CONDENSED CYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME

TECHNICAL FIELD

One or more embodiments of the present disclosure relate to a condensed cyclic compound, and an organic light-emitting device including the same.

BACKGROUND ART

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

An organic light-emitting device may include an anode, a cathode, and an organic layer including an emission layer and 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 the 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.

DISCLOSURE
Technical Problem

One or more embodiments of the present disclosure include a novel condensed cyclic compound, and an organic light-emitting device including the same.

The light-emitting device includes different compounds from each other, for example as hosts, and thus has a lower driving voltage, high efficiency, high luminance and long life-span characteristics.

The compound is used in an electron transport auxiliary layer to provide a light-emitting device having a lower driving voltage, high efficiency, high luminance and long life-span characteristics.

Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments.

Technical Solution

According to one or more embodiments of the present disclosure, there is provided a condensed cyclic compound represented by Formula 1:

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wherein, in Formula 1, ring A₁is represented by Formula 1A, where X₁is N-[(L₁)_a1-(R₁)_b1], S, O, or Si(R₄)(R₅);

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L₁to L₃are each independently selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₂-C₆₀heteroarylene group, and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, wherein L₂and L₃are not a substituted or unsubstituted carbazolylene group,

a1 to a3 are each independently an integer selected from 0 to 5,

R₁to R₅are each independently selected from a hydrogen, a deuterium, a fluoro group (—F), a chloro group (—Cl), a bromo group (—Br), an iodo group (—I), a hydroxyl group, a cyano group, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₂-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇), wherein at least one of R₂and R₃is a substituted or unsubstituted N-containing C₂-C₆₀heteroaryl group,

R₁₁to R₁₄are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a monovalent non-aromatic condensed polycyclic group, —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇), and

b1 to b3 are each independently an integer selected from 1 to 3,

wherein R₃is not a substituted or unsubstituted morpholinyl group;

when R₃is a pyridinyl group, pyridazinyl group, or a pyrimidinyl group, R₂is selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, and a substituted or unsubstituted triphenylenyl group;

at least one of substituents of the substituted C₃-C₁₀cycloalkylene group, the substituted C₃-C₁₀cycloalkenylene group, the substituted C₆-C₆₀arylene group, the substituted C₂-C₆₀heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₁-C₆₀alkoxy group, the substituted C₃-C₁₀cycloalkyl group, the substituted C₂-C₁₀heterocycloalkyl group, the substituted C₆-C₆₀aryl group, the substituted C₆-C₆₀aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₂-C₆₀heteroaryl group, and the substituted monovalent non-aromatic condensed polycyclic group is selected from

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₆₀alkyl group, and a C₁-C₆₀alkoxy group,

a C₁-C₆₀alkyl group, and a C₁-C₆₀alkoxy group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, —Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇),

a C₃-C₁₀cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₂-C₆₀heteroaryl group, and a monovalent non-aromatic condensed polycyclic group,

a C₃-C₁₀cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₂-C₆₀heteroaryl group, and a monovalent non-aromatic condensed polycyclic group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₆₀alkyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, —Si(Q₂₃)(Q₂₄)(Q₂₅), and —B(Q₂₆)(Q₂₇), and

—Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇);

Q₃to Q₇, Q₁₃to Q₁₇, Q₂₃to Q₂₇, and Q₃₃to Q₃₇are each independently selected from a hydrogen, a C₁-C₆₀alkyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₂-C₆₀heteroaryl group, and a monovalent non-aromatic condensed polycyclic group; and

a substituent of R₂and R₃is not a carbazolyl group substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₆₀alkyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, —Si(Q₂₃)(Q₂₄)(Q₂₅), and —B(Q₂₆)(Q₂₇).

According to one or more embodiments of the present disclosure, 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 wherein the organic layer includes the condensed cyclic compounds of Formula 1 defined above.

The at least one of the condensed cyclic compounds of Formula 1 may be in the emission layer of the organic layer or electron transport auxiliary layer, and the emission layer may further include a dopant. The at least one of the condensed cyclic compounds of Formula 1 in the emission layer may serve as a host.

According to one or more embodiments of the present disclosure, an organic light-emitting device includes an organic layer including i) a condensed cyclic compound and at least one of ii) a first compound represented by Formula 41 and a second compound represented by the following Formula 61.

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In Formula 41, X₄₁is N-[(L₄₂)_a42-(R₄₂)_b42], S, O, S(═O), S(═O)₂, C(═O), C(R₄₃)(R₄₄), Si(R₄₃)(R₄₄), P(R₄₃), P(═O)(R₄₃) or C═N(R₄₃);

the ring A₆₁is represented by Formula 61A;

in Formula 61, the ring A₆₂is represented by Formula 61B;

X₆₁is N-[(L₆₂)_a62-(R₆₂)_b62], S, O, S(═O), S(═O)₂, C(═O), C(R₆₃)(R₆₄), Si(R₆₃)(R₆₄), P(R₆₃), P(═O)(R₆₃) or C═N(R₆₃);

X₇₁is C(R₇₁) or N, X₇₂is C(R₇₂) or N, X₇₃is C(R₇₃) or N, X₇₄is C(R₇₄) or N, X₇₅is C(R₇₅) or N, X₇₆is C(R₇₆) is N, X₇₇is C(R₇₇) or N, and X₇₈is C(R₇₈) or N;

Ar₄₁, L₄₁, L₄₂, L₆₁and L₆₂are each independently a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₂-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₂-C₁₀hetero cycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₂-C₆₀heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group or a substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic group;

n1 and n2 are each independently an integer selected from 0 to 3;

a41, a42, a61 and a62 are each independently an integer selected from 0 to 5;

R₄₁to R₄₄, R₅₁to R₅₄, R₆₁to R₆₄and R₇₁to R₇₉are each independently hydrogen, deuterium, —F (a fluoro group), —Cl (a chloro group), —Br (a bromo group), —I (an iodo group), a hydroxyl group, a cyano group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid 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-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₂-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅) or —B(Q₆)(Q₇); and

b41, b42, b51 to b54, b61, b62 and b79 are each independently an integer selected from 1 to 3.

Advantageous Effects

The condensed cyclic compound has a good electrical charicteristics and a thermal stability, and thus the organic layer including the condensed cyclic compound of Formula 1 described above, the organic light-emitting device may have a low driving voltage, a high efficiency, and a long lifetime.

DESCRIPTION OF THE DRAWINGS

FIGS. 1 to 3 are schematic views of an organic light-emitting device according to an embodiment of the present disclosure.

DESCRIPTION OF SYMBOLS

- 10: organic photoelectric device
- 11: the first electrode
- 15: organic layer
- 19: the second electrode
- 31: hole transport layer (HTL)
- 32: emission layer
- 33: hole transport auxiliary layer
- 34: electron transport layer (ETL)
- 35: electron transport auxiliary layer
- 36: electron injection layer (EIL)
- 37: hole injection layer (HIL)

MODE FOR INVENTION

Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to the like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the figures, to explain aspects of the present description. 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 embodiment of the present disclosure, there is provided a condensed cyclic compound represented by Formula 1 below:

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In Formula 1, ring A₁may be represented by Formula 1A:

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In Formula 1A, X₁may be N-[(L₁)_a1-(R₁)_b1], S, O, or Si(R₄)(R₅).

a1 to a3 are each independently an integer selected from 0 to 5,

b1 to b3 are each independently an integer selected from 1 to 3,

wherein R₃is not a substituted or unsubstituted morpholinyl group;

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₆₀alkyl group, and a C₁-C₆₀alkoxy group,

—Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇);

In Formula 1, L₁, a1, R₁, b1, R₄, and R₅will be defined below.

In some embodiments, X₁in Formula 1A may be S, O, or Si(R₄)(R₅), but is not limited thereto. In some other embodiments, X₁may be S or O, but is not limited thereto.

The ring A₁may be fused to adjacent two 6-membered rings with shared carbon atoms. Accordingly, the condensed cyclic compound of Formula 1 above may be represented by one of Formulae 1-1 and 1-2:

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In Formulae 1-1 to 1-2, X₁, L₂, L₃, a2, a3, R₂, R₃, R₁₁to R₁₄, b2 and b3 may be the same as those of Formula 1 defined below.

In Formulae 1, 1-1, and 1-2, L₁to L₃may be each independently selected from a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₂-C₆₀heteroarylene group, and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, wherein L₂and L₃may be not a substituted or unsubstituted carbazolylene group.

For example, L₁to L₃may be each independently selected from

a phenylene group, a biphenylene group, a terphenylene group, a quaterphenylene 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, a 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 phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzoxazolylene group, a benzimidazolylene 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, an imidazopyrimidinylene group, and an imidazopyridinylene group, each substituted with at least one of a deuterium atom, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a C₆-C₂₀aryl group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, and —Si(Q₃₃)(Q₃₄)(Q₃₅), wherein Q₃₃to Q₃₅are each independently a hydrogen, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, benzoquinazolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, and a quinazolinyl group, wherein L₂and L₃are not a substituted or unsubstituted carbazolylene group.

In some embodiments, in above Formulae, L₁to L₃may be each independently represented by one of Formulae 2-1 to 2-15:

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In Formulae 2-1 to 2-15,

Z₁to Z₄may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a naphthyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a benzoquinazolinyl group, a benzoquinoxalinyl group, a biphenyl group, and —Si(Q₃₃)(Q₃₄)(Q₃₅), wherein Q₃₃to Q₃₅may be each independently selected from a hydrogen, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a benzimidazolyl group, a benzothiazolyl group, a benzoxazolyl group, benzoquinolinyl group, a benzoisoquinolinyl group, a benzoquinazolinyl group, a benzoquinoxalinyl group, and a quinoxalinyl group;

d1 may be an integer selected from 1 to 4; d2 may be an integer selected from 1 to 3; d3 may be an integer selected from 1 to 6; d4 may be an integer selected from 1 to 8; d6 may be an integer selected from 1 to 5; and * and *′ may be each independently a binding site with an adjacent atom.

In some other embodiments, in above Formulae, L₁to L₃may be each independently represented by one of Formulae 3-1 to 3-37, but are not limited thereto:

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In Formula 1 above, a1, which indicates the number of L₁s, may be 0, 1, 2, 3, 4, or 5, and in some embodiments, 0, 1, or 2, and in some other embodiments, 0 or 1. When a1 is 0, *-(L₁)_a1-*′ may be a single bond. When a1 is 2 or greater, the at least two L₁s may be identical to or different from each other, a2 and a3 in Formula 1 may be may be understood based on the description of a1 and the structure of Formula 1.

In some embodiments, a1, a2, and a3 may be each independently 0, 1, or 2.

In above Formulae, R₁to R₅may be each independently selected from a hydrogen, a deuterium, a fluoro group (—F), a chloro group (—Cl), a bromo group (—Br), an iodo group (—I), a hydroxyl group, a cyano group, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₂-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇), wherein at least one of R₂and R₃is a substituted or unsubstituted N-containing C₂-C₆₀heteroaryl group.

In some embodiments, in above Formulae, R₁to R₅may be each independently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, 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, —F, —Cl, —Br, —I, a hydroxyl group, and a cyano 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 benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluorantenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a pycenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, a ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, a oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, an isobenzothiazolyl group, a benzooxazolyl group, a benzothiazolyl group, a benzoquinazolinyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, —Si(Q₃₃)(Q₃₄)(Q₃₅), a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluorantenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a pycenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, a ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, a oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, an isobenzothiazolyl group, a benzooxazolyl group, a benzothiazolyl group, a benzoquinazolinyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and a biphenyl group, and

—Si(Q₃)(Q₄)(Q₅),

wherein R₄and R₅may be not —Si(Q₃)(Q₄)(Q₅);

Q₃to Q₅, and Q₃₃to Q₃₅may be each independently selected from a hydrogen, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a benzimidazolyl group, a benzothiazolyl group, a benzoquinazolinyl group, and a quinoxalinyl group; and

at least one of R₂and R₃may be each independently selected from

a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, a oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, an isobenzothiazolyl group, a benzooxazolyl group, a benzothiazolyl group, benzoquinazolinyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, —Si(Q₃₃)(Q₃₄)(Q₃₅), a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluorantenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a pycenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, a ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, a oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, an isobenzothiazolyl group, a benzooxazolyl group, a benzothiazolyl group, a benzoquinazolinyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and a biphenyl group;

In some embodiments, in Formula 1, 1-1, and 1-2, R₁to R₅may be each independently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, 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, —F, —Cl, —Br, —I, a hydroxyl group, and a cyano group,

a phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a triazinyl group, a benzimidazolyl group, a benzothiazolyl group, benzoxazolyl group, benzoquinazolinyl group, benzoquinolinyl group, a benzoisoquinolinyl group, and a benzoquinoxalinyl group;

a phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluorantenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a triazinyl group, a benzimidazolyl group, a benzothiazolyl group, benzoxazolyl group, benzoquinazolinyl group, benzoquinolinyl group, a benzoisoquinolinyl group, and a benzoquinoxalinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, —Si(Q₃₃)(Q₃₄)(Q₃₅), a phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluorantenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a triazinyl group, a benzimidazolyl group, a benzothiazolyl group, benzoxazolyl group, benzoquinazolinyl group, benzoquinolinyl group, a benzoisoquinolinyl group, and a benzoquinoxalinyl group, and

—Si(Q₃)(Q₄)(Q₅),

wherein R₄and R₅may be not —Si(Q₃)(Q₄)(Q₅);

Q₃to Q₅, and Q₃₃to Q₃₅may be each independently selected from a hydrogen, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a benzimidazolyl group, a benzothiazolyl group, benzoxazolyl group, benzoquinolinyl group, a benzoisoquinolinyl group, a benzoquinoxalinyl group, a benzoquinazolinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group; and

at least one of R₂and R₃may be each independently selected from

In some other embodiments, in Formulae 1, 1-1, and 1-2, R₁to R₅may be each independently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, 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, —F, —Cl, —Br, —I, a hydroxyl group, and a cyano group,

a group represented by one of Formulae 4-1 to 4-31, and

—Si(Q₃)(Q₄)(Q₅),

wherein R₄and R₅may be not —Si(Q₃)(Q₄)(Q₅); and

at least one of R₂and R₃may be each independently a group represented by one of Formulae 4-6 to 4-25, 4-30 and 4-31:

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In Formulae 4-1 to 4-33,

Y₃₁may be O, S, C(Z₃₃)(Z₃₄), N(Z₃₅), or Si(Z₃₆)(Z₃₇), where Y₃₁in Formula 4-23 may be not NH,

Y₃₂may be C(Z₃₃)(Z₃₄), or Si(Z₃₆)(Z₃₇),

Z₃₁to Z₃₇may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a benzimidazolyl group, a benzothiazolyl group, a benzoxazolyl group, a benzoquinazolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a benzoquinoxalinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a biphenyl group, and —Si(Q₃₃)(Q₃₄)(Q₃₅), wherein Q₃to Q₅, and Q₃₃to Q₃₅may be each independently selected from a hydrogen, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzimidazolyl group, a benzothiazolyl group, a benzoxazolyl group, a benzoquinazolinyl group, a benzoisoquinolinyl group, a benzoquinoxalinyl group, an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group,

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

In some other embodiments, in Formulae 1, 1-1, and 1-2, R₁may be selected from

a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a fluorenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, and a perylenyl group, and

a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluorantenyl group, a fluorenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, and a perylenyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic 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 C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluorantenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, and a perylenyl group.

In some other embodiments, at least one of R₂and R₃in above Formulae may be selected from

a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a triazinyl group, a benzimidazolyl group, a benzothiazolyl group, a benzoxazolyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, and a benzoquinoxalinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, —Si(Q₃₃)(Q₃₄)(Q₃₅), a phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluorantenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a benzoquinoxalinyl group, a triazinyl group, a benzimidazolyl group, a benzothiazolyl group, a benzoxazolyl group, and a benzoquinazolinyl group.

In above Formulae, R₁₁to R₁₄may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a monovalent non-aromatic condensed polycyclic group, —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇),

For example, R₁₁to R₁₄in above Formulae may be each independently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, 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, —F, —Cl, —Br, —I, a hydroxyl group, and a cyano group,

—Si(Q₃)(Q₄)(Q₅), wherein Q₃to Q₅may be each independently selected from a hydrogen, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, and a chrysenyl group.

