of Xylene was added and 18 hours under a nitrogen atmosphere. while stirring at reflux. The resultant obtained therefrom was slowly poured into 800 mL of methanol, the resulting solid was filtered and vacuum dried, and the solid obtained by recrystallization was dissolved in 200 mL of monochlorobenzene, filtered and dried under vacuum to compound (51)-103 18.31 g (yield 68%) was obtained.

¹ H-NMR (300 MHz, CDCl 3 ): 9.35 (s, 1 H); 9.08(d, 1H); 8.99(t, 1H); 8.24 (m, 4H); 8.20(d, 1H); 8.08(d, 1H); 8.04(s, 1H); 7.98(d, 1H); 8.86(t, 1H); 7.69(d, 1H); 7.62(t, 2H); 7.57 (m, 3H); 7.49 (m, 6H); 7.38 (m, 4H); 7.28 (m, 3H).

Synthesis Example 52: Synthesis of compound (51)-104

Intermediate (51)A 15 g (39.12 mmol) and Intermediate (51)C 18.23 g (46.94 mol) with Pd ₂ (dba) ₃ (Tris(dibenzylideneacetone) dipalladium(0)) 1.075 g (1.17 mmol), P( t-Bu) ₃ (Tri-tert-butylphosphine) 1.716 g (3.52 mmol) and NaO(t-Bu) 4.887 g (50.86 mmol) were placed in a flask, and then 200 mL of Xylene was added and 18 hours under a nitrogen atmosphere. while stirring at reflux. The resultant obtained therefrom was slowly poured into 800 mL of methanol, the resulting solid was filtered and vacuum dried, and the solid obtained by recrystallization was dissolved in 200 mL of monochlorobenzene, filtered and dried under vacuum to compound (51)-104 16.10 g (yield 60%) was obtained.

HRMS calcd for C48H30N6: m/z 690.2532. Found: 690.2533.

Synthesis Example 61: Synthesis of compound 16

Synthesis of intermediate 61A(1) (benzo-1H-thieno[3,2-d]pyrimidine-2,4-dione)

In a 2000 mL round flask, a mixture of benzo-methyl 3-amino-2-thiophenecarboxylate (47.5 g, 0.23 mol) and urea (79.4 g, 1.15 mol) was stirred at 200° C. for 2 hours. After cooling the hot reaction mixture to room temperature, it was poured into sodium hydroxide solution, impurities were removed by filtration, and the reaction product was acidified (HCl, 2N), and the obtained precipitate was dried to obtain an intermediate 61A (1) (35 g, 75%).

calcd. C ₁₀ H ₆ N ₂ O ₂ S: C, 55.04; H, 2.77; N, 12.84; O, 14.66; S, 14.69; found: C, 55.01; H, 2.79; N, 12.81; O, 14.69; S, 14.70

Synthesis of intermediate 61A (benzo-2,4-dichloro-thieno[3,2-d]pyrimidine)

A mixture of intermediate A(1) (benzo-1H-thieno[3,2-d]pyrimidine-2,4-dione) (35 g, 0.16 mol) and phosphorus oxychloride (600 mL) in a 1000 mL round flask Stirred under reflux for 6 hours. The reaction mixture was cooled to room temperature and poured into ice/water with vigorous stirring to form a precipitate. The resulting reaction was filtered to give Intermediate A (benzo-2,4-dichloro-thieno[3,2-d]pyrimidine) (35 g, 85%, white solid). Elemental analysis results and NMR analysis results of the produced intermediate 61A are as follows.

calcd. C ₁₀ H ₄ Cl ₂ N ₂ S: C, 47.08; H, 1.58; Cl, 27.79; N, 10.98; S, 12.57; found: C, 47.03; H, 1.61; Cl, 27.81; N, 10.98; S, 12.60

300 MHz (CDCl ₃ , ppm): 7.63 (t, 1H), 7.76 (t, 4H), 7.95 (d, 1H), 8.53 (d, 1H)

Synthesis of Intermediate 61A-16

In a 2000 mL round flask, 25.0 g (98.5 mmol) of intermediate 61A, 40.01 g (108.35 mmol) of phenyl-3-boronic ester-carbazole, 34.04 g (246.26 mmol) of potassium carbonate, Pd(PPh ₃ ) ₄ (Tetrakis(triphenylphosphine) )??palladium(0)) 5.7 g (4.93 mmol) was added to 600 mL of 1,4-dioxane and 300 mL of water, and then heated to reflux under a nitrogen stream for 6 hours. The resulting mixture was added to 1500 mL of methanol and the crystallized solid was filtered, dissolved in monochlorobenzene and filtered through silica gel/celite, an appropriate amount of organic solvent was removed, and recrystallized with methanol to obtain Intermediate 61A-16 (31.85 g , a yield of 70%) was obtained.

calcd. C ₂₈ H ₁₆ ClN ₃ S: C, 72.80; H, 3.49; Cl, 7.67; N, 9.10; S, 6.94; found: C, 72.43; H, 3.54; Cl, 7.69; N, 9.29; S, 6.70;

Synthesis of compound (61)-16

In a 1000 mL round flask, 29.6 g (64.04 mmol) of intermediate 61A-16, 11.2 g (67.25 mmol) of carbazole, 12.3 g (128.1 mmol) of sodium t-butoxide, 3.7 g (6.4 mmol) of Pd(dba) ₂ , tri 5.2 mL of t-butylphosphine (50% in toluene) was placed in 400 mL of xylene, and heated to reflux under a nitrogen stream for 15 hours. The resulting mixture was added to 1000 mL of methanol, the crystallized solid was filtered, dissolved in dichlorobenzene, filtered through silica gel/celite, an appropriate amount of organic solvent was removed, and recrystallized from methanol to obtain compound 16 (26.0 g, 68 %) was obtained. Elemental analysis results and NMR analysis results of the resulting compound (61)-16 are as follows.

calcd. C ₄₀ H ₂₄ N ₄ S: C, 81.06; H, 4.08; N, 9.45; S, 5.41; found: C, 81.00; H, 4.12; N, 9.40.69; S, 5.30;

300 MHz (CDCl ₃ , ppm): 7.37-7.70 (m, 15H), 7.93 (d, 1H), 8.12 (d, 2H), 8.28 (d, 1H), 8.45 (dd, 1H), 8.68 (d, 1H), 9.12 (d, 2H), 9.21 (d, 1H)

Synthesis Example 62: Synthesis of compound (61)-9

Into a 500 mL flask, 100 ml of DMF is added, and sodium hydride 2.8 g (32.2 mmol) is added. After lowering the internal temperature of the flask to 0°C, 11.8 g (70.5 mmol) of carbazole was slowly added thereto, followed by stirring at 0°C for 1 hour. After slowly adding 15.0 g (58.8 mmol) of Intermediate 61A, the mixture was stirred at room temperature for 1 hour, and then slowly warmed to room temperature. After an additional hour at room temperature, the reaction mixture was quenched by pouring ice/water. The aqueous solution was extracted with methylene chloride. The organic layer was dried over sodium sulfate and concentrated in vacuo. Dissolved in methylene chloride and recrystallized with methanol to obtain compound (61)-9 (13.6 g, 60% yield). Elemental analysis results and NMR analysis results of the resulting compound (61)-9 are as follows.

calcd. C ₃₄ H ₂₀ N ₄ S: C, 79.05; H, 3.90; N, 10.84; S, 6.21; found: C, 79.17; H, 3.78; N, 10.73; S, 6.07;

300 MHz (CDCl ₃ , ppm): 7.38-7.53 (m, 8H), 7.68-7.74 (m, 2H), 7.82-7.89 (m, 3H), 8.13 (d, 2H), 8.22 (dd, 2H), 8.76 (dd, 1H), 9.22 (d, 2H)

Synthesis Example 63: Synthesis of compound (61)-29

Synthesis of intermediate 61A-29

In a 1000 mL flask, 20.0 g (78.4 mmol) of intermediate 61A, 11.0 g (90.15 mmol) of phenylboronic acid, 27.09 g (195.99 mmol) of potassium carbonate, Pd(PPh ₃ ) ₄ (Tetrakis- (triphenylphosphine)??palladium(0)) After adding 4.53 g (3.9 mmol) to 300 mL of 1,4-dioxane and 150 mL of water, it was heated to 60° C. under a nitrogen stream for 12 hours. The resulting mixture was added to 1000 mL of methanol, the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, and an appropriate amount of organic solvent was removed, followed by recrystallization with methanol to obtain Intermediate 61A-29 (13.9 g , a yield of 60%) was obtained.

calcd. C ₁₆ H ₉ ClN ₂ S: C, 64.75; H, 3.06; Cl, 11.95; N, 9.44; S, 10.80; found: C, 63.17; H, 3.08; Cl, 12.13; N, 9.37; S, 10.82

Synthesis of compound (61)-29

In a 500 mL round flask, 13.9 g (46.8 mmol) of intermediate 61A-29, 23.2 g (53.86 mmol) of triphenylene-phenyl-boronic ester, 16.2 g (117.1 mmol) of potassium carbonate, Pd(PPh ₃ ) ₄ (Tetrakis- (triphenylphosphine) Palladium(0)) 2.7 g (2.3 mmol) was added to 150 mL of 1,4-dioxane and 75 mL of water, and then heated to reflux under a nitrogen stream for 6 hours. The resulting mixture was added to 500 mL of methanol and the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, an appropriate amount of organic solvent was removed, and recrystallized with methanol to obtain Compound 29 (16.7 g, 64 %) was obtained. Elemental analysis results and NMR analysis results of the resulting compound (61)-29 are as follows.

calcd. C ₄₀ H ₂₄ N ₂ S: C, 85.08; H, 4.28; N, 4.96; S, 5.68; found: C, 84.95; H, 4.18; N, 5.17; S, 5.72

300 MHz (CDCl ₃ , ppm): 7.61-7.73 (m, 10H), 8.07 (t, 2H), 8.16 (d, 1H), 8.28 (d, 1H), 8.65 (t, 1H), 8.74 (s, 3H), 8.85-8.92 (m, 2H), 9.04 (s, 2H)

Synthesis Example 64: Synthesis of compound (61)-30

In a 250 mL round flask, 10.0 g (33.7 mmol) of intermediate 61A-29, 19.6 g (38.8 mmol) of triphenylene-biphenyl-boronic ester, 11.6 g (84.2 mmol) of potassium carbonate, Pd(PPh ₃ ) ₄ (Tetrakis) - (triphenylphosphine) palladium(0)) 1.9 g (1.68 mmol) was added to 100 mL of 1,4-dioxane and 50 mL of water, and then heated to reflux under a nitrogen stream for 6 hours. The resulting mixture was added to 300 mL of methanol and the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, and an appropriate amount of organic solvent was removed, followed by recrystallization with methanol to compound (61)-30 ( 14.0 g, yield of 65%). Elemental analysis results and NMR analysis results of the resulting compound (61)-30 are as follows.

calcd. C ₄₆ H ₂₈ N ₂ S: C, 86.22; H, 4.40; N, 4.37; S, 5.00; found: C, 85.95; H, 4.58; N, 4.17; S, 5.02

300 MHz (CDCl ₃ , ppm): 7.63-7.91 (m, 12H), 8.05 (d, 1H), 8.10 (d, 1H), 8.18 (d, 1H), 8.27 (d, 1H), 8.33 (s, 1H), 8.39 (dd, 2H), 8.77 (t, 2H), 8.81-8.92 (m, 3H), 8.95 (d, 1H), 9.08-9.12 (m, 2H), 9.20 (s, 1H)

Synthesis Example 85: Synthesis of compound (61)-37

Synthesis of intermediate 61B(1) (benzo-methyl 3-ureidofuran-2-carboxylate)

To a solution of benzo-methyl 3-aminofuran-2-carboxylate (49.0 g, 0.25 mol) in dichloromethane (1000 ml) at -78 °C in a 1000 mL round flask was added chlorosulfonyl isocyanate (33.4 ml, 0.38 mol) was added dropwise. The reaction was slowly warmed to room temperature and stirred for 2 h. After concentration of the reaction, the residue was added to Conc. HCl (100 ml) was added and the mixture was stirred at 100° C. for 1 h. The reaction mixture was cooled to room temperature and neutralized with saturated aqueous NaHCO3 solution. The resulting solid was filtered to give intermediate 61B(1) (benzo-ethyl 3-ureidofuran-2-carboxylate) (52.1 g, 87%) as a beige solid.

calcd. C ₁₁ H ₁₀ N ₂ O ₄ : C, 56.41; H, 4.30; N, 11.96; O, 27.33; found: C, 56.45; H, 4.28; N, 11.94; O, 27.32

Synthesis of intermediate 61B(2) (benzo-furo[3,2-d]pyrimidine-2,4-diol)

In a 2000 mL round flask, intermediate 61B(1) (benzo-ethyl 3-ureidofuran-2-carboxylate) (50.0 g, 0.21 mol) was suspended in 1000 mL of methanol, and 2 M NaOH (300 mL) was added dropwise. The reaction mixture was stirred at reflux for 3 hours. The reaction mixture was cooled to room temperature, and Conc. Acidified to pH 3 with HCl. After concentration of the mixture, methanol is slowly added dropwise to the residue to precipitate a solid. The resulting solid was filtered and dried to obtain an intermediate 61B(2) (benzo-furo[3,2-d]pyrimidine-2,4-diol) (38.0 g, 88%).

calcd. C ₁₀ H ₆ N ₂ O ₃ : C, 59.41; H, 2.99; N, 13.86; O, 23.74; found: C, 59.41; H, 2.96; N, 13.81; O, 23.75

Intermediate 61B (benzo-2,4-dichlorofuro[3,2-d]pyrimidine)

Intermediate 61B(2) (benzo-furo[3,2-d]pyrimidine-2,4-diol) (37.2 g, 0.18 mol) was dissolved in phosphorus oxychloride (500 ml) in a 1000 mL round flask. The mixture was cooled to -30°C and N,N-diisopropylethylamine (52 ml, 0.36 mol) was added slowly. The reaction was stirred at reflux for 36 h, then cooled to room temperature. Then the reaction was poured into ice/water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous NaHCO3 solution, and then dried using Na ₂ SO ₄ . The organic layer obtained therefrom was concentrated to give an intermediate 61B (benzo-2,4-dichlorofuro[3,2-d]pyrimidine) (20.4 g, 46%).

Elemental analysis results and NMR analysis results of the produced intermediate 61B are as follows.

calcd. C ₁₀ H ₄ Cl ₂ N ₂ O: C, 50.24; H, 1.69; Cl, 29.66; N, 11.72; O, 6.69; found: C, 50.18; H, 1.79; Cl, 29.69; N, 11.69; O, 6.70;

300 MHz (CDCl ₃ , ppm): 7.55 (t, 1H), 7.71-7.82 (m, 2H), 8.25 (d, 1H)

Synthesis of intermediate 61B-37

In a 2000 mL flask, 40.0 g (167.3 mmol) of intermediate 61B, 22.4 g (184.1 mmol) of phenylboronic acid, 57.8 g (418.3 mmol) of potassium carbonate, Pd(PPh ₃ ) ₄ (Tetrakis (triphenylphosphine)??palladium(0) )) 9.7 g (8.4 mmol) was added to 500 mL of 1,4-dioxane and 250 mL of water, and then heated to 40° C. under a nitrogen stream for 8 hours. The resulting mixture was added to 1500 mL of methanol and the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, an appropriate amount of organic solvent was removed, and recrystallized from methanol to obtain Intermediate 61B-37 (31.0 g , a yield of 66%) was obtained.

calcd. C ₁₆ H ₉ ClN ₂ O: C, 68.46; H, 3.23; Cl, 12.63; N, 9.98; O, 5.70; found: C, 68.95; H, 3.08; Cl, 12.17; N, 10.01; O, 5.62

Synthesis of compound (61)-37

In a 500 mL round flask, 10.2 g (36.5 mmol) of intermediate 61B-37, 6.7 g (40.1 mmol) of carbazole, 7.0 g (72.9 mmol) of sodium t-butoxide, 2.1 g (3.7 mmol) of Pd(dba) ₂ , tri 2.9 mL of t-butylphosphine (50% in toluene) was placed in 250 mL of xylene, and heated to reflux under a nitrogen stream for 15 hours. The resulting mixture was added to 1000 mL of methanol, the crystallized solid was filtered, dissolved in dichlorobenzene, filtered through silica gel/celite, and an appropriate amount of the organic solvent was removed, followed by recrystallization with methanol to compound (61)-37 ( 9.8 g, yield of 65%). Elemental analysis results and NMR analysis results of the resulting compound (61)-37 are as follows.

calcd. C ₂₈ H ₁₇ N ₃ O: C, 81.73; H, 4.16; N, 10.21; O, 3.89; found: C, 82.94; H, 4.08; N, 9.17; S, 4.02

300 MHz (CDCl ₃ , ppm): 7.37-7.42 (m, 2H), 7.53-7.77 (m, 8H), 8.13 (d, 2H), 8.39 (dd, 1H), 8.73-8.76 (m, 2H), 8.92 (d, 2H)

Synthesis Example 66: Synthesis of compound (61)-40

Synthesis of Intermediate 61B-40

In a 500 mL flask, put 250 ml of THF and add 4.5 g (46.6 mmol) of sodium thi-butoxide. After lowering the internal temperature of the flask to 0°C, 6.8 g (40.8 mmol) of carbazole was slowly added thereto, followed by stirring at 0°C for 1 hour. After the slow addition of 9.0 g (38.9 mmol) of Intermediate 61B, the mixture was stirred at room temperature for 1 hour, and then slowly warmed to room temperature. After 1 hour at room temperature, the resulting solid was filtered to give the intermediate 61B-40 (11.0 g, 73% yield).

calcd. C ₂₂ H ₁₂ ClN ₃ S: C, 68.48; H, 3.13; Cl, 9.19; N, 10.89; S, 8.31; found: C, 68.38; H, 3.03; Cl, 9.30; N, 10.99; S, 8.14

Synthesis of compound (61)-40

In a 500 mL flask, 15.0 g (40.6 mmol) of intermediate 61B-40, 5.4 g (44.6 mmol) of phenylboronic acid, 14.0 g (101.41 mmol) of potassium carbonate, Pd(PPh ₃ ) ₄ (Tetrakis (triphenylphosphine)??palladium(0) )) 2.3 g (2.0 mmol) was added to 130 mL of 1,4-dioxane and 65 mL of water, and then heated to reflux under a nitrogen stream for 6 hours. The resulting mixture was added to 400 mL of methanol, the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, an appropriate amount of organic solvent was removed, and recrystallized from methanol to compound 40 (12.0 g, 72 %) was obtained. Elemental analysis results and NMR analysis results of the resulting compound (61)-40 are as follows.

calcd. C ₂₈ H ₁₇ N ₃ S: C, 78.66; H, 4.01; N, 9.83; S, 7.50; found: 77.06; H, 3.71; N, 9.87; S, 7.53

300 MHz (CDCl ₃ , ppm): 7.39-7.74 (m, 10H), 7.91 (d, 2H), 8.17 (d, 2H), 8.41 (dd, 1H), 8.67-8.71 (m, 2H)

Synthesis Example 67: Synthesis of compound (61)-48

Synthesis of intermediate 61B-48

In a 1000 mL flask, 15.0 g (62.7 mmol) of intermediate 61B, 27.8 g (75.3 mmol) of phenyl-3-boronic ester-carbazole, 21.68 g (156.86 mmol) of potassium carbonate, Pd(PPh ₃ ) ₄ (Tetrakis(triphenylphosphine) Palladium(0)) 3.6 g (3.1 mmol) was added to 400 mL of 1,4-dioxane and 200 mL of water, and then heated to reflux under a nitrogen stream for 6 hours. The resulting mixture was added to 1200 mL of methanol, the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, an appropriate amount of organic solvent was removed, and recrystallized from methanol to obtain Intermediate 61B-48 (15.39 g , a yield of 55%) was obtained.

