ORGANOMETALLIC COMPOUND AND LIGHT-EMITTING DEVICE INCLUDING THE SAME

An organometallic compound represented by Formula 1 emits deep blue light. A light-emitting device including the organometallic compound, and an electronic apparatus including the light-emitting device may have excellent or suitable driving voltage, luminescence efficiency, color conversion efficiency, and/or lifespan characteristics:   In Formula 1, X1 to X4 are each independently C or N, Y11 is C(Z11) or N, and Y12 is C(Z12) or N.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean Patent Application No. 10-2021-0081664, filed on Jun. 23, 2021, in the Korean Intellectual Property Office, the entire content of which is hereby incorporated by reference.

BACKGROUND

One or more aspects of embodiments of the present disclosure relate to an organometallic compound and a light-emitting device including the organometallic compound.

2. Description of the Related Art

Organic light-emitting devices are self-emissive devices that have wide viewing angles, high contrast ratios, short response times, and excellent or suitable characteristics in terms of luminance, driving voltage, and/or response speed, compared to devices in the art.

SUMMARY

One or more aspects of embodiments of the present disclosure are directed toward an organometallic compound having low driving voltage, excellent or suitable luminescence efficiency, long lifespan, and/or excellent or suitable color purity, and a light-emitting device including the same.

One or more embodiments of the present disclosure provide a light-emitting device including:

a first electrode,

a second electrode facing the first electrode, and

an interlayer located between the first electrode and the second electrode and including an emission layer,

wherein the emission layer includes:

i) a first compound, which is an organometallic compound represented by Formula 1, and

ii) a second compound including at least one π electron-deficient nitrogen-containing C1-C60cyclic group, a third compound including a group represented by Formula 3, a fourth compound to emit delayed fluorescence, or any combination thereof, and

the first compound, the second compound, the third compound, and the fourth compound are different from each other.

In Formula 1,

X1to X4may each independently be C or N,

A1to A4may each independently be a C3-C60carbocyclic group or a C1-C60heterocyclic group,

a1 to a3 may each independently be an integer from 0 to 3,

two or more neighboring groups of R1to R4, R40, Z11, Z12, Z21, and Z22may optionally be bonded to each other to form a C3-C60carbocyclic group unsubstituted or substituted with at least one R10aor a C1-C60heterocyclic group unsubstituted or substituted with at least one R10a,

b1 to b4 may each independently be an integer from 0 to 10,

when b1 is 2 or more, two or more R1(s) may be identical to or different from each other, when b2 is 2 or more, two or more R2(s) may be identical to or different from each other, when b3 is 2 or more, two or more R3(s) may be identical to or different from each other, and when b4 is 2 or more, two or more R4(s) may be identical to or different from each other,

ring CY71and ring CY72may each independently be a π electron-rich C3-C60cyclic group or a pyridine group,

X71may be a single bond or a linking group including O, S, N, B, C, Si, or any combination thereof, and

* may indicate a binding site to a neighboring atom in Formula 3.

One or more embodiments of the present disclosure provide an electronic apparatus including the light-emitting device.

One or more embodiments of the present disclosure provide the organometallic compound represented by Formula 1.

DETAILED DESCRIPTION

As used herein, the terms “use,” “using,” and “used” may be considered synonymous with the terms “utilize,” “utilizing,” and “utilized,” respectively. As used herein, expressions such as “at least one of,” “one of,” and “selected from,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.

The term “may” will be understood to refer to “one or more embodiments,” some of which include the described element and some of which exclude that element and/or include an alternate element. Similarly, alternative language such as “or” refers to “one or more embodiments,” each including a corresponding listed item.

According to an aspect, an organometallic compound may be represented by Formula 1:

In an embodiment, M may be platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), or gold (Au).

In an embodiment, M may be platinum (Pt), but embodiments of the present disclosure are not limited thereto.

In Formula 1, X1to X4may each independently be C or N.

In an embodiment, X1may be N, and X2to X4may each be C, but embodiments of the present disclosure are not limited thereto.

In an embodiment, the bond between X1and M, the bond between X2and M, and the bond between X3and M may each be a covalent bond, and the bond between X4and M may be a coordinate bond, but embodiments of the present disclosure are not limited thereto.

In Formula 1, Y11may be C(Z11) or N, and Y12may be C(Z12) or N. Z11and Z12may be the same as described in the present specification.

In Formula 1, A1to A4may each independently be a C3-C60carbocyclic group or a C1-C60heterocyclic group.

In an embodiment, A1and A3may each independently be a benzene group, a pyridine group, or a pyrimidine group, and A2may be a carbazole group, but embodiments of the present disclosure are not limited thereto.

In an embodiment, A4may be a cyclohexane group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a quinoline group, an isoquinoline group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a piperazine group, a tetrahydropyrazine group, a dihydropyrazine group, a hexahydropyridazine group, a tetrahydropyridazine group, a dihydropyridazine group, a 1,2,3,4-tetrahydroisoquinoline group, a 1,2,3,4-tetrahydroquinoline group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group, but embodiments of the present disclosure are not limited thereto.

In an embodiment, a group represented by

in Formula 1 may be represented by one of Formulae A1(1) to A1(15):

X1may be the same as described in the present specification,

R11to R14may each independently be the same as described in connection with R1, wherein R11to R14are each not hydrogen, and

In an embodiment, a group represented by

in Formula 1 may be represented by one of Formulae A2(1) to A2(7):

X2and R2may each independently be the same as described in the present specification,

b26 may be an integer from 0 to 6,

b25 may be an integer from 0 to 5, and

*, *′, and *″ each indicates a binding site to a neighboring atom.

In an embodiment, a group represented by

in Formula 1 may be represented by one of Formulae A3(1) to A3(8):

X3may be the same as described in the present specification,

R31to R33may each independently be the same as described in connection with R3, wherein R31to R33are each not hydrogen, and

*, *′, and *″ each indicates a binding site to a neighboring atom.

In an embodiment, a group represented by

in Formula 1 may be represented by one of Formulae A4(1) to A4(8):

R4may be the same as described in the present specification,

b48 may be an integer from 0 to 8,

b47 may be an integer from 0 to 7, and

*′ and *″ each indicates a binding site to a neighboring atom.

In Formula 1, L1to L3may each independently be a single bond, a double bond, *—N(Z21)—*′, *—B(Z21)—*′, *—P(Z21)—*′, *—C(Z21)(Z22)—*′, *—Si(Z21)(Z22)—*′, *—Ge(Z21)(Z22)—*′, *—S*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(Z21)═*′, *═C(Z21)—*′, *—C(Z21)═C(Z22)—*′, *—C(═S)—*′, or *—C≡C—*′. * and *′ each indicate a binding site to a neighboring atom, and Z21and Z22may each independently be the same as those described in the present specification.

In an embodiment, L1to L3may each independently be a single bond, *—C(Z21)(Z22)—*′, *—O—*′, or *—C(═O)*′.

In Formula 1, a1 to a3 may each independently be an integer from 0 to 3. a1, a2, and a3 in Formula 1 indicate numbers (e.g., the multiplicity) of L1, L2, and L3, respectively. When a1, a2, or a3 is 2 or more, the two or more L1(s), two or more L2(s), or two or more L3(s) may each be identical to or different from each other.

In an embodiment, a1 to a3 may each independently be 0 or 1, but embodiments of the present disclosure are not limited thereto.

In Formula 1, two or more neighboring groups of R1to R4, R40, Z11, Z12, Z21, and Z22may optionally be bonded to each other to form a C3-C60carbocyclic group unsubstituted or substituted with at least one R10aor a C1-C60heterocyclic group unsubstituted or substituted with at least one R10a,

—Si(Q1)(Q2)(Q3), or —B(Q1)(Q2). Q1to Q3and Q31to Q33may each independently be the same as described in the present specification.

In an embodiment, R1to R4, R40, Z11, Z12, Z21, and Z22may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a group represented by one of Formulae 9-1 to 9-20, a group represented by one of Formulae 10-1 to 10-254, —Si(Q1)(Q2)(Q3), or —B(Q1)(Q2). Q1to Q3may each independently be the same as described in the present specification:

wherein, in Formulae 9-1 to 9-20 and Formulae 10-1 to 10-254,

* indicates a binding site to a neighboring atom, D is deuterium, Ph is a phenyl group, and TMS is a trimethylsilyl group.

In an embodiment, the organometallic compound represented by Formula 1 may be selected from among Compounds 1 to 98:

In an embodiment, the organometallic compound represented by Formula 1 may be to emit blue light having a maximum emission wavelength of about 450 nm or more and about 500 nm or less.

In an embodiment, the organometallic compound represented by Formula 1 may have a lowest excitation triplet energy level of about 2.5 eV or more and about 2.8 eV or less.

In an embodiment, the organometallic compound represented by Formula 1 may satisfy at least one of Conditions 1 to 3:

LUMO energy level of the first compound>−1.50 eV  Condition 1

Absolute value of difference between LUMO energy level and HOMO energy level of the first compound>3.40 eV  Condition 2

Energy level of3MC state of the first compound>0.45 kcal/mol;  Condition 3

wherein the highest occupied molecular orbital (HOMO) energy level and the lowest unoccupied molecular orbital (LUMO) energy level of the first compound may each be measured by differential pulse voltammetry, and the energy level of the triplet metal centered (3MC) state of the first compound may be evaluated utilizing a density functional theory (DFT) method. The HOMO energy level and the LUMO energy level of the first compound may each be a negative value.

The organometallic compound represented by Formula 1 includes a core structure including the A4moiety. Accordingly, a binding force between M and X4may be increased, the rigidity (e.g., planar rigidity) of the structure may be increased, and the stability of the organometallic compound may thus be improved. For example, an energy level of a3MC of the organometallic compound and an energy level of a triplet metal-to-ligand charge transfer state (3MLCT) of the organometallic compound may be improved (e.g., may become more favorable for emission), and thus, the organometallic compound may have long lifespan effects. Therefore, an electronic device, for example, an organic light-emitting device, including the organometallic compound may have low driving voltage, excellent or suitable luminescence efficiency, long lifespan, and excellent or suitable color purity, and thus, may be utilized in the manufacture of a high-quality electronic apparatus.

Methods of synthesizing the organometallic compound represented by Formula 1 may be easily understood by those of ordinary skill in the art by referring to Synthesis Examples and Examples described herein.

At least one organometallic compound represented by Formula 1 may be utilized in a light-emitting device (for example, an organic light-emitting device). Therefore, provided is a light-emitting device including: a first electrode; a second electrode facing the first electrode; and an interlayer located between the first electrode and the second electrode and including an emission layer, wherein the interlayer includes the organometallic compound represented by Formula 1 as described in the present specification.