In some embodiments, R₁₁to R₁₄in above Formulae may be each independently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₂₀alkyl group, and a C₁-C₂₀alkoxy group,

a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, and a perylenyl group, and

In some other embodiments, in above Formulae, R₁₁to R₁₄may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₂₀alkyl group, and a C₁-C₂₀alkoxy group, but are not limited thereto.

In some other embodiments, R₁₁to R₁₄in above Formulae may be all hydrogens.

In some other embodiments, R₁to R₅in above Formulae may be each independently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, 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, —F, —Cl, —Br, —I, a hydroxyl group, and a cyano group,

a group represented by one of Formulae 5-1 to 5-45, and

—Si(Q₃)(Q₄)(Q₅),

wherein R₄and R₅may be not —Si(Q₃)(Q₄)(Q₅);

at least one of R₂and R₃are each independently selected from a group represented by one of Formulae 5-10 to 5-17, and 5-22 to 5-45; and

R₁₁to R₁₄may be each independently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₂₀alkyl group, and a C₁-C₂₀alkoxy group,

a group represented by one of Formulae 5-1 to 5-9, and 5-18 to 5-21, and

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In Formula 1 above, R₃may be not a substituted or unsubstituted morpholinyl group.

When R₃in Formula 1 is selected from a pyridinyl group, pyridazinyl group, or a pyrimidinyl group, R₂may be a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted carbazolyl group, and a substituted or unsubstituted triphenylenyl group.

In Formula 1 above, b1, which indicates the number of R₁s, may be an integer of 1 to 3, and in some embodiments, may be 1 or 2. For example, b1 may be 1. When b1 is 2 or greater, the at least two R₁may be identical to or different from each other. b2 and b3 in Formula 1 may be may be understood based on the description of b1 and the structure of Formula 1.

In some embodiments, in any of the formulae herein, at least one of substituents of the substituted C₃-C₁₀cycloalkylene group, the substituted C₂-C₁₀heterocycloalkylene group, the substituted C₃-C₁₀cycloalkenylene group, the substituted C₂-C₁₀heterocycloalkenylene group, the substituted C₆-C₆₀arylene group, the substituted C₂-C₆₀heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀alkoxy group, the substituted C₃-C₁₀cycloalkyl group, the substituted C₂-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₂-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀aryl group, the substituted C₆-C₆₀aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₂-C₆₀heteroaryl group, and the substituted monovalent non-aromatic condensed polycyclic group may be selected from

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₆₀alkyl group, and a C₁-C₆₀alkoxy group,

a C₁-C₆₀alkyl group, and a C₁-C₆₀alkoxy group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, —Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇),

a C₃-C₁₀cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₆₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₂-C₆₀heteroaryl group, and a monovalent non-aromatic condensed polycyclic group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, —Si(Q₂₃)(Q₂₄)(Q₂₅), and —B(Q₂₆)(Q₂₇), and

—Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇);

Q₃to Q₇, Q₁₃to Q₁₇, Q₂₃to Q₂₇, and Q₃₃to Q₃₇may be each independently selected from a hydrogen, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₂-C₆₀heteroaryl group, and a monovalent non-aromatic condensed polycyclic group; and

a substituent of R₂and R₃are not a carbazolyl group substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₆₀alkyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₂-C₁₀heterocycloalkyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, —Si(Q₂₃)(Q₂₄)(Q₂₅), and —B(Q₂₆)(Q₂₇).

In some other embodiments, in any of the formulae herein, at least one of substituents of the substituted C₃-C₁₀cycloalkylene group, the substituted C₂-C₁₀heterocycloalkylene group, the substituted C₃-C₁₀cycloalkenylene group, the substituted C₂-C₁₀heterocycloalkenylene group, the substituted C₆-C₆₀arylene group, the substituted C₂-C₆₀heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀alkoxy group, the substituted C₃-C₁₀cycloalkyl group, the substituted C₂-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₂-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀aryl group, the substituted C₆-C₆₀aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₂-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, and a C₁-C₆₀alkoxy group,

a C₁-C₆₀alkyl group, and a C₁-C₆₀alkoxy group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano 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 dibenzofluorenyl group, a dibenzofluorenyl group, a phenaleny group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a 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 benzoisoquinolinyl group, a benzoquinazolinyl group, a benzoquinoxalinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇),

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 dibenzofluorenyl group, a dibenzofluorenyl group, a phenaleny group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a benzoquinazolinyl group, a benzoquinoxalinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy 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 dibenzofluorenyl group, a dibenzofluorenyl group, a phenaleny group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —Si(Q₂₃)(Q₂₄)(Q₂₅), and —B(Q₂₆)(Q₂₇), and

—Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇);

Q₁₃to Q₁₇, Q₂₃to Q₂₇, and Q₃₃to Q₃₇may be each independently selected from a hydrogen, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy 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 dibenzofluorenyl group, a dibenzofluorenyl group, a phenaleny group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a benzoisoquinolinyl group, benzoquinazolinyl group, a benzoquinoxalinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; and

a substituent of R₂and R₃are not carbazolyl group substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₆₀alkyl group, a C₁-C₆₀alkoxy 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 dibenzofluorenyl group, a dibenzofluorenyl group, a phenaleny group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a benzoquinazolinyl group, a benzoquinoxalinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —Si(Q₂₃)(Q₂₄)(Q₂₅), and —B(Q₂₆)(Q₂₇).

In some embodiments, the condensed cyclic compound of Formula 1 above may be one of Compounds of Group I below, but is not limited thereto:

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In Formula 1 above, at least one of R₂and R₃may be selected from a substituted or unsubstituted N-containing C₂-C₆₀heteroaryl group. Thus, the condensed cyclic compound of Formula 1 above may have a highest occupied molecular orbital (HOMO) energy level, a lowest unoccupied molecular orbital (LUMO) energy level, a T1 energy level, and an S1 energy level that are appropriate for a material for an organic light emitting device, for example, a host material for the EML (for example, a host material for the EML including both a host and a dopant). The condensed cyclic compound of Formula 1 may have good thermal and electrical stabilities, and accordingly, an organic light-emitting device using the condensed cyclic compound of Formula 1 may have high efficiency and long lifetime characteristics.

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The condensed cyclic compound of Formula 1 above has a core in which a pyrimidine ring and a benzene ring are condensed to opposite sides of the ring A₁, respectively (refer to Formula 1′ above), and accordingly may have a HOMO energy level, a LUMO energy level, a T1 energy level, and an S1 energy level that are appropriate for use as a material for an organic layer (for example, a material for the EML) disposed between a pair of electrodes of an organic light-emitting device, and have good thermal and electrical stabilities. For example, when the condensed cyclic compound of Formula 1 above is used as a host in the EML of an organic light-emitting device, the organic light-emitting device may have high efficiency and long lifetime, based on the host-dopant energy transfer mechanism.

Although not limited to any specific theory, Compound B below may have too strong electron transport ability to achieve an equilibrium between hole transport and electron transport. Accordingly, an organic light-emitting device including Compound B may have poor efficiency characteristics. Compound C below includes a condensed cyclic core in a pyrazine ring, instead of a pyrimidine ring, and thus may have poor thermal and electrical stabilities.

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A synthesis method of the condensed cyclic compound of Formula 1 above may be easily understood to one of ordinary skill in the art based on the synthesis examples described below.

As described above, the condensed cyclic compound of Formula 1 above may be appropriate for use as a host of the EML or a electron transport auxiliary layer of the organic layer (a host of the EML).

Due to the inclusion of the organic layer including the condensed cyclic compound of Formula 1 described above, the organic light-emitting device may have a low driving voltage, a high efficiency, and a long lifetime.

The condensed cyclic compound of Formula 1 above may be used between a pair of electrodes of an organic light-emitting device. For example, the condensed cyclic compound of Formula 1 above may be included in at least one of the EML, a hole transport region between the first electrode and the EML (for example, the hole transport region may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL)), and an electron transport region between the EML and the second electrode (for example, the electron transport region may include at least one of a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL). For example, the condensed cyclic compound of Formula 1 above may be included in the EML, wherein the EML may further include a dopant, and the condensed cyclic compound of Formula 1 in the EML may serve as a host. For example, the EML may be a green EML, and the dopant may be a phosphorescent dopant.

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

For example, the organic layer of the organc light-emitting device may include only Compound 1 as the condensed cyclic compound. For example, Compound 1 may be included in the EML of the organic light-emitting device. In some embodiments, the organic layer of the organic light-emitting device may include Compounds 1 and 2 as the condensed cyclic compound. For example, Compounds 1 and 2 may be included in the same layer (for example, in the EML) or in different layers. For example, the condensed cyclic compound may be included as a host in an emission of an organic layer, or in an electron transport auxiliary layer.

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 comprising 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, for example, an organic compound or an organometallic complex including a metal.

According to another embodiment of the present disclosure, 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 wherein the organic layer includes the condensed cyclic compounds of Formula 1 above.

FIGS. 1 to 3 are schematic views of an organic light-emitting device 10 according to an embodiment of the present disclosure. Hereinafter, a structure of an organic light-emitting device according to an embodiment of the present disclosure 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, a first electrode 11, an organic layer 15, and a second electrode 19 are sequentially stacked in this order.

A substrate (not shown) may be disposed under the first electrode 11 or on the second electrode 190 in FIG. 1. The substrate may be any substrate that is used in conventional organic light emitting devices. In some embodiments the substrate 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 11 may be formed by depositing or sputtering a first electrode-forming material on the substrate. The first electrode 11 may be an anode. A material having a high work function may be selected as a material for the first electrode to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. For example, the material for the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), or zinc oxide (ZnO). In some embodiments, the material for the first electrode 11 may be metals, for example, magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or the like.

The first electrode 11 may have a single-layer structure or a multi-layer structure including at least two layers.

The organic layer 15 may be disposed on the first electrode 11.

The organic layer 15 may include at least one a hole transport region; an EML, and an electron transport region. For example, referring to FIG. 2, an organic light-emitting device according to one embodiment is described as follows.

An organic layer 15 includes a hole transport layer 31, an emission layer 32, and a hole transport auxiliary layer 33 interposed between the hole transport layer 31 and the emission layer 32.

The hole transport region may include at least two hole transport layers, and a hole transport layer contacting the emission layer is defined to be a hole transport auxiliary layer.

The hole transport region may be disposed between the first electrode 11 and the EML.

The hole transport region may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), and a buffer layer.

The hole transport region may include exclusively the HIL or the HTL. In some embodiments, the electron transport region may have a structure including a HIL 37/HTL 31 or a HIL 37/HTL 31/EBL, wherein the layers forming the structure of the electron transport region may be sequentially stacked on the first electrode 10 in the stated order.

For example, a hole injection layer 37 and an electron injection layer 36 are additionally included and thus a first electrode 11/hole injection layer 37/hole transport layer 31/hole transport auxiliary layer 33/emission layer 32/electron transport auxiliary layer 35/electron transport layer 34/electron injection layer 36/a second electrode 19 are sequentially stacked, as shown in FIG. 3.

The hole injection layer 37 may improve interface properties between ITO as an anode and an organic material used for the hole transport layer 31, and is applied on a non-planarized ITO and thus planarizes the surface of the ITO. For example, the hole injection layer 37 may include a material having a median value, particularly desirable conductivity between a work function of ITO and HOMO of the hole transport layer 31, in order to adjust a difference a work function of ITO as an anode and HOMO of the hole transport layer 31. In connection with the present disclosure, the hole injection layer 37 may include N4,N4′-diphenyl-N4,N4′-bis(9-phenyl-9H-carbazol-3-yl)biphenyl-4,4′-diamine), but is not limited thereto. In addition, the hole injection layer 37 may further include a conventional material, for example, copper phthlalocyanine (CuPc), aromatic amines such as N,N′-dinaphthyl-N,N′-phenyl-(1,1′-biphenyl)-4,4′-diamine, NPD), 4,4′,4″-tris[methylphenyl(phenyl)amino]triphenyl amine (m-MTDATA), 4,4′,4″-tris[1-naphthyl(phenyl)amino]triphenyl amine (1-TNATA), 4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenyl amine (2-TNATA), 1,3,5-tris[N-(4-diphenylaminophenyl)phenylamino]benzene(p-DPA-TDAB), and the like, compounds such as 4,4′-bis[N-[4-{N,N-bis(3-methylphenyl)amino}phenyl]-N-phenylamino]biphenyl (DNTPD), hexaazatriphenylene-hexacarbonitirile (HAT-CN), and the like, a polythiophene derivative such as poly(3,4-ethylenedioxythiophene)-poly(styrnesulfonate) (PEDOT) as a conductive polymer. The hole injection layer 37 may be, for example coated on ITO as an anode in a thickness of 10 to 300 Å.

The electron injection layer 36 is stacked on the electron transport layer to facilitate electron injection into a cathodeand improves power efficiency. The electron injection layer 36 may include any generally-used material in this art without limitation, for example, LiF, Liq, NaCl, CsF, Li₂O, BaO, and the like.

When the hole transport region includes the HIL, the HIL may be formed on the first electrode 11 by any of a variety of methods, for example, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, or the like.

When the HIL is formed using vacuum deposition, vacuum deposition conditions may vary depending on the material 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□ to about 500□, 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 depending on the material 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 a range of about 80□ to about 200□. However, the coating conditions are not limited thereto.

Conditions for forming the HTL and the EBL may be defined based on the above-described formation conditions for the HIL.

In some embodiments, the hole transport region may include at least one of m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzene sulfonic acid (Pani/DBSA), poly(3, 4-ethylenedioxythiophene)/poly(4-styrenesulfonate)(PEDOT/PSS), polyaniline/camphor sulfonic acid (Pani/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201 below, and a compound represented by Formula 202 below.

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In Formula 201 above, 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, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid 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 C₂-C₁₀heterocycloalkyl group, a C₂-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

In Formula 201, 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 201 and 202, R₁₀₁to R₁₀₈, R₁₁₁to R₁₁₉, and R₁₂₁to R₁₂₄may be each independently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, or the like), and a C₁-C₁₀alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, or the like);

a C₁-C₁₀alkyl group and a C₁-C₁₀alkoxy group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;

a phenyl group, a naphthyl group, an anthracenyl 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, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group, and a C₁-C₁₀alkoxy group. However, embodiments of the present disclosure are not limited thereto.

In Formula 201 above, R₁₀₉may be selected from

a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group, and

a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, and a C₁-C₂₀alkoxy group.

In some embodiments, the compound of Formula 201 may be represented by Formula 201A, but is not limited thereto:

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In Formula 201A, R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉may be the same as those defined above.

For example, the compound of Formula 201 and the compound of Formula 202 may include Compounds HT1 to HT20 below, but are not limited thereto:

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A thickness of the hole transport region may be from about 100 Å to about 10000 Å, and in some embodiments, from about 100 Å to about 1000 Å. When the hole transport region includes a HIL and a HTL, a thickness of the HIL may be from about 100 Å to about 10,000 Å, and in some embodiments, from about 100 Å to about 1,000 Å, and a thickness of the HTL may be from about 50 Å to about 2,000 Å, and in some embodiments, from about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the HIL, and the HTL are within these ranges, satisfactory hole transport characteristics may be obtained without a substantial increase in driving voltage.

The hole transport region may further include a charge-generating material to improve conductivity, in addition to the materials as described above. The charge-generating material may be homogeneously or inhomogeneously dispersed in the hole transport region.

The charge-generating material may be, for example, a p-dopant. The p-dopant may be one of a quinine derivative, a metal oxide, and a cyano group-containing compound, but is 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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The hole transport region may further include a buffer layer.

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 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 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 depending on the material that is used to form the EML.

The EML may include a host and a dopant. The host may include at least one of the condensed cyclic compounds of Formula 1 above. For example, the first host and the second host differ from each other.

In some embodiments, the organic layer of the organic light-emitting device may include only the above condensed compound (the first host), or further include at least one of a first compound represented by Formula 41 below and a second compound represented by Formula 61 below, in addition to the condensed cyclic compound of Formula 1 above.

