AMINE-BASED COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME

Description

CROSS-REFERENCE TO RELATED APPLICATION

Korean Patent Application No. 10-2013-0072718, filed on Jun. 24, 2013, in the Korean Intellectual Property Office, and entitled: “Amine-Based Compound and Organic Light-Emitting Device Including the Same,” is incorporated by reference herein in its entirety.

BACKGROUND

1. Field

One or more embodiments relate to an amine-based compound and an organic light-emitting device including the amine-based compound.

2. Description of the Related Art

Organic light-emitting devices (OLEDs), which are self-emitting devices, have advantages such as wide viewing angles, excellent contrast, quick response, high brightness, and excellent driving voltage characteristics and can provide multicolored images.

An organic light-emitting device may include an anode, a cathode, and an emission layer disposed between the anode and the cathode. The organic light-emitting device may include a hole transport region between the anode and the emission layer, and an electron transport region between the emission layer and the cathode. Holes injected from the anode move to the emission layer via the hole transport region, while electrons injected from the cathode move to the emission layer via the electron transport region. Carriers such as holes and electrons recombine in the emission layer to generate excitons. When the excitons drop from an excited state to a ground state, light is emitted.

SUMMARY

Embodiments are directed to an amine-based compound represented by Formula 1 below:

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wherein, in Formula 1, A₁is selected from

a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, and a benzofluoranthenylene group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₂-C₆₀heteroaryl group, —N(Q₁₁)(Q₁₂), and —Si(Q₁₃)(Q₁₄)(Q₁₅);

X₁is selected from N-[(L₁)_a1-(R₁)_b1], S, and O;

X₂is selected from N-[(L₂)_a2-(R₂)_b2], S, and O;

L₁, L₂, L₁₁, L₁₂, L₂₁, and L₂₂are each independently selected from

a C₃-C₁₀cycloalkylene group, a C₃-C₁₀heterocycloalkylene group, a C₃-C₁₀cycloalkenylene group, a C₃-C₁₀heterocycloalkenylene group, a C₆-C₆₀arylene group, and a C₂-C₆₀heteroarylene group, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₂-C₆₀heteroaryl group, —N(Q₁₁)(Q₁₂), and —Si(Q₁₃)(Q₁₄)(Q₁₅);

a1, a2, a11, a21, and a22 are each independently an integer from 0 to 5;

R₁, R₂, R₁₁, and R₁₂are each independently selected from

a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, and a C₂-C₆₀alkynyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, and a C₂-C₆₀heteroaryl group,

a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, and a C₂-C₆₀heteroaryl group, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, and a C₂-C₆₀heteroaryl group;

R₃to R₆are each independently selected from

a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, and a C₁-C₆₀alkoxy group,

a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, and a C₁-C₆₀alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, and a C₂-C₆₀heteroaryl group,

a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, and a C₂-C₆₀heteroaryl group, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, and a C₂-C₆₀heteroaryl group, and

—N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇);

Q₁₁to Q₁₅, and Q₁to Q₇are each independently selected from

a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, and a C₂-C₆₀heteroaryl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, and a C₂-C₆₀heteroaryl group;

b3 and b5 are each independently 1 or 2; and

b1, b2, b4, and b6 are each independently 1, 2, or 3.

A₁may be selected from a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, and a benzofluoranthenylene group, and

- a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, and a benzofluoranthenylene group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group.

X₁and X₂may both be S, or X₁and X₂may both be O.

L₁, L₂, L₁₁, L₁₂, L₂₁, and L₂₂may each independently be selected from a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pyrrolylene group, an imidazolylene group, a pyrazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a carbazolylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzooxazolylene group, a benzoimidazolylene group, a furanylene group, a benzofuranylene group, a thiophenylene group, a benzothiophenylene group, a thiazolylene group, an isothiazolylene group, a benzothiazolylene group, an isoxazolylene group, an oxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, and a dibenzocarbazolylene group, and

- a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pyrrolylene group, an imidazolylene group, a pyrazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a carbazolylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzooxazolylene group, a benzoimidazolylene group, a furanylene group, a benzofuranylene group, a thiophenylene group, a benzothiophenylene group, a thiazolylene group, an isothiazolylene group, a benzothiazolylene group, an isoxazolylene group, an oxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, and a dibenzocarbazolylene group, each substitute with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group.

L₁, L₂, L₁₁, L₁₂, L₂₁, and L₂₂may each independently be selected from the groups represented by Formulae 2-1 to 2-30 below:

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- wherein, in Formulae 2-1 to 2-30,
- Y₁is O, S, S(═O), S(═O)₂, C(Z₃)(Z₄), N(Z₅), or Si(Z₆)(Z₇);
- Z₁to Z₇are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl 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
- * and *′ indicate binding sites of adjacent atoms.

L₁, L₂, L₁₁, L₁₂, L₂₁, and L₂₂are each independently selected from the groups represented by Formulae 3-1 to 3-19 below:

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a1, a2, a11, a12, a21, and a22 may each independently be 0, 1, or 2.

R₁, R₂, R₁₁, and R₁₂may each independently be selected from

- 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 phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthrenyl 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 pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzooxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a benzooxazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group, and
- 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 phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthrenyl 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 pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzooxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a benzocarbazolyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group.

R₃to R₆may each independently be selected from

- a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, and a C₁-C₂₀alkoxy group;
- a C₁-C₂₀alkyl group and a C₁-C₆₀alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl 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, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthrenyl 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 pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzooxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a benzooxazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl 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, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthrenyl 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 pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzooxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a benzocarbazolyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group; and
- —N(Q₁)(Q₂), and —Si(Q₃)(Q₄)(Q₅), wherein Q₁to Q₅are each independently selected from
- a hydrogen atom, a C₁-C₂₀alkyl group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group; and
- a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group.

R₁, R₂, R₁₁, and R₁₂may each independently be selected from the groups represented by Formulae 4-1 to 4-29 below; and

- R₃to R₆may each independently be selected from
- a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, and a C₁-C₂₀alkoxy group,
- a C₁-C₂₀alkyl group and a C₁-C₂₀alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group,
- the groups represented by Formulae 4-1 to 4-29 below, and
- —N(Q₁)(Q₂) and —Si(Q₃)(Q₄)(Q₅), wherein Q₁to Q₅are each independently selected from
- a hydrogen atom, a C₁-C₂₀alkyl group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group; and
- a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group:

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- wherein, in Formulae 4-1 to 4-29,
- Y₃₁is O, S, C(Z₃₃)(Z₃₄), N(Z₃₅), or Si(Z₃₆)(Z₃₇);
- Z₃₁to Z₃₇are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl 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; and
- * indicates a binding site of an adjacent atom.

R₁, R₂, R₁₁, and R₁₂may each independently be selected from the groups represented by Formulae 5-1 to 5-36 below; and

- R₃to R₆are each independently selected from
- a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, and a C₁-C₂₀alkoxy group,
- a C₁-C₂₀alkyl group and a C₁-C₂₀alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group,
- the groups represented by Formulae 5-1 to 5-36 below, and
- —N(Q₁)(Q₂), and —Si(Q₃)(Q₄)(Q₅), wherein Q₁to Q₅are each independently selected from
- a hydrogen atom, a C₁-C₂₀alkyl group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group; and
- a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group:

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The amine-based compound of Formula 1 may be a compound represented by Formula 1A below:

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- wherein, in Formula 1A, A₁, X₁, X₂, L₁₁, L₁₂, L₂₁, L₂₂, a11, a12, a21, a22, R₁₁, and R₁₂are the same as those defined in claim 1, and R₂₁to R₃₀are the same as R₃defined in claim 1.

The amine-based compound of Formula 1 may be a compound represented by one of Formulae 1A(1) to 1A(4) below:

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- wherein, in Formulae 1A(1) to 1A(4),
- X₁, X₂, L₁₁, L₁₂, L₂₁, L₂₂, a11, a12, a21, a22, R₁₁, and R₁₂are the same as those defined in claim 1;
- R₂₁to R₃₄are the same as R₃defined in claim 1;
- a31 and a32 are each independently an integer from 1 to 4;
- a33 is an integer from 1 to 8;
- a34 and a35 are each independently an integer from 1 to 3;
- a36 and a37 are each independently an integer from 1 to 5.

The amine-based compound of Formula 1 may be one of Compounds 1 to 108 below:

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Embodiments are also directed to an organic light-emitting device including a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, and including an emission layer and at least one of the amine-based compounds of claim 1.

The first electrode may be an anode, the second electrode may be a cathode, and the organic layer may include i) a hole transport region between the first electrode and the emission layer and including at least one of a hole injection layer, a hole transport layer, and an electron blocking layer, and ii) an electron transport region 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.

The organic layer may further include a compound represented by Formula 1000 below:

Y₁−A₂−Y₂ <Formula 1000>

- wherein, in Formula 1000, A₂is selected from
- a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, and a benzofluoranthenylene group, and
- a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, and a benzofluoranthenylene group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₂-C₆₀heteroaryl group, —N(Q₁₁)(Q₁₂), and —Si(Q₁₃)(Q₁₄)(Q₁₅);
- Y₁and Y₂are each independently selected from
- a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, and a C₂-C₆₀heteroaryl group, and
- a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, and a C₂-C₆₀heteroaryl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₂-C₆₀heteroaryl group, and —N(Q₁₀₁)(Q₁₀₂); and
- Q₁₀₁and Q₁₀₂are each independently selected from
- a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, and a C₁-C₆₀alkoxy group, and
- a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, and a C_rC₆₀alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, and a C₂-C₆₀heteroaryl group,
- a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, and a C₂-C₆₀heteroaryl group, and
- a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, and a C₂-C₆₀heteroaryl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, and a C₂-C₆₀heteroaryl group.

