Patent Application
20240292742
This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0011945, filed on Jan. 30, 2023, in the Korean Intellectual Property Office, the content of which is incorporated by reference herein in its entirety.
One or more embodiments of the present disclosure relate to a light-emitting device including a heterocyclic compound, an electronic apparatus including the light-emitting device, and the heterocyclic compound.
Among light-emitting devices, self-emissive devices (e.g., organic light-emitting devices) have relatively wide viewing angles, high contrast ratios, short response times, and excellent or suitable characteristics in terms of luminance, driving voltage, and response speed.
A light-emitting device may have a structure in which 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 may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, may recombine in the emission layer to produce excitons. These excitons may transition (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 a heterocyclic compound, an electronic apparatus including the light-emitting device, and the heterocyclic 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 present disclosure.
According to one or more embodiments of the present disclosure, a light-emitting device includes:
at least one selected from among A1 to A3 may be a C5-C10 cycloalkyl group unsubstituted or substituted with at least one R10a,
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 heterocyclic 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 embodiments of the present disclosure 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 of Formula 1 may be as described herein.
In one or more embodiments,
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. For example, the hole blocking layer may directly contact the emission layer.
In one or more embodiments, the heterocyclic compound may be included in the interlayer, for example, as a first compound.
In one or more embodiments, the heterocyclic compound may be included in the emission layer.
In one or more embodiments, the emission layer may further include a transition metal-containing compound, a delayed fluorescence compound, or any combination thereof. In the emission layer, the heterocyclic compound, the transition metal-containing compound, and the delayed fluorescence compound may be different from one another.
In one or more embodiments, the emission layer may further include a second compound including a group represented by Formula 2. In the emission layer, the second compound may be different from the heterocyclic compound.
In Formula 2,
In one or more embodiments, the emission layer may further include the transition metal-containing compound, the delayed fluorescence compound, and the second compound, in addition to the heterocyclic compound. In the emission layer, the heterocyclic compound, the transition metal-containing compound, the delayed fluorescence compound, and the second compound may be different from one another.
In one or more embodiments, the emission layer may further include a light-emitting material.
In one or more embodiments, the light-emitting material may include the transition metal-containing compound, the delayed fluorescence compound, or any combination thereof. Among the light-emitting materials, the heterocyclic compound, the transition metal-containing compound, and the delayed fluorescence compound may be different from one another.
In one or more embodiments, the light-emitting material may further include the second compound. Among the light-emitting materials, the heterocyclic compound and the second compound may be different from each other.
In one or more embodiments, the light-emitting material may further include the transition metal-containing compound, the delayed fluorescence compound, and the second compound, in addition to the heterocyclic compound. Among the light-emitting materials, the heterocyclic compound, the transition metal-containing compound, the delayed fluorescence compound, and the second compound may be different from one another.
In one or more embodiments, the transition metal-containing compound may include platinum (Pt).
In one or more embodiments, the transition metal-containing compound may include platinum (Pt) and a tetradentate ligand bonded to the platinum, and the platinum and one of carbon atoms of the tetradentate ligand may be bonded to each other via a coordinate bond.
In one or more embodiments, the transition metal-containing compound may be a carbene-containing compound.
In one or more embodiments, the transition metal-containing compound may be a compound represented by Formula 3:
Details of Formula 3 may be as described herein.
In one or more embodiments, the delayed fluorescence compound may be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms. The delayed fluorescence compound may serve to improve the color purity, luminescence efficiency, and lifespan characteristics of the light-emitting device.
In one or more embodiments, a difference between a triplet energy level (eV) of the delayed fluorescence compound and a singlet energy level (eV) of the delayed fluorescence compound may be greater than or equal to 0 eV and less than or equal to 0.5 eV (or, greater than or equal to 0 eV and less than or equal to 0.3 eV).
In one or more embodiments, the delayed fluorescence compound may be a C8-C60 polycyclic group-containing compound including at least two condensed cyclic groups that share boron (B) (e.g., as a first ring and a second ring).
In one or more embodiments, the delayed fluorescence compound may include a condensed ring in which at least one third ring is 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 delayed fluorescence compound may be a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof:
In Formulae 502 and 503,
In one or more embodiments, the second compound may include a compound represented by Formula 2-1, a compound represented by Formula 2-2, a compound represented by Formula 2-3, a compound represented by Formula 2-4, a compound represented by Formula 2-5, or any combination thereof:
In Formulae 2-1 to 2-5,
In one or more embodiments, the following compounds may be excluded from the second compound:
For example, in some embodiments, the second compound may not include(e.g., may exclude) the compound represented by Formula 2-1 described herein.
Details of the heterocyclic compound, the transition metal-containing compound, the delayed fluorescence compound, and the second compound may be as described herein.
In one or more embodiments, the heterocyclic compound, the transition metal-containing compound, the delayed fluorescence compound, the second compound, or any combination thereof may include at least one deuterium.
For example, in some embodiments, the heterocyclic compound may include at least one deuterium.
For example, in some embodiments, the transition metal-containing compound, the delayed fluorescence compound, the second compound, or any combination thereof may include at least one deuterium.
In one or more embodiments, the heterocyclic compound may include at least one silicon.
In one or more embodiments, the second compound may include at least one silicon.
In one or more embodiments, the light-emitting device (for example, the emission layer in the light-emitting device) may further include the transition metal-containing compound, in addition to the heterocyclic compound. At least one selected from among the heterocyclic compound and the transition metal-containing compound may include at least one deuterium.
In one or more embodiments, the light-emitting device (for example, the emission layer in the light-emitting device) may further include the delayed fluorescence compound, in addition to the heterocyclic compound, and at least one selected from among the heterocyclic compound and the delayed fluorescence compound may include at least one deuterium.
In one or more embodiments, the light-emitting device (for example, the emission layer in the light-emitting device) may further include the transition metal-containing compound and the delayed fluorescence compound, in addition to the heterocyclic compound, and at least one selected from among the heterocyclic compound, the transition metal-containing compound, and the delayed fluorescence compound may include at least one deuterium.
In one or more embodiments, the light-emitting device (for example, the emission layer in the light-emitting device) may further include the second compound, in addition to the heterocyclic compound, and at least one selected from among the heterocyclic compound and the second compound may include at least one deuterium.
In one or more embodiments, the light-emitting device (for example, the emission layer in the light-emitting device) may further include the transition metal-containing compound, the delayed fluorescence compound, and the second compound, in addition to the heterocyclic compound, and at least one selected from among the heterocyclic compound, the transition metal-containing compound, the delayed fluorescence compound, and the second compound may include at least one deuterium.
In one or more embodiments, the heterocyclic compound and the second compound may form an exciplex. The heterocyclic compound and the second compound may each include at least one deuterium.
In one or more embodiments, the emission layer of the light-emitting device may include: i) the heterocyclic compound and the second compound; and ii) the transition metal-containing compound or the delayed fluorescence compound.
In one or more embodiments, the emission layer may include a host and a dopant, and the heterocyclic compound may be included in the host. For example, the heterocyclic compound may serve as a host.
In one or more 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, light emitted from the emission layer may have a maximum emission wavelength in a range of about 400 nm to about 500 nm, about 410 nm to about 490 nm, about 420 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 light-emitting device may satisfy at least one selected from among Conditions 1 to 4:
lowest unoccupied molecular orbital (LUMO) energy level (eV) of second compound >LUMO energy level (eV) of transition metal-containing compound
LUMO energy level (eV) of transition metal-containing compound >LUMO energy level (eV) of heterocyclic compound
highest occupied molecular orbital (HOMO) energy level (eV) of transition metal-containing compound >HOMO energy level (eV) of second compound
HOMO energy level (eV) of second compound >HOMO energy level (eV) of heterocyclic compound
Each of the HOMO energy level and LUMO energy level of each of the heterocyclic compound, the second compound, and the transition metal-containing compound may be a negative value, and may be measured according to a suitable method.
In one or more embodiments, the absolute value of a difference between the LUMO energy level of the transition metal-containing compound and the LUMO energy level of the heterocyclic compound may be greater than or equal to 0.1 eV and less than or equal to 1.0 eV or the absolute value of a difference between the LUMO energy level of the transition metal-containing compound and the LUMO energy level of the second compound may be greater than or equal to 0.1 eV and less than or equal to 1.0 eV, and the absolute value of a difference between the HOMO energy level of the transition metal-containing compound and the HOMO energy level of the heterocyclic compound may be less than or equal to 1.25 eV (for example, less than or equal to 1.25 eV and greater than or equal to 0.2 eV) or the absolute value of a difference between the HOMO energy level of the transition metal-containing compound and the HOMO energy level of the second compound may be less than or equal to 1.25 eV (for example, less than or equal to 1.25 eV and greater than or equal to 0.2 eV).
When the relationships described above are satisfied, a balance between holes and electrons injected into the emission layer may be obtained.
In one or more embodiments, the light-emitting device may have a structure of a first embodiment or a second embodiment.
According to the first embodiment, the heterocyclic compound may be included in the emission layer in the interlayer of the light-emitting device, wherein the emission layer may further include the transition metal-containing compound, and the emission layer may be to emit phosphorescence or fluorescence emitted from the transition metal-containing compound. For example, according to the first embodiment, the heterocyclic compound may be a host, and the transition metal-containing compound may be a dopant or an emitter. For example, the transition metal-containing compound may be a phosphorescent dopant or a phosphorescent emitter.
The phosphorescence or fluorescence emitted from the transition metal-containing compound may be blue light.
In some embodiments, the emission layer may further include an auxiliary dopant. The auxiliary dopant may serve to improve luminescence efficiency from the transition metal-containing compound by effectively transferring energy to the transition metal-containing compound as a dopant or an emitter.
The auxiliary dopant may be different from the transition metal-containing compound and the heterocyclic compound.
For example, in some embodiments, the auxiliary dopant may be a delayed fluorescence-emitting compound.
In one or more embodiments, the auxiliary dopant may be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.
The emission layer may further include at least one host different from the heterocyclic compound, the transition metal-containing compound, and the auxiliary dopant. For example, the emission layer may further include the second compound as a host.
According to the second embodiment, the heterocyclic compound may be included in the emission layer in the interlayer of the light-emitting device, wherein the emission layer may further include the transition metal-containing compound and a dopant, the heterocyclic compound, the transition metal-containing compound, and the dopant may be different from one another, and the emission layer may be to emit phosphorescence or fluorescence (for example, delayed fluorescence) emitted from the dopant. For example, according to the second embodiment, the heterocyclic compound may be a host, and the transition metal-containing compound may serve not as a dopant, but as an auxiliary dopant that transfers energy to the dopant (or an emitter).
In one or more embodiments, in the second embodiment, the heterocyclic compound may be a host, and the transition metal-containing compound may serve as an emitter and also as an auxiliary dopant that transfers energy to the dopant (or an emitter).
For example, the 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 transition metal-containing compound) 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 one or more embodiments, the emission layer may further include at least one host different from the heterocyclic compound, the transition metal-containing compound, and the dopant (or the emitter). For example, the emission layer may further include the second compound as a host.
The blue light in the first embodiment and the second embodiment may each be blue light having a maximum emission wavelength in a range of about 400 nm to about 500 nm, about 410 nm to about 490 nm, about 420 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.
The auxiliary dopant in the first embodiment may include, for example, the delayed fluorescence compound represented by Formula 502 or 503.
In one or more embodiments, the host in the first embodiment and the second embodiment may further include 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 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 selected from among a first capping layer arranged outside (e.g., on) the first electrode and a second capping layer arranged outside (e.g., on) the second electrode, and the heterocyclic compound represented by Formula 1 may be included in at least one selected from among the first capping layer and the second capping layer. Details of the first capping layer and/or the second capping layer may be as described herein.
In one or more embodiments, the light-emitting device may include:
The expression “(an interlayer and/or a capping layer) include(s) at least one heterocyclic compound represented by Formula 1” as utilized herein may include an embodiment in which “(an interlayer and/or a capping layer) include(s) identical heterocyclic compounds represented by Formula 1” and an embodiment in which “(an organic layer) includes two or more different heterocyclic compounds represented by Formula 1.”
For example, in some embodiments, the interlayer and/or the capping layer may include Compound 1 only as the heterocyclic 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 heterocyclic 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. 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 of the thin-film transistor. In one or more 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. Details of the electronic apparatus may be as described herein.
According to one or more embodiments of the present disclosure, electronic equipment may include the light-emitting device.
For example, in one or more embodiments, the electronic equipment may be at least one selected from 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, and a signboard.
According to one or more embodiments of the present disclosure, the heterocyclic compound represented by Formula 1 is provided. Details of Formula 1 may be as described herein.
Synthesis methods of the heterocyclic compound may be recognized by one of ordinary skill in the art by referring to Synthesis Examples and/or Examples provided herein.
In Formula 1, X1 may be C(Y1) or N, X2 may be C(Y2) or N, X3 may be C(Y3) or N, and at least one selected from among X1 to X3 may be N.
In one or more embodiments, X1 to X3 may each be N.
In one or more embodiments, Y1 to Y3 may each independently be —Si(A1)(A2)(A3), 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), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2).
A1 to A3, R10a, and Q1 to Q3 may each be as defined herein.
In one or more embodiments, Y1 to Y3 may each independently be:
Q1 to Q3 and Q31 to Q33 may each be as defined herein.
In Formula 1, ring CY1 to ring CY3 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
In one or more embodiments, ring CY1 to ring CY3 may each independently be:
In one or more embodiments, ring CY1 to ring CY3 may each independently be:
In one or more embodiments, ring CY1 to ring CY3 may each independently be a benzene group or a carbazole group.
In Formula 1, R1 to R3 may each independently be —Si(A1)(A2)(A3), 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), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2).
In one or more embodiments, A1 to A3 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, or a C6-C60 arylthio group unsubstituted or substituted with at least one R10a.
R10a and Q1 to Q3 may each be as defined herein.
In one or more embodiments, at least one selected from among R1 to R3 may be —Si(A1)(A2)(A3).
In one or more embodiments, at least one selected from among A1 to A3 may be a C3-C10 cycloalkyl group unsubstituted or substituted with at least one R10a.
R10a may be as defined herein.
In one or more embodiments, R1 to R3 may each independently be:
Q1 to Q3 and Q31 to Q33 may each be as defined herein.
In one or more embodiments, R1 to R3 may each independently be:
—Si(A1)(A2)(A3);
In one or more embodiments, R1 to R3 may each independently be —Si(A1)(A2)(A3), hydrogen, or deuterium.
In one or more embodiments, one or two selected from among R1 to R3 may each be —Si(A1)(A2)(A3), and the remaining one or ones of R1 to R3 may each not be —Si(A1)(A2)(A3).
In one or more embodiments, at least one selected from among R1 to R3 may be deuterium.
In one or more embodiments, A1 to A3 may each independently be:
Q31 to Q33 may each be as defined herein.
In one or more embodiments, A1 to A3 may each independently be:
In one or more embodiments, A1 to A3 may each independently be: a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a pyrrolyl group, an indolyl group, a carbazolyl group, a furanyl group, a benzofuranyl group, a dibenzofuranyl group, a thiophenyl group, a benzothiophenyl group, a dibenzothiophenyl group, a silolyl group, a benzosilolyl group, or a dibenzosilolyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a phenyl group, a biphenyl group, or any combination thereof.
In one or more embodiments, at least one selected from among A1 to A3 may be a cyclohexyl group unsubstituted or substituted with at least one deuterium.
In one or more embodiments, at least one selected from among A1 to A3 may be substituted with deuterium.
In Formula 1, a1 to a3 indicate the number of R1 to the number of R3, respectively, and may each independently be an integer from 1 to 20. When a1 is 2 or more, two or more of R1(s) may be identical to or different from each other, when a2 is 2 or more, two or more of R2(s) may be identical to or different from each other, and when a3 is 2 or more, two or more of R3(s) may be identical to or different from each other.
In one or more embodiments, the heterocyclic compound represented by Formula 1 may be represented by one selected from among Formulae 1(1) to 1(4):
In Formulae 1(1) to 1(4),
In one or more embodiments, the heterocyclic compound represented by Formula 1 may be represented by one selected from among Formulae 1-1(1) to 1-1(6):
In Formulae 1-1(1) to 1-1(6),
Unless defined otherwise, for example, R10a in the description of Formula 1 may be:
Unless defined otherwise, for example, Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 in the description of 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; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; or 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.
In the heterocyclic compound represented by Formula 1, at least one selected from among R1 to R3 which are respectively substituents of ring CY1 to ring CY3 is —Si(A1)(A2)(A3), wherein A1 to A3 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, or a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, and at least one selected from among A1 to A3 is a C3-C10 cycloalkyl group unsubstituted or substituted with at least one R10a.
Accordingly, due to the C3-C10 cycloalkyl group which is a substituent capable of reducing interaction with a dopant without reducing the triplet (T1) energy level while realizing a low refractive index, the heterocyclic compound represented by Formula 1 may realize a low refractive index and a high triplet (T1) energy level, and thus may have improved light efficiency and excellent or suitable color coordinate characteristics compared to suitable compounds. In some embodiments, due to the increased light efficiency, currents required for devices to realize the same luminance may be reduced, and thus, excellent or suitable lifespan characteristics may be obtained.
Accordingly, when the heterocyclic compound represented by Formula 1 is applied to an emission layer (particularly, as a host) of a light-emitting device, luminescence efficiency and color purity may be increased, and device lifespan may be improved. Thus, due to the utilization of the heterocyclic compound, an electronic device (for example, an organic light-emitting device) having characteristics of high efficiency, high color purity, and long lifespan may be realized.
In Formula 2,
In Formulae 2-1 to 2-5,
In Formulae 2-1 to 2-5, a71 to a74 indicate the number of R71 to the number of R74, respectively, and may each independently be an integer from 0 to 20. When a71 is 2 or more, two or more of R71(s) may be identical to or different from each other, when a72 is 2 or more, two or more of R72(s) may be identical to or different from each other, when a73 is 2 or more, two or more of R73(s) may be identical to or different from each other, and when a74 is 2 or more, two or more of R74(s) may be identical to or different from each other. In some embodiments, a71 to a74 may each independently be an integer from 0 to 8.
In Formulae 2-1 to 2-5, in one or more embodiments, L81 to L85 may each independently be:
Q4, Q5, and Q31 to Q33 may each independently be hydrogen, deuterium, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group.
In one or more embodiments, a group represented by
in Formulae 2-1 and 2-2 may be a group represented by one selected from among Formulae CY71-1(1) to CY71-1(8), and/or
in Formulae 2-1 and 2-3 may be a group represented by one selected from among Formulae CY71-2(1) to CY71-2(8), and/or
in Formulae 2-2 and 2-4 may be a group represented by one selected from among Formulae CY71-3(1) to CY71-3(32), and/or
in Formulae 2-3 to 2-5 may be a group represented by one selected from among Formulae CY71-4(1) to CY71-4(32), and/or
in Formula 2-5 may be a group represented by one selected from among Formulae CY71-5(1) to CY71-5(8):
In Formulae CY71-1(1) to CY71-1(8), CY71-2(1) to CY71-2(8), CY71-3(1) to
CY71-3(32), CY71-4(1) to CY71-4(32), and CY71-5(1) to CY71-5(8),
each of X88 and X89 in Formulae CY71-2(1) to CY71-2(8), CY71-3(1) to CY71-3(32), and CY71-5(1) to CY71-5(8) may not be a single bond (e.g., at the same time), and
In Formula 3, 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).
In Formula 3, X901 to X904 may each independently be C or N.
In one or more embodiments, X901 may be C. For example, in some embodiments, X901 in Formula 3 may be C, and C may be carbon of a carbene moiety.
In one or more embodiments, X901 in Formula 3 may be N.
In one or more embodiments, X902 and X903 may each be C, and X904 may be N.
In Formula 3, i) a bond between X901 and M may be a coordinate bond, and ii) one of a bond between X902 and M, a bond between X903 and M, and a bond between X904 and M may be a coordinate bond, and the other two may each be a covalent bond.
For example, in some embodiments, a bond between X901 and M and a bond between X904 and M may each be a coordinate bond, and a bond between X902 and M and a bond between X903 and M may each be a covalent bond.
In one or more embodiments, X901 may be C, and a bond between X901 and M may be a coordinate bond.
In Formula 3, ring CY901 to ring CY904 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
For example, in some embodiments, ring CY901 may be a nitrogen-containing C1-C60 heterocyclic group.
In Formula 3, ring CY901 may be i) an X901-containing 5-membered ring, ii) an X901-containing 5-membered ring with which at least one 6-membered ring is condensed, or iii) an X901-containing 6-membered ring. In one or more embodiments, ring CY901 in Formula 3 may be i) an X901-containing 5-membered ring or ii) an X901-containing 5-membered ring with which at least one 6-membered ring is condensed. For example, in some embodiments, ring CY901 may include a 5-membered ring bonded to M in Formula 3 via X901. In this regard, the X901-containing 5-membered ring may be a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, or a thiadiazole group, and the X901-containing 6-membered ring and the 6-membered ring which may be optionally condensed to the X901-containing 5-membered ring may each independently be a benzene group, a pyridine group, or a pyrimidine group.
In one or more embodiments, ring CY901 may be an X901-containing 5-membered ring, and the X901-containing 5-membered ring may be an imidazole group or a triazole group.
In one or more embodiments, ring CY901 may be an X901-containing 5-membered ring with which at least one 6-membered ring is condensed, and the X901-containing 5-membered ring with which the at least one 6-membered ring is condensed may be a benzimidazole group or an imidazopyridine group.
In one or more embodiments, ring CY901 may be an imidazole group, a triazole group, a benzimidazole group, or an imidazopyridine group.
In one or more embodiments, X901 may be C, and ring CY901 may be an imidazole group, a triazole group, a benzimidazole group, a naphthoimidazole group, or an imidazopyridine group.
In one or more embodiments, ring CY902 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, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a benzofluorene group, a naphthobenzosilole group, a dinaphthofuran group, a dinaphthothiophene group, a dibenzocarbazole group, a dibenzofluorene group, a dinaphthosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azanaphthobenzofuran group, an azanaphthobenzothiophene group, an azabenzocarbazole group, an azabenzofluorene group, an azanaphthobenzosilole group, an azadinaphthofuran group, an azadinaphthothiophene group, an azadibenzocarbazole group, an azadibenzofluorene group, or an azadinaphthosilole group.
For example, in some embodiments, ring CY902 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, or a dibenzosilole group.
In Formula 3, ring CY903 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.
For example, in some embodiments, ring CY903 in Formula 3 may be: a C4-C6 monocyclic group; or a C8-C20 polycyclic group in which two or three C4-C6 monocyclic groups are condensed with each other.
The term “C2-C8 monocyclic group” as utilized herein refers to a non-condensed cyclic group. For example, the C2-C8 monocyclic group may be a cyclopentadiene group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a cycloheptadiene group, or a cyclooctadiene group.
For example, in some embodiments, ring CY903 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.
In Formula 3, ring CY904 may be a nitrogen-containing C1-C60 heterocyclic group.
For example, in one or more embodiments, ring CY904 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 Formula 3, L901 to L903 may each independently be a single bond, *—C(R1a)(R1b) —*′, *—C(R1a)═*′, *═C(R1a)—*′, *—C(R1a)═C(R1b)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C═C—*′, *—B(R1a)—*′, *—N(R1a)—*′, *—O—*′, *—P(R1a)—*′, *—Si(R1a)(R1b)—*′, *—P(═O)(R1a)—*′, *—S—*′, *—S(═O)—*′, *—S(═O)2—*′, or *—Ge(R1a)(R1b)—*′, wherein * and *′ each indicate a binding site to a neighboring atom.
R1a and R1b may each be as defined herein.
In one or more embodiments, L901 and L903 may each be a single bond, and L902 may be *—C(R1a)(R1b)—*′, *—B(R1a)—*′, *—N(R1a)—*′, *—O—*′, *—P(R1a)—*′, *—Si(R1a)(R1b)—*′, or *—S—*′.
In one or more embodiments, L902 may be *—O—*′ or *—S—*′.
In Formula 3, n901 to n903 indicate the number of L901 to the number of L903, respectively, and may each independently be an integer from 1 to 5. When each of n901 to n903 is 2 or more, each of two or more of L901(s) to two or more of L903(s) may be identical to or different from each other.
In one or more embodiments, n902 may be 1.
In Formula 3, R901 to R904, 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 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, Q1, Q2, and Q3 may each be as defined herein.
In one or more embodiments, R901 to R904, R1a, and R1b may each independently be:
Q1 to Q3 and Q31 to Q33 may each be as defined herein.
In one or more embodiments, R901 to R904, R1a, and R1b may each independently be:
In Formula 3, a901 to a904 indicate the number of R901 to the number of R904, respectively, and may each independently be an integer from 1 to 10. When each of n901 to n904 is 2 or more, each of two or more of L901(s) to two or more of L904(s) may be identical to or different from each other.
In Formulae 502 and 503,
In Formulae 502 and 503, a501 to a504 indicate the number of R501 to the number of R504, respectively, and each independently be an integer from 0 to 20. When a501 is 2 or more, two or more of R501(s) may be identical to or different from each other, when a502 is 2 or more, two or more of R502(s) may be identical to or different from each other, when a503 is 2 or more, two or more of R503(s) may be identical to or different from each other, and when a504 is 2 or more, two or more of R504(s) may be identical to or different from each other. In some embodiments, a501 to a504 may each independently be an integer from 0 to 8.
R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b utilized herein 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 as defined herein.
For example, in some embodiments, R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b in Formulae 502 and 503 may each independently be:
For example, in some embodiments, R10a as utilized herein may be:
In one or more embodiments, i) R1 to R3 in Formula 1, ii) R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, and R84b in Formulae 2-1 to 2-5 and R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b in Formulae 502 and 503, and iii) R10a may each independently be hydrogen, deuterium, —F, a cyano group, a nitro group, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a group represented by one of Formulae 9-1 to 9-19, a group represented by one of Formulae 10-1 to 10-246, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), or —P(═O)(Q1)(Q2) (wherein Q1 to Q3 may each be as defined herein):
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 heterocyclic compound represented by Formula 1 may be one selected from Compounds 1 to 50:
In one or more embodiments, the second compound may be at least one selected from among Compounds HTH1 to HTH40:
In one or more embodiments, the delayed fluorescence compound may be at least one selected from Compounds DFD1 to DFD29:
In the compounds above, “Ph” represents a phenyl group, “D5” represents substitution with five deuterium atoms, and “D4” represents substitution with four deuterium atoms. 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 in more detail 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 on the first electrode 110. The interlayer 130 may include an 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, an inorganic material such as a quantum dot, 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 neighboring emitting units. When the interlayer 130 includes the emitting units and the charge generation layer as described above, 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 multiple different materials, or iii) a multi-layer structure including multiple layers including multiple different materials.
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 one or more 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 each 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,
L201 to L204 may each independently be 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,
L205 may be *—O—*′, *—S—*′, *—N(Q201)—*′, a C1-C20 alkylene group unsubstituted or substituted with at least one R10a, a C2-C20 alkenylene group unsubstituted or substituted with at least one R10a, 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,
R201 and R202 may optionally be linked to each other via a single bond, a C1-C5 alkylene group unsubstituted or substituted with at least one R10a, or a C2-C5 alkenylene group unsubstituted or substituted with at least one R10a, to form a C8-C60 polycyclic group (for example, a carbazole group, etc.) unsubstituted or substituted with at least one R10a (for example, Compound HT16, etc.),
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 defined 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 the groups represented by Formulae CY201 to CY203.
In one or more embodiments, Formula 201 may include at least one selected from the groups represented by Formulae CY201 to CY203 and at least one selected from the groups represented by Formulae CY204 to CY217.
In one or more embodiments, in Formula 201, xa1 may be 1, R201 may be one selected from the groups represented by Formulae CY201 to CY203, xa2 may be 0, and R202 may be one selected from 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.
For example, in one or more embodiments, the hole transport region may include at least one selected from 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), and/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 the ranges described above, 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 the materials described above, 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 some 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 may be 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 may be 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 metal, metalloid, or any combination thereof, and element EL2 may be non-metal, metalloid, or any combination thereof.
Non-limiting examples of the metal may be: 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 may be silicon (Si), antimony (Sb), tellurium (Te), and/or the like.
Non-limiting examples of the non-metal may be oxygen (O), halogen (for example, F, Cl, Br, I, etc.), and/or the like.
Non-limiting examples of the compound including element EL1 and element EL2 may be 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 any combination thereof.
Non-limiting examples of the metal oxide may be 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, ReOs, etc.), and/or the like.
Non-limiting examples of the metal halide may be 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 may be LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, Lil, NaI, KI, RbI, CsI, and/or the like.
Non-limiting examples of the alkaline earth metal halide may be BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, BaI2, and/or the like.
Non-limiting examples of the transition metal halide may be titanium halides (for example, TiF4, TiCl4, 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, VBr3, 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.), iron(II) 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.), copper(I) halides (for example, CuF, CuCl, CuBr, CuI, 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 may be zinc halides (for example, ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halides (for example, InI3, etc.), tin halides (for example, SnI2, etc.), and/or the like.
Non-limiting examples of the lanthanide metal halide may be 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 may be antimony halides (for example, SbCl5, etc.) and/or the like.
Non-limiting examples of the metal telluride may be 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, Ta2 Te3, 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 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 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 an emitter). In one or more embodiments, the emission layer may further include an auxiliary dopant that promotes energy transfer to the dopant (or the emitter), in addition to the host and the dopant (or the emitter). When the emission layer includes the dopant (or the emitter) and the auxiliary dopant, the dopant (or the emitter) and the auxiliary dopant may be different from each other.
In one or more embodiments, the heterocyclic compound represented by Formula 1 may serve as the host. In one or more embodiments, the heterocyclic compound represented by Formula 1 may serve as the dopant (or the emitter) or as the auxiliary dopant.
An amount (weight) of the dopant (or the emitter) in the emission layer may be in a range of about 0.01 part by weight to about 15 parts by weight based on 100 parts by weight of the host.
In one or more embodiments, the emission layer may include the heterocyclic compound represented by Formula 1. An amount (weight) of the heterocyclic compound represented by Formula 1 in the emission layer may be in a range of about 30 parts by weight to about 99.99 parts by weight, about 40 parts by weight to about 90 parts by weight, or about 50 parts by weight to about 80 parts by weight, based on 100 parts by weight of the emission layer.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within the ranges described above, excellent or suitable luminescence characteristics may be obtained without a substantial increase in driving voltage.
In one or more embodiments, the host in the emission layer may include the heterocyclic compound or the second compound described herein, or any combination thereof.
In one or more embodiments, the host may include a compound represented by 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. For example, 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 Compounds H1 to H130, 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(carbazol-9-yl)benzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and/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 (two or more different kinds of compounds).
The emission layer may include, as a phosphorescent dopant, the transition metal-containing compound represented by Formula 3.
In one or more embodiments, the emission layer may include the transition metal-containing compound represented by Formula 3, wherein, when the transition metal-containing compound represented by Formula 3 serves as an auxiliary dopant, the emission layer may include a phosphorescent dopant.
The phosphorescent dopant may include at least one transition metal as a central metal.
The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
In some embodiments, the phosphorescent dopant may be electrically neutral.
For example, in one or more embodiments, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
For example, in one or more 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 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 defined with respect to T401.
In Formula 401, L402 may be an organic ligand. For example, in some embodiments, 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 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, at least one selected from among Compounds PD1 to PD25, and/or any combination thereof:
In one or more embodiments, the emission layer may include the transition metal-containing compound represented by Formula 3, wherein, when the transition metal-containing compound represented by Formula 3 serves as an auxiliary dopant, the emission layer may further include a fluorescent dopant.
In one or more embodiments, the emission layer may include the transition metal-containing compound represented by Formula 3, wherein, when the transition metal-containing compound represented by Formula 3 serves as a phosphorescent dopant, the emission layer may further include an auxiliary dopant.
The fluorescent dopant and the auxiliary dopant may each independently include an arylamine compound, a styrylamine compound, a boron-containing compound, or any combination thereof.
For example, 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,
For example, in some 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 with each other.
In one or more 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 FD36; 4,4′-bis(2,2-diphenylvinyl)-1, 1′-biphenyl (DPVBi); 4,4′-bis[4-(N,N-diphenylamino)styryl]biphenyl (DPAVBi); and/or any combination thereof:
In one or more embodiments, the fluorescent dopant and the auxiliary dopant may each independently include the delayed fluorescence compound represented by Formula 502 or 503.
The electron 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 multiple different materials, or iii) a multi-layer structure including multiple layers including multiple different materials.
The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
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 each stated order.
In one or more embodiments, the electron transport region (for example, the buffer layer, the hole blocking layer, the electron control layer, or the electron transport layer in the electron transport region) may include a metal-free compound including at least one IT 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:
For example, in some 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:
In 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 ET46, 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 (BAlq), 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), and/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 the ranges described above, 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 the materials described above, a metal-containing material.
The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. A metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and a metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may 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-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 multiple different materials, or iii) a multi-layer structure including multiple layers including multiple different materials.
The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any 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 oxide(s), halide(s) (for example, fluorides, chlorides, bromides, iodides, etc.), or telluride(s) 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: alkali metal oxides, such as Li2O, Cs2O, K2O, and/or the like; alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, RbI, and/or the like; 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 lanthanide metal tellurides. Non-limiting examples of the lanthanide metal telluride may be 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 bonded to the metal ion, for example, a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenyl benzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.
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, and, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the ranges described above, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 150 may be on the interlayer 130 having a structure as described above. In one or more embodiments, 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 lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ytterbium (Yb), silver-ytterbium (Ag—Yb), ITO, IZO, 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 may be 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 selected from among the first capping layer and 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 optionally be substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In an embodiment, at least one selected from the first capping layer and the second capping layer may (e.g., the first capping layer and the second capping layer may each) independently include an amine group-containing compound.
For example, in one or more embodiments, at least one selected from the first capping layer and 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 selected from the first capping layer and 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; Compounds CP1 to CP6; β-NPB; and/or any combination thereof:
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 direction in which light emitted from the light-emitting device travels. For example, in some embodiments, the light emitted from the light-emitting device may be blue light, green light, or white light (e.g., combined white light). Details of the light-emitting device may be as described herein. In an embodiment, 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 to emit first color light, a second area to emit second color light, and/or a third area 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. For example, in some 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) a (e.g., any) quantum dot. 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. In this regard, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths. 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 described above. The thin-film transistor may include a source electrode, a drain electrode, and an activation layer, wherein one selected from 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.
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 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 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 any 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 resin (for example, polymethyl methacrylate, polyacrylic acid, etc.), an epoxy-based resin (for example, aliphatic glycidyl ether (AGE), etc.), or any combination thereof; or a 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 apparatus 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 device 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 in the y-axis direction may be different from each other. For example, 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 apparatus, 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 filler/pillar provided at a boundary between doors, and/or the like. The chassis of the vehicle 1000 may include a power generating apparatus, a power transmitting apparatus, a driving apparatus, a steering apparatus, a braking apparatus, a suspension apparatus, a transmission apparatus, a fuel apparatus, front and rear wheels, 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 apparatus 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 an embodiment, 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 an embodiment, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In an embodiment, 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 an embodiment, the side window glasses 1100 may be spaced apart from each other in the x-direction or the −x-direction. For example, in some embodiments, 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 to each other may extend in the x-direction or the −x-direction. For example, the 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 body. In an 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, a turn indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, a hodometer, an automatic shift selector indicator light, 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 apparatus, an air conditioning apparatus, and/or a heater of a seat are arranged. 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 an embodiment, the cluster 1400 may be arranged to correspond to a driver seat, and the passenger seat dashboard 1600 may be arranged to correspond to a front passenger seat. In an embodiment, 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 an embodiment, the display apparatus 2 may include a display panel 3, and the display panel 3 may display an image. The display apparatus 2 may be arranged inside the vehicle 1000. In an embodiment, the display apparatus 2 may be arranged between the side window glasses 1100 facing each other. The display apparatus 2 may be arranged on at least one selected from among the cluster 1400, the center fascia 1500, and the passenger seat dashboard 1600.
The display apparatus 2 may include an organic light-emitting display apparatus, an inorganic light-emitting display apparatus, a quantum dot display apparatus, and/or the like. Hereinafter, as the display apparatus 2 according to one or more embodiments of the present disclosure, an organic light-emitting display apparatus including the light-emitting device according to the present disclosure will be described as an example, but one or more suitable types (kinds) of display apparatuses as described above may be utilized in embodiments of the present disclosure.
Referring to
Referring to
Referring to
Respective layers included in the hole transport region, the emission layer, and respective layers included in the electron transport region may be formed in a certain region by utilizing one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, laser-induced thermal imaging, and/or the like.
When respective layers included in the hole transport region, the emission layer, and respective layers included in the electron transport region are formed by vacuum deposition, the deposition may be performed at a deposition temperature of about 100° C. to about 500° C., a vacuum degree of about 10−8 torr to about 10−3 torr, and a deposition speed 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 3 to 60 carbon atoms, and the term “C1-C60 heterocyclic group” as utilized herein refers to a cyclic group that has 1 to 60 carbon atoms and further has, in addition to carbon, a heteroatom as a ring-forming atom. The C5-C60 carbocyclic group and the C1-C60 heterocyclic group may each be a monocyclic group including (e.g., consisting of) one ring or a polycyclic group in which two or more rings are condensed with each other. For example, the C1-C60 heterocyclic group has 3 to 61 ring-forming atoms.
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 π electron-rich C3-C60 cyclic group may be i) a T1 group, ii) a condensed cyclic group in which at least two T1 groups are condensed with each other, iii) a T3 group, iv) a condensed cyclic group in which at least two T3 groups are condensed with each other, or v) a condensed cyclic group in which at least one T3 group and at least one T1 Group are condensed with each other (for example, the C3-C60 carbocyclic group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, etc.),
the π electron-deficient nitrogen-containing C1-C60 heterocyclic group may be i) a T4 group, ii) a condensed cyclic group in which at least two T4 groups are condensed with each other, iii) a condensed cyclic group in which at least one T4 group and at least one T1 group are condensed with each other, iv) a condensed cyclic group in which at least one T4 group and at least one T3 group are condensed with each other, or v) a condensed cyclic group in which at least one T4 group, at least one T1 group, and at least one T3 group are condensed with one another (for example, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, etc.),
the T1 group may be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or bicyclo[2.2.1]heptane) group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, or a benzene group,
The 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.”
Depending on context, in the present disclosure, a divalent group may refer or be a polyvalent group (e.g., trivalent, tetravalent, etc., and not just divalent) per, e.g., the structure of a formula in connection with which of the terms are utilized.
Non-limiting examples of the monovalent C3-C60 carbocyclic group and the monovalent C1-C60 heterocyclic group may be a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C5-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 may be 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 1 to 60 carbon atoms, and non-limiting examples thereof may be 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, a tert-decyl group, and/or the like. 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 may be 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 may be 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 may be 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 may be 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 may be 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 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and non-limiting examples thereof may be 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 may be 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-C10 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-C60 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 may be 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 may be 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, a naphthyridinyl group, and/or the like. 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 may be 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.
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 may be a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphthoindolyl group, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indeno carbazolyl 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, a benzothienodibenzothiophenyl group, and/or the like. 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.
The term “C6-C60 aryloxy group” as utilized herein refers to —OA102 (wherein A102 is a C6-C60 aryl group), and the term “C6-C60 arylthio group” as utilized herein refers to —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 as utilized herein may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; —SCN; or 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.
The term “heteroatom” as utilized herein refers to any atom other than a carbon atom. Non-limiting examples of the heteroatom may be O, S, N, P, Si, B, Ge, Se, and any combination thereof.
The term “third-row transition metal” as utilized herein may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), and/or the like.
The term “Ph” as utilized herein refers to a phenyl group, the term “Me” as utilized herein refers to a methyl group, the term “Et” as utilized herein refers to an ethyl group, the term “tert-Bu” or “But” as utilized herein refers to a tert-butyl group, and the term “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 other words, the “biphenyl group” is 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 other words, the “terphenyl group” is 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.
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 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.
After bromobenzene (CAS #: 108-86-1) was reacted with n-BuLi, (trichlorosilyl)cyclohexane (CAS #: 98-12-4) was added thereto, and the mixture was stirred for 2 hours to obtain Intermediate 1-1. Meanwhile, after 1,3-dibromobenzene (CAS #: 108-36-1) was reacted with n-BuLi, Intermediate 1-1 was added thereto, and the mixture was stirred overnight at room temperature to obtain Intermediate 1-2. Intermediate 1-2 was identified by liquid chromatography-mass spectroscopy (LC-MS).
C24H25BrSi M+1: 423.09
After Intermediate 1-2 was reacted with n-BuLi, trimethyl borate (CAS #: 121-43-7) was added thereto, the mixture was stirred overnight at room temperature, and then, H2O was added thereto to obtain Intermediate 1-3. Intermediate 1-3 was identified by LC-MS.
C24H27BO2Si M+1: 387.20
After 9H-carbazole (CAS #: 86-74-8) was reacted with n-BuLi, cyanuric chloride (CAS #: 108-77-0) was added thereto, and the mixture was stirred overnight at a temperature of 70° C. to obtain Intermediate 1-4. Intermediate 1-4 was identified by LC-MS.
C27H16ClN5 M+1:446.14
2.5 g of Intermediate 1-4, 2.38 g of Intermediate 1-3, 0.26 g of Pd(PPh3)4, 1.94 g of K2CO3 (in 7 mL of H2O), 7 mL of EtOH, and 28 mL of toluene were added to a round bottom flask (RBF), and the mixture was stirred overnight at a temperature of 120° C. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing ethylacetate. An organic layer collected therefrom was dried with magnesium sulfate, and a solvent was evaporated therefrom. A residue thus obtained was then separated and purified by silica gel column chromatography to obtain 2.6 g (yield: 62%) of Compound 1. Compound 1 was identified by LC-MS.
C51H41N5Si M+1:752.33
After bromobenzene (CAS #: 108-86-1) was reacted with n-BuLi, dichlorodicyclohexylsilane (CAS #: 18035-74-0) was added thereto, and the mixture was stirred for 2 hours to obtain Intermediate 6-1. Meanwhile, after 1,3-dibromobenzene (CAS #: 108-36-1) was reacted with n-BuLi, Intermediate 6-1 was added thereto, and the mixture was stirred overnight at room temperature to obtain Intermediate 6-2. Intermediate 6-2 was identified by LC-MS.
C24H31BrSi M+1:429.15
After Intermediate 6-2 was reacted with n-BuLi, trimethyl borate (CAS #: 121-43-7) was added thereto, the mixture was stirred overnight at room temperature, and then, H2O was added thereto to obtain Intermediate 6-3. Intermediate 6-3 was identified by LC-MS.
C24H33BO2Si M+1:393.23
2.5 g of Intermediate 1-4, 2.42 g of Intermediate 6-3, 0.26 g of Pd(PPh3)4, 1.94 g of K2CO3 (in 7 mL of H2O), 7 mL of EtOH, and 28 mL of toluene were added to an RBF, and the mixture was stirred overnight at a temperature of 120° C. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing ethylacetate. An organic layer collected therefrom was dried with magnesium sulfate, and a solvent was evaporated therefrom. A residue thus obtained was then separated and purified by silica gel column chromatography to obtain 2.55 g (yield: 60%) of Compound 6. Compound 6 was identified by LC-MS.
C51H47N5Si:758.39
After 3-bromobiphenyl (CAS #: 2113-57-7) was reacted with n-BuLi, dichlorodicyclohexylsilane (CAS #: 18035-74-0) was added thereto, and the mixture stirred for 2 hours to obtain Intermediate 11-1. Meanwhile, after 1,3-dibromobenzene (CAS #: 108-36-1) was reacted with n-BuLi, Intermediate 11-1 was added thereto, and the mixture was stirred overnight at room temperature to obtain Intermediate 11-2. Intermediate 11-2 was identified by LC-MS.
C30H35BrSi M+1:505.16
After Intermediate 11-2 was reacted with n-BuLi, trimethyl borate (CAS #: 121-43-7) was added thereto, the mixture was stirred overnight at room temperature, and then, H2O was added thereto to obtain Intermediate 11-3. Intermediate 11-3 was identified by LC-MS.
C30H37BO2Si M+1:469.30
2.5 g of Intermediate 1-4, 2.89 g of Intermediate 11-3, 0.26 g of Pd(PPh3)4, 1.94 g of K2CO3 (in 7 mL of H2O), 7 mL of EtOH, and 28 mL of toluene were added to an RBF, and the mixture was stirred overnight at a temperature of 120° C. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing ethylacetate. An organic layer collected therefrom was dried with magnesium sulfate, and a solvent was evaporated therefrom. A residue thus obtained was then separated and purified by silica gel column chromatography to obtain 2.95 g (yield: 63%) of Compound 11. Compound 11 was identified by LC-MS.
C57H51N5Si M+1:834.39
After 9H-carbazole (CAS #: 86-74-8) was reacted with n-BuLi, cyanuric chloride (CAS #: 108-77-0) was added thereto, and the mixture was stirred at a temperature of 70° C. for 2 hours and then stirred overnight at room temperature to obtain Intermediate 26-1. Intermediate 26-1 was identified by LC-MS.
C15H8Cl2N4 M+1:315.01
Intermediate 26-1 and phenylboronic acid (CAS #: 98-80-6) were stirred overnight in the presence of a Pd catalyst to obtain Intermediate 26-2. Intermediate 26-2 was identified by LC-MS.
C21H13ClN4 M+1:357.10
2.5 g of Intermediate 26-2, 2.98 g of Intermediate 1-3, 0.32 g of Pd(PPh3)4, 2.42 g of K2CO3 (in 8 mL of H2O), 8 mL of EtOH, and 32 mL of toluene were added to an RBF, and the mixture was stirred overnight at a temperature of 120° C. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing ethylacetate. An organic layer collected therefrom was dried with magnesium sulfate, and a solvent was evaporated therefrom. A residue thus obtained was then separated and purified by silica gel column chromatography to obtain 3.02 g (yield: 65%) of Compound 26. Compound 26 was identified by LC-MS.
C45H38N4Si M+1:663.33
2.5 g of Intermediate 26-2, 3.02 g of Intermediate 6-3, 0.32 g of Pd(PPh3)4, 2.42 g of K2CO3 (in 8 mL of H2O), 8 mL of EtOH, and 32 mL of toluene were added to RBF, and the mixture was stirred overnight at a temperature of 120° C. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing ethylacetate. An organic layer collected therefrom was dried with magnesium sulfate, and a solvent was evaporated therefrom. A residue thus obtained was then separated and purified by silica gel column chromatography to obtain 2.86 g (yield: 61%) of Compound 31. Compound 31 was identified by LC-MS.
C45H44N4Si M+1:669.35
2.0 g of Intermediate 26-1, 6.54 g of Intermediate 6-3, 0.59 g of Pd(PPh3)4, 4.39 g of K2CO3 (in 15 mL of H2O), 15 mL of EtOH, and 60 mL of toluene were added to an RBF, and the mixture was stirred overnight at a temperature of 120° C. After the reaction was completed, an extraction process was performed on the reaction solution by utilizing ethylacetate. An organic layer collected therefrom was dried with magnesium sulfate, and a solvent was evaporated therefrom. A residue thus obtained was then separated and purified by silica gel column chromatography to obtain 3.46 g (yield: 58%) of Compound 46. Compound 46 was identified by LC-MS.
C63H70N4Si2 M+1:939.52
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 of Synthesis Examples.
As an anode, a Corning 15 Ω/cm2 (1,200 Å) ITO glass substrate was cut to a size of 50 mm×50 mm×0.5 mm, sonicated with isopropyl alcohol and pure water each for 5 minutes, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the resultant ITO glass substrate was loaded onto a vacuum deposition apparatus.
First, HATCN was vacuum-deposited on the substrate to form a hole injection layer having a thickness of 100 Å. Next, BCFN as a first hole transport material was vacuum-deposited thereon to a thickness of 600 Å, and then, SiCzCz as a second hole transport material was vacuum-deposited thereon to a thickness of 50 Å, thereby forming a hole transport layer.
SiCzCz as a host, Compound 1, and PtON-TBBI as a phosphorescent dopant were co-deposited on the hole transport layer at a weight ratio of 60:27:13 to form an emission layer having a thickness of 350 Å.
Subsequently, mSiTrz was deposited on the emission layer to form a first electron transport layer having a thickness of 50 Å, and then, mSiTrz and LiQ were co-deposited thereon at a weight ratio of 1:1 to form a second electron transport layer having a thickness of 350 Å, thereby forming an electron transport layer.
LiF as an alkali metal halide was deposited on the electron transport layer to form an electron injection layer having a thickness of 15 Å, and then, Al was vacuum-deposited thereon to form a LiF/Al electrode having a thickness of 80 Å, thereby completing the 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 Compound 1 as a host was changed/replaced by a corresponding compound shown in Table 1 in forming an emission layer.
To evaluate the characteristics of each of the organic light-emitting devices manufactured in Examples 1 to 6 and Comparative Examples 1 and 2, the driving voltage at a current density of 10 mA/cm2, current density, and maximum quantum efficiency thereof were measured.
The driving voltage and current density of the organic light-emitting devices were each measured utilizing a source meter (Keithley Instruments Inc., 2400 series), and the maximum quantum efficiency of the organic light-emitting devices was each measured utilizing the external quantum efficiency measurement apparatus C9920-2-12 of Hamamatsu Photonics Inc.
In evaluating the maximum quantum efficiency, the luminance/current density was measured utilizing a luminance meter that was calibrated for wavelength sensitivity, and the maximum quantum efficiency was converted by assuming an angular luminance distribution (Lambertian) which introduced a perfect reflecting diffuser.
The evaluation results of the characteristics of each of the organic light-emitting devices are shown in Table 1.
From Table 1, it was confirmed that the organic light-emitting devices according to Examples 1 to 6 each had superior maximum quantum efficiency compared to the organic light-emitting devices according to Comparative Examples 1 and 2.
According to the one or more embodiments, the utilization of the heterocyclic compound may enable the manufacture of a light-emitting device having improved luminescence efficiency, color purity, and lifespan and a high-quality electronic apparatus including the light-emitting device.
In the present disclosure, it will be understood that the terms “comprise(s),” “include(s),” or “have/has” specify 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 following claims and equivalents thereof.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2023-0011945 | Jan 2023 | KR | national |