The second host may include at least one of the first compound represented by Formula 41 and the second compound represented by Formula 61. The ring A₆₁is represented by the following Formula 61A, and the ring A₆₂is represented by the following Formula 61B.

In Formula 61 below, the ring A₆₁is fused to an adjacent 5-membered ring and the ring A₆₂with sharing carbons therewith, and the ring A₆₂is fused to the adjacent ring A₆₁and a 6-membered ring with sharing carbons therewith:

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In Formulae 41 and 61 above,

X₄₁may be N-[(L₄₂)_a42-(R₄₂)_b42], S, O, S(═O), S(═O)₂, a C(═O), a C(R₄₃)(R₄₄), Si(R₄₃)(R₄₄), P(R₄₃), P(═O)(R₄₃), or C═N(R₄₃);

Ring A₆₁in Formula 61 may be represented by Formula 61A above;

Ring A₆₂in Formula 61 may be represented by Formula 61B above;

X₆₁may be N-[(L₆₂)_a62-(R₆₂)_b62], S, O, S(═O), S(═O)₂, a C(═O), a C(R₆₃)(R₆₄), Si(R₆₃)(R₆₄), P(R₆₃), P(═O)(R₆₃), or C═N(R₆₃);

X₇₁may be C(R₇₁) or N; X₇₂may be C(R₇₂) or N; X₇₃may be C(R₇₃) or N; X₇₄may be C(R₇₄) or N; X₇₅may be C(R₇₅) or N; X₇₆may be C(R₇₆) or N; X₇₇may be C(R₇₇) or N; X₇₈may be C(R₇₈) or N;

Ar₄₁, L₄₁, L₄₂, L₆₁, and L₆₂may be each independently selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₂-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₂-C₆₀heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group;

n1 and n2 may be each independently an integer selected from 0 to 3;

R₄₁to R₄₄, R₅₁to R₅₄, R₆₁to R₆₄, and R₇₁to R₇₉may be each independently selected from a hydrogen, a deuterium a fluoro group (—F), a chloro group (—Cl), a bromo group (—Br), an iodo group (—I), a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, 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-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₂-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇);

a41, a42, a61, and a62 may be each independently an integer selected from 0 to 5; and

b41, b42, b51 to b54, b61, b62, and b79 may be each independently an integer selected from 1 to 3.

In some embodiments, X₄₁in Formula 41 may be N-[(L₄₂)_a42-(R₄₂)_b42], S, or O, but is not limited thereto.

In some embodiments, X₆₁in Formula 61 may be N-[(L₆₂)_a62-(R₆₂)_b62], S, or O, but is not limited thereto.

In some other embodiments, in Formula 61, X₇₁may be C(R₇₁), X₇₂may be C(R₇₂), X₇₃may be C(R₇₃), X₇₄may be C(R₇₄), X₇₅may be C(R₇₅), X₇₆may be C(R₇₆), X₇₇may be C(R₇₇), and X₇₈may be C(R₇₈). However, embodiments of the present disclosure are not limited thereto.

In Formula 61 above, at least two of R₇₁to R₇₄may be optionally linked to each other to form a saturated or unsaturated ring, for example, benzene, naphthalene, or the like.

In Formula 61 above, at least two of R₇₅to R₇₈may be optionally linked to each other to form a saturated or unsaturated ring, for example, benzene, naphthalene, or the like.

In Formulae 41 and 61 above, Ar₄₁, L₄₁, L₄₂, L₆₁, and L₆₂may be each independently selected from

a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₂-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₂-C₆₀heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.

In Formulae 41 and 61 above, Ar₄₁, L₄₁, L₄₂, L₆₁, and L₆₂may 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, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene group, each substituted with at least one of a deuterium atom, —F, —Cl, —Br, —I, 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 C₁-C₂₀alkoxy group, a C₆-C₂₀aryl group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heterocyclic group, and —Si(Q₃₃)(Q₃₄)(Q₃₅), wherein Q₃₃to Q₃₅may be each independently a hydrogen, a C₁-C₂₀alkyl 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 pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, or a quinazolinyl group.

In some other embodiments, in Formula 41 and 61, Ar₄₁, L₄₁, L₄₂, L₆₁, and L₆₂may be each independently selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₃-C₆₀cycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group.

In some other embodiments, in Formulae 41 and 61, R₄₁to R₄₄, R₅₁to R₅₄, R₆₁to R₆₄, and R₇₁to R₇₉may be each independently selected from

a hydrogen atom, a deuterium atom, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxylic acid 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 phenyl group, a pentalenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a pentalenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluorantenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group.

In some other embodiments, R₅₁, R₅₃, and R₅₄in Formula 41, and R₇₁to R₇₉in Formula 61 may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, and a C₁-C₂₀alkoxy group.

In some other embodiments, R₅₁, R₅₃, and R₅₄in Formula 41, and R₇₁to R₇₉in Formula 61 may be all hydrogens.

In some other embodiments, R₄₁, R₄₂, and R₅₂in Formula 41, and R₆₁and R₆₂in Formula 61 may be each independently a group represented by one of Formulae 4-1 to 4-31 regarding Formula 1 above. For example, R₄₁, R₄₂, and R₅₂in Formula 41, and R₆₁and R₆₂in Formula 61 may be each independently a group represented by one of Formulae 4-1 to 4-8, and Formulae 4-26 to 4-29, 4-32 and 4-33 regarding Formula 1 above. In some other embodiments, R₄₁, R₄₂, and R₅₂in Formula 41, and R₆₁and R₆₂in Formula 61 may be each independently a group represented by one of Formulae 5-1 to 5-12, 5-17, 5-22 and 5-46 to 5-57 regarding Formula 1 above. However, embodiments of the present disclosure are not limited thereto.

In some other embodiments, the emission layer of the organic light-emitting device may include a first host, a second host, and a dopant, wherein the first host and the second host differ from each other,

the first host may include the at least one of the condensed cyclic compounds of Formula 1 above, and

the second host may include at least one of a first compound represented by Formula 41 and a second compound represented by Formula 61.

In some other embodiments, the first compound of Formula 41 above may be represented by one of Formulae 41-1 to 41-12 below, and the second compound of Formula 61 above may be represented by one of Formulae 61-1 to 61-6 below.

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In Formulae 41-1 to 41-12, and Formulae 61-1 to 61-6, X₄₁, X₆₁, L₄₁, a41, L₆₁, a61, R₄₁, b41, R₅₁to R₅₄, b51 to b54, R₆₁, b61, R₇₁to R₇₉and b79 may be the same as those defined above.

In another embodiment, the condensed cyclic compound represented by Formula 1 includes one of the compounds 2, 34, 66, 98, 130, 162, 194, 226, a-1 to a-68, b-1 to b-68, c-1 to c-68, d-1 to d-68, e-1 to e-68, f-1 to f-68, g-1 to g-68, and h-1 to h-68;

in some embodiments, the first compound of Formula 41 above may include one of Compounds A1 to A111 below, and the second compound of Formula 61 may include one of Compounds B1 to B20 below. However, embodiments of the present disclosure are not limited thereto.

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For example, the condensed cyclic compound represented by Formula 1 may include one of the compounds of Group I, and the first compound of Formula 41 above and the second compound of Formula 61 may include one of the compounds of Group 2.

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For example, a weight ratio of the first host to the second host may be in a range of about 1:99 to about 99:1, and in some embodiments, about 10:90 to about 90:10. When the weight ratio of the first host to the second host is within these ranges, the electron transport characteristics of the first host and the hole transport characteristics of the second host may reach equilibrium, so that the emission efficiency and lifetime of the organic light-emitting device may be improved.

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.

Synthesis methods of the condensed cyclic compound of Formula 1 above, the first compound of Formula 41 above, and the second compound of Formula 61 above may be easily understood to one of ordinary skill in the art based on the synthesis examples described below.

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. A host of one of the red emission layer, the green emission layer, and the blue emission layer may include the condensed cyclic compound of Formula 1 above. For example, the host of the green emission layer may include the condensed cyclic compound of Formula 1, or the electron transport auxiliary layer on the blue emission layer may include the condensed cyclic compound of Formula 1.

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.

In some embodiments, the EML may include a host including at least one of the condensed cyclic compound of Formula 1, and a phosphorescent dopant. The phosphorescent dopant may include an organometallic complex including a transition metal, for example, iridium (Ir), platinum (Pt), osmium (Os), or rhodium (Rh).

The phosphorescent dopant may include an organometallic compound represented by Formula 81 below:

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In Formula 81,

M may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm);

Y₁to Y₄may be each independently a carbon (C) or a nitrogen (N);

Y₁and Y₂may be linked to each other via a single bond or a double bond, and Y₃and Y₄may be linked to each other via a single bond or a double bond;

CY₁and CY₂may be each independently benzene, naphthalene, fluorene, spiro-fluorene, indene, pyrrole, thiophene, furan, imidazole, pyrazole, thiazole, isothiazole, oxazole, isooxazole, pyridine, pyrazine, pyrimidine, pyridazine, quinoline, isoquinoline, benzoquinoline, quinoxaline, quinazoline, carbazole, benzoimidazole, benzofuran(benzofuran), benzothiophene, isobenzothiophene, benzooxazole, isobenzooxazole, triazole, tetrazole, oxadiazole, triazine, dibenzofuran, or dibenzothiophene, wherein CY₁and CY₂may be optionally linked to each other via a single bond or an organic linking group;

R₈₁and R₈₂may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, —SF₅, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₂-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), and —B(Q₆)(Q₇);

a81 and a82 may be each independently an integer selected from 1 to 5;

n81 may be an integer selected from 0 to 4;

n82 may be 1, 2, or 3;

L₈₁may be selected from a monovalent organic ligand, a divalent organic ligand, and a trivalent organic ligand.

R₈₁and R₈₂in Formula 81 may be defined to be the same as described above with reference to R₁₁above.

The phosphorescent dopant may include at least one of Compounds PD1 to PD78, but is not limited thereto (the following Compound PD1 is Ir(ppy)₃.):

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In some embodiments, the phosphorescent dopant may include PtOEP or PhGD represented below:

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In some other embodiments, the phosphorescent dopant may include at least one of DPVBi, DPAVBi, TBPe, DCM, DCJTB, Coumarin 6, and C545T represented below.

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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 20 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 improved light emitting ability without a substantial increase in driving voltage.

Next, the electron transport region may be disposed on the EML.

The electron transport region may include at least one of a HBL, an ETL, and an EIL.

In some embodiments, the electron transport region may have a structure including a HBL/ETL/EIL, or an ETL/EIL, wherein the layers forming the structure of the electron transport region may be sequentially stacked on the EML in the stated order. However, embodiments of the present disclosure are not limited thereto. For example, an organic light-emitting device according to one embodiment may include at least two hole transport layers in the hole transport region, and in this case, a hole transport layer contacting the emission layer is defined to be a hole transport auxiliary layer 35.

The ETL may have a single-layer structure or a multi-layer structure including at least two different materials.

The electron transport region may include a condensed cyclic compound represented by Formula 1 above. For example, the electron transport region may include an ETL, and the ETL may include the condensed cyclic compound of Formula 1 above. More specifically, the electron transport auxiliary layer may include the condensed cyclic compound represented by the Formula 1.

Conditions for forming the HBL, ETL, and EIL of the electron transport region may be defined based on the above-described formation conditions for the HIL.

When the electron transport region includes the HBL, the HBL may include at least one of BCP below, Bphen below, and BAlq below. However, embodiments of the present disclosure are not limited thereto.

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The thickness of the HBL may be from about 20 Å to about 1000 Å, and in some embodiments, 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.

The ETL may further include at least one of Alq₃, Balq, TAZ, and NTAZ below, in addition to BCP and Bphen described above.

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In some embodiments, the ETL may include at least one of Compounds ET1 and ET2 represented below, but is not limited thereto.

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A thickness of the ETL may be from about 100 Å to about 1000 Å, and in some embodiments, 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-described materials.

The metal-containing material may include a lithium (Li) complex. Non-limiting examples of the Li complex are compound ET-D1 below (lithium quinolate (LiQ)), or compound ET-D2 below.

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The electron transport region may include an EIL that may facilitate injection of electrons from the second electrode 19. The EIL may include at least one selected from LiF, NaCl, CsF, Li₂O, and BaO. The thickness of the EIL may be from about 1 Å to about 100 Å, and in some embodiments, 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 19 is disposed on the organic layer 15. The second electrode 19 may be a cathode. A material for the second electrode 19 may be a metal, an alloy, or an electrically conductive compound that have a low work function, or a combination thereof. Non-limiting examples of the material for the second electrode 19 are lithium (Li), magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), magnesium (Mg)-indium (In), and magnesium (Mg)-silver (Ag), or the like. In some embodiments, to manufacture a top-emission light-emitting device, the second electrode 19 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 of the present disclosure are not limited thereto.

As used herein, a C₁-C₆₀alkyl group refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms. Non-limiting examples of the C₁-C₆₀alkyl group a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-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.

As used herein, a C₁-C₆₀alkoxy group refers to a monovalent group represented by —OA₁₀₁(where A₁₀₁is a C₁-C₆₀alkyl group as described above. 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 structure including at least one carbon double bond in the middle or terminal of the C₂-C₆₀alkyl group. Non-limiting examples of the C₂-C₆₀alkenyl group are an ethenyl group, a prophenyl group, and a butenyl group. A C₂-C₆₀alkenylene group refers to a divalent group having the same structure as the C₂-C₆₀alkenyl group.

As used herein, a C₂-C₆₀alkynyl group refers to a structure including at least one carbon triple bond in the middle or terminal of the C₂-C₆₀alkyl group. Non-limiting examples of the C₂-C₆₀alkynyl group are an ethynyl group and a propynyl group. A C₂-C₆₀alkynylene group used herein refers to a divalent group having the same structure as the C₂-C₆₀alkynyl group.

As used herein, a C₃-C₁₀cycloalkyl group refers to a monovalent, monocyclic hydrocarbon group having 3 to 10 carbon atoms. Non-limiting examples of the C₃-C₁₀cycloalkyl group are a cyclopropyl group, a cyclobutyl group, 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 C₂-C₁₀heterocycloalkyl group refers to a monovalent monocyclic group having 2 to 10 carbon atoms in which at least one hetero atom selected from N, O, P, and S is included as a ring-forming atom. Non-limiting examples of the C₂-C₁₀heterocycloalkyl group are a tetrahydrofuranyl group and a tetrahydrothiophenyl group. A C₂-C₁₀heterocycloalkylene group refers to a divalent group having the same structure as the C₂-C₁₀heterocycloalkyl group.

As used herein, a C₃-C₁₀cycloalkenyl group refers to a monovalent monocyclic group having 3 to 10 carbon atoms that includes at least one double bond in the ring but does not have aromacity. 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 C₂-C₁₀heterocycloalkenyl group used herein refers to a monovalent monocyclic group having 2 to 10 carbon atoms that includes at least one double bond in the ring and in which at least one hetero atom selected from N, O, P, and S is included as a ring-forming atom. Non-limiting examples of the C₂-C₁₀heterocycloalkenyl group are a 2,3-hydrofuranyl group and a 2,3-hydrothiophenyl group. A C₂-C₁₀heterocycloalkenylene group used herein refers to a divalent group having the same structure as the C₂-C₁₀heterocycloalkenyl group.

As used herein, a C₆-C₆₀aryl group refers to a monovalent, aromatic carbocyclic aromatic group having 6 to 60 carbon atoms, and a C₆-C₆₀arylene group refers to a divalent, aromatic carbocyclic group having 6 to 60 carbon atoms. Non-limiting examples of the C₆-C₆₀aryl group are a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C₆-C₆₀aryl group and the C₆-C₆₀arylene group include at least two rings, the rings may be fused to each other.