Calcd. C ₂₈ H ₁₆ ClN ₃ O: C, 75.42; H, 3.62; Cl, 7.95; N, 9.42; O, 3.59; found: C, 75.12; H, 3.48; Cl, 7.90; N, 10.02; O, 3.51;

Synthesis of compound (61)-48

In a 500 mL round flask, 14.6 g (32.8 mmol) of intermediate 61B-48, 6.0 g (36.1 mmol) of carbazole, 6.3 g (65.5 mmol) of sodium t-butoxide, 1.8 g (3.3 mmol) of Pd(dba) ₂ , tri 2.6 mL of t-butylphosphine (50% in toluene) was placed in 200 mL of xylene, and heated to reflux under a nitrogen stream for 15 hours. The resulting mixture was added to 600 mL of methanol and the crystallized solid was filtered, dissolved in dichlorobenzene, filtered through silica gel/celite, and an appropriate amount of organic solvent was removed, followed by recrystallization with methanol to compound (61)-48 ( 15.0 g, yield of 79%). Elemental analysis results and NMR analysis results of the resulting compound (61)-48 are as follows.

calcd. C ₄₀ H ₂₄ N ₄ O: C, 83.31; H, 4.20; N, 9.72; O, 2.77; found: C, 81.13; H, 3.94; N, 9.81; O, 2.79

300 MHz (CDCl ₃ , ppm): 7.17-7.70 (m, 15H), 7.90 (d, 1H), 8.18 (d, 2H), 8.29 (d, 1H), 8.32 (dd, 1H), 8.73 (d, 1H), 9.19 (d, 2H), 9.31 (d, 1H)

Synthesis Example 68: Synthesis of compound (61)-5

Synthesis of intermediate 61A-5

Using the same method as for the synthesis of Intermediate 61A-16 of Synthesis Example 61, except that phenylboronic acid was used instead of phenyl-3-boronic ester-carbazole, Intermediate 61A-5 (13.40 g , 60% yield) was synthesized.

calcd. C ₁₆ H ₉ ClN ₂ S: C, 64.75; H, 3.06; Cl, 11.95; N, 9.44; S, 10.80; found: C, 62.36; H, 3.16; Cl, 10.37; N, 9.54; S, 10.77

Synthesis of compound (61)-5

Compound (61)-5 (10.77g; 64% yield) was synthesized.

calcd. C ₂₈ H ₁₇ N ₃ S: C, 78.66; H, 4.01; N, 9.83; S, 7.50; found: C, 75.92; H, 3.92; N, 9.03; S, 7.38

300 MHz (CDCl ₃ , ppm): 7.39-7.45 (m, 2H), 7.55-7.79 (m, 8H), 8.24 (d, 2H), 8.40 (dd, 1H), 8.71-8.73 (m, 2H), 8.89 (d, 2H)

Synthesis Example 69: Synthesis of compound (61)-21

Synthesis of intermediate 61A-21

Intermediate 61A-21 (20.15 g, 53% yield) was synthesized using the same method as for the synthesis of Intermediate 61B-40 of Synthesis Example 66, except that Intermediate 61A was used instead of Intermediate 61B. .

calcd. C ₂₂ H ₁₂ ClN ₃ S: C, 68.48; H, 3.13; Cl, 9.19; N, 10.89; S, 8.31; found: C, 67.94; H, 3.23; Cl, 8.81; N, 10.36; S, 8.15

Synthesis of compound (61)-21

The method for synthesizing compound (61)-40 of Synthesis Example 66, except that Intermediate 61A-21 and phenyl-3-boronic ester-carbazole were used instead of Intermediate 61B-40 and phenylboronic acid, respectively Using the same method, compound (61)-21 (12.47 g, yield of 67%) was synthesized.

calcd. C ₄₀ H ₂₄ N ₄ S: C, 81.06; H, 4.08; N, 9.45; S, 5.41; found: C, 80.13; H, 3.74; N, 9.30; S, 5.23

300 MHz (CDCl ₃ , ppm): 7.25-7.33 (m, 4H), 7.45-7.64 (m, 11H), 7.77 (s, 1H), 7.94-8.18 (m, 7H), 8.55 (d, 1H)

Synthesis Example 70A: Synthesis of compound (61)-27

Synthesis of intermediate 61A-27

Using the same method as for the synthesis of Intermediate 61A-29 of Synthesis Example 63, except that triphenylene-biphenyl-boronic ester was used instead of phenylboronic acid, Intermediate 61A-27 (25.34 g, 68% yield) was synthesized.

calcd. C ₄₀ H ₂₃ ClN ₂ S: C, 80.19; H, 3.87; Cl, 5.92; N, 4.68; S, 5.35; found: C, 78.57; H, 3.39; Cl, 5.68; N, 4.32; S, 5.15

Synthesis of compound (61)-27

The method for synthesizing compound (61)-29 of Synthesis Example 63, except that Intermediate 61A-27 and phenylboronic acid were used instead of Intermediate 61A-29 and triphenylene-biphenyl-boronic ester, respectively Using the same method, compound (61)-27 (15.37 g, yield of 56%) was synthesized.

calcd. C ₄₆ H ₂₈ N ₂ S: C, 86.22; H, 4.40; N, 4.37; S, 5.00; found: C, 85.18; H, 4.28; N, 4.14; S, 4.83

300 MHz (CDCl ₃ , ppm): 7.41-7.57 (m, 10H), 7.70-7.88 (m, 7H), 7.98-8.18 (m, 6H), 8.28 (d, 2H), 8.93 (d, 2H), 9.15 (s, 1H)

Synthesis Example 71A: Synthesis of compound (61)-12

The point that 9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole was used instead of phenyl-3-boronic ester-carbazole Except for , compound (61)-12 (17.4 g, yield of 62%) was synthesized using the same method as for the synthesis of compound (61)-21 of Synthesis Example 69.

calcd. C ₄₀ H ₂₄ N ₄ S: C, 81.06; H, 4.08; N, 9.45; S, 5.41; found: C, 80.21; H, 3.82; N, 9.03; S, 5.17

300 MHz (CDCl ₃ , ppm): 7.25-7.33 (m, 6H), 7.50-7.52 (m, 4H), 7.63-7.68 (m, 4H), 7.79 (d, 2H), 7.94-8.12 (m, 6H) ), 8.55 (d, 2H)

Synthesis Example 72A: Synthesis of compound (61)-13

The point that 9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole was used instead of phenyl-3-boronic ester-carbazole Except for, compound (61)-13 (7.7 g, yield of 65%) was synthesized using the same method as for the synthesis of compound (61)-21 of Synthesis Example 69.

calcd. C ₄₀ H ₂₄ N ₄ S: C, 81.06; H, 4.08; N, 9.45; S, 5.41; found: C, 79.47; H, 3.89; N, 9.37; S, 5.36

300 MHz (CDCl ₃ , ppm): 7.25-7.33 (m, 6H), 7.46-7.52 (m, 6H), 7.63 (d, 2H), 7.94-8.12 (m, 7H), 8.28 (d, 1H), 8.55 (d, 2H)

Synthesis Example 73A: Synthesis of compound (61)-18

The above synthesis example, except that 9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole was used instead of carbazole Compound (61)-18 (11.4 g, 71% yield) was synthesized using the same method as for the synthesis of compound (61)-16 of 61.

calcd. C ₄₆ H ₂₈ N ₄ S: C, 82.61; H, 4.22; N, 8.38; S, 4.79; found: C, 78.97; H, 4.01; N, 7.78; S, 4.42

300 MHz (CDCl ₃ , ppm): 7.25-7.33 (m, 5H), 7.45-7.69 (m, 12H), 7.77 (s, 1H), 7.87-8.12 (m, 7H), 8.28 (d, 1H), 8.55 (d, 2H)

Synthesis Example 74A: Synthesis of compound (61)-11

In a 500 mL flask, 8.38 g (37.9 mmol) of intermediate 61(11), 9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole 14.02 g (37.9 mmol), potassium carbonate 13.1 g (94.93 mmol) and Pd(PPh ₃ ) ₄ (Tetrakis (triphenylphosphine) palladium(0)) 2.19 g (1.90 mmol) were mixed with 140 mL of 1,4-dioxane and water After mixing with 70 mL, it was heated to reflux under a nitrogen stream for 6 hours. The resulting mixture was added to 500 mL of methanol and the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, and an appropriate amount of organic solvent was removed, followed by recrystallization with methanol to compound (61)-11 ( 10.9 g, yield of 67%). Elemental analysis results and NMR analysis results of the resulting compound (61)-11 are as follows.

calcd. C ₂₈ H ₁₇ N ₃ S: C, 78.66; H, 4.01; N, 9.83; S, 7.50; found: C, 76.55; H, 3.76; N, 9.36; S, 7.42

300 MHz (CDCl ₃ , ppm): 7.25-7.33 (m, 3H), 7.46-7.52 (m, 5H), 7.63 (d, 1H), 7.94-8.12 (m, 5H), 8.28 (d, 1H), 8.50 (s, 1H), 8.55 (d, 1H)

Synthesis Example 75A: Synthesis of compound (61)-45

Except for using 9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole instead of phenylboronic acid, the above synthesis Compound (61)-45 (8.6 g, 70% yield) was synthesized using the same method as for synthesizing compound (61)-40 in Example 66.

calcd. C ₄₀ H ₂₄ N ₄ O: C, 83.31; H, 4.20; N, 9.72; O, 2.77; found: C, 82.16; H, 3.94; N, 9.83; O, 2.64

300 MHz (CDCl ₃ , ppm): 7.25-7.51 (m, 12H), 7.63-7.70 (m, 4H), 7.94 (d, 2H), 8.09-8.12 (m, 3H), 8.28 (d, 1H), 8.55 (d, 2H)

Synthesis Example 76A: Synthesis of compound (61)-401

Synthesis of Intermediate 61(1)

3-iodo-4-nitro-1,1'-biphenyl (3-iodo-4-nitro-1,1'-biphenyl) (20.1 g, 61.8 mmol), (2-bromophenyl) in a 2-neck flask ) Boronic acid ((2-bromophenyl) boronic acid) (18.6 g, 92.7 mmol), triphenylphosphine _, (2.4 g, 9.2 mmol), tetrakis (triphenylphosphine) palladium (0) (Tetrakis (triphenylphosphine)palladium(0)) (Pd(PPh ₃ ) ₄ , 0.7 g, 3.1 mmol) and potassium carbonate (K ₂ CO ₃ ,17.1 g, 123.7 mmol) were added, and 800 ml of toluene and 80 ml of H ₂ O were added. Then, it was substituted with argon and refluxed for 12 hours. Thereafter, the organic layer was cooled to room temperature and extracted with ethyl acetate (Ethyl Acetate, EA) to remove moisture using magnesium sulfate (MgSO ₄ ), then concentrated and column chromatography (hexane/EA = 10/1)) to obtain 47 g of intermediate 61(1) (yield = 75%).

¹ H NMR (CDCl ₃ , 300 MHz): 8.22 (d, 1H), 7.78 (dd, 1H), 7.70 to 7.64 (m, 3H), 7.56 (d, 1H), 7.52 to 7.39 (m, 4H), 7.33 ~7.26 (m, 2H).

Synthesis of Intermediate 61(2)

Intermediate 61(1) (25.8 g, 72.9 mmol) and PPh ₃ (57.4 g, 218.8 mmol) were put in a 1-neck flask, 80 ml of 1,2-dichlorobenzene (DCB) was added, followed by argon substitution for 12 hours was stirred at 150 °C. DCB was distilled off, cooled to room temperature, dissolved in a small amount of toluene, and purified by column chromatography (Hexane) to obtain 15 g of Intermediate 61(2) (yield = 64%).

¹ H NMR (CDCl ₃ , 300 MHz): 8.99 (s, 1H), 8.20 (b, 1H), 7.75-7.72 (m, 3H), 7.51-7.46 (m, 3H), 7.43-7.27 (m, 4H) .

Synthesis of Intermediate 61(3)

Intermediate 61(2) (32.0g, 99.3 mmol), Cu (0.63g, 9.9 mmole) and K ₂ CO ₃ (27.1 g, 198.6 mmol) were placed in a two-necked flask, and 320 ml of dimethylformamide (DMF) was added. , argon was substituted, and iodobenzene (22.5ml, 198.6 mmol) was added. Thereafter, after refluxing for 12 hours, cooling to room temperature, and extracting with EA to remove moisture from the obtained organic layer using MgSO ₄ , and then concentration, column chromatography (Hexane) was performed to perform column chromatography (Hexane) to form a white solid intermediate 61 (3) ) to obtain 25 g (yield = 64%). Intermediate 61(3) was identified through 1H-NMR and LC/MS (liquid chromatography mass spectrometry).

1H NMR (CDCl3, 300MHz): 9.07 (d, 1H), 7.75~7.71 (m, 3H), 7.69~7.61 (m, 2H), 7.55~7.40 (m, 7H), 7.37~7.31 (m, 2H) , 7.26~7.22 (dd, 1H)

LC/MS, calculated: C ₂₄ H ₁₆ BrN = 398.29, found: m/z = 398.1 (M+, 100 %)

Synthesis of intermediate 61A-401-1

Intermediate 61(3) (33 g, 83 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3, 2-dioxaborolane) (25 g, 100 mmol), potassium acetate (KOAc, 21 g, 210 mmol) and 1,1'-Bis(diphenylphosphino)ferrocene-palladium( II )dichloride (PdCl2(dppf)2, 3.4g, 4.2 mmol) was added to THF (200 mL), followed by stirring at 70° C. for 24 hours. After completion of the reaction, the reaction solution was extracted with water and EA, and water was removed from the organic layer obtained using MgSO ₄ , concentrated, and purified by column chromatography (methylene chloride/n-hexane=3/2, silica gel). Intermediate 61A-401-1 was obtained as a white solid (26 g, yield = 60 %).

¹ H NMR (CDCl ₃ , 300 MHz): 9.52 (s, 1H), 7.79~7.32 (m, 15H), 1.50 (s, 12H).

Synthesis of compound (61)-401

Intermediate 61A-401-1 (16.0 g, 36 mmol), Intermediate 61A-401-2 (15.0 g, 36 mmol), K ₂ CO ₃ (12 g, 89.8 mmol) and Pd(PPh ₃ ) ₄ (2.1 g, 1.8 mmol) was added to toluene (50 mL) and H ₂ O (20 ml), followed by stirring at 120° C. for 24 hours. After completion of the reaction, water was added, stirred, and filtered. A dark gray solid obtained by filtration was dissolved in hot toluene and filtered. The obtained toluene solution was precipitated using methanol, filtered, and the obtained solid was recrystallized from 1-chlorobenzene to obtain compound (61)-401 as yellow crystals (14.0 g, yield = 60%). The structure of the obtained compound (61)-401 was confirmed through LC/MS.

