CONDENSED CYCLIC COMPOUND AND LIGHT-EMITTING DEVICE INCLUDING THE SAME

CROSS-REFERENCE TO RELATED APPLICATION

This application is based on and claims priority to and the benefit of Korean Patent Application No. 10-2020-0081669, filed on Jul. 2, 2020, in the Korean Intellectual Property Office, the entire content of which is hereby incorporated by reference.

BACKGROUND
1. Field

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

2. Description of Related Art

From among light-emitting devices, organic light-emitting devices (OLEDs) are self-emission devices that, as compared with other devices in the art, have wide viewing angles, high contrast ratios, short response times, and excellent characteristics in terms of luminance, driving voltage, and response speed, and produce full-color images.

OLEDs may include a first electrode on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, recombine in the emission layer to produce excitons. These excitons transition (e.g., relax) from an excited state to a ground state to thereby generate light.

SUMMARY

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

Additional aspects of embodiments 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 of the disclosure.

According to an aspect of an embodiment, there is provided a condensed cyclic compound represented by Formula 1:

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wherein, in Formula 1,

ring A₁to ring A₃may each independently be a C₅-C₃₀carbocyclic group or a C₂-C₃₀heterocyclic group,

R₁to R₅may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₁₀alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group,

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C₁-C₁₀alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl 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 isoxazolyl 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 quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl 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, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, and an azadibenzosilolyl group, each unsubstituted or substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C₁-C₁₀alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl 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 isoxazolyl 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 quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl 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, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, an azadibenzosilolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —P(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂), and

groups represented by Formulae A-1 and A-2,

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Q₁to Q₃and Q₃₁to Q₃₃are each independently selected from

—CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H, and —CD₂CDH₂, and

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, and a triazinyl group, each unsubstituted or substituted with at least one selected from deuterium, a C₁-C₁₀alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, and a triazinyl group,

at least one selected from R₁to R₃may not be hydrogen,

d1 to d3 may each independently be an integer from 1 to 20,

R₁and R₄may be optionally linked to each other to form a C₂-C₃₀heteromonocyclic group unsubstituted or substituted with at least one R_10a,

R₂and R₅may be optionally linked to each other to form a C₂-C₃₀heteromonocyclic group unsubstituted or substituted with at least one R_20a,

R_10aand R_20amay be the same as described in connection with R₁, and R_10aand R_20amay not form a cyclic group with a neighboring substituent,

wherein, in Formulae A-1 and A-2,

R₁₀may be the same as described in connection with R_10a,

d10 may be an integer from 1 to 13, and

* indicates a binding site to a neighboring atom.

According to one or more embodiments, a light-emitting device may include a first electrode, a second electrode facing the first electrode, an interlayer between the first electrode and the second electrode and including an emission layer, and at least one of the condensed cyclic compound represented by Formula 1.

BRIEF DESCRIPTION OF THE DRAWINGS

The above and other aspects and features of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, in which:

FIG. 1 is a schematic cross-sectional view of an embodiment of a light-emitting device; FIG. 2 is a schematic cross-sectional view of an embodiment of a light-emitting device; and FIG. 3 is a schematic cross-sectional view of an embodiment of a light-emitting device.

DETAILED DESCRIPTION

Reference will now be made in more detail to embodiments of the present disclosure, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to 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 embodiments 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. Throughout the disclosure, the expression “at least one of a, b or c” indicates only a, only b, only c, both a and b, both a and c, both b and c, all of a, b, and c, or variations thereof.

A condensed cyclic compound according to the present disclosure may be represented by Formula 1:

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wherein, in Formula 1,

ring A₁to ring A₃may each independently be a C₅-C₃₀carbocyclic group or a C₂-C₃₀heterocyclic group.

In an embodiment, ring A₁to ring A₃may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.

In one or more embodiments, ring A₁to ring A₃may each independently be a benzene group, a naphthalene group, a carbazole group, a fluorene group, a dibenzothiophene group, or a dibenzofuran group.

R₁to R₅may each independently be selected from: hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, and a C₁-C₂₀alkoxy group;

—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂); and

groups represented by Formulae A-1 and A-2,

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wherein Q₁to Q₃and Q₃₁to Q₃₃are each independently selected from:

—CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H, and —CD₂CDH₂; and

wherein, in Formulae A-1 and A-2,

R₁₀is the same as described in connection with R_10a,

d10 may be an integer from 1 to 13, and

* indicates a binding site to a neighboring atom.

In an embodiment, R₁to R₅may each independently be selected from:

hydrogen, deuterium, a C₁-C₂₀alkyl group, and a C₁-C₂₀alkoxy group;

a C₁-C₂₀alkyl group and a C₁-C₂₀alkoxy group, each substituted with at least one selected from deuterium, —CD₃, —CD₂H, —CDH₂, C₁-C₁₀alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, and a naphthyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C₁-C₁₀alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group, each unsubstituted or substituted with at least one selected from deuterium, —CD₃, —CD₂H, —CDH₂, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C₁-C₁₀alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), and —B(Q₃₁)(Q₃₂);

—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), and —B(Q₁)(Q₂); and

groups represented by Formulae A-1 and A-2,

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wherein Q₁to Q₃and Q₃₁to Q₃₃are each independently selected from:

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, unsubstituted or substituted with at least one selected from deuterium, a C₁-C₁₀alkyl group, a phenyl group, and a biphenyl group.

Formulae A-1 and A-2 are the same as described above.

In an embodiment, R₄and R₅may each independently be selected from:

hydrogen, deuterium, and a C₁-C₂₀alkyl group;

a C₁-C₂₀alkyl group, substituted with at least one selected from deuterium, —CD₃, —CD₂H, —CDH₂, C₁-C₁₀alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group, each unsubstituted or substituted with at least one selected from deuterium, —CD₃, —CD₂H, —CDH₂, C₁-C₂₀alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃) and —N(Q₃₁)(Q₃₂), and —B(Q₃₁)(Q₃₂); and

groups represented by Formulae A-1 and A-2,

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wherein Q₁to Q₃and Q₃₁to Q₃₃are each independently selected from:

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, unsubstituted or substituted with at least one selected from deuterium, a C₁-C₁₀alkyl group, a phenyl group, and a biphenyl group.

Formulae A-1 and A-2 are the same as described above.

In an embodiment, each of R₁to R₃may not be hydrogen.

In an embodiment, R₁and R₂may be identical to each other.

In an embodiment, d1 to d3 may each independently be an integer from 1 to 20.

In an embodiment, d1 to d3 may be 1 or 2.

R₁and R₄may be optionally linked to each other to form a C₂-C₃₀heteromonocyclic group unsubstituted or substituted with at least one R_10a,

R₂and R₅may be optionally linked to each other to form a C₂-C₃₀heteromonocyclic group unsubstituted or substituted with at least one R_20a,

R_10aand R_20amay be the same as described in connection with R₁, and R_10aand R_20amay not form a cyclic group with a neighboring substituent.

In an embodiment, the condensed cyclic compound represented by Formula 1 may satisfy at least one selected from Condition 1 and Condition 2:

Condition 1

R₁and R₄are linked to each other to form a C₂-C₃₀heteromonocyclic group unsubstituted or substituted with at least one R_10a.

Condition 2

R₂and R₅are linked to each other to form a C₂-C₃₀heteromonocyclic group unsubstituted or substituted with at least one R_20a.

R_10aand R_20aare the same as described above.

In some embodiments,

R₁and R₄are linked to each other to form a C₂-C₃₀heteromonocyclic group unsubstituted or substituted with at least one R_20a,

R₂and R₅are linked to each other to form a C₂-C₃₀heteromonocyclic group unsubstituted or substituted with at least one R_20a, and

R_10aand R_20aare the same as described above.

In an embodiment, the condensed cyclic compound may be represented by Formula 1-1 to 1-12:

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Regarding Formulae 1-1 to 1-12, R₄and R₅are the same as described in above, and R₁₁to R₁₃may be the same as described in connection with R₁, R₂₁to R₂₃may be the same as described in connection with R₂, and R₃₁to R₃₃may be the same as described in connection with R₃.

In an embodiment, the condensed cyclic compound may be represented by Formula 2-1 or 2-2:

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wherein, in Formulae 2-1 and 2-2,

X₁may be *—(CR_1aR_1b)_m1—*′,

X₂may be *—(CR_2aR_2b)_m2—*′,

m1 and m2 may each independently be an integer from 1 to 10,

m1 indicates the number of —(CR_1aR_1b)—,

when m1 is 2 or more, each —(CR_1aR_1b)— may be identical to or different from each other,

m2 indicates the number of —(CR_2aR_2b)—,

when m2 is 2 or more, each —(CR_2aR_2b)— may be identical to or different from each other, and

* and *′ each indicate a binding site to a neighboring atom.

A₁to A₃, R₁to R₃, R₅and d1 to d3 are the same as described in above, R_1a, R_2a, R_1b, and R_2bare the same as described in connection with R_10a, and each of R_1a, R_2a, R_1b, and R_2bmay not form a cyclic group with a neighboring substituent.

In an embodiment, m1 may be 1, and m2 may be 1;

m1 may be 1, and m2 may be 2;

m1 may be 1, and m2 may be 3;

m1 may be 1, and m2 may be 4;

m1 may be 2, and m2 may be 2;

m1 may be 2, and m2 may be 3;

m1 may be 2, and m2 may be 4;

m1 may be 3, and m2 may be 3;

m1 may be 3, and m2 may be 4; or

m1 may be 4, and m2 may be 4.

In an embodiment, m1 and m2 may each independently be an integer from 1 to 4.

In an embodiment, m1 may be 2, and m2 may be 2;

m1 may be 2, and m2 may be 3;

m1 may be 2, and m2 may be 4;

m1 may be 3, and m2 may be 3;

m1 may be 3, and m2 may be 4; or

m1 may be 4, and m2 may be 4.

In an embodiment, m1 and m2 may be identical to each other.

In an embodiment, R_1a, R_2a, R_1b, and R_2bmay each be hydrogen or deuterium.

In an embodiment, the condensed cyclic compound may be represented by Formula 3-1 to 3-12:

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Regarding Formulae 3-1 to 3-12, X₁, X₂and R₅are the same as described in above, R₁₁to R₁₃may be the same as descried in connection with R₁, R₂₁to R₂₃may be the same as described with R₂, and R₃₁to R₃₃may be the same as described in connection with R₃.

In an embodiment, the condensed cyclic compound may be selected from Compounds 1 to 114, but embodiments of the present disclosure are not limited thereto:

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The condensed cyclic compound represented by Formula 1 has a broad plate-like structure containing a boron atom, and an amine substituted with an alkyl group or a carbocyclic group.

Formula 1 has a plate-like skeleton containing two nitrogen atoms and a boron atom. Due to the plate-like structure of the condensed cyclic compound represented by Formula 1 having a condensed cyclic group, in that compound multiple resonances are further activated, the delocalization of electrons in the intramolecular structure is expanded, and the polarizability is increased, and thus, the f value is further increased. Accordingly, the condensed cyclic compound of Formula 1 may be used as a light-emitting material for high-efficiency delayed fluorescence.