As used herein, a C₂-C₆₀heteroaryl group refers to a monovalent, aromatic carbocyclic aromatic group having 2 to 60 carbon atoms in which at least one hetero atom selected from N, O, P, and S is included as a ring-forming atom, and 2 to 60 carbon atoms. A C₂-C₆₀heteroarylene group refers to a divalent, aromatic carbocyclic group having 2 to 60 carbon atoms in which at least one hetero atom selected from N, O, P, and S is included as a ring-forming atom. Specifically, non-limiting examples of the N-containing-C₂-C₆₀heteroaryl group are a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, a benzothiazolyl group, a benzoxazole group, a benzoquinolinyl group, a benzoisoquinolinyl group, a benzoquinoxalinyl group, and a benzoquinazolinyl group. When the C₂-C₆₀heteroaryl and the C₂-C₆₀heteroarylene include at least two rings, the rings may be fused to each other.

As used herein, a C₆-C₆₀aryloxy group indicates —OA₁₀₂(where A₁₀₂is a C₆-C₆₀aryl group as described above), and a C₆-C₆₀arylthio group indicates —SA₁₀₃(where A₁₀₃is a C₆-C₆₀aryl group as described above).

As used herein, a monovalent non-aromatic condensed polycyclic group refers to a monovalent group having at least two rings condensed to each other, in which only carbon atoms (for example, 8 to 60 carbon atoms) are exclusively included as ring-forming atoms and the entire molecule has non-aromacity. A non-limiting example of the monovalent non-aromatic condensed polycyclic group is a fluorenyl group. A divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

As used herein, a monovalent non-aromatic condensed heteropolycyclic group refers to a monovalent group having at least two rings condensed to each other, in which carbon atoms (for example, 1 to 60 carbon atoms) and a hetero atom selected from N, O, P, and S are as ring-forming atoms and the entire molecule has non-aromacity. A non-limiting example of the monovalent non-aromatic condensed heteropolycyclic group is a carbazolyl group. A divalent non-aromatic condensed heteropolycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

The acronym “Ph” used herein refers to phenyl, the acronym “Me” used herein refers to methyl, the acronym “Et” used herein refers to ethyl, and the acronym “ter-Bu” or “But” used herein refers to tert-butyl.

One or more embodiments of the present disclosure, which include condensed cyclic compounds, and organic light-emitting devices including the same, will now be described in detail with reference to the following examples. However, these examples are only for illustrative purposes and are not intended to limit the scope of the one or more embodiments of the present disclosure. In the following synthesis example, the expression that “‘B’ instead of ‘A’ was used” means that the amounts of ‘B’ and ‘A’ were the same in equivalent amounts.

Hereinafter, a starting material and a reaction material used in Examples and Synthesis Examples were purchased from Sigma-Aldrich Co. Ltd. or TCI Inc. unless there was particularly mentioned.

(Synthesis of Boronic Ester)

Boronic ester of the following Synthesis Example was synthesized according to the same method as a synthesis method described on page 35 of KR10-2014-0135524A.

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[Synthesis of Intermediate]

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Benzo-methyl-3-aminofuran-2-carboxylate

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Examples
Synthesis of First Host Compound

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Synthesis of Intermediate A(1)(benzo-methyl 3-ureidofuran-2-carboxylate)

33.4 mL (0.38 mol) of chlorosulfonyl isocyanate was dropwise added to a solution of 49.0 g (0.25 mol) of benzo-methyl 3-aminofuran-2-carboxylate in 2000 mL of dichloromethane in a 1000-mL round-bottom flask at about −78° C. The reaction product was heated slowly to room temperature, and stirred for about 2 hours. After the reaction product was concentrated, and 100 mL of Conc. HCl was added thereto, and then stirred at about 100° C. for about 1 hour. The reaction product was cooled down to room temperature, followed by neutralization with an aqueous saturated NaHCO₃solution to precipitate a solid. The resulting solid was filtered to obtain Intermediate A(1) (benzo-methyl 3-ureidofuran-2-carboxylate) in beige solid form (52.1 g, Yield: 87%).

calcd. C₁₁H₁₀N₂O₄: C, 56.41; H, 4.30; N, 11.96; O, 27.33. found: C, 56.45; H, 4.28; N, 11.94; O, 27.32.

Synthesis of Intermediate A(2) (benzo furo[3,2-d]pyrimidine-2,4-diol)

50.0 g (0.21 mol) of Intermediate A(1) (benzo-methyl 3-ureidofuran-2-carboxylate) was suspended in 1000 mL of methanol in a 2000-mL round-bottom flask, and then 300 mL of a 2M NaOH was dropwise added thereto. The reaction mixture was stirred under reflux for about 3 hours. The reaction mixture was cooled down to room temperature, followed by acidification with Conc. HCl to pH 3. After the reaction mixture was concentrated, methanol was slowly dropwise added to precipitate a solid. The resulting solid was filtered and dried to obtain Intermediate A(2) (benzo furo[3,2-d]pyrimidine-2,4-diol) (38.0 g, Yield: 88%).

calcd. C₁₀H₆N₂O₃: C, 59.41; H, 2.99; N, 13.86; O, 23.74. found: C, 59.41; H, 2.96; N, 13.81; O, 23.75.

Synthesis of Intermediate A (benzo-2,4-dichlorofuro[3,2-d]pyrimidine)

37.2 g (0.18 mol) of Intermediate A(2) (benzo-furo[3,2-d]pyrimidine-2,4-diol) was dissolved in 500 mL of phosphorous oxychloride in a 1000-mL round-bottom flask. The resulting mixture was cooled down to about −30° C., and 52 mL (0.36 mol) of N,N-diisopropylethylamine was slowly added thereto. The reaction product was stirred under reflux for about 36 hours, cooled down to room temperature, and then poured into ice/water, followed by extraction with ethyl acetate. An organic layer was collected, washed with an aqueous saturated NaHCO₃solution, dried using Na₂SO₄, and then concentrated to obtain Intermediate B (benzo-2,4-dichlorofuro[3,2-d]pyrimidine) (20.4 g, Yield: 46%). Intermediate A was identified using elemental analysis and nuclear magnetic resonance (NMR). The results are as follows.

calcd. C₁₀H₄Cl₂N₂O: C, 50.24; H, 1.69; Cl, 29.66; N, 11.72; O, 6.69. found: C, 50.18; H, 1.79; Cl, 29.69; N, 11.69; O, 6.70.

300 MHz (CDCl₃, ppm): 7.55 (t, 1H), 7.71-7.82 (m, 2H), 8.25 (d, 1H)

Synthesis of Intermediate A-2-1

70.0 g (292.8 mmol) of Intermediate A, 35.7 g (292.8 mmol) of phenylboronic acid, 101.2 g (732.0 mmol) of potassium carbonate, and 16.0 g (14.6 mmol) of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh₃)₄) were added to 800 mL of 1,4-dioxane and 400 mL of water in a 2000-mL flask, and heated in a nitrogen atmosphere at about 50° C. for about 16 hours. The resulting mixture was added to 3000 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using Silicagel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain Intermediate A-2-1 (31.0 g, Yield: 66%).

calcd. C₁₆H₉ClN₂O: C, 68.46; H, 3.23; Cl, 12.63; N, 9.98; O, 5.70. found: C, 68.95; H, 3.08; Cl, 12.17; N, 10.01; O, 5.62.

Synthesis of Intermediate A-2-2

60.0 g (213.7 mmol) of the intermediate A-2-1, 33.4 g (213.7 mmol) of 3-chlorophenyl boronic acid, 73.9 g (534.4 mmol) of potassium carbonate, and 12.4 g (10.7 mmol) of tetrakis(triphenylphosphine) palladium(0) were added to 600 mL of 1,4-dioxane and 300 mL of water in a 2 L round-bottom flask, and then heated under reflux in a nitrogen atmosphere for 12 hours. The resulting mixture was added to 1800 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain the intermediate A-2-2 (54.2 g, Yield: 71%).

calcd. C22H13ClN2O: C, 74.06; H, 3.67; Cl, 9.94; N, 7.85; O, 4.48. found: C, 74.03; H, 3.65; Cl, 9.91; N, 7.80; O, 4.43.

Synthesis of Intermediate A-2-3

The intermediate A-2-2 (50.0 g, 140.1 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane (42.7 g, 168.2 mmol), potassium acetate (KOAc, 42.7 g, 420.2 mmol) and 1,1′-bis(diphenylphosphino) ferrocene-palladium(II) dichloride (6.9 g, 8.4 mmol), and tricyclohexyl phosphine (5.9 g, 21.0 mmol) were in 500 mL of N,N-dimethylform amide in a 1 L flask, and then stirred at 130° C. for 24 hours. After the reaction was terminated, the reaction solution was extracted with water and EA (ethyl acetate), and the moisture was removed from the resultant organic layer using magnesium sulfate followed by concentrating the resultant, and the resultant was purified using column chromatography to obtain a white solid, the intermediate A-2-3 (40.3 g, Yield: 64%).

calcd. C28H25BN2O3: C, 75.01; H, 5.62; B, 2.41; N, 6.25; O, 10.71. found: C, 75.00; H, 5.62; B, 2.38; N, 6.22; O, 10.69.

Synthesis of Compound a-2

5.0 g (11.2 mmol) of the intermediate A-2-3, 4.4 g (11.2 mmol) of the intermediate A-2-4 (Manufacturer: UMT), 3.9 g (27.9 mmol) of potassium carbonate, and 0.7 g (0.6 mmol) of tetrakis(triphenylphosphine) palladium(0) were added to 30 mL of 1,4-dioxane and 15 mL of water in a 100 mL flask, and heated under reflux in a nitrogen atmosphere for 16 hours. The resulting mixture was added to 100 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain Compound a-2 (5.1 g, Yield: 72%).

calcd. C43H27N5O: C, 82.02; H, 4.32; N, 11.12; O, 2.54. found: C, 82.01; H, 4.29; N, 11.07; O, 2.52.

Synthesis Example 2
Synthesis of Compound a-3

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Synthesis of Intermediate A-3-1

The intermediate A-2-3 20.0 g (44.6 mmol), 1-bromo-3-iodobenzene 12.6 g (44.6 mmol), potassium carbonate 15.4 g (111.5 mmol), and 2.4 g (2.6 mmol) of tetrakis(triphenylphosphine) palladium(0) were added to 140 mL of 1,4-dioxane and 70 mL of water in a 500 mL round-bottom flask, and then heated under reflux in a nitrogen atmosphere for 12 hours. The resulting mixture was added to 400 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain intermediate A-3-1 (16.4 g, Yield: 77%).

calcd. C28H17BrN2O: C, 70.45; H, 3.59; Br, 16.74; N, 5.87; O, 3.35. found: C, 70.44; H, 3.56; Br, 16.73; N, 5.83; O, 3.32.

Synthesis of Intermediate A-3-2

The intermediate A-3-1 (16.4 g, 36.7 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi (1,3,2-dioxaborolane (11.2 g, 44.0 mmol), potassium acetate (KOAc, 10.8 g, 110.0 mmol) and 1,1′-bis(diphenylphosphino) ferrocene-palladium(II) dichloride (1.8 g, 2.2 mmol) were added to 150 mL of N,N-dimethylform amide in a 250 mL flask, and stirred at 130° C. for 24 hours. After the reaction was terminated, the reaction solution was extracted with water and EA, and the moisture was removed from the resultant organic layer using magnesium sulfate followed by concentrating the resultant, and the resultant was purified using column chromatography to obtain a white solid, intermediate A-3-2 (15.2 g, Yield: 79%).

calcd. C34H29BN2O3: C, 77.87; H, 5.57; B, 2.06; N, 5.34; O, 9.15. found: C, 77.83; H, 5.57; B, 2.04; N, 5.32; O, 9.10.

Synthesis of Compound a-3

5.0 g (9.5 mmol) of the intermediate A-3-2, 3.7 g (9.5 mmol) of the intermediate A-2-4, 3.3 g (23.8 mmol) of potassium carbonate, and 0.6 g (0.5 mmol) of tetrakis(triphenylphosphine) palladium(0) were added to 30 mL of 1,4-dioxane and 15 mL of water in a 100 mL flask, and heated under reflux in a nitrogen atmosphere for 16 hours. The resulting mixture was added to 100 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain Compound a-3 (4.9 g, Yield: 73%). calcd. C49H31N5O: C, 83.38; H, 4.43; N, 9.92; O, 2.27. found: C, 83.34; H, 4.42; N, 9.90; O, 2.24.

Synthesis Example 3
Synthesis of Compound a-6

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Compound a-6 (4.2 g, Yield: 68%) was synthesized in the same method as in the synthesis of Compound a-2 in Synthesis Example 1, except that the intermediate A-6-1 (Manufacturer: UMT) was used instead of the intermediate A-2-4.

calcd. C₄₄H₂₈N₄O: C, 84.06; H, 4.49; N, 8.91; O, 2.54. found: C, 84.01; H, 4.46; N, 8.88; O, 2.53.

Synthesis Example 4
Synthesis of Compound a-7

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Compound A-7 (4.6 g, Yield: 65%) was synthesized in the same method as in the synthesis of Compound a-3 in Synthesis Example 2, except that the intermediate A-6-1 was used instead of the intermediate A-2-4.

calcd. C₅₀H₃₂N₄O: C, 85.20; H, 4.58; N, 7.95; O, 2.27. found: C, 85.18; H, 4.52; N, 7.94; O, 2.22.

Synthesis Example 5
Synthesis of Compound a-19

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Synthesis of Intermediate A-19-1

50.0 g (209.2 mmol) of the intermediate A, 32.7 g (209.15 mmol) of 3-chlorophenyl boronic acid, 72.3 g (522.9 mmol) of potassium carbonate, and 12.1 g (10.5 mmol) of tetrakis(triphenylphosphine) palladium(0) were added to 600 mL of 1,4-dioxane and 300 mL of water in a 2000 mL flask, and heated under reflux in a nitrogen atmosphere at 55° C. for 16 hours. The resulting mixture was added to 2000 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain the intermediate A-19-1 (48.8 g, Yield: 74%).

calcd. C16H8C12N2O: C, 60.98; H, 2.56; Cl, 22.50; N, 8.89; O, 5.08. found: C, 60.93; H, 2.55; Cl, 22.50; N, 8.83; O, 5.05.

Synthesis of Intermediate A-19-2

48.0 g (152.3 mmol) of the intermediate A-19-1, 18.6 g (152.3 mmol) of phenyl boronic acid, 52.6 g (380.8 mmol) of potassium carbonate, and 8.8 g (7.6 mmol) of tetrakis(triphenylphosphine) palladium(0) were added to 400 mL of 1,4-dioxane and 200 mL of water in a 1000 mL round-bottom flask, and heated under reflux in a nitrogen atmosphere for 16 hours. The resulting mixture was added to 1200 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain the intermediate A-19-2 (39.1 g, Yield: 72%).

calcd. C22H13ClN2O: C, 74.06; H, 3.67; Cl, 9.94; N, 7.85; O, 4.48. found: C, 74.01; H, 3.66; Cl, 9.91; N, 7.81; O, 4.44.

Synthesis of Intermediate A-19-3

Intermediate A-19-2 (39.0 g, 109.3 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi (1,3,2-dioxaborolane (33.3 g, 131.2 mmol), potassium acetate (KOAc, 32.2 g, 327.9 mmol) and 1,1′-bis(diphenylphosphino) ferrocene-palladium(II) dichloride (5.4 g, 6.6 mmol), and tricyclohexylphosphine (4.6 g, 16.4 mmol) were added to 500 mL of N,N-dimethylform amide in a 1 L flask, and stirred at 130° C. for 24 hours. After the reaction was terminated, the reaction solution was extracted with water and EA, and the moisture was removed from the resultant organic layer using magnesium sulfate followed by concentrating the resultant, and the resultant was purified using column chromatography to obtain a white solid, intermediate A-19-3 (37.0 g, Yield: 76%).

calcd. C28H25BN2O3: C, 75.01; H, 5.62; B, 2.41; N, 6.25; O, 10.71. found: C, 74.99; H, 5.60; B, 2.39; N, 6.24; O, 10.68.

Synthesis of Intermediate A-19-4

37.0 g (82.5 mmol) of A-19-3, 23.4 g (82.5 mmol) of 1-bromo-3-iodobenzene, 28.5 g (206.5 mmol) of potassium carbonate, 4.8 g (4.1 mmol) of tetrakis(triphenylphosphine) palladium(0) were added to 280 mL of 1,4-dioxane and 140 mL of water in a 500 mL round-bottom flask, and heated under reflux in a nitrogen atmosphere for 16 hours. The resulting mixture was added to 850 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain the intermediate A-19-4 (26.8 g, Yield: 68%).

calcd. C₂₈H₁₇BrN₂O: C, 70.45; H, 3.59; Br, 16.74; N, 5.87; O, 3.35. found: C, 70.42; H, 3.55; Br, 16.71; N, 5.82; O, 3.34.