LC/MS, calculated: C ₄₆ H ₂₉ N ₃ S = 655.21 found: m/z = 655.20 (M+, 100 %)

Synthesis Example 71: Synthesis of compound 153

Synthesis of Intermediate 71A-3

2-bromo-benzo[1,??2-?? b :5,??4-?? b ']??bisbenzofuran, 114g, 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 11.3g, PdCl ₂ (dppf) 0.5g and KOAc 8.8g were placed in a flask, a vacuum environment was created, a nitrogen atmosphere was created, 150ml of DMF was added thereto, and the mixture was heated and stirred at 100° C. for 8 hours. The resulting reactant was poured into 1000 ml of MeOH for crystallization, and the solid obtained by stirring and filtration was dissolved by heating in 500 ml of toluene. The reaction product obtained therefrom was filtered through silica, the solvent was removed so that the residual solution was 100 ml, and crystallized by adding to 1 L of MeOH, followed by drying, to obtain an intermediate 71A-3 (79.4 g).

Synthesis of Intermediate 71A-2

Intermediate 71A-3 1g, 1-iodo-2-nitrobenzene 0.8g, Pd(PPh ₃ ) ₄ 0.3g, and K ₂ CO ₃ 1g were placed in 20ml of THF / H ₂ O(1:1) and heated to 90℃ for 8 hours. while heating and stirring. The reaction product obtained therefrom was extracted twice using 20 ml of methylene chloride to remove moisture by adding 2 g of MgSO ₄ to the obtained extract, and then purified by silica gel column chromatography to obtain an intermediate 71A-2 (0.85 g).

Synthesis of Intermediate 71A-1

1 g of Intermediate 71A-2 and 2.1 g of PPh ₃ were placed in 15 ml of 1,2-dichlorobenzene, and after heating and stirring for 22 hours, the solvent was distilled off. The residue obtained was purified by silica gel column chromatography, and Intermediate 71A-1 (0.59 g ) was obtained.

Synthesis of compound (71)-153

Intermediate 71A-1 1g, 2-chloro-4,6-diphenylpyrimidine 0.95g, Pd ₂ (dba) ₃ 0.1g, NaOtBu, 0.6g were placed in a flask, vacuum was made, and a nitrogen atmosphere was created, and then tri 0.1 g of (tetra-butyl) phosphine and 15 ml of toluene were added, and the mixture was heated and stirred at 110° C. for 8 hours. The solvent was removed from the obtained reactant under vacuum and purified by silica gel column chromatography to obtain compound (71)-153 (1.41 g). The resulting compound was confirmed by LC-MS.

C ₄₀ H ₂₃ N ₃ O ₂ : M+ 577.19

¹ H NMR (500 MHz, CDCl3): δ, ppm 8.59(d, 1H), 8.25~8.22(m, 2H), 8.17(d, 1H), 8.04~8.02(m, 4H), 7.74~7.73 (m, 2H), 7.53~7.50(m, 1H), 7.45~7.35(m, 9H), 7.32~7.28(m,1H), 7.16~7.13(m,1H), 7.00(s,1H).

Synthesis Example 72: Synthesis of compound (71)-154

Synthesis of Intermediate 71B-4

2,8-dibromodibenzo[b,d]thiophene 1.0g, 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane ) 2.2 g, PdCl ₂ (dppf) 0.2 g, and KOAc 1.7 g were placed in a flask to create a vacuum environment, and a nitrogen atmosphere was created. 10.0 ml of H ₂ O was added to the reaction product obtained therefrom, and the solid obtained by stirring and filtration was washed with 50 ml of MeOH, and the remaining solid was purified by silica gel column chromatography to obtain an intermediate 71B-4 (1.1 g).

Synthesis of Intermediate 71B-3

1g of Intermediate 71B-4, 1.2g of 1-iodo-2-nitrobenzene, 0.3g of Pd(PPh ₃ ) ₄ , and 1.9g of K ₂ CO ₃ were placed in 30ml of THF / H2O(1:1) and heated to 80℃ for 10 hours. It was heated and stirred. The reaction product obtained therefrom was extracted using methylene chloride and MgSO ₄ was added to the obtained extract to remove moisture, and the resulting concentrate was purified by silica gel column chromatography to obtain an intermediate 71B-3 (0.81 g).

Synthesis of Intermediate 71B-2

1 g of Intermediate 71B-3 and 3.1 g of PPh ₃ were placed in 12 ml of 1,2-dichlorobenzene, and after heating and stirring for 24 hours, the solvent was distilled off. The residue obtained was purified by silica gel column chromatography, and Intermediate 71B-2, 0.31 g got

Synthesis of Intermediate 71B-1

1 g of Intermediate 71B-2, 0.6 g of iodobenzene, 0.2 g of Pd ₂ (dba) ₃ , and 0.6 g of NaOtBu were placed in a flask to create a vacuum environment, and then a nitrogen atmosphere was created. Here, 0.1 g of tri(tetra-butyl)phosphine and 15 ml of toluene were added, and the reaction product was heated and stirred at 110° C. for 8 hours. The solvent was removed under vacuum and purified by silica gel column chromatography. Intermediate 71B-1 (0.8 g ) was obtained.

Synthesis of compound (71)-154

1 g of Intermediate 71B-1, 1.1 g of 2-chloro-4,6-diphenylpyrimidine, 0.2 g of Pd ₂ (dba) ₃ , and 0.5 g of NaOtBu were placed in a flask, a vacuum environment was created, and a nitrogen atmosphere was created. 0.1 g of tri(tetra-butyl) phosphine and 15 ml of toluene were added thereto, and the reaction product was heated and stirred at 110° C. for 8 hours. The solvent was removed under vacuum and purified by silica gel column chromatography to compound (71)-154 ( 0.95 g) was obtained. The resulting compound was confirmed by LC-MS.

C ₄₆ H ₂₈ N ₄ S : M+ 668.31

¹ H NMR (300 MHz, CDCl3): δ, ppm 8.90(d, 1H), 8.04(d, 1H), 7.93(d, 1H), 7.85(d, 1H), 7.74 (d, 1H), 7.60(s) , 2H), 7.47 (td, 2H), 7.35-7.11 (m,15H), 7.06-7.00 (m,1H), 6.80 (t, 2H), 6.58 (t, 1H).

Synthesis Example 73: Synthesis of compound (71)-155

After 1 g of Intermediate 71B-1 was added to 11 ml of DMF, 0.2 g of NaH was added, stirred at room temperature for 30 minutes, and 0.9 g of 2-chloro-4,6-diphenyl-1,3,5-triazine was added. The mixture was stirred at room temperature for 8 hours. Methylene chloride was added to the obtained reaction product to dissolve the solid, washed with H ₂ O, and then concentrated by removing water using MgSO ₄ . The resulting concentrate was purified by silica gel column chromatography to obtain compound (71)-155 (1.38 g). The resulting compound was confirmed by LC-MS.

C ₄₅ H ₂₇ N ₅ S : M+ 669.24

¹ H NMR (300 MHz, CDCl3): δ, ppm 8.93(d, 1H), 8.03(d, 1H), 7.92(d, 2H), 7.69(q, 4H), 7.51 (td, 2H), 7.40-7.08 (m, 13H), 7.06 to 7.00 (m, 1H), 6.83 (t, 2H), 6.58 (t, 1H).

Synthesis Example 74: Synthesis of compound (71)-156

1 g of Intermediate 71A-1, 0.81 g of 3-bromo-1,1'-biphenyl, 0.1 g of Pd ₂ (dba) ₃ and 0.6 g of NaOtBu were placed in a flask to create a vacuum environment, and then a nitrogen atmosphere was created. 0.1 g of tri(tetra-butyl) phosphine and 15 ml of toluene were added thereto, and the reaction product was heated and stirred at 110° C. for 12 hours. The solvent was removed under vacuum and purified by silica gel column chromatography to compound (71)-156 (1.18). g) was obtained. The resulting compound was confirmed by LC-MS.

C ₃₆ H ₂₁ NO ₂ : M + 499.18

¹ H NMR (500 MHz, DMSO): δ, ppm 9.33 (s, 1H), 8.30 (d, 1H), 8.23 (d, 1H) 8.17-8.15 (m, 2H) 7.78 (d, 1H), 7.72 (d) , 1H), 7.64~7.36(m, 13H), 7.29~7.26(m, 1H)

Synthesis Example 75: Synthesis of compound (71)-157

1 g of Intermediate 71B-2, 1.6 g of iodobenzene, 0.2 g of Pd ₂ (dba) ₃ and NaOtBu, 1.01 g were placed in a flask to create a vacuum environment, and then a nitrogen atmosphere was created. 0.1 g of tri(tetra-butyl) phosphine and 15 ml of toluene were added thereto, and the reaction product was stirred for 8 hours at 110 ° C. The solvent was removed under vacuum and purified by silica gel column chromatography to compound (71)-157 ( 0.4 g) was obtained. The resulting compound was confirmed by LC-MS.

C ₃₆ H ₂₂ N ₂ S : M+ 514.54

¹ H NMR (300 MHz, CDCl3): δ, ppm 8.20-8.15 (m, 2H), 8.01 (d, 1H), 7.96-7.92 (m, 2H), 7.87 (d, 1H), 7.63 (d, 1H) , 7.51~7.28(m, 10H), 7.20~7.14(m, 2H), 7.10~7.04(m, 2H), 6.82~6.76(m, 1H)

Synthesis Example 81: Synthesis of compound (81)-290

Synthesis of intermediate (81)1-1

34.4 g (204.22 mmol) of 7-chlorobenzothiophene was dissolved in 680 mL of dichloromethane, and then 81.6 g (510.56 mmol) of bromine was slowly added dropwise, followed by stirring for 20 hours. The reaction product obtained therefrom was poured into an aqueous sodium thiosulfate solution to terminate the reaction, the organic layer was separated, the solvent was distilled under reduced pressure, and column separation was performed to obtain 45 g (68%) of Intermediate (81)1-1.

Synthesis of intermediate (81)1-2

42.4 g (129.87 mmol) of 2,3-bromo-7-chlorobenzothiophene (intermediate 1-1), 39.6 g (324.67 mmol) of phenylboronic acid, 53.8 g (389.60 mmol) of potassium carbonate, 7.5 g (6.49 mmol) of tetrakistriphenylphosphine palladium, 500 mL of tetrahydrofuran and 200 mL of distilled water were placed in a reaction vessel and heated at 80° C. for 10 hours. After completion of the reaction, the organic layer was separated, the solvent was distilled under reduced pressure, and column separation was performed to obtain 30 g (72%) of Intermediate (81)1-2.

Synthesis of Intermediate (81)1-3

25.9 g (80.84 mmol) of 2,3-diphenyl-7-chlorobenzothiophene (Intermediate 1-2), 28.74 g (113.17 mmol) of bispinacholatodiboron, 15.87 g (161.67 mmol) of potassium acetate, 1.98 g (2.43 mmol) of palladium diphenylphosphinoferrocene dichloride and 320 mL of toluene were placed in a reaction vessel and heated at 100° C. for 12 hours. The obtained reaction product was filtered, and the resulting solution was distilled under reduced pressure and column separated to obtain 26.4 g (79%) of Intermediate (81)1-3.

Synthesis of Intermediate (81)1-4

101.2 g (245.41 mmol) of the intermediate (81) 1-3, 59.5 g (294.49 mmol) of 2-bromonitobenzene, 67.8 g (490.82 mmol) of potassium carbonate, 14.2 g (12.27 mmol) of tetrakistriphenyl Phosphine palladium, 245 mL of distilled water and 1 L of toluene were placed in a reaction vessel and heated at 100° C. for 8 hours. After separation of the organic layer obtained therefrom, the solvent was distilled under reduced pressure and column separated to obtain 78.4 g (78%) of Intermediate (81)1-4.

Synthesis of intermediate (81)1-5

72.3 g (177.55 mmol) of intermediate (81) 1-4, 139.7 g (532.65 mmol) of triphenylphosphine and 710 mL of ditlorobenzene were heated at 180° C. for 12 hours. The solvent of the reaction product obtained therefrom was distilled under reduced pressure, followed by column separation to obtain 46.7 g (70%) of Intermediate (81)1-5.

Synthesis of compound (81)-290

13.3 g (35.38 mmol) of Intermediate (81) 1-5, 2.83 g (70.75 mmol) of sodium hydride was added to 100 mL of dimethylformamide and stirred for 30 minutes, and then 11.3 g (42.45 mmol) of 2-chloro- 4,6-diphenyl pyrimidine was dissolved in 150 mL of dimethylformamide and added dropwise, followed by stirring for 8 hours. The obtained reaction product was poured into water, and the resulting solid was filtered and recrystallized using chlorobenzene to obtain 15.8 g (74%) of compound (81)-290.

calcd. C ₄₂ H ₂₇ N ₃ S: C, 83.28; H, 4.49; N, 6.94; S, 5.29; found: C, 83.54; H, 4.52; N, 6.90

1H-NMR(300MHz, CDCl3)(ppm) δ= 7.25~7.30(3H, m), 7.42~7.47(7H, m), 7.59~7.67(8H, m), 7.72~7.75(1H, d), 8.88 (1H, s), 8.29 to 8.32 (5H, m), 9.01 to 9.07 (2H, m)

Synthesis Example 82: Synthesis of compound (81)-292

13.26 g (35.32 mmol) of intermediate (81) 1-5, 2.825 (70.64 mmol) of sodium hydride was added to 100 mL of dimethylformamide, stirred for 30 minutes, and then 11.35 g (42.38 mmol) of 2-chloro-4 ,6-diphenyl triazine was dissolved in 150 mL of dimethylformamide and added dropwise, followed by stirring for 8 hours. The reaction product obtained therefrom was poured into water, the resulting solid was filtered, and then recrystallized using chlorobenzene to obtain 17.4 g (81%) of compound (81)-292.

calcd. C ₄₁ H ₂₆ N ₄ S: C, 81.16; H, 4.32; N, 9.23; S, 5.28; found: C, 81.32; H, 4.25; N, 9.33

1H-NMR(300MHz, CDCl3)(ppm) δ= 7.29~7.33(3H, m), 7.43~7.64(15H, m), 7.72~7.75(1H, d), 8.20~8.23(1H, d), 8.68 ~8.71 (4H, d), 9.13 ~ 9.18 (2H, m)

Synthesis Example 83: Synthesis of compound (81)-434

Synthesis of intermediate (81)2-1

56.9 g (207.57 mmol) of 1-bromo-5-phenylbenzoxazole, 73.8 g (290.60 mmol) of bispinacolatodiborone, 40.75 g (415.14 mmol) of potassium acetate, 5.085 g (6.23 mmol) of palladium Diphenylphosphinoferrocene dichloride and 320 mL of toluene were placed in a reaction vessel and heated at 100° C. for 12 hours. The obtained reaction product was filtered, and the resulting solution was distilled under reduced pressure and column separated to obtain 45.2 g (68%) of the intermediate (81)3-1.

Synthesis of intermediate (81)2-2

42.3 g (131.73 mmol) of the intermediate (81) 2-1, 31.9 g (158.07 mmol) of 2-bromonitobenzene, 36.4 g (263.45 mmol) of potassium carbonate, 7.6 g (6.6 mmol) of tetrakistriphenyl Phosphine palladium, 130 mL of distilled water, and 530 mL of toluene were placed in a reaction vessel and heated at 100° C. for 8 hours. The organic layer obtained therefrom was separated, the solvent was distilled under reduced pressure, and column separation was performed to obtain 28.9 g (69%) of Intermediate (81)2-2.

Synthesis of intermediate (81)2-3

25.87 g (81.8 mmol) of the intermediate (81)2-2, 64.37 g (245.41 mmol) of triphenylphosphine and 330 mL of dichlorobenzene were heated at 180° C. for 12 hours. The solvent of the obtained reaction product was distilled under reduced pressure, followed by column separation to obtain 28.2 g (85%) of Intermediate (81)2-3.