In an embodiment,

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 a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,

In an embodiment, the organometallic compound may be included between the first electrode and the second electrode of the light-emitting device. Therefore, the organometallic compound may be included in the interlayer of the light-emitting device, for example, in the emission layer of the interlayer.

In an embodiment, the interlayer in the light-emitting device may include:

i) a first compound, which is the organometallic compound represented by Formula 1; and

ii) a second compound including at least one π electron-deficient nitrogen-containing C1-C60cyclic group, a third compound including a group represented by Formula 3, a fourth compound to emit (e.g., capable of emitting) delayed fluorescence, or any combination thereof, and

the first compound, the second compound, the third compound, and the fourth compound may be different from each other:

ring CY71and ring CY72may each independently be a π electron-rich C3-C60cyclic group or a pyridine group,

X71is a single bond or a linking group including O, S, N, B, C, Si, or any combination thereof, and

* indicates a binding site to a neighboring atom in Formula 3.

Description of First Compound to Fourth Compound

The second compound may include a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or any combination thereof. For example, the at least one π electron-deficient nitrogen-containing C1-C60cyclic group in the second compound may be a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or any combination thereof.

In an embodiment, the light-emitting device may further include at least one of the second compound and the third compound, in addition to the first compound.

In an embodiment, the light-emitting device may further include the fourth compound, in addition to the first compound.

In an embodiment, the light-emitting device may include all of the first compound to the fourth compound.

In an embodiment, the interlayer may include the second compound. The interlayer may further include the third compound, the fourth compound, or a combination thereof, in addition to the first compound and the second compound.

In an embodiment, a difference between a triplet energy level and a singlet energy level of the fourth compound may be about 0 eV or more and about 0.5 eV or less (or about 0 eV or more and about 0.3 eV or less).

In an embodiment, the fourth compound may include at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.

In an embodiment, the fourth compound may be a C8-C60polycyclic group-containing compound in which two or more cyclic groups are condensed while sharing boron (B) (e.g., two or more rings are condensed with a B atom therebetween).

In an embodiment, the fourth compound may include a condensed cyclic ring moiety, in which at least one third ring is condensed with at least one fourth ring,

the third ring may be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclopentene group, a cyclohexene group, a cycloheptane group, a cyclooctene group, an adamantane group, a norbornene group, a norbornane group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, and

the fourth ring may be a 1,2-azaborinine group, a 1,3-azaborinine group, a 1,4-azaborinine group, a 1,2-dihydro-1,2-azaborinine group, a 1,4-oxaborinine group, a 1,4-thiaborinine group, or a 1,4-dihydroborinine group.

In In an embodiment, the interlayer may include the fourth compound. The interlayer may further include the second compound, the third compound, or a combination thereof, in addition to the first compound and the fourth compound.

In an embodiment, the interlayer may include the third compound.

The emission layer in the interlayer may include: i) the first compound; and ii) the second compound, the third compound, the fourth compound, or any combination thereof.

The emission layer may be to emit phosphorescent or fluorescent light emitted from the first compound. In an embodiment, the phosphorescent or fluorescent light emitted from the first compound may be blue light.

In an embodiment, the emission layer of the light-emitting device may include the first compound and the second compound, and the first compound and the second compound may form an exciplex.

In an embodiment, the emission layer of the light-emitting device may include the first compound, the second compound, and the third compound, and the first compound and the second compound may form an exciplex.

In an embodiment, the emission layer of the light-emitting device may include the first compound and the fourth compound, and the fourth compound may facilitate improvements in color purity, luminescence efficiency, and/or lifespan characteristics of the light-emitting device.

In an embodiment, the second compound may include a compound represented by Formula 2:

L51to L53may each independently be a single bond, a C3-C60carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60heterocyclic group unsubstituted or substituted with at least one R10a,

b51 to b53 may each independently be an integer from 1 to 5,

X54may be N or C(R54), X55may be N or C(R55), X56may be N or C(R56), and at least one of X54to X56may be N,

R51to R56may each independently be the same as described in the present specification, and

R10ais the same as described in the present specification.

In an embodiment, the third compound may include a compound represented by Formula 3-1, a compound represented by Formula 3-2, a compound represented by Formula 3-3, a compound represented by Formula 3-4, a compound represented by Formula 3-5, or any combination thereof:

ring CY71to ring CY74may each independently be a π electron-rich C3-C60cyclic group or a pyridine group,

X85may be C or Si,

L81to L85may each independently be a single bond, *—C(Q4)(Q5)-*′, *—Si(Q4)(Q5)-*′, a π electron-rich C3-C60cyclic group unsubstituted or substituted with at least one R10a, or a pyridine group unsubstituted or substituted with at least one R10a, wherein Q4and Q5may each independently be the same as described in connection with Q1,

b81 to b85 may each independently be an integer from 1 to 5,

R71to R74, R81to R85, R82a, R82b, R83a, R83b, R84a, and R84bmay each independently be the same as described in the present specification,

a71 to a74 may each independently be an integer from 0 to 20, and

R10amay be the same as described in the present specification.

In an embodiment, the fourth compound may include a compound represented by Formula 502, a compound represented by Formula 503, or a combination thereof:

ring A501to ring A504may each independently be a C3-C60carbocyclic group or a C1-C60heterocyclic group,

a501 to a504 may each independently be an integer from 0 to 20, and

R10ais the same as described in the present specification.

Description of Formulae 2, 3-1 to 3-5, 502, and 503

b51 to b53 in Formula 2 indicate numbers of L51to L53, respectively, and may each be an integer from 1 to 5. When b51 is 2 or more, two or more L51(s) may be identical to or different from each other, when b52 is 2 or more, two or more L52(s) may be identical to or different from each other, and when b53 is 2 or more, two or more L53(s) may be identical to or different from each other. In an embodiment, b51 to b53 may each independently be 1 or 2.

a single bond; or

In an embodiment, in Formula 2, the bond between L51and R51, the bond between L52and R52, the bond between L53and R53, the bond between two or more L51(s), the bond between two or more L52(s), the bond between two or more L53(s), the bond between L51and the carbon atom between X54and X55in Formula 2, the bond between L52and the carbon atom between X54and X56in Formula 2, and the bond between L53and the carbon atom between X55and X56in Formula 2 may each be a “carbon-carbon single bond”.

In Formula 2, X54may be N or C(R54), X55may be N or C(R55), X56may be N or C(R56), and at least one of X54to X56may be N. R54to R56may each independently be the same as described in the present specification. In an embodiment, two or three of X54to X56may be N.

R51to R56, R71to R74, R81to R85, R82a, R82b, R83a, R83b, R84a, R84b, R500a, R500b, R501to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508bin the present specification may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60alkyl group unsubstituted or substituted with at least one R10a, a C2-C60alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60arylthio group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2). Q1to Q3may each independently be the same as described in the present specification.

ring CY91and ring CY92may each independently be a C5-C30carbocyclic group that is unsubstituted or substituted with at least one R10aor a C1-C30heterocyclic group that is unsubstituted or substituted with at least one R10a,

R91, R91a, and R91bmay each independently be the same as described in connection with R82, R82a, and R82bin the present specification,

R10ais the same as described in the present specification, and

* indicates a binding site to a neighboring atom.

In an embodiment, in Formula 91,

ring CY91and ring CY92may each independently be a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group, each unsubstituted or substituted with at least one R10a,

hydrogen or a C1-C10alkyl group; or

a phenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, each unsubstituted or substituted with deuterium, a C1-C10alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof.

In Formulae 3-1 to 3-5, 502, and 503, a71 to a74 and a501 to a504 may respectively indicate the number of R71(s) to R74(s) and R501(s) to R504(s), and a71 to a74 and a501 to a504 may each independently be an integer from 0 to 20. When a71 is 2 or greater, at least two R71(s) may be identical to or different from each other, when a72 is 2 or greater, at least two R72(s) may be identical to or different from each other, when a73 is 2 or greater, at least two R73(s) may be identical to or different from each other, when a74 is 2 or greater, at least two R74(s) may be identical to or different from each other, when a501 is 2 or greater, at least two R501(s) may be identical to or different from each other, when a502 is 2 or greater, at least two R502(s) may be identical to or different from each other, when a503 is 2 or greater, at least two R503(s) may be identical to or different from each other, and when a504 is 2 or greater, at least two R504(s) may be identical to or different from each other. a71 to a74 and a501 to a504 may each independently be an integer from 0 to 8.

In an embodiment, a group represented by *-(L51)b51-R51and a group represented by *-(L52)b52-R52in Formula 2 may each not be a phenyl group.

In an embodiment, a group represented by *-(L51)b51-R51and a group represented by *-(L52)b52-R52in Formula 2 may be identical to each other.

In an embodiment, a group represented by *-(L51)b51-R51and a group represented by *-(L52)b52-R52in Formula 2 may be different from each other.

In an embodiment, b51 and b52 in Formula 2 may each be 1, 2, or 3, and L51and L52may each independently be a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, each unsubstituted or substituted with at least one R10a.

In an embodiment, R51and R52in Formula 2 may each independently be a C3-C60carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60arylthio group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), or —Si(Q1)(Q2)(Q3), and

wherein Q1to Q3may each independently be 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 an embodiment,

a group represented by *-(L51)b51-R51in Formula 2 may be a group represented by one of Formulae CY51-1 to CY51-26, and/or

a group represented by *-(L52)b52-R52in Formula 2 may be a group represented by one of Formulae CY52-1 to CY52-26, and/or

a group represented by *-(L53)b53-R53in Formula 2 may be a group represented by one of Formulae CY53-1 to CY53-27, —C(Q1)(Q2)(Q3), or —Si(Q1)(Q2)(Q3).

wherein, in Formulae CY51-1 to CY51-26, CY52-1 to CY52-26, and CY53-1 to CY53-27,

in some embodiments, Y63and Y64in Formulae CY51-16 and CY51-17 may not simultaneously be a single bond,

in some embodiments, Y67and Y68in Formulae CY52-16 and CY52-17 may not simultaneously be a single bond,

R51ato R51e, R61to R64, R63a, R63b, R64a, and R64bmay each be understood by referring to the description of R51, and R51ato R51emay not each be (e.g., may not simultaneously be) hydrogen,

R52ato R52e, R65to R68, R67a, R67b, R68a, and R68bmay each be understood by referring to the description of R52, and R52ato R52emay not each be hydrogen,

R53ato R53e, R69a, and R69bmay each be understood by referring to the description of R53, and R53ato R53emay not each be (e.g., may not simultaneously be) hydrogen, and

* indicates a binding site to a neighboring atom.