Synthesis of Intermediate A-19-5

Intermediate A-19-4 (15.0 g, 31.4 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi (1,3,2-dioxaborolane (9.6 g, 37.7 mmol), potassium acetate (KOAc, 9.3 g, 94.3 mmol) and 1,1′-bis(diphenylphosphino) ferrocene-palladium(II)dichloride (1.5 g, 1.9 mmol) were added to 150 mL of N,N-dimethylform amide in a 250 mL flask, and stirred at 130° C. for 24 hours. After the reaction was terminated, the reaction solution was extracted with water and EA, and the moisture was removed from the resultant organic layer using magnesium sulfate followed by concentrating the resultant, and the resultant was purified using column chromatography to obtain a white solid, intermediate A-19-5 (11.1 g, Yield: 67%).

calcd. C34H29BN2O3: C, 77.87; H, 5.57; B, 2.06; N, 5.34; O, 9.15. found: C, 77.85; H, 5.54; B, 2.03; N, 5.32; O, 9.13.

Synthesis of Compound a-19

15.0 g (28.6 mmol) of the intermediate A-19-5, 11.1 g (28.6 mmol) of the intermediate A-2-4, 9.9 g (71.5 mmol) of potassium carbonate, and 1.7 g (1.4 mmol) of tetrakis(triphenylphosphine) palladium(0) were added to 100 mL of 1,4-dioxane and 50 mL of water in a 250 mL flask, and heated under reflux in a nitrogen atmosphere for 16 hours. The resulting mixture was added to 300 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain Compound a-19 (14.3 g, Yield: 71%).

calcd. C₄₉H₃₁N₅O: C, 83.38; H, 4.43; N, 9.92; O, 2.27. found: C, 83.35; H, 4.41; N, 9.89; O, 2.22.

Synthesis Example 6
Synthesis of Compound a-39

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Compound a-39 (5.7 g, Yield: 68%) was synthesized in the same method as in the synthesis of Compound a-3 in Synthesis Example 2, except that the intermediate A-39-1 was used instead of the intermediate A-2-4.

calcd. C₄₈H₃₀N₄O: C, 84.93; H, 4.45; N, 8.25; O, 2.36. found: C, 84.90; H, 4.43; N, 8.24; O, 2.32.

Synthesis Example 7
Synthesis of Compound a-55

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Compound A-55 (6.1 g, Yield: 72%) was synthesized in the same method as in the synthesis of Compound a-3 in Synthesis Example 2, except that the intermediate A-55-1 was used instead of the intermediate A-2-4.

calcd. C₄₇H₃₀N₄O: C, 84.66; H, 4.54; N, 8.40; O, 2.40. found: C, 84.61; H, 4.47; N, 8.37; O, 2.40.

Synthesis Example 8
Synthesis of Compound b-2

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Synthesis of Intermediate B(1)(benzo-1H-thieno [3,2-d]pyrimidine-2,4-dione)

A mixture of 237.5 g (1.15 mol) of benzo-methyl 3-amino-2-thiophenecarboxylate and 397.3 g (5.75 mol) of urea was stirred in a 2-L round-bottom flask at about 200° C. for about 2 hours. After the high-temperature reaction product was cooled down to room temperature, a sodium hydroxide solution was added thereto, followed by filtration to remove impurities and acidification with HCl. The resulting precipitate was dried to obtain Intermediate B(1) (35 g, Yield: 75%).

calcd. C₁₀H₆N₂O₂S: C, 55.04; H, 2.77; N, 12.84; O, 14.66; S, 14.69. found: C, 55.01; H, 2.79; N, 12.81; O, 14.69; S, 14.70.

Synthesis of Intermediate B (benzo-2,4-dichloro-thieno [3,2-d]pyrimidine)

175 g (0.80 mol) of Intermediate B(1) (benzo-1H-thieno [3,2-d]pyrimidine-2,4-dione) and 1000 mL of phosphorus oxychloride were mixed in a 3000-mL round-bottom flask and stirred under reflux for about 8 hours. The reaction product was cooled down to room temperature, and poured into ice/water with stirring to obtain a precipitate. The resulting reaction precipitate was filtered to obtain Intermediate B ((benzo-2,4-dichloro-thieno [3,2-d]pyrimidine) in white solid form (175 g, Yield: 85%). Intermediate B was identified using elemental analysis and nuclear magnetic resonance (NMR). The results are as follows.

calcd. C₁₀H₄Cl₂N₂S: C, 47.08; H, 1.58; Cl, 27.79; N, 10.98; S, 12.57. found: C, 47.03; H, 1.61; Cl, 27.81; N, 10.98; S, 12.60.

300 MHz (CDCl₃, ppm): 7.63 (t, 1H), 7.76 (t, 4H), 7.95 (d, 1H), 8.53 (d, 1H)

Synthesis of Intermediate B-2-1

70.0 g (274.4 mmol) of the intermediate B, 33.5 g (274.4 mmol) of phenyl boronic acid, 94.8 g (686.0 mmol) of potassium carbonate, and 15.9 g (13.7 mmol) of tetrakis(triphenylphosphine) palladium(0) were 800 mL of 1,4-dioxane and 400 mL of water in a 2000 mL flask, and heated under reflux in a nitrogen atmosphere at 50° C. for 24 hours. The resulting mixture was added to 3000 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain the intermediate B-2-1 (59.4 g, Yield: 73%).

calcd. C16H9ClN2S: C, 64.75; H, 3.06; Cl, 11.95; N, 9.44; S, 10.80. found: C, 64.70; H, 3.02; Cl, 11.93; N, 9.40; S, 10.73.

Synthesis of Intermediate B-2-2

59.0 g (198.8 mmol) of the intermediate B-2-1, 31.1 g (198.8 mmol) of 3-chlorophenyl boronic acid, 68.7 g (497.0 mmol) of potassium carbonate, and 11.5 g (9.9 mmol) of tetrakis(triphenylphosphine) palladium(0) were added to 600 mL of 1,4-dioxane and 300 mL of water in a 2 L round-bottom flask, and heated under reflux in a nitrogen atmosphere for 16 hours. The resulting mixture was added to 2000 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain the intermediate B-2-2 (51.2 g, Yield: 69%).

calcd. C22H13ClN2S: C, 70.87; H, 3.51; Cl, 9.51; N, 7.51; S, 8.60. found C, 70.84; H, 3.46; Cl, 9.50; N, 7.47; S, 8.58.

Synthesis of Intermediate B-2-3

Intermediate B-2-2 (50.0 g, 134.1 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane (40.9 g, 160.9 mmol), potassium acetate (KOAc, 39.5 g, 402.3 mmol) and 1,1′-bis(diphenylphosphino) ferrocene-palladium(II) dichloride (6.6 g, 8.1 mmol), and tricyclohexylphosphine (5.6 g, 20.1 mmol) were added to 500 mL of N,N-dimethylform amide in a 1 L flask, and stirred at 130° C. for 24 hours. After the reaction was terminated, the reaction solution was extracted with water and EA, and the moisture was removed from the resultant organic layer using magnesium sulfate followed by concentrating the resultant, and the resultant was purified using column chromatography to obtain a white solid, intermediate B-2-3 (40.3 g, Yield: 69%).

calcd. C28H25BN2O2S: C, 72.42; H, 5.43; B, 2.33; N, 6.03; O, 6.89; S, 6.90.

found: C, 72.40; H, 5.42; B, 2.32; N, 6.00; O, 6.82; S, 6.85.

Synthesis of Compound b-2

5.0 g (10.8 mmol) of the intermediate B-2-3, 4.2 g (10.8 mmol) of the intermediate A-2-4, 3.7 g (27.0 mmol) of potassium carbonate, and 0.6 g (0.5 mmol) of tetrakis(triphenylphosphine) palladium(0) were added to 40 mL of 1,4-dioxane and 20 mL of water in a 100 mL flask, and heated under reflux in a nitrogen atmosphere for 16 hours. The resulting mixture was added to 150 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain compound b-2 (4.7 g, Yield: 68%).

calcd. C43H27N5S: C, 79.98; H, 4.21; N, 10.84; S, 4.97. found: C, 79.95; H, 4.20; N, 10.81; S, 4.92.

Synthesis Example 9
Synthesis of Compound b-3

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Synthesis of Intermediate B-3-1

20.0 g (43.1 mmol) of the intermediate B-2-3, 12.2 g (43.1 mmol) of 1-bromo-3-iodobenzene, 14.9 g (107.7 mmol) of potassium carbonate, and 2.5 g (2.2 mmol) of tetrakis(triphenylphosphine) palladium(0) were added to 140 mL of 1,4-dioxane and 70 mL of water in 500 mL round-bottom flask, and heated under reflux in a nitrogen atmosphere for 18 hours. The resulting mixture was added to 450 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain the intermediate B-3-1 (15.9 g, Yield: 75%).

calcd. C28H17BrN2S: C, 68.16; H, 3.47; Br, 16.19; N, 5.68; S, 6.50. found: C, 68.12; H, 3.46; Br, 16.18; N, 5.63; S, 6.43.

Synthesis of Intermediate B-3-2

Intermediate B-3-1 (15.9 g, 32.2 mmol), 4,4,4′,4, 5,5,5′,5′-octamethyl-2,2′-bi (1,3,2-dioxaborolane (9.8 g, 38.7 mmol), potassium acetate (KOAc, 9.5 g, 96.7 mmol) and 1,1′-bis(diphenylphosphino) ferrocene-palladium(II) dichloride (1.6 g, 1.9 mmol) were added to 150 mL of N,N-dimethylform amide in a 250 mL flask, and stirred at 130° C. for 24 hours. After the reaction was terminated, the reaction solution was extracted with water and EA, and the moisture was removed from the resultant organic layer using magnesium sulfate followed by concentrating the resultant, and the resultant was purified using column chromatography to obtain a white solid, intermediate B-3-2 (13.2 g, Yield: 76%).

calcd. C34H29BN2O2S: C, 75.56; H, 5.41; B, 2.00; N, 5.18; O, 5.92; S, 5.93.

found: C, 75.51; H, 5.40; B, 1.95; N, 5.16; O, 5.90; S, 5.92.

Synthesis of Compound b-3

4.0 g (7.4 mmol) of the intermediate B-3-2, 2.9 g (7.4 mmol) of the intermediate A-2-4, 2.6 g (18.5 mmol) of potassium carbonate, and 0.4 g (0.4 mmol) of tetrakis(triphenylphosphine) palladium(0) were added to 20 mL of 1,4-dioxane and 10 mL of water in a 100 mL flask, and heated under reflux in a nitrogen atmosphere for 16 hours. The resulting mixture was added to 100 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain Compound b-3 (3.7 g, yield: 71%).

calcd. C49H31N5S: C, 81.53; H, 4.33; N, 9.70; S, 4.44. found: C, 81.51; H, 4.30; N, 9.64; S, 4.41.

Synthesis Example 10
Synthesis of Compound b-6

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Compound b-6 (4.6 g, Yield: 65%) was synthesized in the same method as in the synthesis of Compound b-2 in Synthesis Example 8, except that the intermediate A-6-1 was used instead of the intermediate A-2-4.

calcd. C44H28N4S: C, 81.96; H, 4.38; N, 8.69; S, 4.97. found: C, 81.92; H, 4.37; N, 8.65; S, 4.91.

Synthesis Example 11
Synthesis of Compound b-7

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Compound b-7 (4.7 g, Yield: 68%) was synthesized in the same method as in the synthesis of Compound b-3 in Synthesis Example 9, except that the intermediate A-6-1 was used instead of the intermediate A-2-4.

calcd. C50H32N4S: C, 83.31; H, 4.47; N, 7.77; S, 4.45. found: C, 83.30; H, 4.46; N, 7.76; S, 4.41.

Synthesis Example 12
Synthesis of Compound b-19

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Synthesis of Intermediate B-19-1

50.0 g (196.0 mmol) of the intermediate B, 30.7 g (196.0 mmol) of 3-chlorophenyl boronic acid, 67.7 g (490.0 mmol) of potassium carbonate, and 11.3 g (9.8 mmol) of tetrakis(triphenylphosphine) palladium(0) were added to 600 mL of 1,4-dioxane and 300 mL of water in a 2000 mL flask, and heated under reflux in a nitrogen atmosphere at 55° C. for 16 hours. The resulting mixture was added to 2000 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain the intermediate B-19-1 (46.7 g, Yield: 72%).

calcd. C16H8Cl2N2S: C, 58.02; H, 2.43; Cl, 21.41; N, 8.46; S, 9.68. found: C, 58.00; H, 2.42; Cl, 21.40; N, 8.43; S, 9.61.

Synthesis of Intermediate B-19-2

46.0 g (138.9 mmol) of the intermediate B-19-1, 16.9 g (138.9 mmol) of phenyl boronic acid, 48.0 g (347.2 mmol) of potassium carbonate, and 8.0 g (6.9 mmol) of tetrakis(triphenylphosphine) palladium(0) were added to 400 mL of 1,4-dioxane and 200 mL of water in a 1000 mL round-bottom flask, and heated under reflux in a nitrogen atmosphere for 16 hours. The resulting mixture was added to 1200 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain the intermediate B-19-2 (38.8 g, yield: 75%).

calcd. C22H13ClN2S: C, 70.87; H, 3.51; Cl, 9.51; N, 7.51; S, 8.60. found: C, 70.83; H, 3.48; Cl, 9.45; N, 7.50; S, 8.58.

Synthesis of Intermediate B-19-3

Intermediate B-19-2 (38.0 g, 101.9 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi (1,3,2-dioxaborolane (31.1 g, 122.3 mmol), potassium acetate (KOAc, 30.0 g, 305.7 mmol) and 1,1′-bis(diphenylphosphino) ferrocene-palladium(II) dichloride (5.09 g, 6.1 mmol), and tricyclohexylphosphine (4.3 g, 15.3 mmol) were 500 mL of N,N-dimethylform amide in a 1 L flask, and stirred at 130° C. for 24 hours. After the reaction was terminated, the reaction solution was extracted with water and EA, and the moisture was removed from the resultant organic layer using magnesium sulfate followed by concentrating the resultant, and the resultant was purified using column chromatography to obtain a white solid, intermediate B-19-3 (34.1 g, Yield: 72%).

calcd. C28H25BN2O2S: C, 72.42; H, 5.43; B, 2.33; N, 6.03; O, 6.89; S, 6.90. found: C, 72.40; H, 5.38; B, 2.30; N, 6.01; O, 6.83; S, 6.86.

Synthesis of Intermediate B-19-4

34.0 g (73.2 mmol) of the intermediate B-19-3, 20.7 g (73.2 mmol) of 1-bromo-3-iodobenzene, 25.3 g (183.0 mmol) of potassium carbonate, and 4.2 g (3.7 mmol) of tetrakis(triphenylphosphine) palladium(0) were added to 240 mL of 1,4-dioxane and 120 mL of water in a 500 mL round-bottom flask, and heated under reflux in a nitrogen atmosphere for 16 hours. The resulting mixture was added to 720 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain the intermediate B-19-4 (24.9 g, Yield: 69%).

calcd. C28H17BrN2S: C, 68.16; H, 3.47; Br, 16.19; N, 5.68; S, 6.50. found: C, 68.15; H, 3.44; Br, 16.16; N, 5.61; S, 6.43.