Synthesis of compound (81)-434

11.84 g (41.64 mmol) of Intermediate (81) 2-3, 2.5 g (62.46 mmol) of sodium hydride was added to 100 mL of dimethylformamide and stirred for 30 minutes, and then 13.3 g (49.97 mmol) of 2-chloro- 4,6-diphenyl pyrimidine was dissolved in 150 mL of dimethylformamide and added dropwise, followed by stirring for 8 hours. The obtained reaction product was poured into water, and the resulting solid was filtered and recrystallized using chlorobenzene to obtain 16.4 g (77%) of compound (81)-434.

calcd. C ₃₅ H ₂₂ N ₄ O: C, 81.69; H, 4.31; N, 10.89; O, 3.11; found: C, 81.82; H, 4.29; N, 10.76

1H-NMR(300MHz, CDCl3)(ppm) δ=7.54~7.56(10H, m), 7.84~7.87(1H, d), 7.94(1H, s), 8.24~8.28(4H, m), 8.36~8.42 (3H, m), 8.93~8.99 (2H, m)

Synthesis Example 84: Synthesis of compound (81)-436

11.82 g (41.56 mmol) of Intermediate (81) 2-3, 2.49 g (62.35 mmol) of sodium hydride was added to 100 mL of dimethylformamide, stirred for 30 minutes, and then 13.35 g (49.88 mmol) of 2-chloro- 4,6-diphenyl triazine was dissolved in 150 mL of dimethylformamide and added dropwise, followed by stirring for 8 hours. The reaction product obtained therefrom was poured into water, and the resulting solid was filtered and recrystallized using chlorobenzene to obtain 18.3 g (85%) of compound (81)-436.

calcd. C ₃₄ H ₂₁ N ₅ O: C, 79.21; H, 4.11; N, 13.58; O, 3.10; found: C, 79.34; H, 4.13; N, 13.45

1H-NMR(300MHz, CDCl3)(ppm) δ=7.56~7.73(10H, m), 7.96~7.99(1H, d), 8.41~8.46(3H, m), 8.77~8.80(4H, m), 9.18 ~9.26 (2H, m)

Synthesis Example 85: Synthesis of compound (81)-438

12,03 g (42.32 mmol) of intermediate (81)2-3, 19.67 g (50.79 mmol) of 2-(3-bromophenyl)-4,6-diphenylpyrimidine, 1.217 g (2.12 mmol) of bis Dibenzylideneacetone palladium, 6.102 g (63.49 mmol) of sodium-tert-butoxide, 4.107 g (8.46 mmol) of tri-tert-butylphosphine (50%-toluene) and 170 mL of toluene were placed in a reaction vessel and nitrogen The mixture was stirred at 110° C. for 12 hours under airflow. After completion of the reaction, the reaction solution was filtered and recrystallized from chlorobenzene to obtain 17.4 g (70%) of compound (81)-438.

calcd. C ₄₁ H ₂₆ N ₄ O: C, 83.37; H, 4.44; N, 9.49; O, 2.71; found: C, 83.41; H, 4.32; N, 9.42

1H-NMR(300MHz, CDCl3)(ppm) δ= 7.45~7.65(13H, m), 7.74~7.77(1H, m), 7.81~7.86(2H, m), 8.10(1H, s), 8.27~8.31 (4H, m), 8.41 to 8.45 (2H, m), 8.51 to 8.54 (1H, m), 8.89 to 8.93 (1H, m), 8.97 to 8.98 (1H, m)

Synthesis Example 86: Synthesis of compound (81)-440

16.02 g (56.43 mmol) of intermediate (81)2-3, 26.25 g (67.34 mmol) of 2-(3-bromophenyl)-4,6-diphenyltriazine, 1.620 g (2.82 mmol) of bisdi Benzylideneacetone palladium, 8.122 g (84.51 mmol) of sodium-tert-butoxide, 5.47 g (11.27 mmol) of tri-tert-butylphosphine (50%-toluene) and 225 mL of toluene were placed in a reaction vessel and nitrogen stream and stirred at 110 °C for 12 hours. After completion of the reaction, the reaction solution was filtered and recrystallized from chlorobenzene to obtain 22.8 g (68%) of compound (81)-440.

calcd. C ₄₀ H ₂₅ N ₅ O: C, 81.20; H, 4.26; N, 11.84; O, 2.70; found: C, 81.14; H, 4.28; N, 11.81

1H-NMR(300MHz, CDCl3)(ppm) δ= 7.42~7.63(13H, m), 7.80~7.88(3H, m), 8.38~8.42(2H, m), 8.49~8.52(1H, m), 8.73 ~8.77(4H, m), 8.91~8.97(1H, m), 9.00(1H, s)

Synthesis Example 91: Synthesis of compound (91)-82

Intermediate 91A 20g (50.215 mmol), Intermediate 91B 24.6g (55.236) and tetrakis(triphenylphosphine)palladium(0)(tetrakis(triphenylphosphine)palladium(0)) 2.9g (2.510 mmol) and potassium carbonate (potassium) carbonate) 19.8 g (143.6 mmol) was suspended in 150/150/150 mL of THF/Toluene/distilled water and stirred under reflux for 18 hours. After completion of the reaction, the precipitate was poured slowly into 2L of methanol, filtered, washed with methanol and distilled water, and recrystallized using a dichlorobenzene solution to obtain 21.30 g (yield 67%) of compound (91)-82.

¹ H-NMR (600 MHz, CDCl3): 7.88 (d, 2H); 7.68 (m, 4H); 7.61 (m, 8H); 7.46 (td, 2H); 7.39 (m, 6H); 7.00(t, 4H); 6.62 (m, 6H)

Synthesis Example 92: Synthesis of compound (91)-84

Intermediate 91C 20 g (42.159 mmol), Intermediate 91D 24.18 g (46.375 mmol), tetrakis (triphenylphosphine) -palladium (0) (tetrakis (triphenylphosphine) palladium (0)) 2.436 g (2.108 mmol) and potassium carbonate ( potassium carbonate) 16.67 g (120.6 mmol) was suspended in THF/Toluene/distilled water 150/150/150 mL and stirred under reflux for 18 hours. After completion of the reaction, the resulting precipitate was slowly poured into 2L of methanol, filtered, washed with methanol and distilled water, and recrystallized using a dichlorobenzene solution to obtain 19.80 g (yield 60%) of compound (91)-84.

¹ H-NMR (600 MHz, CDCl3): 7.91 (d, 2H); 7.71 (td, 4H); 7.65 (m, 8H); 7.51 (td, 2H); 7.43 (m, 10H); 7.33(t, 4H); 7.26(s, 4H); 7.19(t, 2H); 6.73 (d, 4H)

Synthesis Example 93: Synthesis of compound (91)-88

Using the same method as in Synthesis Example 3, compound (91)- 88 17.20 g (yield 52%) were obtained.

¹ H-NMR (600 MHz, CDCl 3 ): 7.89 (m, 4H); 7.68 (m, 16H); 7.42 (m, 10H); 7.03(q, 4H); 6.68 (m, 6H)

Synthesis Example 94: Synthesis of compound (91)-11

Intermediate 91B 20 g (44.907 mmol), Intermediate 91G 19.179 g (49.398), [tetrakis (triphenylphosphine) -palladium (0) (tetrakis (triphenylphosphine) palladium (0)) 2.595 g (2.245 mmol) and potassium carbonate ( potassium carbonate) 17.751 g (128.4 mol) was suspended in THF/Toluene/distilled water 150/150/150 mL and stirred under reflux for 18 hours. After completion of the reaction, the resulting precipitate was poured slowly into 2L of methanol, filtered, washed with methanol and distilled water, purified by column chromatography (MC:Hx=1:4), and recrystallized with toluene to form a white solid compound (91) -11 21.0 g (yield 75%) was obtained.

¹ H-NMR (300 MHz, CDCl3): 8.84 (s, 1H), 7.75 (dd, 4H), 8.61 (d, 1H), 7.60 (m, 16H), 7.43 (m, 6H), 6.72 (d, 2H) )

Synthesis Example 101: Synthesis of compound (101)-1

<Scheme 1>

In a 500 mL round flask, 12.0 g (42.9 mmol) of intermediate 101A, 16 g (51.5 mmol) of 2-bromo-4,6-diphenylpyrimidine, 8.3 g (85.9 mmol) of sodium t-butoxide, Pd (dba) ₂ (Bis(dibenzylideneacetone) palladium(0)) 2.5 g (4.3 mmol), 4.1 mL of tri-t-butylphosphine (50% in toluene) was added to 200 mL of xylene, and heated under a nitrogen stream for 15 hours to reflux. did. The resulting mixture was added to 1000 mL of methanol, the crystallized solid was filtered, dissolved in dichlorobenzene, filtered through silica gel/celite, and an appropriate amount of the organic solvent was removed, followed by recrystallization with methanol to compound (101)-1 ( 14.2 g, yield of 65%). The results of elemental analysis of the produced compound (101)-1 are as follows.

calcd. C ₃₂ H ₁₉ N ₃ S ₂ : C, 75.41; H, 3.76; N, 8.25; S, 12.58; found: C, 75.38; H, 3.74; N, 8.22; S, 12.57

Synthesis Example 102: Synthesis of compound (101)-2

<Scheme 2>

In a 1000 mL flask, 15.0 g (31.2 mmol) of intermediate 101B, 10.7 g (34.3 mmol) of 2-bromo-4,6-diphenylpyrimidine, 8.6 g (62.3 mmol) of potassium carbonate, Pd(PPh ₃ ) ₄ (Tetrakis) (triphenylphosphine) palladium(0)) 1.8 g (1.6 mmol) was added to 350 mL of toluene, 150 mL of water, and 150 mL of ethanol, and then heated to reflux under a nitrogen stream for 6 hours. The resulting mixture was added to 1500 mL of methanol, the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, and an appropriate amount of the organic solvent was removed, followed by recrystallization with methanol to compound (101)-2 ( 11.3 g, yield of 62%). The result of elemental analysis of the produced compound (101)-2 is as follows.

calcd. C ₃₈ H ₂₃ N ₃ S ₂ : C, 77.92; H, 3.96; N, 7.17; S, 10.95; found: C, 77.88; H, 3.97; N, 7.18; S, 10.93

Synthesis Example 103: Synthesis of compound (101)-3

<Scheme 3>

In a 1000 mL flask, 15.5 g (32.2 mmol) of intermediate 101C, 11.0 g (35.4 mmol) of 2-bromo-4,6-diphenylpyrimidine, 8.9 g (64.4 mmol) of potassium carbonate, Pd(PPh ₃ ) ₄ (Tetrakis) (triphenylphosphine) palladium(0)) 1.9 g (1.6 mmol) was added to 350 mL of toluene, 150 mL of water, and 150 mL of ethanol, and then heated to reflux under a nitrogen stream for 6 hours. The resulting mixture was added to 1500 mL of methanol and the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, and an appropriate amount of organic solvent was removed, followed by recrystallization with methanol to compound (101)-3 ( 12.1 g, yield of 64%). The results of elemental analysis of the produced compound (101)-3 are as follows.

calcd. C ₃₈ H ₂₃ N ₃ S ₂ : C, 77.92; H, 3.96; N, 7.17; S, 10.95; found: C, 77.91; H, 3.98; N, 7.16; S, 10.94

Synthesis Example 104: Synthesis of compound (101)-4

<Scheme 4>

In a 500 mL round flask, 13.0 g (46.2 mmol) of intermediate 101D, 17.2 g (55.4 mmol) of 2-bromo-4,6-diphenylpyrimidine, 8.9 g (92.4 mmol) of sodium t-butoxide, Pd (dba) ₂ 2.7 g (4.6 mmol), 3.7 mL of tri-t-butylphosphine (50% in toluene) were placed in 230 mL of xylene, and heated to reflux under a nitrogen stream for 15 hours. The resulting mixture was added to 1000 mL of methanol, the crystallized solid was filtered, dissolved in dichlorobenzene, filtered through silica gel/celite, and an appropriate amount of organic solvent was removed, followed by recrystallization with methanol to compound (101)-4 ( 14.1 g, yield of 60%). Elemental analysis results and NMR analysis results of the resulting compound (101)-4 are as follows.

calcd. C ₃₂ H ₁₉ N ₃ S ₂ : C, 75.41; H, 3.76; N, 8.25; S, 12.58; C, 75.39; H, 3.75; N, 8.26; S, 12.57

300 MHz (CDCl ₃ , ppm): 8.65 (dd, 1H), 8.16 (s, 1H), 8.07 (m, 4H), 7.80 (d, 1H), 7.75 (dd, 1H), 7.34~7.49 (m, 8H), 7.14 (m, 2H), 6.85 (t, 1H)

Synthesis Example 105: Synthesis of compound (101)-5

<Scheme 5>

In a 1000 mL flask, 17.0 g (35.3 mmol) of intermediate 101E, 12.1 g (38.8 mmol) of 2-bromo-4,6-diphenylpyrimidine, 9.8 g (70.6 mmol) of potassium carbonate, Pd(PPh ₃ ) ₄ (Tetrakis) (triphenylphosphine) palladium(0)) 2.0 g (1.8 mmol) was added to 350 mL of toluene, 150 mL of water, and 150 mL of ethanol, and then heated to reflux under a nitrogen stream for 6 hours. The resulting mixture was added to 1500 mL of methanol, the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, and an appropriate amount of organic solvent was removed, followed by recrystallization with methanol to compound (101)-5 ( 12.2 g, yield of 59%). The result of elemental analysis of the produced compound (101)-5 is as follows.

calcd. C ₃₈ H ₂₃ N ₃ S ₂ : C, 77.92; H, 3.96; N, 7.17; S, 10.95; found: C, 77.93; H, 3.95; N, 7.16; S, 10.96

Synthesis Example 106: Synthesis of compound (101)-6

<Scheme 6>

In a 1000 mL flask, 17.9 g (37.2 mmol) of compound 101F, 13.9 g (44.6 mmol) of 2-bromo-4,6-diphenylpyrimidine, 10.3 g (74.4 mmol) of potassium carbonate, Pd(PPh ₃ ) ₄ (Tetrakis) (triphenylphosphine) palladium(0)) 3.1 g (1.9 mmol) was added to 350 mL of toluene, 150 mL of water, and 150 mL of ethanol, and then heated to reflux under a nitrogen stream for 6 hours. The resulting mixture was added to 1500 mL of methanol and the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, and an appropriate amount of organic solvent was removed, followed by recrystallization with methanol to compound (101)-6 ( 14.9 g, 68% yield) were obtained. Elemental analysis results and NMR analysis results of the resulting compound (101)-6 are as follows.

calcd. C ₃₈ H ₂₃ N ₃ S ₂ : C, 77.92; H, 3.96; N, 7.17; S, 10.95; found: C, 77.90; H, 3.95; N, 7.18; S, 10.94

300 MHz (CDCl ₃ , ppm): 8.46 (dd, 1H), 8.18 (m, 4H), 7.94 (s, 1H), 7.92 (d, 1H), 7.79 (dd, 1H), 7.61 (m, 7H) , 7.55 (m, 2H), 7.35 (dd, 1H), 7.27 (m, 2H), 7.16 (d, 1H), 7.13 (d, 1H), 6.68 (t, 1H)

Synthesis Example 107: Synthesis of compound (101)-7

<Scheme 7>

In a 500 mL round flask, 12.0 g (43.9 mmol) of intermediate 101G, 16.4 g (52.7 mmol) of 2-bromo-4,6-diphenylpyrimidine, 8.4 g (87.8 mmol) of sodium t-butoxide, Pd (dba) ₂ 4.0 g (4.4 mmol), 4.3 mL of tri-t-butylphosphine (50% in toluene) were placed in 250 mL of xylene, and heated to reflux under a nitrogen stream for 15 hours. The resulting mixture was added to 1000 mL of methanol, the crystallized solid was filtered, dissolved in dichlorobenzene, filtered through silica gel/celite, and an appropriate amount of organic solvent was removed, followed by recrystallization with methanol to compound (101)-7 ( 12.2 g, yield of 55%). The result of elemental analysis of the produced compound (101)-7 is as follows.

calcd. C ₃₅ H ₂₅ N ₃ O: C, 83.48; H, 5.00; N, 8.34; O, 3.18; found: C, 83.45; H, 5.02; N, 8.33; O, 3.19

Synthesis Example 108: Synthesis of compound (101)-8

<Scheme 8>

In a 1000 mL flask, 16.5 g (34.7 mmol) of intermediate 101H, 11.9 g (38.2 mmol) of 2-bromo-4,6-diphenylpyrimidine, 9.6 g (69.4 mmol) of potassium carbonate, Pd(PPh ₃ ) ₄ (Tetrakis) (triphenylphosphine) palladium(0)) 2.0 g (1.7 mmol) was added to 350 mL of toluene, 150 mL of water, and 150 mL of ethanol, and then heated to reflux under a nitrogen stream for 6 hours. The resulting mixture was added to 1500 mL of methanol, the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, and an appropriate amount of organic solvent was removed, followed by recrystallization with methanol to compound (101)-8 ( 12.3 g, yield of 61%). The result of elemental analysis of the produced compound (101)-8 is as follows.

calcd. C ₄₁ H ₂₉ N ₃ O: C, 84.95; H, 5.04; N, 7.25; O, 2.76; found: C, 84.92; H, 5.02; N, 7.26; O, 2.79

Synthesis Example 109: Synthesis of compound (101)-9

<Scheme 9>

In a 1000 mL flask, 18.0 g (37.2 mmol) of compound 101I, 13.0 g (41.7 mmol) of 2-bromo-4,6-diphenylpyrimidine, 10.5 g (75.7 mmol) of potassium carbonate, Pd(PPh ₃ ) ₄ (Tetrakis) (triphenylphosphine) palladium(0)) 2.2 g (1.9 mmol) was added to 350 mL of toluene, 150 mL of water, and 150 mL of ethanol, and then heated to reflux under a nitrogen stream for 6 hours. The resulting mixture was added to 1500 mL of methanol, the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, and an appropriate amount of organic solvent was removed, followed by recrystallization with methanol to compound (101)-9 ( 12.7 g, yield of 58%). The results of elemental analysis of the produced compound (101)-9 are as follows.

calcd. C ₄₁ H ₂₉ N ₃ O: C, 84.95; H, 5.04; N, 7.25; O, 2.76; found: C, 84.94; H, 5.02; N, 7.27; O, 2.78

Synthesis Example 110: Synthesis of compound (101)-10

<Scheme 10>

In a 500 mL round flask, 13.5 g (49.4 mmol) of intermediate 101J, 18.4 g (59.3 mmol) of 2-bromo-4,6-diphenylpyrimidine, 9.5 g (98.8 mmol) of sodium t-butoxide, Pd (dba) ₂ 4.5 g (4.9 mmol) and 4.8 mL of tri-t-butylphosphine (50% in toluene) were placed in 300 mL of xylene, and heated to reflux under a nitrogen stream for 15 hours. The resulting mixture was added to 1000 mL of methanol, the crystallized solid was filtered, dissolved in dichlorobenzene, filtered through silica gel/celite, and an appropriate amount of organic solvent was removed, followed by recrystallization with methanol to compound (101)-10 ( 14.4 g, yield of 58%). Elemental analysis results of the produced compound (101)-10 are as follows.