In an embodiment,

wherein Q1to Q3may each independently be a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, each unsubstituted or substituted with deuterium, a C1-C10alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof,

in Formulae CY51-16 and CY51-17, i) Y63may be O or S and Y64may be Si(R64a)(R64b), or ii) Y63may be Si(R63a)(R63b) and Y64may be O or S, and

in Formulae CY52-16 and CY52-17, i) Y67may be O or S, and Y68may be Si(R68a)(R68b), or ii) Y67may be Si(R67a)(R67b), and Y68may be O or S.

a single bond; or

*—C(Q4)(Q5)-*′ or *—Si(Q4)(Q5)-*′; or

In an embodiment, in Formulae 3-1 and 3-2, a group represented by

may be represented by one of Formulae CY71-1(1) to CY71-1(8),

in Formulae 3-1 and 3-3, a group represented by

may be represented by one of Formulae CY71-2(1) to CY71-2(8),

in Formulae 3-2 and 3-4, a group represented by

may be represented by one of Formulae CY71-3(1) to CY71-3(32),

in Formulae 3-3 to 3-5, a group represented by

may be represented by one of Formulae CY71-4(1) to CY71-4(32), and/or

in Formula 3-5, a group represented by may be represented by

may be represented by one of Formulae CY71-5(1) to CY71-5(8):

X81to X85, L81, b81, R81, and R85may each independently be the same as described in the present specification,

in Formulae CY71-1(1) to CY71-1(8) and CY71-4(1) to CY71-4(32), X86and X87may not be a single bond at the same time (e.g., simultaneously),

in Formulae CY71-2(1) to CY71-2(8), CY71-3(1) to CY71-3(32), and CY71-5(1) to CY71-5(8), X88and X89may not be a single bond at the same time (e.g., simultaneously), and

R86to R89, R86a, R86b, R87a, R87b, R88a, R88b, R89a, and R89bmay each independently be the same as described in connection with R81in the present specification.

Examples of Second Compound, Third Compound, and Fourth Compound

In an embodiment, the second compound may include at least one of Compounds ETH1 to ETH84:

In an embodiment, the third compound may include at least one of Compounds HTH1 to HTH52-.

In an embodiment, the fourth compound may include at least one of Compounds DFD1 to DFD14:

In the compounds described, Ph represents a phenyl group, D5represents substitution with five deuterium, and D4represents substitution with four deuterium. For example, a group represented by

may be identical to a group represented by

In an embodiment, the light-emitting device may satisfy at least one of Condition 1 to Condition 3:

LUMO energy level of the first compound>−1.50 eV  Condition 1

Absolute value of difference between LUMO energy level and HOMO energy level of the first compound≥3.40 eV  Condition 2

Energy level of3MC state of the first compound>0.45 kcal/mol  Condition 3

wherein the HOMO energy level and the LUMO energy level of the first compound may each be measured by differential pulse voltammetry, and the energy level of a3MC state of the first compound may be evaluated utilizing a DFT method. The HOMO energy level and the LUMO energy level of the first compound may each be a negative value.

In an embodiment, the light-emitting device may satisfy at least one of Condition A to Condition D:

LUMO energy level of the third compound>LUMO energy level of the first compound  Condition A

LUMO energy level of the first compound>LUMO energy level of the second compound  Condition B

HOMO energy level of the first compound>HOMO energy level of the third compound  Condition C

HOMO energy level of the third compound>HOMO energy level of the second compound  Condition D

wherein the HOMO energy levels and the LUMO energy levels of the first compound, the second, compound, and the third compound may each be a negative value, and may be measured according to any suitable method, for example, a method described in Evaluation Example 1 in the present specification.

In an embodiment, the absolute value of a difference between the LUMO energy level of the first compound and the LUMO energy level of the second compound may be about 0.1 eV or higher and about 1.0 eV or lower, the absolute value of a difference between the LUMO energy level of the first compound and the LUMO energy level of the third compound may be about 0.1 eV or higher and about 1.0 eV or lower, the absolute value of a difference between the HOMO energy level of the first compound and the HOMO energy level of the second compound may be about 1.25 eV or lower (e.g., about 1.25 eV or lower and about 0.2 eV or higher), and the absolute value of a difference between the HOMO energy level of the first compound and the HOMO energy level of the third compound may be about 1.25 eV or lower (e.g., about 1.25 eV or lower and about 0.2 eV or higher).

When the relationships between LUMO energy level and HOMO energy level satisfy the conditions described above, a suitable balance between holes and electrons injected into the emission layer can be obtained.

The light-emitting device may have a structure of a first embodiment or a second embodiment, as described below.

Descriptions of First Embodiment

According to the first embodiment, the first compound may be included in an emission layer in an interlayer of a light-emitting device, wherein the emission layer may further include a host, the first compound may be different from the host, and the emission layer may be to emit phosphorescent or fluorescent light emitted from the first compound. For example, according to the first embodiment, the first compound may be a dopant or an emitter. In an embodiment, the first compound may be a phosphorescent dopant or a phosphorescence emitter.

The phosphorescent or fluorescent light to be emitted from the first compound may be blue light.

The emission layer may further include an auxiliary dopant. The auxiliary dopant may serve to improve luminescence efficiency from the first compound by effectively transferring a dopant or the first compound as an emitter.

The auxiliary dopant may be different from the first compound and the host.

In an embodiment, the auxiliary dopant may be a delayed fluorescence-emitting compound.

In an embodiment, the auxiliary dopant may be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.

Descriptions of Second Embodiment

According to the second embodiment, the first compound may be included in an emission layer in an interlayer of a light-emitting device, wherein the emission layer may further include a host and a dopant, the first compound may be different from the host and the dopant (e.g., the first compound is not the host or the dopant), and the emission layer may be to emit phosphorescent or fluorescent light (e.g., delayed fluorescence light) via the dopant.

For example, the first compound in the second embodiment may serve as an auxiliary dopant to transfer energy to a dopant (or an emitter), and is not the dopant (e.g., is not the main dopant).

In an embodiment, the first compound in the second embodiment may serve as an emitter and as an auxiliary dopant to transfer energy to a dopant (or an emitter).

For example, phosphorescent or fluorescent light to be emitted from the dopant (or the emitter) in the second embodiment may be blue phosphorescent light or blue fluorescent light (e.g., blue delayed fluorescence light).

The dopant (or the emitter) in the second embodiment may be a phosphorescent dopant material (e.g., the organometallic compound represented by Formula 1, the organometallic compound represented by Formula 401, or any combination thereof) or any fluorescent dopant material (e.g., the compound represented by Formula 501, the compound represented by Formula 502, the compound represented by Formula 503, or any combination thereof).

In the first embodiment and the second embodiment, the blue light may be blue light having a maximum emission wavelength in a range of about 390 nm to about 500 nm, about 410 nm to about 490 nm, about 430 nm to about 480 nm, about 440 nm to about 475 nm, or about 455 nm to about 470 nm.

The auxiliary dopant in the first embodiment may include, for example, the fourth compound represented by Formula 502 or Formula 503.

The host in the first embodiment and the second embodiment may be any host material (e.g., the compound represented by Formula 301, the compound represented by 301-1, the compound represented by Formula 301-2, or any combination thereof).

In an embodiment, the host in the first embodiment and the second embodiment may be the second compound, the third compound, or any combination thereof.

In an embodiment, the light-emitting device may include a capping layer located outside the first electrode and/or outside the second electrode.

In an embodiment, the light-emitting device may further include at least one of a first capping layer located outside the first electrode and a second capping layer located outside the second electrode, and the organometallic compound represented by Formula 1 may be included in at least one of the first capping layer or the second capping layer. The first capping layer and/or second capping layer may each independently be the same as described in the present specification.

In an embodiment, the light-emitting device may further include:

a first capping layer located outside the first electrode and including the organometallic compound represented by Formula 1;

a second capping layer located outside the second electrode and including the organometallic compound represented by Formula 1; or

the first capping layer and the second capping layer, each optionally including the organometallic compound represented by Formula 1.

The wording “(interlayer and/or capping layer) includes an (the) organometallic compound” as utilized herein may be to mean that the (interlayer and/or capping layer) may include one kind of organometallic compound represented by Formula 1 or two different kinds of organometallic compounds, each represented by Formula 1.

For example, the interlayer and/or capping layer may include Compound 1 only as the organometallic compound. In this regard, Compound 1 may be present in the emission layer of the light-emitting device. In an embodiment, the interlayer may include, as the organometallic compound, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may be present in the same layer (for example, all of Compound 1 and Compound 2 may be present in the emission layer), or may be present in different layers (for example, Compound 1 may be present in the emission layer, and Compound 2 may be present in the electron transport region).

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

According to another aspect, provided is an electronic apparatus including the light-emitting device. The electronic apparatus may further include a thin-film transistor. For example, the electronic apparatus may further include a thin-film transistor including a source electrode and a drain electrode, wherein the first electrode of the light-emitting device may be electrically connected 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. The electronic apparatus may be the same as described in the present specification.

Description of FIG.1

FIG.1is a schematic cross-sectional view of a light-emitting device10according to an embodiment of the disclosure. The light-emitting device10includes a first electrode110, an interlayer130, and a second electrode150.

Hereinafter, a structure of the light-emitting device10according to an embodiment and a method of manufacturing the light-emitting device10will be described in connection withFIG.1.

First Electrode110

InFIG.1, a substrate may be additionally located under the first electrode110and/or above the second electrode150. As the substrate, a glass substrate or a plastic substrate may be utilized. In an embodiment, the substrate may be a flexible substrate, and may include plastics with excellent or suitable heat resistance and durability (such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof).

The first electrode110may be formed by, for example, depositing or sputtering a material for forming the first electrode110on the substrate. When the first electrode110is an anode, a material for forming the first electrode110may be a high work function material to facilitate injection of holes.

The first electrode110may have a single-layered structure including (e.g., consisting of) a single layer or a multilayer structure including a plurality of layers. In an embodiment, the first electrode110may have a three-layered structure of ITO/Ag/ITO.

The interlayer130may be located on the first electrode110. The interlayer130may include an emission layer.

The interlayer130may further include a hole transport region between the first electrode110and the emission layer and an electron transport region between the emission layer and the second electrode150.

The interlayer130may 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 an embodiment, the interlayer130may include: i) two or more emitting units sequentially stacked between the first electrode110and the second electrode150, and ii) a charge generation layer located between the two or more emitting units. When the interlayer130includes emitting units and a charge generation layer as described above, the light-emitting device10may be a tandem light-emitting device.