The amine-based compound may be in the emission layer.

The amine-based compound and the compound of Formula 1000 may both be in the emission layer, and an amount of the amine-based compound in the emission layer may less than an amount of the compound of Formula 1000.

The hole transport region may include at least one of a compound represented by Formula 300 below and a compound represented by Formula 301 below:

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- wherein, in Formula 300, Ar₁₀₁and Ar₁₀₂are each independently selected from
- a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, and a pentacenylene group, and
- a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, and a pentacenylene group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, and a C₂-C₆₀heteroaryl group;
- xa and xb in Formula 300 are each independently 0, 1, or 2;
- R₁₀₁to R₁₀₈, R₁₁₁to R₁₁₉, and R₁₂₁to R₁₂₄in Formulae 300 and 301 are each independently selected from
- a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₁₀alkyl group, and a C₁-C₁₀alkoxy group,
- a C₁-C₁₀alkyl group and a C₁-C₁₀alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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,
- a phenyl group, a naphthyl group, an anthracenylene group, a fluorenyl group, and a pyrenyl group, and
- a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₁₀alkyl group, and a C₁-C₁₀alkoxy group; and
- R₁₀₉in Formula 300 is selected from a phenyl group, a naphthyl group, an anthracenyl group, a biphenyl group, and a pyridyl group; and a phenyl group, a naphthyl group, an anthracenyl group, a biphenyl group, and a pyridyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, and a C₁-C₂₀alkoxy group.

BRIEF DESCRIPTION OF THE DRAWING

Features will become apparent to those of skill in the art by describing in detail exemplary embodiments with reference to the attached drawings in which:

FIG. 1 illustrates a schematic view of an organic light-emitting device according to an embodiment.

DETAILED DESCRIPTION

Example embodiments will now be described more fully hereinafter with reference to the accompanying drawing; however, they may be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey exemplary implementations to those skilled in the art.

In the drawing FIGURE, the dimensions of layers and regions may be exaggerated for clarity of illustration. It will also be understood that when a layer or element is referred to as being “on” another layer or substrate, it can be directly on the other layer or substrate, or intervening layers may also be present. Further, it will be understood that when a layer is referred to as being “under” another layer, it can be directly under, and one or more intervening layers may also be present. In addition, it will also be understood that when a layer is referred to as being “between” two layers, it can be the only layer between the two layers, or one or more intervening layers may also be present. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.

According to an aspect, there is provided an amine-based compound represented by Formula 1:

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In Formula 1, A₁may be selected from

a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, and a benzofluoranthenylene group, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₂-C₆₀heteroaryl group, —N(Q₁₁)(Q₁₂), and —Si(Q₁₃)(Q₁₄)(Q₁₅), wherein Q₁₁to Q₁₅will be defined below.

For example, A₁in Formula 1 above may be selected from

a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, and a benzofluoranthenylene group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group, but is not limited thereto.

In some embodiments, A₁in Formula 1 above may be selected from a naphthylene group, a dimethylfluorenylene group, a diphenylfluorenyl group, a spiro-fluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, and a benzofluoranthenylene group, but is not limited thereto.

In Formula 1, X₁may be selected from N-[(L₁)_a1-(R₁)_b1], S, and O, and X₂may be selected from N-[(L₂)_a2-(R₂)_b2], S, and O. L₁, L₂, R₁, R₂, a1, a2, b1, and b2 will be defined below.

In Formula 1 above, X₁and X₂may be identical to or different from each other. For example, X₁and X₂in Formula 1 may be identical to each other.

For example, X₁and X₂in Formula 1 may be both S, or X₁and X₂in Formula 1 may be both O.

In Formula 1, L₁, L₂, L₁₁, L₁₂, L₂₁, and L₂₂may be each independently selected from

a C₃-C₁₀cycloalkylene group, a C₃-C₁₀heterocycloalkylene group, a C₃-C₁₀cycloalkenylene group, a C₃-C₁₀heterocycloalkenylene group, a C₆-C₆₀arylene group, and a C₂-C₆₀heteroarylene group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₂-C₆₀heteroaryl group, —N(Q₁₁)(Q₁₂), and —Si(Q₁₃)(Q₁₄)(Q₁₅).

In some embodiments, L₁, L₂, L₁₁, L₁₂, L₂₁, and L₂₂in Formula 1 may be each independently selected from

a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pyrrolylene group, an imidazolylene group, a pyrazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a carbazolylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzooxazolylene group, a benzoimidazolylene group, a furanylene group, a benzofuranylene group, a thiophenylene group, a benzothiophenylene group, a thiazolylene group, an isothiazolylene group, a benzothiazolylene group, an isoxazolylene group, an oxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, and a dibenzocarbazolylene group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group.

In some other embodiments, L₁, L₂, L₁₁, L₁₂, L₂₁and L₂₂in Formula 1 above may be each independently selected from the groups represented by Formulae 2-1 to 2-30 below:

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In Formulae 2-1 to 2-30,

Y₁may be O, S, S(═O), S(═O)₂, C(Z₃)(Z₄), N(Z₅), or Si(Z₆)(Z₇);

Z₁to Z₇may be each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₂-C₆₀heteroaryl group, —N(Q₁₁)(Q₁₂), and —Si(Q₁₃)(Q₁₄)(Q₁₅) (where Q₁₁to Q₁₅are the same as defined in the specification);

d1 may be an integer from 1 to 4;

d2 may be an integer from 1 to 3;

d3 may be an integer from 1 to 6;

d4 may be an integer from 1 to 8;

d5 may be 1 or 2;

d6 may be an integer from 1 to 5; and

* and *′ indicate binding sites to adjacent atoms.

For example, in Formulae 2-1 to 2-30, * indicates a binding site of A₁in Formula 1 or an adjacent group of L₁, L₂, L₁₁, L₁₂, L₂₁, and L₂₂; and *′ indicates a binding site of an adjacent group of L₁, L₂, L₁₁, L₁₂, L₂₁, and L₂₂, or a binding site of R₁, R₂, R₁₁, R₁₂, R₂₁, and R₂₂.

For example, in Formulae 2-1 to 2-30, Z₁to Z₇may be each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group, but are not limited thereto.

In some other embodiments, L₁, L₂, L₁₁, L₁₂, L₂₁, and L₂₂in Formula 1 may be each independently selected from the groups represented by Formulae 3-1 to 3-19, but are not limited thereto:

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In Formula 1, a1 indicates the number of L₁s, which may be 0, 1, 2, 3, 4, or 5. For example, a1 may be 0, 1, or 2, and in some embodiments, may be 0 or 1. When a1 is 0, R₁is bound directly to N. When a1 is 2 or greater, at least two L₁s may be identical to or different from each other.

In Formula 1, a2 indicates the number of L₂s, which may be 0, 1, 2, 3, 4, or 5. For example, a2 may be 0, 1, or 2, and in some embodiments, may be 0 or 1. When a2 is 0, R₂is bound directly to N. When a2 is 2 or greater, at least two L₂s may be identical to or different from each other.

In Formula 1, all indicates the number of L₁₁s, which may be 0, 1, 2, 3, 4, or 5. For example, all may be 0, 1, or 2, and in some embodiments, may be 0 or 1. When all is 0, R₁₁is bound directly to N. When all is 2 or greater, at least two L₁₁s may be identical to or different from each other.

In Formula 1, a12 indicates the number of L₁₂s, which may be 0, 1, 2, 3, 4, or 5. For example, a1 may be 0, 1, or 2, and in some embodiments, may be 0 or 1. When a′2 is 0, R₁₂is bound directly to N. When a12 is 2 or greater, at least two L₁₂s may be identical to or different from each other.

In Formula 1, a21 indicates the number of L₂₁s, which may be 0, 1, 2, 3, 4, or 5. For example, a1 may be 0, 1, or 2, and in some embodiments, may be 0 or 1. When a21 is O, N in Formula 1 is bound directly to A₁. When a21 is 2 or greater, at least two L₂₁s may be identical to or different from each other.

In Formula 1, a22 indicates the number of L₂₂s, which may be 0, 1, 2, 3, 4, or 5. For example, a1 may be 0, 1, or 2, and in some embodiments, may be 0 or 1. When a22 is 0, R₂₂is bound directly to N in Formula 1. When a22 is 2 or greater, at least two L₂₂s may be identical to or different from each other.

In Formula 1, R₁, R₂, R₁₁, and R₁₂may be each independently selected from

- a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₆₀alkyl group, a C₁-C₂₀alkenyl group, and a C₂-C₆₀alkynyl group,

a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, and a C₂-C₆₀heteroaryl group, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, and a C₂-C₆₀heteroaryl group.

In Formula 1, R₃to R₆may be each independently selected from

—N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇).

The Q₁₁to Q₁₅, and Q₁to Q₇in this specification may be each independently selected from

in some embodiments, R₁, R₂, R₁₁, and R₁₂may be each independently selected from

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 phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthrenyl 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 pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzooxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a benzocarbazolyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group, but are not limited thereto.

In some other embodiments, R₃to R₆may be each independently selected from

a C₁-C₂₀alkyl group and a C₁-C₆₀alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group;

—N(Q₁)(Q₂) and —Si(Q₃)(Q₄)(Q₅), wherein Q₁to Q₅may be each independently selected from a hydrogen atom, a C₁-C₂₀alkyl group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group; and a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group.