calcd. C ₃₅ H ₂₅ N ₃ O: C, 83.48; H, 5.00; N, 8.34; O, 3.18; found: C, 83.49; H, 5.01; N, 8.32; O, 3.16

Synthesis Example 111A: Synthesis of compound (101)-11

<Scheme 11>

In a 1000 mL flask, 15.0 g (31.6 mmol) of intermediate 101K, 10.8 g (34.7 mmol) of 2-bromo-4,6-diphenylpyrimidine, 8.7 g (63.1 mmol) of potassium carbonate, Pd(PPh ₃ ) ₄ (Tetrakis) (triphenylphosphine) palladium(0)) 1.8 g (1.6 mmol) was added to 350 mL of toluene, 150 mL of water, and 150 mL of ethanol, and then heated to reflux under a nitrogen stream for 6 hours. The resulting mixture was added to 1500 mL of methanol, the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, and an appropriate amount of the organic solvent was removed, followed by recrystallization with methanol to compound (101)-11 ( 11.5 g, 63% yield). The result of elemental analysis of the produced compound (101)-11 is as follows.

calcd. C ₄₁ H ₂₉ N ₃ O: C, 84.95; H, 5.04; N, 7.25; O, 2.76; found: C, 84.96; H, 5.01; N, 7.27; O, 2.77

Synthesis Example 112A: Synthesis of compound (101)-12

<Scheme 12>

In a 1000 mL flask, 15.0 g (31.6 mmol) of compound 101L, 10.8 g (34.7 mmol) of 2-bromo-4,6-diphenylpyrimidine, 8.7 g (63.1 mmol) of potassium carbonate, Pd(PPh ₃ ) ₄ (Tetrakis) (triphenylphosphine) palladium(0)) 1.8 g (1.6 mmol) was added to 350 mL of toluene, 150 mL of water, and 150 mL of ethanol, and then heated to reflux under a nitrogen stream for 6 hours. The resulting mixture was added to 1500 mL of methanol and the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, and an appropriate amount of organic solvent was removed, followed by recrystallization with methanol to compound (101)-12 ( 11.3 g, yield of 62%). Elemental analysis results of the produced compound (101)-12 are as follows.

calcd. C ₄₁ H ₂₉ N ₃ O: C, 84.95; H, 5.04; N, 7.25; O, 2.76; found: C, 84.93; H, 5.02; N, 7.26; O, 2.75

Synthesis Example 111: Synthesis of compound (111) A-141

Intermediate 111A 20 g (47.01 mmol) and Intermediate 111B 15.047 g (56.41 mmol) and [tetrakis (triphenylphosphine) palladium (0) (tetrakis (triphenylphosphine) palladium (0)) 2.16 g (2.35 mmol), potassium carbonate (potassium carbonate) 12.995 g (94.02 mmol) was suspended in THF/Toluene/distilled water 100/100/100 mL and stirred under reflux for 18 hours. After completion of the reaction, after the reaction was lowered to room temperature, 300 mL of methanol was added, and after stirring, the precipitate was filtered and washed with methanol and distilled water. After dissolving the solid in toluene in 650 mL, filter the silica. Toluene and monochlorobenzene were dissolved by heating in 220/220 mL mixed solvent conditions. After blowing off about 110 mL of the solvent, the temperature was lowered and recrystallized to obtain 18.0 g (yield 72%) of compound (111) A-141.

< ¹ H-NMR (300 MHz, CDCl 3 ): 8.93 (d, 1 H); 8.44(d, 4H); 8.06 (s, 1H); 7.95 (m, 1H); 7.64 (m, 11H); 7.48(d, 1H); 7.43(d, 1H); 7.38 (m, 1H); 7.30(m, 2H)>

Synthesis Example 112: Synthesis of compound (111) A-143

21.0 g (yield 84%) of compound (111)A-143 was obtained in the same manner as in Synthesis Example 111, except that Intermediate 111C (15.105 g, 56.42 mmol) was used instead of Intermediate 111B.

< ¹ H-NMR (300 MHz, CDCl 3 ): 9.00 (d, 1 H); 8.93 (m, 4H); 8.00 (m, 1H); 7.65 (m, 10H); 7.58(d, 1H); 7.55(d, 1H); 7.45(d, 1H); 7.38 (m, 1H); 7.33(m, 2H)>

Synthesis Example 113: Synthesis of compound (111) A-136

20.5 g (yield 82%) of Compound (111)A-136 was obtained in the same manner as in Synthesis Example 111, except that Intermediate 111D (20 g, 47.01 mmol) was used instead of Intermediate 111A.

< ¹ H-NMR (300 MHz, CDCl 3 ): 8.78 (s, 1 H); 8.70(d, 1H); 8.17 (m, 4H); 8.01(d, 1H); 7.96(s, 1H); 7.85 (m, 1H); 7.74(s, 5H); 7.56 (m, 6H); 7.42(m, 1H); 7.31(m, 2H)>

Synthesis Example 121: Synthesis of compound (121)-5

Intermediate 121A 20g (50.090 mmol) and Intermediate 121B 20.346g (55.099 mmol) and [tetrakis(triphenylphosphine)-palladium(0)(tetrakis(triphenylphosphine)palladium (0)) 5.788g (5.009 mmol), potassium carbonate (potassium carbonate) 19.8 g (143.258 mmol) was suspended in THF/Toluene/distilled water 150/150/150 mL and stirred under reflux for 18 hours. After completion of the reaction, it is slowly poured into 2L of methanol to form a precipitate, filtered, and washed with methanol and distilled water. After drying, dichloromethane (CH2Cl2) was dissolved, and the resultant was separated by silica gel chromatography. Compound (121)-5 15.47 g (yield 55%) was obtained.

< ¹ H-NMR (600 MHz, CDCl 3 ): 8.97 (s, 2H); 8.59 (d, 2H); 8.53 (s, 2H); 8.47 (s, 2H); 8.27 (d, 2H); 8.14 (d, 2H); 7.97(d, 2H); 7.90 (m, 4H); 7.79 (d, 2H); 7.75(d, 8H); 7.67 (m, 10H); 7.54 (m, 8H); 7.46 (m, 6H); 7.35(m, 2H)>

Synthesis Example 122: Synthesis of compound (121)-18

The compound (121)- 18 19.81 g (yield 62%) were obtained.

Synthesis Example 123: Synthesis of compound (121)-151

Compound (121)- using the same method as in Synthesis Example 121, except that 24.539 g (50.090 mmol) of Intermediate 121D (50.090 mmol) was used instead of Intermediate 121B, and recrystallization was performed using dichloromethane instead of silica gel chromatography. 151 16.61 g (yield 52%) were obtained.

Synthesis Example 124: Synthesis of compound (121)-152

Intermediate 121A 20 g (50.090 mmol) and Intermediate 112E 20.594 g (55.099 mmol) and [tetrakis (triphenylphosphine) palladium (0) (tetrakis (triphenylphosphine) palladium (0)) 5.788 g (5.009 mmol), potassium carbonate (potassium carbonate) 19.8 g (143.258 mmol) was suspended in THF/Toluene/distilled water 150/150/150 mL and stirred under reflux for 18 hours. After completion of the reaction, it is slowly poured into 2L of methanol to form a precipitate, filtered, and washed with methanol and distilled water. After drying, it is recrystallized after dissolving in dichloromethane (CH2Cl2). Compound (121)-152 21.08 g (yield 66%) was obtained.

< ¹ H-NMR (300 MHz, CDCl 3 ): 8.97 (s, 2H); 8.59 (d, 2H); 8.51 (s, 2H); 8.13 (d, 2H); 7.95(d, 2H); 7.90 (m, 4H); 7.74 (m, 8H); 7.69 (d, 2H); 7.56 (t, 4H); 7.45(m, 2H)>

Synthesis Example 125: Synthesis of compound (121)-153

16.35 g of compound (121)-153 using the same method as in Synthesis Example 124, except that 20.4 g (50.090 mmol) of Intermediate 121F was used instead of Intermediate 121E, and silica gel chromatography was performed instead of recrystallization using dichloromethane. (yield 58%) was obtained.

Synthesis Example 126: Synthesis of compound (121)-33

20g (61.883 mmol) of Intermediate 121G was used instead of Intermediate 121A, 25.203g (68.071 mmol) of Intermediate 121F was used instead of Intermediate 121E, and silica gel chromatography was used instead of recrystallization using dichloromethane. 16.85 g (yield 56%) of compound (121)-33 was obtained using the same method as 124.

Synthesis Example 127: Synthesis of compound (121)-49

Intermediate 121H 19g (50.904 mmol) and Intermediate 121E 20.677g (55.995 mmol) and [tetrakis(triphenylphosphine)palladium(0)(tetrakis(triphenylphosphine)palladium (0)) 2.545g (2.545 mmol), potassium carbonate (potassium carbonate) 20.121 g (145.586 mmol) was suspended in THF/Toluene/distilled water 150/150/150 mL and stirred under reflux for 18 hours. After completion of the reaction, it is slowly poured into 2L of methanol to form a precipitate, filtered, and washed with methanol and distilled water. After drying, silica gel chromatography was performed under dichloromethane (CH2Cl2) conditions. Compound (121)-49 15.00 g (yield 55%) was obtained.

< ¹ H-NMR (300 MHz, CDCl 3 ): 9.17 (s, 1 H); 8.91(s, 1H); 8.89(s, 1H); 8.50(d, 1H); 8.32(d, 1H); 8.28(d, 1H); 7.94 (d, 1H), 7.81 (t, 2H); 7.71 (m, 5H); 7.64 (m, 5H); 7.57 (m, 2H); 7.55 (m, 1H), 7.46 (d, 2H); 7.35(m, 1H)>

Synthesis Example 128: Synthesis of compound (121)-64

Using the same method as in Synthesis Example 127, except that 21.823g (58.942 mmol) of Intermediate 121F was used instead of Intermediate 121, and silica gel chromatography was performed under dichloromethane (CH ₂ Cl ₂ ) conditions after drying. (121)-64 17.26 g (yield 60%) was obtained.

Synthesis Example 129: Synthesis of compound (121)-70

Intermediate 121I 12.387g (29.471 mmol) was used instead of Intermediate 121B, and after drying, the compound was separated by silica gel chromatography under dichloromethane (CH2Cl2)/Ethyl acetate conditions. (121)-70 11.20 g (yield 71%) was obtained.

Synthesis Example 130: Synthesis of compound (121)-74

Intermediate 121J 20g (53.583 mmol) and Intermediate 121B 21.765g (58.942 mmol) and [tetrakis(triphenylphosphine)-palladium(0)(tetrakis(triphenylphosphine)palladium (0)) 3.096g (2.679 mmol), potassium carbonate (potassium carbonate) 21.180 g (153.248 mmol) was suspended in THF/Toluene/distilled water 150/150/150 mL and stirred under reflux for 18 hours. After completion of the reaction, it is slowly poured into 2L of methanol to form a precipitate, filtered, and washed with methanol and distilled water. After drying, silica gel chromatography was performed under dichloromethane (CH2Cl2)/ethyl acetate conditions. 18.00 g (yield 63%) of compound (121)-74 was obtained.

Synthesis Example 131A: Synthesis of compound (121)-85

20g (53.583 mmol) of Intermediate 121J was used instead of Intermediate 121H, and after drying, the compound was separated by silica gel chromatography under dichloromethane (CH2Cl2)/Ethyl acetate conditions, using the same method as in Synthesis Example 128. (121)-85 18.50 g (yield 64%) was obtained.

Synthesis of Intermediate I-1

[Scheme (131)1]

After dissolving 100 g (326 mmol) of 2-bromotriphenylene in 1 L of dimethylformamide (DMF) in a nitrogen environment, bis (pinacolato) diboron (bis (pinacolato) diboron) ) 99.2 g (391 mmol) and (1,1'-bis (diphenylphosphine) dichloropalladium (II) ((1,1'-bis (diphenylphosphine) ferrocene) dichloropalladium (II)) 2.66 g (3.26 mmol) Then 80 g (815 mmol) of potassium acetate was added, and the mixture was refluxed by heating at 150° C. After completion of the reaction, water was added to the reaction solution, the mixture was filtered, and the mixture was dried in a vacuum oven. was separated and purified by flash column chromatography to obtain 113 g (98%) of Intermediate I-1.

HRMS (70 eV, EI+): m/z calcd for C24H23BO2: 354.1791, found: 354.

Elemental Analysis: C, 81%; H, 7%

Synthesis of Intermediate I-2

[Scheme (131)2]

After dissolving 32.7 g (107 mmol) of 2-bromotriphenylene in a nitrogen environment in 0.3 L of tetrahydrofuran (THF), 3-chlorophenyl boronic acid ) (20 g, 128 mmol) and 1.23 g (1.07 mmol) of tetrakis(triphenylphosphine)palladium were added and stirred. 36.8 g (267 mmol) of potassium carbonate saturated in water was added and heated at 80 °C for 24 hours to reflux. After completion of the reaction, water was added to the reaction solution, extraction was performed with dichloromethane (DCM), and water was removed with anhydrous MgSO 4 , filtered and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain 22.6 g (63%) of Intermediate I-2.

HRMS (70 eV, EI+): m/z calcd for C24H15Cl: 338.0862, found: 338.

Elemental Analysis: C, 85%; H, 5%

Synthesis of Intermediate I-3

[Scheme (131)3]

After dissolving 22.6 g (66.7 mmol) of Intermediate I-2 in 0.3 L of dimethylformamide (DMF) in a nitrogen environment, 25.4 g (100) of bis(pinacolato)diboron mmol) and (1,1'-bis(diphenylphosphine)ferrocene)dichloropalladium(II)((1,1'-bis(diphenylphosphine)ferrocene)dichloropalladium(II)) 0.54 g (0.67 mmol) and potassium acetate (potassium acetate) 16.4 g (167 mmol) was added, and the mixture was heated at 150° C. for 48 hours to reflux. After completion of the reaction, water was added to the reaction solution, the mixture was filtered, and then dried in a vacuum oven. The residue thus obtained was separated and purified by flash column chromatography to obtain 18.6 g (65%) of Intermediate I-3.

HRMS (70 eV, EI+): m/z calcd for C30H27BO2: 430.2104, found: 430.

Elemental Analysis: C, 84%; H, 6%

Synthesis of Intermediate I-4

[Scheme (131)4]

After dissolving 100 g (282 mmol) of the intermediate I-1 in 1 L of tetrahydrofuran (THF) in a nitrogen environment, thereto, 95.9 g of 1-bromo-2-iodobenzene (1-bromo-2-iodobenzene) (339 mmol) and 3.26 g (2.82 mmol) of tetrakis (triphenylphosphine) palladium were added and stirred. 97.4 g (705 mmol) of potassium carbonate saturated in water was added, and the mixture was heated at 80° C. for 53 hours to reflux. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), dried with anhydrous MgSO 4 , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain 95.1 g (88%) of Intermediate I-4.

HRMS (70 eV, EI+): m/z calcd for C24H15Br: 382.0357, found: 382.

Elemental Analysis: C, 75%; H, 4%

Synthesis of Intermediate I-5

[Scheme (131)5]

After dissolving 90 g (235 mmol) of Intermediate I-4 in 0.8 L of dimethylformamide (DMF) in a nitrogen environment, 71.6 g (282 mmol) of bis(pinacolato)diboron) and (1,1'-bis(diphenylphosphine)ferrocene)dichloropalladium(II)((1,1'-bis(diphenylphosphine)ferrocene)dichloropalladium(II)) 1.92 g (2.35 mmol) and potassium acetate 57.7 g (588 mmol) was added and heated at 150 °C for 35 hours to reflux. After completion of the reaction, water was added to the reaction solution, the mixture was filtered, and then dried in a vacuum oven. The residue thus obtained was separated and purified by flash column chromatography to obtain 74.8 g (74%) of Intermediate I-5.

HRMS (70 eV, EI+): m/z calcd for C30H27BO2: 430.2104, found: 430.

Elemental Analysis: C, 84%; H, 6%

Synthesis of Intermediate I-6

[Scheme (131)6]

After dissolving 50 g (116 mmol) of Intermediate I-3 in 0.5 L of tetrahydrofuran (THF) in a nitrogen environment, 39.4 g of 1-bromo-3-iodobenzene (139 mmol) and 1.34 g (1.16 mmol) of tetrakis (triphenylphosphine) palladium were added and stirred. 40.1 g (290 mmol) of potassium carbonate saturated in water was added and heated at 80 °C for 12 hours to reflux. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), dried with anhydrous MgSO 4 , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain 42.6 g (80%) of Intermediate I-6.

HRMS (70 eV, EI+): m/z calcd for C30H19Br: 458.0670, found: 458.

Elemental Analysis: C, 78%; H, 4%

Synthesis of Intermediate I-7

[Scheme (131)7]

After dissolving 40 g (87.1 mmol) of Intermediate I-6 in 0.3 L of dimethylformamide (DMF) in a nitrogen environment, 26.5 g (104 mmol) of bis(pinacolato)diboron) and (1,1'-bis(diphenylphosphine)ferrocene)dichloropalladium(II)((1,1'-bis(diphenylphosphine)ferrocene)dichloropalladium(II)) 0.71 g (0.87 mmol) and potassium acetate 21.4 g (218 mmol) was added and heated at 150 °C for 26 hours to reflux. After completion of the reaction, water was added to the reaction solution, the mixture was filtered, and then dried in a vacuum oven. The residue thus obtained was separated and purified by flash column chromatography to obtain 34 g (77%) of Intermediate I-7.

