Patent Application
20250120302
The present application claims priority to and the benefit of Korean Patent Application No. 10-2023-0133693, filed on Oct. 6, 2023, in the Korean Intellectual Property Office, the entire content of which is incorporated herein by reference.
One or more embodiments of the present disclosure relate to a light-emitting device including an organometallic compound, an electronic apparatus including the light-emitting device, and the organometallic compound.
Among light-emitting devices, self-emissive devices (e.g., organic light-emitting devices) have relatively wide viewing angles, relatively high contrast ratios, relatively short response times, and excellent or suitable characteristics in terms of luminance, driving voltage, and response speed.
In a light-emitting device, a first electrode is arranged on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially arranged on the first electrode. Holes provided from the first electrode move toward the emission layer through the hole transport region, and electrons provided from the second electrode move toward the emission layer through the electron transport region. Carriers, such as the holes and electrons, recombine in the emission layer to produce excitons. These excitons transition and decay from an excited state to a ground state, thereby generating light.
One or more aspects of embodiments of the present disclosure are directed toward a light-emitting device including an organometallic compound, an electronic apparatus including the light-emitting device, and the organometallic compound.
Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to one or more embodiments of the present disclosure, a light-emitting device includes:
According to one or more embodiments of the present disclosure, an electronic apparatus includes the light-emitting device.
According to one or more embodiments of the present disclosure, electronic equipment includes the light-emitting device.
According to one or more embodiments of the present disclosure, provided is the organometallic compound represented by Formula 1.
The accompanying drawings are included to provide a further understanding of the present disclosure and are incorporated in and constitute a part of the present disclosure. The drawings illustrate embodiments of the present disclosure and, together with the description, serve to explain principles of the present disclosure. The above and other aspects, features, and advantages of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, in which:
Reference will now be made in more detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout the present disclosure, and duplicative descriptions thereof may not be provided for conciseness. In this regard, the presented embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments of the present disclosure are merely described, by referring to the drawings, to explain aspects of the present disclosure. As utilized herein, the term “and/or” or “or” may include any and all combinations of one or more of the associated listed items. Throughout the disclosure, the 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. For example, “at least one of a, b or c”, “at least one selected from a, b, and c”, “at least one selected from among a to c”, etc., may indicate only a, only b, only c, both (e.g., simultaneously) a and b, both (e.g., simultaneously) a and c, both (e.g., simultaneously) b and c, all of a, b, and c, or variations thereof. The “/” utilized herein may be interpreted as “and” or as “or” depending on the situation.
According to one or more embodiments of the present disclosure, a light-emitting device may include:
Details on Formula 1 may be the same as described herein.
In one or more embodiments,
In one or more embodiments, the interlayer of the light-emitting device may include the organometallic compound represented by Formula 1 (e.g., as a first compound).
In one or more embodiments, the emission layer of the light-emitting device may include the organometallic compound represented by Formula 1.
In one or more embodiments, the emission layer of the light-emitting device may include a dopant and a host, and the organometallic compound represented by Formula 1 may be included in the dopant. For example, in some embodiments, the organometallic compound may act as a dopant. For example, in some embodiments, the emission layer may be to emit blue light. The blue light may have a maximum emission wavelength in a range of, for example, about 430 nm to about 480 nm.
In one or more embodiments, the electron transport region of the light-emitting device may include a hole-blocking layer, and the hole-blocking layer may include a phosphine oxide-containing compound, a silicon-containing compound, or any combination thereof. In one or more embodiments, the hole-blocking layer may directly contact the emission layer.
In one or more embodiments, the light-emitting device may further include a second compound including at least one π electron-deficient nitrogen-containing C1-C60 heterocyclic group, a third compound including a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or any combination thereof, and
In one or more embodiments, the organometallic compound may include at least one deuterium.
In one or more embodiments, the second compound, the third compound, and the fourth compound may each include at least one deuterium.
In one or more embodiments, the second compound may include at least one silicon.
In one or more embodiments, the third compound may include at least one silicon.
In one or more embodiments, the light-emitting device may further include, in addition to the organometallic compound represented by Formula 1, a second compound and a third compound, wherein at least one of the second compound or the third compound may include at least one deuterium, at least one silicon, or any combination thereof.
According to one or more embodiments, the light-emitting device (for example, the emission layer of the light-emitting device) may include a second compound in addition to the organometallic compound. At least one of the organometallic compound or the second compound may include at least one deuterium. For example, in some embodiments, the light-emitting device (for example, the emission layer of the light-emitting device) may further include a third compound, a fourth compound, or any combination thereof, in addition to the organometallic compound and the second compound.
In one or more embodiments, the light-emitting device (for example, the emission layer of the light-emitting device) may further include a third compound in addition to the organometallic compound. At least one of the organometallic compound or the third compound may include at least one deuterium. For example, in some embodiments, the light-emitting device (for example, the emission layer of the light-emitting device) may further include, in addition to the organometallic compound and the third compound, a second compound, a fourth compound, or any combination thereof.
In one or more embodiments, the light-emitting device (for example, the emission layer of the light-emitting device) may further include a fourth compound in addition to the organometallic compound. At least one of the organometallic compound or the fourth compound may include at least one deuterium. The fourth compound may serve to improve color purity, luminescence efficiency, and lifespan characteristics of the light-emitting device. For example, in some embodiments, the light-emitting device (for example, the emission layer of the light-emitting device) may further include a second compound, a third compound, or any combination thereof, in addition to the organometallic compound and the fourth compound.
In one or more embodiments, the light-emitting device (for example, the emission layer of the light-emitting device) may further include a second compound and a third compound, in addition to the organometallic compound. The second compound and the third compound may form an exciplex. At least one selected from among the organometallic compound, the second compound, and the third compound may include at least one deuterium.
In one or more embodiments, the emission layer of the light-emitting device may include: i) the organometallic compound; and ii) the second compound, the third compound, the fourth compound, or any combination thereof, and the emission layer may be to emit blue light.
In one or more embodiments, the maximum emission wavelength of the blue light may be in a range of about 430 nm to about 480 nm, about 430 nm to about 475 nm, about 440 nm to about 475 nm, about 450 nm to about 475 nm, about 430 nm to about 470 nm, about 440 nm to about 470 nm, about 450 nm to about 470 nm, about 430 nm to about 465 nm, about 440 nm to about 465 nm, about 450 nm to about 465 nm, about 430 nm to about 460 nm, about 440 nm to about 460 nm, or about 450 nm to about 460 nm.
In one or more embodiments, the second compound may include a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or any combination thereof.
In one or more embodiments, the following compounds may be excluded from the third compound:
In one or more embodiments, a difference between a triplet energy level (eV) of the fourth compound and a singlet energy level (eV) of the fourth compound may be about 0 eV or higher and about 0.5 eV or lower (or, about 0 eV or higher and about 0.3 eV or lower).
In one or more embodiments, the fourth compound may be a compound including at least one cyclic group including each of boron (B) and nitrogen (N) as ring-forming atoms.
In one or more embodiments, the fourth compound may be a C8-C60 polycyclic group-containing compound including at least two condensed cyclic groups that share a boron atom (B) (e.g., one being a first ring and the other being a second ring).
In one or more embodiments, the fourth compound may include a condensed ring in which at least one third ring may be condensed with at least one fourth ring, for example, to form the condensed ring including four or more rings,
In one or more embodiments, the third compound may not include (e.g., may exclude) a (e.g., any) compound represented by Formula 3-1 described in the present disclosure.
In one or more embodiments, the second compound may include a compound represented by Formula 2:
In Formula 2,
In one or more embodiments, 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:
In some embodiments, the fourth compound may be a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof:
In one or more embodiments, the light-emitting device may satisfy at least one selected from among Conditions 1 to 4:
Lowest unoccupied molecular orbital (LUMO) energy level (eV) of third compound>LUMO energy level (eV) of organometallic compound Condition 1
LUMO energy level (eV) of organometallic compound>LUMO energy level (eV) of second compound Condition 2
Highest occupied molecular orbital (HOMO) energy level (eV) of organometallic compound>HOMO energy level (eV) of third compound Condition 3
HOMO energy level (eV) of the third compound>HOMO energy level (eV) of the second compound Condition 4
Each of the HOMO energy level and LUMO energy level of each of the organometallic compound, the second compound, and the third compound may be a negative value, and may be measured according to a suitable method.
In one or more embodiments, an absolute value of a difference between the LUMO energy level of the organometallic 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, an absolute value of a difference between the LUMO energy level of the organometallic 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, an absolute value of a difference between the HOMO energy level of the organometallic compound and the HOMO energy level of the second compound may be about 1.25 eV or lower (for example, about 1.25 eV or lower and about 0.2 eV or higher), and/or an absolute value of a difference between the HOMO energy level of the organometallic compound and the HOMO energy level of the third compound may be about 1.25 eV or lower (for example, 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 as described above, the balance between holes and electrons injected into the emission layer may be made.
The light-emitting device may have a structure of a first embodiment or a second embodiment.
According to the first embodiment, the organometallic compound may be included in the emission layer in the interlayer of the light-emitting device, wherein the emission layer may further include a host, the organometallic compound may be different from the host, and the emission layer may be to emit phosphorescence or fluorescence emitted from the organometallic compound. For example, according to the first embodiment, the organometallic compound may be a dopant or an emitter. In one or more embodiments, the organometallic compound may be a phosphorescent dopant or a phosphorescent emitter.
Phosphorescence or fluorescence emitted from the organometallic compound may be blue light.
In one or more embodiments, the emission layer may further include an auxiliary dopant. The auxiliary dopant may improve luminescence efficiency from the organometallic compound by effectively transferring energy to the organometallic compound as a dopant or an emitter.
The auxiliary dopant may be different from the organometallic compound and the host.
In one or more embodiments, the auxiliary dopant may be a delayed fluorescence-emitting compound.
In some embodiments, the auxiliary dopant may be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.
According to the second embodiment, the organometallic compound may be included in the emission layer in the interlayer of the light-emitting device, wherein the emission layer may further include a host and a dopant, the organometallic compound, the host, and the dopant may be different from one another, and the emission layer may be to emit phosphorescence or fluorescence (for example, delayed fluorescence) from the dopant.
In one or more embodiments, the organometallic compound in the second embodiment may serve not as a dopant but as an auxiliary dopant that transfers energy to a dopant (or an emitter).
In one or more embodiments, the organometallic compound in the second embodiment may serve as an emitter and also as an auxiliary dopant that transfers energy to a dopant (or an emitter).
For example, in some embodiments, phosphorescence or fluorescence emitted from the dopant (or the emitter) in the second embodiment may be blue phosphorescence or blue fluorescence (for example, blue delayed fluorescence).
The dopant (or the emitter) in the second embodiment may be a phosphorescent dopant material (for example, the organometallic compound represented by Formula 1, an organometallic compound represented by Formula 401, or any combination thereof) or any fluorescent dopant material (for example, a compound represented by Formula 501, a compound represented by Formula 502, a 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 nanometer (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 (for example, a compound represented by Formula 301, a compound represented by 301-1, a compound represented by Formula 301-2, or any combination thereof).
In one or more embodiments, the host in the first embodiment and the second embodiment may be the second compound, the third compound, or any combination thereof.
In one or more embodiments, the light-emitting device may further include a capping layer arranged outside (e.g., on) the first electrode and/or outside (e.g., on) the second electrode.
In one or more embodiments, the light-emitting device may further include at least one of a first capping layer located outside (e.g., on) the first electrode or a second capping layer located outside (e.g., on) 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 the second capping layer may each be the same as described herein.
In one or more embodiments, the light-emitting device may further include:
The expression that an “(interlayer and/or a capping layer) includes at least one organometallic compound represented by Formula 1” as utilized herein may be construed as meaning that the “(interlayer and/or the capping layer) may include one organometallic compound represented by Formula 1 or two or more different organometallic compounds each represented by Formula 1.”
In one or more embodiments, the interlayer and/or the 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 one or more embodiments, 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 substantially the same layer (for example, both (e.g., simultaneously) 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 between the first electrode and the second electrode of the light-emitting device.
According to one or more embodiments of the present disclosure, an electronic apparatus may include the light-emitting device. In one or more embodiments, the electronic apparatus may further include a thin-film transistor. For example, in some embodiments, 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 some embodiments, the electronic apparatus may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. More details of the electronic apparatus may be referred to the descriptions provided herein.