In addition, because Formula 1 includes an amine substituted with an alkyl group or a carbocyclic group, which enhances the electron donating ability, multiple resonances are more activated, resulting in a higher f-value and a lower ΔE_ST.

The substituent of the amine is fused in a cyclic form to the backbone. Accordingly, compared to a substituent that is not condensed, the number of the C—N bonds that freely rotate is reduced, and thus, in the view of a bond dissociation energy (BDE), a molecule (the condensed cyclic compound represented by Formula 1) may become more rigid, and the chemical instability caused by the presence of the electron deficient boron atom may be compensated for by the electron rich amine. In addition, due to the rigid molecular model of the condensed cyclic compound represented by Formula 1, the light extraction efficiency using a transition dipole moment may be increased.

Therefore, an electronic device, e.g., an organic light-emitting device, using the condensed cyclic compound represented by Formula 1 may have a low driving voltage, high maximum quantum efficiency, high efficiency, and a long lifespan.

Synthesis methods of the condensed cyclic compound represented by Formula 1 may be recognizable by one of ordinary skill in the art by referring to Examples provided below.

In an embodiment, provided is a light-emitting device including: a first electrode; a second electrode facing the first electrode; and an interlayer, which is between the first electrode and the second electrode and includes an emission layer, wherein the interlayer includes at least one condensed cyclic compound represented by Formula 1 as described in this specification.

In an embodiment, provided is a light-emitting device including: a first electrode; a second electrode facing the first electrode; and an interlayer which is between the first electrode and the second electrode and includes an emission layer, wherein the interlayer further includes a hole transport region between the first electrode and the emission layer, and the hole transport region includes a compound represented by Formula 201, a compound represented by Formula 202, or a combination thereof, and the emission layer includes at least one condensed cyclic compound represented by Formula 1.

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wherein, in Formulae 201 and 202,

L₂₀₁to L₂₀₄may each independently be a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10bor a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10b,

L₂₀₅may be *—O—*′, *—S—*′, *—N(Q₂₀₁)-*′, a C₁-C₂₀alkylene group unsubstituted or substituted with at least one R_10b, a C₂-C₂₀alkenylene group unsubstituted or substituted with at least one R_10b, a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10b, or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10b,

xa1 to xa4 may each independently be an integer from 0 to 5,

xa5 may be an integer from 1 to 10,

R₂₀₁to R₂₀₄and Q₂₀₁may each independently be a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10bor a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10b,

R₂₀₁and R₂₀₂may optionally be linked to each other, via a single bond, a C₁-C₅alkylene group unsubstituted or substituted with at least one R_10b, or a C₂-C₅alkenylene group unsubstituted or substituted with at least one R_10b, to form a C₈-C₆₀polycyclic group unsubstituted or substituted with at least one R_10b,

R₂₀₃and R₂₀₄may optionally be linked to each other, via a single bond, a C₁-C₅alkylene group unsubstituted or substituted with at least one R_10b, or a C₂-C₅alkenylene group unsubstituted or substituted with at least one R_10b, to form a C₈-C₆₀polycyclic group unsubstituted or substituted with at least one R_10b, and

na1 may be an integer from 1 to 4.

R_10bmay be:

deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;

a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, or a C₁-C₆₀alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₃-C₆₀carbocyclic group, a C₁-C₆₀heterocyclic group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), —P(═O)(Q₁₁)(Q₁₂), or any combination thereof;

a C₃-C₆₀carbocyclic group, a C₁-C₆₀heterocyclic group, a C₆-C₆₀aryloxy group, or a C₆-C₆₀arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₆-C₆₀carbocyclic group, a C₁-C₆₀heterocyclic group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), —P(═O)(Q₂₁)(Q₂₂), or any combination thereof; or

—Si(Q_31b)(Q_32b)(Q_33b), —N(Q_31b)(Q_32b), —B(Q_31b)(Q_32b), —C(═O)(Q_31b), —S(═O)₂(Q_31b), or —P(═O)(Q_31b)(Q_32b),

wherein Q₁₁to Q₁₃, Q₂₁to Q₂₃, and Q_31bto Q_33b, as used herein, may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C₁-C₆₀alkyl group; a C₂-C₆₀alkenyl group; a C₂-C₆₀alkynyl group; a C₁-C₆₀alkoxy group; or a C₃-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, a C₁-C₆₀alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.

In one or more embodiments,

the first electrode of the light-emitting device may be an anode,

the second electrode of the light-emitting device may be a cathode,

the interlayer may further include an electron transport region between the emission layer and the second electrode, and

the hole transport region includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and

the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

In one or more embodiments, the emission layer in the interlayer of the light-emitting device may include a dopant and a host, and the condensed cyclic compound may be included in the dopant. For example, the condensed cyclic compound may act as a dopant.

The emission layer may emit red light, green light, blue light, and/or white light. In an embodiment, the emission layer may emit blue light or cyan light. The blue light or cyan light may have, for example, a maximum luminescence wavelength in a range of about 400 nm to about 500 nm.

The condensed cyclic compound included in the emission layer acts as a delayed fluorescence dopant, so that delayed fluorescence may be emitted from the emission layer.

In an embodiment, the organic layer may contain an anthracene compound.

The anthracene compound refers to a compound including an anthracene ring, and the organic layer may include a compound including an anthracene ring.

In one or more embodiments, the light-emitting device may further include:

a first capping layer, located outside the first electrode;

a second capping layer, located outside the second electrode; or

the first capping layer and the second capping layer.

According to another aspect of an embodiment, provided is a light-emitting device including: a first electrode; a second electrode facing the first electrode; an interlayer which is between the first electrode and the second electrode and includes the emission layer; and

a second capping layer, which is located outside the second electrode and has a refractive index of 1.6 or more, and the emission layer, includes at least one condensed cyclic compound represented by Formula 1.

In an embodiment, an encapsulation portion may be on the second capping layer. The encapsulation portion may be on a light-emitting device to protect the light-emitting device from moisture and/or oxygen.

In an embodiment, the encapsulation portion may include an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof;

an organic film including polyethyleneterephthalate, polyethylenenaphthalate, polycarbonate, polyimide, polyethylenesulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (for example, polymethylmethacrylate, polyacrylic acid, etc.), an epoxy-based resin (for example, an aliphatic glycidyl ether (AGE), etc.), or any combination thereof; or

a combination of the inorganic film and the organic film.

The expression “(an interlayer) includes a condensed cyclic compound,” as used herein, may include a case in which “(an interlayer) includes identical condensed cyclic compounds represented by Formula 1” and a case in which “(an interlayer) includes two or more different condensed cyclic compounds represented by Formula 1.”

For example, the interlayer may include, as the condensed cyclic compound, only Compound 1. In this embodiment, Compound 1 may be included in the emission layer of the light-emitting device. In one or more embodiments, the interlayer may include, as the condensed cyclic compound, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may exist in an identical layer (for example, Compound 1 and Compound 2 may all exist in an emission layer), or different layers (for example, Compound 1 may exist in an emission layer and Compound 2 may exist in an electron transport region).

The term “interlayer,” as used herein, refers to a single layer and/or all of a plurality of layers between a first electrode and a second electrode of a light-emitting device.

According to another aspect of an embodiment, an electronic apparatus including the light-emitting device is provided. The electronic apparatus may further include a thin-film transistor.

In one or more embodiments, the electronic apparatus may further include a thin-film transistor including a source electrode and a drain electrode, and the first electrode of the light-emitting device may be electrically coupled to the source electrode or the drain electrode.

In an embodiment, the electronic apparatus may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. For example, the electronic apparatus may be a flat panel display apparatus, but embodiments of the present disclosure are not limited thereto.

Other details of the electronic apparatus are the same as described elsewhere in the present specification

Description of FIG. 1

FIG. 1 is a schematic cross-sectional view of a light-emitting device 10 according to an embodiment. The light-emitting device 10 includes a first electrode 110, an interlayer 130, and a second electrode 150.

Hereinafter, the structure of the light-emitting device 10 according to an embodiment and a method of manufacturing the light-emitting device 10 will be described in connection with FIG. 1.

First Electrode 110

In FIG. 1, a substrate may be additionally under the first electrode 110 or above the second electrode 150. The substrate may be a glass substrate and/or a plastic substrate. The substrate may be a flexible substrate. In one or more embodiments, the substrate may include plastics (e.g., polymers) having excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or a combination thereof.

The first electrode 110 may be formed by, for example, depositing and/or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a high work function material that can easily inject holes may be used as a material for a first electrode.

The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), or any combinations thereof. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combinations thereof may be used as a material for forming a first electrode.

The first electrode 110 may have a single-layered structure including (e.g., consisting of) a single layer or a multi-layered structure including a plurality of layers. In an embodiment, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO.

Interlayer 130

The interlayer 130 is on the first electrode 110. The interlayer 130 includes an emission layer.

The interlayer 130 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 150.

The interlayer 130 may further include metal-containing compounds such as organometallic compounds, inorganic materials such as quantum dots, and/or the like, in addition to various suitable organic materials.

In one or more embodiments, the interlayer 130 may include, i) two or more emitting units sequentially stacked between the first electrode 110 and the second electrode 150 and ii) a charge generation layer between the two emitting units. When the interlayer 130 includes the emitting unit and the charge generation layer as described above, the light-emitting device 10 may be a tandem light-emitting device.

Hole Transport Region in Interlayer 130

The hole transport region may have: i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.

The hole transport region may include a hole injection layer (HIL), a hole transport layer (HTL), an emission auxiliary layer, an electron blocking layer (EBL), or any combination thereof.

For example, the hole transport region may have a multi-layered structure including a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein, in each structure, layers are stacked sequentially from the first electrode 110.

The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:

embedded image

wherein, in Formulae 201 and 202,

L₂₀₁to L₂₀₄may each independently be a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a,

L₂₀₅may be *—O—*′, *—S—*′, *—N(Q₂₀₁)-*′, a C₁-C₂₀alkylene group unsubstituted or substituted with at least one R_10a, a C₂-C₂₀alkenylene group unsubstituted or substituted with at least one R_10a, a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10a, or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a,

xa1 to xa4 may each independently be an integer from 0 to 5,

xa5 may be an integer from 1 to 10, and

R₂₀₁to R₂₀₄and Q₂₀₁may each independently be a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a,

R₂₀₁and R₂₀₂may optionally be linked to each other, via a single bond, a C₁-C₅alkylene group unsubstituted or substituted with at least one R_10a, or a C₂-C₅alkenylene group unsubstituted or substituted with at least one R_10a, to form a C₈-C₆₀polycyclic group unsubstituted or substituted with at least one R_10a(for example, a carbazole group or the like) (for example, refer to the following compound HT16),

R₂₀₃and R₂₀₄may optionally be linked to each other, via a single bond, a C₁-C₅alkylene group unsubstituted or substituted with at least one R_10a, or a C₂-C₅alkenylene group unsubstituted or substituted with at least one R_10a, to form a C₈-C₆₀polycyclic group unsubstituted or substituted with at least one R_10a, and

na1 may be an integer from 1 to 4.