HRMS (70 eV, EI+): m/z calcd for C36H31BO2: 506.2417, found: 506.

Elemental Analysis: C, 85%; H, 6%

Synthesis of Intermediate I-8

[Scheme (131)8]

After dissolving 70 g (163 mmol) of the intermediate I-5 in 0.6 L of tetrahydrofuran (THF) in a nitrogen environment, 55.2 g of 1-bromo-2-iodobenzene (195 mmol) and 1.88 g (1.63 mmol) of tetrakis (triphenylphosphine) palladium were added and stirred. 56.3 g (408 mmol) of potassium carbonate saturated in water was added and heated at 80 °C for 12 hours to reflux. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), dried with anhydrous MgSO 4 , filtered, and concentrated under reduced pressure. The obtained residue was separated and purified by flash column chromatography to obtain 68.1 g (91%) of Intermediate I-8.

HRMS (70 eV, EI+): m/z calcd for C30H19Br: 458.0670, found: 458.

Elemental Analysis: C, 78%; H, 4%

Synthesis of Intermediate I-9

[Scheme (131)9]

After dissolving 40 g (87.1 mmol) of Intermediate I-8 in 0.3 L of dimethylformamide (DMF) in a nitrogen environment, 26.5 g (104 mmol) of bis(pinacolato)diboron) and (1,1'-bis(diphenylphosphine)ferrocene)dichloropalladium(II)((1,1'-bis(diphenylphosphine)ferrocene)dichloropalladium(II)) 0.71 g (0.87 mmol) and potassium acetate 21.4 g (218 mmol) was added and heated at 150 °C for 23 hours to reflux. After completion of the reaction, water was added to the reaction solution, the mixture was filtered, and then dried in a vacuum oven. The residue thus obtained was separated and purified by flash column chromatography to obtain 30.4 g (69%) of Intermediate I-7.

HRMS (70 eV, EI+): m/z calcd for C36H31BO2: 506.2417, found: 506.

Elemental Analysis: C, 85%; H, 6%

Synthesis of Intermediate I-10

[Scheme (131)10]

After dissolving 30 g (59.2 mmol) of Intermediate I-9 in 0.3 L of tetrahydrofuran (THF) in a nitrogen environment, 1 -bromo-2-iodobenzene (1-bromo-2-iodobenzene) 20.1 g (71.1 mmol) and 0.68 g (0.59 mmol) of tetrakis (triphenylphosphine) palladium were added and stirred. 20.5 g (148 mmol) of potassium carbonate saturated in water was added and heated at 80 °C for 16 hours to reflux. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), dried with anhydrous MgSO 4 , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain 32.4 g (85%) of Intermediate I-10.

HRMS (70 eV, EI+): m/z calcd for C36H23Br: 534.0983, found: 534.

Elemental Analysis: C, 81%; H, 4%

Synthesis of Intermediate I-11

[Scheme (131)11]

After dissolving 30 g (56 mmol) of Intermediate I-10 in 0.3 L of dimethylformamide (DMF) in a nitrogen environment, 17.1 g (67.2 mmol) of bis(pinacolato)diboron) and (1,1'-bis(diphenylphosphine)ferrocene)dichloropalladium(II)((1,1'-bis(diphenylphosphine)ferrocene)dichloropalladium(II)) 0.46 g (0.56 mmol) and 13.7 g potassium acetate (140 mmol) was added and heated at 150 °C for 25 hours to reflux. After completion of the reaction, water was added to the reaction solution, the mixture was filtered, and then dried in a vacuum oven. The residue thus obtained was separated and purified by flash column chromatography to obtain 22.8 g (70%) of Intermediate I-11.

HRMS (70 eV, EI+): m/z calcd for C42H35BO2: 582.2730, found: 582.

Elemental Analysis: C, 87%; H, 6%

Synthesis Example 131: Synthesis of compound A-1

[Scheme (131)12]

After dissolving 20 g (56.5 mmol) of the intermediate 1-1 in 0.2 L of tetrahydrofuran (THF) in a nitrogen environment, thereto, 2-chloro-4,6-diphenyl-1,3,5-triazine (2 -chloro-4,6-diphenyl-1,3,5-triazine) 15.1 g (56.5 mmol) and tetrakis (triphenylphosphine) palladium 0.65 g (0.57 mmol) were added and stirred . 19.5 g (141 mmol) of potassium carbonate saturated in water was added, and the mixture was heated at 80° C. for 20 hours to reflux. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), dried with anhydrous MgSO 4 , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound A-1 (22.1 g, 85%).

HRMS (70 eV, EI+): m/z calcd for C33H21N3: 459.1735, found: 459.

Elemental Analysis: C, 86%; H, 5%

Synthesis Example 132: Synthesis of compound A-13

[Scheme (131)13]

After dissolving 20 g (46.5 mmol) of Intermediate 1-3 in 0.2 L of tetrahydrofuran (THF) in a nitrogen environment, thereto, 4-chloro-2,6-diphenylpyridine (4-chloro-2,6-diphenylpyridine) ) 12.4 g (46.5 mmol) and 0.54 g (0.47 mmol) of tetrakis (triphenylphosphine) palladium were added and stirred. 16.1 g (116 mmol) of potassium carbonate saturated in water was added, and the mixture was heated at 80 °C for 17 hours to reflux. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), dried with anhydrous MgSO 4 , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound A-13 (18.9 g, 76 %).

HRMS (70 eV, EI+): m/z calcd for C41H27N: 533.2143, found: 533.

Elemental Analysis: C, 92%; H, 5%

Synthesis Example 133: Synthesis of compound A-14

[Scheme (131)14]

After dissolving 20 g (46.5 mmol) of Intermediate 1-3 in 0.2 L of tetrakishydrofuran (THF) in a nitrogen environment, 2-chloro-4,6-diphenylpyrimidine (2-chloro-4,6 -diphenylpyrimidine) 12.4 g (46.5 mmol) and tetrakis (triphenylphosphine) palladium 0.54 g (0.47 mmol) were added and stirred. 16.1 g (116 mmol) of potassium carbonate saturated in water was added and heated at 80 °C for 15 hours to reflux. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), dried with anhydrous MgSO 4 , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain 20.4 g (82%) of Compound A-14.

HRMS (70 eV, EI+): m/z calcd for C40H26N2: 534.2096, found: 534.

Elemental Analysis: C, 90%; H, 5%

Synthesis Example 134: Synthesis of compound A-15

[Scheme (131)15]

After dissolving 20 g (46.5 mmol) of Intermediate 1-3 in 0.2 L of tetrahydrofuran (THF) in a nitrogen environment, 2-chloro-4,6-diphenyl-1,3,5-triazine (2 -chloro-4,6-diphenyl-1,3,5-triazine) 12.4 g (46.5 mmol) and tetrakis (triphenylphosphine) palladium 0.54 g (0.47 mmol) were added and stirred . 16.1 g (116 mmol) of potassium carbonate saturated in water was added, and the mixture was heated at 80 °C for 20 hours to reflux. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), dried with anhydrous MgSO 4 , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound A-15 (21.2 g, 85%).

HRMS (70 eV, EI+): m/z calcd for C39H25N3: 535.2048, found: 535.

Elemental Analysis: C, 87%; H, 5%

Synthesis Example 135: Synthesis of compound A-24

[Scheme (131)16]

After dissolving 20 g (46.5 mmol) of Intermediate 1-5 in 0.2 L of tetrakishydrofuran (THF) in a nitrogen environment, 2-chloro-4,6-diphenyl-1,3,5-triazine ( 2-chloro-4,6-diphenyl-1,3,5-triazine) 12.4 g (46.5 mmol) and tetrakis (triphenylphosphine) palladium 0.54 g (0.47 mmol) were added and stirred did it 16.1 g (116 mmol) of potassium carbonate saturated in water was added and heated at 80 °C for 27 hours to reflux. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), dried with anhydrous MgSO 4 , filtered, and concentrated under reduced pressure. The obtained residue was separated and purified by flash column chromatography to obtain Compound A-24 (19.7 g, 79%).

HRMS (70 eV, EI+): m/z calcd for C39H25N3: 535.2048, found: 535.

Elemental Analysis: C, 87%; H, 5%

Synthesis Example 136: Synthesis of compound A-33

[Scheme (131)17]

After dissolving 20 g (39.5 mmol) of Intermediate 1-7 in 0.2 L of tetrahydrofuran (THF) in a nitrogen environment, 2-chloro-4,6-diphenyl-1,3,5-triazine (2 -chloro-4,6-diphenyl-1,3,5-triazine) 10.6 g (39.5 mmol) and tetrakis (triphenylphosphine) palladium 0.46 g (0.4 mmol) were added and stirred . 13.6 g (98.8 mmol) of potassium carbonate saturated in water was added, and the mixture was heated at 80° C. for 23 hours to reflux. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), dried with anhydrous MgSO 4 , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound A-33 (17.9 g, 74%).

HRMS (70 eV, EI+): m/z calcd for C45H29N3: 611.2361, found: 611.

Elemental Analysis: C, 88%; H, 5%

Synthesis Example 137: Synthesis of compound A-69

[Scheme (131)18]

After dissolving 20 g (39.5 mmol) of Intermediate 1-9 in 0.2 L of tetrahydrofuran (THF) in a nitrogen environment, 2-chloro-4,6-diphenyl-1,3,5-triazine (2 -chloro-4,6-diphenyl-1,3,5-triazine) 10.6 g (39.5 mmol) and tetrakis (triphenylphosphine) palladium 0.46 g (0.4 mmol) were added and stirred . 13.6 g (98.8 mmol) of potassium carbonate saturated in water was added, and the mixture was heated at 80° C. for 32 hours to reflux. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), dried with anhydrous MgSO 4 , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound A-69 (15.2 g, 63%).

HRMS (70 eV, EI+): m/z calcd for C45H29N3: 611.2361, found: 611.

Elemental Analysis: C, 88%; H, 5%

Synthesis Example 138: Synthesis of compound A-87

[Scheme (131)19]

After dissolving 20 g (34.3 mmol) of Intermediate 1-11 in 0.15 L of tetrahydrofuran (THF) in a nitrogen environment, 2-chloro-4,6-diphenyl-1,3,5-triazine (2 -chloro-4,6-diphenyl-1,3,5-triazine) 9.19 g (34.3 mmol) and tetrakis (triphenylphosphine) palladium 0.4 g (0.34 mmol) were added and stirred . 11.9 g (85.8 mmol) of potassium carbonate saturated in water was added, and the mixture was heated at 80° C. for 29 hours to reflux. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), dried with anhydrous MgSO 4 , filtered, and concentrated under reduced pressure. The obtained residue was separated and purified by flash column chromatography to obtain Compound A-87 (16.3 g, 69%).

HRMS (70 eV, EI+): m/z calcd for C51H33N3: 687.2674, found: 687.

Elemental Analysis: C, 89%; H, 5%

Synthesis Example 139: Synthesis of compound C-10

[Scheme (131)20]

10 g (34.83 mmol) of phenylcarbazolyl boronic acid, 11.77 g (38.31 mmol) of the intermediate 141-2 and 14.44 g (104.49 mmol) of potassium carbonate, tetrakis- (triphenylphosphine) palladium (0) ) 0.80 g (0.7 mmmol) was suspended in 140 ml of toluene and 50 ml of distilled water and stirred under reflux for 12 hours. Then, extraction is performed with dichloromethane and distilled water, and the organic layer is filtered through silica gel. Then, the organic solution was removed and the product solid was recrystallized from dichloromethane and n-hexane by silica gel column with hexane:dichloromethane = 7:3 (v/v) to obtain 14.4 g of compound C-10 (yield: 88%). .

HRMS (70 eV, EI+): m/z calcd for C36H23N: 469.18, found: 469

Elemental Analysis: C, 92%; H, 5%

Synthesis Example 140: Synthesis of compound B-10

[Scheme (131)21]

Synthesis of compound (J)

After mixing 26.96 g (81.4 mmol) of N-phenyl carbazole-3-boronic acid pinacholate, 23.96 g (97.36 mmol) of 3-bromocarbazole, 230 mL of tetrahydrofuran and 100 ml of 2M-potassium carbonate aqueous solution, nitrogen It was heated to reflux under airflow for 12 hours. After completion of the reaction, the solids formed by pouring methanol into the reactants are filtered, the solids are again dissolved in chlorobenzene, activated carbon and anhydrous magnesium sulfate are added thereto, and the mixture is stirred. The solution was filtered and recrystallized using chlorobenzene and methanol to obtain 22.6 g of compound (J) (yield: 68%).

HRMS (70 eV, EI+): m/z calcd for C30H20N2: 408.16, found: 408

Elemental Analysis: C, 88%; H, 5%

Synthesis of compound B-10

22.42 g (54.88 mmol) of compound (J), 20.43 g (65.85 mmol) of 2-bromo-4,6-difetylpyridine and 7.92 g (82.32 mmol) of sodium tert-butoxy were dissolved in 400 ml of toluene, followed by palladium diben 1.65 g (1.65 mmol) of zylidenamine and 1.78 g (4.39 mmol) of tert-butyl are added dropwise. The reaction solution was heated and stirred at 110°C for 12 hours under a nitrogen stream. After completion of the reaction, methanol is poured into the reaction product to filter the solid, and then the solid is dissolved again in chlorobenzene, activated carbon and anhydrous magnesium sulfate are added thereto, and the mixture is stirred. The solution was filtered and recrystallized using chlorobenzene and methanol to obtain 28.10 g of Compound B-10 (yield: 80%).

HRMS (70 eV, EI+): m/z calcd for C47H31N3: 637.25, found: 637

Elemental Analysis: C, 89%; H, 5%

Synthesis Example 141A: Synthesis of compound B-31

[Scheme (131)22]

phenylcarbazolyl bromide 9.97 g (30.95 mmol), phenylcarbazolylboronic acid 9.78 g (34.05 mmol) and potassium carbonate 12.83 g (92.86 mmol), tetrakis-(triphenylphosphine)palladium (0) 1.07 g (0.93 mmmol) was suspended in 120 ml of toluene and 50 ml of distilled water and stirred under reflux for 12 hours. Then, extraction is performed with dichloromethane and distilled water, and the organic layer is filtered through silica gel. Then, the organic solution was removed, and the product solid was recrystallized from dichloromethane and n-hexane to obtain 13.8 g of Compound B-31 (yield: 92%).

HRMS (70 eV, EI+): m/z calcd for C36H24N2: 484.19, found: 484

Elemental Analysis: C, 89%; H, 5%

Compound 142A: Synthesis of Compound B-34

[Scheme (131)23]

14.62 g (30.95 mmol) of triphenylcarbazolyl bromide, 9.78 g (34.05 mmol) of phenylcarbazolylboronic acid and 12.83 g (92.86 mmol) of potassium carbonate, tetrakis-(triphenylphosphine) 1.07 g (0.93 mmmol) of palladium (0) was suspended in 120 ml of toluene and 50 ml of distilled water and stirred under reflux for 12 hours. Then, extraction is performed with dichloromethane and distilled water, and the organic layer is filtered through silica gel. Then, the organic solution was removed and the product solid was recrystallized from dichloromethane and n-hexane to obtain 16.7 g of Compound B-34 (yield: 85%).

HRMS (70 eV, EI+): m/z calcd for C47H29N2: 621.23, found: 621

Elemental Analysis: C, 91%; H, 5%

Synthesis Example 143A: Synthesis of compound B-43

[Scheme (131)24]

Biphenylcarbazolyl bromide 12.33 g (30.95 mmol), biphenylcarbazolylboronic acid 12.37 g (34.05 mmol) and potassium carbonate 12.83 g (92.86 mmol), tetrakis-(triphenylphosphine) ) Palladium (0) 1.07 g (0.93 mmmol) was suspended in 120 ml of toluene and 50 ml of distilled water, followed by stirring under reflux for 12 hours. Then, the mixture was extracted with dichloromethane and distilled water, and the organic layer was filtered through silica gel. Then, the organic solution was removed, and the product solid was recrystallized from dichloromethane and n-hexane to obtain 18.7 g of Compound B-43 (yield: 92%).

HRMS (70 eV, EI+): m/z calcd for C48H32N2: 636.26, found: 636

Elemental Analysis: C, 91%; H, 5%

Synthesis Example 144A: Synthesis of compound B-114

In a 500 mL round-bottom flask equipped with a stirrer under nitrogen atmosphere, 20.00 g (50.21 mmol) of 3-bromo-N-biphenylcarbazole, 18.54 g (50.21 mmol) of N-phenylcarbazole-3-boronic ester, and tetra After mixing 175 mL of hydrofuran:toluene (1:1) and 75 mL of 2M-potassium carbonate aqueous solution, 2.90 g (2.51 mmol) of tetrakistriphenylphosphine palladium (0) was added and heated to reflux for 12 hours under a nitrogen stream. did. After completion of the reaction, the reactant was poured into methanol, the solid was filtered, and the obtained solid was sufficiently washed with water and methanol and dried. The resulting product was dissolved by heating in 700 mL of chlorobenzene, and then the solution was filtered through silica gel, the solvent was completely removed, and then dissolved by heating in 400 mL of chlorobenzene, followed by recrystallization to obtain 19.15 g of Compound A2 (yield 68%). .

calcd. C ₄₂ H ₂₈ N ₂ : C, 89.97; H, 5.03; N, 5.00; found: C, 89.53; H, 4.92; N, 4.89

Synthesis Example 141: Synthesis of compound (141)-1

1) Synthesis of intermediate (141)A

2-Bromodibenzofuran (10.0 g, 40.0 mmol), carbazole (8.121 g, 49.0 mmol), Pd ₂ (dba) ₃ (1.85 g, 2.0 mmol), tri- tert - Tri- tert -butylphosphine (0.57 g, 3.00 mmol) and sodium- tert -butoxide ( 9.72 g, 101 mmol) were mixed with toluene (120 mL). The temperature was raised to 110 °C under a nitrogen atmosphere and stirred for 18 hours under reflux, the mixture was cooled to room temperature, and extracted with 200 mL of water and 800 mL of methylene chloride. The obtained organic layer was dried over MgSO ₄ , and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain an intermediate (141)A (11.5 g, 85%). The produced compound was identified through LC-MS and HPLC analysis.