According to one or more embodiments of the present disclosure, an electronic equipment may include the light-emitting device.
For example, the electronic equipment may include (e.g., be) at least one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor light and/or light for signal, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a portable phone, a tablet personal computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality or augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater or stadium screen, a phototherapy device, or a signboard.
According to one or more embodiments of the present disclosure, provided is an organometallic compound represented by Formula 1. Details on Formula 1 may be the same as described herein.
Methods of synthesizing the organometallic compound may be easily understood to those of ordinary skill in the art by referring to Synthesis Examples and/or Examples described herein.
In Formula 1, M may be platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm).
In one or more embodiments, M may be platinum (Pt), palladium (Pd), or gold (Au).
In one or more embodiments, M may be Pt.
Regarding Formula 1, X1 may be N and X2 may be C.
ring CY1 and ring CY2 in Formula 1 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
In one or more embodiments, ring CY1, and CY2 may each independently be:
In one or more embodiments, ring CY1 may be a nitrogen-containing C1-C60 heterocyclic group.
In one or more embodiments, ring CY1 may be a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, a benzopyrazole group, a benzimidazole group, or a benzothiazole group.
In one or more embodiments, ring CY2 may be a C2-C8 monocyclic group; or a C4-C20 polycyclic group in which two or three C2-C8 monocyclic groups are condensed with each other.
In one or more embodiments, ring CY2 may be a benzene group, a pyridine group, a pyrimidine group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azacarbazole group, an azafluorene group, or an azadibenzosilole group.
L1 and L2 in Formula 1 may each independently be a single bond, *—C(R1a)(R1b)—*′, *—C(Ra1)═*′, *═C(R1a)—*′, *—C(R1a)═C(R1b)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(Ra1)—*′, *—N(Ra1)—*′, *—O—*′, *—P(Ra1)—*′, *—Al(Ra1)—*′, *—Si(Ra1)(R1b)—*′, *—P(═O)(Ra1)—*′, *—S—*′, *—S(═O)—*′, *—S(═O)2—*′, or *—Ge(R1a)(R1b)—*′, and * and *′ each indicate a binding site to a neighboring atom.
n1 and n2 in Formula 1 may indicate the number of L1 and the number of L2, respectively, and may each independently be an integer from 1 to 5. When n1 is 2 or more, two or more of L1(s) may be the same as or different from each other, and when n2 is 2 or more, two or more of L2(s) may be the same as or different from each other.
R1a and R1b may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C1-C60 alkylthio group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio 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).
R10a may be the same as described herein.
In one or more embodiments, R1a and R1b may optionally be bound to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
R10a may be the same as described herein.
In one or more embodiments, R1a and R1b may each independently be:
In one or more embodiments, L1 may be a single bond.
In one or more embodiments, L2 may be *—O—*′ or *—S—*′, and n2 may be 1.
In an embodiment, L1 may be a single bond, and L2 may be *—O—*′ or *—S—*′, and n2 may be 1.
R1 to R7 in Formula 1 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C1-C60 alkylthio group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio 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).
R10a may be the same as described herein.
a1 to a7 in Formula 1 indicate the number of R1 to the number of R7, respectively, and a1 and a2 may each independently be an integer from 1 to 20, and a3, a4, a6, and a7 may each independently be an integer from 1 to 3, and a5 may be an integer from 1 to 4. when a1 is 2 or more, two or more of R1(s) may be the same as or different from each other, when a2 is 2 or more, two or more of R2(s) may be the same as or different from each other, when a3 is 2 or more, two or more of R3(s) may be the same as or different from each other, when a4 is 2 or more, two or more of R4(s) may be the same as or different from each other, when a5 is 2 or more, two or more of R5(s) may be the same as or different from each other, when a6 is 2 or more, two or more of R6(s) may be the same as or different from each other, and when a7 is 2 or more, two or more of R7(s) may be the same as or different from each other.
In one or more embodiments, two or more adjacent groups selected from among a1 R1 may optionally be bound to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
In one or more embodiments, two or more adjacent groups selected from among a2 R2 may optionally be bound to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
In one or more embodiments, two or more adjacent groups selected from among a3 R3 may optionally be bound to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
In one or more embodiments, two or more adjacent groups selected from among a4 R4 may optionally be bound to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
In one or more embodiments, two or more adjacent groups selected from among a5 R5 may optionally be bound to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
In one or more embodiments, two or more adjacent groups selected from among a6 R6 may optionally be bound to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
In one or more embodiments, two or more adjacent groups selected from among a7 R7 may optionally be bound to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
R10a may be the same as described herein.
In one or more embodiments, R1 to R7 may each independently be:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, or a C1-C20 alkoxy group;
In one or more embodiments, R1 to R7 may each independently be:
Ar1 and Ar2 in Formula 1 may each independently be a group represented by Formula 1A:
Y1 to Y3, Z1, and Z2 in Formula 1A may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C1-C60 alkylthio group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio 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).
In one or more embodiments, Y1 to Y3, Z1, and Z2 may each independently be:
In one or more embodiments, Y1 to Y3, Z1, and Z2 may each independently be:
At least one of Z1 or Z2 in Formula 1A may be a C1-C60 alkyl group unsubstituted or substituted with at least one R10a.
In one or more embodiments, at least one of Z1 or Z2 may be:
In one or more embodiments, at least one of Z1 or Z2 may be a tert-butyl group.
In one or more embodiments, one of (e.g., selected from among) Z1 and Z2 may be an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, or a tert-pentyl group, each unsubstituted or substituted with at least one deuterium,
In one or more embodiments, one of (e.g., selected from among) Z1 and Z2 may be an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, or a tert-pentyl group, each unsubstituted or substituted with at least one deuterium, and
In one or more embodiments, Y1 to Y3 may each independently be hydrogen or deuterium.
* Formula 1A indicates a binding site to a neighboring atom in Formula 1.
In one or more embodiments, two or more adjacent groups selected from among R1 to R7, R1a, R1b, Ar1, and/or Ar2 may optionally be bound to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
In one or more embodiments, a group represented by
in Formula 1 may be a group represented by one selected from among CY1(1) to CY1(29):
In one or more embodiments, a group represented by
in Formula 1 may be a group represented by one selected from among Formulae CY2(1) to CY2(25):
In one or more embodiments, the organometallic compound may be represented by Formula 1-1 or Formula 1-2:
In the organometallic compound represented by Formula 1, a terphenyl group is bound to a benzimidazole group in an ortho-ortho-ortho structure, and substituents Ar1 and Ar2 each represented by Formula 1A are located on two of the benzene rings included in the terphenyl group. Accordingly, when the organometallic compound is utilized in electronic devices (for example, an organic light-emitting device, in particular, an emission layer of an organic light-emitting device), color purity and efficiency are improved, a lifespan is increased, and the heat resistance of a material is greatly improved. Thus, high-quality electronic apparatuses may be manufactured.
L51 to L53 in Formula 2 may each independently be a single bond, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
b51 to b53 in Formula 2 indicate the number of L51 to the number of L53, respectively, and may each be an integer from 1 to 5. When b51 is 2 or more, two or more of L51(s) may be identical to or different from each other, when b52 is 2 or more, two or more of L52(s) may be identical to or different from each other, and when b53 is 2 or more, two or more of L53(s) may be identical to or different from each other. In some embodiments, b51 to b53 may each independently be 1 or 2.
In one or more embodiments, L51 to L53 in Formula 2 may each independently be:
In one or more embodiments, in Formula 2, a bond between L51 and R51, a bond between L52 and R52, a bond between L53 and R53, a bond between two L51(s), a bond between two L52(s), a bond between two L53(s), a bond between L51 and carbon between X54 and X55 in Formula 2, a bond between L52 and carbon between X54 and X56 in Formula 2, and a bond between L53 and carbon between X55 and X56 in Formula 2 may each be a “carbon-carbon single bond.”
In Formula 2, X54 may be N or C(R54), X55 may be N or C(R55), X56 may be N or C(R56), and at least one selected from among X54 to X56 may be N. R54 to R56 may each independently be the same as described herein. In one or more embodiments, two or three selected from among X54 to X56 may be N.
R51 to R56 in Formula 2 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, a C7-C60 arylalkyl group unsubstituted or substituted with at least one R10a, a C2-C60 heteroarylalkyl 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). Q1 to Q3 may each be the same as described herein.
In one or more embodiments, R51 to R56 in Formula 2 may each independently be:
For example, in one or more embodiments, in Formula 91,
In one or more embodiments, a group represented by *-(L51)b51-R51 and a group represented by *-(L52)b52-R52 in Formula 2 may each not be a phenyl group.
In one or more embodiments, a group represented by *-(L51)b51-R51 and a group represented by *-(L52)b52-R52 in Formula 2 may be identical to each other.
In one or more embodiments, a group represented by *-(L51)b51-R51 and a group represented by *-(L52)b52-R52 in Formula 2 may be different from each other.
In one or more embodiments, b51 and b52 in Formula 2 may each be 1, 2, or 3, and L51 and L52 may 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 one or more embodiments, R51 and R52 in Formula 2 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), or —Si(Q1)(Q2)(Q3), and
In one or more embodiments,
For example, in one or more embodiments,
Ring CY71 to ring CY74 in Formulae 3-1 to 3-5 may each independently be a π electron-rich C3-C60 cyclic group or a pyridine group.
X82 in Formulae 3-1 to 3-5 may be a single bond, O, S, N[(L82)b82-R82], C(R82a)(R82a), or Si(R82a)(R82a).
X83 in Formulae 3-1 to 3-5 may be a single bond, O, S, N[(L83)b83-R83], C(R83a)(R83a), or Si(R83a)(R83a).
X84 in Formulae 3-1 to 3-5 may be O, S, N[(L84)b84-R84], C(R84a)(R84a), or Si(R84a)(R84a).
X85 in Formulae 3-1 to 3-5 may be C or Si.
L81 to L85 in Formulae 3-1 to 3-5 may each independently be a single bond, *—C(Q4)(Q5)—*′, *—Si(Q4)(Q5)-*′, a π electron-rich C3-C60 cyclic group that is unsubstituted or substituted with at least one R10a, or a pyridine group that is unsubstituted or substituted with at least one R10a.
Q4 and Q5 may each be the same as described with respect to Q1.
b81 to b85 in Formulae 3-1 to 3-5 may each independently be an integer from 1 to 5.
R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, and R84b may each be the same as described herein.
R10a may be the same as described herein.
In one or more embodiments, in Formulae 3-1 to 3-5, L81 to L85 may each independently be:
In one or more embodiments, a group represented by
in Formulae 3-1 and 3-2 may be a group represented by one selected from among Formulae CY71-1(1) to CY71-1(8), and/or
in Formulae 3-1 and 3-3 may be a group represented by one selected from among Formulae CY71-2(1) to CY71-2(8), and/or
in Formulae 3-2 and 3-4 may be a group represented by one selected from among Formulae CY71-3(1) to CY71-3(32), and/or
in Formulae 3-3 to 3-5 may be a group represented by one selected from among Formulae CY71-4(1) to CY71-4(32), and/or
in Formula 3-5 may be a group represented by one selected from among Formulae CY71-5(1) to CY71-5(8):
Ring A501 to ring A504 in Formulae 502 and 503 may each independently be a C3-C60 carbocyclic group or a C1-C60 heterocyclic group.
Y505 in Formulae 502 and 503 may be O, S, N(R505), B(R505), C(R505a)(R505b), or Si(R505a)(R505b).
Y506 in Formulae 502 and 503 may be O, S, N(R506), B(R506), C(R506a)(R506b), or Si(R506a)(R506b).
Y507 in Formula 503 may be O, S, N(R507), B(R507), C(R507a)(R507a), or Si(R507a)(R507b).
Y508 in Formula 503 may be O, S, N(R508), B(R508), C(R508a)(R508a), or Si(R508a)(R508b).
Y51 and Y52 in Formulae 502 and 503 may each independently be B, P(═O), or S(═O).
R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b in Formulae 502 and 503 may be the same as described herein.
R51 to R56, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, R84b, R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b in the present disclosure may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, a C7-C60 aryl alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 heteroaryl alkyl 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). Q1 to Q3 may each be the same as described herein.