In an embodiment, Formulae 201 and 202 may each include at least one selected from the groups represented by Formulae CY201 to CY217:

embedded image

Regarding Formulae CY201 to CY217, R_10band R_10care the same as described in connection with R_10a, ring CY₂₀₁to ring CY₂₀₄may each independently be a C₃-C₂₀carbocyclic group or a C₁-C₂₀heterocyclic group, and at least one hydrogen in Formula CY201 to CY217 may be unsubstituted or substituted with at least one R_10adescribed herein.

In an embodiment, ring CY₂₀₁to ring CY₂₀₄in Formulae CY201 to CY217 may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.

In an embodiment, Formulae 201 and 202 may each include at least one selected from the groups represented by Formulae CY201 to CY203:

In one or more embodiments, Formula 201 may include at least one selected from the groups represented by Formulae CY201 to CY203 and at least one selected from the groups represented by Formulae CY204 to CY217.

In one or more embodiments, in Formula 201, xa1 is 1, R₂₀₁is a group represented by one selected from Formulae CY201 to CY203, xa2 is 0, R₂₀₂is a group represented by one selected from Formulae CY204 to CY207.

In one or more embodiments, each of Formulae 201 and 202 may not include a group represented by one selected from Formulae CY201 to CY203.

In one or more embodiments, each of Formulae 201 and 202 may not include a group represented by one selected from Formulae CY201 to CY203 and may include at least one selected from the groups represented by Formulae CY204 to CY217.

In an embodiment, each of Formulae 201 and 202 may not include a group represented by any one of Formulae CY201 to CY217.

In an embodiment, the hole transport region may include one selected from Compounds HT1 to HT44, m-MTDATA, TDATA, 2-TNATA, NPB(NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), or any combination thereof:

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A thickness of the hole transport region may be in a range of about 50 Å to about 10,000 Å, for example, about 100 Å to about 4,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer and the hole transport layer are within any of the foregoing ranges, suitable or satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.

The emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by an emission layer, and the electron blocking layer may block or reduce the flow of electrons from an electron transport region. The emission auxiliary layer and the electron blocking layer may include the materials as described above.

P-Dopant

The hole transport region may further include, in addition to these materials, a charge-generating material for the improvement of conductive properties (e.g., electrically conductive properties). The charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region (for example, in the form of a single layer of a charge-generating material).

The charge-generation material may be, for example, a p-dopant.

In an embodiment, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be −3.5 eV or less.

In an embodiment, the p-dopant may include a quinone derivative, a cyano group-containing compound, element EL1, and element EL2-containing compound, or any combination thereof.

Examples of the quinone derivative are TCNQ and F4-TCNQ.

Examples of the cyano group-containing compound are HAT-CN and a compound represented by Formula 221 below.

embedded image

wherein, in Formula 221,

R₂₂₁to R₂₂₃may each independently be a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a, and

at least one selected from R₂₂₁to R₂₂₃may each independently be a C₃-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group, each substituted with: a cyano group; —F; —Cl; —Br; —I; a C₁-C₂₀alkyl group substituted with a cyano group, —F, —Cl, —Br, —I, or any combination thereof; or any combination thereof.

Regarding the element EL1 and element EL2-containing compound, element EL1 may be a metal, a metalloid, or a combination thereof, and element EL2 may be a non-metal, a metalloid, or a combination thereof.

Examples of the metal include: an alkali metal (for example, lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), and/or the like); alkaline earth metal (for example, beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), and/or the like); transition metal (for example, titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper(Cu), silver (Ag), gold (Au), and/or the like); post-transition metals (for example, zinc (Zn), indium (In), tin (Sn), and/or the like); and lanthanide metal (for example, lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), ruthenium (Lu), and/or the like).

Examples of the metalloid include silicon (Si), antimony (Sb), and tellurium (Te).

Examples of the non-metal include oxygen (O) and halogen (for example, F, Cl, Br, I, etc.).

In an embodiment, examples of element EL1 and element EL2-containing compound include a metal oxide, a metal halide (for example, metal fluoride, metal chloride, metal bromide, and/or metal iodide), a metalloid halide (for example, metalloid fluoride, metalloid chloride, metalloid bromide, and/or metalloid iodide), metal telluride, and any combination thereof.

Examples of the metal oxide include tungsten oxide (for example, WO, W₂O₃, WO₂, WO₃, and/or W₂O₅), vanadium oxide (for example, VO, V₂O₃, VO₂, and/or V₂O₅), molybdenum oxide (MoO, Mo₂O₃, MoO₂, MoO₃, and/or Mo₂O₅), and rhenium oxide (for example, ReO₃).

Examples of the metal halide include alkali metal halide, alkaline earth metal halide, transition metal halide, post-transition metal halide, and lanthanide metal halide.

Examples of the alkali metal halide include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI.

Examples of the alkaline earth metal halide include BeF₂, MgF₂, CaF₂, SrF₂, BaF₂, BeCl₂, MgCl₂, CaCl₂, SrCl₂, BaCl₂, BeBr₂, MgBr₂, CaBr₂, SrBr₂, BaBr₂, BeI₂, MgI₂, CaI₂, SrI₂, and BaI₂.

Examples of the transition metal halide include titanium halide (for example, TiF₄, TiCl₄, TiBr₄, and/or TiI₄), zirconium halide (for example, ZrF₄, ZrCl₄, ZrBr₄, and/or ZrI₄), hafnium halide (for example, HfF₄, HfCl₄, HfBr₄, and/or HfI₄), vanadium halide (for example, VF₃, VCl₃, VBr₃, and/or VI₃), niobium halide (for example, NbF₃, NbCl₃, NbBr₃, and/or NbI₃), tantalum halide (for example, TaF₃, TaCl₃, TaBr₃, and/or TaI₃), chromium halide (for example, CrF₃, CrCl₃, CrBr₃, and/or CrI₃), molybdenum halide (for example, MoF₃, MoCl₃, MoBr₃, and/or MoI₃), tungsten halide (for example, WF₃, WCl₃, WBr₃, and/or WI₃), manganese halide (for example, MnF₂, MnCl₂, MnBr₂, and/or MnI₂), technetium halide (for example, TcF₂, TcCl₂, TcBr₂, and/or TcI₂), rhenium halide (for example, ReF₂, ReCl₂, ReBr₂, and/or ReI₂), iron halide (for example, FeF₂, FeCl₂, FeBr₂, and/or FeI₂), ruthenium halide (for example, RuF₂, RuCl₂, RuBr₂, and/or RuI₂), osmium halide (for example, OsF₂, OsCl₂, OsBr₂, and/or OsI₂), cobalt halide (for example, CoF₂, CoCl₂, CoBr₂, and/or CoI₂), rhodium halide (for example, RhF₂, RhC₂, RhBr₂, and/or RhI₂), iridium halide (for example, IrF₂, IrCl₂, IrBr₂, and/or IrI₂), nickel halide (for example, NiF₂, NiCl₂, NiBr₂, and/or NiI₂), palladium halide (for example, PdF₂, PdCl₂, PdBr₂, and/or PdI₂), platinum halide (for example, PtF₂, PtCl₂, PtBr₂, and/or PtI₂), copper halide (for example, CuF, CuCl, CuBr, and/or CuI), silver halide (for example, AgF, AgCl, AgBr, and/or AgI), and gold halide (for example, AuF, AuCl, AuBr, and/or AuI).

Examples of the post-transition metal halide include zinc halide (for example, ZnF₂, ZnCl₂, ZnBr₂, and/or ZnI₂), indium halide (for example, InI₃), and tin halide (for example, SnI₂).

Examples of the lanthanide metal halide include YbF, YbF₂, YbF₃, SmF₃, YbCl, YbCl₂, YbCl₃SmCl₃, YbBr, YbBr₂, YbBra SmBr₃, YbI, YbI₂, YbI₃, and Smi₃.

Examples of the metalloid halide include antimony halide (for example, SbCl₅).

Examples of the metal telluride include an alkali metal telluride (for example, Li₂Te, Na₂Te, K₂Te, Rb₂Te, and/or Cs₂Te), alkaline earth metal telluride (for example, BeTe, MgTe, CaTe, SrTe, and/or BaTe), transition metal telluride (for example, TiTe₂, ZrTe₂, HfTe₂, V₂Te₃, Nb₂Te₃, Ta₂Te₃, Cr₂Te₃, Mo₂Te₃, W₂Te₃, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu₂Te, CuTe, Ag₂Te, AgTe, and/or Au₂Te), post-transition metal telluride (for example, ZnTe), and lanthanide metal telluride (for example, LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, and/or LuTe).

Emission Layer in Interlayer 130

When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers of a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers contact each other or are separated from each other. In one or more embodiments, the emission layer may include two or more materials of a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed with each other in a single layer to emit white light.

The emission layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.

The dopant may include the condensed cyclic compound represented by Formula 1.

The amount of the dopant in the emission layer may be in a range from about 0.01 to about 15 parts by weight based on 100 parts by weight of the host.

In one or more embodiments, the emission layer may include a quantum dot.

In some embodiments, the emission layer may include a delayed fluorescent material. The delayed fluorescent material may act as a host or a dopant in the emission layer.

A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within any of the foregoing ranges, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.

Host

In one or more embodiments, the host may include a compound represented by Formula 301 below:

[Ar₃₀₁]_xb11-[(L₃₀₁)_xb1-R₃₀₁]_xb21 Formula 301

wherein, in Formula 301,

Ar₃₀₁and L₃₀₁may each independently be a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a,

xb11 may be 1, 2, or 3,

xb1 may be an integer from 0 to 5,

R₃₀₁may be hydrogen, deuterium, —F, —Cl, —Br, —I, hydroxyl group, cyano group, a nitro group, a C₁-C₆₀alkyl group unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkenyl group unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkynyl group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀alkoxy group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a, —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), —N(Q₃₀₁)(Q₃₀₂), —B(Q₃₀₁)(Q₃₀₂), —C(═O)(Q₃₀₁), —S(═O)₂(Q₃₀₁), or —P(═O)(Q₃₀₁)(Q₃₀₂),

xb21 may be an integer from 1 to 5,

Q₃₀₁to Q₃₀₃are the same as described in connection with Q₁.

In one or more embodiments, when xb11 in Formula 301 is 2 or more, two or more of Ar₃₀₁(s) may be linked to each other via a single bond.

In an embodiment, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination embodiment:

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wherein, in Formulae 301-1 and 301-2,

ring A₃₀₁to ring A₃₀₄may each independently be a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a,

X₃₀₁may be O, S, N-[(L₃₀₄)_xb4-R₃₀₄], C(R₃₀₄)(R₃₀₅), or Si(R₃₀₄)(R₃₀₅),

xb22 and xb23 are each independently 0, 1, or 2,

L₃₀₁, xb1, and R₃₀₁are the same as described above,

L₃₀₂to L₃₀₄are each independently the same as described in connection with L₃₀₁,

xb2 to xb4 may each independently be the same as described in connection with xb1, and

R₃₀₂to R₃₀₅and R₃₁₁to R₃₁₄are the same as described in connection with R₃₀₁.