LC-MS ( m/z ) = C ₂₄ H ₁₅ NO (M ⁺ ) 333.

2) Synthesis of intermediate (141)B

Intermediate (141)A (11.5 g, 34.5 mmol) was dissolved in THF (80 mL), followed by stirring at -78 °C for 10 minutes. n -Butyllithium (20.7 mL of a 1.6 M solution in hexanes, 51.7 mmol) was slowly added dropwise for 30 minutes, followed by stirring at -78 °C for 4 hours. 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (10.6 mL, 51.7 mmol) was added, and after 15 minutes, the temperature was raised to room temperature, and after stirring for 5 hours, 100 mL of distilled water was added to the mixture and stirred. . The organic layer obtained by adding methylene chloride (150 mL X 3) was dried using MgSO ₄ , and the residue obtained by evaporating the solvent was recrystallized (dichloromethane / Methanol) to obtain an intermediate (141)B (11.5 g, 75%). . The produced compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₃₀ H ₂₆ BNO ₃ (M ⁺ ) 459.

3) Synthesis of compound (141)-1

Intermediate (141)B (7.55 g, 17.0 mmol), compound (141)E-1 (6.01 g, 15.5 mmol), Pd(PPh ₃ ) ₄ (0.94 g, 0.31 mmol), K ₂ CO ₃ (4.28 g, 31.0 mmol) is dissolved in 100 mL of THF and 50 mL of distilled water. Raise the temperature to 80 ℃ and stir for 18 hr while refluxing. After the reaction solution was cooled to room temperature, 100 mL of distilled water was added to the mixture, stirred, and the organic layer obtained by adding methylene chloride (150 mL X 3) was dried over MgSO ₄ , and the residue obtained by evaporating the solvent was subjected to silica gel column chromatography. was separated and purified to obtain compound (141)-1 (7.80 g, 78 %). The resulting compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₄₅ H ₂₈ N ₄ O (M ⁺ ) 640.

Synthesis Example 142: Synthesis of compound (141)-2

The same method as the synthesis method of Synthesis Example 141 was followed, except that Compound (141)E-2 (4.07 g, 10.5 mmol) was used instead of Compound (141)E-1 (4.07 g, 10.5 mmol). was used to obtain compound (141)-2 (4.33 g, 63%). The resulting compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₄₆ H ₂₉ N ₃ O (M ⁺ ) 639.

Synthesis Example 143: Synthesis of compound (141)-3

Compound (141) using the same method as in Synthesis Example 141, except that Compound E-3 (4.07 g, 10.5 mmol) was used instead of Compound (141)E-1 (4.07 g, 10.5 mmol). (141)-3 (4.10 g, 61%) was obtained. The resulting compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₄₆ H ₂₉ N ₃ O (M ⁺ ) 639.

Synthesis Example 144: Synthesis of compound (141)-4

The same method as the synthesis method of Synthesis Example 141 was followed, except that Compound (141)E-4 (4.07 g, 10.5 mmol) was used instead of Compound (141)E-1 (4.07 g, 10.5 mmol). was used to obtain compound (141)-4 (4.84 g, 72%). The resulting compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₄₆ H ₂₉ N ₃ O (M ⁺ ) 639.

Synthesis Example 145: Synthesis of compound (141)-5

The same method as in Synthesis Example 141 was followed except that Compound (141)E-2 (2.80 g, 10.5 mmol) was used instead of Compound (141)E-1 (4.07 g, 10.5 mmol). was used to obtain compound (141)-5 (5.45 g, 92%). The resulting compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₄₀ H ₂₅ N ₃ O (M ⁺ ) 564.

Synthesis Example 146: Synthesis of compound (141)-6

The same method as in Synthesis Example 141 was followed except that Compound (141)E-6 (2.81 g, 10.5 mmol) was used instead of Compound (141)E-1 (4.07 g, 10.5 mmol). was used to obtain compound (141)-6 (4.51 g, 77%). The resulting compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₃₉ H ₂₄ N ₄ O (M ⁺ ) 563.

Synthesis Example 147: Synthesis of compound (141)-7

The same method as in Synthesis Example 141 was followed except that Compound (141)E-7 (4.38 g, 10.5 mmol) was used instead of Compound (141)E-1 (4.07 g, 10.5 mmol). was used to obtain compound (141)-7 (5.56 g, 79%). The resulting compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₄₅ H ₂₇ N ₃ OS (M ⁺ ) 669.

Synthesis Example 148: Synthesis of compound (141)-8

The same method as the synthesis method of Synthesis Example 141 was followed, except that Compound (141)E-8 (3.58 g, 10.5 mmol) was used instead of Compound (141)E-1 (4.07 g, 10.5 mmol). was used to obtain compound (141)-8 (5.49 g, 88%). The resulting compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₄₀ H ₂₃ N ₃ OS (M ⁺ ) 593.

Synthesis Example 149: Synthesis of compound (141)-9

The same method as the synthesis method of Synthesis Example 141 was followed, except that Compound (141)E-9 (4.21 g, 10.5 mmol) was used instead of Compound (141)E-1 (4.07 g, 10.5 mmol). was used to obtain compound (141)-9 (4.81 g, 70%). The resulting compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₄₆ H ₂₇ N ₃ O ₂ (M ⁺ ) 653.

Synthesis Example 150: Synthesis of compound (141)-10

The same method as the synthesis method of Synthesis Example 141 was followed, except that Compound (141)E-10 (3.41 g, 10.5 mmol) was used instead of Compound (141)E-1 (4.07 g, 10.5 mmol). was used to obtain compound (141)-10 (3.88 g, 64 %). The resulting compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₄₀ H ₂₃ N ₃ O ₂ (M ⁺ ) 564.

Synthesis Example 151A: Synthesis of compound (141)-11

1) Synthesis of intermediate (141)C

2-Bromodibenzothiophene (30.0 g, 114 mmol), carbazole (21.0 g, 125 mmol), Pd(dba) ₂ (0.65 g, 1.14 mmol), Tri- tert -butylphosphine (0.69 g, 3.42 mmol), sodium- tert - butoxide (12.1 g, 125 mmol) was mixed with Toluene (360 mL). The temperature was raised to 110 °C under nitrogen and stirred for 18 hours under reflux, the mixture was cooled to room temperature, and extracted with 300 mL of water and 1000 mL of methylene chloride. The organic layer obtained therefrom was dried over MgSO ₄ , and the residue obtained by evaporating the solvent was recrystallized (toluene / methanol) to obtain an intermediate (141)C (33.4 g, 84 %). The resulting compound was identified through LC-MS and HPLC analysis.

LC-MS ( m/z ) = C ₂₄ H ₁₅ NS (M ⁺ ) 349.

2) Synthesis of intermediate (141)D

Intermediate (141)C (15.0 g, 42.9 mmol) was dissolved in THF (210 mL), followed by stirring at -78 °C for 10 minutes. n -Butyllithium (26.0 mL of a 2.5 M solution in hexanes, 64.4 mmol) was slowly added dropwise for 30 minutes, followed by stirring at -78 °C for 4 hours. 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (16.0 mL, 64.4 mmol) was added, and after 15 minutes, the temperature was raised to room temperature. After stirring for 5 hours, 100 mL of distilled water was added to the mixture and stirred. . The organic layer obtained by adding methylene chloride (150 mL X 3) was dried using MgSO ₄ , and the residue obtained by evaporating the solvent was recrystallized (dichloromethane / Methanol) to obtain an intermediate (141)D (15.3 g, 75%). . The resulting compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₃₀ H ₂₆ BNO ₂ S (M ⁺ ) 475.

3) Synthesis of compound (141)-11

Intermediate (141)D (5.00 g, 10.5 mmol), compound (141)E-1 (4.07 g, 10.5 mmol), Pd(PPh ₃ ) ₄ (0.61 g, 0.53 mmol), K ₂ CO ₃ (7.26 g, 52.6 mmol) is dissolved in 200 mL of toluene, 40 mL of ethanol and 60 mL of distilled water. Raise the temperature to 120 ℃ and stir for 18 hr while refluxing. After the reaction solution was cooled to room temperature, 100 mL of distilled water was added to the mixture, stirred, and the resulting solid was filtered, and the obtained residue was recrystallized (toluene / methanol) to obtain compound (14)-11 (5.34 g, 77 %). The resulting compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₄₅ H ₂₈ N ₄ S (M ⁺ ) 656.

Synthesis Example 152A: Synthesis of compound (141)12

The same method as in Synthesis Example 151A was followed, except that compound (141)E-2 (4.07 g, 10.5 mmol) was used instead of compound (141)E-1 (4.07 g, 10.5 mmol). was used to obtain compound (141)-12 (5.30 g, 77 %). The resulting compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₄₆ H ₂₉ N ₃ S (M ⁺ ) 655.

Synthesis Example 153A: Synthesis of compound (141)-13

The same method as in Synthesis Example 151A was followed, except that Compound (141)E-3 (4.07 g, 10.5 mmol) was used instead of Compound (141)E-1 (4.07 g, 10.5 mmol). was used to obtain compound (141)-13 (4.86 g, 64 %). The resulting compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₄₆ H ₂₉ N ₃ S (M ⁺ ) 655.

Synthesis Example 154A: Synthesis of compound (141)-14

The same method as in Synthesis Example 151A was followed, except that Compound (141)E-4 (4.07 g, 10.5 mmol) was used instead of Compound (141)E-1 (4.07 g, 10.5 mmol). was used to obtain compound (141)-14 (5.16 g, 75%). The resulting compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₄₆ H ₂₉ N ₃ S (M ⁺ ) 655.

Synthesis Example 155A: Synthesis of compound (141)-15

The same method as in Synthesis Example 151A was followed, except that Compound (141)E-5 (2.80 g, 10.5 mmol) was used instead of Compound (141)E-1 (4.07 g, 10.5 mmol). was used to obtain compound (141)-15 (4.44 g, 73%). The resulting compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₄₀ H ₂₅ N ₃ S (M ⁺ ) 579.

Synthesis Example 156A: Synthesis of compound (141)-16

The same method as in Synthesis Example 151A was followed except that compound (141)E-6 (2.81 g, 10.5 mmol) was used instead of compound (141)E-1 (4.07 g, 10.5 mmol). was used to obtain compound (141)-16 (4.15 g, 68%). The produced compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₃₉ H ₂₄ N ₄ S (M ⁺ ) 580.

Synthesis Example 157A: Synthesis of compound (141)-17

The same method as the synthesis method of Synthesis Example 151A was followed, except that Compound (141)E-7 (4.38 g, 10.5 mmol) was used instead of Compound (141)E-1 (4.07 g, 10.5 mmol). was used to obtain compound (141)-17 (5.76 g, 80%). The produced compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₄₆ H ₂₇ N ₃ S (M ⁺ ) 685.

Synthesis Example 158A: Synthesis of compound (141)-18

The same method as the synthesis method of Synthesis Example 151A was followed, except that Compound (141)E-8 (3.58 g, 10.5 mmol) was used instead of Compound (141)E-1 (4.07 g, 10.5 mmol). was used to obtain compound (141)-18 (4.74 g, 74 %). The produced compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₄₀ H ₂₃ N ₃ S ₂ (M ⁺ ) 609.

Synthesis Example 159A: Synthesis of compound (141)-19

The same method as in Synthesis Example 151A was followed, except that Compound (141)E-9 (4.21 g, 10.5 mmol) was used instead of Compound (141)E-1 (4.07 g, 10.5 mmol). was used to obtain compound (141)-19 (4.99 g, 71 %). The produced compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₄₆ H ₂₇ N ₃ S (M ⁺ ) 669.

Synthesis Example 160: Synthesis of compound (141)-20

The same method as in Synthesis Example 151A was followed, except that Compound (141)E-10 (3.41 g, 10.5 mmol) was used instead of Compound (141)E-1 (4.07 g, 10.5 mmol). was used to obtain compound (141)-20 (4.18 g, 67 %). The produced compound was identified through LC-MS and HPLC analysis.

LC-MS (m/z) = C ₄₀ H ₂₃ N ₃ OS (M ⁺ ) 593.

Examples 1 to 6 and Comparative Example 1

A glass substrate on which an ITO electrode was formed as an anode was cut into a size of 50 mm x 50 mm x 0.5 mm and ultrasonically cleaned in acetone isopropyl alcohol and pure water for 15 minutes each, followed by UV ozone cleaning for 30 minutes.

Compounds HT3 and F4-TCNQ (concentration of F4-TCNQ in the hole injection layer is 3wt%) were co-deposited on the anode to form a hole injection layer with a thickness of 100Å at a deposition rate of 1Å/sec, and on the hole injection layer The compound HT3 was deposited at a deposition rate of 1 Å/sec to form a hole transport layer having a thickness of 1660 Å.

A dopant and a host were co-deposited on the hole transport layer to form an emission layer having a thickness of 400 Å.

In each of Examples and Comparative Examples, materials used as dopant and host, content of dopant in light emitting layer, and weight ratio between two types of hosts when using two types of hosts are as shown in Table 9 below.

Compound ET16 and LiQ were co-deposited on the light emitting layer in a weight ratio of 5:5 to form an electron transport layer having a thickness of 360 Å, and then LiQ was deposited on the electron transport layer to form an electron injection layer having a thickness of 5 Å, and the electron injection By forming an Al electrode with a thickness of 800 Å on the layer, an organic light emitting device was fabricated.

Evaluation Example 1: Characterization of an organic light emitting device

The driving voltage, efficiency, and lifetime (T ₉₅ ) of each of the organic light emitting devices manufactured in Examples 1 to 6 and Comparative Example 1 were evaluated, and the results are shown in Table 9. As an evaluation device, a current-voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used, and the lifetime (T95) (at 6000 nit) was evaluated for the time it takes to reach 95% of the initial luminance compared to 100% of the initial luminance.

From Table 9, it can be seen that the organic light-emitting devices of Examples 1 to 6 have superior driving voltage, efficiency, and lifespan characteristics compared to the organic light-emitting devices of Comparative Example 1.