In some other embodiments, R₁, R₂, R₁₁, and R₁₂may be each independently selected from the groups represented by Formulae 4-1 to 4-29; and R₃to R₆may be each independently selected from

a C₁-C₂₀alkyl group and a C₁-C₆₀alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group;

the groups represented by Formulae 4-1 to 4-29; and

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In Formulae 4-1 to 4-29,

Y₃₁may be O, S, C(Z₃₃)(Z₃₄), N(Z₃₅), or Si(Z₃₆)(Z₃₇);

Z₃₁to Z₃₇may be each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, and a C₂-C₆₀heteroaryl group;

e1 may be an integer from 1 to 5;

e2 may be an integer from 1 to 7;

e3 may be an integer from 1 to 3;

e4 may be an integer from 1 to 4;

e5 may be 1 or 2;

e6 may be an integer from 1 to 6; and

indicates a binding site of an adjacent atom.

For example, in Formulae 4-1 to 4-29, Z₃₁to Z₃₇may be each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group, but are not limited thereto.

For example, in Formulae 4-1 to 4-29, e1, e2, e3, e4, e5, and e6 may be each independently 1 or 2.

In some embodiments, in Formula 1, R₁, R₂, R₁₁, and R₁₂may be each independently selected from the groups represented by Formulae 5-1 to 5-36; and

R₃to R₆may be each independently selected from

a C₁-C₂₀alkyl group and a C₁-C₆₀alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group;

the groups represented by Formulae 5-1 to 5-36 below; and

—N(Q₁)(Q₂), and —Si(Q₃)(Q₄)(Q₅), wherein Q₁to Q₅may be each independently selected from a hydrogen atom, a C₁-C₂₀alkyl group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group; and a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group. However, embodiments are not limited thereto.

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In Formula 1, b1 indicates the number of R₁s, and may be an integer from 1 to 3. For example, b1 may be 1 or 2, and in some embodiments, may be 1. When b1 is 2 or greater, at least two R₁s may be identical to or different from each other.

In Formula 1, b2 indicates the number of R₂s, and may be an integer from 1 to 3. For example, b2 may be 1 or 2, and in some embodiments, may be 1. When b2 is 2 or greater, at least two R₂s may be identical to or different from each other.

In Formula 1, b3 indicates the number of R₃s, and may be 1 or 2. When b3 is 2 or greater, at least two R₃s may be identical to or different from each other.

In Formula 1, b4 indicates the number of R₄s, and may be 1, 2, or 3. When b4 is 2 or greater, at least two R₄s may be identical to or different from each other.

In Formula 1, b5 indicates the number of R₅s, and may be 1 or 2. When b5 is 2 or greater, at least two R₅s may be identical to or different from each other.

In Formula 1, b6 indicates the number of R₆s, and may be 1, 2 or, 3. When b6 is 2 or greater, at least two R₆s may be identical to or different from each other.

In Formula 1, R₄and R₆may be both hydrogen atoms.

The amine-based compound of Formula 1 above may be a compound represented by Formula 1A below.

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In Formula 1A, A₁, X₁, X₂, L₁₁, L₁₂, L₂₁, L₂₂, a11, a12, a21, a22, R₁₁, and R₁₂may be the same as those defined above in conduction with Formula 1. R₂₁to R₃₀in Formula 1A may be the same as R₃defined above in connection with Formula 1.

For example, in Formula 1A, A₁may be selected from

X₁and X₂may be identical to each other;

L₁, L₂, L₁₁, L₁₂, L₂₁, and L₂₂may be each independently selected from the groups represented by Formulae 2-1 to 2-30;

a1, a2, a11, a21, and a22 may be each independently 0 or 1;

R₁, R₂, R₁₁, and R₁₂may be each independently selected from the groups represented by Formulae 4-1 to 4-29;

R₂₁to R₃₀may be each independently selected from

a C₁-C₂₀alkyl group and a C₁-C₆₀alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group, and

the groups represented by Formulae 4-1 to 4-29 above;

b1 and b2 may be each independently 1 or 2. However, embodiments are not limited thereto.

In some other embodiments, in Formula 1A, A₁may be selected from a naphthylene group, a dimethylfluorenylene group, a diphenylfluorenylene group, a spiro-fluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, and a benzofluoranthenylene group;

X₁and X₂may be both S, or X₁and X₂may be both O;

L₁₁, L₁₂, L₂₁, and L₂₂may be each independently selected from the groups represented by Formulae 3-1 to 3-19 above;

a11, a21, and a22 may be each independently 0 or 1;

R₁₁and R₁₂may be each independently selected from the groups represented by Formulae 5-1 to 5-36 above;

R₂₁to R₃₀may be each independently selected from

a C₁-C₂₀alkyl group and a C₁-C₆₀alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group; and

the groups represented by Formulae 5-1 to 5-36 above; and

b1 and b2 may be each independently 1 or 2. However, embodiments are not limited thereto.

For example, in Formula 1A, R₂₃to R₂₅, and R₂₈to R₃₀may be all hydrogen atoms.

In some embodiments, the amine-based compound of Formula 1 above may be a compound represented by one of Formulae 1A(1) to 1A(4) below:

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In Formulae 1A(1) to 1A(4), X₁, X₂, L₁₁, L₁₂, L₂₁, L₂₂, a11, a12, a21, a22, R₁₁, and R₁₂may be the same as those defined above in conjunction with Formula 1, and R₂₁to R₃₄may be the same as R₃defined above in conjunction with Formula 1.

In Formulae 1A(1) to 1A(4), a31 and a32 may be each independently an integer from 1 to 4, a33 may be an integer from 1 to 8, a34 and a35 may be each independently an integer from 1 to 3, and a36 and a37 may be each independently an integer from 1 to 5.

In some other embodiments, in Formulae 1A(1) to 1A(4), X₁and X₂may be identical to each other;

L₁, L₂, L₁₁, L₁₂, L₂₁, and L₂₂may be each independently selected from the groups represented by Formulae 2-1 to 2-30;

a1, a2, a11, a21, and a22 may be each independently 0 or 1;

R₁, R₂, R₁₁, and R₁₂may be each independently selected from the groups represented by Formulae 4-1 to 4-29;

R₂₁to R₃₄may be each independently selected from

a C₁-C₂₀alkyl group and a C₁-C₆₀alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group, and

the groups represented by Formulae 4-1 to 4-29 above; and

b1 and b2 may be each independently 1 or 2. However, embodiments are not limited thereto.

In some other embodiments, in Formulae 1A(1) to 1A(4), X₁and X₂may be both S, or X₁and X₂may be both O;

L₁₁, L₁₂, L₂₁, and L₂₂may be each independently selected from the groups represented by Formulae 3-1 to 3-19 above;

a11, a21, and a22 may be each independently 0 or 1;

R₁₁and R₁₂may be each independently selected from the groups represented by Formulae 5-1 to 5-36 above;

R₂₁to R₃₄may be each independently selected from

a C₁-C₂₀alkyl group and a C₁-C₆₀alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group, and

the groups represented by Formulae 5-1 to 5-36 above; and

b1 and b2 may be each independently 1 or 2. However, embodiments are not limited thereto.

For example, in Formulae 1A(1) to 1A(4), R₂₃to R₂₅, and R₂₈to R₃₀may be all hydrogen atoms.

In Formula 1A(3), R₃₁and R₃₂may be each independently selected from a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a naphthyl group, and an anthracenyl group.

In Formula 1A(2), a21 and a22 may be both an integer of 1.

In Formulae 1A(1), 1A(2), and 1A(4), R₃₁and R₃₂may be all hydrogen atoms.

In Formulae 1A(3), R₃₃and R₃₄may be all hydrogen atoms.

In some embodiments, the amine-based compound of Formula 1 above may be a compound represented by one of the Compounds 1 to 108 below, but is not limited thereto:

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In the amine-based compound represented by Formula 1 above, X₁may be selected from N-[(L₁)_a1-(R₁)_b2], S, and O, and X₂may be selected from N-[(L₂)_a2-(R₂)_b2], S, and O. That is, X₁and X₂may be both not carbon atoms. Accordingly, the amine-based compound of Formula 1 may optimize electron injection balance. Thus, an organic light-emitting device including the amine-based compound of Formula 1 may have improved efficiency characteristics.

In the amine-based compound represented by Formula 1 above, “N” is bound to a “benzo group” of an “indole-based moiety” (refer to Formula 1′ below), which may provide improved electrical stability, not causing denaturation and/or decomposition of the compound despite of persistent movements of electrons. Accordingly, the amine-based compound of Formula 1 may optimize electron injection balance. Thus, an organic light-emitting device including the amine-based compound of Formula 1 may have improved efficiency characteristics.

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A synthesis method of the amine-based compound of Formula 1 above may be understood by those of ordinary skill in the art from Synthesis Examples 1 to 8 that will be described below

The amine-based compound of Formula 1 above may be appropriate for use in an organic layer of an organic light-emitting device, for example, as a dopant of an emission layer of the organic layer.

According to another aspect, an organic light-emitting device includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode and including at least one of the amine-based compounds of Formula 1 above.

Due to the inclusion of the organic layer including the amine-based compound of Formula 1 above, the organic light-emitting device may have a low driving voltage, a high efficiency, high luminance, long lifetime, and improved color purity.

With regard to the color purity of the organic light-emitting device including the amine-based compound of Formula 1 above, an X coordinate may be from about 0.14 to about 0.16, and a Y coordinate may be about 0.18 or less, and in some embodiments, from about 0.10 to about 0.15, and in some other embodiments, may be from about 0.12 to about 0.14. For example, the amine-based compound of Formula 1 may emit blue light, for example, fluorescent blue light.