In one or more embodiments, the host may include an alkaline earth metal complex. In an embodiment, the host may be a Be complex (for example, Compound H55), a Mg complex, a Zn complex, or any combination thereof.

In an embodiment, the host may include at least one selected from Compounds H1 to H124, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), or any combination thereof, but embodiments of the present disclosure are not limited thereto:

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Delayed Fluorescent Material

The emission layer may include a delayed fluorescent material.

The delayed fluorescent material used herein may be selected from any suitable compound that is capable of emitting delayed fluorescent light based on a delayed fluorescence emission mechanism.

The delayed fluorescent material included in the emission layer may act as a host or a dopant depending on the type (or composition) of other materials included in the emission layer.

In an embodiment, the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material may be 0 eV or more and 0.5 eV or less. When the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material satisfies the above-described range, up-conversion from the triplet state to the singlet state of the delayed fluorescent materials may suitably or effectively occur, and thus, the luminescence efficiency of the light-emitting device 10 may be improved.

In an embodiment, the delayed fluorescent material may include i) a material that includes at least one electron donor (for example, a π electron-rich C₃-C₆₀cyclic group, such as a carbazole group) and at least one electron acceptor (for example, a sulfoxide group, a cyano group, or a π electron-deficient nitrogen-containing C₁-C₆₀cyclic group), ii) a material including a C₈-C₆₀polycyclic group in which two or more cyclic groups share boron (B) and are condensed with each other (e.g., combined together with each other).

The delayed fluorescent material may include at least one selected from compounds DF1 to DF9:

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Quantum Dot

The emission layer may include a quantum dot.

The quantum dot used herein refers to the crystal of a semiconductor compound, and may include any suitable material that is capable of emitting light of various suitable emission wavelengths depending on the size of the crystal.

A diameter of the quantum dot may be, for example, in a range of about 1 nm to about 10 nm.

The quantum dot may be synthesized by a wet chemical process, an organometallic chemical vapor deposition process, a molecular beam epitaxy process, or a process that is similar to these processes.

The wet chemical process refers to a method in which an organic solvent and a precursor material are mixed, and then, a quantum dot particle crystal is grown. When the crystal grows, the organic solvent acts as a dispersant naturally coordinated on the surface of the quantum dot crystal and controls the growth of the crystal. Accordingly, by using a process that is easily performed at low costs compared to a vapor deposition process, such as a metal organic chemical vapor deposition (MOCVD) process and a molecular beam epitaxy (MBE) process, the growth of quantum dot particles may be controlled.

The quantum dot may include a Group III-VI semiconductor compound, a Group II-VI semiconductor compound, a Group III-V semiconductor compound, a Group III-VI semiconductor compound, a Group I-III-VI semiconductor compound, a Group IV-VI semiconductor compound, a Group IV element or compound, or any combination thereof.

Examples of the Group III-VI semiconductor compound include a binary compound, such as In₂S₃; a ternary compound, such as AgInS, AgInS₂, CuInS, or CuInS₂; or any combination thereof.

Examples of the Group II-VI semiconductor compound include a binary compound, such as CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, and/or MgS; a ternary compound, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, and/or MgZnS; a quatemary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and/or HgZnSTe; and any combination thereof.

Examples of the Group III-V semiconductor compound include a binary compound, such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, and/or InSb; a ternary compound, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, InPSb, and/or GaAlNP; a quatemary compound, such as GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and/or InAlPSb; and any combination thereof. The Group III-V semiconductor compound may further include a Group II element.

Examples of the Group III-V semiconductor compound further including a Group II element include InZnP, InGaZnP, and InAlZnP.

Examples of the Group III-VI semiconductor compound include a binary compound, such as GaS, GaSe, Ga₂Se₃, GaTe, InS, InSe, In₂Se₃, and/or InTe; a ternary compound, such as InGaS₃, and/or InGaSe₃; and any combination thereof.

Examples of the Group I-III-VI semiconductor compound include a ternary compound, such as AgInS, AgInS₂, CuInS, CuInS₂, CuGaO₂, AgGaO₂, and/or AgAlO₂; and any combination thereof.

Examples of the Group IV-VI semiconductor compound include a binary compound, such as SnS, SnSe, SnTe, PbS, PbSe, and/or PbTe; a ternary compound, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, and/or SnPbTe; a quatemary compound, such as SnPbSSe, SnPbSeTe, and/or SnPbSTe; and any combination thereof.

In an embodiment, the Group IV element or compound may include a single element, such as Si or Ge; a binary compound, such as SiC and/or SiGe; or any combination thereof.

Each element included in the multi-element compound such as the binary compound, ternary compound, and quaternary compound may be present in a particle at a uniform concentration or a non-uniform concentration.

In some embodiments, the quantum dot may have a single structure having a uniform (e.g., substantially uniform) concentration of each element included in the corresponding quantum dot or a dual structure of a core-shell. In an embodiment, the material included in the core may be different from the material included in the shell.

The shell of the quantum dot may function as a protective layer for maintaining semiconductor characteristics by preventing or reducing chemical degeneration of the core and/or may function as a charging layer for imparting electrophoretic characteristics to the quantum dot. The shell may be a single layer or a multilayer. An interface between the core and the shell may have a concentration gradient in which the concentration of elements existing in the shell decreases along a direction toward the center.

Examples of the shell of the quantum dot include a metal and/or a non-metal oxide, a semiconductor compound, or any combination thereof. Examples of the oxide of metal and/or non-metal include a binary compound, such as SiO₂, Al₂O₃, TiO₂, ZnO, MnO, Mn₂O₃, Mn₃O₄, CuO, FeO, Fe₂O₃, FesO₄, CoO, Co₃O₄, and/or NiO; a ternary compound, such as MgAl₂O₄, CoFe₂O₄, NiFe₂O₄, and/or CoMn₂O₄; and any combination thereof. Examples of the semiconductor compound include, as described herein, Group III-VI semiconductor compounds, Group II-VI semiconductor compounds, Group III-V semiconductor compounds, Group III-VI semiconductor compounds, Group I-III-VI semiconductor compounds, Group IV-VI semiconductor compounds, or any combination thereof. In an embodiment, the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.

A full width at half maximum (FWHM) of an emission wavelength spectrum of the quantum dot may be about 45 nm or less, for example, about 40 nm or less, for example, about 30 nm or less. When the FWHM of the emission wavelength spectrum of the quantum dot is within any of the foregoing ranges, color purity and/or color reproduction may be improved. In addition, light emitted through such quantum dots is irradiated in omnidirection (e.g., substantially every direction). Accordingly, a wide viewing angle may be increased.

In addition, the quantum dot may be, for example, a spherical, pyramidal, multi-arm, or cubic nanoparticle, a nanotube, a nanowire, a nanofiber, or nanoplate particle.

By adjusting the size of the quantum dot, the energy band gap may also be adjusted, thereby obtaining light of various suitable wavelengths in the quantum dot emission layer. Therefore, by using quantum dots of different sizes, a light-emitting device that emits light of various suitable wavelengths may be implemented. In an embodiment, the size of the quantum dot may be selected to emit red, green and/or blue light. In addition, the size of the quantum dot may be adjusted such that light of various suitable colors are combined to emit white light.

Electron Transport Region in Interlayer 130

The electron transport region may have: i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.

The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.

In an embodiment, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein, for each structure, constituting layers are sequentially stacked from an emission layer.

The electron transport region (for example, the buffer layer, the hole blocking layer, the electron control layer, or the electron transport layer in the electron transport region) may include a metal-free compound including at least one π electron-deficient nitrogen-containing C₁-C₆₀cyclic group.

In an embodiment, the electron transport region may include a compound represented by Formula 601 below:

[Ar₆₀₁]_xe11-[(L₆₀₁)_xe1-R₆₀₁]_xe21 Formula 601

wherein, in Formula 601,

Ar₆₀₁and L₆₀₁may each independently be a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a,

xe11 is 1, 2, or 3,

xe1 may be 0, 1, 2, 3, 4, or 5,

R₆₀₁may be a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R10a, —Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃), —C(═O)(Q₆₀₁), —S(═O)₂(Q₆₀₁), or —P(═O)(Q₆₀₁)(Q₆₀₂),

Q₆₀₁to Q₆₀₃are the same as described in connection with Q₁,

xe21 may be 1, 2, 3, 4, or 5, and

at least one selected from Ar₆₀₁, L₆₀₁, and R₆₀₁may each independently be a TT electron-deficient nitrogen-containing C₁-C₆₀cyclic group unsubstituted or substituted with at least one R_10a.

In one or more embodiments, when xe11 in Formula 601 is 2 or more, two or more of Ar₆₀₁(s) may be linked to each other via a single bond.

In an embodiment, Ar₆₀₁in Formula 601 may be a substituted or unsubstituted anthracene group.

In an embodiment, the electron transport region may include a compound represented by Formula 601-1:

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wherein, in Formula 601-1,

X₆₁₄may be N or C(R₆₁₄), X₆₁₅may be N or C(R₆₁₅), X₆₁₆may be N or C(R₆₁₆), and at least one selected from X₆₁₄to X₆₁₆may be N,

L₆₁₁to L₆₁₃may be understood by referring to the description presented in connection with L₆₀₁,

xe611 to xe613 may be understood by referring to the description presented in connection with xe1,

R₆₁₁to R₆₁₃may be understood by referring to the description presented in connection with R₆₀₁, and

R₆₁₄to R₆₁₆may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10a, or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a.

In an embodiment, xe1 and xe611 to xe613 in Formula 601 and 601-1 may each independently be 0, 1, or 2.

The electron transport region may include at least one selected from Compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq₃, BAlq, TAZ, NTAZ, or any combination thereof:

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The thickness of the electron transport region may be in a range from about 160 Å to about 5000 Å, for example, about 100 Å to about 4000 Å. When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be in a range from about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å, and the thickness of the electron transport layer may be from about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport layer are within any of these ranges, suitable or satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.

The electron transport region (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.

The metal-containing material may include an alkali metal complex, an alkaline earth-metal complex, or any combination thereof. A metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and a metal ion of the alkaline earth-metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may be a hydroxy quinoline, a hydroxy isoquinoline, a hydroxy benzoquinoline, a hydroxy acridine, a hydroxy phenanthridine, a hydroxy phenyloxazole, a hydroxy phenylthiazole, a hydroxy diphenyloxadiazole, a hydroxy diphenylthiadiazole, a hydroxy phenylpyridine, a hydroxy phenylbenzimidazole, a hydroxy phenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.

In an embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) or ET-D2:

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The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may directly contact (e.g., physically contact) the second electrode 150.

The electron injection layer may have: i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.

The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof.