10: organic light emitting device
11: first electrode
15: organic layer
19: second electrode

Claims (20)

a first electrode;
a second electrode opposite to the first electrode; and
an organic layer disposed between the first electrode and the second electrode and including a light emitting layer;
The organic layer includes a first material and a second material,
The first material includes an organometallic compound represented by the following formula (1),
The second material is a host,
i) the host comprises a compound represented by one of the following formulas 31A, 61, 131A and 141,
ii) the host comprises a first host and a second host,
The first host includes a compound represented by one of Formulas 31A, 61, 131A, and 141, and the second host includes a compound represented by Formula 131B.
<Formula 1>

In Formula 1, R ₁₁ to R ₁₈ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, A hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, 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 monovalent non-aromatic condensed heteropolycyclic group, -X ₁ (R ₁ )(R ₂ )(R ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₃ )(Q ₄ ) and - P(=O)(Q ₅ )(Q ₆ ), wherein at least one of R ₁₁ to R ₁₈ is represented by -X ₁ (R ₁ )(R ₂ )(R ₃ ),
In Formula 1, X ₁ is silicon (Si) or germanium (Ge),
Wherein R ₁ To R ₃ And Q ₁ To Q ₆ Are each independently hydrogen, deuterium, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted substituted 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 an unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ 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, and substituted or unsubstituted and a cyclic monovalent non-aromatic condensed heteropolycyclic group.
<Formula 31A>

Ring A in Formula 31A is a C ₁ -C ₂₀ heterocyclic group including at least two N as ring-forming atoms, wherein the C ₁ -C ₂₀ heterocyclic group is a 6-membered ring or a 6-membered ring condensed a 6-membered ring or a 6-membered ring in which a 5-membered ring is condensed;
In Formula 31A, L ₁ and L ₂ may each independently represent 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 heteroarylene group , a substituted or unsubstituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group;
a1 and a2 in Formula 31A are each independently selected from an integer of 0 to 3;
In Formula 31A, R ₁ to R ₉ 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 );
b1 and b2 in Formula 31A are each independently selected from an integer of 1 to 5;
In Formula 31A, at least one of R ₅ to R ₈ is 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 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, and a substituted or unsubstituted monovalent non-aromatic group It is selected from a heterocondensed polycyclic group.
<Formula 61>

<Formula 61A>

Ring A ₁ in Formula 61 is represented by Formula 61A;
In Formula 61A, X ₁ is N-[(L ₁ ) _a1- (R ₁ ) _b1 ], S, O, S(=O), S(=O) ₂ , C(=O), Si(R ₄ ) )(R ₅ ), P(R ₄ ), P(=O)(R ₄ ) or C=N(R ₄ );
In Formulas 61 and 61A, L ₁ to L ₃ may each independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, or a substituted or unsubstituted selected from a C ₆ -C ₆₀ arylene group and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, L ₂ and L ₃ are not a substituted or unsubstituted carbazolylene group;
a1 to a3 in Formulas 61 and 61A are each independently selected from an integer of 0 to 5;
In Formulas 61 and 61A, R ₁ to R ₅ may each independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, or a hydrazine group , hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted substituted 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 an unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ 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 cyclic monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ) and -B(Q ₆ )(Q ₇ ) However, at least one of R ₂ and R ₃ is a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic group It is selected from a condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;
In Formula 61, R ₁₁ to R ₁₄ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydra Group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ) and -B(Q ₆ )(Q ₇ );
b1 to b3 in Formulas 61 and 61A are each independently selected from an integer of 1 to 3;
R ₃ in Formula 61 is not a substituted or unsubstituted morpholinyl group;
In Formula 61, when R ₃ is a pyridinyl group, a pyridazinyl group, or a pyrimidinyl group, R ₂ is hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, or a nitro group , amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ - C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted di selected from benzothiophenyl groups;
In Formula 61, when R ₂ is a substituted or unsubstituted phenyl group, R ₃ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted triphenyl Renyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted carbazolyl group, substituted or Unsubstituted benzocarbazolyl group, substituted or unsubstituted dibenzocarbazolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted pyridinyl group, substituted or Unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quina selected from a jolinyl group and a substituted or unsubstituted quinoxalinyl group;
A substituent of R ₂ and R ₃ in Formula 61 is,
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts 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 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 ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B(Q ₂₆ )(Q ₂₇ ) is not a carbazolyl group substituted with at least one.
<Formula 131A>

In Formula 131A, each Z is independently N or CR ^a , and at least one of Z is N;
In Formula 131A, R ¹ to R ¹⁰ and R ^a are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C ₁ -C ₁₀ alkyl group, and a substituted or unsubstituted C ₆ -C ₁₂ aryl group,
The total number of 6-membered rings substituted on the triphenylene core in Formula 131A is 6 or less,
In Formula 131A, L is selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, and a substituted or unsubstituted terphenylene group,
In Formula 131A, n1 to n3 are each independently 0 or 1,
In Formula 131A, n1+n2+n3≥1.
<Formula 131B>

In Formula 131B, Y ¹ is a single bond, a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₂ -C ₂₀ alkenylene group, or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group , substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted A substituted C ₆ -C ₆₀ arylene group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic hetero condensed group selected from the polycyclic group,
Ar ¹ in Formula 131B is a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or Unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic group It is selected from a condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group,
In Formula 131B, R ¹¹ to R ¹⁴ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group , carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, 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 arylox 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 and substituted or unsubstituted 1 is selected from a non-aromatic condensed heterocyclic polycyclic group,
At least one of R ¹¹ to R ¹⁴ and Ar ¹ of Formula 131B includes a substituted or unsubstituted triphenylene group or a substituted or unsubstituted carbazole group,
<Formula 141>

In Formula 141, X ₁₁ is selected from an oxygen atom (O) and a sulfur atom (S);
In Formula 141, L ₁₁ to L ₁₄ are each independently a substituted or unsubstituted C ₁ -C ₆₀ alkylene group, a substituted or unsubstituted C ₂ -C ₆₀ alkenylene group, or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group , a substituted or unsubstituted C ₆ -C ₆₀ arylene group and a substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group;
a11 to a14 in Formula 141 are each independently selected from 0, 1, 2, 3, 4, and 5;
In Formula 141, R ₁₁ to R ₁₃ are each independently R _ET , hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, 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 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 an unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ) and -B(Q ₆ )(Q ₇ ) is selected from;
At least one of R ₁₁ to R ₁₃ in Formula 141 is R _ET ;
b11 to b13 in Formula 141 are each independently selected from 1, 2, 3, and 4;
R _ET in Formula 141 is selected from Formulas 141-9 to 149-52;

X ₉₁ in Formulas 149-1 to 149-52 is selected from O and S;
In Formulas 149-1 to 149-52, R ₉₁ and R ₉₂ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group A 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 ₁ -C ₆₀ alkoxy group, a C ₆ -C ₆₀ aryl group, C selected from a ₆ -C ₆₀ aryloxy group, a C ₆ -C ₆₀ arylthio group, and a C ₁ -C ₆₀ heteroaryl group;
a91 in Formulas 149-1 to 149-52 is selected from 1, 2, 3, and 4;
a92 in Formulas 149-1 to 149-52 is selected from 1, 2, and 3;
a93 in Formulas 149-1 to 149-52 is selected from 1 and 2;
a94 in Formulas 149-1 to 149-52 is selected from 1, 2, 3, 4, 5, and 6;
a95 in Formulas 149-1 to 149-52 is selected from 1, 2, 3, 4, and 5;
In Formulas 149-1 to 149-52, * represents a binding site with a neighboring atom.
In the description of Formulas 31A, 61, 131A, 131B and 141, the substituted nitrogen-containing electron transporting moiety, substituted phenylene group, substituted biphenylene group, substituted terphenylene group, substituted triphenylene group, substituted Carbazolyl group, 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 heterocycloalkenyl Rene 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 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, At least one of the substituents of the substituted C ₆ -C ₆₀ 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 polycyclic group is ,
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkyl a nyl group and a C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cyclo Alkyl 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 ) C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C substituted with at least one of )(Q ₁₄ )(Q ₁₅ ) and -B(Q ₁₆ )(Q ₁₇ ) 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, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkyl nyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy 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, a C ₃ -C ₁₀ cycloalkyl group substituted with at least one of —N(Q ₂₁ )(Q ₂₂ ), —Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and —B(Q ₂₆ )(Q ₂₇ ), 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 an 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
-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) and -B(Q ₃₆ )(Q ₃₇ ); is selected from;
The 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, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts 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 1 substituted with at least one of a C 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 a group oxy group, a C ₆ -C ₆₀ aryl group thio 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, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts 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 aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C substituted with at least one of a ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed polycyclic group 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, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group; is selected from According to claim 1,
In Formula 1, R ₁₁ to R ₁₈ are each independently
hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, -SF ₅ , a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₁₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cycloox substituted with at least one of a tyl group, an adamantanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group, C ₁ - C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;
Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorine group Nyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, iso Thiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolyl group Nyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl 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, imidazopyridinyl group and an imidazopyrimidinyl group;
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohex Sil group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, Anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group , quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzoxazolyl group , triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl group substituted with at least one of a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group (adamantanyl), a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group , naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl 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, fu Linyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl 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, di a benzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; and
-X ₁ (R ₁ )(R ₂ )(R ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₃ )(Q ₄ ), and -P(=O)(Q ₅ )(Q ₆ ); selected from among
At least one of R ₁₁ to R ₁₈ is represented by -X ₁ (R ₁ )(R ₂ )(R ₃ ),
Q ₁ to Q ₆ are each independently,
C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, triazinyl group and carbazolyl group;
a phenyl group and a naphthyl group substituted with at least one of a C ₁ -C ₂₀ alkyl group, a phenyl group and a naphthyl group; is selected from
The R ₁ to R ₃ are the same as those described in claim 1, an organic light emitting device. According to claim 1,
In Formula 1, R ₁₁ to R ₁₈ are each independently
Hydrogen, deuterium, -F, cyano group, nitro group, -SF ₅ , methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n -pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group , tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isode Sil group, sec-decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl) , a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group;
Deuterium, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, nitro group, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group Tyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec- Decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group; and
-X ₁ (R ₁ )(R ₂ )(R ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₃ )(Q ₄ ), and -P(=O)(Q ₅ )(Q ₆ ); selected from among
At least one of R ₁₁ to R ₁₈ is represented by -X ₁ (R ₁ )(R ₂ )(R ₃ ),
Q ₁ to Q ₆ are each independently,
C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, phenyl group and naphthyl group;
a phenyl group and a naphthyl group substituted with at least one of a C ₁ -C ₁₀ alkyl group, a phenyl group, and a naphthyl group; selected from among, an organic light emitting device. According to claim 1,
In Formula 1, R ₁₁ to R ₁₈ are each independently hydrogen, deuterium, -F, cyano group, nitro group, -SF ₅ , -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a group represented by the following Chemical Formulas 9-1 to 9-17, a group represented by the following Chemical Formulas 10-1 to 10-16, and -X ₁ (R ₁ )(R ₂ ) (R ₃ ), wherein at least one of R ₁₁ to R ₁₈ is -X ₁ (R ₁ )(R ₂ )(R ₃ ) An organic light-emitting device represented by:

According to claim 1,
Of -X ₁ (R ₁ )(R ₂ )(R ₃ ) of Formula 1, R ₁ to R ₃ are each independently
Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group , n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-ox Tyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec-decyl group, tert-decyl group, methoxy group, ethoxy group , propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group; and
Deuterium, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, nitro group, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group Tyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec- Decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group; selected from among, an organic light emitting device. According to claim 1,
Of -X ₁ (R ₁ )(R ₂ )(R ₃ ) of Formula 1, R ₁ to R ₃ are each independently
a methyl group, an ethyl group, and a phenyl group; and
a phenyl group substituted with at least one of deuterium, a methyl group, an ethyl group, and a phenyl group; selected from among, an organic light emitting device. According to claim 1,
Of -X ₁ (R ₁ )(R ₂ )(R ₃ ) of Formula 1, R ₁ to R ₃ are the same as each other, an organic light emitting device. According to claim 1,
An organic light emitting device wherein the organometallic compound represented by Formula 1 is represented by one of Formulas 1-1 to 1-77:

In Formulas 1-1 to 1-77,
R ₁₀₀ to R ₁₀₂ are each independently represented by -X ₁ (R ₁ )(R ₂ )(R ₃ ),
R ₁ to R ₃ are independently of each other,
Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group , n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-ox Tyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec-decyl group, tert-decyl group, methoxy group, ethoxy group , propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group; and
Deuterium, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, nitro group, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group Tyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec- Decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group; is selected from
R ₁₁ to R ₁₈ are independently of each other,
Hydrogen, deuterium, -F, cyano group, nitro group, -SF ₅ , methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n -pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group , tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isode Sil group, sec-decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl) , a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group;
Deuterium, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, nitro group, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group Tyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec- Decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group (adamantanyl), norbornenyl group (norbornenyl), a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group; and
-N(Q ₁ )(Q ₂ ), -B(Q ₃ )(Q ₄ ) and -P(=O)(Q ₅ )(Q ₆ ); is selected from
Q ₁ to Q ₆ are each independently,
C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, phenyl group and naphthyl group;
a phenyl group and a naphthyl group substituted with at least one of a C ₁ -C ₁₀ alkyl group, a phenyl group, and a naphthyl group; is selected from 9. The method of claim 8,
Wherein R ₁ To R ₃ Are independently of each other,
a methyl group, an ethyl group, and a phenyl group; and
a phenyl group substituted with at least one of deuterium, a methyl group, an ethyl group, and a phenyl group; is selected from
The R ₁₁ to R ₁₈ are each independently hydrogen, deuterium, -F, cyano group, nitro group, -SF ₅ , -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , - CF ₂ H, -CFH ₂ , an organic light emitting device selected from the group represented by the following Chemical Formulas 9-1 to 9-17 and the group represented by the following Chemical Formulas 10-1 to 10-16:

9. The method of claim 8,
wherein X ₁ is Si, and R ₁ to R ₃ are the same as each other. According to claim 1,
An organic light-emitting device, wherein the organometallic compound includes at least one of the following compounds 1 to 327 and 401 to 727:

delete According to claim 1,
The second material includes a compound represented by Formula 31A,
In Formula 31A,
a1 is 0;
R ₁ is selected from the following formulas 35-1 to 35-40;
b1 is 1;
R ₂ to R ₆ and R ₈ are hydrogen;
R ₇ is selected from the following formulas 35-1 to 35-40;
a2 is 0 or 1;
L ₂ is selected from the following Chemical Formulas 34-1 to 34-15;
Ring A is represented by the following Chemical Formula 32-1 (wherein R _9a and R _9b in Chemical Formula 32-1 are each independently selected from the following Chemical Formulas 35-1 to 35-40).

In Formulas 35-1 to 35-40,
Z ₁ to Z ₃ 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 Acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naph Tyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinolinyl group, and a quinazolinyl group;
d1 is 1 or 2, d2 is selected from an integer from 1 to 3, d3 is selected from an integer from 1 to 4, d4 is selected from an integer from 1 to 5, d5 is selected from an integer from 1 to 6, , d6 is selected from an integer from 1 to 7, and d8 is selected from an integer from 1 to 9;
* and *' are, independently of each other, binding sites with neighboring atoms. According to claim 1,
An organic light emitting device, wherein the second material includes a compound represented by the following Chemical Formula 141-1A:
<Formula 141-1A>

In Formula 141-1A,
X ₁₁ , L ₁₁ , a11 and b11 are the same as those described in claim 1,
R ₁₁ is represented by one of Formulas 149-1 to 149-52,
Formulas 149-1 to 149-52 are the same as those described in claim 1. According to claim 1,
The second material is an organic light emitting device including a compound represented by the following Chemical Formula 61-1:
<Formula 61-1>

in Formula 61-1
X ₁ is S or O,
L ₂ and L ₃ are independently of each other,
Phenylene group, naphthylene group, phenanthrenylene group, anthracenylene group, triphenylenylene group, carbazolylene group, pyridinylene group, pyrimidinylene group, triazinylene group, quinazolinylene group, quinolinylene group, isoquinylene group a nolinylene group, a naphthyridinylene group, and an oxadiazolylene 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, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, and a phenylene group substituted with at least one of a phenanthrenyl group , naphthylene group, phenanthrenylene group, anthracenylene group, triphenylenylene group, carbazolylene group, pyridinylene group, pyrimidinylene group, triazinylene group, quinazolinylene group, quinolinylene group, isoquinolinyl group a ren group, a naphthyridinylene group, and an oxadiazolylene group; is selected from
a2 and a3 are 0 or 1,
R ₂ and R ₃ are independently of each other,
Phenyl group, naphthyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group , pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and dibenzocarbazole group diary; and
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, cry Cenyl group, perylenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, triazinyl group, di A phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, triphenylle, substituted with at least one of a benzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group Nyl group, pyrenyl group, chrysenyl group, perylenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazole a diyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group; is selected from
b2 and b3 are 1,
R ₁₁ to R ₁₄ are the same as described in claim 1. According to claim 1,
An organic light-emitting device, wherein the second material includes a compound represented by one of the following Chemical Formulas 131Ac to 131Ah:
<Formula 131Ac><Formula131Ad>

<Formula 131Ae><Formula131Af>

<Formula 131Ag><Formula131Ah>

<Formula 131Ai><Formula131Aj>

<Formula 131Ak><Formula131Al>

<Formula 131Am><Formula131An>

<Formula 131Ao><Formula131Ap>

<Formula 131Aq><Formula131Ar>

<Formula 131As><Formula131At>

In Formulas 131Ac to 131Ah,
R ¹ to R ¹⁰ and R ⁶⁰ to R ⁷⁷ are each independently selected from hydrogen, deuterium, a C ₁ -C ₁₀ alkyl group and a phenyl group,
Z is each independently N or CR ^a ,
At least one of the plurality of Z is N,
wherein R ^a is the same as described in claim 1 . 17. The method according to any one of claims 13 to 16,
An organic light emitting device, wherein the second material further comprises a compound represented by the following Chemical Formula 131B-I:
<Formula 131B-I>

In Formula 131B-I,
R ¹¹ to R ¹³ and R ⁴³ to R ⁴⁴ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group , a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group and a naphthyl group,
Y ¹ and Y ² are independently of each other,
Single bond, phenylene group, naphthylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group, triphenylenylene group, pyrenylene group and a chrysenylene group; and
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or A salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a phenyl group substituted with a phenyl group (biphenyl group), a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, phenanthree phenyl group, naphthylene group, fluorenylene group, spiro-fluorenylene group, phenyl group substituted with at least one of nyl group, anthracenyl group, fluoranthrenyl group, triphenylenyl group, pyrenyl group and chrysenyl group a renylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, and a chrysenylene group; is selected from
Ar ¹ and Ar ² are each independently,
Phenyl group, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, di Benzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, cinolinyl group, quinazolinyl group, quinoxalinyl group, imidazopyridinyl group and imidazo pyrimidinyl 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, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, Phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, carbazolyl group, benzofuranyl group, benzo Thiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, cy phenyl group, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzoflu, substituted with at least one of nolinyl group, quinazolinyl group, quinoxalinyl group, imidazopyridinyl group and imidazopyrimidinyl group Orenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, Carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, quin a nolinyl group, an isoquinolinyl group, a cinolinyl group, a quinazolinyl group, a quinoxalinyl group, an imidazopyridinyl group and an imidazopyrimidinyl group; selected from among
At least one of Ar ¹ and Ar ² is,
Phenyl group, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and di benzocarbazolyl 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, pentalenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, Phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group, carbazolyl group, benzofuranyl group, benzo A phenyl group, a pentalenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, benzo which is substituted with at least one of a thiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group Fluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, picenyl group, perylenyl group, pentaphenyl group , a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group; is selected from delete According to claim 1,
The first material and the second material are included in the light emitting layer,
The first material is a dopant, and the second material is a host. delete

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