Hole Transport Region in Interlayer130

For example, the hole transport area may have a multi-layer 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, the layers of each structure being stacked sequentially from the first electrode110.

L205may be *—O—*′, *—S—*′, *—N(Q201)-*′, a C1-C20alkylene group unsubstituted or substituted with at least one R10a, a C2-C20alkenylene group unsubstituted or substituted with at least one R10a, a C3-C60carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60heterocyclic group unsubstituted or substituted with at least one R10a,

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 R10a, or a C1-C6heterocyclic group unsubstituted or substituted with at least one R10a,

R201and R202may optionally be linked to each other via a single bond, a C1-C5alkylene group unsubstituted or substituted with at least one R10a, or a C2-C5alkenylene group unsubstituted or substituted with at least one R10a, to form a C8-C60polycyclic group (for example, a carbazole group and/or the like), which may be unsubstituted or substituted with at least one R10a(for example, 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 R10a, or a C2-C5alkenylene group unsubstituted or substituted with at least one R10a, to form a C8-C60polycyclic group that may be unsubstituted or substituted with at least one R10a, and

na1 may be an integer from 1 to 4.

In an embodiment, each of Formulae 201 and 202 may include at least one of groups represented by Formulae CY201 to CY217.

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, each of Formulae 201 and 202 may include at least one of the groups represented by Formulae CY201 to CY203.

In an embodiment, Formula 201 may include at least one of the groups represented by Formulae CY201 to CY203 and at least one of the groups represented by Formulae CY204 to CY217.

In an embodiment, xa1 in Formula 201 may be 1, R201may be a group represented by one of Formulae CY201 to CY203, xa2 may be 0, and R202may be a group represented by one of Formulae CY204 to CY207.

In an embodiment, each of Formulae 201 and 202 may not include (e.g., may exclude) groups represented by Formulae CY201 to CY203.

In an embodiment, each of Formulae 201 and 202 may not include (e.g., may exclude) groups represented by Formulae CY201 to CY203, and may include at least one of groups represented by Formulae CY204 to CY217.

In an embodiment, each of Formulae 201 and 202 may not include (e.g., may exclude) groups represented by Formulae CY201 to CY217.

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

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

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

Examples of the quinone derivative may include TCNQ, F4-TCNQ, and/or the like.

Examples of the cyano group-containing compound may include HAT-CN, a compound represented by Formula 221, and/or the like.

In Formula 221,

R221to R223may each independently be a C3-C60carbocyclic group unsubstituted or substituted with at least one R10aor a C1-C6heterocyclic group unsubstituted or substituted with at least one R10a, and

at least one of 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.

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

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

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

Examples of the metal halide may include an alkali metal halide, an alkaline earth metal halide, a transition metal halide, a post-transition metal halide, and/or a lanthanide metal halide.

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

Emission Layer in Interlayer130

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

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

In an embodiment, the emission layer may include a quantum dot.

In an embodiment, the emission layer may include a delayed fluorescence material. The delayed fluorescence material may act as a host or as a dopant in the emission layer.

The host in the emission layer may include the second compound or the third compound described in the present specification, or any combination thereof.

The host may include a compound represented by Formula 301:

xb1 may be an integer from 0 to 5,

R301may be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60alkyl group unsubstituted or substituted with at least one R10a, a C2-C60alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60heterocyclic group unsubstituted or substituted with at least one R10a, —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, and

Q301to Q303may each independently be the same as described in connection with Q1.

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

xb22 and xb23 may each independently be 0, 1, or 2,

L301, xb1, and R301may each independently be the same as described in the present specification,

L302to L304may each independently be 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 R314may each independently be the same as described in connection with R301.

In an embodiment, the host may include an alkali earth metal complex, a post-transition metal complex, or a combination thereof. In an embodiment, the host may include a Be complex (for example, Compound H55), an Mg complex, a Zn complex, or a combination thereof.

In an embodiment, the host may include a silicon-containing compound, a phosphine oxide-containing compound, or any combination thereof.

The host may have various suitable modifications, For example, the host may include only one kind of compound, or may include two or more kinds of different compounds.

The emission layer may include the first compound as described in the present specification, as a phosphorescent dopant.

In an embodiment, when the emission layer includes the first compound as described in the present specification and the first compound serves as an auxiliary dopant, the emission layer may include a phosphorescent dopant.

The phosphorescent dopant may include at least one transition metal as a central metal.

The phosphorescent dopant may be electrically neutral.

In an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 401:

L401may be a ligand represented by Formula 402, and xc1 may be 1, 2, or 3, wherein, when xc1 is two or more, two or more L401(s) may be identical to or different from each other,

L402may be an organic ligand, and xc2 may be 0, 1, 2, 3, or 4, wherein, when xc2 is 2 or more, two or more L402(s) may be identical to or different from each other,

X401and X402may each independently be nitrogen or carbon,

ring A401and ring A402may each independently be a C3-C60carbocyclic group or a C1-C60heterocyclic group,

Q411to Q414may each independently be the same as described in connection with Q1,

R401and R402may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20alkyl group unsubstituted or substituted with at least one R10a, a C1-C20alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60heterocyclic group unsubstituted or substituted with at least one R10a, —Si(Q401)(Q402)(Q403), —N(Q401)(Q402), —B(Q401)(Q402), —C(═O)(Q401), —S(═O)2(Q401), or —P(═O)(Q401)(Q402),

Q401to Q403may each independently be the same as described in connection with Q1,

In an embodiment, in Formula 402, i) X401may be nitrogen, and X402may be carbon, or ii) each of X401and X402may be nitrogen.

In an embodiment, when xc1 in Formula 402 is 2 or more, two ring A401in two or more L401(s) may be optionally linked to each other via T402, which is a linking group, and two ring A402may optionally be linked to each other via T403, which is a linking group (see Compounds PD1 to PD4 and PD7). T402and T403may each independently be the same as described in connection with T401.

L402in Formula 401 may be an organic ligand. In an embodiment, L402may include a halogen group, a diketone group (for example, an acetylacetonate group), a carboxylic acid group (for example, a picolinate group), —C(═O), an isonitrile group, —CN group, a phosphorus group (for example, a phosphine group, a phosphite group, etc.), or any combination thereof.

The phosphorescent dopant may include, for example, one of compounds PD1 to PD39, or any combination thereof:

Fluorescent Dopant

When the emission layer includes the first compound as described in the present specification and the first compound serves as an auxiliary dopant, the emission layer may further include a fluorescent dopant.

In an embodiment, when the emission layer includes the first compound as described in the present specification and the first compound serves as a phosphorescent dopant, the emission layer may further include an auxiliary dopant.

The fluorescent dopant and the auxiliary dopant may each independently include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.

In an embodiment, the fluorescent dopant and the auxiliary dopant may each independently include a compound represented by Formula 501:

xd1 to xd3 may each independently be 0, 1, 2, or 3, and

In an embodiment, Ar501in Formula 501 may be a condensed cyclic group (for example, an anthracene group, a chrysene group, or a pyrene group) in which three or more monocyclic groups are condensed together.

In an embodiment, xd4 in Formula 501 may be 2.

In an embodiment, the fluorescent dopant and the auxiliary dopant may each independently include one of Compounds FD1 to FD36, DPVBi, DPAVBi, or any combination thereof:

In an embodiment, the fluorescent dopant and the auxiliary dopant may each independently include the fourth compound represented by Formula 502 or 503 as described in the present specification.

Delayed Fluorescence Material

The emission layer may include the fourth compound as described in the present specification, as a delayed fluorescence material.

In an embodiment, the emission layer may include the fourth compound, and may further include a delayed fluorescence material.

In the present specification, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.

The delayed fluorescence material included in the emission layer may act as a host or a dopant, depending on the type or kind of other materials included in the emission layer.

In an embodiment, the difference between the triplet energy level of the delayed fluorescence material and the singlet energy level of the delayed fluorescence material may be greater than or equal to 0 eV and less than or equal to 0.5 eV. When the difference between the triplet energy level of the delayed fluorescence material and the singlet energy level of the delayed fluorescence material satisfies the above-described range, up-conversion from the triplet state to the singlet state of the delayed fluorescence materials may effectively occur, and thus, the luminescence efficiency of the light-emitting device10may be improved.

In an embodiment, the delayed fluorescence material may include i) a material including 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), and ii) a material including a C8-C60polycyclic group in which two or more cyclic groups are condensed while sharing boron (B).

Examples of the delayed fluorescence material may include at least one of Compounds DF1 to DF9:

Quantum Dot

The emission layer may include a quantum dot.

In the present specification, a quantum dot refers to a crystal of a semiconductor compound, and may include any material capable of emitting light of one or more suitable emission wavelengths according to the size of the crystal.

The quantum dot may be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar thereto.

According to the wet chemical process, a precursor material is mixed with an organic solvent to grow a quantum dot particle crystal. As the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal so that the growth of quantum dot particles can be controlled or modulated. Such a process is more easily performed than vapor deposition methods (such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE)), and has a lower cost.

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

The Group IV element or compound may include: a single element compound (such as Si or Ge); a binary compound (such as SiC or SiGe); or any combination thereof.

Each element included in a multi-element compound (such as the binary compound, ternary compound and/or quaternary compound), may be present in a particle with a substantially uniform concentration (e.g., distribution) or non-uniform concentration.

In an embodiment, the quantum dot may have a single structure or a dual core-shell structure. In the case of the quantum dot having a single structure, the concentration of each element included in the corresponding quantum dot may be substantially uniform. In an embodiment, the material contained in the core and the material contained in the shell may be different from each other.

The shell of the quantum dot may act as a protective layer to prevent or reduce chemical degeneration of the core to maintain semiconductor characteristics and/or as a charging layer to impart electrophoretic characteristics to the quantum dot. The shell may be a single layer or a multi-layer. The element present at or within the interface between the core and the shell of the quantum dot may have a concentration gradient that decreases toward the center of the quantum dot.

Examples of the material forming the shell of the quantum dot may be an oxide of metal, metalloid, or non-metal, a semiconductor compound, and any combination thereof. Examples of the oxide of metal, metalloid, or non-metal may include: a binary compound (such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and/or NiO); a ternary compound (such as MgAl2O4, CoFe2O4, NiFe2O4, and/or CoMn2O4); or any combination thereof. Examples of the semiconductor compound may include, as described herein, 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, or any combination thereof. In some embodiments, 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, and within these ranges, color purity or color reproducibility may be increased. In some embodiments, because the light emitted through the quantum dot is emitted in all directions, the wide viewing angle can be improved.