The amine-based compound of Formula 1 above may be used between a pair of electrodes of an organic light-emitting device. For example, the amine-based compound of Formula 1 above may be in at least one of an emission layer, a hole transport region between the first electrode and the emission layer (for example, including at least one of a hole injection layer, a hole transport layer, and an electron blocking layer), and an electron transport region between the emission layer and the second electrode (for example, including at least one of a hole blocking layer, an electron transport layer, and an electron injection layer). In some embodiments, the amine-based compound of Formula 1 may be in at least one of the hole transport region, the electron transport region, and the emission layer.

In some other embodiments, the amine-based compound of Formula 1 above may be in the emission layer of the organic light-emitting device. The amine-based compound of Formula 1 above may be a fluorescent dopant emitting, for example, blue light based on fluorescence mechanism.

In some embodiments, the organic light-emitting device may further include a compound represented by Formula 1000 below, in addition to the amine-based compound of Formula 1 above.

Y₁−A₂−Y₂ <Formula 1000>

In Formula 1000, A₂may be selected from

a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, and a benzofluoranthenylene group, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₂-C₆₀heteroaryl group, —N(Q₁₁)(Q₁₂), and —Si(Q₁₃)(Q₁₄)(Q₁₅).

In Formula 1000, A₂may be the same as A₁defined above in conjunction with Formula 1.

In Formula 1000, Y₁and Y₂may be each independently selected from

Q₁₀₁and Q₁₀₂may be each independently selected from

a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, and a C₂-C₆₀heteroaryl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, and a C₂-C₆₀heteroaryl group.

in some embodiments, in Formula 1000, Y₁and Y₂may be each independently selected from

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 phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthrenyl 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 pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzooxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a benzocarbazolyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and —N(Q₁₀₁)(Q₁₀₂); wherein

Q₁₀₁and Q₁₀₂may be each independently selected from 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 phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthrenyl 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 pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzooxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a benzocarbazolyl group. However, embodiments are not limited thereto.

The amine-based compound of Formula 1 above and the compound of Formula 1000 above may be both in the emission layer of the organic light-emitting device. An amount of the amine-based compound of Formula 1 in the emission layer may be less than that of the compound of Formula 1000 above. That is, the amine-based compound of Formula 1 above may serve as a dopant, while the compound of Formula 1000 may serve as a host.

As used herein, “(for example, the organic layer) including at least one amine-based compound means that “(the organic layer) including one of the amine-based compounds of Formula 1 above, or at least two different amine-based compounds of Formula 1 above”.

In some embodiments, the organic layer may include only Compound 1 above as the amine-based compound. The Compound 1 may be in the EML layer of the organic light-emitting device. In some embodiments, the organic layer may include Compounds 1 and 2 as the amine-based compound. In this regard, Compounds 1 and 2 may be present in the same layer (for example, in the emission layer) or may be present in different layers.

The first electrode may be an anode as a hole injection electrode, while the second electrode may be a cathode as an electron injection electrode. In some embodiments, the first electrode may be a cathode as an electron injection electrode, while the second electrode may be a cathode as a hole injection electrode.

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

The term “organic layer” as used herein refers to a single layer and/or a plurality of layers disposed between the first and second electrodes of the organic light-emitting device. The “organic layer” may include an organic compound and an organic metal complex including metal.

FIG. 1 illustrates a schematic sectional view of an organic light-emitting device 10 according to an embodiment. Hereinafter, a structure of an organic light-emitting device according to an embodiment and a method of manufacturing the same will now be described with reference to FIG. 1. Referring to FIG. 1, the organic light-emitting device 10 has a structure in which a substrate 11, a first electrode 13, an organic layer 15, and a second electrode 17 are sequentially stacked in this order.

The substrate 11 may be any substrate that is used in existing organic light-emitting devices. In some embodiments the substrate 11 may be a glass substrate or a transparent plastic substrate with strong mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

The first electrode 13 may be formed by depositing or sputtering a first electrode-forming material on the substrate 11. The first electrode 13 may be an anode. A material for the first electrode 13 may be a material having a high work function to facilitate hole injection. The first electrode 13 may be a reflective electrode or a transmission electrode. The material for the first electrode 13 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), or zinc oxide (ZnO). The first electrode 13 may be formed as a reflective electrode from magnesium (Mg), aluminum (Al), aluminum—lithium (Al—Li), calcium (Ca), magnesium—indium (Mg—In), magnesium—silver (Mg—Ag), or the like.

The first electrode 13 may have a single-layer structure or a multi-layer structure including at least two layers. For example, the first electrode 13 may have a three-layered structure of ITO/Ag/ITO, but is not limited thereto.

The organic layer 15 may be disposed on the first electrode 13.

The organic layer 15 may include a hole transport region including a hole injection layer (HIL) and a hole transport layer (HTL) that are sequentially stacked upon one another; an emission layer (EML); and an electron transport region including an electron transport layer (ETL) and an electron injection layer (EIL) that are sequentially stacked upon one another.

The HIL may be formed on the first electrode 13 by any of a variety of methods, including vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, and the like.

When the HIL is formed using vacuum deposition, vacuum deposition conditions may vary according to the compound that is used to form the HIL, and the desired structure and thermal properties of the HIL to be formed. For example, vacuum deposition may be performed at a temperature of about 100° C. to about 500° C., a pressure of about 10⁻⁸torr to about 10⁻³torr, and a deposition rate of about 0.01 to about 100 Å/sec. However, the deposition conditions are not limited thereto.

When the HIL is formed using spin coating, the coating conditions may vary according to the compound that is used to form the HIL, and the desired structure and thermal properties of the HIL to be formed. For example, the coating rate may be in the range of about 2000 rpm to about 5000 rpm, and a temperature at which heat treatment is performed to remove a solvent after coating may be in the range of about 80° C. to about 200° C. However, the coating conditions are not limited thereto.

The HIL may be formed of any known hole injecting material. Non-limiting examples of materials for the HIL are N,N′-diphenyl-N,N′-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4′-diamine, (DNTPD), 4,4′,4″-tris (3-methylphenylphenylamino)triphenylamine (m-MTDATA), N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB), TDATA (refer to a formula below), 2-TNATA (refer to a formula below), polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (Pani/CSA), and polyaniline)/poly(4-styrenesulfonate (PANI/PSS).

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The thickness of the HIL may be about 100 Å to about 10000 Å, and in some embodiments, may be from about 100 Å to about 1000 Å. When the thickness of the HIL is within these ranges, the HIL may have good hole injecting ability without a substantial increase in driving voltage.

Then, a HTL may be formed on the HIL by using vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, or the like. When the HTL is formed using vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for the formation of the HIL, though the conditions for the deposition and coating may vary according to the material that is used to form the HTL.

Non-limiting examples of suitable known HTL forming materials are carbazole derivatives, such as N-phenylcarbazole or polyvinylcarbazole, N,N′-bis(3-methylphenyl)-N,N-diphenyl-[1,1-biphenyl]-4,4′-diamine (TPD), 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), and N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine) (NPB).

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The thickness of the HTL may be from about 50 Å to about 2000 Å, and in some embodiments, may be from about 100 Å to about 1500 Å. When the thickness of the HTL is within these ranges, the HTL may have good hole transporting ability without a substantial increase in driving voltage.

In some embodiments, at least one of the HIL and HTL may include at least one of a compound of Formula 300 below and a compound of Formula 301 below:

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In Formula 300, Ar₁₀₁and Ar₁₀₂may be each independently selected from

a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, and a pentacenylene group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxylic acid group or salt thereof, a sulfuric acid group or salt thereof, a phosphoric acid group or salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, and a C₂-C₆₀heteroaryl group.

In Formula 300, xa and xb may be each independently an integer from 0 to 5, for example, may be 0, 1, or 2. For example, xa may be 1, and xb may be 0, but are not limited thereto.

In Formulae 300 and 301, R₁₀₁to R₁₀₈, R₁₁₁to R₁₁₉, and R₁₂₁to R₁₂₄may be each independently selected from

a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₁₀alkyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, or a hexyl group), and a C₁-C₁₀alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, or a pentoxy group),

a C₁-C₁₀alkyl group and a C₁-C₁₀alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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,

a phenyl group, a naphthyl group, an anthracenylene group, a fluorenyl group, and a pyrenyl group, and

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₁₀alkyl group, and a C₁-C₁₀alkoxy group.

In Formula 300, R₁₀₉may be one of a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, a pyridyl group; and a phenyl group, a naphthyl group, an anthracenyl group, a biphenyl group, and a pyridyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₂₀alkyl group, and a substituted or unsubstituted C₁-C₂₀alkoxy group.

In an embodiment the compound of Formula 300 may be a compound represented by Formula 300A below:

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In Formula 300A, R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉may be as defined above.

In some embodiments, at least one of the HIL and HTL may include at least one of compounds represented by Formulae 301 to 320 below, but is not limited thereto:

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The hole transport region may further include a charge-generating material for improved layer conductivity, in addition to a widely-known hole injection material and a widely-known hole transport material.

The charge-generating material may be, for example, a p-dopant. The p-dopant may be one of quinine derivatives, metal oxides, and compounds with a cyano group, but are not limited thereto. Non-limiting examples of the p-dopant are quinone derivatives such as tetracyanoquinonedimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), and the like; metal oxides such as tungsten oxide, molybdenum oxide, and the like; and cyano-containing compounds such as Compound 200 below.