In one or more embodiments, i) R51 to R56, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, and R84b, R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b in Formulae 2, 3-1 to 3-5, 502, and 503, and ii) R10a may each independently be:
In one or more embodiments, i) R1 to R7 in Formula 1, Y1 to Y3, Z1, and Z2 in Formula 1A, ii) R51 to R56, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, and R84b, R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b, in Formulae 2, 3-1 to 3-5, 502, and 503, and iii) R10a may each independently be:
In Formulae 9-1 to 9-19 and 10-1 to 10-246, * indicates a binding site to a neighboring atom, “Ph” represents a phenyl group, “D” represents deuterium, and “TMS” represents a trimethylsilyl group.
In one or more embodiments, the organometallic compound represented by Formula 1 may be one selected from among Compounds BD01 to BD112:
Ar in Compounds BD01 to BD112 may be a group represented by Formula 1B(1), Ar in Compounds BD113 and BD114 may be a group represented by Formula 1B(2), Ar in Compounds BD115 and BD116 may be a group represented by Formula 1B(3), Ar in Compound BD117 may be a group represented by Formula 1B(4), Ar in Compound BD118 may be a group represented by Formula 1B(5), and Ar in Compounds BD119 and BD120 may be a group represented by Formula 1B(6),
For example, in one or more embodiments, the second compound may be one selected from among Compounds ETH1 to ETH100:
For example, in one or more embodiments, the third compound may be one selected from among Compounds HTH1 to HTH46
For example, in one or more embodiments, the fourth compound may be one elected from among Compounds DFD1 to DFD29:
In the compounds described above, Ph represents a phenyl group, D5 represents substitution with five deuterium, and D4 represents substitution with four deuterium. For example, a group represented by
may be identical to a group represented by
Hereinafter, the structure of the light-emitting device 10 according to one or more embodiments and a method of manufacturing the light-emitting device 10 will be described with reference to
In
The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a material for forming the first electrode 110 may be a high-work function material that facilitates injection of holes.
The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In one or more embodiments, when the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, a material for forming the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof.
The first electrode 110 may have a single-layer structure including (e.g., consisting of) a single layer or a multi-layer structure including multiple layers. For example, in some embodiments, the first electrode 110 may have a three-layer structure of ITO/Ag/ITO.
The interlayer 130 may be arranged on the first electrode 110. The interlayer 130 may include the emission layer.
In one or more embodiments, the interlayer 130 may further include a hole transport region between the first electrode 110 and the emission layer, and an electron transport region between the emission layer and the second electrode 150.
In one or more embodiments, The interlayer 130 may further include, in addition to one or more suitable organic materials, a metal-containing compound such as an organometallic compound, for example, the organometallic compound represented by Formula 1, an inorganic material such as quantum dots, and/or the like.
In one or more embodiments, the interlayer 130 may include, i) two or more emitting units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge generation layer between the two or more emitting units. When the interlayer 130 includes the two or more emitting units and the charge generation layer, the light-emitting device 10 may be a tandem light-emitting device.
The hole transport region may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) multiple materials that are different from each other, or iii) a multi-layer structure including multiple layers including multiple materials that are different from each other.
The hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron-blocking layer, or any combination thereof.
For example, in some embodiments, the hole transport region 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, wherein constituent layers of each structure are stacked sequentially from the first electrode 110 in the stated order.
In one or more embodiments, the hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
In Formulae 201 and 202,
For example, in some embodiments, each of Formulae 201 and 202 may include at least one selected from groups represented by Formulae CY201 to CY217:
In Formulae CY201 to CY217, R10b and R10c may each be the same as described with respect to R10a, ring CY201 to ring CY204 may each independently be a C3-C20 carbocyclic group or a C1-C20 heterocyclic group, and at least one hydrogen in Formulae CY201 to CY217 may be unsubstituted or substituted with R10a.
In one or more embodiments, ring CY201 to ring CY204 in Formulae CY201 to CY217 may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.
In one or more embodiments, each of Formulae 201 and 202 may include at least one selected from among the groups represented by Formulae CY201 to CY203.
In one or more embodiments, Formula 201 may include at least one selected from among the groups represented by Formulae CY201 to CY203 and at least one selected from among the groups represented by Formulae CY204 to CY217.
In one or more embodiments, in Formula 201, xa1 may be 1, R201 may be one selected from among the groups represented by Formulae CY201 to CY203, xa2 may be 0, and R202 may be one selected from among the groups represented by Formulae CY204 to CY207.
In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) any of the groups represented by Formulae CY201 to CY203.
In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) any of the groups represented by Formulae CY201 to CY203, and may include at least one selected from the groups represented by Formulae CY204 to CY217.
In one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) any of the groups represented by Formulae CY201 to CY217. In present disclosure, “not include a or any ‘component’” “exclude a or any ‘component’”, “‘component’-free”, and/or the like refers to that the “component” not being added, selected or utilized as a component in the composition/formula/structure, but, in some embodiments, the “component” of less than a suitable amount may still be included due to other impurities and/or external factors.
For example, in one or more embodiments, the hole transport region may include: at least one selected from among Compounds HT1 to HT46; 4,4′,4″-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA); 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA); 4,4′,4″-tris[N-(2-naphthyl)-N-phenylamino]-triphenylamine (2-TNATA); N,N′-di(naphthalen-1-yl)-N,N′-diphenyl-benzidine (NPB(NPD)); β-NPB; N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (TPD); spiro-TPD; spiro-NPB; methylated NPB; 4,4′-cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine](TAPC); 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD); 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA); polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA); poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS); polyaniline/camphor sulfonic acid (PANI/CSA); polyaniline/poly(4-styrenesulfonate) (PANI/PSS); or any combination thereof:
A thickness of the hole transport region may be in a range of about 50 Å to about 10,000 Å, for example, about 100 Å to about 4,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
The emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by the emission layer, and the electron-blocking layer may block or reduce the leakage of electrons from the emission layer to the hole transport region. Materials that may be included in the hole transport region may be included in the emission auxiliary layer and the electron-blocking layer.
p-Dopant
In one or more embodiments, the hole transport region may further include, in addition to one or more of these aforementioned 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).
The charge-generation material may be, for example, a p-dopant.
For example, in one or more embodiments, the p-dopant may have a LUMO energy level of less than or equal to −3.5 eV.
In one or more embodiments, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound including element EL1 and element EL2, or any combination thereof.
Non-limiting examples of the quinone derivative are tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), and/or the like.
Non-limiting examples of the cyano group-containing compound are dipyrazino[2,3-f: 2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), a compound represented by Formula 221, and/or the like:
In Formula 221,
In the compound including element EL1 and element EL2, element EL1 may be a metal, a metalloid, or any combination thereof, and element EL2 may be a non-metal, a metalloid, or any combination thereof.
Non-limiting examples of the metal are an alkali metal (for example, lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); an alkaline earth metal (for example, beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); a transition metal (for example, titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); a post-transition metal (for example, zinc (Zn), indium (In), tin (Sn), etc.); a lanthanide metal (for example, lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.); and/or the like.
Non-limiting examples of the metalloid are silicon (Si), antimony (Sb), tellurium (Te), and/or the like.
Non-limiting examples of the non-metal are oxygen (O), a halogen (for example, F, Cl, Br, I, etc.), and/or the like.
Non-limiting examples of the compound including element EL1 and element EL2 are metal oxides, metal halides (for example, metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metalloid halides (for example, metalloid fluorides, metalloid chlorides, metalloid bromides, metalloid iodides, etc.), metal tellurides, or one or more combinations thereof.
Non-limiting examples of the metal oxide are tungsten oxides (for example, WO, W2O3, WO2, WO3, W2O5, etc.), vanadium oxides (for example, VO, V2O3, VO2, V2O5, etc.), molybdenum oxides (MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), rhenium oxides (for example, ReO3, etc.), and/or the like.
Non-limiting examples of the metal halide are alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, lanthanide metal halides, and/or the like.
Non-limiting examples of the alkali metal halide are LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, and/or the like.
Non-limiting examples of the alkaline earth metal halide are BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2), SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, Mg12, CaI2, Sr12, BaI2, and/or the like.
Non-limiting examples of the transition metal halide are titanium halides (for example, TiF4, TiC4, TiBr4, TiI4, etc.), zirconium halides (for example, ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), hafnium halides (for example, HfF4, HfCl4, HfBr4, HfI4, etc.), vanadium halides (for example, VF3, VCl3, VBrs, VI3, etc.), niobium halides (for example, NbF3, NbCl3, NbBr3, NbI3, etc.), tantalum halides (for example, TaF3, TaCl3, TaBr3, TaI3, etc.), chromium halides (for example, CrF3, CrCl3, CrBr3, CrI3, etc.), molybdenum halides (for example, MoF3, MoCl3, MoBr3, MoI3, etc.), tungsten halides (for example, WF3, WCl3, WBr3, WI3, etc.), manganese halides (for example, MnF2, MnCl2, MnBr2, MnI2, etc.), technetium halides (for example, TcF2, TcCl2, TcBr2, TcI2, etc.), rhenium halides (for example, ReF2, ReCl2, ReBr2, ReI2, etc.), ferrous halides (for example, FeF2, FeCl2, FeBr2, FeI2, etc.), ruthenium halides (for example, RuF2, RuCl2, RuBr2, RuI2, etc.), osmium halides (for example, OsF2, OsCl2, OsBr2, OsI2, etc.), cobalt halides (for example, CoF2, COCl2, CoBr2, CoI2, etc.), rhodium halides (for example, RhF2, RhCl2, RhBr2, RhI2, etc.), iridium halides (for example, IrF2, IrCl2, IrBr2, IrI2, etc.), nickel halides (for example, NiF2, NiCl2, NiBr2, NiI2, etc.), palladium halides (for example, PdF2, PdCl2, PdBr2, PdI2, etc.), platinum halides (for example, PtF2, PtCl2, PtBr2, PtI2, etc.), cuprous halides (for example, CuF, CuCl, CuBr, Cul, etc.), silver halides (for example, AgF, AgCl, AgBr, AgI, etc.), gold halides (for example, AuF, AuCl, AuBr, AuI, etc.), and/or the like.
Non-limiting examples of the post-transition metal halide are zinc halides (for example, ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halides (for example, Ink3, etc.), tin halides (for example, SnI2, etc.), and/or the like.
Non-limiting examples of the lanthanide metal halide are YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, SmI3, and/or the like.
Non-limiting examples of the metalloid halide are antimony halides (for example, SbCl5, etc.) and/or the like.
Non-limiting examples of the metal telluride are alkali metal tellurides (for example, Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), alkaline earth metal tellurides (for example, BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (for example, TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, etc.), post-transition metal tellurides (for example, ZnTe, etc.), lanthanide metal tellurides (for example, LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.), and/or the like.
When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from among a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers contact each other or are separated from each other, to emit white light (e.g., combined white light). In one or more embodiments, the emission layer may include two or more materials selected from among a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed with each other in a single layer, to emit white light (e.g., combined white light).
In one or more embodiments, the emission layer may include a host and a dopant (or emitter). In some embodiments, the emission layer may further include an auxiliary dopant that promotes energy transfer to the dopant (or emitter), in addition to the host and the dopant (or emitter). When the emission layer includes the dopant (or emitter) and the auxiliary dopant, the dopant (or emitter) and the auxiliary dopant are different from each other.
The organometallic compound represented by Formula 1 in the present disclosure may serve as the dopant (or emitter), or may serve as the auxiliary dopant.
An amount (weight) of the dopant (or emitter) in the emission layer may be in a range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.
The organometallic compound represented by the Formula 1 may be included in the emission layer. An amount (weight) of the organometallic compound in the emission layer may be about 0.01 parts by weight to about 30 parts by weight, about 0.1 parts by weight to about 20 parts by weight, or about 0.1 parts by weight to about 15 parts by weight, based on 100 parts by weight of the emission layer.
In one or more embodiments, the emission layer may include a quantum dot.
In one or more embodiments, the emission layer may include a delayed fluorescence material. The delayed fluorescence material may act as a host or a dopant in the emission layer 120.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within these ranges, excellent or suitable luminescence characteristics may be obtained without a substantial increase in driving voltage.
The host in the emission layer may include the second compound or the third compound described in the present disclosure, or a combination thereof.