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

Because the energy band gap can be adjusted by controlling the size of the quantum dot, light having one or more suitable wavelength bands can be obtained from the quantum dot emission layer. Therefore, by utilizing quantum dots of different sizes, a light-emitting device that emits light of one or more suitable wavelengths may be implemented. In an embodiment, the size of the quantum dot(s) may be selected to emit red, green and/or blue light. In some embodiments, the size of the quantum dot(s) may be configured to emit white light by combining light of one or more suitable colors.

Electron Transport Region in Interlayer130

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

For example, the electron transport area 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, the constituting layers of each structure being sequentially stacked from an emission layer.

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

Ar601and L601may each independently be a C3-C60carbocyclic group unsubstituted or substituted with at least one R10aor a C1-C6heterocyclic group unsubstituted or substituted with at least one R10a,

R601may be a C3-C60carbocyclic group unsubstituted or substituted with at least one R10a, 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 Q603may each independently be the same as described in connection with Q1,

at least one of Ar601, L601, and R601may each independently be a π electron-deficient nitrogen-containing C1-C60cyclic group unsubstituted or substituted with at least one R10a.

In an embodiment, when xe11 in Formula 601 is 2 or more, two or more Ar601(s) may be linked via a single bond.

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

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

L611to L613may each independently be the same as described in connection with L601,

xe611 to xe613 may each independently be the same as described in connection with xe1,

R611to R613may each independently be the same as described 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 R10a, or a C1-C60heterocyclic group unsubstituted or substituted with at least one R10a.

The electron transport region may include an electron injection layer to facilitate the injection of electrons from the second electrode150. The electron injection layer may be in direct contact with the second electrode150.

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

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

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

The second electrode150may be located on the interlayer130having such a structure. The second electrode150may be a cathode, which is an electron injection electrode, and as the material for the second electrode150, a metal, an alloy, an electrically conductive compound, or any combination thereof, each having a low work function, may be utilized.

The second electrode150may 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 electrode110, and/or a second capping layer may be located outside the second electrode150. In detail, the light-emitting device10may have a structure in which the first capping layer, the first electrode110, the interlayer130, and the second electrode150are sequentially stacked in this stated order, a structure in which the first electrode110, the interlayer130, the second electrode150, and the second capping layer are sequentially stacked in this stated order, or a structure in which the first capping layer, the first electrode110, the interlayer130, the second electrode150, and the second capping layer are sequentially stacked in this stated order.

Light generated in an emission layer of the interlayer130of the light-emitting device10may be extracted toward the outside through the first electrode110(which is a semi-transmissive electrode or a transmissive electrode) and the first capping layer, or light generated in an emission layer of the interlayer130of the light-emitting device10may be extracted toward the outside through the second electrode150(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 emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device10is increased, so that the emission efficiency of the light-emitting device10may be improved.

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

At least one of the first capping layer or the second capping layer may each independently include carbocyclic compounds, heterocyclic compounds, amine group-containing compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, alkaline earth metal complexes, or any 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 of the first capping layer or the second capping layer may each independently include an amine group-containing compound.

In an embodiment, at least one of the first capping layer or the second capping layer may each independently include one of Compounds HT28 to HT33, one of Compounds CP1 to CP6, β-NPB, or any combination thereof:

The organometallic compound represented by Formula 1 may be included in various suitable films. According to an embodiment, a film including an organometallic compound represented by Formula 1 may be provided. The film may be, for example, an optical member (or a light control member) (for example, a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancement layer, a selective light absorbing layer, a polarizing layer, a quantum dot-containing layer, or like), a light-blocking member (for example, a light reflective layer, a light absorbing layer, and/or the like), a protective member (for example, an insulating layer, a dielectric layer, and/or the like).

Electronic Apparatus

The light-emitting device may be included in one or more 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 located in at least one traveling direction of light emitted from the light-emitting device. For example, the light emitted from the light-emitting device may be blue light 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.

A pixel-defining film may be located among the subpixel areas to define each of the subpixel areas.

The color filter may further include a plurality of color filter areas and light-shielding patterns located among the color filter areas, and the color conversion layer may include a plurality of color conversion areas and light-shielding patterns located among the color conversion areas.

The color filter areas (or the color conversion areas) may include a first area to emit first color light, a second area to emit second color light, and/or a third area to emit 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. For example, 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 (e.g., may exclude) a quantum dot. The quantum dot may be the same as described in the present specification. The first area, the second area, and/or the third area may each further include a scatterer.

In an embodiment, the light-emitting device may be to emit a first light, the first area may be to absorb the first light to emit a first first-color light, the second area may be to absorb the first light to emit a second first-color light, and the third area may be to 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 each have different maximum emission wavelengths. For example, 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 thin-film transistor may further include a gate electrode, a gate insulating film, etc.

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

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

Description of FIGS.2and3

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

The light-emitting apparatus ofFIG.2includes a substrate100, a thin-film transistor (TFT), a light-emitting device, and an encapsulation portion300that seals the light-emitting device.

A TFT may be located on the buffer layer210. The TFT may include an activation layer220, a gate electrode240, a source electrode260, and a drain electrode270.

The activation layer220may include an inorganic semiconductor (such as silicon or polysilicon), an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.

A gate insulating film230for insulating the activation layer220from the gate electrode240may be located on the activation layer220, and the gate electrode240may be located on the gate insulating film230.

The TFT is electrically connected to a light-emitting device to drive the light-emitting device, and is covered by a passivation layer280. The passivation layer280may include an inorganic insulating film, an organic insulating film, or a combination thereof. A light-emitting device is provided on the passivation layer280. The light-emitting device may include a first electrode110, an interlayer130, and a second electrode150.

The first electrode110may be formed on the passivation layer280. The passivation layer280does not completely cover the drain electrode270and exposes a portion of the drain electrode270, and the first electrode110is connected to the exposed portion of the drain electrode270.

A pixel-defining layer290containing an insulating material may be located on the first electrode110. The pixel-defining layer290exposes a region of the first electrode110, and an interlayer130may be formed in the exposed region of the first electrode110. The pixel-defining layer290may be a polyimide or polyacrylic organic film. In some embodiments, at least some layers of the interlayer130may extend beyond the upper portion of the pixel-defining layer290to be located in the form of a common layer.

The second electrode150may be located on the interlayer130, and a capping layer170may be additionally formed on the second electrode150. The capping layer170may be formed to cover the second electrode150.

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

The light-emitting apparatus ofFIG.3is the same as the light-emitting apparatus ofFIG.2, except that a light-shielding pattern500and a functional region400are additionally located on the encapsulation portion300. The functional region400may be a combination of i) a color filter area, ii) a color conversion area, 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 ofFIG.3may be a tandem light-emitting device.

Manufacture Method

Respective layers included in the hole transport region, the emission layer, and respective layers included in the electron transport region may be formed in a certain region by utilizing 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.

DEFINITION OF TERMS

The term “cyclic group” as utilized herein may include the C3-C60carbocyclic group and the C1-C60heterocyclic group.

The term “π electron-rich C3-C60cyclic group” as utilized 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 utilized herein refers to a heterocyclic group that has one to sixty carbon atoms and includes *—N═*′ as a ring-forming moiety.

In an embodiment,

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 each other, iii) a group T3 (defined below), iv) a condensed cyclic group in which two or more groups T3 are condensed 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 each other (for example, the C3-C60carbocyclic group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-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 benzothienodibenzothiophene group, etc.),

the π electron-deficient nitrogen-containing C1-C60cyclic group may be i) a group T4 (defined below), ii) a condensed cyclic group in which two or more group T4 are condensed with each other, iii) a condensed cyclic group in which at least one group T4 and at least one group T1 are condensed with each other, iv) a condensed cyclic group in which at least one group T4 and at least one group T3 are condensed 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 one another (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, an azadibenzofuran group, etc.),

The term “cyclic group”, “C3-C60carbocyclic group”, “C1-C60heterocyclic group”, “π electron-rich C3-C60cyclic group”, or “π electron-deficient nitrogen-containing C1-C60cyclic group” as utilized herein refers to a group condensed to any cyclic group or a polyvalent group (for example, a divalent group, a trivalent group, a tetravalent group, etc.), depending on the structure of a formula in connection with which the terms are utilized. In an embodiment, “a benzene group” may be a benzo group, a phenyl group, a phenylene group, and/or the like, which may be easily understood by one of ordinary skill in the art according to the structure of a formula including the “benzene group.”

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

The term “C7-C60aryl alkyl group” utilized herein refers to -A104A105(where A104may be a C1-C54alkylene group, and A105may be a C6-C59aryl group), and the term “C2-C60heteroaryl alkyl group” utilized herein refers to -A106A107(where A106may be a C1-C59alkylene group, and A107may be a C1-C59heteroaryl group).

The term “heteroatom” as utilized herein refers to any atom other than a carbon atom. Examples of the heteroatom may include O, S, N, P, Si, B, Ge, Se, and/or any combination thereof.

“Ph” as utilized herein refers to a phenyl group, “Me” as utilized herein refers to a methyl group, “Et” as utilized herein refers to an ethyl group, “tert-Bu” or “But” as utilized herein refers to a tert-butyl group, and “OMe” as utilized herein refers to a methoxy group.

The term “terphenyl group” as utilized herein refers to “a phenyl group substituted with a biphenyl group”. The “terphenyl group” is a substituted phenyl group having, as a substituent, a C6-C60aryl group substituted with a C6-C60aryl group.

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

Hereinafter, compounds according to embodiments and light-emitting devices according to embodiments will be described in more detail with reference to the following synthesis examples and examples. The wording “B was utilized instead of A,” used in describing Synthesis Examples, indicates that an identical molar equivalent of B was utilized in place of A.

EXAMPLES

Synthesis Example 1: Synthesis of Compound 1

(1) Synthesis of Intermediate Compound [1-a]

1-(5-bromo-2-nitrophenyl)-piperidine (7.3 mmol, 1.0 eq) and 8% HCl aqueous solution (60 mL) were mixed together and then heated at 80° C. to thereby obtain a solution. A SnCl2(1.2 eq) and 8% HCl aqueous solution (40 mL) mixed solution was slowly added to the solution and then stirred for 30 min at 80° C., to thereby obtain a product (e.g., an intermediate reaction product). The product was cooled to room temperature, neutralized utilizing ammonia water, and then subjected to an extraction process three times utilizing dichloromethane and water, to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and concentrated, and column chromatography was utilized to purify Intermediate Compound 1-a (yield: 80%).