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When the hole transport region further includes such a charge-generating material as described above, the charge-generating material may be homogeneously dispersed or inhomogeneously distributed in the hole transport region.

The hole transport region may further include a buffer layer between the HTL and the EML.

The buffer layer may compensate for an optical resonance distance of light according to a wavelength of the light emitted from the EML, and thus may increase efficiency. The butter layer may include any hole injecting material or hole transporting material that are widely known. In some embodiments, the buffer layer may include the same material as one of the materials in the HTL underlying the buffer layer.

Subsequently, the EML may be formed on the hole transport region by using vacuum deposition, spin coating, casting, LB deposition, or the like. When the EML is formed using vacuum deposition or spin coating, the deposition and coating conditions may be similar to those for the formation of the HIL, though the conditions for deposition and coating may vary depending on the material used to form the EML.

The emission layer may include a host, and a dopant,

For example, the host may further include at least one of Alg₃, 4,4′-N,N′-dicarbazole-biphenyl (CBP), 9,10-di(naphthalene-2-yl)anthracene (DNA), TCTA (refer to a formula below), 1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), E3 (refer to a formula below), dmCBP (refer to a formula below), and Compounds 501 to 509 below.

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In some embodiments, the host may include an anthracene-based compound represented by Formula 400 below.

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In some embodiments, Ar₁₁₁and Ar₁₁₂in Formula 400 may be each independently selected from a phenylene group, a naphthylene group, a phenanthrenylene group, or a pyrenylene group; or a phenylene group, a naphthylene group, a phenanthrenylene group, a fluorenyl group, or a pyrenylene group, each substituted with at least one of a phenyl group, a naphthyl group, and an anthracenyl group, but are not limited thereto.

In Formula 400, Ar₁₁₃to Ar₁₁₆may be each independently selected from a C₁-C₁₀alkyl group; a phenyl group, a naphthyl group, a phenanthrenyl group, and a pyrenyl group; and a phenyl group, a naphthyl group, a phenanthrenyl group, a fluorenyl group, and a pyrenyl group, each substituted with at least one of a phenyl group, a naphthyl group, and an anthracenyl group.

In Formula 400, g, h, i, and j may be each independently an integer from 0 to 5, for example, may be 0, 1, or 2.

In Formula 400, Ar₁₁₃to Ar₁₁₆may be each independently selected from

a C₁-C₁₀alkyl group substituted with at least one of a phenyl group, a naphthyl group, and an anthracenyl group;

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

a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, and a fluorenyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, and a fluorenyl group; and

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but are not limited thereto.

For example, the anthracene-based compound of Formula 400 above may be one of the compounds represented by the following formulae, but is not limited thereto:

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In some embodiments, an anthracene-based compound represented by Formula 401 below may be used as the host.

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Ar₁₂₂to Ar₁₂₅in Formula 401 above may be defined as described above in conjunction with Ar₁₁₃of Formula 400, and thus detailed descriptions thereof will not be provided here.

Ar₁₂₆and Ar₁₂₇in Formula 401 above may be each independently a C₁-C₁₀alkyl group, for example, a methyl group, an ethyl group, or a propyl group.

In Formula 401, k and l may be each independently an integer from 0 to 4, for example, 0, 1, or 2.

For example, the anthracene compound of Formula 401 above may be one of the compounds represented by the following formulae, but is not limited thereto:

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When the organic light-emitting device is a full color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and a blue emission layer. In some embodiments, the EML may have a stack structure including a red emission layer, a green emission layer, and/or a blue emission layer that are stacked upon one another to emit white light, but is not limited thereto.

The EML of the light-emitting device may include a dopant, which may be a fluorescent dopant emitting light based on fluorescence mechanism, or a phosphorescent dopant emitting light based on phosphorescence mechanism. When the EML includes a fluorescent dopant, the fluorescent dopant may include the amine-based compound of Formula 1 above.

For full color emission, the organic light-emitting device may further include a known dopant, in addition to the amine-based compound of Formula 1 above. For example, the blue emission layer of the organic light-emitting device may include the amine-based compound of Formula 1 as a dopant, and the green and red emission layers may include a known phosphorescent dopant, which will be described below. However, embodiments are not limited thereto.

The known phosphorescent dopant may include an organometallic complex including a transition metal, for example, iridium (Ir), platinum (Pt), osmium (Os), or rhodium (Rh).

Non-limiting examples of the red dopant are compounds represented by the following formulae.

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Non-limiting examples of the green dopant are compounds represented by the following formulae.

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Non-limiting examples of known dopants that may be used in the EML are organometallic complexes represented by the following formulae.

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Non-limiting examples of dopants that may be used in the EML are organometallic complexes represented by the following formulae.

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When the EML includes both a host and a dopant, the amount of the dopant may be from about 0.01 to about 15 parts by weight based on 100 parts by weight of the host. However, the amount of the dopant is not limited to this range.

The thickness of the EML may be about 100 Å to about 1000 Å, and in some embodiments, may be from about 200 Å to about 600 Å. When the thickness of the EML is within these ranges, the EML may have good light emitting ability without a substantial increase in driving voltage.

Then, an ETL may be formed on the EML by vacuum deposition, spin coating, casting, or the like. When the ETL is formed using vacuum deposition or spin coating, the deposition and coating conditions may be similar to those for the formation of the HIL, though the deposition and coating conditions may vary according to a compound that is used to form the ETL.

A material for the ETL may be any known material that can stably transport electrons injected from an electron injecting electrode (cathode). Non-limiting examples of materials for the ETL are a quinoline derivative, such as tris(8-quinolinorate)aluminum (Alq₃), TAZ (refer to a formula below), BAlq (refer to a formula below), beryllium bis(benzoquinolin-10-olate (Bebq₂), 9,10-di(naphthalene-2-yl)anthracene (DNA, refer to a formula below), Compound 201, and Compound 202.

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The thickness of the ETL may be from about 100 Å to about 1,000 Å, and in some embodiments, may be from about 150 Å to about 500 Å. When the thickness of the ETL is within these ranges, the ETL may have satisfactory electron transporting ability without a substantial increase in driving voltage.

In some embodiments the ETL may further include a metal-containing material, in addition to the above-listed known electron-transporting organic compounds.

The metal-containing material may include a lithium (Li) complex. Non-limiting examples of the Li complex are lithium quinolate (LiQ) and Compound 203 below:

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In addition, the EIL, which facilitates injection of electrons from the second electrode (cathode) 17, may be formed on the ETL.

Non-limiting examples of materials for forming the EIL are LiF, NaCl, CsF, Li₂O, and BaO, which are known in the art. The deposition and coating conditions for forming the EIL may be similar to those for the formation of the HIL, though the deposition and coating conditions may vary depending on the material that is used to form the EIL.

The thickness of the EIL may be from about 1 Å to about 100 Å, and in some embodiments, may be from about 3 Å to about 90 Å. When the thickness of the EIL is within these ranges, the EIL may have satisfactory electron injection ability without a substantial increase in driving voltage.

The second electrode 17 is disposed on the organic layer 15. The second electrode 17 may be a cathode. A material for the second electrode 17 may be a metal, an alloy, or an electrically conductive compound, which have a low work function, or a combination thereof. Non-limiting examples of the material for the second electrode 17 are lithium (Li), magnesium (Mg), aluminum (Al), aluminum—lithium (Al—Li), calcium (Ca), magnesium—indium (Mg—In), and magnesium—silver (Mg—Ag), or the like. In some embodiments, to manufacture a top-emission light-emitting device, the second electrode 177 may be formed as a transmissive electrode from, for example, indium tin oxide (ITO) or indium zinc oxide (IZO).

Although the organic light-emitting device of FIG. 1 is described above, embodiments are not limited thereto.

For example, in the organic light-emitting device of FIG. 1, the first electrode 13 may be a cathode, and the second electrode 17 may be an anode. The electron transport region may be disposed between the first electrode 13 and the EML and the hole transport region may be disposed between the EML and the second electrode 17. However, embodiments are not limited thereto.

A hole blocking layer (HBL) may be formed between the EML and the ETL by using vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, or the like, in order to prevent diffusion of triplet excitons or holes into the ETL. When the HBL is formed using vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for the formation of the HIL, although the conditions for deposition and coating may vary according to the material that is used to form the HBL. Any known hole-blocking material may be used. Non-limiting examples of hole-blocking materials are oxadiazole derivatives, triazole derivatives, and phenanthroline derivatives. For example, bathocuproine (BCP) represented by the following formula may be used as a material for forming the HBL.

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The thickness of the HBL may be from about 20 Å to about 1000 Å, and in some embodiments, may be from about 30 Å to about 300 Å. When the thickness of the HBL is within these ranges, the HBL may have improved hole blocking ability without a substantial increase in driving voltage.

As used herein, a C₁-C₆₀alkyl group may be a linear or branched C₁-C₆₀alkyl group, including, for example, a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a pentyl group, an iso-amyl group, and a hexyl group. A C₁-C₆₀alkylene group refers to a divalent group having the same structure as the C₁-C₆₀alkyl group.

As used herein, a C₁-C₆₀alkoxy group refer to a moiety represented by —OA (where A is a C₁-C₆₀alkyl group). Non-limiting examples of the C₁-C₆₀alkoxy group are a methoxy group, an ethoxy group, and an isopropyloxy group.

As used herein, a C₂-C₆₀alkenyl group refers to a moiety with at least one carbon double bond in the middle or at a terminal of thereof. Non-limiting examples of the C₂-C₆₀alkenyl group are an ethenyl group, a propenyl group, and a butenyl group. A C₂-C₆₀alkenylene group refers to a divalent group having the same structure as the C₁-C₆₀alkenyl group.