In one or more embodiments, the host may include a compound represented by Formula 301:
[Ar301]xb11-[(L301)xb1-R301]xb21, Formula 301
For example, in some embodiments, when xb11 in Formula 301 is 2 or more, two or more of Ar301(s) may be linked to each other via a single bond.
In one or more embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
In Formulae 301-1 and 301-2,
In one or more embodiments, the host may include an alkaline earth metal complex, a post-transition metal complex, or any combination thereof. In one or more embodiments, the host may include a Be complex (for example, Compound H55), an Mg complex, a Zn complex, or any combination thereof.
In one or more embodiments, the host may include: at least one selected from among Compounds H1 to H128; 9,10-di(2-naphthyl)anthracene (ADN); 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN); 9,10-di(2-naphthyl)-2-t-butyl-anthracene (TBADN); 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP); 1,3-di(9H-carbazol-9-yl)benzene (mCP); 1,3,5-tri(carbazol-9-yl)benzene (TCP); or any combination thereof:
In one or more embodiments, the host may include a silicon-containing compound, a phosphine oxide-containing compound, or any combination thereof.
The host may have one or more 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, as a phosphorescent dopant, the organometallic compound represented by Formula 1 as described in the present disclosure.
In one or more embodiments, in the case (e.g., embodiments) where the emission layer includes the organometallic compound represented by Formula 1 as described herein and the organometallic compound represented by Formula 1 as described herein acts as an auxiliary dopant, the emission layer may further include a phosphorescent dopant.
The phosphorescent dopant may include at least one transition metal as a central metal.
The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
The phosphorescent dopant may be electrically neutral.
For example, in some embodiments, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
In Formulae 401 and 402,
For example, in some embodiments, in Formula 402, i) X401 may be nitrogen and X402 may be carbon, or ii) each of X401 and X402 may be nitrogen.
In one or more embodiments, when xc1 in Formula 401 is 2 or more, two ring A401(s) among two or more of L401(s) may optionally be linked to each other via T402, which is a linking group, and/or two ring A402(s) among two or more of L401(s) may optionally be linked to each other via T403, which is a linking group (see Compounds PD1 to PD4 and PD7). T402 and T403 may each be the same as described with respect to T401.
In Formula 401, L402 may be an organic ligand. For example, L402 may include a halogen, a diketone group (for example, an acetylacetonate group), a carboxylic acid group (for example, a picolinate group), —C(═O), an isonitrile group, a —CN group, a phosphorus-containing group (for example, a phosphine group, a phosphite group, etc.), or any combination thereof.
In one or more embodiments, the phosphorescent dopant may include, for example, one selected from among Compounds PD1 to PD39, or any combination thereof:
In the case (e.g., embodiments) where the emission layer includes the organometallic compound represented by Formula 1 as described herein and the organometallic compound represented by Formula 1 as described herein acts as an auxiliary dopant, the emission layer may further include a fluorescent dopant.
In one or more embodiments, in the case (e.g., embodiments) where the emission layer includes the organometallic compound represented by Formula 1 as described herein and the organometallic compound represented by Formula 1 as described herein acts 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 arylamine compound, a styrylamine compound, a boron-containing compound, or any combination thereof.
In one or more embodiments, the fluorescent dopant and the auxiliary dopant may each independently include a compound represented by Formula 501:
In Formula 501,
In one or more embodiments, Ar501 in Formula 501 may be a condensed cyclic group (for example, an anthracene group, a chrysene group, a pyrene group, etc.) in which three or more monocyclic groups are condensed together.
In some embodiments, xd4 in Formula 501 may be 2.
For example, in one or more embodiments, the fluorescent dopant and the auxiliary dopant may each independently include at least one selected from among Compounds FD1 to FD37; 4,4′-bis(2,2-diphenylvinyl)-1,1′-biphenyl (DPVBi), 4,4′-bis[4-(N,N-diphenylamino)styryl]biphenyl (DPAVBi); or any combination thereof:
In one or more embodiments, the emission layer may include a delayed fluorescence material.
In the present disclosure, 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 may include, for example, the fourth compound described in this disclosure.
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 one or more embodiments, a difference between a triplet energy level (eV) of the delayed fluorescence material and a singlet energy level (eV) 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 (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material is satisfied within the range above, up-conversion from the triplet state to the singlet state of the delayed fluorescence materials may effectively occur, and thus, the light-emitting device 10 may have improved luminescence efficiency.
For example, in one or more embodiments, the delayed fluorescence material may include: i) a material including at least one electron donor (for example, a π electron-rich C3-C60 cyclic group and/or the like, such as a carbazole group) and at least one electron acceptor (for example, a sulfoxide group, a cyano group, a π electron-deficient nitrogen-containing C1-C60 cyclic group, and/or the like), ii) a material including a C8-C60 polycyclic group including at least two cyclic groups condensed to each other while sharing boron (B), and/or iii) the like.
Non-limiting examples of the delayed fluorescence material may include at least one selected from among Compounds DF1 to DF14:
In one or more embodiments, the emission layer may include a quantum dot.
The term “quantum dot” as utilized herein 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.
A diameter of the quantum dot may be, for example, in a range of about 1 nm to about 10 nm. In the present disclosure, when dot, dots, or dot particles are spherical, “diameter” indicates a particle diameter or an average particle diameter, and when the particles are non-spherical, the “diameter” indicates a major axis length or an average major axis length. The diameter of the particles may be measured utilizing a scanning electron microscope or a particle size analyzer. As the particle size analyzer, for example, HORIBA, LA-950 laser particle size analyzer, may be utilized. When the size of the particles is measured utilizing a particle size analyzer, the average particle diameter is referred to as D50. D50 refers to the average diameter of particles whose cumulative volume corresponds to 50 vol % in the particle size distribution (e.g., cumulative distribution), and refers to the value of the particle size corresponding to 50% from the smallest particle when the total number of particles is 100% in the distribution curve accumulated in the order of the smallest particle size to the largest particle size.
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.
The wet chemical process is a method including mixing a precursor material of a quantum dot with an organic solvent and then growing quantum dot particle crystals. When the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal so that the growth of quantum dot particles may be controlled or selected through a process which costs lower, and is easier than vapor deposition methods, such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).
The quantum dot may include: a Group II-VI semiconductor compound; a Group III-V semiconductor compound; a Group III-VI semiconductor compound; a Group I-III-VI semiconductor compound; a Group IV-VI semiconductor compound; a Group IV element or compound; or any combination thereof.
Non-limiting examples of the Group II-VI semiconductor compound are: a binary compound, such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and/or the like; a ternary compound, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, and/or the like; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and/or the like; or one or more combinations thereof.
Non-limiting examples of the Group III-V semiconductor compound are: a binary compound, such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and/or the like; a ternary compound, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, InPSb, and/or the like; a quaternary compound, such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and/or the like; or one or more combinations thereof. In some embodiments, the Group III-V semiconductor compound may further include a Group II element. Non-limiting examples of the Group III-V semiconductor compound further including the Group II element are InZnP, InGaZnP, InAlZnP, and/or the like.
Non-limiting examples of the Group III-VI semiconductor compound are: a binary compound, such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, InTe, and/or the like; a ternary compound, such as InGaS3, InGaSe3, and/or the like; or one or more combinations thereof.
Non-limiting examples of the Group I-III-VI semiconductor compound are: a ternary compound, such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, AgAlO2, and/or the like; or one or more combinations thereof.
Non-limiting examples of the Group IV-VI semiconductor compound are: a binary compound, such as SnS, SnSe, SnTe, PbS, PbSe, PbTe, and/or the like; a ternary compound, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and/or the like; a quaternary compound, such as SnPbSSe, SnPbSeTe, SnPbSTe, and/or the like; or one or more combinations thereof.
Non-limiting examples of the Group IV element or compound are: a single element compound, such as Si, Ge, and/or the like; a binary compound, such as SiC, SiGe, and/or the like; or one or more combinations thereof.
Each element included in a multi-element compound, such as the binary compound, the ternary compound, and the quaternary compound, may be present at a substantially uniform concentration or non-substantially uniform concentration in a particle.
In one or more embodiments, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is substantially uniform, or may have a core-shell dual structure. For example, a material included in the core and a material included in the shell may be different from each other.
The shell of the quantum dot may act as a protective layer which prevents chemical denaturation of the core to maintain semiconductor characteristics, and/or as a charging layer which impart electrophoretic characteristics to the quantum dot. The shell may be single-layered or multi-layered. The interface between the core and the shell may have a concentration gradient in which the concentration of an element existing in the shell decreases toward the center of the core.
Examples of the shell of the quantum dot are an oxide of metal, metalloid, or non-metal, a semiconductor compound, or any combination thereof. Non-limiting examples of the oxide of metal, metalloid, or non-metal are: a binary compound, such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, CO3O4, NiO, and/or the like; a ternary compound, such as MgAl2O4, CoFe2O4, NiFe2O4, CoMn2O4, and/or the like; or one or more combinations thereof. Examples of the semiconductor compound are: 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 one or more combinations thereof. Non-limiting examples of the semiconductor compound suitable as a shell are 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.
The quantum dot may have an full width of half maximum (FWHM) of the emission spectrum of not more than about 45 nm, not more than about 40 nm, or for example, not more than about 30 nm. When the FWHM of the emission spectrum of the quantum dot is within these ranges, the quantum dot may have improved color purity or improved color reproducibility. In some embodiments, because light emitted through the quantum dot is emitted in all directions, the wide viewing angle may be improved.
In one or more embodiments, the quantum dot may be in the form of spherical nanoparticles, pyramidal nanoparticles, multi-arm nanoparticles, or cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanoplate particles.
Because the energy band gap of the quantum dot may be adjusted by controlling the size of the quantum dot, light having one or more suitable wavelength bands may be obtained from a quantum dot emission layer. Accordingly, by utilizing quantum dots of different sizes, a light-emitting device that emits light of one or more suitable wavelengths may be implemented. In one or more embodiments, the size of the quantum dots may be selected to enable the quantum dots to emit red light, green light, and/or blue light. In some embodiments, the quantum dots with suitable sizes may be configured to emit white light by combination of light of one or more suitable colors.
The electron transport region 140 may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) multiple materials that are different from each other, or iii) a multi-layer structure including multiple layers including multiple materials that are different from each other.
The electron transport region may include a buffer layer, a hole-blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
For example, in one or more embodiments, the electron transport region may have an electron transport layer/electron injection layer structure, a hole-blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein constituent layers of each structure are sequentially stacked from the emission layer in the stated order.
In one or more embodiments, the electron transport region (for example, a buffer layer, a hole-blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound including at least one π electron-deficient nitrogen-containing C1-C60 heterocyclic group.
For example, in some embodiments, the electron transport region may include a compound represented by Formula 601:
[Ar601]xe11-[(L601)xe1-R601]xe21, Formula 601
In one or more embodiments, when xe11 in Formula 601 is 2 or more, two or more of Ar601(s) may be linked to each other via a single bond.
In one or more embodiments, Ar601 in Formula 601 may be a substituted or unsubstituted anthracene group.
In one or more embodiments, the electron transport region may include a compound represented by Formula 601-1:
For example, in some embodiments, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.
In one or more embodiments, the electron transport region may include: at least one selected from among Compounds ET1 to ET45; 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP); 4,7-diphenyl-1,10-phenanthroline (Bphen); tris(8-hydroxyquinolinato)aluminum (Alq3); bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum (BAIq); 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ); 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ); or any combination thereof:
A thickness of the electron transport region may be in a range of about 100 Å to about 5,000 Å, for example, about 160 Å to about 4,000 Å. When the electron transport region includes a buffer layer, a hole-blocking layer, an electron control layer, an electron transport layer, or any combination thereof, a thickness of the buffer layer, the hole-blocking layer, or the electron control layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å, and a thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thicknesses of the buffer layer, the hole-blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region are within these ranges, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
In one or more embodiments, the electron transport region (for example, the electron transport layer in the electron transport region) may further include, in addition to one or more of the materials described above, a metal-containing material.
The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. A metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and a metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the metal ion of the alkaline earth-metal complex may include a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.
For example, in some embodiments, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) or ET-D2:
In one or more embodiments, the electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may directly contact the second electrode 150.
The electron injection layer may have: i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) multiple layers that are different from each other, or iii) a multi-layered structure including multiple layers including multiple materials that are different from each other.
The electron injection layer may include an alkali metal, alkaline earth metal, a rare earth metal, an alkali metal-containing compound, alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may be oxides, halides (for example, fluorides, chlorides, bromides, iodides, etc.), or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, respectively, or any combination thereof.
The alkali metal-containing compound may include: an alkali metal oxide, such as Li2O, Cs2O, K2O, etc.; an alkali metal halide, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, etc.; or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound, such as BaO, SrO, CaO, BaxSr1-xO (wherein x is a real number satisfying 0<x<1), BaxCa1-xO (wherein x is a real number satisfying 0<x<1), and/or the like. The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In one or more embodiments, the rare earth metal-containing compound may include a lanthanide metal telluride. Non-limiting examples of the lanthanide metal telluride are LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, Lu2Te3, and/or the like.
The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include i) one of metal ions of the alkali metal, one of metal ions of the alkaline earth metal, and one of metal ions of the rare earth metal, respectively, and ii) a ligand bound to the metal ion (e.g., the respective 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.
In one or more embodiments, the electron injection layer may include (e.g., consist of) an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof, as described above. In one or more embodiments, the electron injection layer may further include an organic material (for example, a compound represented by Formula 601).
In one or more embodiments, the electron injection layer may include (e.g., consist of) i) an alkali metal-containing compound (for example, alkali metal halide), or ii) a) an alkali metal-containing compound (for example, alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, in some embodiments, the electron injection layer may be a KI:Yb co-deposited layer, an RbI:Yb co-deposited layer, a LiF:Yb co-deposited layer, and/or the like.
When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof may be substantially uniformly or non-uniformly dispersed in a matrix including the organic material.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, or, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 150 may be arranged on the interlayer 130 having the aforementioned structure. The second electrode 150 may be a cathode, which is an electron injection electrode, and as a material for forming the second electrode 150, a metal, an alloy, an electrically conductive compound, or any combination thereof, each having a low-work function, may be utilized.
The second electrode 150 may include Li, Ag, Mg, Al, Al—Li, Ca, Mg—In, Mg—Ag, Yb, Ag—Yb, ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
The second electrode 150 may have a single-layer structure or a multi-layer structure including multiple layers.
A first capping layer may be arranged outside (e.g., on) the first electrode 110, and/or a second capping layer may be arranged outside (e.g., on) the second electrode 150. In one or more embodiments, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are sequentially stacked in the stated order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order.
In some embodiments, light generated in the emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the first electrode 110 which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer. In some embodiments, light generated in the emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the second electrode 150 which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer.
The first capping layer and the second capping layer may increase external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 is increased, so that the luminescence efficiency of the light-emitting device 10 may be improved.
Each of the first capping layer and the second capping layer may include a material having a refractive index of greater than or equal to 1.6 (e.g., at 589 nm).
The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.
At least one of the first capping layer or the second capping layer may (e.g., the first capping layer and the second capping layer may each independently) include a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may each optionally be substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In one or more embodiments, at least one of the first capping layer or the second capping layer may (e.g., the first capping layer and the second capping layer may each independently) include an amine group-containing compound.
In one or more embodiments, at least one of the first capping layer or the second capping layer may (e.g., the first capping layer and the second capping layer may each independently) include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
In one or more embodiments, at least one of the first capping layer or the second capping layer may (e.g., the first capping layer and the second capping layer may each independently) include at least one selected from among Compounds HT28 to HT33, at least one selected from among Compounds CP1 to CP6, β-NPB, or any combination thereof:
The organometallic compound represented by Formula 1 may be included in one or more suitable films. Accordingly, one or more aspects of embodiments of the present disclosure are directed toward a film including the organometallic compound represented by Formula 1. The film may be, for example, an optical member (or a light control element) (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), and/or a protective member (for example, an insulating layer, a dielectric layer, and/or the like).
The light-emitting device may be included in one or more suitable electronic apparatuses. For example, in one or more embodiments, the electronic apparatus including the light-emitting device may be a light-emitting apparatus, an authentication apparatus, and/or the like.
In one or more embodiments, the electronic apparatus (for example, a 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 arranged in at least one travel direction of light emitted from the light-emitting device. For example, in some embodiments, light emitted from the light-emitting device may be blue light, green light, or white light (e.g., combined white light). Details on the light-emitting device may be referred to the descriptions provided herein. In some embodiments, the color conversion layer may include a quantum dot.
The electronic apparatus may include a first substrate. The first substrate may include a plurality of subpixel areas, the color filter may include a plurality of color filter areas respectively corresponding to the subpixel areas, and the color conversion layer may include a plurality of color conversion areas respectively corresponding to the subpixel areas.
A pixel-defining film may be arranged 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 arranged among the color filter areas, and the color conversion layer may further include a plurality of color conversion areas and light-shielding patterns arranged among the color conversion areas.
The plurality of color filter areas (or the plurality of color conversion areas) may include a first area configured to emit first color light, a second area configured to emit second color light, and/or a third area configured to emit third color light, wherein the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths from one another. For example, in one or more embodiments, 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. For example, in one or more embodiments, the plurality of color filter areas (or the plurality of color conversion areas) may include quantum dots. In some embodiments, the first area may include a red quantum dot to emit red light, the second area may include a green quantum dot to emit green light, and the third area may not include (e.g., may exclude) any quantum dot. Details on the quantum dot may be referred to the descriptions provided herein. The first area, the second area, and/or the third area may each further include a scatter.
For example, in one or more embodiments, the light-emitting device may be to emit first light, the first area may be to absorb the first light to emit first-first color light, the second area may be to absorb the first light to emit second-first color light, and the third area may be to absorb the first light to emit third-first color light. Here, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths. In some embodiments, 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.
In one or more embodiments, the electronic apparatus may further include a thin-film transistor, in addition to the light-emitting device as described above. The thin-film transistor may include a source electrode, a drain electrode, and an activation layer, wherein one selected from among the source electrode and the drain electrode may be electrically connected to the first electrode or the second electrode of the light-emitting device.
The thin-film transistor may further include a gate electrode, a gate insulating film, and/or the like.
The activation layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, and/or the like.
In one or more embodiments, the electronic apparatus may further include a sealing portion for sealing the light-emitting device. The sealing portion may be arranged between the color filter and/or the color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside, and concurrently (e.g., simultaneously) prevents ambient air and moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one layer of an organic layer and/or an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic apparatus may be flexible.
In one or more embodiments, various functional layers may be additionally arranged on the sealing portion, in addition to the color filter and/or the color conversion layer, according to the utilization of the electronic apparatus. Non-limiting examples of the functional layers may include a touch screen layer, a polarizing layer, and/or the like. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer.
The authentication apparatus may be, for example, a biometric authentication apparatus that authenticates an individual by utilizing biometric information of a living body (for example, fingertips, pupils, etc.). The authentication apparatus may further include, in addition to the light-emitting device as described above, a biometric information collector.
The electronic apparatus may be applied to one or more of displays, light sources, lighting, personal computers (for example, a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (for example, electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, one or more suitable measuring instruments, meters (for example, meters for a vehicle, an aircraft, and a vessel), projectors, and/or the like.
The light-emitting device may be included in one or more suitable electronic equipment.
For example, the electronic equipment including the light-emitting device may include (e.g., be) at least one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, a light for indoor or outdoor lighting and/or signaling, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a 3D display, a virtual or augmented-reality display, a vehicle, a video wall including multiple displays tiled together, a theater or stadium screen, a phototherapy device, or a signboard.
Because the light-emitting device has excellent or suitable effects in terms of luminescence efficiency long lifespan, the electronic equipment including the light-emitting device may have desirable characteristics with high luminance, high resolution, and low power consumption.
The light-emitting apparatus of
The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be on the substrate 100. The buffer layer 210 may prevent or reduce penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.
The TFT may be on the buffer layer 210. The TFT may include an activation layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
The activation layer 220 may include an inorganic semiconductor, such as silicon 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 film 230 for insulating the activation layer 220 from the gate electrode 240 may be on the activation layer 220, and the gate electrode 240 may be on the gate insulating film 230.
An interlayer insulating film 250 may be on the gate electrode 240. The interlayer insulating film 250 may be arranged between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270, to insulate from one another.
The source electrode 260 and the drain electrode 270 may be on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the activation layer 220, and the source electrode 260 and the drain electrode 270 may be arranged in contact with the exposed portions of the source region and the drain region of the activation layer 220, respectively.
The TFT may be electrically connected to the light-emitting device to drive the light-emitting device, and may be covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. The light-emitting device may be provided on the passivation layer 280. The light-emitting device may include a first electrode 110, an interlayer 130, and a second electrode 150.
The first electrode 110 may be on the passivation layer 280. The passivation layer 280 may be arranged to expose a portion of the drain electrode 270, not fully covering the drain electrode 270, and the first electrode 110 may be arranged to be connected to the exposed portion of the drain electrode 270.
A pixel defining layer 290 including an insulating material may be on the first electrode 110. The pixel defining layer 290 may expose a certain region of the first electrode 110, and the interlayer 130 may be formed in the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide-based organic film or a polyacrylic-based organic film. In some embodiments, at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel defining layer 290 to be arranged in the form of a common layer.
The second electrode 150 may be on the interlayer 130, and a second capping layer 170 may be additionally formed on the second electrode 150. The second capping layer 170 may be formed to cover the second electrode 150.
The encapsulation portion 300 may be on the second capping layer 170. The encapsulation portion 300 may be arranged on the light-emitting device to protect the light-emitting device from moisture and/or oxygen. The encapsulation portion 300 may include: an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic-based resin (for example, polymethyl methacrylate, polyacrylic acid, and/or the like), an epoxy-based resin (for example, aliphatic glycidyl ether (AGE), and/or the like), or any combination thereof; or any combination of the inorganic film(s) and the organic film(s).
The light-emitting apparatus of
The electronic equipment 1 may include a display area DA and a non-display area NDA outside the display area DA. A display device of the electronic equipment 1 may implement an image through an array of a plurality of pixels that are two-dimensionally arranged in the display area DA.
The non-display area NDA is an area that does not display an image, and may entirely surround the display area DA. On the non-display area NDA, a driver for providing electrical signals or power to display devices arranged on the display area DA may be arranged. On the non-display area NDA, a pad, which is an area to which an electronic element or a printing circuit board, may be electrically connected may be arranged.
In the electronic equipment 1, a length in the x-axis direction and a length (e.g., a width) in the y-axis direction may be different from each other. In some embodiments, as shown in
Referring to
In one or more embodiments, the vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a set or predetermined direction according to rotation of at least one wheel thereof. For example, the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a prime mover device, a bicycle, or a train running on a track.
The vehicle 1000 may include a body having an interior and an exterior, and a chassis in which mechanical apparatuses necessary for driving are installed as other parts except for the body. The exterior of the body may include a front panel, a bonnet, a roof panel, a rear panel, a trunk, a pillar provided at a boundary between doors, and/or the like. The chassis of the vehicle 1000 may include a power generating device, a power transmitting device, a driving device, a steering device, a braking device, a suspension device, a transmission device, a fuel device, front and rear left and right wheels, and/or the like.
The vehicle 1000 may include a side window glass 1100, a front window glass 1200, a side mirror 1300, a cluster 1400, a center fascia 1500, a passenger seat dashboard 1600, and a display device 2.
The side window glass 1100 and the front window glass 1200 may be partitioned by a pillar arranged between the side window glass 1100 and the front window glass 1200.
The side window glass 1100 may be installed on a side of the vehicle 1000. In some embodiments, the side window glass 1100 may be installed on a door of the vehicle 1000. A plurality of side window glasses 1100 may be provided and may face each other. In some embodiments, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In some embodiments, the first side window glass 1110 may be arranged adjacent to the cluster 1400. The second side window glass 1120 may be arranged adjacent to the passenger seat dashboard 1600.
In one or more embodiments, the side window glasses 1100 may be spaced apart from each other in the x-direction or the −x-direction (the direction opposite the x-direction). For example, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the x direction or the −x direction.
In other words, an imaginary straight line L connecting the side window glasses 1100 may extend in the x-direction or the −x-direction. For example, an imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 to each other may extend in the x direction or the −x direction.
The front window glass 1200 may be installed in the front of the vehicle 1000. The front window glass 1200 may be arranged between the side window glasses 1100 facing each other.
The side mirror 1300 may provide a rear view of the vehicle 1000. The side mirror 1300 may be installed on the exterior of the vehicle body. In one embodiment, a plurality of side mirrors 1300 may be provided. Any one of the plurality of side mirrors 1300 may be arranged outside the first side window glass 1110. The other one of the plurality of side mirrors 1300 may be arranged outside the second side window glass 1120.
The cluster 1400 may be arranged in front of the steering wheel. The cluster 1400 may include a tachometer, a speedometer, a coolant thermometer, a fuel gauge turn indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, a hodometer, an automatic shift selector indicator, a door open warning light, an engine oil warning light, and/or a low fuel warning light.
The center fascia 1500 may include a control panel on which a plurality of buttons for adjusting an audio device, an air conditioning device, and/or a heater of a seat are disposed. The center fascia 1500 may be arranged on one side of the cluster 1400.
The passenger seat dashboard 1600 may be spaced apart from the cluster 1400 with the center fascia 1500 arranged therebetween. In some embodiments, the cluster 1400 may be arranged to correspond to a driver seat, and the passenger seat dashboard 1600 may be disposed to correspond to a passenger seat. In some embodiments, the cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat dashboard 1600 may be adjacent to the second side window glass 1120.
In one or more embodiments, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be arranged inside the vehicle 1000. In some embodiments, the display device 2 may be arranged between the side window glasses 1100 facing each other. The display device 2 may be arranged on at least one of the cluster 1400, the center fascia 1500, or the passenger seat dashboard 1600.
The display device 2 may include an organic light-emitting display device, an inorganic EL display device, a quantum dot display device, and/or the like. Hereinafter, as the display device 2 according to one or more embodiments, an organic light-emitting display device display including the light-emitting device according to the disclosure will be described as an example, but one or more suitable types (kinds) of display devices as described above may be utilized in embodiments of the disclosure.
Referring to
Referring to
Referring to
The layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region may each be formed in a certain region by utilizing one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, laser-induced thermal imaging, and/or the like.
When the layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region are each formed by vacuum deposition, the deposition may be performed at a deposition temperature in a range of about 100° C. to about 500° C., at a vacuum degree in a range of about 10−8 torr to about 10-3 torr, and at a deposition speed in a range of about 0.01 Å/sec to about 100 Å/sec, depending on a material to be included in a layer to be formed and the structure of a layer to be formed.
The term “C3-C60 carbocyclic group” as utilized herein refers to a cyclic group including (e.g., consisting of) carbon only as a ring-forming atom and having three to sixty carbon atoms, and the term “C1-C60 heterocyclic group” as utilized herein refers to a cyclic group that has one to sixty carbon atoms and further has, in addition to carbon, a heteroatom as a ring-forming atom. The C3-C60 carbocyclic group and the C1-C60 heterocyclic group may each be a monocyclic group including (e.g., consisting of) one (e.g., exactly one) ring or a polycyclic group in which two or more rings are condensed with each other. For example, the number of ring-forming atoms of the C1-C60 heterocyclic group may be from 3 to 61.
The term “cyclic group” as utilized herein may include both (e.g., simultaneously) the C3-C60 carbocyclic group and the C1-C60 heterocyclic group.
The term “π electron-rich C3-C60 cyclic group” as utilized herein refers to a cyclic group that has 3 to 60 carbon atoms and does not include *—N═*′ as a ring-forming moiety, and the term “π electron-deficient nitrogen-containing C1-C60 heterocyclic group” as utilized herein refers to a heterocyclic group that has 1 to 60 carbon atoms and includes *—N═*′ as a ring-forming moiety.
For example,
The term “cyclic group,” “C3-C60 carbocyclic group,” “C1-C60 heterocyclic group,” “π electron-rich C3-C60 cyclic group,” or “π electron-deficient nitrogen-containing C1-C60 heterocyclic group” as utilized herein may refer to a group condensed to any cyclic group, a monovalent group, or a polyvalent group (for example, a divalent group, a trivalent group, a tetravalent group, etc.) according to the structure of a formula for which the corresponding term is utilized. For example, the “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.”
Non-limiting examples of the monovalent C3-C60 carbocyclic group and the monovalent C1-C60 heterocyclic group are a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group. Non-limiting examples of the divalent C3-C60 carbocyclic group and the divalent C1-C60 heterocyclic group are a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.
The term “C1-C60 alkyl group” as utilized herein refers to a linear or branched aliphatic hydrocarbon monovalent group that has one to sixty carbon atoms, and non-limiting examples thereof are a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group. The term “C1-C60 alkylene group” as utilized herein refers to a divalent group having substantially the same structure as the C1-C60 alkyl group.
The term “C2-C60 alkenyl group” as utilized herein refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminus of a C2-C60 alkyl group, and non-limiting examples thereof are an ethenyl group, a propenyl group, a butenyl group, and/or the like. The term “C2-C60 alkenylene group” as utilized herein refers to a divalent group having substantially the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as utilized herein refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminus of a C2-C60 alkyl group, and non-limiting examples thereof are an ethynyl group, a propynyl group, and/or the like. The term “C2-C60 alkynylene group” as utilized herein refers to a divalent group having substantially the same structure as the C2-C60 alkynyl group.
The term “C1-C60 alkoxy group” as utilized herein refers to a monovalent group represented by —OA101 (wherein A101 is a C1-C60 alkyl group), and non-limiting examples thereof are a methoxy group, an ethoxy group, an isopropyloxy group, and/or the like.
The term “C3-C10 cycloalkyl group” as utilized herein refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, and/or the like. The term “C3-C10 cycloalkylene group” as utilized herein refers to a divalent group having substantially the same structure as the C3-C10 cycloalkyl group.
The term “C1-C10 heterocycloalkyl group” as utilized herein refers to a monovalent cyclic group of 1 to 10 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and non-limiting examples thereof are a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and/or the like. The term “C1-C10 heterocycloalkylene group” as utilized herein refers to a divalent group having substantially the same structure as the C1-C10 heterocycloalkyl group.
The term “C3-C10 cycloalkenyl group” as utilized herein refers to a monovalent cyclic group that has three to ten carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and non-limiting examples thereof are a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and/or the like. The term “C3-C10 cycloalkenylene group” as utilized herein refers to a divalent group having substantially the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group” as utilized herein refers to a monovalent cyclic group of 1 to 10 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and having at least one double bond in the cyclic structure thereof. Non-limiting examples of the C1-C10 heterocycloalkenyl group are a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and/or the like. The term “C1-C10 heterocycloalkenylene group” as utilized herein refers to a divalent group having substantially the same structure as the C1-C1a heterocycloalkenyl group.
The term “C6-C60 aryl group” as utilized herein refers to a monovalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms, and the term “C6-C6a arylene group” as utilized herein refers to a divalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms. Non-limiting examples of the C6-C60 aryl group are a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, and/or the like. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be condensed with each other.
The term “C1-C60 heteroaryl group” as utilized herein refers to a monovalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms. The term “C1-C60 heteroarylene group” as utilized herein refers to a divalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms. Non-limiting examples of the C1-C60 heteroaryl group are a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, and a naphthyridinyl group. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the rings may be condensed with each other.
The term “monovalent non-aromatic condensed polycyclic group” as utilized herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure as a whole. Non-limiting examples of the monovalent non-aromatic condensed polycyclic group are an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, an indeno anthracenyl group, and/or the like. The term “divalent non-aromatic condensed polycyclic group” as utilized herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed polycyclic group described above.
The term “monovalent non-aromatic condensed heteropolycyclic group” as utilized herein refers to a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings condensed to each other, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and having non-aromaticity in its entire molecular structure as a whole. Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group include a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphtho indolyl group, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indenocarbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthosilolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, and a benzothienodibenzothiophenyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as utilized herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed heteropolycyclic group described above.
The term “C6-C60 aryloxy group” as utilized herein indicates —OA102 (wherein A102 is a C6-C60 aryl group), and the term “C6-C60 arylthio group” as utilized herein indicates —SA103 (wherein A103 is a C6-C60 aryl group).
The term “C7-C60 arylalkyl group” as utilized herein refers to -A104A105 (wherein A104 is a C1-C54 alkylene group, and A105 is a C6-C59 aryl group), and the term “C2-C60 heteroarylalkyl group” as utilized herein refers to -A106A107 (wherein A106 is a C1-C59 alkylene group, and A107 is a C1-C59 heteroaryl group).
The term “R10a” as utilized herein may be:
Q1 to Q3, Q11 to Q13, Q21 to Q23 and Q31 to Q33 utilized herein may each independently be: hydrogen; deuterium; —F; —C1; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof; a C7-C60 aryl alkyl group; or a C2-C60 heteroaryl alkyl group.
The term “heteroatom” as utilized herein refers to any atom other than a carbon atom. Non-limiting examples of the heteroatom are O, S, N, P, Si, B, Ge, Se, and any combination thereof.
The term “third-row transition metal” as utilized herein includes Hf, Ta, W, Re, Os, Ir, Pt, Au, and/or the like.
“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 “biphenyl group” as utilized herein refers to “a phenyl group substituted with a phenyl group.” In some embodiments, the “biphenyl group” may be a substituted phenyl group having a C6-C60 aryl group as a substituent.
The term “terphenyl group” as utilized herein refers to “a phenyl group substituted with a biphenyl group.” In some embodiments, the “terphenyl group” may be a substituted phenyl group having, as a substituent, a C6-C60 aryl group substituted with a C6-C60 aryl group.
* and *′ as utilized herein, unless defined otherwise, each refer to a binding site to a neighboring atom in a corresponding formula or moiety.
In the present disclosure, the x-axis, y-axis, and z-axis are not limited to three axes in an orthogonal coordinate system, and may be interpreted in a broad sense including these axes. For example, the x-axis, y-axis, and z-axis may refer to those orthogonal to each other, or may refer to those in different directions that are not orthogonal to each other.
Hereinafter, compounds according to one or more embodiments and light-emitting devices according to one or more embodiments will be described in more detail with reference to the following Synthesis Examples and Examples. The wording “B was utilized instead of A” utilized in describing Synthesis Examples refers to that an identical molar equivalent of B was utilized in place of A.
3,8-dichloro-10-nitro-9H-tetrabenzo[b,d,f,h]azonine (12.0 g, 27.6 mmol), 2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (13.1 g, 41.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (2.6 g, 2.8 mmol), (2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl) SPhos (1.7 g, 4.1 mmol), and NaOtBu (10.6 g, 110.4 mmol) were placed in a reaction vessel and suspended in toluene (250 mL) under nitrogen, then heated and stirred at 120° C. for 12 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and 150 mL of distilled water was added thereto, and an organic layer was extracted utilizing ethyl acetate. The extracted organic layer was washed with saturated aqueous sodium chloride solution and dried utilizing sodium sulfate. The result obtained therefrom was subjected to column chromatography to obtain Compound IM-1a (17.8 g, 24.0 mmol) having the yield of 87%.
Compound IM-1b (17.6 g, 23.5 mmol) was obtained in the yield of 85% in substantially the same manner as in Synthesis Example 1, except that, in synthesizing Compound IM-1b, 2-(3,5-di-tert-butylphenyl-2,4,6-d3)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was utilized instead of 2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.
Compound IM-1c (17.9 g, 23.5 mmol) was obtained in the yield of 85% in substantially the same manner as in Synthesis Example 1, except that, in synthesizing Compound IM-1c, 3,8-dichloro-10-nitro-9H-tetrabenzo[b,d,f,h]azonine-1,2,4,5,6,7,11,12,13,14,15,16,17-d13 was utilized instead of 3,8-dichloro-10-nitro-9H-tetrabenzo[b,d,f,h]azonine.
Compound IM-1d (18.0 g, 22.6 mmol) was obtained in the yield of 82% in substantially the same manner as in Synthesis Example 3, except that, in synthesizing Compound IM-1d, 2-(3,5-bis(2-(methyl-d3)propan-2-yl-1,1,1,3,3,3-d6)phenyl-2,4,6-d3)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was utilized instead of 2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.
Compound IM-1e (18.0 g, 22.1 mmol) was obtained in the yield of 80% in substantially the same manner as in Synthesis Example 1, except that, in synthesizing Compound IM-1e, 2-(5-(tert-butyl)-[1,1′-biphenyl]-3-yl-2,2′,3′,4,4′,5′,6,6′-d8)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was utilized instead of 2-(3,5-di-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.
Compound IM-1f (20.1 g, 21.8 mmol) was obtained in the yield of 79% in substantially the same manner as in Synthesis Example 5, except that, in synthesizing Compound IM-1f, 2-(4′,5-di-tert-butyl-[1,1′-biphenyl]-3-yl-2,2′,3′,4,5′,6,6′-d7)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was utilized instead of 2-(5-(tert-butyl)-[1,1′-biphenyl]-3-yl-2,2′,3′,4,4′,5′,6,6′-d8)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.
Compound IM-1g (21.0 g, 22.4 mmol) was obtained in the yield of 81% in substantially the same manner as in Synthesis Example 6, except that, in synthesizing Compound IM-1g, 2-(3′-(tert-butyl)-5-(2-(methyl-d3)propan-2-yl-1,1,1,3,3,3-d6)-[1,1′-biphenyl]-3-yl-2,2′,4,4′,5′,6,6′-d7)-4,4,5,5-etramethyl-1,3,2-dioxaborolane was utilized instead of 2-(4′,5-di-tert-butyl-[1,1′-biphenyl]-3-yl-2,2′,3′,4,5′,6,6′-d7)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.
A mixture including Compound IM-1a (17.8 g, 24.0 mmol) and tin (8.5 g, 72 mmol) was placed in a reaction vessel, suspended in a mixed solution including ethanol (EtOH) (240 mL) and HCl, 37% (10.8 mL), and then heated to 80° C. and stirred at ° C. for 12 hours. After completion of the reaction, the reaction solution was cooled at room temperature, and 150 mL of distilled water was added thereto and then neutralized, and an organic layer was extracted utilizing dichloromethane. The extracted organic layer was washed with saturated aqueous sodium chloride solution and dried utilizing sodium sulfate. The result obtained therefrom was subjected to column chromatography to obtain Compound IM-2a (15.0 g, 21.1 mmol) in the yield of 88%.
Compound IM-2b (15.5 g, 21.6 mmol) was obtained in the yield of 90% in substantially the same manner as in Synthesis Example 8, except that, in synthesizing Compound IM-2b, IM-1b was utilized instead of IM-1a.
Compound IM-2c (15.8 g, 21.6 mmol) was obtained in the yield of 90% in substantially the same manner as in Synthesis Example 8, except that, in synthesizing Compound IM-2c, IM-1c was utilized instead of IM-1a.
Compound IM-2d (16.0 g, 20.9 mmol) was obtained in the yield of 87% in substantially the same manner as in Synthesis Example 8, except that, in synthesizing Compound IM-2d, IM-1d was utilized instead of IM-1a.
Compound IM-2e (15.8 g, 20.6 mmol) was obtained in the yield of 86% in substantially the same manner as in Synthesis Example 8, except that, in synthesizing Compound IM-2e, IM-1e was utilized instead of IM-1a.
Compound IM-2f (18.3 g, 20.6 mmol) was obtained in the yield of 86% in substantially the same manner as in Synthesis Example 8, except that, in synthesizing Compound IM-2f, IM-1f was utilized instead of IM-1a.
Compound IM-2g (19.0 g, 20.9 mmol) was obtained in the yield of 87% in substantially the same manner as in Synthesis Example 8, except that, in synthesizing Compound IM-2g, IM-1g was utilized instead of IM-1a.
Compound IM-2a (8.1 g, 11.4 mmol), 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole (5.4 g, 11.4 mmol), Pd2(dba)3 (0.2 g, 0.2 mmol), SPhos (1.9 g, 4.6 mmol), and NaOtertBu (1.7 g, 18.2 mmol) were placed in a reaction vessel and suspended in 114 mL of toluene, then heated and stirred at 110° C. for 4 hours. After completion of the reaction, the reaction solution was cooled at room temperature, and 300 mL of distilled water was added thereto, and an organic layer was extracted utilizing ethyl acetate. The extracted organic layer was washed with saturated aqueous sodium chloride solution and dried utilizing sodium sulfate. The result obtained therefrom was subjected to column chromatography to obtain Compound IM-3a (8.2 g, 7.4 mmol) in the yield of 65%.
Compound IM-3b (8.6 g, 7.8 mmol) was obtained in the yield of 68% in substantially the same manner as in Synthesis Example 15, except that, in synthesizing Compound IM-3b, 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d4 was utilized instead of 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole.
Compound IM-3c (8.9 g, 8.0 mmol) was obtained in the yield of 70% in substantially the same manner as in Synthesis Example 15, except that, in synthesizing Compound IM-3c, 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d4 was utilized instead of 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole, and IM-2b was utilized instead of IM-2a.
Compound IM-3d (9.0 g, 7.8 mmol) was obtained in the yield of 68% in substantially the same manner as in Synthesis Example 15, except that, in synthesizing Compound IM-3d, 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d4 was utilized instead of 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole, and IM-2e was utilized instead of IM-2a.
Compound IM-3e (9.0 g, 8.0 mmol) was obtained in the yield of 70% in substantially the same manner as in Synthesis Example 15, except that, in synthesizing Compound IM-3e, 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d4 was utilized instead of 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole, and IM-2c was utilized instead of IM-2a.
Compound IM-3f (9.5 g, 8.2 mmol) was obtained in the yield of 72% in substantially the same manner as in Synthesis Example 15, except that, in synthesizing Compound IM-3f, 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d4 was utilized instead of 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole, and IM-2d was utilized instead of IM-2a.
Compound IM-3g (9.4 g, 7.3 mmol) was obtained in the yield of 64% in substantially the same manner as in Synthesis Example 15, except that, in synthesizing Compound IM-3g, 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d4 was utilized instead of 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole, and IM-2f was utilized instead of IM-2a.
Compound IM-3h (10.1 g, 7.8 mmol) was obtained in the yield of 68% in substantially the same manner as in Synthesis Example 15, except that, in synthesizing Compound IM-3h, 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d4 was utilized instead of 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole, and IM-2g was utilized instead of IM-2a.
Compound IM-3i (9.1 g, 7.4 mmol) was obtained in the yield of 65% in substantially the same manner as in Synthesis Example 15, except that, in synthesizing Compound IM-3i, 2-((5-bromo-2-(methyl-d3)-[1,1′-biphenyl]-3-yl-2′,3′,4′,5′,6′-d5)oxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d4 was utilized instead of 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole, and IM-2c was utilized instead of IM-2a.
Compound IM-3j (10.0 g, 7.2 mmol) was obtained in the yield of 63% in substantially the same manner as in Synthesis Example 15, except that, in synthesizing Compound IM-3j, 2-((5-bromo-2-(methyl-d3)-[1,1′-biphenyl]-3-yl-2′,3′,4′,5′,6′-d5)oxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d4 was utilized instead of 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole, and IM-2g was utilized instead of IM-2a.
Compound IM-3a (8.2 g, 7.4 mmol), triethyl orthoformate (74 mL, 443 mmol), and HCl (37%) were placed in a reaction vessel and heated at 80° C. and stirred for 12 hours. After completion of the reaction, the reaction solution was cooled at room temperature, and the resulting solid was filtered and washed with ether, and the washed solid was dried to obtain Intermediate IM-4a (8.0 g, 7.0 mmol) in the yield of 95%. Subsequently, Intermediate IM-4a (8.0 g, 7.0 mmol), dichloro(1,5-cyclooctadiene)platinum (2.8 g, 7.6 mmol), and NaOAc (1.7 g, 20.7 mmol) were suspended in 150 mL of 1,4-dioxane, and then, heated and stirred at 120° C. for 72 hours. After completion of the reaction, the reaction solution was cooled at room temperature, and 150 mL of distilled water was added thereto, and an organic layer was extracted utilizing ethyl acetate. The extracted organic layer was washed with saturated aqueous NaCl solution and dried utilizing MgSO4. The result obtained therefrom was subjected to column chromatography to obtain Compound BD01 (2.7 g, 2.1 mmol) in the yield of 30%.
IM-4b (8.1 g, 7.0 mmol) was obtained in the yield of 95%, and from IM-4b, Compound BD02 (2.9 g, 2.2 mmol) was obtained in the yield of 32% in substantially the same manner as in Synthesis Example 25, except that, in synthesizing Compound BD02, IM-3b was utilized instead of IM-3a.
IM-4c (8.1 g, 7.0 mmol) was obtained in the yield of 95%, and from IM-4c, Compound BD113 (2.8 g, 2.1 mmol) was obtained in the yield of 32% in substantially the same manner as in Synthesis Example 25, except that, in synthesizing Compound BD113, IM-3c was utilized instead of IM-3a.
IM-4e (8.3 g, 7.0 mmol) was obtained in the yield of 95%, and from IM-4e, Compound BD114 (2.8 g, 2.1 mmol) was obtained in the yield of 31% in substantially the same manner as in Synthesis Example 25, except that, in synthesizing Compound BD114, IM-3e was utilized instead of IM-3a.
IM-4d (8.4 g, 7.0 mmol) was obtained in the yield of 95%, and from IM-4d, Compound BD117 (3.0 g, 2.2 mmol) was obtained in the yield of 31% in substantially the same manner as in Synthesis Example 25, except that, in synthesizing Compound BD117, IM-3d was utilized instead of IM-3a.
IM-4f (8.4 g, 7.0 mmol) was obtained in the yield of 95%, and from IM-4f, BD115 (3.0 g, 2.2 mmol) was obtained in the yield of 32% in substantially the same manner as in Synthesis Example 25, except that, in synthesizing Compound BD115, IM-3f was utilized instead of IM-3a.
IM-4g (9.3 g, 7.0 mmol) was obtained in the yield of 95%, and from IM-4g, BD118 (2.9 g, 2.0 mmol) was obtained in the yield of 31% in substantially the same manner as in Synthesis Example 25, except that, in synthesizing Compound BD118, IM-3g was utilized instead of IM-3a.
IM-4h (9.4 g, 7.0 mmol) was obtained in the yield of 95%, and from IM-4h, BD119 (2.7 g, 1.8 mmol) was obtained in the yield of 31% in substantially the same manner as in Synthesis Example 25, except that, in synthesizing Compound BD119, IM-3h was utilized instead of IM-3a.
IM-4i (8.9 g, 7.0 mmol) was obtained in the yield of 95% and from IM-4i, BD116 (3.3 g, 2.2 mmol) was obtained in the yield of 32% in substantially the same manner as in Synthesis Example 25, except that, in synthesizing Compound BD116, IM-3i was utilized instead of IM-3a.
IM-4j (10.0 g, 7.0 mmol) was obtained in the yield of 95%, and from IM-4j, BD120 (2.8 g, 1.8 mmol) was obtained in the yield of 25% in substantially the same manner as in Synthesis Example 25, except that, in synthesizing Compound BD120, IM-3j was utilized instead of IM-3a.
1H nuclear magnetic resonance spectroscopy (NMR) and mass spectroscopy/fast atom bombardment (MS/FAB) of the compounds synthesized according to Synthesis Examples are shown in Table 1. Synthesis methods of compounds other than the compounds synthesized in Synthesis Examples above may be easily recognized by those skilled in the art by referring to the synthesis paths and source materials.
1H NMR (CDCl3, 500 MHz)
The HOMO and LUMO energy levels of each of Compounds BD01, BD02, BD113 to BD120, and A to B were evaluated according to the method in Table 2, and results thereof are shown in Table 3.
Polymethyl methacrylate (PMMA) in a CH2Cl2 solution was mixed with Compound BD01 (4 wt % compared to PMMA), and a result therefrom was applied on a quartz substrate utilizing a spin coater, heat treated in an oven at 80° C., and then cooled to room temperature, thereby producing Film BD01 having a thickness of 40 nm. Films BD02, BD113, BD114, BD115, BD116, BD117, BD118, BD119, BD120, A, and B were each manufactured in substantially the same manner as utilized to produce Film BD01, except that Compounds BD02, BD113, BD114, BD115, BD116, BD117, BD118, BD119, BD120, A, and B were respectively utilized instead of Compound BD01.
The emission spectrum of each of Films BD01, BD02, BD113, BD114, BD115, BD116, BD117, BD118, BD119, BD120, A, and B was measured utilizing a Quantaurus-QY Absolute PL quantum yield spectrometer (a xenon light source) of the company of Hamamatsu, equipped with a monochromator, a photonic multichannel analyzer, and an integrating sphere, and utilizing photoluminescence quantum yield (PLQY) measurement software (Hamamatsu Photonics, Ltd., Shizuoka, Japan). During the measurement, an excitation wavelength was scanned from 320 nm to 380 nm at intervals of 10 nm, and an emission spectrum measured at the excitation wavelength of 340 nm was taken to obtain a maximum emission wavelength (emission peak wavelength) and FWHM of an organometallic compound included in each film, which are shown in Table 4.
Subsequently, the luminous quantum efficiency of each of Films BD01, BD02, BD113, BD114, BD115, BD116, BD117, BD118, BD119, BD120, A, and B was measured utilizing a Quantaurus-QY Absolute PL quantum yield spectrometer of the company of Hamamatsu by scanning at 10 nm intervals from 300 nm to 380 nm, PLQY measured at an excitation wavelength of 330 nm was taken, and as a result, the luminescence quantum efficiency of the organometallic compound contained in each film was calculated and is summarized in Table 4.
From Table 4, it was confirmed that Compounds BD01, BD02, BD113, BD114, BD115, BD116, BD117, BD118, BD119, and BD120 each emit blue light while having equal or superior PLOY and relatively equal or smaller FWHM compared to Compounds A and B.
The PL spectrum of each of Films BD01, BD02, BD113, BD114, BD115, BD116, BD117, BD118, BD119, BD120, A, and B was evaluated at room temperature by utilizing FluoTime 300, which is a time-resolved photoluminescence (TRPL) measurement system of the company of PicoQuant, and PLS340 (excitation wavelength=340 nanometers, spectral width=20 nanometers), which is a pumping source of the company of PicoQuant, and then, the wavelength of the main peak of the spectrum was determined, and the number of photons emitted at the wavelength of the main peak from each film by the photon pulse (pulse width=500 picoseconds) applied by PLS340 to each film was repeatedly measured over time based on time-correlated single photon counting (TCSPC) to obtain a TRPL curve that may be sufficiently fitted was obtained. Results obtained therefrom were fitted with one or more exponential decay functions to obtain Tdecay(Ex), that is, the decay time (decay) of each of Films BD01, BD02, BD113, BD114, BD115, BD116, BD117, BD118, BD119, BD120, A, and B. Results thereof are shown in Table 5. A function utilized for fitting is as shown in Equation 20, and from among Tdecay values obtained from each exponential decay function utilized for fitting, the largest Tdecay was obtained as Tdecay(Ex). In this regard, a similar measurement was performed during the same amount of measurement time, as that for obtaining the TRPL curve, in the dark state (in which pumping signals entering a film are blocked) to obtain a baseline or a background signal curve for utilization as a baseline for fitting.
From Table 5, it was confirmed that Compounds BD01, BD02, BD113, BD114, BD115, BD116, BD117, BD118, BD119, and BD120 each have equal or longer luminescence decay times (that is, lower luminescence transition rate (Kr)) than that of Compounds A and B.
For each of Compounds A, B, BD01, BD113, BD115, and BD116, thermo gravimetric analysis (TGA) under vacuum (temperature range: 0° C. to 600° C. (10° C./min), pan type or kind: Pt Pan in disposable Al Pan) was performed to evaluate the temperature at which 10 wt % of weight loss occurred (V-TGA_10 wt % loss, ° C.) and the temperature at which 50 wt % of weight loss occurred (V-TGA_50 wt % loss, ° C.) for each compound. Results thereof are shown in Table 6.
From Table 6, it can be seen that Compounds BD01, BD113, BD115, and BD116 each have excellent or suitable heat resistance, as the V-TGA_10 wt % loss and V-TGA_50 wt % loss of each of Compounds BD01, BD113, BD115, and BD116 occurred at a higher temperature compared to Compound A.
The phase transition of each of Compounds A, B, BD01, BD113, BD115, and BD116 was evaluated utilizing SETSYS evolution TG-DTA instrument of the company of Setaram, and as a result, the temperature of each of Compounds A, B, BD01, BD113, BD115, and BD116 at a vaporization pressure (6.4×10−4 Torr) was evaluated and is summarized in Table 7.
From Table 7, it can be seen that each of Compounds BD01, BD113, BD115, and BD116 has a lower phase transition temperature compared Compounds A and B, and thus has excellent or suitable heat resistance.
The purity of each of Compounds A, B, BD01, BD113, BD115, and BD116 was measured utilizing high performance liquid chromatography (HPLC) to evaluate P(0 Hr) (%) of each compound.
Subsequently, each of Compounds A, B, BD01, BD113, BD115, and BD116 was heat-treated for 360 hours in a chamber where the internal temperature was maintained at the vaporization pressure (6.4×10−4 Torr), then collected, and then again subjected to HPLC to obtain P(360 Hr) (%) of each compound.
As a result, the change in purity (%) after heat treatment for each compound, P(360 Hr)−P(0 Hr) (%), was evaluated, and results thereof are shown in Table 8.
From Table 8, it can be seen that each of Compounds BD01, BD113, BD115, and BD116 has excellent or suitable heat resistance, because the absolute value of change in purity after heat treatment is small compared to Compounds A and B.
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 with isopropyl alcohol and (then with) pure water each for 5 minutes, cleaned 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.
On the hole transport layer, Compound BD01 (the organometallic compound represented by Formula 1), Compound ETH2 (second compound), and Compound HTH29 (third compound) were vacuum deposited on the hole transport layer to form an emission layer having a thickness of 350 Å. Herein, the amount of compound BD01 was adjusted to be 13 wt % per total weight (100 wt %) of the emission layer, and the weight ratio of compound ETH2 and compound HTH29 was adjusted to be 3.5:6.5.
Compound ETH34 was vacuum-deposited on the emission layer to form a hole-blocking layer having a thickness of 50 Å, and ET46 and LiQ were vacuum-deposited on the hole-blocking layer at a weight ratio of 4:6 to form an electron transport layer having a thickness of 310 Å. Next, Yb was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 15 Å, and then Mg was vacuum-deposited thereon to form a cathode having a thickness of 800 Å, thereby completing manufacture of an organic light-emitting device.
Organic light-emitting devices were each manufactured in substantially the same manner as in Example 1, except that, in forming an emission layer, the organometallic compound represented by Formula 1, the second compound, the third compound, and/or the fourth compound, and the amounts thereof shown in Table 9 were utilized. The weight in parentheses in Table 9 indicates the weight of a compound based on 100 wt % of the emission layer.
The driving voltage (V) at 1000 cd/m2, color purity (CIEx,y), luminescence efficiency (cd/A), and color conversion efficiency (cd/A/y), maximum emission wavelength (nm), and lifespan (T95) of each of the organic light-emitting devices manufactured in Examples 1 to 14, and Comparative Examples A and B. Results thereof are shown in Table 10. Lifespan (T95) in Table 10 indicates the time (Hr) taken to reach 95% luminance compared to the initial luminance.
From Table 10, it was confirmed that, compared to the organic light-emitting devices of Comparative Examples A and B, the organic light-emitting devices of Examples 1 to 14 each emit deep blue light, and have excellent or suitable driving voltage, excellent or suitable color purity, excellent or suitable luminescence efficiency, and excellent or suitable color conversion efficiency, and excellent or suitable lifespan characteristics.
Organic light-emitting devices were manufactured in substantially the same manner as in Example 1, except that, in forming an emission layer, the organometallic compound represented by Formula 1 was changed as shown in Table 11. “Heat-treated compound” in Table 11 refers to, as in Evaluation Example 6, a compound collected after heat treatment for 360 hours in a chamber where the internal temperature was maintained at the vaporization pressure (6.4×10−4 Torr).
The luminescence efficiency (cd/A) 1000 cd/m2 and lifespan (T95) of each of the organic light-emitting devices manufactured in Comparative Example A-heat, Comparative Example B-heat and Examples 1-heat, 3-heat, 5-heat, and 6-heat were each measured in substantially the same manner as in Evaluation Example 7. Results thereof are shown in Table 11. Lifespan (T95) in Table 11 indicates the time (Hr) taken to reach 95% luminance compared to the initial luminance.
Then, “(luminescence efficiency of Comparative Example A-heat-luminescence efficiency of Comparative Example A)/luminescence efficiency of Comparative Example A×100” (%) and “(lifespan of Comparative Example A-heat-lifespan of Comparative Example A)/lifespan of Comparative Example A×100” (%) were evaluated. Results thereof are shown in 11. This evaluation was performed on each the organic light-emitting devices utilizing Compounds BD01, BD113, BD115, and BD116, and results thereof are shown in Table 11.
From Table 11, it can be seen that the absolute values of luminescence efficiency change rate and lifespan change rate after heat treatment of the organic light-emitting device utilizing each of Compounds BD01, BD113, BD115 and BD116 were smaller than those of the organic light-emitting device utilizing Compounds A and B. Accordingly, it can be seen that an organic light-emitting device manufactured (for example, manufactured by a deposition process) utilizing the organometallic compound represented by Formula 1 can have excellent or suitable luminescence efficiency and lifespan characteristics at the same time.
By utilizing organometallic compounds of the present disclosure, light-emitting devices and high-quality electronic apparatuses including the light-emitting device, having reduced driving voltage, improved color purity and efficiency, and increased lifespan, may be manufactured.
In the present disclosure, it will be understood that the term “comprise(s),” “include(s),” or “have/has” specifies the presence of stated features, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, and/or groups thereof.
Throughout the present disclosure, when a component such as a layer, a film, a region, or a plate is mentioned to be placed “on” another component, it will be understood that it may be directly on another component or that another component may be interposed therebetween. In some embodiments, “directly on” may refer to that there are no additional layers, films, regions, plates, etc., between a layer, a film, a region, a plate, etc. and the other part. For example, “directly on” may refer to two layers or two members are disposed without utilizing an additional member such as an adhesive member therebetween.
In the present disclosure, although the terms “first,” “second,” etc., may be utilized herein to describe one or more elements, components, regions, and/or layers, these elements, components, regions, and/or layers should not be limited by these terms. These terms are only utilized to distinguish one component from another component.
As utilized herein, the singular forms “a,” “an,” “one,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise. Further, the use of “may” when describing embodiments of the present disclosure refers to “one or more embodiments of the present disclosure”.
As utilized herein, the terms “substantially,” “about,” or similar terms 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. “About” as used herein, is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±30%, 20%, 10%, 5% of the stated value.
Any numerical range recited herein is intended to include all sub-ranges of the same numerical precision subsumed within the recited range. For example, a range of “1.0 to 10.0” is intended to include all subranges between (and including) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, 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. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in the present disclosure is intended to include all higher numerical limitations subsumed therein. Accordingly, Applicant reserves the right to amend the disclosure, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein.
The light-emitting device, the light-emitting apparatus, the display device, the electronic apparatus, the electronic device, or any other relevant devices or components according to embodiments of the present disclosure described herein may be implemented utilizing any suitable hardware, firmware (e.g., an application-specific integrated circuit), software, or a combination of software, firmware, and hardware. For example, the various components of the device may be formed on one integrated circuit (IC) chip or on separate IC chips. Further, the various components of the device may be implemented on a flexible printed circuit film, a tape carrier package (TCP), a printed circuit board (PCB), or formed on one substrate. Further, the various components of the device may be a process or thread, running on one or more processors, in one or more computing devices, executing computer program instructions and interacting with other system components for performing the various functionalities described herein. The computer program instructions are stored in a memory which may be implemented in a computing device using a standard memory device, such as, for example, a random access memory (RAM). The computer program instructions may also be stored in other non-transitory computer readable media such as, for example, a CD-ROM, flash drive, or the like. Also, a person of skill in the art should recognize that the functionality of various computing devices may be combined or integrated into a single computing device, or the functionality of a particular computing device may be distributed across one or more other computing devices without departing from the scope of the embodiments of the present disclosure.
It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the drawings, it will be understood by those of ordinary skill in the art that one or more suitable changes in form and details may be made therein without departing from the spirit and scope as defined by the appended claims and equivalents thereof.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2023-0133693 | Oct 2023 | KR | national |