(2) Synthesis of Intermediate Compound[1-b]

Intermediate Compound [1-a] (5 mmol, 1.0 eq) was dissolved in H2SO4(20 mL) to thereby obtain a solution. KNO3(1.1 eq) was dissolved in H2SO4(20 mL) and then slowly added to the solution. The mixture was stirred for an hour, neutralized utilizing ammonia water at 0° C., washed utilizing water, and then subjected to filtration, to thereby obtain Intermediate Compound 1-b (yield: 90%).

(3) Synthesis of Intermediate Compound [1-c]

2,6-diphenylaniline (1.0 eq), Intermediate Compound [1-b] (1.2 eq), Pd2(dba)3(5 mol %), Sphos (7 mol %), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and then stirred for 12 hours at 110° C. to thereby obtain a product. The product was cooled at room temperature and then subjected to an extraction process three times utilizing dichloromethane and water to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and concentrated, and column chromatography was utilized to purify Intermediate Compound 1-c (yield: 72%).

(4) Synthesis of Intermediate Compound [1-d]

Intermediate Compound [1-c] (1.0 eq), Sn (1.5 eq), and HCl (30 eq) were dissolved in ethanol and then stirred for 12 hours at 80° C. to thereby obtain a product. The product was cooled at room temperature and then neutralized utilizing a NaOH solution. The neutralized product was subjected to an extraction process utilizing dichloromethane and water to obtain an organic layer, and then subjected to filtration through Celite/silica gel. The filtrate was dried utilizing magnesium sulfate and concentrated, and column chromatography (MC:hexane=a volume ratio of 1:3) was utilized to purify Intermediate Compound 1-d (yield: 86%).

(5) Synthesis of Intermediate Compound [1-e]

Intermediate Compound [1-d] (1.2 eq), 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.0 eq), Pd2(dba)3(5 mol %), Sphos (7 mol %), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M), and then stirred for 3 hours at 110° C., to thereby obtain a product. The product was cooled at room temperature and then subjected to an extraction process three times utilizing dichloromethane and water to thereby obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (ethyl acetate:hexane=a volume ratio of 1:9) was utilized to purify Intermediate Compound 1-e (yield: 78%).

(6) Synthesis of Intermediate Compound [1-f]

Intermediate compound [1-e] (1.0 eq) was dissolved in triethyl orthoformate (30 eq), and then 37% HCl (1.5 eq) was added thereto, followed by stirring for 12 hours at 80° C. The reaction was cooled to room temperature and concentrated, followed by an extraction process three times utilizing dichloromethane and water to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and concentrated, and column chromatography (MC:methanol=a volume ratio of 95:5) was utilized to purify Intermediate Compound 1-f (yield: 85%).

(7) Synthesis of Intermediate Compound [1-g]

Intermediate Compound [1-f] (1.0 eq) and ammonium hexafluorophosphate (3.0 eq) were dissolved in methanol (0.5 M), and distilled water was added thereto, followed by stirring for 3 hours at room temperature, to thereby obtain a product. The product was washed utilizing distilled water and subjected to filtration to thereby obtain a solid, and the solid was subjected to an extraction process three times utilizing dichloromethane and water, to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and concentrated, to thereby purify Intermediate Compound 1-g (yield of 90%).

(8) Synthesis of Compound [1]

Intermediate Compound [1-g], dichloro(1,5-cyclooctadiene)platinum (II) (1.1 eq), and sodium acetate (2.0 eq) were dissolved in anhydrous 1,4-dioxane (0.05 M), and then stirred for 4 days at 120° C. in the nitrogen condition, to thereby obtain a product. The product was cooled at room temperature and then subjected to an extraction process three times utilizing dichloromethane and water to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and concentrated, and column chromatography (MC:hexane=a volume ratio of 3:7) was utilized to purify Compound 1 (yield: 19%).

Synthesis Example 2: Synthesis of Compound 9

(1) Synthesis of Intermediate Compound [9-a]

(6-fluoro-4-methylpyridin-3-yl)boronic acid (1.2 eq), bromobenzene (1.0 eq), Pd(PPh3)4(0.05 eq), and K3PO4(2.0 eq) were mixed in 1,4-dioxane:H2O (a volume ratio=4:1) (0.1 M), and then stirred for 15 hours at 100° C. to thereby obtain a product. The reaction was cooled to room temperature and then subjected to an extraction process three times utilizing ethyl acetate and water to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and concentrated, and column chromatography was utilized to purify Intermediate Compound 9-a (yield: 86%).

(2) Synthesis of Intermediate Compound[9-b]

Intermediate Compound [9-a] (1.0 eq), 2-methoxy-9H-carbazole (1.1 eq), and K3PO4(2.0 eq) were mixed in DMF (0.1 M), and then stirred for 16 hours at 160° C., to thereby obtain a product. The reaction was cooled to room temperature and then distilled under reduced pressure to remove residual DMF solvent, followed by an extraction process three times utilizing dichloromethane and water to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and concentrated, and column chromatography was utilized to obtain a solid compound. The obtained solid compound, Sn (1.5 eq), and HCl (30 eq) were dissolved in ethanol and then stirred for 12 hours at 80° C. to thereby obtain a product. The reaction was cooled to room temperature and then neutralized utilizing a NaOH solution. The neutralized reaction was subjected to an extraction process utilizing dichloromethane and water to obtain an organic layer, and then subjected to filtration through Celite/silica gel. The filtrate was dried utilizing magnesium sulfate and concentrated, and column chromatography (MC:hexane=a volume ratio of 1:3) was utilized to purify Intermediate Compound 9-b (yield: 70%).

(3) Synthesis of Intermediate Compound [9-c]

Intermediate Compound [9-b] (1.0 eq), 1,3-dibromobenzene (1.5 eq), CuI (0.1 eq), 2-picolinic acid (0.1 eq), and K3PO4(2.0 eq) were dissolved in DMSO (0.2 M) and then stirred for 12 hours at 120° C., to thereby obtain a product. The reaction was cooled to room temperature and then subjected to an extraction process three times utilizing ethyl acetate and water to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and concentrated, and column chromatography was utilized to purify Intermediate Compound 9-c (yield: 64%).

(4) Synthesis of Intermediate Compound [9-d]

Intermediate Compound [1-d] (1.2 eq), Intermediate Compound [9-c] (1.0 eq), Pd2(dba)3(5 mol %), Sphos (7 mol %), and sodium tert-butoxide (2.0 eq) were dissolved in dioxane (0.1 M) and then stirred for 3 hours at 110° C. to thereby obtain a product. The product was cooled at room temperature and then subjected to an extraction process three times utilizing dichloromethane and water to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and concentrated, and column chromatography (dichloromethane:hexane=a volume ratio of 1:9) was utilized to purify Intermediate Compound 9-d (yield: 75%).

(5) Synthesis of Intermediate Compound [9-e]

Intermediate Compound [9-e] was synthesized in substantially the same manner as utilized to synthesize Intermediate Compound [1-f] of Synthesis Example 1, except that Intermediate Compound [9-d] was utilized instead of Intermediate Compound [1-e]. (yield: 85%)

(6) Synthesis of Intermediate Compound [9-f]

Intermediate Compound [9-f] was synthesized in substantially the same manner as utilized to synthesize Intermediate Compound [1-g] of Synthesis Example 1, except that Intermediate Compound [9-e] was utilized instead of Intermediate Compound [1-f]. (yield: 91%)

(7) Synthesis of Compound [9]

Compound [9] was synthesized in substantially the same manner as utilized to synthesize Compound [1] of Synthesis Example 1, except that Intermediate Compound [9-f] was utilized instead of Intermediate Compound [1-g]. (yield: 22%)

Synthesis Example 3: Synthesis of Compound 10

(1) Synthesis of Intermediate Compound [10-a]

Intermediate Compound [1-d] (1.2 eq), 2-(3-bromophenoxy)-6-(tert-butyl)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.0 eq), Pd2(dba)3(5 mol %), Xphos (7 mol %), and sodium tert-butoxide (2.0 eq) were dissolved in dioxane (0.1M) and then stirred for 3 hours at 110° C. to thereby generate a product. The reaction was cooled to room temperature and then subjected to an extraction process three times utilizing dichloromethane and water to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and concentrated, and column chromatography (dichloromethane:hexane=a volume ratio of 1:9) was utilized to purify Intermediate Compound 10-a (yield: 81%).

(2) Synthesis of Intermediate Compound[10-b]

Intermediate Compound [10-b] was synthesized in substantially the same manner as utilized to synthesize Intermediate Compound [1-f] of Synthesis Example 1, except that Intermediate Compound [10-a] was utilized instead of Intermediate Compound [1-e]. (yield: 90%)

(3) Synthesis of Intermediate Compound [10-c]

Intermediate Compound [10-b] was synthesized in substantially the same manner as utilized to synthesize Intermediate Compound [1-g] of Synthesis Example 1, except that Intermediate Compound [10-c] was utilized instead of Intermediate Compound [1-f]. (yield: 91%)

(5) Synthesis of Compound [10]

Compound [10] was synthesized in substantially the same manner as utilized to synthesize Compound [1] of Synthesis Example 1, except that Intermediate Compound [10-c] was utilized instead of Intermediate Compound [1-g]. (yield: 20%)

Synthesis Example 4: Synthesis of Compound 13

(1) Synthesis of Intermediate Compound [13-a]

(2) Synthesis of Intermediate Compound[13-b]

Intermediate Compound [13-a] (1.0 eq), Sn (1.5 eq), and HCl (30 eq) were dissolved in ethanol and then stirred for 12 hours at 80° C., to thereby obtain a product. The reaction was cooled at room temperature and then neutralized utilizing a NaOH solution. The neutralized reaction was subjected to an extraction process utilizing dichloromethane and water to obtain an organic layer, and then subjected to filtration through Celite/silica gel. The filtrate was dried utilizing magnesium sulfate to purify Intermediate Compound 13-b (yield: 88%).

(3) Synthesis of Intermediate Compound [13-c]

Intermediate Compound [13-b] (1.2 eq), 2-(3-bromophenoxy)-6-(tert-butyl)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.0 eq), Pd2(dba)3(5 mol %), Xphos (7 mol %), and sodium tert-butoxide (2.0 eq) were dissolved in dioxane (0.1M) and then stirred for 2 hours at 110° C., to thereby a product. The reaction was cooled to room temperature and then subjected to an extraction process three times utilizing dichloromethane and water to thereby obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (ethyl acetate:hexane=a volume ratio of 1:9) was utilized to purify Intermediate Compound 13-c (yield: 79%).