As used herein, a C₂-C₆₀alkynyl group refers to a moiety with at least one carbon-carbon triple bond in the middle or at a terminal thereof. Non-limiting examples of the C₂-C₆₀alkynyl group are an ethenyl group and a propynyl group. A C₂-C₆₀alkynylene group refers to a divalent group having the same structure as the C₁-C₆₀alkynyl group.

As used herein, a C₃-C₁₀cycloalkyl group refers to a cyclic alkyl group including 3 to 10 carbon atoms. Non-limiting examples of the C₃-C₁₀cycloalkyl group are a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. A C₃-C₁₀cycloalkylene group refers to a divalent group having the same structure as the C₃-C₁₀cycloalkyl group.

As used herein, a C₃-C₁₀heterocycloalkyl group refers to a C₃-C₁₀cycloalkyl group including at least one heteroatom of N, S, O, or P. Non-limiting examples of the C₃-C₁₀heterocycloalkyl group are a tetrahydrofuranyl group and a tetrahydrothiophenyl group. A C₃-C₁₀heterocycloalkylene group refers to a divalent group having the same structure as the C₃-C₁₀heterocycloalkyl group.

As used herein, a C₃-C₁₀cycloalkenyl group refers to a cyclic alkenyl group including 3 to 10 carbon atoms. Non-limiting examples of the C₃-C₁₀cycloalkenyl group are a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. A C₃-C₁₀cycloalkenylene group refers to a divalent group having the same structure as the C₃-C₁₀cycloalkenyl group.

As used herein, a C₃-C₁₀heterocycloalkenyl group refers to a C₃-C₁₀cycloalkenyl group with at least one heteroatom of N, S, O, or P. Non-limiting examples of the C₃-C₁₀heterocycloalkenyl group are a 2,3-dihydrofuranyl group and a 2,3-dihydrothiophenyl group. A C₃-C₁₀heterocycloalkenylene group refers to a divalent group having the same structure as the C₃-C₁₀heterocycloalkenyl group.

As used herein, a C₆-C₆₀aryl group refers to a monovalent carbocyclic aromatic system including 6 to 60 carbon atoms and at least one aromatic ring. A C₆-C₆₀arylene group refers to a divalent group having the same structure as the C₆-C₆₀aryl group. When the C₆-C₆₀aryl group and the C₆-C₆₀arylene group have at least two rings, the at least two rings may be fused together.

Non-limiting examples of the “C₆-C₆₀aryl group” and “a C₆-C₆₀aryl group substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₃-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₂-C₆₀heteroaryl group, —N(Q₁₁)(Q₁₂), and —Si(Q₁₃)(Q₁₄)(Q₁₅)” are a phenyl group, a C₁-C₁₀alkylphenyl group (for example, an ethylphenyl group), a C₁-C₁₀alkylbiphenyl group (for example, an ethylbiphenyl group), a halophenyl group (for example, o-, m-, or p-fluorophenyl group, or a dichlorophenyl group), a dicyanophenyl group, a trifluoromethoxyphenyl group, o-, m-, and p-tolyl group, o-, m- and p-cumenyl group, a mesityl group, a phenoxyphenyl group (α,α-dimethylbenzene), a phenyl group, a (N,N′-dimethyl)aminophenyl group, a N,N′-diphenyl)aminophenyl group, a pentalenyl group, an indenyl group, a naphthyl group, a halonaphthyl group (for example, a fluoronaphthyl group), a C₁-C₁₀alkylnaphthyl group (for example, a methylnaphthyl group), a C₁-C₁₀alkoxynaphthyl group (for example, a methoxynaphthyl group), an anthracenyl group, an azulenyl group, a heptalenyl group, an acenaphthyl group, a phenalenyl group, a fluorenyl group, a methylanthracenyl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, an ethyl-chrysenyl group, a picenyl group, a perylenyl group, a chloroperylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenylenyl group, a hexaphenyl group, a hexacenyl group, a rubicenyl group, a coronenyl group, a trinaphthylenyl group, a heptaphenyl group, a heptacenyl group, a pyranthrenyl group, and an ovalenyl group.

As used herein, a C₂-C₆₀heteroaryl group refers to a monovalent carbocyclic group having at least one aromatic ring having at least one of the heteroatoms selected from N, O, P, and S. A C₂-C₆₀heteroarylene group refers to a divalent group having the same structure as the C₂-C₆₀heteroaryl group. When the C₂-C₆₀heteroaryl group and the C₂-C₆₀heteroarylene group have at least two rings, the at least two rings may be fused together.

Non-limiting examples of the C₂-C₆₀heteroaryl group are a pyrazolyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a pyridinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a carbazolyl group, an indolyl group, a quinolinyl group, an isoquinolinyl group, a benzoimidazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group.

As used herein, a C₆-C₆₀aryloxy group indicates —OA₂(where A₂is a C₆-C₆₀aryl group described above), and a C₆-C₆₀arylthio group indicates —SA₃(where A₃is a C₆-C₆₀aryl group described above).

Hereinafter, embodiments will be described in detail with reference to the following synthesis examples and other examples. However, these examples are for illustrative purposes only and are not intended to limit the scope. The use of, for example, “B” instead of “A” in the following synthesis examples means that the amounts of “B” and “A” in mole equivalent are also equal to each other.

The following Examples and Comparative Examples are provided in order to highlight characteristics of one or more embodiments, but it will be understood that the Examples and Comparative Examples are not to be construed as limiting the scope of the embodiments, nor are the Comparative Examples to be construed as being outside the scope of the embodiments. Further, it will be understood that the embodiments are not limited to the particular details described in the Examples and Comparative Examples.

EXAMPLES
Synthesis Example 1
Synthesis of Compound 1

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Synthesis of Intermediate I-2

160.5 mg (0.175 mmol) of Pd₂(dba)₃and 70.9 mg (0.350 mmol) of t-Bu₃P were dissolved in 50 mL of o-xylene, and then stirred at room temperature for about 10 minutes. 5 g (17.52 mmol) of 2,3-diphenylbenzofuran-6-amine (Intermediate I-1), 3.9 g (19.28 mmol) of iodobenzene, and 1.01 g (10.51 mmol) of t-BuONa were added into the mixture and refluxed at about 160° C. for about 48 hours while stirring. After completion of the reaction, 20 mL of cool distilled water was added into the reaction product, followed by extraction with ethylacetate, drying with magnesium sulfate, filtering, and removing the solvent. The resulting product was purified by column chromatography to obtain 4.82 g of Intermediate I-2 (N,2,3-triphenylbenzofuran-6-amine) (Yield: 76%).

Synthesis of Compound 1

76.3 mg (0.083 mmol) of Pd₂(dba)₃and 33.7 mg (0.167 mmol) of t-Bu₃P were dissolved in 30 mL of o-xylene, and then stirred at room temperature for about 10 minutes. 3 g (8.33 mmol) of 1,6-dibromopyrene, 3.3 g (9.17 mmol) of Intermediate I-2, and 480 mg (5.00 mmol) of t-BuONa were added into the mixture and refluxed at about 160° C. for about 48 hours while stirring. After completion of the reaction, 20 mL of cool distilled water was added into the reaction product, followed by extraction with ethylacetate, drying with magnesium sulfate, filtering, and removing the solvent. The resulting product was purified by column chromatography to obtain 5.64 g of Compound 1 (N1,N6-bis(2,3-diphenylbenzofuran-6-yl)-N1,N6-diphenylpyrene-1,6-diamine) (Yield: 73%).

¹H NMR (300 MHz, a CDCl₃), d (ppm): 8.99-8.87 (4H, m), 8.32-8.26 (2H, d), 8.26-8.20 (2H, m), 8.03-7.97 (2H, d), 7.95-7.85 (6H, m), 7.75-7.68 (2H, m), 7.63-7.48 (10H, m), 7.47-7.36 (6H, m), 7.31-7.23 (4H, t), 7.19-7.10 (4H, m), 7.01-6.93 (2H, m).

EI-MS, m/e, calcd for C₆₈H₄₄N₂O₂920.34. found 920.38.

Synthesis Example 2
Synthesis of Compound 2

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Synthesis of Intermediate I-3

5.68 g (Yield 74%) of Intermediate I-3 (N-([1,1′-biphenyl]-4-yl)-2,3-diphenylbenzofuran-6-amine) was obtained in the same manner as in the synthesis of Intermediate I-2 in Synthesis Example 1, except that 5.4 g (19.28 mmol) of 4-iodo-1,1′-biphenyl, instead of iodobenzene, was used.

Synthesis of Compound 2

6.48 g (Yield 72%) of Compound 2 (N1,N6-di([1,1′-biphenyl]-4-yl)-N1,N6-bis(2,3-diphenylbenzofuran-6-yl)pyrene-1,6-diamine) was obtained in the same manner as in the synthesis of Compound 1 in Synthesis Example 1, except that 4.0 g (9.17 mmol) of Intermediate I-3, instead of Intermediate I-2, was used.

¹H NMR (300 MHz, a CDCl₃), d (ppm): 9.00-8.90 (4H, m), 8.69-8.59 (4H, m), 8.44-8.37 (2H, d), 8.26-8.20 (2H, m), 8.14-8.07 (2H, m), 8.00-7.94 (4H, d), 7.93-7.86 (4H, m), 7.65-7.55 (10H, m), 7.55-7.48 (4H, t), 7.48-7.34 (10H, m), 7.32-7.25 (2H, m), 7.22-7.12 (4H, m).