Synthesis of Intermediate B-19-5

Intermediate B-19-4 (15.0 g, 30.4 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi (1,3,2-dioxaborolane (9.3 g, 36.5 mmol), potassium acetate (KOAc, 9.0 g, 91.2 mmol) and 1,1′-bis(diphenylphosphino) ferrocene-palladium(II) dichloride (1.5 g, 1.8 mmol) were 150 mL of N,N-dimethylform amide in a 250 mL flask, and stirred at 130° C. for 24 hours. After the reaction was terminated, the reaction solution was extracted with water and EA, and the moisture was removed from the resultant organic layer using magnesium sulfate followed by concentrating the resultant, and the resultant was purified using column chromatography to obtain a white solid, intermediate B-19-5 (12.0 g, Yield: 73%).

calcd. C34H29BN2O2S: C, 75.56; H, 5.41; B, 2.00; N, 5.18; O, 5.92; S, 5.93.

found: C, 75.52; H, 5.39; B, 1.95; N, 5.13; O, 5.88; S, 5.91.

Synthesis of Compound b-19

15.0 g (27.8 mmol) of the intermediate B-19-5, 10.8 g (27.8 mmol) of the intermediate A-2-4, 9.6 g (69.4 mmol) of potassium carbonate, and 1.6 g (1.4 mmol) of tetrakis(triphenylphosphine) palladium(0) were added to 80 mL of 1,4-dioxane and 40 mL of water in a 250 mL flask, and heated under reflux in a nitrogen atmosphere for 16 hours. The resulting mixture was added to 250 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain Compound b-19 (13.8 g, Yield: 69%).

calcd. C49H31N5S: C, 81.53; H, 4.33; N, 9.70; S, 4.44. found: C, 81.50; H, 4.31; N, 9.63; S, 4.41.

Synthesis Example 13
Synthesis of Compound b-39

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Compound b-39 (4.6 g, Yield: 70%) was synthesized in the same method as in the synthesis of Compound b-3 in Synthesis Example 9, except that the intermediate A-39-1 was used instead of the intermediate A-2-4.

calcd. C48H30N4S: C, 82.97; H, 4.35; N, 8.06; S, 4.61. found: C, 82.97; H, 4.34; N, 8.03; S, 4.59.

Synthesis Example 14
Synthesis of Compound b-55

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Compound b-55 (5.8 g, Yield: 68%) was synthesized in the same method as in the synthesis of Compound b-3 in Synthesis Example 9, except that the intermediate A-55-1 was used instead of the intermediate A-2-4.

calcd. C47H30N4S: C, 82.67; H, 4.43; N, 8.21; S, 4.70. found: C, 82.65; H, 4.41; N, 8.20; S, 4.63.

Synthesis Example 15
Synthesis of Compound c-2

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Synthesis of Intermediate C-2

45.0 g (171.7 mmol) of the intermediate C-1, 30.0 g (163.5 mmol) of 2,4,6-trichloropyrimidine, 56.5 g (408.9 mmol) of potassium carbonate, 9.5 g (8.2 mmol) of tetrakis (triphenylphosphine)palladium were added to 540 mL of 1,4-dioxane and 270 mL of water in a 2000 mL flask, and heated under reflux in a nitrogen atmosphere for 12 hours. The resulting mixture was added to 1000 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain the intermediate C-2 (37.0 g, Yield: 76%).

Calcd. C12H12Cl2N2Si: C, 50.89; H, 4.27; Cl, 25.03; N, 9.89; Si, 9.92. found: C, 50.32; H, 4.22; Cl, 24.98; N, 9.73; Si, 9.84.

Synthesis of Intermediate C

37.0 g (130.6 mmol) of the intermediate C-2, and 2.4 g (2.6 mmol) of chlorotris(triphenylphosphine)rhodium (I) were added to a 1000 mL flask, 600 mL of 1,4-dioxane were added in a dropwise fashion, and the mixture was heated under reflux in a nitrogen atmosphere for 8 hours. After the reaction was terminated, an organic layer was removed, and Intermediate C (20.2 g, Yield: 55%) was obtained using column chromatography.

calcd. C12H10Cl2N2Si: C, 51.25; H, 3.58; Cl, 25.21; N, 9.96; Si, 9.99. found: C, 51.15; H, 3.53; Cl, 25.16; N, 9.90; Si, 9.93.

Synthesis of Compound c-2

Compound c-2 (5.3 g, Yield: 68%) was synthesized in the same method as in Synthesis Example 1, except that the intermediate C was used instead of the intermediate A.

calcd. C45H33N5Si: C, 80.45; H, 4.95; N, 10.42; Si, 4.18. found: C, 80.43; H, 4.94; N, 10.41; Si, 4.15.

Synthesis Example 16
Synthesis of Compound d-18

A compound d-18 provided as specific examples of a compound of the present invention was synthesized through the following five steps.

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Synthesis of Intermediate D-2

50.0 g (222.2 mmol) of the intermediate D-1 (Manufacturer: TCI Inc.), 50.1 g (233.3 mmol) of 4,4,5,5-tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxaborane, 76.8 g (555.4 mmol) of potassium carbonate, and 12.8 g (11.1 mmol) of tetrakis (triphenylphosphine)palladium were added to 700 mL of 1,4-dioxane and 350 mL of water in a 2000 mL flask, and heated under reflux in a nitrogen atmosphere for 12 hours. The resulting mixture was added to 3000 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain the intermediate D-2 (54.5 g, Yield: 75%).

Calcd. C16H10ClN3O2: C, 61.65; H, 3.23; Cl, 11.37; N, 13.48; O, 10.27. found; C, 61.23; H, 3.15; Cl, 11.37; N, 13.21; O, 10.20.

Synthesis of Intermediate D-3

50.0 g (160.4 mmol) of the intermediate D-2, 25.1 g (160.4 mmol) of 3-chloro phenylboronic acid, 55.4 g (401.0 mmol) of potassium carbonate, and 9.3 g (8.0 mmol) of tetrakis (triphenylphosphine)palladium were added to 500 mL of 1,4-dioxane and 250 mL of water in a 2000 mL flask, and heated under reflux in a nitrogen atmosphere for 16 hours. The resulting mixture was added to 1500 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain the intermediate D-3 (42.9 g, Yield: 69%).

Calcd. C22H14ClN3O2: C, 68.13; H, 3.64; Cl, 9.14; N, 10.83; O, 8.25. found: C, 68.09; H, 3.62; Cl, 9.13; N, 10.81; O, 8.23.

Synthesis of Intermediate D-4

Intermediate D-3 (20.0 g, 51.6 mmol) and triphenylphosphine (40.6 g, 154.7 mmol) were added to a 250 mL flask, 120 mL of 1,2-dichlorobenzene (DCB) was added, thereto, and the mixture was stirred at 150° C. for 16 hours after exchanged with nitrogen. The resultant was cooled down to room temperature after distillating and removing 1,2-dichlorobenzene, dissolved in a small amount of toluene, and purified through column chromatography (hexane) to obtain the intermediate D-4 (9.5 g, Yield: 52%).

Calcd. C22H14ClN3: C, 74.26; H, 3.97; Cl, 9.96; N, 11.81. found: C, 74.21; H, 3.94; Cl, 9.91; N, 11.75.

Synthesis of Intermediate D-5

8.4 g (23.2 mmol) of the intermediate D-4, 3.6 g (23.2 mmol) of bromobenzene, 4.5 g (46.3 mmol) of sodium t-butoxide, 1.3 g (2.3 mmol) of Pd(dba)₂, and 1.9 mL (50% in toluene) of tri t-butylphosphine were added to 150 mL of xylene in a 250 mL round-bottom flask, and then heated under reflux in a nitrogen atmosphere for 15 hours. The resulting mixture was added to 300 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain the intermediate D-5 (6.0 g, Yield: 73%). The elemental analysis result of the intermediate D-5 is as follows.

calcd. C28H18ClN3: C, 77.86; H, 4.20; Cl, 8.21; N, 9.73. found: C, 77.82; H, 4.16; Cl, 8.20; N, 9.71.

Synthesis of Compound d-18

6.0 g (13.9 mmol) of the intermediate D-5, 6.1 g (13.9 mmol) of the intermediate D-6 (intermediate A-2-4 was synthesized according to the reaction scheme of the General Formula A), 4.8 g (34.7 mmol) of potassium carbonate, and 0.8 g (0.7 mmol) of tetrakis (triphenylphosphine)palladium were added to 50 mL of 1,4-dioxane and 25 mL of water in a 250 mL flask, and heated under reflux in a nitrogen atmosphere for 16 hours. The resulting mixture was added to 150 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain Compound d-18 (3.4 g, Yield: 35%).

Calcd. C₄₉H₃₂N₆: C, 83.50; H, 4.58; N, 11.92. found: C, 83.47; H, 4.55; N, 11.91.

Synthesis Example 17
Synthesis of Compound e-2

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Synthesis of Intermediate E-2

Chlorosulfonylisocyanate (23.7 mL, 274.6 mmol) was added in a dropwise fashion to a solution including an intermediate E-1 (35.0 g, 183.1 mmol) in dichloromethane (1000 mL) in a 2000 mL round flask at −78° C. The reactant was slowly heated to room temperature and stirred for 2 hours. After concentrating the reactant, 6N (300 mL) was added to the residue, and the mixture was stirred at 100° C. for 1 hour. The reaction mixture was cooled down to room temperature and neutralized with a saturated NaHCO₃aqueous solution. Then, a solid produced therein was filtered to obtain the intermediate E-2 (43.2 g, Yield: 88%), a beige solid.

calcd. C10H9NO3: C, 62.82; H, 4.74; N, 7.33; O, 25.11. found: C, 62.82; H, 4.74; N, 7.33; O, 25.11.

Synthesis of Intermediate E-3

The intermediate E-2 (40.0 g, 0.19 mol) was suspended in 1000 mL of methanol in a 1000 mL round flask, and 300 mL of 2 M NaOH was added thereto in a dropwise fashion. The reaction mixture was refluxed and stirred for 3 hours. The resultant was cooled down to room temperature and acidified into pH 3 by using Conc. HCl. After concentrating the mixture, methanol was slowly added to the residue in a dropwise fashion to precipitate a solid. The solid was filtered and dried to obtain the intermediate E-3 (39.0 g, Yield: 85%).

calcd. C11H10N2O4: C, 56.41; H, 4.30; N, 11.96; O, 27.33. found: C, 56.40; H, 4.20; N, 11.92; O, 27.31.

Synthesis of Intermediate E-4

A mixture of the intermediate E-3 (39.0 g, 191.0 mmol) and 200 mL of phosphorous oxychloride was refluxed and stirred for 8 hours in a 500 mL round flask. The reaction mixture was cooled down to room temperature and then, poured into ice/water while strongly stirred to produce a precipitate. The obtained reactant was filtered to obtain the intermediate E-4. (40.7 g, 89%, a white solid)

calcd. C10H4Cl2N2O: C, 50.24; H, 1.69; Cl, 29.66; N, 11.72; O, 6.69. found: C, 50.21; H, 1.65; Cl, 29.63; N, 11.64; O, 6.62.

Synthesis of Intermediate E-5

10.0 g (41.8 mmol) of the intermediate E-4, 5.4 g (43.9 mmol) of phenylboronic acid, 14.5 g (104.6 mmol) of potassium carbonate, and 2.4 g (2.1 mmol) of tetrakis(triphenylphosphine) palladium(0) were added to 140 mL of 1,4-dioxane and 70 mL of water in a 500 mL flask and then, heated at 60° C. under a nitrogen stream for 10 hours. The resulting mixture was added to 450 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain the intermediate E-5 (8.0 g, Yield: 65%).

calcd. C16H9ClN2O: C, 68.46; H, 3.23; Cl, 12.63; N, 9.98; O, 5.70. found: C, 68.40; H, 3.22; Cl, 12.61; N, 9.94; O, 5.70.

Synthesis of Intermediate E-6

10.0 g (35.6 mmol) of the intermediate E-5, 5.6 g (35.6 mmol) of 3-chloro-phenylboronic acid (TCI Inc.), 12.3 g (89.1 mmol) of potassium carbonate, and 2.1 g (1.8 mmol) of tetrakis(triphenylphosphine) palladium(0) were added to 100 mL of 1,4-dioxane and 50 mL of water in a 500 mL flask, and heated under reflux in a nitrogen atmosphere at 55° C. for 16 hours. The resulting mixture was added to 500 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain the intermediate E-6 (8.6 g, Yield: 68%).

calcd. C22H13ClN2O: C, 74.06; H, 3.67; Cl, 9.94; N, 7.85; O, 4.48. found: C, 74.02; H, 3.65; Cl, 9.90; N, 7.81; O, 4.46.

Synthesis of Compound e-2

Compound e-2 (3.9 g, Yield: 37%) was synthesized in the same method as in the synthesis of Compound a-2 in Synthesis Example 1, except that the intermediates E-6 and D-6 were used instead of the intermediates A-2-3 and A-2-4, respectively.

calcd. C₄₃H₂₇N₅O: C, 82.02; H, 4.32; N, 11.12; O, 2.54. found: C, 81.99; H, 4.28; N, 11.10; O, 2.52.

Synthesis Example 18
Synthesis of Compound e-3

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Synthesis of Intermediate E-7

20.0 g (56.1 mmol) of the intermediate E-6, 17.1 g (67.3 mmol) of 4,4,4′,4′,5,5,5′,5 ′-octamethyl-2,2′-bi (1,3,2-dioxaborolane, 16.5 g (168.2 mmol) of potassium acetate (KOAc), 2.8 g (3.4 mmol) of 1,1′-bis(diphenylphosphino) ferrocene-palladium(II) dichloride, and 2.4 g (8.4 mmol) of tricyclohexylphosphine were added to 280 mL of N,N-dimethylform amide in a 500 mL flask, and stirred at 130° C. for 24 hours. After the reaction was terminated, the reaction solution was extracted with water and EA, and the moisture was removed from the resultant organic layer using magnesium sulfate followed by concentrating the resultant, and the resultant was purified using column chromatography to obtain a white solid, intermediate E-7 (18.1 g, Yield: 72%).

Calcd. C28H25BN2O3: C, 75.01; H, 5.62; B, 2.41; N, 6.25; O, 10.71. found: C, 75.01; H, 5.58; B, 2.39; N, 6.23; O, 10.70.

Synthesis of Intermediate E-8

18.0 g (40.2 mmol) of the intermediate E-7, 11.4 g (40.2 mmol) of 1-bromo-3-iodobenzene, 13.9 g (100.4 mmol) of potassium carbonate, and 2.3 g (2.0 mmol) of tetrakis(triphenylphosphine) palladium(0) were added to 120 mL of 1,4-dioxane and 60 mL of 1,4-dioxane in a 500 mL flask, and heated in a nitrogen atmosphere at about 65° C. for 16 hours. The resulting mixture was added to 500 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain the intermediate E-8 (13.6 g, Yield: 71%).

calcd. C₂₈H₁₇BrN₂O: C, 70.45; H, 3.59; Br, 16.74; N, 5.87; O, 3.35. found: C, 70.43; H, 3.58; Br, 16.71; N, 5.85; O, 3.32.

Synthesis of Compound e-3

13.0 g (27.2 mmol) of the intermediate E-8, 11.9 g (27.2 mmol) of the intermediate D-6, 9.4 g (68.1 mmol) of potassium carbonate, and 1.6 g (1.4 mmol) of tetrakis(triphenylphosphine) palladium(0) were added to 80 mL of 1,4-dioxane and 40 mL of water in a 250 mL flask, and heated in a nitrogen atmosphere at 65° C. for 16 hours. The resulting mixture was added to 250 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain Compound e-3 (12.7 g, Yield: 66%).

calcd. C₄₉H₃₁N₅O: C, 83.38; H, 4.43; N, 9.92; O, 2.27. found: C, 83.36; H, 4.40; N, 9.91; O, 2.22.

Synthesis Example 19
Synthesis of Compound f-2

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Synthesis of Intermediate F-2

A mixture of the intermediate F-1 (35.0 g, 0.17 mol) and urea (50.7 g, 0.84 mol) was stirred at 200° C. for 2 hours in a 250 mL round flask. The high temperature reaction mixture was cooled down to room temperature and poured into a sodium hydroxide solution, the mixture was filtered to remove impurities and then, acidified (HCl, 2N), and a precipitate obtained therefrom was dried to obtain the intermediate F-2 (18.9 g, Yield: 51%).

calcd. C10H6N2O2S: C, 55.04; H, 2.77; N, 12.84; O, 14.66; S, 14.69. found: C, 55.01; H, 2.77; N, 12.83; O, 14.65; S, 14.63.