The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.

The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may include oxides and halides (for example, fluorides, chlorides, bromides, and/or iodides) of the alkali metal, the alkaline earth metal, and the rare earth metal, telluride, or any combination thereof.

The alkali metal-containing compound may include alkali metal oxides, such as Li₂O, Cs₂O, and/or K₂O, and alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and/or KI, or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound, such as BaO, SrO, CaO, Ba_xSr_1-xO (x is a real number that satisfies the condition of 0<x<1), or Ba_xCa_1-xO (x is a real number that satisfies the condition of 0<x<1). The rare earth metal-containing compound may include YbF₃, ScF₃, Sc₂O₃, Y₂O₃, Ce₂O₃, GdF₃, TbF₃, YbI₃, ScI₃, TbI₃, or any combination thereof. In an embodiment, the rare earth metal-containing compound may include lanthanide metal telluride. Examples of the lanthanide metal telluride include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La₂Te₃, Ce₂Te₃, Pr₂Te₃, Nd₂Te₃, Pm₂Te₃, Sm₂Te₃, Eu₂Te₃, Gd₂Te₃, Tb₂Te₃, Dy₂Te₃, Ho₂Te₃, Er₂Te₃, Tm₂Te₃, Yb₂Te₃, and Lu₂Te₃.

The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include i) one of ions of the alkali metal, the alkaline earth metal, and the rare earth metal and ii), as a ligand linked to the metal ion, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenyl benzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

The electron injection layer may include (e.g., consist of) an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof, and/or may further include an organic material (for example, a compound represented by Formula 601).

In an embodiment, the electron injection layer may include (e.g., consist of) i) an alkali metal-containing compound (for example, an alkali metal halide), or ii) a) an alkali metal-containing compound (for example, an alkali metal halide); and b) alkali metal, alkaline earth metal, rare earth metal, or any combination thereof. In an embodiment, the electron injection layer may be a KI:Yb co-deposited layer or a RbI:Yb co-deposited layer.

When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.

A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, or, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within any of the ranges described above, the electron injection layer may have suitable or satisfactory electron injection characteristics without a substantial increase in driving voltage.

Second Electrode 150

The second electrode 150 may be on the interlayer 130 having such a structure. The second electrode 150 may be a cathode, which is an electron injection electrode, and as the material for the second electrode 150, a metal, an alloy, an electrically conductive compound, or any combination thereof, each having a low work function, may be used.

The second electrode 150 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ytterbium (Yb), silver-ytterbium (Ag—Yb), ITO, IZO, and a combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode 150 may have a single-layered structure or a multi-layered structure including two or more layers.

Capping Layer

A first capping layer may be located outside the first electrode 110, and/or a second capping layer may be located outside the second electrode 150. In more detail, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are sequentially stacked in this stated order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in this stated order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in this stated order.

Light generated in an emission layer 133 of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the first electrode 110, which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer, and light generated in an emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the second electrode 150, which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer.

The first capping layer and the second capping layer may increase external luminescence efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 is increased, so that the luminescence efficiency of the light-emitting device 10 may be improved.

Each of the first capping layer and the second capping layer may include a material having a refractive index of 1.6 or more (at a wavelength of 589 nm).

The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material.

At least one selected from the first capping layer and the second capping layer may each independently include a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphyrine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth-metal complex, or a combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may be optionally substituted with a substituent containing O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof.

In an embodiment, at least one selected from the first capping layer and the second capping layer may each independently include an amine group-containing compound.

In an embodiment, at least one selected from the first capping layer and second capping layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.

In one or more embodiments, at least one selected from the first capping layer and the second capping layer may each independently include a compound selected from Compounds HT28 to HT33, Compounds CP1 to CP6, β-NPB, or any combination thereof:

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Electronic Apparatus

The light-emitting device may be included in various suitable electronic apparatuses. In an embodiment, the electronic apparatus including the light-emitting device may be a light-emitting apparatus, an authentication apparatus, and/or the like.

The electronic apparatus (for example, light-emitting apparatus) may further include, in addition to the light-emitting device, i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and/or the color conversion layer may be in at least one traveling direction of light emitted from the light-emitting device. In an embodiment, light emitted from the light-emitting device may be blue light and/or white light. The light-emitting device may be the same as described above. In an embodiment, the color conversion layer may include quantum dots. The quantum dot may be, for example, a quantum dot as described herein.

The electronic apparatus may include a first substrate. The first substrate includes a plurality of subpixel areas, the color filter includes a plurality of color filter areas corresponding to the plurality of subpixel areas, respectively, and the color conversion layer may include a plurality of color conversion areas corresponding to the subpixel areas, respectively.

A pixel-defining film may be between the plurality of subpixel areas to define each of the subpixel areas.

The color filter may further include the color filter areas and a light-blocking pattern between adjacent color filter areas (or adjacent color conversion layers) of the color filter areas, and the color conversion layer may further include the color conversion areas and a light-blocking pattern between adjacent color conversion areas (or adjacent color conversion layers) of the color conversion areas.

The color filter areas (or the color conversion areas) may include a first area emitting first color light, a second area emitting second color light, and/or a third area emitting third color light, and the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths from one another. In an embodiment, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In an embodiment, the color filter areas (or the color conversion areas) may include quantum dots. In more detail, the first area may include a red quantum dot, the second area may include a green quantum dot, and the third area may not include a quantum dot. The quantum dot is the same as described elsewhere in the present specification. Each of the first area, the second area and/or the third area may further include a scattering body.

In an embodiment, the light-emitting device may emit a first light, the first area may absorb the first light to emit a first first-color light, the second area may absorb the first light to emit a second first-color light, and the third area may absorb the first light to emit a third first-color light. In this regard, the first first-color light, the second first-color light, and the third first-color light may have different maximum emission wavelengths from one another. In more detail, the first light may be blue light, the first first-color light may be red light, the second first-color light may be green light, and the third first-color light may be blue light.

The electronic apparatus may further include a thin-film transistor in addition to the light-emitting device 1 as described above. The thin-film transistor may include a source electrode, a drain electrode, and an activation layer, wherein any one selected from the source electrode and the drain electrode may be electrically coupled to any one selected from the first electrode and the second electrode of the light-emitting device.

The thin-film transistor may further include a gate electrode, a gate insulation layer, and/or the like.

The active layer may include crystalline silicon, amorphous silicon, organic semiconductor, oxide semiconductor, and/or the like.

The electronic apparatus may further include a sealing portion for sealing the light-emitting device. The sealing portion may be between the color filter and/or the color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device 10 to be extracted to the outside, while concurrently (e.g., simultaneously) preventing or reducing penetration of ambient air and moisture into the light-emitting device 10. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer including at least one layer of an organic layer and/or an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic apparatus may be flexible.

On the sealing portion, in addition to the color filter and/or color conversion layer, various suitable functional layers may be further located according to the use of the electronic apparatus. The functional layers may include a touch screen layer, a polarizing layer, and/or the like. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, and/or an infrared touch screen layer. The authentication apparatus may be, for example, a biometric authentication apparatus for authenticating an individual by using biometric information of a biometric body (for example, a fingertip, a pupil, and/or the like).

The authentication apparatus may further include, in addition to the light-emitting device, a biometric information collector.

The electronic apparatus may be applied to various suitable displays, light sources, lighting, personal computers (for example, a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (for example, electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, and/or endoscope displays), fish finders, various suitable measuring instruments, meters (for example, meters for a vehicle, an aircraft, and/or a vessel), projectors, and/or the like.

Description of FIGS. 2 and 3

FIG. 2 is a cross-sectional view showing a light-emitting apparatus according to an embodiment of the present disclosure.

The light-emitting apparatus of FIG. 2 includes a substrate 100, a thin-film transistor (TFT), a light-emitting device, and an encapsulation portion 300 that seals the light-emitting device.

The substrate 100 may be a flexible substrate, a glass substrate, and/or a metal substrate. A buffer layer 210 may be on the substrate 100. The buffer layer 210 prevents or reduces the penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.

A TFT may be on the buffer layer 210. The TFT may include an activation layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.

The activation layer 220 may include an inorganic semiconductor such as silicon and/or polysilicon, an organic semiconductor, and/or an oxide semiconductor, and may include a source region, a drain region and a channel region.

A gate insulating film 230 for insulating the activation layer 220 from the gate electrode 240 may be on the activation layer 220, and the gate electrode 240 may be on the gate insulating film 230.

An interlayer insulating film 250 may be on the gate electrode 240. The interlayer insulating film 250 is between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.

The source electrode 260 and the drain electrode 270 may be on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may expose the source region and the drain region of the activation layer 220, and the source electrode 260 and the drain electrode 270 may be in contact (e.g., physical contact) with the exposed portions of the source region and the drain region of the activation layer 220.

The TFT may be electrically coupled to a light-emitting device to drive the light-emitting device, and is covered by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. A light-emitting device is provided on the passivation layer 280. The light-emitting device includes the first electrode 110, the interlayer 130, and the second electrode 150.

The first electrode 110 may be on the passivation layer 280. The passivation layer 280 does not completely cover the drain electrode 270 and exposes a portion of the drain electrode 270, and the first electrode 110 may be coupled to the exposed portion of the drain electrode 270.

A pixel defining layer 290 including an insulating material may be on the first electrode 110. The pixel defining layer 290 may expose a certain region of the first electrode 110, and the interlayer 130 may be formed in the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide and/or polyacryl-based organic film. In some embodiments, at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel defining layer 290 and may thus be in the form of a common layer.

The second electrode 150 may be on the interlayer 130, and a capping layer 170 may be additionally on the second electrode 150. The capping layer 170 may cover the second electrode 150.

The encapsulation portion 300 may be on the capping layer 170. The encapsulation portion 300 may be on a light-emitting device and protects the light-emitting device from moisture and/or oxygen. The encapsulation portion 300 may include: an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or a combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (for example, polymethyl methacrylate or polyacrylic acid), an epoxy-based resin (for example, aliphatic glycidyl ether (AGE)), or a combination thereof; or a combination of an inorganic film and an organic film.

FIG. 3 is a cross-sectional view showing a light-emitting apparatus according to an embodiment of the present disclosure.

The light-emitting apparatus of FIG. 3 is the same as the light-emitting apparatus of FIG. 2, except that a light-blocking pattern 500 and a functional region 400 are additionally on the encapsulation portion 300. The functional region 400 may be i) a color filter area, ii) a color conversion areas, or iii) a combination of the color filter area and the color conversion area. In an embodiment, the light-emitting device included in the light-emitting apparatus of FIG. 3 may be a tandem light-emitting device.

Preparation Method

Layers constituting the hole transport region, an emission layer, and layers constituting the electron transport region may be formed in a certain region by using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, and laser-induced thermal imaging.

When layers constituting the hole transport region, the emission layer, and layers constituting the electron transport region are formed by vacuum deposition, the deposition may be performed at a deposition temperature in a range of about 100° C. to about 500° C., a vacuum degree in a range of about 10⁻⁸torr to about 10⁻³torr, and a deposition speed in a range of about 0.01 Å/sec to about 100 Å/sec by taking into account a material to be included in a layer to be formed and the structure of a layer to be formed.

Definition of at Least Some of the Terms

The term “C₃-C₆₀carbocyclic group,” as used herein, refers to a cyclic group that consists of carbon only and has three to sixty carbon atoms, and the term “C₁-C₆₀heterocyclic group,” as used herein, refers to a cyclic group that has one to sixty carbon atoms and further includes, in addition to carbon, a heteroatom. The C₃-C₆₀carbocyclic group and the C₁-C₆₀heterocyclic group may each be a monocyclic group that consists of one ring or a polycyclic group in which two or more rings are condensed with each other (e.g., combined together with each other). In an embodiment, the number of ring-forming atoms of the C₁-C₆₀heterocyclic group may be in a range from 3 to 61.

The term “cyclic group,” as used herein, includes the C₃-C₆₀carbocyclic group and the C₁-C₆₀heterocyclic group.

The term “π electron-rich C₃-C₆₀cyclic group,” as used herein, refers to a cyclic group that has three to sixty carbon atoms and does not include *—N═*′ as a ring-forming moiety, and the term “π electron-deficient nitrogen-containing C₁-C₆₀cyclic group,” as used herein, refers to a heterocyclic group that has one to sixty carbon atoms and includes *—N═*′ as a ring-forming moiety.

For example, the C₃-C₆₀carbocyclic group may be i) a group T1 or ii) a condensed cyclic group in which two or more groups T1 are condensed with (e.g., combined together with) each other (for example, a cyclopentadiene group, an adamantane group, a norbornane group, a benzene group, a pentalene group, a naphthalene group, an azulene group, an indacene group, acenaphthylene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a perylene group, a pentaphene group, a heptalene group, a naphthacene group, a picene group, a hexacene group, a pentacene group, a rubicene group, a coronene group, an ovalene group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, an indenophenanthrene group, or an indenoanthracene group),

the C₁-C₆₀heterocyclic group may be i) a group T2, ii) a condensed cyclic group in which two or more groups T2 are condensed with (e.g., combined together with) each other, or iii) a condensed cyclic group in which at least one group T2 and at least one group T1 are condensed with (e.g., combined together with) each other (for example, a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothieno dibenzothiophene group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, or an azadibenzofuran group),

the π electron-rich C₃-C₆₀cyclic group may be i) a group T1, ii) a condensed cyclic group in which two or more groups T1 are condensed with (e.g., combined together with) each other, iii) a group T3, iv) a condensed cyclic group in which two or more groups T3 are condensed with (e.g., combined together with) each other, or v) a condensed cyclic group in which at least one group T3 and at least one group T1 are condensed with (e.g., combined together with) each other (for example, a C₃-C₆₀carbocyclic group, a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, or a benzothienodibenzothiophene group),

the π electron-deficient nitrogen-containing C₁-C₆₀cyclic group may be i) a group T4, ii) a condensed cyclic group in which two or more groups T4 are condensed with (e.g., combined together with) each other, iii) a condensed cyclic group in which at least one group T4 and at least one group T1 are condensed with (e.g., combined together with) each other, iv) a condensed cyclic group in which at least one group T4 and at least one group T3 are condensed with (e.g., combined together with) each other, or v) a condensed cyclic group in which at least one group T4, at least one group T1, and at least one group T3 are condensed with (e.g., combined together with) each other (for example, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, or an azadibenzofuran group),

the group T1 may be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane group (or, a bicyclo[2.2.1]heptane group), a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, or a benzene group,

the group T2 may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetrazine group,

the group T3 may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, or a borole group,

the group T4 may be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetrazine group.

The terms “the cyclic group,” “the C₃-C₆₀carbocyclic group,” “the C₁-C₆₀heterocyclic group,” “the π electron-rich C₃-C₆₀cyclic group,” or “the u electron-deficient nitrogen-containing C₁-C₆₀cyclic group,” as used herein, refer to a group that is condensed with (e.g., combined together with) a cyclic group, a monovalent group, a polyvalent group (for example, a divalent group, a trivalent group, a tetravalent group, or the like), according to the structure of a formula described with corresponding terms. In an embodiment, “a benzene group” may be a benzo group, a phenyl group, a phenylene group, or the like, which may be easily understand by one of ordinary skill in the art according to the structure of a formula including the “benzene group.”

In an embodiment, examples of the monovalent C₃-C₆₀carbocyclic group and the monovalent C₁-C₆₀heterocyclic group include a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, and examples of the divalent C₃-C₆₀carbocyclic group and the monovalent C₁-C₆₀heterocyclic group are a C₃-C₁₀cycloalkylene group, a C₁-C₁₀heterocycloalkylene group, a C₃-C₁₀cycloalkenylene group, a C₁-C₁₀heterocycloalkenylene group, a C₆-C₆₀arylene group, a C₁-C₆₀heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.

The term “C₁-C₆₀alkyl group,” as used herein, refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group. The term “C₁-C₆₀alkylene group,” as used herein, refers to a divalent group having substantially the same structure as the C₁-C₆₀alkyl group.

The term “C₂-C₆₀alkenyl group,” as used herein, refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond at a main chain (e.g., in the middle) or at a terminal end (e.g., the terminus) of a C₂-C₆₀alkyl group, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C₂-C₆₀alkenylene group,” as used herein, refers to a divalent group having substantially the same structure as the C₂-C₆₀alkenyl group.

The term “C₂-C₆₀alkynyl group,” as used herein, refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond at a main chain (e.g., in the middle) or at a terminal end (e.g., the terminus) of a C₂-C₆₀alkyl group, and examples thereof include an ethynyl group, and a propynyl group. The term “C₂-C₆₀alkynylene group,” as used herein, refers to a divalent group having substantially the same structure as the C₂-C₆₀alkynyl group.

The term “C₁-C₆₀alkoxy group,” as used herein, refers to a monovalent group represented by —OA₁₀₁(wherein A₁₀₁is the C₁-C₆₀alkyl group), and examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.

The term “C₃-C₁₀cycloalkyl group,” as used herein, refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples thereof are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl group, an adamantanyl group, a norbornanyl group (or a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group. The term “C₃-C₁₀cycloalkylene group,” as used herein, refers to a divalent group having substantially the same structure as the C₃-C₁₀cycloalkyl group.

The term “C₁-C₁₀heterocycloalkyl group,” as used herein, refers to a monovalent cyclic group that further includes, in addition to a carbon atom, at least one heteroatom as a ring-forming atom and has 1 to 10 carbon atoms, and examples thereof are a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C₁-C₁₀heterocycloalkylene group,” as used herein, refers to a divalent group having substantially the same structure as the C₁-C₁₀heterocycloalkyl group.

The term “C₃-C₁₀cycloalkenyl group,” as used herein, refers to a monovalent cyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity (e.g., is not aromatic), and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C₃-C₁₀cycloalkenylene group,” as used herein, refers to a divalent group having substantially the same structure as the C₃-C₁₀cycloalkenyl group.

The term “C₁-C₁₀heterocycloalkenyl group,” as used herein, refers to a monovalent cyclic group that has, in addition to a carbon atom, at least one heteroatom as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in the cyclic structure thereof. Examples of the C₁-C₁₀heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C₁-C₁₀heterocycloalkenylene group,” as used herein, refers to a divalent group having substantially the same structure as the C₁-C₁₀heterocycloalkenyl group.

The term “C₆-C₆₀aryl group,” as used herein, refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term “C₆-C₆₀arylene group,” as used herein, refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Examples of the C₆-C₆₀aryl group include fluorenyl group, a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl 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 pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, and an ovalenyl group. When the C₆-C₆₀aryl group and the C₆-C₆₀arylene group each include two or more rings, the two or more rings may be condensed to each other (e.g., combined together with each other).

The term “C₁-C₆₀heteroaryl group,” as used herein, refers to a monovalent group having a heterocyclic aromatic system that has, in addition to a carbon atom, at least one heteroatom as a ring-forming atom, and 1 to 60 carbon atoms. The term “C₁-C₆₀heteroarylene group,” as used herein, refers to a divalent group having a heterocyclic aromatic system that has, in addition to a carbon atom, at least one heteroatom as a ring-forming atom, and 1 to 60 carbon atoms. Examples of the C₁-C₆₀heteroaryl group include a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, and a naphthyridinyl group. When the C₁-C₆₀heteroaryl group and the C₁-C₆₀heteroarylene group each include two or more rings, the two or more rings may be condensed with each other (e.g., combined together with each other).

The term “monovalent non-aromatic condensed polycyclic group,” as used herein, refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed with each other (e.g., combined together with each other), only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure (e.g., is not aromatic when considered as a whole). Examples of the monovalent non-aromatic condensed polycyclic group include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, and an indenoanthracenyl group. The term “divalent non-aromatic condensed polycyclic group,” as used herein, refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group,” as used herein, refers to a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings condensed to each other (e.g., combined together with each other), at least one heteroatom other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure (e.g., is not aromatic when considered as a whole). Examples of the monovalent non-aromatic condensed heteropolycyclic group include a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphthoindolyl group, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indenocarbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthosilolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, and a benzothienodibenzothiophenyl group. The term “divalent non-aromatic condensed heteropolycyclic group,” as used herein, refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

The term “C₆-C₆₀aryloxy group,” as used herein, refers to —OA₁₀₂(wherein A₁₀₂is the C₆-C₆₀aryl group), and the term “C₆-C₆₀arylthio group,” as used herein, refers to —SA₁₀₃(wherein A₁₀₃is the C₆-C₆₀aryl group).

The term “R_10a,” as used herein, refers to:

deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;

a C₃-C₆₀carbocyclic group, a C₁-C₆₀heterocyclic group, a C₆-C₆₀aryloxy group, or a C₆-C₆₀arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₆₀carbocyclic group, a C₁-C₆₀heterocyclic group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), —P(═O)(Q₂₁)(Q₂₂), or any combination thereof; or

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), or —P(═O)(Q₃₁)(Q₃₂).

Q₁to Q₃, Q₁₁to Q₁₃, Q₂₁to Q₂₃and Q₃₁to Q₃₃used herein may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C₁-C₆₀alkyl group; a C₂-C₆₀alkenyl group; a C₂-C₆₀alkynyl group; a C₁-C₆₀alkoxy group; or a C₃-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, a C₁-C₆₀alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.

The term “hetero atom,” as used herein, refers to any atom other than a carbon atom. Examples of the heteroatom are O, S, N, P, Si, B, Ge, Se, and any combination thereof.

The term “Ph,” as used herein, refers to a phenyl group, the term “Me,” as used herein, refers to a methyl group, the term “Et,” as used herein, refers to an ethyl group, the term “ter-Bu” or “Bu^t,” as used herein, refers to a tert-butyl group, and the term “OMe,” as used herein, refers to a methoxy group.

The term “biphenyl group,” as used herein, refers to “a phenyl group substituted with a phenyl group.” In other words, the “biphenyl group” is a substituted phenyl group having a C₆-C₆₀aryl group as a substituent.

The term “terphenyl group,” as used herein, refers to “a phenyl group substituted with a biphenyl group.” In other words, the “terphenyl group” is a substituted phenyl group having, as a substituent, a C₆-C₆₀aryl group substituted with a C₆-C₆₀aryl group.

* and *′, as used herein, unless defined otherwise, each refer to a binding site to a neighboring atom in a corresponding formula.

Hereinafter, a compound according to embodiments and a light-emitting device according to embodiments will be described in more detail with reference to Synthesis Examples and Examples. The wording “B was used instead of A” used in describing Synthesis Examples refers to that an identical molar equivalent of B was used in place of A.

EXAMPLES
Synthesis Example 1: Synthesis of Compound 16

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Synthesis of Intermediate 16a

5-methylquinoline (1 eq) and iodine (0.2 eq) were added to dichloromethane, and then, in a nitrogen atmosphere, 4,4,5,5-tetramethyl-1,3,2-dioxaborole (4 eq) was added thereto and stirred at room temperature for 48 hours. After washing the resultant solution three times with dichloromethane and water, an organic layer that was obtained was dried with anhydrous magnesium sulfate and then dried under reduced pressure. Subsequently, the separation-purification process was performed by column chromatography to obtain Intermediate 16a. (Yield: 80%)

Synthesis of Intermediate 16b

1,3-dibromo-5-methylbenzene (1 eq), Intermediate 16a (2.1 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-t-butylphosphine (0.1 eq), and sodium t-butoxide (3 eq) were dissolved in toluene, and then, stirred for 2 hours at 100° C. in a nitrogen atmosphere. After cooling, an organic layer that was obtained by washing the resultant solution three times with ethyl acetate and water was dried using anhydrous magnesium sulfate and dried under reduced pressure. Subsequently, the separation-purification process was performed by column chromatography to obtain Intermediate 16b. (Yield: 82%)

Synthesis of Compound 16

After Intermediate 16b (1 eq) was dissolved in ortho-dichlorobenzene, the flask was cooled to 0° C. in the nitrogen atmosphere, and then BBr (2.5 eq) was slowly added thereto. After completion of the addition, the temperature was raised to 160° C. and stirred for 6 hours. After cooling, triethylamine was slowly dropped into the flask until the exotherm stopped to terminate the reaction, and then hexane was added thereto to precipitate a solid content. The obtained solid was separated and purified by column chromatography and then purified by MC/Hex recrystallization to obtain Compound 16. (Yield: 5%)

Synthesis Example 2: Synthesis of Compound 18

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Synthesis of Intermediate 18a

5-(t-butyl)quinoline (1 eq) and iodine (0.2 eq) were added to dichloromethane, and then, in a nitrogen atmosphere, 4,4,5,5-tetramethyl-1,3,2-dioxaborole (4 eq) was added dropwise thereto and stirred at room temperature for 48 hours. After washing the resultant solution three times with dichloromethane and water, an organic layer that was obtained was dried with anhydrous magnesium sulfate and then dried under reduced pressure. The organic layer was dried using MgSO₄and then dried under reduced pressure. Subsequently, the separation-purification process was performed by column chromatography to obtain Intermediate 18a. (Yield: 60%)

Synthesis of Intermediate 18b

1,3-dibromo-5-methylbenzene (1 eq), Intermediate 18a (2.1 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-t-butylphosphine (0.1 eq), and sodium t-butoxide (3 eq) were dissolved in toluene, and then, stirred for 2 hours at 100° C. in a nitrogen atmosphere. After cooling, an organic layer that was obtained by washing the resultant solution three times with ethyl acetate and water was dried using anhydrous magnesium sulfate and dried under reduced pressure. Subsequently, the separation-purification process was performed by column chromatography to obtain Intermediate 18b. (Yield: 85%)

Synthesis of Compound 18

After Intermediate 18b (1 eq) was dissolved in ortho-dichlorobenzene, the flask was cooled to 0° C. in a nitrogen atmosphere, and then BBr (2.5 eq) was slowly added dropwise thereto. After completion of the dropwise addition, the temperature was raised to 160° C. and stirred for 6 hours. After cooling, triethylamine was slowly dropped into the flask until the exotherm stopped to terminate the reaction, and then hexane was added thereto to precipitate a solid content. The obtained solid was purified by column chromatography and then purified by MC/Hex recrystallization to obtain Compound 18. (Yield: 4%)

Synthesis Example 3: Synthesis of Compound 21

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Synthesis of Intermediate 21a

5-bromoquinoline (1 eq), phenylboronic acid (1.5 eq), tetrakis (triphenylphosphine) palladium (0.05 eq), and potassium carbonate (3 eq) were dissolved in 4:1 volume ratio of THF:H₂O and then, in a nitrogen atmosphere, the mixture was stirred at 90° C. for 12 hours. After cooling, an organic layer that was obtained by washing the resultant solution three times with ethyl acetate and water was dried using anhydrous magnesium sulfate and dried under reduced pressure. Subsequently, the separation-purification process was performed by column chromatography to obtain Intermediate 21a. (Yield: 72%)

Synthesis of Intermediate 21b

Intermediate 21a (1 eq) and iodine (0.2 eq) were added to dichloromethane, and then, in a nitrogen atmosphere, 4,4,5,5-tetramethyl-1,3,2-dioxaborole (4 eq) was added dropwise thereto and stirred at room temperature for 48 hours. After washing the resultant solution three times with dichloromethane and water, an organic layer that was obtained was dried with anhydrous magnesium sulfate and then dried under reduced pressure. Subsequently, the separation-purification process was performed by column chromatography to obtain Intermediate 21b. (Yield: 70%)

Synthesis of Intermediate 21c

3,5-dibromo-1,1′-biphenyl (1 eq), Intermediate 21b (2.1 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-t-butylphosphine (0.1 eq), and sodium t-butoxide (3 eq) were dissolved in toluene, and then, stirred for 2 hours at 100° C. in a nitrogen atmosphere. After cooling, an organic layer that was obtained by washing the resultant solution three times with ethyl acetate and water was dried using anhydrous magnesium sulfate and dried under reduced pressure. Subsequently, the separation-purification process was performed by column chromatography to obtain Intermediate 21c. (Yield: 85%)

Synthesis of Compound 21

After Intermediate 21c (1 eq) was dissolved in ortho-dichlorobenzene, the flask was cooled to 0° C. in a nitrogen atmosphere, and then BBr (2.5 eq) was slowly added thereto. After completion of the addition, the temperature was raised to 160° C. and stirred for 6 hours. After cooling, triethylamine was slowly dropped into the flask until the exotherm stopped to terminate the reaction, and then hexane was added thereto to precipitate a solid content. Then, the obtained solid was separated and purified by column chromatography and then purified by MC/Hex recrystallization to obtain Compound 21. (Yield: 3%)

Synthesis Example 4: Synthesis of Compound 24

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Synthesis of Intermediate 24c

1,3-dibromo-5-(t-butyl)benzene (1 eq), Intermediate 21b (2.1 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-t-butylphosphine (0.1 eq), and sodium t-butoxide (3 eq) were dissolved in toluene, and then, stirred for 2 hours at 100° C. in a nitrogen atmosphere. After cooling, an organic layer that was obtained by washing the resultant solution three times with ethyl acetate and water was dried using anhydrous magnesium sulfate and dried under reduced pressure. Subsequently, the separation-purification process was performed by column chromatography to obtain Intermediate 24c. (Yield: 85%)

Synthesis of Compound 24

After Intermediate 24c (1 eq) was dissolved in ortho-dichlorobenzene, the flask was cooled to 0° C. in a nitrogen atmosphere, and then BBr (2.5 eq) was slowly added thereto. After completion of the addition, the temperature was raised to 160° C. and stirred for 6 hours. After cooling, triethylamine was slowly dropped into the flask until the exotherm stopped to terminate the reaction, and then hexane was added thereto to precipitate a solid content. The obtained solid was separated and purified by column chromatography and then purified by MC/Hex recrystallization to obtain Compound 24. (Yield: 5%)

Synthesis Example 5: Synthesis of Compound 90

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Synthesis of Intermediate 90a

3-(t-butyl)aniline (1 eq), bromobenzene (1.1 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-t-butylphosphine (0.1 eq), and sodium t-butoxide (3 eq) were dissolved in toluene, and then, stirred for 2 hours at 100° C. in a nitrogen atmosphere. After cooling, the organic layer obtained by washing three times with ethyl acetate and water, and was dried using anhydrous magnesium sulfate and dried under reduced pressure. Subsequently, the separation-purification process was performed by column chromatography to obtain Intermediate 90a. (Yield: 85%)

Synthesis of Intermediate 90b

1,3-dibromo-5-methylbenzene (1 eq), Intermediate 90a (2.1 eq), [1,1′-bis (diphenylphosphino)ferrocene]dichloropalladium(II) (0.03 eq), and sodium t-butoxide (1.2 eq) were dissolved in toluene and then stirred for 6 hours at 80° C. in a nitrogen atmosphere. After cooling, an organic layer that was obtained by washing the resultant solution three times with ethyl acetate and water was dried using anhydrous magnesium sulfate and dried under reduced pressure. Subsequently, the separation-purification process was performed by column chromatography to obtain Intermediate 90b. (Yield: 85%)

Synthesis of Intermediate 90c

Intermediate 90b (1 eq), 5-(t-butyl)-1,2,3,4-tetrahydroquinoline (1.1 eq), tris(dibenzylidene-acetone)dipalladium(0) (0.05 eq), tri-t-butylphosphine (0.1 eq), and sodium t-butoxide (3 eq) were dissolved in toluene, and then, stirred for 2 hours at 100° C. in a nitrogen atmosphere. After cooling, an organic layer that was obtained by washing the resultant solution three times with ethyl acetate and water was dried using anhydrous magnesium sulfate and dried under reduced pressure. Subsequently, the separation-purification process was performed by column chromatography to obtain Intermediate 90c. (Yield: 85%)

Synthesis of Compound 90

After Intermediate 90c (1 eq) was dissolved in ortho-dichlorobenzene, the flask was cooled to 0° C. in a nitrogen atmosphere, and then BBr (2.5 eq) was slowly added thereto. After completion of the addition, the temperature was raised to 160° C. and stirred for 6 hours. After cooling, triethylamine was slowly dropped into the flask until the exotherm stopped to terminate the reaction, and then hexane was added thereto to precipitate a solid content. The obtained solid was separated and purified by column chromatography and then purified by MC/Hex recrystallization to obtain Compound 90. (Yield: 5%)

Synthesis Example 6: Synthesis of Compound 96

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Synthesis of Intermediate 96a

[1,1′-biphenyl]-3-amine (1 eq), bromobenzene (1.1 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-t-butylphosphine (0.1 eq), and sodium t-butoxide (3 eq) were dissolved in toluene, and then, stirred for 2 hours at 100° C. in a nitrogen atmosphere. After cooling, an organic layer that was obtained by washing the resultant solution three times with ethyl acetate and water was dried using anhydrous magnesium sulfate and dried under reduced pressure. Subsequently, the separation-purification process was performed by column chromatography to obtain Intermediate 96a. (Yield: 85%)

Synthesis of Intermediate 96b

1,3-dibromo-5-methylbenzene (1 eq), Intermediate 96a (2.1 eq), [1,1′-bis (diphenylphosphino)ferrocene]dichloropalladium(II) (0.03 eq), and sodium t-butoxide (3 eq) were dissolved in toluene and then stirred for 6 hours at 80° C. in a nitrogen atmosphere. After cooling, an organic layer that was obtained by washing the resultant solution three times with ethyl acetate and water was dried using anhydrous magnesium sulfate and dried under reduced pressure. Subsequently, the separation-purification process was performed by column chromatography to obtain Intermediate 96b. (Yield: 62%)

Synthesis of Intermediate 96c

Intermediate 96b (1 eq), 5-phenyl-1,2,3,4-tetrahydroquinoline (1.1 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-t-butylphosphine (0.1 eq), and sodium t-butoxide (3 eq) were dissolved in toluene, and then, stirred for 2 hours at 100° C. in a nitrogen atmosphere. After cooling, an organic layer that was obtained by washing the resultant solution three times with ethyl acetate and water was dried using anhydrous magnesium sulfate and dried under reduced pressure. Subsequently, the separation-purification process was performed by column chromatography to obtain Intermediate 96c. (Yield: 85%)

Synthesis of Compound 96

After Intermediate 96c (1 eq) was dissolved in ortho-dichlorobenzene, the flask was cooled to 0° C. in a nitrogen atmosphere, and then BBr (2.5 eq) was slowly added thereto. After completion of the addition, the temperature was raised to 160° C. and stirred for 6 hours. After cooling, triethylamine was slowly dropped into the flask until the exotherm stopped to terminate the reaction, and then hexane was added thereto to precipitate a solid content. The obtained solid was separated and purified by column chromatography and then purified by MC/Hex recrystallization to obtain Compound 96. (Yield: 5%)

Table 1 shows ¹H NMR and MS/FAB of the compounds synthesized as described above. Compounds other than the compounds shown in Table 1 may be easily recognized by those skilled in the art by referring to the above synthesis routes and source materials.

TABLE 1

Com-

MS/FAB

pound
H NMR (δ)
Calc
found

16
8.62 (2H, d), 7.17 (2H, d), 6.51 (2H, s),
390.23
309.33

3.34 (4H, m), 3.13 (4H, m), 2.34 (10H,

m), 2.23 (3H, s)

18
8.58 (2H, d), 7.15 (2H d), 6.50 (2H, s),
516.37
516.28

3.32 (4H, m), 3.15 (4H, m), 2.31 (4H,

m), 1.37 (18H, s) 1.35 (9H, s)

21
8.75 (2H, d), 7.43 (12H, m), 7.38 (1H, t),
576.27
576.23

7.33 (2H, t) 7.17 (2H, d), 6.48 (2H, s),

3.34 (4H, m), 3.13 (4H, m), 2.34 (4H, m)

24
8.73 (2H, d), 7.44 (8H, m), 7.33 (2H, t)
556.30
556.26

7.17 (2H, d), 6.53 (2H, s), 3.34 (4H, m),

3.11 (4H, m), 2.35 (4H, m), 1.35 (9H, m)

90
8.79 (1H, d), 8.75 (1H, d), 7.23 (2H, m),

7.13 (2H, d), 7.20 (1H, d), 7.19 (1H, d),

6.97 (1H, d), 6.80 (1H, s), 6.71 (1H, s),

6.55 (1H, s), 3.36 (2H, m) 3.17 (2H, m),
552.37
552.55

2.36 (2H, m), 1.37 (9H, s) 1.35 (18H,

m)

96
8.75 (1H, d), 8.73 1H, d), 7.42 (8H, m),
592.30
592.75

7.34 (2H, m) 7.22 (3H, m), 7.16 (1H, d),

7.15 (1H, d), 7.11 (2H, d), 6.95 (1H, t),

6.72 (1H, s), 6.52 (1H, s), 3.35 (2H, m),

3.19 (2H, m), 2.34 (2H, m), 1.35 (9H,

s)

Example 1

As an anode, a Corning 15 Ω/cm²(1,200 Å) ITO glass substrate was cut to a size of 50 mm×50 mm×0.7 mm, sonicated with isopropyl alcohol and pure water each for 5 minutes, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. The ITO glass substrate was provided to a vacuum deposition apparatus.

N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPD) was vacuum-deposited on the ITO anode formed on the glass substrate to form a hole injection layer having a thickness of 300 Å, and then, Compound HT3 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 200 Å.

A hole transport compound CzSi was vacuum deposited on the hole transport layer to form an emission auxiliary layer having a thickness of 100 Å.

mCP(host) and Compound 16 (dopant) were co-deposited to a weight ratio of 99:1 on the emission auxiliary layer to form an emission layer having a thickness of 200 Å.

Then, TSPO1 was deposited on the emission layer to form an electron transport layer having a thickness of 200 Å, and then, TPBI was deposited on the electron transport layer to form a buffer layer having a thickness of 300 Å.

LiF, a halogenated alkali metal, was deposited on the buffer layer to form an electron injection layer having a thickness of 10 Å, and Al was vacuum-deposited thereon to form an Al electrode having a thickness of 3000 Å, and Compound HT28 was deposited on the electrode to form a capping layer having a thickness of 700 Å, thereby completing the manufacture of a light-emitting device.

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Examples 2 to 12 and Comparative Examples 1 to 3

A light-emitting device was manufactured in substantially the same manner as used in Example 1, except that, in forming the hole transport layer and the emission layer, the compounds shown in Table 2 were used.

Evaluation Example 1

To evaluate characteristics of the light-emitting devices manufactured according to Examples 1 to 12 and Comparative Examples 1 to 3, the driving voltage at the current density of 10 mA/cm², luminescence efficiency, and maximum external quantum efficiency (EQE) thereof were measured. The driving voltage of an light-emitting device were measured using a source meter (Keithley Instrument Inc., 2400 series), and the maximum external quantum efficiency was measured using an external quantum efficiency measurement device C9920-2-12 of Hamamatsu Photonics Inc. In evaluating the maximum external quantum efficiency, the luminance/current density was measured using a luminance meter that was calibrated for wavelength sensitivity, and the maximum external quantum efficiency was converted by assuming an angular luminance distribution (Lambertian) which introduced a perfect reflecting diffuser. Table 2 below shows the evaluation results of the characteristics of the light-emitting devices.

TABLE 2

Maximum

Material for
Material for
Driving

quantum

hole transport
emission
voltage
Efficiency
Efficiency
Emission

layer
layer
(V)
(cd/A)
(%)
color

Example 1
HT3
Compound 16
5.2
18.8
20.8
Blue

Example 2
HT3
Compound 18
5.1
20.3
22.1
Blue

Example 3
HT3
Compound 21
5.2
14.8
18.4
Blue

Example 4
HT3
Compound 24
4.8
22.1
22.8
Blue

Example 5
HT3
Compound 90
5.0
19.2
20.0
Blue

Example 6
HT3
Compound 96
5.2
18.8
19.0
Blue

Example 7
HT44
Compound 16
5.4
18.1
19.2
Blue

Example 8
HT44
Compound 18
5.3
19.2
20.1
Blue

Example 9
HT44
Compound 21
5.4
15.0
15.8
Blue

Example 10
HT44
Compound 24
5.0
20.4
21.0
Blue

Example 11
HT44
Compound 90
5.5
17.4
18.2
Blue

Example 12
HT44
Compound 96
5.7
16.2
18.8
Blue

Comparative
HT3
DABNA-1
5.7
15.6
16.1
Blue

Example 1

Comparative
HT3
CE1
5.4
17.2
18.4
Blue

Example 2

Comparative
HT3
CE2
5.8
14.1
15.3
Blue

Example 3

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From Table 2, it can be seen that the light-emitting devices of Examples 1 to 12 have improved driving voltage, luminescence efficacy, and external quantum efficiency at the same time compared to the light-emitting devices of Comparative Examples 1 to 3.

Example 13

As an anode, a Corning 15 Ω/cm²(1,200 Å) ITO glass substrate was cut to a size of 50 mm×50 mm×0.7 mm, sonicated with isopropyl alcohol and pure water each for 15 minutes, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. The ITO glass substrate was provided to a vacuum deposition apparatus.

m-MTDATA was vacuum-deposited on the ITO anode formed on the glass substrate to form a hole injection layer having a thickness of 600 Å, and then, Compound HT3 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 100 Å.

Compound AH-1(host) and Compound 16 (dopant) were co-deposited to a weight ratio of 97:3 on the hole transport layer to form an emission layer having a thickness of 300 Å.

Then, Compound ET37 was deposited on the emission layer to form a hole blocking layer having a thickness of 100 Å, and then, Compounds ET42 and LiQ were co-deposited to a weight ratio of 50:50 on the hole blocking layer to form an electron transport layer having a thickness of 200 Å.

Al was vacuum-deposited on the electron transport layer to form a cathode having a thickness of 2000 Å, and Compound HT28 was deposited thereon to form a capping layer having a thickness of 700 Å, thereby completing the manufacture of a light-emitting device.

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Examples 14 to 18 and Comparative Examples 4 to 6

Light-emitting devices were manufactured in substantially the same manner as in Example 13, except that, in forming the emission layer, the compounds shown in Table 3 were each used instead of Compound 16.

Evaluation Example 2

The characteristics of the light-emitting devices manufactured according to Examples 14 to 18 and Comparative Examples 4 to 6 were evaluated by measuring the driving voltage at the current density of 10 mA/cm²and luminescence efficiency thereof in the same manner as used in Evaluation Example 1. The evaluation results of the characteristics of the light-emitting devices are shown in Table 3 below.

TABLE 3

Dopant of
Driving voltage
Efficiency

emission layer
(V)
(cd/A)

Example 13
Compound 16
5.10
4.21

Example 14
Compound 18
4.67
4.42

Example 15
Compound 21
4.82
3.88

Example 16
Compound 24
4.66
4.37

Example 17
Compound 90
4.88
4.22

Example 18
Compound 92
4.90
4.20

Comparative
DABNA-1
5.51
3.81

Example 4

Comparative
CE1
5.40
4.01

Example 5

Comparative
CE2
5.67
3.77

Example 6

From Table 3, it can be seen that the light-emitting devices of Examples 13 to 18 have lower driving voltage and higher luminescence efficiency at the same time than the light-emitting device of Comparative Examples 4 to 6.

It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the figures, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present disclosure as defined by the following claims, and equivalents thereof.

CONDENSED CYCLIC COMPOUND AND LIGHT-EMITTING DEVICE INCLUDING THE SAME

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