EI-MS, m/e, calcd for C₈₀H₅₂N₂O₂1072.40. found 1072.46.

Synthesis Example 3
Synthesis of Compound 3

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Synthesis of Intermediate I-4

5.26 g (Yield 68%) of Intermediate I-4 (2,3-diphenyl-N-(4-(pyridin-4-yl)phenyl)benzofuran-6-amine) was obtained in the same manner as in the synthesis of Intermediate I-2 in Synthesis Example 1, except that 5.4 g (19.28 mmol) of 4-(4-iodophenyl)pyridine, instead of iodobenzene, was used.

Synthesis of Compound 3

6.82 g (Yield 76%) of Compound 3 (N1,N6-bis(2,3-diphenylbenzofuran-6-yl)-N1,N6-bis(4-(pyridin-4-yl)phenyl)pyrene-1,6-diamine) was obtained in the same manner as in the synthesis of Compound 1 in Synthesis Example 1, except that 4.0 g (9.17 mmol) of Intermediate I-4, instead of Intermediate I-2, was used.

¹H NMR (300 MHz, a CDCl₃), d (ppm): 9.00-8.92 (4H, m), 8.89-8.82 (4H, d), 8.53-8.47 (4H, d), 8.43-8.37 (2H, d), 8.22-8.17 (2H, m), 8.12-8.06 (2H, m), 7.96-7.87 (8H, m), 7.64-7.55 (6H, m), 7.54-7.48 (4H, t), 7.48-7.38 (4H, m), 7.38-7.33 (4H, d), 7.31-7.26 (2H, m), 7.22-7.13 (4H, m).

EI-MS, m/e, calcd for C₇₈H₅₀N₄O₂1074.39. found 1074.43.

Synthesis Example 4
Synthesis of Compound 16

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Synthesis of Intermediate I-6

4.86 g (Yield 69%) of Intermediate I-6 (N-(naphthalen-2-yl)-2,3-diphenylbenzo[b]thiophen-6-amine) was obtained in the same manner as in the synthesis of Intermediate I-2 in Synthesis Example 1, except that 5 g (16.59 mmol) of 2,3-diphenylbenzo[b]thiophen-6-amine (Intermediate I-5) and 4.6 g (18.25 mmol) of 2-iodonaphthalene, instead of 2,3-diphenylbenzofuran-6-amine and iodobenzene, respectively, were used.

Synthesis of Compound 16

6.97 g (Yield 79%) of Compound 16 (N1,N6-bis(2,3-diphenylbenzo[b]thiophen-6-yl)-N1,N6-di(naphthalen-2-yl)pyrene-1,6-diamine) was obtained in the same manner as in the synthesis of Compound 1 in Synthesis Example 1, except that 3.9 g (9.17 mmol) of Intermediate I-6, instead of Intermediate I-2, was used.

¹H NMR (300 MHz, a CDCl₃), d (ppm): 9.08-9.01 (2H, m), 8.70-8.64 (2H, d), 8.33-8.24 (2H, m), 8.19-8.09 (6H, m), 8.04-7.95 (6H, m), 7.92-7.85 (2H, m), 7.81-7.72 (6H, m), 7.65-7.60 (2H, d), 7.60-7.47 (10H, m), 7.44-7.34 (4H, m), 7.33-7.29 (2H, m), 7.29-7.23 (2H, d), 7.22-7.15 (2H, m).

EI-MS, m/e, calcd for C₇₆H₄₈N₂S₂1052.33. found 1052.36.

Synthesis Example 5
Synthesis of Compound 37

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Synthesis of Intermediate I-7

4.74 g (Yield 76%) of Intermediate I-7 (N,2,3-triphenylbenzo[b]thiophen-6-amine) was obtained in the same manner as in the synthesis of Intermediate I-4 in Synthesis Example 4, except that 3.7 g (18.25 mmol) of iodobenzene, instead of 2-iodonaphthalene, was used.

Synthesis of Compound 37

5.68 g (Yield 85%) of Compound 37 (N,N′-(anthracene-9,10-diylbis(4,1-phenylene))bis(N,2,3-triphenylbenzo[b]thiophen-6-amine)) was obtained in the same manner as in the synthesis of Compound 16 in Synthesis Example 4, except that 3 g (6.14 mmol) of 9,10-bis(4-bromophenyl)anthracene) and 2.6 g (6.76 mmol) of Intermediate I-7, instead of 1,6-dibromopyrene and Intermediate I-6, respectively, were used.

¹H NMR (300 MHz, a CDCl₃), d (ppm): 9.91-9.79 (4H, m), 8.11-8.02 (2H, d), 7.99-7.92 (4H, m), 7.92-7.86 (2H, d), 7.86-7.79 (4H, m), 7.58-7.53 (4H, t), 7.52-7.48 (4H, d), 7.47-7.37 (14H, m), 7.36-7.29 (2H, m), 7.14-7.07 (4H, t), 7.06-6.99 (4H, m), 6.87-6.79 (2H, m).

EI-MS, m/e, calcd for C₇₈H₅₂N₂S₂1080.36. found 1080.42.

Synthesis Example 6
Synthesis of Compound 64

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5.82 g (Yield 86%) of Compound 64 (N2,N7-bis(2,3-diphenylbenzo[b]thiophen-6-yl)-N2,N7,9,9-tetraphenyl-9H-fluorene-2,7-diamine) was obtained in the same manner as in the synthesis of Compound 37 in Synthesis Example 5, except that 3 g (6.29 mmol) of 2,7-dibromo-9,9-diphenyl-9H-fluorene, instead of 1,6-dibromopyrene, was used.

¹H NMR (300 MHz, a CDCl₃), d (ppm): 9.89-9.81 (2H, d), 8.14-8.09 (2H, m), 7.82-7.72 (8H, m), 7.71-7.66 (2H, m), 7.59-7.55 (2H, m), 7.50-7.42 (10H, m), 7.40-7.20 (18, m), 7.18-7.12 (4H, m), 7.12-7.07 (2H, m), 6.99-6.93 (2H, m).

EI-MS, m/e, calcd for C₇₇H₅₂N₂S₂1068.36. found 1068.41

Synthesis Example 7
Synthesis of Compound 82

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5.42 g (Yield 74%) of Compound 82 (N6,N12-bis(2,3-diphenylbenzofuran-6-yl)-N6,N12-diphenylchrysene-6,12-diamine) was obtained in the same manner as in the synthesis of Compound 1 in Synthesis Example 1, except that 3 g (7.77 mmol) of 6,12-dibromochrysene, instead of 1,6-dibromopyrene, was used, and the amount of Intermediate I-2 was changed to 3.1 g (8.55 mmol).

¹H NMR (300 MHz, a CDCl₃), d (ppm): 8.77-8.70 (2H, m), 8.53-8.44 (4H, m), 8.06-7.99 (4H, m), 7.83-7.78 (2H, m), 7.77-7.59 (14H, m), 7.57-7.50 (4H, m), 7.49-7.41 (2H, m), 7.28-7.19 (4H, t), 7.15-7.06 (4H, m), 6.99-6.89 (4H, m), 6.42-6.34 (2H, m).

EI-MS, m/e, calcd for C₇₀H₄₆N₂O₂946.36. found 946.36

Synthesis Example 8
Synthesis of Compound 91

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5.84 g (Yield 76%) of Compound 91 (N6,N12-bis(2,3-diphenylbenzofuran-6-yl)-N6,N12-diphenylchrysene-6,12-diamine) was obtained in the same manner as in the synthesis of Compound 37 in Synthesis Example 5, except that 3 g (7.77 mmol) of 6,12-dibromochrysene, instead of 1,6-dibromopyrene, was used, and the amount of Intermediate I-7 was changed to 3.2 g (8.54 mmol).

¹H NMR (300 MHz, a CDCl³), d (ppm): 8.85-8.76 (2H, m), 8.19-8.11 (4H, m), 8.00-7.93 (4H, m), 7.84-7.75 (6H, m), 7.75-7.66 (4H, m), 7.52-7.42 (10H, m), 7.42-7.31 (6H, m), 7.29-7.21 (4H, m), 7.17-7.10 (4H, m), 6.99-6.90 (2H, m).

EI-MS, m/e, calcd for C₇₀H₄₆N₂S₂978.31. found 978.38.

Example 1

To manufacture an anode, a corning 15 Ω/cm²(1200 Å) ITO glass substrate was cut to a size of 50 mm×50 mm×0.7 mm and then sonicated in isopropyl alcohol and pure water each for five minutes, and then cleaned by irradiation of ultraviolet rays for 30 minutes and exposure to ozone. The resulting glass substrate was loaded into a vacuum deposition device.

2-TNATA was vacuum-deposited on the ITO anode to form an HIL having a thickness of 600 Å on the anode, and then 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) was vacuum-deposited on the HIL to form a HTL having a thickness of 300 Å.

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ADN (host) and Compound 1 (dopant) were co-deposited in a weight ratio of about 98:2 on the HTL to form an EML having a thickness of about 400 Å, followed by depositing Alg₃on the EML to form an ETL having a thickness of about 300 Å. LiF was deposited on the ETL to form an EIL having a thickness of about 10 Å, and Al was deposited on the EIL to form a cathode having a thickness of about 3000 Å, thereby completing the manufacture of an organic light-emitting device.

Example 2

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2, instead of Compound 1, was used as a dopant in forming the EML.

Example 3

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 3, instead of Compound 1, was used as a dopant in forming the EML.

Example 4

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 16, instead of Compound 1, was used as a dopant in forming the EML.