Second Step: Synthesis of Intermediate F-3

100 mL of a mixture of the intermediate F-2 (18.9 g, 99.2 mmol) and phosphorous oxychloride was refluxed and stirred for 6 hours in a 250 mL round flask. The reaction mixture was cooled down to room temperature and then, poured into ice/water while strongly stirred to produce a precipitate. The obtained reactant was filtered, obtaining the intermediate F-3. (17.5 g, 85%, a white solid)

calcd. C10H4Cl2N2S: C, 47.08; H, 1.58; Cl, 27.79; N, 10.98; S, 12.57. found: C, 47.04; H, 1.53; Cl, 27.74; N, 10.96; S, 12.44.

Synthesis of Intermediate F-4

10.0 g (39.2 mmol) of the intermediate F-3, 5.3 g (43.1 mmol) of phenylboronic acid, 13.5 g (98.0 mmol) of potassium carbonate, and 2.3 g (2.0 mmol) of tetrakis(triphenylphosphine) palladium(0) were added to were added to 140 mL of 1,4-dioxane and 70 mL of water in a 500 mL flask, and heated in a nitrogen atmosphere at 60° C. for 10 hours. The resulting mixture was added to 450 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain the intermediate F-4 (8.0 g, Yield: 69%).

calcd. C16H9ClN2S: C, 64.75; H, 3.06; Cl, 11.95; N, 9.44; S, 10.80. found: C, 64.72; H, 3.06; Cl, 11.94; N, 9.42; S, 10.77.

Synthesis of Intermediate F-5

Intermediate F-5 (10.3 g, Yield: 65%) was synthesized in the same method as in the synthesis of the intermediate E-6 in Synthesis Example 17, except that the intermediate F-4 was used instead of the intermediate E-5.

calcd. C22H13ClN2S: C, 70.87; H, 3.51; Cl, 9.51; N, 7.51; S, 8.60. found: C, 70.83; H, 3.49; Cl, 9.47; N, 7.50; S, 8.54.

Synthesis of Compound f-2

Compound f-2 (4.1 g, Yield: 39%) was synthesized in the same method as in the synthesis of the compound e-2 in Synthesis Example 17, except that the intermediate F-5 was used instead of the intermediate E-6.

calcd. C43H27N5S: C, 79.98; H, 4.21; N, 10.84; S, 4.97. found: C, 79.94; H, 4.17; N, 10.82; S, 4.95.

Synthesis Example 20
Synthesis of Compound f-3

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Synthesis of Intermediate F-6

Intermediate F-6 (15.4 g, Yield: 74%) was synthesized in the same method as in the synthesis of the intermediate E-7 in Synthesis Example 18, except that the intermediate F-5 was used instead of the intermediate E-6.

Calcd. C28H25BN2O2S: C, 72.42; H, 5.43; B, 2.33; N, 6.03; O, 6.89; S, 6.90.

found: C, 72.39; H, 5.40; B, 2.31; N, 6.02; O, 6.85; S, 6.87.

Synthesis of Intermediate F-7

Intermediate F-7 (12.4 g, Yield: 71%) was synthesized in the same method as in the synthesis of the intermediate E-8 in Synthesis Example 18, except that the intermediate F-6 was used instead of the intermediate E-7.

calcd. C28H17BrN2S: C, 68.16; H, 3.47; Br, 16.19; N, 5.68; S, 6.50. found: C, 68.13; H, 3.45; Br, 16.15; N, 5.67; S, 6.50.

Synthesis of Compound f-3

Compound f-3 (9.3 g, Yield: 70%) was synthesized in the same method as in the synthesis of the compound e-3 in Synthesis Example 18, except that the intermediate F-7 was used instead of the intermediate E-8.

Calcd. C49H31N5S: C, 81.53; H, 4.33; N, 9.70; S, 4.44. found: C, 81.51; H, 4.30; N, 9.67; S, 4.42.

Synthesis of Second Host Compound
Synthesis Example 21
Synthesis of Compound A1

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16.62 g (51.59 mmol) of 3-bromo-N-phenylcarbazole, 17.77 g (61.91 mmol) of N-phenylcarbazole-3-ylboronic acid, and 200 mL of a mixture of tetrahydrofuran (THF) and toluene (1:1), and 100 mL of an aqueous solution of 2M potassium carbonate were mixed in a 500 mL round-bottom flask equipped with a stirrer in a nitrogen atmosphere, and 2.98 g (2.58 mmol) of tetrakis(triphenylphosphine)palladium(0) was added thereto, and heated under reflux in a nitrogen atmosphere for 12 hours. After completion of the reaction, the reaction product was added to methanol to obtain a solid by filtering. This solid was sufficiently washed with water and methanol, and then dried. The resulting product was dissolved in 1 L of chlorobenzene by heating, followed by filtration using silica gel and removing the solvent. The resulting product was dissolved in 500 mL of toluene by heating, followed by recrystallization to obtain Compound A1 (16.05 g, Yield: 64%).

calcd. C₃₆H₂₄N2: C, 89.23; H, 4.99; N, 5.78. found: C, 89.45; H, 4.89; N, 5.65.

Synthesis Example 22
Synthesis of Compound A2

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20.00 g (50.21 mmol) of 3-bromo-N-biphenylcarbazole, 18.54 g (50.21 mmol) of N-phenylcarbazole-3-boronic ester, and 175 mL of a mixture of tetrahydrofuran (THF) and toluene (1:1), and 75 mL of an aqueous solution of 2M potassium carbonate were mixed in a 500 mL round-bottom flask equipped with a stirrer in a nitrogen atmosphere, and 2.90 g (2.51 mmol) of tetrakis(triphenylphosphine)palladium(0) was added thereto, and heated under reflux in a nitrogen atmosphere for 12 hours. After completion of the reaction, the reaction product was added to methanol to obtain a solid by filtering. This solid was sufficiently washed with water and methanol, and then dried. The resulting product was dissolved in 700 mL of chlorobenzene by heating, followed by filtration using silica gel and removing the solvent. The resulting product was dissolved in 400 mL of chlorobenzene by heating, followed by recrystallization to obtain Compound A2 (19.15 g, Yield: 68%).

calcd. C₄₂H₂₈N₂: C, 89.97; H, 5.03; N, 5.00. found: C, 89.53; H, 4.92; N, 4.89.

Synthesis Example 23
Synthesis of Compound A5

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12.81 g (31.36 mmol) of N-phenyl-3,3-bicarbazole, 8.33 g (31.36 mmol) of 2-chloro-di-4,6-phenylpyridine, 6.03 g (62.72 mmol) of sodium t-butoxide, 1.80 g (3.14 mmol) of tris(dibenzylideneacetone)dipalladium, and 2.6 mL of tri-t-butylphosphine (50% in toluene) were added to 200 mL of xylene in a 500 mL round-bottom flask, and heated under reflux in a nitrogen atmosphere for 15 hours. The resulting mixture was added to 600 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in dichlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain Compound A5 (13.5 g, Yield: 68%).

calcd. C₄₇H₃₁N₃: C, 88.51; H, 4.90; N, 6.59. found: C, 88.39; H, 4.64; N, 6.43.

Synthesis Example 24
Synthesis of Compound A15

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10.00 g (31.04 mmol) of 3-bromo-N-phenylcarbazole, 10.99 g (31.04 mmol) of 2-triphenylene boronic ester, 150 mL of a mixture of tetrahydrofuran (THF) and toluene (1:1), and 75 mL of an aqueous solution of 2M potassium carbonate were mixed in a 500 mL round-bottom flask equipped with a stirrer in a nitrogen atmosphere, and 1.79 g (1.55 mmol) of tetrakis(triphenylphosphine)palladium(0) was added thereto, and heated under reflux in a nitrogen atmosphere for 12 hours. After completion of the reaction, the reaction product was added to methanol to obtain a solid by filtering. This solid was sufficiently washed with water and methanol, and then dried. The resulting product was dissolved in 400 mL of chlorobenzene by heating, followed by filtration using silica gel and removing the solvent. The resulting product was dissolved in 300 mL of toluene by heating, followed by recrystallization to obtain Compound A15 (8.74 g, Yield: 60%).

calcd. C₃₆H₂₃N: C, 92.08; H, 4.94; N, 2.98. found: C, 92.43; H, 4.63; N, 2.84.

Synthesis Example 25
Synthesis of Compound A17

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15.00 g (37.66 mmol) of 3-bromo-N-methbiphenylcarbazole, 16.77 g (37.66 mmol) of 3-boronic ester-N-biphenyl carbazole, 200 mL of a mixture of tetrahydrofuran (THF) and toluene (1:1), and 100 mL of an aqueous solution of 2M potassium carbonate were mixed in a 500 mL round-bottom flask equipped with a stirrer in a nitrogen atmosphere, and 2.18 g (1.88 mmol) of tetrakis(triphenylphosphine)palladium(0) was added thereto, and heated under reflux in a nitrogen atmosphere for 12 hours. After completion of the reaction, the reaction product was added to methanol to obtain a solid by filtering. This solid was sufficiently washed with water and methanol, and then dried. The resulting product was dissolved in 500 mL of chlorobenzene by heating, followed by filtration using silica gel and removing the solvent. The resulting product was dissolved in 400 mL of toluene by heating, followed by recrystallization to obtain Compound A17 (16.07 g, Yield: 67%).

calcd. C₄₈H3₂N2: C, 90.54; H, 5.07; N, 4.40. found: C, 90.71; H, 5.01; N, 4.27.

Synthesis Example 26
Synthesis of Compound A63

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6.3 g (15.4 mmol) of N-phenyl-3,3-bicarbazole, 5.0 g (15.4 mmol) of 4-(4-bromophenyl)dibenzo[b,d]furan, 3.0 g (30.7 mmol) of sodium t-butoxide, 0.9 g (1.5 mmol) of tris(dibenzylideneacetone)dipalladium, and 1.2 mL (50% in toluene) of tri t-butylphosphine were added to 100 mL of xylene in a 250 mL round-bottom flask, and heated under reflux in a nitrogen atmosphere for 15 hours. The resulting mixture was added to 300 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain the intermediate A63 (7.3 g, Yield: 73%).

calcd. C₄₈H₃₀N₂O: C, 88.59; H, 4.65; N, 4.30; O, 2.46. found: C, 88.56; H, 4.62; N, 4.20; O, 2.43.

Synthesis Example 27
Synthesis of Compound A64

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6.1 g (15.0 mmol) of N-phenyl-3,3-bicarbazole, 5.1 g (15.0 mmol) of 4-(4-bromophenyl)dibenzo[b,d]thiophene, 2.9 g (30.0 mmol) of sodium t-butoxide, 0.9 g (1.5 mmol) of tris(dibenzylideneacetone)dipalladium, and 1.2 mL (50% in toluene) of tri t-butylphosphine were added to 100 mL of xylene in a 250 mL round-bottom flask, and then heated under reflux in a nitrogen atmosphere for 15 hours. The resulting mixture was added to 300 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in monochlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain the intermediate A64 (6.7 g, Yield: 67%).

calcd. C48H30N2S: C, 86.46; H, 4.53; N, 4.20; S, 4.81. found: C, 86.41; H, 4.51; N, 4.18; S, 4.80.

Synthesis Example 28
Synthesis of Compound B2

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Synthesis of Intermediate B2

39.99 g (156.01 mmol) of indolocarbazole, 26.94 g (171.61 mmol) of tris(dibenzylideneacetone)dipalladium, and 2.9 mL of tri-t-butylphosphine (50% in toluene) were added to 500 mL of xylene in a 1000 mL round-bottom flask, and mixed and heated under reflux in a nitrogen atmosphere for 15 hours. The resulting mixture was added to 1000 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in dichlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain the intermediate B2 (23.01 g, Yield: 44%).

calcd. C₂₄H1₆N2: C, 86.72; H, 4.85; N, 8.43. found: C, 86.72; H, 4.85; N, 8.43.

Synthesis of Compound B2

22.93 g (69.03 mmol) of the intermediate B2, 11.38 g (72.49 mmol) of bromobenzene, 4.26 g (75.94 mmol) of potassium hydroxide, 13.14 g (69.03 mmol) of cupper iodide, and 6.22 g (34.52 mmol) of 1,10-phenanthroline were added to 230 mL of dimethylformamide (DMF) in a 500 mL round-bottom flask, and heated under reflux in a nitrogen atmosphere for 15 hours. The resulting mixture was added to 1000 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in dichlorobenzene and filtered using silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain Compound B2 (12.04 g, Yield: 43%).

calcd. C₃₀H₂₀N₂: C, 88.21; H, 4.93; N, 6.86. found: C, 88.21; H, 4.93; N, 6.86.

Manufacture of Organic Light-Emitting Device (Emission Layer Device 1-Single Host)
Example 1

A glass substrate with an ITO electrode was cut to a size of 50 mm×50 mm×0.5 mm, washed by sonication in acetone isopropyl alcohol and then in pure water each for 15 minutes, and washed with UV ozone for 30 minutes.

m-MTDATA was vacuum-deposited on the ITO electrode on the glass substrate at a deposition rate of 1 Å/sec to form an HIL having a thickness of 600 Å, and then α-NPB was vacuum-deposited on the HIL at a deposition rate of 1 Å/sec to form a HTL having a thickness of 300 Å. Subsequently, Ir(ppy)₃(dopant) and Compound a-2 (host) were co-deposited on the HTL at a deposition rate of 0.1 Å/sec and 1 Å/sec, respectively, to form an EML having a thickness of 400 Å. BAlq was vacuum-deposited on the EML at a deposition rate of 1 Å/sec to form an hole blocking layer (HBL) having a thickness of 50 Å, and then Alq₃was vacuum-deposited on the HBL to form a HTL having a thickness of 300 Å. LiF and A1 were sequentially vacuum-deposited on the ETL to form an EIL having a thickness of 10 Å and a cathode having a thickness of 2000 Å, respectively, thereby manufacturing 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 a-3, instead of Compound a-2, was used as a host to form the EML.

Example 3

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound a-6, instead of Compound a-2, was used as a host to form the EML.

Example 4

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound a-7, instead of Compound a-2, was used as a host to form the EML.

Example 5

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound a-19, instead of Compound a-2, was used as a host to form the EML.

Example 6

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound a-55, instead of Compound a-2, was used as a host to form the EML.

Example 7

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

Example 8

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound b-3, instead of Compound a-2, was used as a host to form the EML.

Example 9

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound b-6, instead of Compound a-2, was used as a host to form the EML.

Example 10

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound b-7, instead of Compound a-2, was used as a host to form the EML.

Example 11

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound b-19, instead of Compound a-2, was used as a host to form the EML.

Example 12

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound b-55, instead of Compound a-2, was used as a host to form the EML.

Example 13

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

Example 14

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound d-18, instead of Compound a-2, was used as a host to form the EML.

Example 15

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

Example 16

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound e-3, instead of Compound a-2, was used as a host to form the EML.

Example 17

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

Example 18

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound f-3, instead of Compound a-2, was used as a host to form the EML.

Comparative Example 1

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound A, instead of Compound a-2, was used as a host to form the EML. <Compound A>

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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 B, instead of Compound a-2, was used as a host to form the EML. <Compound B>

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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 C, instead of Compound a-2, was used as a host to form the EML. <Compound C>

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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 D, instead of Compound a-2, was used as a host to form the EML. <Compound D>

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Evaluation Example 1
Characteristics Evaluation of Organic Light-Emitting Devices (I)

Driving voltages, current efficiencies, and luminances of the organic light-emitting devices of Examples 1 to 4, 7, 8, 16 to 18 and Comparative Examples 1 to 4 were measured using a PR650 (Spectroscan) Source Measurement Unit (available from Photo Research, Inc.) while supplying power using a Kethley Source-Measure Unit (SMU 236). The results are shown in Table 2 below.