(4) Synthesis of Intermediate Compound [13-d]

Intermediate Compound [13-d] was synthesized in substantially the same manner as utilized to synthesize Intermediate Compound [1-f] of Synthesis Example 1, except that Intermediate Compound [13-c] was utilized instead of Intermediate Compound [1-e]. (yield: 88%)

(5) Synthesis of Intermediate Compound [13-e]

Intermediate Compound [13-e] was synthesized in substantially the same manner as utilized to synthesize Intermediate Compound [1-g] of Synthesis Example 1, except that Intermediate Compound [13-d] was utilized instead of Intermediate Compound [1-f]. (yield: 93%)

(6) Synthesis of Compound [13]

Compound [13] was synthesized in substantially the same manner as utilized to synthesize Compound [1] of Synthesis Example 1, except that Intermediate Compound [13-e] was utilized instead of Intermediate Compound [1-g]. (yield: 22%)

Synthesis Example 5: Synthesis of Compound 19

(1) Synthesis of Intermediate Compound [19-a]

Intermediate Compound [1-d] (1.2 eq), 2-(3-bromo-5-(tert-butyl)phenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.0 eq), Pd2(dba)3(5 mol %), Xphos (7 mol %), and sodium tert-butoxide (2.0 eq) were dissolved in dioxane (0.1M) and then stirred for 2 hours at 110° C., to thereby obtain a product. The reaction was cooled to room temperature and then subjected to an extraction process three times utilizing dichloromethane and water to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and concentrated, and column chromatography (dichloromethane:hexane=a volume ratio of 1:9) was utilized to purify Intermediate Compound 19-a (yield: 85%).

(2) Synthesis of Intermediate Compound[19-b]

Intermediate Compound [19-b] was synthesized in substantially the same manner as utilized to synthesize Intermediate Compound [1-f] of Synthesis Example 1, except that Intermediate Compound [19-a] was utilized instead of Intermediate Compound [1-e]. (yield: 89%)

(3) Synthesis of Intermediate Compound [19-c]

Intermediate Compound [19-c] was synthesized in substantially the same manner as utilized to synthesize Intermediate Compound [1-g] of Synthesis Example 1, except that Intermediate Compound [19-b] was utilized instead of Intermediate Compound [1-f]. (yield: 91%)

(4) Synthesis of Compound [19]

Compound [19] was synthesized in substantially the same manner as utilized to synthesize Compound [1] of Synthesis Example 1, except that Intermediate Compound [19-c] was utilized instead of Intermediate Compound [1-g]. (yield: 24%)

Synthesis Example 6: Synthesis of Compound 47

(1) Synthesis of Intermediate Compound [47-a]

(6-fluoro-4-methylpyridin-3-yl)boronic acid (1.2 eq), 1-bromo-4-tert-butylbenzene (1.0 eq), Pd(PPh3)4(0.05 eq), and K3PO4(2.0 eq) were mixed in 1,4-dioxane:H2O (a volume ratio=4:1) (0.1 M) and then stirred for 15 hours at 100° C. to thereby obtain a product. The reaction was cooled at room temperature and then subjected to an extraction process three times utilizing ethyl acetate and water to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and concentrated, and column chromatography was utilized to purify Intermediate Compound 47-a (yield: 95%).

(2) Synthesis of Intermediate Compound[47-b]

Intermediate Compound [47-a] (1.0 eq), 2-methoxy-9H-carbazole (1.1 eq), and K3PO4(2.0 eq) were mixed in DMF (0.1 M), and then stirred for 16 hours at 160° C., to thereby obtain a product. The reaction was cooled to room temperature and then distilled under reduced pressure to remove residual DMF solvent, followed by an extraction process three times utilizing dichloromethane and water to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and concentrated, and column chromatography was utilized to obtain a solid compound. The obtained solid compound, Sn (1.5 eq), and HCl (30 eq) were dissolved in ethanol and then stirred for 12 hours at 80° C., to thereby obtain a product. The product was cooled at room temperature and then neutralized utilizing a NaOH solution. The neutralized reaction was subjected to an extraction process utilizing dichloromethane and water to obtain an organic layer, and then subjected to filtration through Celite/silica gel. The filtrate was dried utilizing magnesium sulfate and concentrated, and column chromatography (MC:hexane=a volume ratio of 1:3) was utilized to purify Intermediate Compound 47-b (yield: 75%).

(3) Synthesis of Intermediate Compound [47-c]

Intermediate Compound [47-b] (1.0 eq), 1,3-dibromobenzene (1.5 eq), CuI (0.1 eq), 2-picolinic acid (0.1 eq), and K3PO4(2.0 eq) were dissolved in DMSO (0.2 M) and then stirred for 12 hours at 120° C., to thereby obtain a product. The reaction was cooled to room temperature and then subjected to an extraction process three times utilizing ethyl acetate and water to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and concentrated, and column chromatography was utilized to synthesize Intermediate Compound 47-c (yield: 60%).

(4) Synthesis of Intermediate Compound [47-d]

Intermediate Compound [1-d] (1.2 eq), Intermediate Compound [47-c] (1.0 eq), Pd2(dba)3(5 mol %), Sphos (7 mol %), and sodium tert-butoxide (2.0 eq) were dissolved in dioxane (0.1 M) and then stirred for 3 hours at 110° C., to thereby obtain a product. The reaction was cooled to room temperature and then subjected to an extraction process three times utilizing dichloromethane and water to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and concentrated, and column chromatography (dichloromethane:hexane=a volume ratio of 1:9) was utilized to purify Intermediate Compound 47-d (yield: 72%).

(5) Synthesis of Intermediate Compound [47-e]

Intermediate Compound [47-e] was synthesized in substantially the same manner as utilized to synthesize Intermediate Compound [1-f] of Synthesis Example 1, except that Intermediate Compound [47-d] was utilized instead of Intermediate Compound [1-e]. (yield: 89%)

(6) Synthesis of Intermediate Compound [47-f]

Intermediate Compound [47-f] was synthesized in substantially the same manner as utilized to synthesize Intermediate Compound [1-g] of Synthesis Example 1, except that Intermediate Compound [47-e] was utilized instead of Intermediate Compound [1-f]. (yield: 91%)

(7) Synthesis of Compound [47]

Compound [47] was synthesized in substantially the same manner as utilized to synthesize Compound [1] of Synthesis Example 1, except that Intermediate Compound [47-f] was utilized instead of Intermediate Compound [1-g]. (yield: 18%)

Synthesis Example 7: Synthesis of Compound 51

(1) Synthesis of Intermediate Compound [51-a]

[1,1′:3′,1″:3″,1′″-quaterphenyl]-4′-amine (1.0 eq), Intermediate Compound [1-b] (1.2 eq), Pd2(dba)3(5 mol %), Sphos (7 mol %), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M) and then stirred for 12 hours at 110° C., to thereby obtain a product. The reaction was cooled to room temperature and then subjected to an extraction process three times utilizing dichloromethane and water to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and concentrated, and column chromatography was utilized to purify Intermediate Compound 51-a (yield: 61%).

(2) Synthesis of Intermediate Compound[51-b]

Intermediate Compound [51-a] (1.0 eq), Sn (1.5 eq), and HCl (30 eq) were dissolved in ethanol and then stirred for 12 hours at 80° C., to thereby obtain a product. The reaction was cooled to room temperature and then neutralized utilizing a NaOH solution. The neutralizer was subjected to an extraction process utilizing dichloromethane and water to obtain an organic layer, and then subjected to filtration through Celite/silica gel. The filtrate was dried utilizing magnesium sulfate, thereby isolating Intermediate Compound 51-b (yield: 86%).

(3) Synthesis of Intermediate Compound [51-c]

Intermediate Compound [51-b] (1.2 eq), 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (1.0 eq), Pd2(dba)3(5 mol %), Sphos (7 mol %), and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.1 M), and then, stirred for 3 hours at 110° C., to thereby obtain a product. The reaction was cooled to room temperature and then subjected to an extraction process three times utilizing dichloromethane and water to thereby obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (ethyl acetate:hexane=a volume ratio of 1:9) was utilized to purify Intermediate Compound 51-c (yield: 71%).

(4) Synthesis of Intermediate Compound [51-d]

Intermediate Compound [51-d] was synthesized in substantially the same manner as utilized to synthesize Intermediate Compound [1-f] of Synthesis Example 1, except that Intermediate Compound [51-c] was utilized instead of Intermediate Compound [1-e]. (yield: 88%)

(5) Synthesis of Intermediate Compound [51-e]

Intermediate Compound [51-e] was synthesized in substantially the same manner as utilized to synthesize Intermediate Compound [1-g] of Synthesis Example 1, except that Intermediate Compound [51-d] was utilized instead of Intermediate Compound [1-f]. (yield: 93%)

(6) Synthesis of Compound [51]

Compound [51] was synthesized in substantially the same manner as utilized to synthesize Compound [1] of Synthesis Example 1, except that Intermediate Compound [51-e] was utilized instead of Intermediate Compound [1-g]. (yield: 21%)

Synthesis Example 8: Synthesis of Compound 74

(1) Synthesis of Intermediate Compound [74-a]

Intermediate Compound [9-b] (1.0 eq), 3′,5′-dibromo-2,6-diisopropyl-1,1′-biphenyl (1.5 eq), CuI (0.1 eq), 2-picolinic acid (0.1 eq), and K3PO4(2.0 eq) were dissolved in DMSO (0.2 M) and then stirred for 12 hours at 120° C., to thereby obtain a product. The reaction was cooled to room temperature and then subjected to an extraction process three times utilizing ethyl acetate and water, to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and concentrated, and column chromatography was utilized to purify Intermediate Compound 74-a (yield: 57%).

(2) Synthesis of Intermediate Compound[74-b]

Intermediate Compound [74-a] (1.0 eq), Intermediate Compound [1-d] (1.2 eq), Pd2(dba)3(5 mol %), Xphos (7 mol %), and sodium tert-butoxide (2.0 eq) were dissolved in 1,4-dioxane (0.1 M) and then stirred for 3 hours at 110° C., to thereby obtain a product. The reaction was cooled to room temperature and then subjected to an extraction process three times utilizing dichloromethane and water to thereby obtain an organic layer. The obtained organic layer was dried by utilizing magnesium sulfate and concentrated, and column chromatography (ethyl acetate:hexane=a volume ratio of 1:9) was utilized to purify Intermediate Compound 74-b (yield: 85%).