Example 5

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 37, instead of Compound 1, was used as a dopant in forming the EML.

Example 6

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 64, instead of Compound 1, was used as a dopant in forming the EML.

Example 7

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 82, instead of Compound 1, was used as a dopant in forming the EML.

Example 8

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 91, instead of Compound 1, was used as a dopant in forming the EML.

Comparative Example 1

An organic light-emitting device was manufactured in the same manner as in Example 1, except that DPVBi, instead of Compound 1, was used as a dopant in forming the EML.

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Comparative Example 2

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound A below, instead of Compound 1, was used as a dopant in forming the EML.

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Comparative Example 3

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound B below, instead of Compound 1, was used as a dopant in forming the EML.

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Comparative Example 4

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound C below, instead of Compound 1, was used as a dopant in foaming the EML.

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Comparative Example 5

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound D below, instead of Compound 1, was used as a dopant in forming the EML.

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Comparative Example 6

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound E below, instead of Compound 1, was used as a dopant in forming the EML.

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Evaluation Example 1
Characteristics Evaluation of Organic Light-Emitting Devices

Efficiencies and color purities of the organic light-emitting devices of Examples 1 to 8 and Comparative Examples 1 to 6 were measured using a voltage source-measure unit (Kethley SMU 236) as a power supply and a PR650 (Spectroscan) Source Measurement Unit (available from Photo Research, Inc.). The results are shown in Table 1.

TABLE 1

Current

density
Emission
Color

(mA/
efficiency
coordinates

Example
Host
Dopant
cm²)
(cd/A)
CIE x
CIE y

Example 1
ADN
Compound 1
10
7.2
0.14
0.12

Example 2
ADN
Compound 2
10
6.7
0.15
0.11

Example 3
ADN
Compound 3
10
6.9
0.14
0.12

Example 4
ADN
Compound 16
10
7.1
0.15
0.13

Example 5
ADN
Compound 37
10
7.5
0.15
0.11

Example 6
ADN
Compound 64
10
6.8
0.15
0.10

Example 7
ADN
Compound 82
10
6.6
0.14
0.11

Example 8
ADN
Compound 91
10
7.1
0.15
0.12

Comparative
ADN
DPVBi
10
4.3
0.15
0.20

Example 1

Comparative
ADN
Compound A
10
4.1
0.15
0.21

Example 2

Comparative
ADN
Compound B
10
4.4
0.14
0.19

Example 3

Comparative
ADN
Compound C
10
4.3
0.15
0.22

Example 4

Comparative
ADN
Compound D
10
4.5
0.15
0.21

Example 5

Comparative
ADN
Compound E
10
4.4
0.15
0.24

Example 6

Referring to Table 1, the organic light-emitting devices of Examples 1 to 8 were found to have improved emission efficiencies and improved color purities, compared to the organic light-emitting devices of Comparative Examples 1 to 6.

As described above, according to the one or more embodiments, an amine-based compound of Formula 1 above may have improved electrical characteristics and improved thermal stability. Accordingly, an organic light-emitting device including the amine-based compound may have improved emission efficiency and improved color purity characteristics.

Example embodiments have been disclosed herein, and although specific terms are employed, they are used and are to be interpreted in a generic and descriptive sense only and not for purpose of limitation. In some instances, as would be apparent to one of ordinary skill in the art as of the filing of the present application, features, characteristics, and/or elements described in connection with a particular embodiment may be used singly or in combination with features, characteristics, and/or elements described in connection with other embodiments unless otherwise specifically indicated. Accordingly, it will be understood by those of skill in the art that various changes in form and details may be made without departing from the spirit and scope thereof as set forth in the following claims.

Claims

1. An amine-based compound represented by Formula 1 below:
2. The amine-based compound as claimed in claim 1, wherein A1 is selected from a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, and a benzofluoranthenylene group, anda naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, and a benzofluoranthenylene group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group.
3. The amine-based compound as claimed in claim 1, wherein X1 and X2 are both S, or X1 and X2 are both O.
4. The amine-based compound as claimed in claim 1, wherein L1, L2, L11, L12, L21, and L22 are each independently selected from a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pyrrolylene group, an imidazolylene group, a pyrazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a carbazolylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzooxazolylene group, a benzoimidazolylene group, a furanylene group, a benzofuranylene group, a thiophenylene group, a benzothiophenylene group, a thiazolylene group, an isothiazolylene group, a benzothiazolylene group, an isoxazolylene group, an oxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, and a dibenzocarbazolylene group, and a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pyrrolylene group, an imidazolylene group, a pyrazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a carbazolylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzooxazolylene group, a benzoimidazolylene group, a furanylene group, a benzofuranylene group, a thiophenylene group, a benzothiophenylene group, a thiazolylene group, an isothiazolylene group, a benzothiazolylene group, an isoxazolylene group, an oxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, and a dibenzocarbazolylene group, each substitute with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group.
5. The amine-based compound as claimed in claim 1, wherein L1, L2, L11, L12, L21, and L22 are each independently selected from the groups represented by Formulae 2-1 to 2-30 below:
6. The amine-based compound as claimed in claim 1, wherein L1, L2, L11, L12, L21, and L22 are each independently selected from the groups represented by Formulae 3-1 to 3-19 below:
7. The amine-based compound as claimed in claim 1, wherein a1, a2, a11, a12, a21, and a22 are each independently 0, 1, or 2.
8. The amine-based compound as claimed in claim 1, wherein R1, R2, R11, and R12 are each independently selected from 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 phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthrenyl 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 pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzooxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a benzooxazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group, anda 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 phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthrenyl 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 pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzooxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a benzocarbazolyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group.
9. The amine-based compound as claimed in claim 1, wherein R3 to R6 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C1-C20 alkyl group, and a C1-C20 alkoxy group;a C1-C20 alkyl group and a C1-C60 alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl 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, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthrenyl 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 pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzooxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a benzooxazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl 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, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthrenyl 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 pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzooxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a benzocarbazolyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group; and—N(Q1)(Q2), and —Si(Q3)(Q4)(Q5), wherein Q1 to Q5 are each independently selected froma hydrogen atom, a C1-C20 alkyl group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group; anda phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group.
10. The amine-based compound as claimed in claim 1, wherein R1, R2, R11, and R12 are each independently selected from the groups represented by Formulae 4-1 to 4-29 below; and R3 to R6 are each independently selected froma hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C1-C20 alkyl group, and a C1-C20 alkoxy group,a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group,the groups represented by Formulae 4-1 to 4-29 below, and—N(Q1)(Q2) and —Si(Q3)(Q4)(Q5), wherein Q1 to Q5 are each independently selected froma hydrogen atom, a C1-C20 alkyl group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group; anda phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group:
11. The amine-based compound as claimed in claim 1, wherein R1, R2, R11, and R12 are each independently selected from the groups represented by Formulae 5-1 to 5-36 below; and R3 to R6 are each independently selected froma hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C1-C20 alkyl group, and a C1-C20 alkoxy group,a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group,the groups represented by Formulae 5-1 to 5-36 below, and—N(Q1)(Q2), and —Si(Q3)(Q4)(Q5), wherein Q1 to Q5 are each independently selected froma hydrogen atom, a C1-C20 alkyl group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group; anda phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and a quinazolinyl group:
12. The amine-based compound as claimed in claim 1, wherein the amine-based compound of Formula 1 is a compound represented by Formula 1A below:
13. The amine-based compound as claimed in claim 1, wherein the amine-based compound of Formula 1 is a compound represented by one of Formulae 1A(1) to 1A(4) below:
14. The amine-based compound as claimed in claim 1, wherein the amine-based compound of Formula 1 is one of Compounds 1 to 108 below:
15. An organic light-emitting device, comprising: a first electrode;a second electrode; andan organic layer disposed between the first electrode and the second electrode, and including an emission layer and at least one of the amine-based compounds of claim 1.
16. The organic light-emitting device as claimed in claim 15, wherein the first electrode is an anode, the second electrode is a cathode, and the organic layer includes i) a hole transport region disposed between the first electrode and the emission layer and including at least one of a hole injection layer, a hole transport layer, and an electron blocking layer, and ii) an electron transport region disposed 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.
17. The organic light-emitting device as claimed in claim 15, wherein the organic layer further includes a compound represented by Formula 1000 below: Y1−A2−Y2 <Formula 1000>wherein, in Formula 1000, A2 is selected froma pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, and a benzofluoranthenylene group, anda pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, and a benzofluoranthenylene group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, —N(Q11)(Q12), and —Si(Q13)(Q14)(Q15);Y1 and Y2 are each independently selected froma C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C2-C60 heteroaryl group, anda C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C2-C60 heteroaryl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and —N(Q101)(Q102); andQ101 and Q102 are each independently selected froma hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, anda C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C60 alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C2-C60 heteroaryl group,a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C2-C60 heteroaryl group, anda C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C2-C60 heteroaryl group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C2-C60 heteroaryl group.
18. The organic light-emitting device as claimed in claim 15, wherein the amine-based compound is in the emission layer.
19. The organic light-emitting device as claimed in claim 17, wherein the amine-based compound and the compound of Formula 1000 are both in the emission layer, and an amount of the amine-based compound in the emission layer is less than that of the compound of Formula 1000.
20. The organic light-emitting device as claimed in claim 16, wherein the hole transport region includes at least one of a compound represented by Formula 300 below and a compound represented by Formula 301 below:

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Number	Date	Country	Kind
10-2013-0072718	Jun 2013	KR	national

AMINE-BASED COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME

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