TABLE 2

Driving
Current

voltage
efficiency
Luminance

Examples
Host
Dopant
(V)
(cd/A)
(cd/m²)

Example 1
compound
a-2
Ir(ppy)3
4.3
42
6000

Example 2
compound
a-3
Ir(ppy)3
4.4
41
6000

Example 3
compound
a-6
Ir(ppy)3
4.6
39
6000

Example 4
compound
a-7
Ir(ppy)3
4.7
38
6000

Example 7
compound
b-2
Ir(ppy)3
4.4
40
6000

Example 8
compound
b-3
Ir(ppy)3
4.4
41
6000

Example 16
compound
e-3
Ir(ppy)3
4.5
39
6000

Example 17
compound
f-2
Ir(ppy)3
4.7
38
6000

Example 18
compound
f-3
Ir(ppy)3
4.4
39
6000

Comparative
compound
A
Ir(ppy)3
5.0
38
6000

Example 1

Comparative
compound
B
Ir(ppy)3
5.1
29
6000

Example 2

Comparative
compound
C
Ir(ppy)3
4.8
34
6000

Example 3

Comparative
compound
D
Ir(ppy)3
4.8
31
6000

Example 4

Referring to Table 2, the organic light-emitting devices of Examples 1 to 4, 7, 8, 16 to 18 were found to have lower driving voltages and higher current efficiencies, as compared to those of the organic light-emitting devices of Comparative Examples 1 to 4.

They have excellent charge transport characteristics as a phosphorescent host material, may overlap with the spectrum of a dopant well, improves performance such as efficiency increase and decrease of a driving voltage, and maximizes its performance as an OLED material.

Manufacture of Organic Light-Emitting Device (Emission Layer of Device-Mixed Host)
Example 19

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Ir(ppy)₃(dopant), Compound a-2 (first host), and Compound A1 (second host) were co-deposited in a weight ratio of 10:45:45 on the HTL to form the EML having a thickness of 400 Å.

Example 20

An organic light-emitting device was manufactured in the same manner as in Example 19, except that Compound A2, instead of Compound A1, was used to form the EML.

Example 21

An organic light-emitting device was manufactured in the same manner as in Example 19, except that Compound A5, instead of Compound A1, was used to form the EML.

Example 22

An organic light-emitting device was manufactured in the same manner as in Example 19, except that Compound A15, instead of Compound A1, was used to form the EML.

Example 23

An organic light-emitting device was manufactured in the same manner as in Example 19, except that Compound A17, instead of Compound A1, was used to form the EML.

Example 24

An organic light-emitting device was manufactured in the same manner as in Example 19, except that Compound B2, instead of Compound A1, was used to form the EML.

Example 25

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Ir(ppy)₃(dopant), Compound a-3 (first host), and Compound A17 (second host) were co-deposited in a weight ratio of 10:45:45 on the HTL to form the EML having a thickness of 400 Å.

Example 26

An organic light-emitting device was manufactured in the same manner as in Example 25, except that Compound b-2, instead of Compound a-3, was used to form the EML.

Example 27

An organic light-emitting device was manufactured in the same manner as in Example 25, except that Compound b-3, instead of Compound a-3, was used to form the EML.

Example 28

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Ir(ppy)₃(dopant), Compound a-2 (first host), and Compound A64 (second host) were co-deposited in a weight ratio of 10:45:45 on the HTL to form the EML having a thickness of 400 Å.

Example 29

An organic light-emitting device was manufactured in the same manner as in Example 28, except that Compound b-2, instead of Compound a-2, was used to form the EML.

Example 30

An organic light-emitting device was manufactured in the same manner as in Example 28, except that Compound e-2, instead of Compound a-2, was used to form the EML.

Example 31

An organic light-emitting device was manufactured in the same manner as in Example 28, except that Compound e-3, instead of Compound a-2, was used to form the EML.

Example 32

An organic light-emitting device was manufactured in the same manner as in Example 28, except that Compound f-2, instead of Compound a-2, was used to form the EML.

Example 33

An organic light-emitting device was manufactured in the same manner as in Example 28, except that Compound f-3, instead of Compound a-2, was used to form the EML.

Evaluation Example 2
Characteristics Evaluation of Organic Light-Emitting Devices (II)

Driving voltages, current efficiencies, luminances, and lifetimes of the organic light-emitting devices of Examples 19 to 33, and Comparative Examples 1 to 4 were measured using a PR650 (Spectroscan) Source Measurement Unit (available from Photo Research, Inc.) while supplying power using a Kethley Source-Measure Unit (SMU 236). The results are shown in Table 6 below. In Table 3, T₉₅indicates the time taken until an initial luminosity (assumed as 100%) is reduced to 95%.

TABLE 3

Driving
Current

T₉₅

Second

voltage
efficiency
Luminance
lifetime

Example
First host
host
Dopant
(V)
(cd/A)
(cd/m²)
(hr)

Example 19
Compound
Compound
Ir(ppy)₃
4.5
47
6000
71

a-2
A1

Example 20
Compound
Compound
Ir(ppy)₃
4.6
45
6000
73

a-2
A2

Example 21
Compound
Compound
Ir(ppy)₃
4.5
49
6000
75

a-2
A5

Example 22
Compound
Compound
Ir(ppy)₃
4.5
50
6000
76

a-2
A15

Example 23
Compound
Compound
Ir(ppy)₃
4.4
52
6000
80

a-2
A17

Example 24
Compound
Compound
Ir(ppy)₃
4.5
49
6000
73

a-2
B2

Example 25
Compound
Compound
Ir(ppy)₃
4.3
50
6000
78

a-3
A17

Example 26
Compound
Compound
Ir(ppy)₃
4.5
52
6000
79

b-2
A17

Example 27
Compound
Compound
Ir(ppy)₃
4.4
51
6000
78

b-3
A17

Example 28
Compound
Compound
Ir(ppy)₃
4.5
50
6000
79

a-2
A64

Example 29
Compound
Compound
Ir(ppy)₃
4.3
51
6000
82

b-2
A64

Example 30
Compound
Compound
Ir(ppy)₃
4.4
52
6000
77

e-2
A64

Example 31
Compound
Compound
Ir(ppy)₃
4.4
49
6000
76

e-3
A64

Example 32
Compound
Compound
Ir(ppy)₃
4.3
51
6000
83

f-2
A64

Example 33
Compound
Compound
Ir(ppy)₃
4.5
48
6000
79

f-3
A64

Comparative
Compound A
Ir(ppy)₃
5.0
38
6000
—

Example 1

Comparative
Compound B
Ir(ppy)₃
5.1
29
6000
—

Example 2

Comparative
Compound C
Ir(ppy)₃
4.8
34
6000
—

Example 3

Comparative
Compound D
Ir(ppy)₃
4.8
31
6000
—

Example 4

Referring to Table 3, the organic light-emitting devices of Examples 19 to 33 were found to have low driving voltages, high efficiencies, and long lifetimes.

Manufacture of Organic Light-Emitting Device (Emission Layer Device 2—Single Host)
Example 34

An organic light-emitting device was manufactured by using a-39 according to Synthesis Example 6 as a host and (piq)₂Ir(acac) as a dopant.

As for an anode, a 1000 Å-thick ITO was used, and as for a cathode, a 1000 Å-thick aluminum (Al) was used. Specifically, a method of manufacturing the organic light-emitting device used an anode obtained by cutting an ITO glass substrate having sheet resistance of 15 Ω/cm²into a size of 50 mm×50 mm×0.7 mm, ultrasonic wave-cleaning it with acetone, isopropyl alcohol and pure water for 15 minutes respectively and UV ozone-cleaning it for 30 minutes.

On the substrate, a 800 Å-thick hole transport layer (HTL) was formed by depositing N4,N4′-di(naphthalene-1-yl)-N4,N4′-diphenylbiphenyl-4,4′-diamine (NPB) (80 nm) with a vacuum degree of 650×10⁻⁷Pa at a deposition rate of 0.1 to 0.3 nm/s. Subsequently, a 300 Å-thick emission layer was formed thereon by using a-39 of Synthesis Example 6 under the same deposit condition, and herein, (piq)₂Ir(acac) as a phosphorescent dopant was simultaneously deposited therewith.

Herein, 3 wt % of the phosphorescent dopant based on 100 wt % of the emission layer was deposited by adjusting its deposition rate.

Then, a 50 Å-thick hole blocking layer was formed by using bis(2-methyl-8-quinolinolate)-4-(phenylphenolato)aluminium (BAlq) on the emission layer under the same vacuum deposition condition. Subsequently, a 200 Å-thick electron transport layer was formed thereon by depositing Alq3 under the same vacuum deposition condition. On the electron transport layer (ETL), a cathode was formed by sequentially depositing LiF and A1, manufacturing an organic optoelectronic device.

The organic optoelectronic device has a structure of ITO/NPB (80 nm)/EML (a-39 (97 wt %)+(piq)₂Ir(acac) (3 wt %), 30 nm)/Balq (5 nm)/Alq3 20 nm/LiF (1 nm)/Al 100 nm.

Example 35

An organic light-emitting device was manufactured according to the same method as Example 34 except for using the compound b-39 instead of the compound a-39.

Comparative Example 5

An organic light-emitting device was manufactured according to the same method as Example 34 except for using CBP having the following structure instead of the compound a-39 of Example 34.

NPB, BAlq, CBP and (piq)₂Ir(acac) used to manufacture the organic light-emitting device have a structure as follows.

embedded image

Evaluation Example 3
Characteristics of Organic Light-Emitting Device (III)

Current density, luminance and luminous efficiency depending on a voltage of the organic light-emitting devices according to Examples 34 to 35 and Comparative Example 5 were measured.

The specific measurements are described below, and the results are shown in Table 4.

(1) Measurement of Current Density Change Depending on Voltage Change

Current of each organic light-emitting device was measured by increasing a voltage from 0 V to 10 V by using a current-voltage meter (Keithley 2400), and the measured current value was divided by an area to provide the results.

(2) Measurement of Luminance Change Depending on Voltage Change

Luminance of each organic light-emitting device was measured by increasing a voltage from 0 V to 10 V by using a luminance meter (Minolta Cs-1000A).

(3) Measurement of Luminous Efficiency

The luminance and current density obtained from the above (1) and (2) and a voltage were used to calculate current efficiency (cd/A) at the same current density (10 mA/cm²).

(4) Life-Span

The life-span was obtained by measuring how long the current efficiency (cd/A) decreased by 90% while the luminance (cd/m²) was maintained at 5000 cd/m².

TABLE 4

90%

Driving

life-span

Emission
voltage
Color
Efficiency
(h) at

Nos.
layer
(V)
(EL color)
(cd/A)
5000 cd/m²

Comparative
CBP
6.4
red
6.0
25

Example 5

Example 34
a-39
5.8
red
10.1
50

Example 35
b-39
5.9
red
9.6
47

As shown in Table 4, the compounds according to the present invention showed improved driving voltage, luminous efficiency and/or power efficiency compared with Comparative Example 5.

Manufacture of Organic Light-Emitting Device (ETB Device)
Example 36

A glass substrate coated with a 1500 Å-thick ITO (Indium tin oxide) thin film was washed with distilled water/ultrasonic wave. The washed glass substrate was ultrasonic wave-washed with a solvent such as isopropyl alcohol, acetone, methanol and the like, dried, delivered to a plasma cleaner, cleaned by using an oxygen plasma therein, cleaned it for 10 minutes, and delivered to a vacuum depositor. This obtained ITO transparent electrode was used as an anode, and a 1400 Å-thick hole injection and transport layer was formed thereon by depositing HT13. Subsequently, on the hole transport layer (HTL), a 200 Å-thick emission layer was formed by doping BH113 and BD370 made by SFC Co. Ltd. as a blue florescent light-emitting host and dopant in an amount of 5 wt %. Then, on the emission layer, a 50 Å-thick electron transport auxiliary layer was formed by depositing the compound a-2 of Synthesis Example 1. On the electron transport auxiliary layer, a 310 Å-thick electron transport layer (ETL) was formed by vacuum-depositing tris(8-hydroxyquinoline) aluminum (Alq3), and a cathode was formed by sequentially vacuum-depositing 15 Å-thick Liq and 1200 Å-thick A1 on the electron transport layer (ETL), manufacturing an organic light-emitting device.

The organic light-emitting device had a five organic thin film-layered structure, specifically

ITO/HT13 1400 Å//EML[BH113:BD370=95:5 wt %]200 Å/compound a-2 50 Å/Alq3 310 Å/Liq 15 Å/Al 1200 Å.

Example 37

An organic light-emitting device was manufactured according to the same method as Example 36 except for using the compound a-3 of Synthesis Example 2 instead of the compound a-2 of Example 36.

Example 38

An organic light-emitting device was manufactured according to the same method as Example 36 except for using the compound b-2 of Synthesis Example 8 instead of the compound a-2 of Example 36.

Example 39

An organic light-emitting device was manufactured according to the same method as Example 36 except for using the compound b-3 of Synthesis Example 9 instead of the compound a-2 of Example 36.

Example 40

An organic light-emitting device was manufactured according to the same method as Example 36 except for using the compound e-2 of Synthesis Example 17 instead of the compound a-2 of Example 36.

Example 41

An organic light-emitting device was manufactured according to the same method as Example 36 except for using the compound e-3 of Synthesis Example 18 instead of the compound a-2 of Example 36.

Example 42

An organic light-emitting device was manufactured according to the same method as Example 36 except for using the compound f-2 of Synthesis Example 19 instead of the compound a-2 of Example 36.

Example 43

An organic light-emitting device was manufactured according to the same method as Example 36 except for using the compound f-3 of Synthesis Example 20 instead of the compound a-2 of Example 36.

Comparative Example 6

An organic light-emitting device was manufactured according to the same method as Example 36 except for using no electron transport auxiliary layer.

Evaluation Example 4
Characteristics (IV) of Organic Light-Emitting Device

Current density and luminance changes depending on a voltage, luminous efficiency of the organic light-emitting devices according to Examples 36 to 43, and Comparative Example 6 were measured, and the results are provided in the following Tables 8 and 9.

The specific measurements are described below, and the results are shown in Table 5.

(1) Measurement of Current Density Change Depending on Voltage Change

(2) Measurement of Luminance Change Depending on Voltage Change

Luminance of each organic light-emitting device was measured by increasing a voltage from 0 V to 10 V by using a luminance meter (Minolta Cs-1000A).

(3) Measurement of Luminous Efficiency

The luminance and current density obtained from the above (1) and (2) and a voltage were used to calculate current efficiency (cd/A) at the same current density (10 mA/cm²).

(5) Life-Span

T97 life-spans of the organic light-emitting devices of Examples 36 to 43 and Comparative Example 6 were measured as a time when their luminance decreased down to 97% relative to the initial luminance after emitting light with 750 cd/m²as the initial luminance (cd/m²) and measuring their luminance decrease depending on time with a Polanonix life-span measurement system.

TABLE 5

Electron

T97

transport

Color
life-span

auxiliary
Driving
Luminous
coordinate
(h) @

Device
layer
voltage
efficiency
(x, y)
750 nit

Example 36
compound
5.21
6.6
(0.133, 0.147)
123

a-2

Example 37
compound
5.25
6.7
(0.132, 0.148)
126

a-3

Example 38
compound
5.23
6.7
(0.132, 0.147)
124

b-2

Example 39
compound
5.01
6.8
(0.133, 0.147)
131

b-3

Example 40
compound
4.96
6.8
(0.133, 0.147)
128

e-2

Example 41
compound
4.93
6.6
(0.132, 0.148)
126

e-3

Example 42
compound
5.04
6.8
(0.132, 0.147)
129

f-2

Example 43
compound
5.02
6.7
(0.133, 0.147)
135

f-3

Comparative
Not used
5.02
6.8
(0.133, 0.147)
120

Example 6

Referring to Table 5, the organic light-emitting devices according to Examples 36 to 43 including the compounds of the present invention showed 1.13 times improved life-span compared with the organic light-emitting device according to Comparative Example 6. Accordingly, the electron transport auxiliary layer turned out to improve life-span characteristics of the organic light-emitting device.

While this invention has been described in connection with what is presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. Therefore, the aforementioned embodiments should be understood to be exemplary but not limiting the present invention in any way.

Number	Date	Country	Kind
10-2014-0003604	Jan 2014	KR	national
10-2014-0003605	Jan 2014	KR	national

CONDENSED CYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME

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