(3) Synthesis of Intermediate Compound [74-c]

Intermediate Compound [74-c] was synthesized in substantially the same manner as utilized to synthesize Intermediate Compound [1-f] of Synthesis Example 1, except that Intermediate Compound [74-b] was utilized instead of Intermediate Compound [1-e]. (yield: 91%)

(4) Synthesis of Intermediate Compound [74-d]

Intermediate Compound [74-d] was synthesized in substantially the same manner as utilized to synthesize Intermediate Compound [1-g] of Synthesis Example 1, except that Intermediate Compound [74-c] was utilized instead of Intermediate Compound [1-f]. (yield: 90%)

(5) Synthesis of Compound [74]

Compound [74] was synthesized in substantially the same manner as utilized to synthesize Compound [1] of Synthesis Example 1, except that Intermediate Compound [74-d] was utilized instead of Intermediate Compound [1-g]. (yield: 22%)

Synthesis Example 9: Synthesis of Compound 81

(1) Synthesis of Intermediate Compound [81-a]

(2) Synthesis of Intermediate Compound[81-b]

Intermediate Compound [81-a] (1.0 eq) was dissolved in anhydrous THF (0.1 M), and then 1.0 M n-BuLi in hexane (1.1 eq) was slowly added thereto at −78° C., followed by stirring for an hour. Anhydrous DMF (2.5 eq) was added to the reaction and then stirred for 12 hours at room temperature. The reaction was cooled to room temperature and then subjected to an extraction process three times utilizing dichloromethane and water, to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and then concentrated, and column chromatography (ethyl acetate:hexane=a volume ratio of 1:10) was utilized to purify Intermediate Compound 81-b (yield: 54%).

(3) Synthesis of Intermediate Compound [81-c]

Intermediate Compound [81-b] (1.0 eq), 1-bromo-3-iodobenzene (1.3 eq), Ni(dppe)Br2([1,2-bis(diphenylphosphino)ethane]dibromo nickel(II)) (0.1 eq), and Zn powder (2.7 eq) were dissolved in THF (0.1 M) and then stirred for 30 hours at 110° C., to thereby obtain a product. The reaction was cooled to room temperature and then subjected to an extraction process three times utilizing ether and water, to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and then concentrated, and column chromatography (ethyl acetate:hexane=a volume ratio of 5:95) was utilized to purify Intermediate Compound 81-c (yield: 73%).

(4) Synthesis of Intermediate Compound [81-d]

Intermediate Compound [1-d] (1.2 eq), Intermediate Compound [81-c] (1.0 eq), Pd2(dba)3(5 mol %), Sphos (7 mol %), and sodium tert-butoxide (2.0 eq) were dissolved in dioxane (0.1 M) and then stirred for 2 hours at 110° C. to thereby obtain a product. The reaction was cooled to room temperature and then subjected to an extraction process three times utilizing dichloromethane and water to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and concentrated, and column chromatography (dichloromethane:hexane=a volume ratio of 1:9) was utilized to purify Intermediate Compound 81-d (yield: 76%).

(5) Synthesis of Intermediate Compound [81-e]

Intermediate Compound [81-e] was synthesized in substantially the same manner as utilized to synthesize Intermediate Compound [1-f] of Synthesis Example 1, except that Intermediate Compound [81-d] was utilized instead of Intermediate Compound [1-e]. (yield: 85%)

(6) Synthesis of Intermediate Compound [81-f]

Intermediate Compound [81-f] was synthesized in substantially the same manner as utilized to synthesize Intermediate Compound [1-g] of Synthesis Example 1, except that Intermediate Compound [81-e] was utilized instead of Intermediate Compound [1-f]. (yield: 90%)

(7) Synthesis of Compound [81]

Compound [81] was synthesized in substantially the same manner as utilized to synthesize Compound [1] of Synthesis Example 1, except that Intermediate Compound [81-f] was utilized instead of Intermediate Compound [1-g]. (yield: 20%)

Synthesis Example 10: Synthesis of Compound 90

(1) Synthesis of Intermediate Compound [90-a]

Intermediate Compound [81-c] (1.0 eq), triethylsilane (2.0 eq), and 1,3-dimethyl-1H-naphtho[1,8-de]-1,2,3-triazinium tetrakis(2,3,4,5,6-pentafluorophenyl)borate (0.05 eq) were dissolved in dichloromethane (0.1 M) and then stirred for 24 hours at room temperature to thereby obtain a product. The reaction was cooled to room temperature and then subjected to an extraction process three times utilizing dichloromethane and water to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and concentrated, and column chromatography was utilized to purify Intermediate Compound 90-a (yield: 95%).

(2) Synthesis of Intermediate Compound[90-b]

Intermediate Compound [1-d] (1.2 eq), Intermediate Compound [90-a] (1.0 eq), Pd2(dba)3(5 mol %), Xphos (7 mol %), and sodium tert-butoxide (2.0 eq) were dissolved in 1,4-dioxane (0.1 M) and then stirred for 2 hours at 110° C. to thereby obtain a product. The reaction was cooled to room temperature and then subjected to an extraction process three times utilizing dichloromethane and water to thereby obtain an organic layer. The obtained organic layer was dried utilizing magnesium sulfate and concentrated, and column chromatography (dichloromethane:hexane=a volume ratio of 1:9) was utilized to purify Intermediate Compound 90-b (yield: 69%).

(3) Synthesis of Intermediate Compound [90-c]

Intermediate Compound [90-c] was synthesized in substantially the same manner as utilized to synthesize Intermediate Compound [1-f] of Synthesis Example 1, except that Intermediate Compound [90-b] was utilized instead of Intermediate Compound [1-e]. (yield: 89%)

(4) Synthesis of Intermediate Compound [90-d]

Intermediate Compound [90-c] was synthesized in substantially the same manner as utilized to synthesize Intermediate Compound [1-g] of Synthesis Example 1, except that Intermediate Compound [90-c] was utilized instead of Intermediate Compound [1-f]. (yield 95%)

(5) Synthesis of Compound [90]

Compound [90] was synthesized in substantially the same manner as utilized to synthesize Compound [1] of Synthesis Example 1, except that Intermediate Compound [90-d] was utilized instead of Intermediate Compound [1-g]. (yield: 21%)

1H NMR and MALDI-TOF MS of the compounds synthesized according to Synthesis Examples 1 to 10 are shown in Table 1. Synthesis methods of other compounds in addition to the compounds synthesized in Synthesis Examples 1 to 10 may be easily recognized by those skilled in the art by referring to the synthesis paths and source materials.

Evaluation Example 1

HOMO energies, LUMO energies,3MLCT(%), simulated (e.g., calculated) maximum emission wavelengths (λmaxsim), real (e.g., experimental) maximum emission wavelengths (λmaxexp), and3MC energies of the compounds prepared in Synthesis Examples 1 to 10 and Comparative Examples 1 to 3 were measured, and the results are shown in Table 2.

For example, characteristics of Compounds 1, 9, 10, 13, 19, 47, 51, 74, 81, and 90, and Compounds A and B (as comparative compounds) were evaluated, and the HOMO and LUMO energy were measured by differential pulse voltammetry. The “bandgap” is an absolute value of a difference between a LUMO energy level and a HOMO energy level. The3MC state energy level value was evaluated utilizing the B3LYP functional. The3MLCT(%) value was measured by structural optimization at the level of B3LYP, 6-31 G(d,p) utilizing a density functional theory (DFT) calculation method of the Gaussian program.

As an anode, a glass substrate (product of Corning Inc.) with a 15 Ω/cm2(1,200 Å) ITO formed thereon was cut to a size of 50 mm×50 mm×0.7 mm, sonicated utilizing isopropyl alcohol and pure water each for 5 minutes, washed by irradiation of ultraviolet rays and exposure of ozone thereto for 30 minutes, and then mounted on a vacuum deposition apparatus.

2-TNATA was vacuum-deposited on the anode to form a hole injection layer having a thickness of 600 Å, and 4,4′-bis[N-(1-naphthyl)—N-phenylamino]biphenyl (hereinafter, referred as “NPB”) was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 300 Å.

Compound 1 (first compound), Compound ETH66 (second compound), and Compound HTH29 (third compound) were vacuum-deposited on the hole transport layer to form an emission layer having a thickness of 400 Å. In this regard, an amount of Compound 1 was 10 wt % based on the total weight of the emission layer (100 wt %), and a weight ratio of Compound ETH66 and Compound HTH29 was adjusted to 3:7.

Compound ETH2 was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 50 Å, Alq3 was vacuum-deposited on the hole blocking layer to form an electron transport layer having a thickness of 300 Å, LiF was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and then Al was vacuum-deposited thereon to form a cathode having a thickness of 3,000 Å, thereby completing manufacture of an organic light-emitting device.

Examples 2 to 10

Additional organic light-emitting devices were manufactured in substantially the same manner as in Example 1, except that the compounds described in Table 3 were utilized as the first compound, the second compound, and the third compound in the formation of the emission layer.

In forming an emission layer, an organic light-emitting device was manufactured in substantially the same manner as in Example 1, except that Compound 1 (first compound), Compound ETH66 (second compound), Compound HTH29 (third compound), and Compound DFD1 (fourth compound) instead of Compound 1 (first compound), Compound ETH66 (second compound), and Compound HTH29 (third compound) were vacuum-deposited on the hole transport layer. In this regard, an amount of Compound 1 was 10 wt % based on the total weight of the emission layer (100 wt %), an amount of Compound DFD1 is 0.5 wt % based on the total weight of the emission layer (100 wt %), and a weight ratio of Compound ETH66 to Compound HTH29 was adjusted to 3:7.

Evaluation Example 2

Driving voltage (V) at 1,000 cd/m2, luminescence efficiency (cd/A), color conversion efficiency (cd/A/y), maximum emission wavelength (nm), and lifespan (T90) of the organic light-emitting devices manufactured in Examples 1 to 11 were each measured utilizing a Keithley MU 236 and a luminance meter PR650, and results thereof are shown in Tables 3 and 4, respectively. In Table 4, the lifespan (T90) is a measure of the time (hr) taken when the luminance reaches 90% of the initial luminance.

From Tables 3 and 4, it may be confirmed that the organic light-emitting devices of Examples 1 to 11 each emit deep blue light, and also have excellent or suitable driving voltage, luminescence efficiency, color conversion efficiency, and/or lifespan characteristics.

Terms such as “substantially,” “about,” and “-” are used as terms of approximation and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by those of ordinary skill in the art. They may be inclusive of the stated value and an acceptable range of deviation as determined by one of ordinary skill in the art, considering the limitations and error associated with measurement of that quantity. For example, “about” may refer to one or more standard deviations, or ±30%, 20%, 10%, 5% of the stated value.

Numerical ranges disclosed herein include and are intended to disclose all subsumed sub-ranges of the same numerical precision. For example, a range of “1.0 to 10.0” includes all subranges having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Applicant therefore reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein.